[Federal Register Volume 79, Number 241 (Tuesday, December 16, 2014)]
[Notices]
[Pages 74790-74794]
[FR Doc No: 2014-29361]

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SECURITIES AND EXCHANGE COMMISSION

[Release No. 34-73805; File No. SR-FICC-2014-11]

Self-Regulatory Organizations; Fixed Income Clearing Corporation;
Notice of Filing of Proposed Rule Change To Amend the Government
Securities Division Rulebook and the Mortgage Backed Securities
Clearing Rules In Order To Move the Time of Novation With Respect to
Certain Trades, Include Rules To Reflect Existing Processes, and
Clarify Certain Rules To Reflect Current Practices

December 10, 2014.
    Pursuant to Section 19(b)(1) of the Securities Exchange Act of 1934
(the ``Act''),\1\ and Rule 19b-4,\2\ notice is hereby given that on
December 2, 2014, Fixed Income Clearing Corporation (``FICC'') filed
with the Securities and Exchange Commission (``Commission'') the
proposed rule change as described in Items I, II, and III below, which
Items have been prepared by FICC. The Commission is publishing this
notice to solicit comments on the proposed rule change from interested
persons.
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    \1\ 15 U.S.C. 78s(b)(1).
    \2\ 17 CFR 240.19b-4.
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I. Clearing Agency's Statement of the Terms of Substance of the
Proposed Rule Change

    FICC is proposing to (1) move the time of novation for netting
eligible transactions submitted to the Government Securities Division
(``GSD'') in accordance with the GSD Rulebook (``GSD Rules'') and for
SBO-Destined Trades \3\ submitted to the Mortgage-Backed Securities
Division (``MBSD'') in accordance with the MBSD Clearing Rules (``MBSD
Rules'') in order to provide members with additional legal certainty
that FICC will be the legal counterparty with respect to their
guaranteed trades for purposes of regulatory capital requirements, (2)
include rules to reflect existing processes, and (3) clarify certain
rules to reflect current practices.
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    \3\ The MBSD Rules define a ``SBO-Destined Trade'' as a to-be-
announced (``TBA'') transaction in the clearing system intended for
TBA Netting in accordance with the provisions of the Rules. MBSD
Rule 1, Definitions. In a TBA transaction, members agree on a sale
price, quantity, and the characteristics of the securities being
sold, but they do not specify which particular securities will be
delivered on the settlement date.
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II. Clearing Agency's Statement of the Purpose of, and Statutory Basis
for, the Proposed Rule Change

    In its filing with the Commission, FICC included statements
concerning the purpose of and basis for the proposed rule change and
discussed any comments it received on the proposed rule change. The
text of these statements may be examined at the places specified in
Item IV below. FICC has prepared summaries, set forth in sections A, B
and C below, of the most significant aspects of such statements.

A. Clearing Agency's Statement of the Purpose of, and Statutory Basis
for, the Proposed Rule Change.

1. Purpose
    FICC is proposing to move the time of novation applicable to
certain transactions submitted to the GSD and MBSD to earlier in the
clearing process in order to provide members with additional legal
certainty that FICC will be their legal counterparty with respect to
their guaranteed trades for purposes of members' regulatory capital
requirements.
    Currently, GSD and MBSD guarantee the settlement of a trade upon
comparison, which generally occurs when FICC issues initial ``output''
to GSD netting members or MBSD clearing members, as applicable,
indicating that their trades have compared,\4\ provided that the trade
meets the requirements of the GSD Rules or the MBSD Rules, as
applicable.\5\ This means that FICC is responsible for settling the
guaranteed trades, even if one of the members who submitted the trade
becomes insolvent.
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    \4\ In the case of GSD locked-in trades, comparison occurs upon
receipt of the trade data submitted to FICC from the locked-in trade
source. GSD Rule 6C.
    \5\ See GSD Rule 11B and MBSD Rule 5.
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    Novation, which refers to the termination of delivery, receive and
related payment obligations between the original parties to the
contract and the replacement of such obligations with identical
obligations between each party and FICC, currently does not occur until
later in the clearing and settlement process than comparison. In GSD,
novation currently occurs when subsequent ``netting output'' is issued
to netting members (usually the day before settlement); in MBSD,
novation currently occurs when subsequent ``pool netting output'' is
issued to clearing members (usually the day before settlement).
    Because there is a legal distinction between the concept of
``guarantee'' and ``novation'', and this legal distinction may have a
bearing on how members calculate their capital requirement, FICC
proposes to move the time of novation (i.e. the point that FICC becomes
the legal counterparty) so that it occurs at the time of the trade
guarantee.

Time of Novation--Proposed Changes
    FICC is proposing to revise the GSD Rules and MBSD Rules so that
novation will occur at comparison for netting eligible transactions
(for GSD) and SBO-Destined Trades (for MBSD). This means that, at the
point of trade comparison, FICC will guarantee the settlement of the
transactions (as it does today) and novate such transactions, becoming
the legal counterparty to each submitting member with respect to such
transactions.
    Under the proposal, in the GSD, all netting eligible transactions
that compare in accordance with the GSD Rules will novate at the point
of comparison.
    In the MBSD, only SBO-Destined Trades, all of which are included in
the TBA Netting process and (pursuant to proposed Section 7 of Rule 8
which is being added to reflect a current requirement and current
practice) must be submitted to the Pool Netting process,\6\ will novate
at the point of comparison. Other types of transactions, including
Trade-for-Trade Transactions \7\ and Specified Pool Trades,\8\ will
continue to be guaranteed at comparison, as they are today, but FICC
will not novate such transactions at comparison. Instead, such
transactions will be treated as they are today: (1) To the extent
Trade-for-Trade Transactions are included in the Pool Netting
process,\9\ FICC will novate such Transactions once the Pool Netting
\10\ process is completed and (2) Specified Pool Trades, which are not
included in the TBA Netting process nor the Pool Netting process, are
not novated today (they settle outside of FICC between the submitting
counterparties) and will continue to not be novated under the
proposal.\11\
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    \6\ The MBSD conducts two separate netting processes to
consolidate settlement obligations and reduce the number of
securities and the amount of cash that must be exchanged to settle
transactions. TBA Netting is the process used to net SBO-Destined
Trades that have compared in accordance to the MBSD Rules. TBA
Netting is conducted before particular securities (``pools'') are
identified to the SBO-Destined Trades. Pool Netting, which occurs
after MBSD clearing members allocate pools to transactions, is the
process used to aggregate and match offsetting pool delivery
obligations submitted by MBSD clearing members to satisfy their
settlement obligations. MBSD Rules 6 and 7. An MBSD clearing member
may submit a transaction to Pool Netting even if such transaction
was not submitted for TBA Netting.
    \7\ The MBSD Rules define ``Trade-for-Trade Transaction'' as a
TBA transaction submitted to FICC not intended for TBA Netting in
accordance with the provisions of the Rules. MBSD Rule 1,
Definitions.
    \8\ The MBSD Rules define ``Specified Pool Trades'' as a trade
in which all required pool data, including the pool number to be
delivered on the contractual settlement date, are agreed upon by the
clearing member at the time of execution. MBSD Rule 1, Definitions.
    \9\ Trade-for-Trade Transactions that are not submitted to the
Pool Netting process must be settled outside of FICC between the
submitting counterparties.
    \10\ As noted in SR-FICC-2008-01, a clearing member that has a
trade that was matched with a stipulation (``Stip Trade'') would not
submit such trade for Pool Netting. Pool Netting creates delivery
obligations based off the net position of clearing members without
regard to the original counterparty relationship. With a Stip Trade,
the buyer and seller will want to ensure the receipt or delivery, as
applicable, is maintained between themselves to ensure that the
other party adheres to the stipulated terms. Securities Exchange Act
Release No. 34-66550 (March 9, 2012), 77 FR 15155 (March 14, 2014)
(SR-FICC-2008-01). Therefore, as with the current process, FICC does
not expect to novate Stip Trades.
    \11\ MBSD Rule 10.
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    In order to effectuate this change in the time of novation as
described above, the proposed rule change adds language to the GSD
Rules (new Section 8 of Rule 5) and MBSD Rules (new Section 13 of Rule
5) that states that FICC will guarantee and now novate applicable
transactions upon comparison, subject to the parameters set forth in
the proposed rule change. Conforming changes are proposed to be made to
GSD Rule 3A, GSD Rule 6B, GSD Rule 6C, GSD Rule 11, GSD Rule 14, GSD
Rule 20, GSD Rule 21A, Rule 22B, MBSD Rule 6, MBSD Rule 8, MBSD Rule
10, MBSD Rule 11 and MBSD Rule 17A. In addition, the definition of
``novation'' in both Divisions' Rule 1 is clarified to reflect that
delivery, receive and related payment obligations between members will
be terminated and replaced with identical obligations to and from FICC
at the point in time that the trade is compared in accordance with the
applicable Rules.
    The proposed rule change also addresses the fact that in the MBSD
today certain settlement obligations continue to be settled between the
settlement counterparties and not vis-[agrave]-vis FICC; these are the
obligations that were not included in the Pool Netting process pursuant
to MBSD Rule 8 (Pool Netting). The present proposal does not change
this existing process. However, because the present proposal introduces
legal novation at comparison for certain MBSD transactions, the
proposed rule changes (in Rule 5, Section 2) make clear that the
settlement counterparties continue to settle with each other but do so
on behalf of FICC for those transactions that are novated to FICC.
    The proposal to move the time of novation as noted above does not
change FICC's risk. Because FICC currently guarantees eligible trades
upon comparison, FICC already assumes responsibility for settling such
trades at the point of comparison. Adding legal novation at the point
of comparison does not increase FICC's obligations and therefore, does
not require any changes to FICC's risk management processes. In
addition, FICC is not proposing to change its operational processes.
Proposed Formalization of Existing Processes
    In addition, the proposed rule changes formalize the following
existing processes:
     As noted above, Section 7 of MBSD Rule 8 is added to state
that all SBOO Trades and SBON Trades (i.e., SBO-Destined Trades after
such trades have gone through TBA Netting) must be submitted to Pool
Netting.
     MBSD Rules 15 and 16 are revised to clarify that, upon the
insolvency of a member's original counterparty to a compared trade,
such member cannot unilaterally modify its obligations with respect to
transactions originally entered with such counterparty. In the MBSD
Rules, because certain trades are not novated and will continue to not
be novated under this proposal, FICC proposes to make clear that upon a
cease to act with respect to a member by FICC, the solvent member to a
compared trade with the defaulting member may not unilaterally act with
respect to such trade.
    These changes are not intended to change FICC's current operations
or processes.
Proposed Clarification To Reflect Current Processes
    In addition, the proposed rule changes clarify certain Rules to
reflect actual practices and requirements as follows:
     MBSD Rule 17 is revised to clarify that when FICC ceases
to act for a member, FICC may dispose of such member's Trade-for-Trade
Transactions based upon their generic terms. These changes are not
intended to change FICC's current operations or processes.
Specific Proposed Changes
    With respect to the GSD Rules, the proposed changes are as follows:
     The term ``Interactive Submission Method'' is revised to
correct a typographical error.
     For clean-up and clarification purposes, the term
``Novation'' is revised to reflect that delivery, receive and related
payment obligations between GSD netting members will be terminated and
replaced with identical obligations to and from FICC at the point in
time that the trade is compared in accordance to the GSD Rules.
     Rule 3A, Sections 2(i), 7(a), 7(d), 14(c), and 16(a) are
revised to reflect

that trades submitted by Sponsored Members \12\ will novate to FICC at
the time that such trades receive FICC's guaranty of settlement.
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    \12\ The term ``Sponsored Member'' means any Person that has
been approved by the Corporation to be sponsored into membership by
a Sponsoring member pursuant to Rule 3A. GSD Rule 1, Definitions.
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     Rule 5 is revised to include a new Section 8 entitled
``Novation and Guaranty of Compared Trades'' which provides for the
following: (1) Compared trades that meet the requirements of the GSD
Rules and were entered into in good faith will novate to FICC and FICC
will guarantee the settlement for each such compared trade; (2) if a
compared trade becomes uncompared or cancelled, FICC's guaranty and
novation of such trade will be reversed and cancelled; (3) if a
compared trade is modified after novation and such modification does
not cause the trade to become uncompared, then the modification will
cause a corresponding modification to the deliver, receive and related
payment obligations between the GSD netting members and FICC; (4) at
the time that a compared trade becomes novated, such trade ceases to be
bound by any bilateral agreement between the parties with respect to
the deliver, receive and related payment obligations, however, if the
trade becomes uncompared or is cancelled, such trade shall be governed
by the bilateral agreement that governed the trade prior to the
novation; and (5) if a right of substitution was established by the
parties to a repurchase transaction, such right will continue and be
recognized by FICC after novation.
     Rule 6B, Section 4 deletes the provision which states that
an uncompared trade will cease to be guaranteed by FICC because this
concept is now covered in Rule 5, Section 8.
     Rule 6C, Section 10 deletes the provision which states
that a locked-in trade that becomes uncompared will cease to be
guaranteed by FICC because this concept is now covered in Rule 5,
Section 8.
     Rule 6C, Section 11 deletes the provision which states
that a netting eligible auction purchase that becomes uncompared will
cease to be guaranteed by FICC because this concept is now covered in
Rule 5, Section 8.
     Rule 6C, Section 12 deletes the provision which states
that a GCF Repo Transaction \13\ that becomes uncompared will cease to
be guaranteed by FICC because this concept is now covered in Rule 5,
Section 8.
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    \13\ Pursuant to the GSD Rules, the term ``GCF Repo
Transaction'' means a Repo Transaction involving generic CUSIP
numbers the data on which are submitted to FICC on a locked-in-trade
basis pursuant to the provisions of Rule 6C, for netting and
settlement by FICC pursuant to the provisions of Rule 20. GSD Rule
1, Definitions.
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     Rule 11, Section 6 is revised to reflect that (1) novation
occurs at comparison; and (2) at netting, the previously novated
deliver, receive and related payment obligations between the netting
members and FICC will be terminated and replaced by net deliver,
receive and related payment obligations as listed in the report made
available by FICC to the netting members.
     Rule 11B is revised to correct typographical errors.
     Rule 14, Section 3 is revised to reflect that (1) novation
occurs at comparison; and (2) at netting, the previously novated
deliver, receive and related payment obligations between the netting
members and FICC created by Forward Trades will be terminated and
replaced by net deliver, receive and related payment obligations as
listed in the report made available by FICC to the netting members.
     Rule 20, Section 5 is revised to reflect that with respect
to GCF Repo[supreg] transactions, novation will occur at comparison in
accordance with Rule 5, Section 8.
     Rule 21A is revised to incorporate the concept of
novation.
     Rule 22B included a sentence providing that upon FICC's
default, trades that had compared would be deemed novated. Because the
GSD Rules are being revised to reflect that novation occurs at
comparison, this sentence is no longer necessary. As a result, it is
being deleted in connection with this proposal.
    With respect to the MBSD Rules, the proposed changes are as
follows:
     For clean-up and clarification purposes, the term
``Novation'' is revised to reflect that delivery, receive and related
payment obligations between MBSD clearing members will be terminated
and replaced with identical obligations to and from FICC in accordance
with the MBSD Rules.
     The term ``SBO Contra-Side Member'' is revised to correct
a typographical error.
     The term ``SBO Net-Out Position'' is revised to clarify
that the term is used in connection with offsetting purchase and sale
SBO-Destined Trades that were originally between different clearing
members (but, once novated at comparison, are between such members and
FICC).
     The term ``SBO Net-Out Unit'' is being deleted because
this term is not used in the MBSD Rules.
     The term ``SBO Netted Position'' is revised to clarify
that the term is used in connection with offsetting purchase and sale
SBO-Destined Trades that were originally between the same clearing
members (but, once novated at comparison, are between such members and
FICC).
     The term ``SBON Trade'' is revised to correct a
typographical error.
     The term ``SBOO Trade'' is revised to correct a
typographical error.
     Rule 5, Section 1 is revised to correct a typographical
error.
     Rule 5, Section 2 is revised to reflect that (1)
transactions that are not novated pursuant to this proposal (pursuant
to new Section 13 of Rule 5 discussed below) and not netted and novated
through the Pool Netting system will be settled directly between the
Members; and (2) transactions novated pursuant to new Section 13 of
Rule 5 and not thereafter netted through the Pool Netting system
pursuant to Rule 8 will settle between Members on behalf of FICC.
     Rule 5, Section 12 is revised to correct a typographical
error.
     Rule 5 includes a new Section 13 entitled ``Novation''
which states the following: (1) FICC will guarantee and novate SBO-
Destined Trades that meet the requirement of the MBSD Rules and have
been entered into in good faith; (2) FICC will not novate SBO-Destined
Trades that are partially compared; (3) to the extent a partially
compared SBO-Destined Trade becomes fully compared, FICC will novate
such trade; (4) if a trade becomes uncompared or cancelled, the
guaranty and novation of such transaction shall be reversed; (5) at the
time that an SBO-Destined Trade is novated to FICC, such trade shall
cease to be bound by any bilateral agreement between the parties to the
trade with respect to the deliver, receive and related payment
obligations, however, if the trade becomes uncompared or is cancelled,
such trade shall be governed by the bilateral agreement that governs
such trade prior to the novation.
     Rule 6, Sections 1(a), (b) and (c) are revised to take
into account the fact that SBO-Destined Trades are novated upon
comparison and are, therefore, legally between MBSD Clearing Members
and FICC after comparison.
     Rule 8, Section 6 is revised to take into account the fact
that SBO-Destined Trades are novated upon comparison and are,
therefore, legally between MBSD Clearing Members and FICC after
comparison.
     Rule 8 includes a new Section 7 which is entitled
``Obligations to Submit SBOO and SBON Trades to Pool Netting''. This
Section reflects a current

requirement and current practice that clearing members are required to
submit all SBOO trades and SBON trades (i.e., SBO-Destined Trades after
such trades have gone through TBA Netting) for inclusion in the Pool
Netting system.
     Rule 10, Section 2 is revised to clarify that clearing
members are required to submit a notification of settlement for SBO
Trades that are novated at comparison and processed through the TBA
Netting system but that are not thereafter submitted to the Pool
Netting system.
     Rule 11, Section 1 is revised to take into account the
fact that SBO Trades are novated upon comparison and are, therefore,
legally between MBSD Clearing Members and FICC after comparison.
     Rule 15 is revised to clarify the current process with
respect to transactions submitted to and compared by FICC, whereby in
the event a member's original counterparty goes insolvent, such member
cannot unilaterally modify its obligations with respect to transactions
originally entered with such counterparty.
     Rule 16 is revised to clarify the current process with
respect to transactions submitted to and compared by FICC, whereby in
the event a member's original counterparty goes insolvent, such member
cannot unilaterally modify its obligations with respect to transactions
originally entered with such counterparty.
     Rule 17, Section 2 is revised to clarify the current
process, whereby when FICC ceases to act for a clearing member, such
member's Trade-for-Trade Transactions \14\ may be disposed of based
upon their generic terms such as agency, product, coupon rate and
maturity. The other changes are typographical corrections.
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    \14\ Including ``stip'' trades and any other TBA transactions
not intended for TBA Netting.
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     Rule 17A is revised to clarify that in the event of FICC's
default, novation is deemed to have occurred with respect to all
transactions at the time such transactions are compared, whether or not
such transactions are SBO-Destined Trades that would otherwise have
been novated at comparison. The other changes to this provision are
grammatical corrections.
2. Statutory Basis
    The proposed rule changes are consistent with the requirements of
Section 17A(b)(3)(F) of the Securities Exchange Act of 1934, as amended
(the ``Act''), and the rules and regulations thereunder, because by
moving novation for trades that enter GSD's Netting system and MBSD's
TBA Netting system, they clarify FICC's responsibilities to its members
and remove potential uncertainty that previously existed due to a
mismatch between the time of guaranty and the time of novation. Such
clarity facilitates the prompt and accurate clearance and settlement of
securities transactions and assures the safeguarding of securities and
funds which are in the custody or control of FICC or for which it is
responsible.
    As noted above, FICC guarantees (and is therefore responsible for)
the settlement of trades upon comparison. Nonetheless, currently FICC
does not become the members' legal counterparty with respect to
compared trades until the relevant netting output is issued to such
members (usually the day before settlement). FICC understands that as
members (or their advisors) analyze member netting rights with respect
to transactions cleared through FICC for purposes of regulatory capital
requirements, it is beneficial for members that FICC become the legal
counterparty at the point its guarantee attaches.

B. Clearing Agency's Statement on Burden on Competition

    FICC does not believe that the proposed rule change will have any
impact, or impose any burden, on competition that is not necessary or
appropriate. The proposed changes will apply to eligible transactions
that are submitted to GSD's Netting system and MBSD's TBA Netting
system.

C. Clearing Agency's Statement on Comments on the Proposed Rule Change
Received From Members, Participants, or Others

    Written comments relating to the proposed rule changes have not yet
been solicited or received. FICC will notify the Commission of any
written comments received by FICC.

III. Date of Effectiveness of the Proposed Rule Change and Timing for
Commission Action

    Within 45 days of the date of publication of this notice in the
Federal Register or within such longer period up to 90 days (i) as the
Commission may designate if it finds such longer period to be
appropriate and publishes its reasons for so finding or (ii) as to
which the self-regulatory organization consents, the Commission will:
    (A) By order approve or disapprove such proposed rule change, or
    (B) institute proceedings to determine whether the proposed rule
change should be disapproved.
    The proposal shall not take effect until all regulatory actions
required with respect to the proposal are completed.

IV. Solicitation of Comments

    Interested persons are invited to submit written data, views and
arguments concerning the foregoing, including whether the proposed rule
change is consistent with the Act. Comments may be submitted by any of
the following methods:

Electronic Comments

     Use the Commission's Internet comment form (http://www.sec.gov/rules/sro.shtml), or
     Send an email to<EMAIL_ADDRESS>Please include File
Number SR-FICC-2014-11 on the subject line.

Paper Comments

     Send paper comments in triplicate to Secretary, Securities
and Exchange Commission, 100 F Street NE., Washington, DC 20549.

All submissions should refer to File Number SR-FICC-2014-11. This file
number should be included on the subject line if email is used. To help
the Commission process and review your comments more efficiently,
please use only one method. The Commission will post all comments on
the Commission's Internet Web site (http://www.sec.gov/rules/sro.shtml). Copies of the submission, all subsequent amendments, all
written statements with respect to the proposed rule change that are
filed with the Commission, and all written communications relating to
the proposed rule change between the Commission and any person, other
than those that may be withheld from the public in accordance with the
provisions of 5 U.S.C. 552, will be available for Web site viewing and
copying in the Commission's Public Reference Room, 100 F Street NE.,
Washington, DC 20549 on official business days between the hours of
10:00 a.m. and 3:00 p.m. Copies of the filing also will be available
for inspection and copying at the principal office of FICC and on its
Web site at http://www.dtcc.com/~/media/Files/Downloads/legal/rule-
filings/2014/ficc/SR-FICC-2014-11.pdf. All comments received will be
posted without change; the Commission does not edit personal
identifying information from submissions. You should submit only
information that you wish to make available publicly. All submissions
should refer to File Number SR-FICC-2014-11 and should be submitted on
or before January 6, 2015.

    For the Commission, by the Division of Trading and Markets,
pursuant to delegated authority.\15\
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    \15\ 17 CFR 200.30-3(a)(12).
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Kevin M. O'Neill,
Deputy Secretary.
[FR Doc. 2014-29361 Filed 12-15-14; 8:45 am]
BILLING CODE 8011-01-P


Telomer Research Program Annual Report of Activities for TRP Grant to University of Toronto; Scott Mabury, PI Project years: 1 September, 2001 to 1 September, 2002.

Students/ PostDocs currently active on the FTOH project: Postdocs: Dr. David Ellis, Dr. Jon Martin, Dr. Stella Melo, Grad students: Naomi Stock, Ella Ye, Undergrad Studens: Kerry Pratt, Fiona Lau, Ryan Sullivan, and Lisa Deeleebeck. Note: TRP funds support the research of Dr. David Ellis while other funds support the rest of the team.

Academic Co Investigators: Derek Muir ( NWRI), Keith Solomon and Paul Sibley ( UofGuelph), Kim Strong ( Toronto Physics), Tim Burrow ( Toronto; Chemistry; NMR Facility), Ying Lei ( Toronto; Chemistry; ANALEST).

Project Coordination: During the initial year of the project the UofT research team hosted TRP visits in Fall, 2001 ( Libre, Hoke, Buck, Kaiser) for a general research progress, a priorities setting exercise, Winter, 2002 ( Kaiser and Gearhart) for familiarization with our analytical techniques for FTOH air sampling/ analyses and a late spring 2002 ` update' meeting with Libre, Hoke, and Buck. Further there were at least 2 conference calls concerning air sampling and vapour pressure measurements that transpired during this period. A number of visits prior to Sept, 2001 also occurred both in Toronto and Guelph to explore research interests and analytical techniques.

Status of NSERC. Strategic Matching Funds: A proposal was submitted in mid April to NSERC to pursue additional funds for our FTOH work. This proposal has Mabury as PI and Muir, Sibley, and Solomon as Co Investigators. Notification of success in this grant cycle will likely be in November.

Specific Objectives for TRP funds for Year 1 ( from the research agreement appendix): Based on the October 26, 2001 meeting that included the Mabury ( Toronto), Muir ( NWRI) and Sibley ( Guelph) and Hoke, Buck, and Kaiser ( Dupont) and Libre ( Atofina) the specific work to be continued and expanded for the TRP funded portion of this project is to focus in year 1 on three specific areas and include the following: 1) analytical methodologies; 2) environmental monitoring and 3) environmental fate determination. Analytical methods will directly focus on further optimizing our sampling and GC based analysis techniques of fluoro telomer alcohols primarily in air samples and developing the basic methods utilizing lc/ ms/ ms to determine our hypothesized degradation products which are the telomer acids. Environmental monitoring will comprise air sampling at Toronto in an ongoing campaign and an intensive air sampling at selected locations across North America. Initial samples for telomer degradation products will also be run focusing on atmospheric particles and municipal outfalls. Our main objectives in the environmental fate area are to determine degradation pathways and kinetic rates for atmospheric pathways and further refine our physical property measurements.

Good progress has been made in each of these areas and is reported below. A large air sampling study ( FAMAS) conducted last November and an arctic sampling expedition this July, smog chamber experiments, initial experiments investigating biodegradation pathways, and further experiments focusing on physical property measurements of FTOHs and polyfluorinated alkyl chains, have taken up the bulk of effort during our inaugural year of TRP funding.

Environmental Monitoring 1. Fluorinated Telomer Alcohols in the North American Atmosphere ( Stock, Martin, Lau) The presence of fluorinated telomer alcohols and other fluorinated compounds in the North American atmosphere was investigated using high volume air samplers. In November 2001, samples were collected in six cities throughout North America, which were chosen as remote locations or for nearby presence of industrial sources ( Winnipeg MB, Long Point ON, Reno NV, Cleves OH, Toronto ON, and Griffin GA). This study was given the acronym " FAMAS" for fluoroalcohol monitoring in air samples. Both gaseous and particulate bound fluoroorganics were collected on media consisting of XAD 2, polyurethane foam and quartz fiber filters. All samples were approximately 1000 m3. Due to the potential for contamination all sample preparations and subsequent extractions were conducted in Class 100 clean room conditions. Briefly, these samples were extracted in large custom, glass columns by soaking in methanol and five aliquots of ethyl acetate. The aliquots were combined and an internal standard was added. The samples were rotovapped to ~ 5 mL, filtered using a nylon 0.2 µ m filter and subsequently reduced to ~ 200 µ L under pure nitrogen. Blank extraction samples were also run. Samples were separated using gas chromatography ( either 30 or 60 m DB 35 column with 5 micron film) and detected using chemical ionization mass spectrometry ( GC/ CI MS) ( quadrupole instrument). Several fluorinated compounds  including fluorotelomer alcohols and perfluoro sulfonamides  were detected at pg/ m3 concentrations in all locations ( Table 1). Low concentrations of fluoroorganics were consistently detected in field blanks; however, this did not prevent confirmation or quantification of environmental concentrations. As the sample extraction method lacked an adequate clean up step, chromatography difficulties were unavoidable. This proved especially true for the 10: 2 FTOH where adequate chromatography was not achieved and thus no quantitative data are reported. Currently, a clean up step is under development and samples will be cleaned up and re analyzed. In addition, the samples will also be analyzed via gas chromatography coupled with tandem mass spectrometry ( GC/ MS/ MS) ( iontrap instrumentation). We believe this will provide a more robust analytical technique with the added value of MS/ MS spectra for enhanced identification. Table 1. Concentration of fluorotelomer alcohols ( FTOHs) and perfluorooctane sulfonamidoethanols ( FOSEs) in North American air samples.

SAMPLE LOCATION 6: 2 FTOH ( µ g/ m3) 8: 2 FTOH ( µ g/ m3) NEtFOSE ( µ g/ m3) NMeFOSE ( µ g/ m3) Cleves, OH 72 ± 48 79 ± 35 11 ± 10 18 ± 5 Griffin, GA   127 ± 71 40 ± 7 371 ± 309 Long Point, ON 16 ± 5 21 ± 12 6 ± 4 10 ± 4 Reno, NV 51 ± 9 50 ± 7 506 ± 217 152 ± 48 Toronto, ON 62 ± 28 25 ± 22 38 ± 46 31 ± 4 Winnipeg, MB 26 ± 24 18 ± 3 27 ± 6 64 ± 18   chromatography difficulties 2. Fluorinated Telomer Alcohols in the Lake Ontario Ecosystem ( Stock) In June 2002, Naomi Stock ( PhD student) participated in a 5 day research cruise, aboard the CGCS Limnos, of Lake Ontario. At each of three stations, water, sediment, zooplankton and phytoplankton samples were collected. Air samples, using high volume air samplers and polyurethane foam/ XAD 2 sampling media ( as previously described), were also collected for the duration of the cruise. Currently, methods are being developed to analyze these samples for a suite of fluorinated compounds including the fluorinated telomer alcohols and possible degradation products. Briefly, air samples will be extracted and analyzed via gas chromatography coupled with mass spectrometry as previously described. Water samples will be concentrated onto XAD 7, extracted using a method similar to that employed for air samples and analyzed via liquid chromatography coupled with tandem mass spectrometry. Sediment and biota samples will be extracted using an ion pairing agent and also analyzed via liquid chromatography coupled with tandem mass spectrometry.

3. FTOHs in the Arctic? ( Martin, Stock) Using additional funding provided by the Northern Contaminants Progam ( NCP), Drs. Martin and Mabury traveled to Kuujjuarapik ( Quebec) between the dates of July 11th and 17th, 2002, for collection of multiple environmental samples. Kuujjuarapik is located at the mouth of the Great Whale river on the eastern shore of Hudson Bay, just north of James Bay. This location is subarctic, and was chosen primarily because it is an intermediate distance between the high population density of the Great Lakes region and the Canadian Arctic. The University of Laval also has a research center at this location ( Centre D'Etudes Nordiques) which provided us with boats and other necessary sampling equipment.

To test the hypothesis that telomer alcohols ( and 3M sulfonamidoethanols) can be transported to remote regions, an air sampler was installed in Kuujjuarapik to collect air samples by the same method as Martin et al.. To date we have collected only two samples, along with a field blank, but the sampler is still installed and we hope to take continuous samples if any telomer alcohols are detected in the existing samples that have yet to be extracted and analyzed. It is expected that air sample data will complement the smog chamber work, allowing for a better understanding of the long range transport potential for telomer alcohols.

Water and biota samples were also collected for the purposes of our NCP project ( Table 2) ( i. e. analysis of perfluorinated acids) but will also be analyzed for fluorinated neutrals ( including telomer alcohols) when appropriate methods have been developed for extraction and analysis of tissues. Water samples ( 40 L) were collected in Hudson Bay and in the Great Whale River by pumping water through XAD columns in the field. Sampled biota included phytoplankton, zooplankton, and fish. Even if air samples reveal no traces of fluorinated neutrals ( i. e. due to detection limits), biota may reveal traces because of the predictably high bioaccumulation potential for the longer chained telomer alcohols.

Table 2. Biotic and abiotic samples collected in Kuujjuarapik, Quebec.

Sample Details Status Kuujjuarapik Air 2 samples, 1 blank Cold Storage Hudson Bay Water 3 samples ( 40 L each) Cold storage Great Whale River Water 1 sample ( 40 L), 1 blank Cold storage Fish Livers Pike ( 1), Whitefish ( 2), Suckers ( 3), sculpin ( 2), Trout ( 1). Frozen Hudson Bay Phytoplankton 500 grams frozen Fresh Water Zooplankton 3 locations Mixed Copepods, chironomids, cladocera, diptera, rotifera, calanoida. frozen Physical Properties 4. Vapour Pressure by the GC method ( Le). The GC retention time method by Bidleman ( 1981) was chosen, because it allows the relatively rapid determination of the temperature dependent vapor pressure of a large number of compounds. Small quantities of the substances are sufficient, and a very high purity is not required. Based on a comprehensive review Delle Site ( 1997) concluded that this method " can be recommended as one of the most suitable [ methods] for the determination of the vapor pressure of low volatility compounds." Another recent study concluded that capillary GC is capable of providing vapor pressure data for non polar and slightly polar compounds with relative errors that " are either comparable with or lower than those resulting from more cumbersome direct experimental techniques" ( Svoboda and Koutek, 2002). The method's success and reliability however is dependent on the availability of high quality vapor pressure data for some related compounds to serve as standard reference and calibration compounds.

Isothermal gas chromatographic retention times at six temperatures within the range 30 to 80 ° C were determined. Super cooled liquid vapor pressures PL were obtained from these retention times following the procedure described by Bidleman ( 1981) and Hinckley et al. ( 1990). Specifically, for each analyte a vapor pressure PGC at 25 ° C was calculated using:

ln ( PGC/ Pa) = (  VAPH /   VAPHref) · ln ( PLref/ Pa) + C ( 1)

where PLref and   VAPHref refer to the well established liquid phase vapor pressure at 25 ° C and the enthalpy of vaporization of a standard reference compound. The enthalpies of vaporization are assumed to be constant over the temperature range from 25 ° C to the temperatures of the GC retention time measurements. The enthalpy ratio ratio   VAPH /   VAPHre and the constant C in eq ( 1) were obtained by linearly regressing the logarithm of the ratios of the measured isothermal GC retention times tR/ tRref at each temperature against the logarithm of the vapor pressure of the reference compound at that temperature using the relation ( Bidleman, 1981),

ln ( tR/ tRref) = [ 1(  VAPH /   VAPHref)] ln ( PLref/ Pa)  C ( 2)

Eq 2 assumes that the infinite dilution activity coefficients in the stationary phase are the same for both the analyte and the reference compound ( Hinckley et al., 1991). As this is an approximation, PGC is not always identical to the vapor pressure of the ( super cooled) liquid PL, and a calibration of the method with closely related compounds is advisable ( Bidleman, 1981, Hinckley et al., 1990). In the current study, hexachlorobenzene served as the standard reference compound. For the calibration we employed the following compounds with well established vapor pressure at 25 ° C: 1,2 dichlorobenzene, 1,3 dichlorobenzene, 1,4 dichlorobenzene, 1,2,3 trichlorobenzene, 1,2,4 trichlorobenzene, 1,3,5 trichlorobenzene, 1,2,3,4 tetrachlorobenzene, 1,2,3,5 tetrachlorobenzene, 1,2,4,5 tetrachlorobenzene, pentachlorobenzene, Pentafluorotoluene, Pentafluorophenol, TCTFB, Octafluorophthalene, decafluorobiphenyl,   HCH,   HCH,   HCH, Aldrin, Heptachlor, Dieldrin, p, p' DDE, o, p' DDT, p, p' DDT.

Table 3. Vapour pressure values for FTOHs obtained using the GC retention time method.

Log PGC PGC log PL PL PL PL 250C mean mean mean mean stdev RSD 4: 2 FTOH 2.401 252 3.18 1514.4 321.4 21%

6: 2 FTOH 2.161 145.2 2.90 801.7 149.0 19%

8: 2 FTOH 1.662 45.90 2.33 212 34 16%

10: 2 FTOH 1.123 13.27 1.70 50 7 13%

5) Measurement of Vapor Pressure by Boiling Point Method ( Deeleebeck, Ellis)

The vapor pressure ( Vp) of the liquids 4: 2, 6: 2, 8: 2 and 10: 2 telomer alcohols were measured using the boiling point method. This method involved a 25 mL round bottom flask connected to a miniature thermometry adapter and condenser; 15 mL of the analyte was added to the round bottom flask. In the case of fluorinated materials, they were first de gased by a procedure which involved cooling the mother liquor to  198 ° C Table 4. Test Chemicals, Vp ( Pa)

( liquid N2) followed by warming to room temperature while a vacuum was maintained at ~ 15 mmHg. Following this the pressure of the system was reduced appropriately and allowed to equilibrate. The analyte was then brought to its boiling point and the temperature and pressure recorded. This procedure was repeated for decreasing values of pressure, which were achieved by removing the air from the apparatus with a vacuum pump. To determine the vapor pressure at 25 degrees centigrade, the natural log ( ln) of pressure in Pascal's was plotted against the temperature in Kelvin. The best linear fit to Compound Experimental Literature difference Cyclohexane 15720 +/ 3 13370 18% Toluene 6400 +/ 200 4910 30% m Xylene 2900 +/ 100 2250 29% the data points was used to extrapolate the boiling point of the chemical at 298 K, the vapor pressure at room temperature. The method was first calibrated using cyclohexane, m xylene, and toluene and the vapor pressures measured were compared with typical literature values ( n = 3, Table 4). The same method was then applied to the telomer alcohols, the results are presented in Table 5 ( n= 3). The telomer Vp's were compared with literature values for the corresponding hydrogenated versions, i. e. fluorine replaced with hydrogen. The increase in Vp associated with the incorporation of fluorine is seen clearly in Figure 1. The rate of decrease in Vp for the telomers as a function of increase in mass is much slower than would normally be expected when compared with their hydrocarbon counterparts, resulting in the vapor pressure of the 8: 2 being similar to that of octanol ( Figure 2).

Table 5. Telomers, Vp ( Pa)

6. Measurement of chain rigidity of perfluorinated fluorinated compounds by NMR ( Pratt, Ellis, & Burrow)

The physical properties, such as vapor pressure or Kow, of fluorinated molecules will be determined, to some degree, by the internal molecular geometry of the molecule. 7 7.5 8 8.5 9 9.5 10 10.5 11 11.5 12 300 400 500 Temperature ( K) Ln pressure ( Pa)

fluorinated non fluorinated CX3( CX2) NCH2CH2OH X= F X= H N= 9 N= 3 Figure 1. Change in vapor as a function of temperature 0 2 4 6 8 10 12  50 150 350 550 Mass ( grams/ mol) Ln pressure ( Pa)

Alcohols Telomers Figure 2. Change in Vapor Pressure a function of mass. Compound Run 1 Run 2 Run 3 Average Std. Dev. 4: 2 998 1022 956 990 30 6: 2 784 663 692 710 60 8: 2 247.7 247.7 272.1 250 20 10: 2 138.00 138.2 156.8 140 10 Interaction of the fluorine nuclei result in 19F NMR coupling constants. The magnitude of these coupling constants is a function of the torsional angle between adjacent C   F moieties. The amount of energy required to allow free rotation between two adjacent C   F units is proportional to the " stiffness" of the alkyl chain, which in turn is related to the Vp of the molecule. 1D 19NMR is inadequate in the determination of long range coupling constant in perfluoroalkyl chains due to spectral overlap. We have developed a 2D Jresolved experiment that facilitates these measurements for which an example is shown for perfluorobutanoic acid in Figures 3a & b.

Figure 3. A) 1D 19F NMR for perfluorobutanoic acid with spectral overlap and B) 2D J resolved NMR now showing coupling constants for all fluorine atoms.

This method allowed for the assignment of all fluorine coupling constants and furthermore indicted that at room temperature perfluorobutanoic and longer chain acids have a rigid back bone structure between the CF2 units, with free rotation allowed around the CF3   CF2 bond. This molecular rigidity facilitates interpretation of the underlying origins of the high Vp of polyfluorinated materials seen our vapour pressure measurements. The enthalpy of free rotation of the carbon backbone of the acid was established using variable temperature NMR. A comparison between the effect of chain length and the amount of energy required for free rotation was made. Figure 4 shows a temperature dependent plot of the 1D NMR for the CF3 group and two identical CF2 groups for the perfluoro  octanoic and  butanoic acids. The coalescence point for butanoic acid is seen at 60 º C while it is 90 º C for the octanoic acid. This indicates that a perfluorochain becomes energetically more rigid as a function of chain length and is thus less easily distorted. The results assist in explaining the minimal change in vapor pressure as chain length increases. Hz  10  5 0 5 10 15 Hz  15  5 0 5 10 20 Hz  4  2 0 1 2 3 4 5 ppm  118.64  118.60 ppm  80.33  80.30 ppm  126.842  126.834 CF3 CF3 A) CF2 CF2 CF2 CF2 B) Figure 4. Temperature dependent 19F NMR for perfluorobutanoic and octanoic acids 7. Global Warming Potentials of Fluorinated Telomer Alcohols ( Stock & Melo) In collaboration with Prof. Kim Strong ( Department of Physics, University of Toronto), Dr. Stella Melo ( Postdoctoral Fellow) and David Barclay ( undergraduate student), our research group is in the process of measuring the absorption cross sections of the 4: 2, 6: 2, 8: 2 and 10: 2 FTOHs. These cross section measurements are obtained in the infrared atmospheric window at a range of temperatures and pressures. Once the absorption cross section measurements are complete we can calculate the radiative forcing for this polyfluorinated mateirals, and ultimately calculate a global warming potential of each fluorinated telomer alcohol once we have the accurate lifetime data from our smog chamber studies ( see below). It is not expected that the FTOHs will have high GWP but they may have extremely high radiative forcing values due to the large number of C F bonds ( e. g. 21 in 10: 2 FTOH). ppm  126.6  126.5  126.4  126.3  126.2  126.1 ppm  118.5  118.4  118.3  118.2  118.1  118.0 ppm  80.25  80.20  80.15  80.10  80.05 Temperature ( º C)

100 90 80 70 60 50 40 30 ppm  125.7  125.5  125.3  125.1 ppm  117.5  117.4  117.3  117.2  117.1  117.0 ppm  80.25  80.20  80.15  80.10  80.05 Temperature ( º C)

100 90 80 70 60 50 40 30 Perfluorooctanoic Acid CF Perfluorobutanoic Acid 3 CF2 CF2 Analytical Methodologies 8) Synthesis of isotopically labeled internal standards ( Ellis & Sullivan)

The synthesis of an isotopically labeled 6: 2 aldehyde ( M + 2 molecular ion) has been conducted and will be converted to the 6: 2 alcohol ( M + 3) according the scheme outlined in Figure 5 for use as internal standards in the analysis of these and related chemicals.

Figure 5. Synthesis of labeled 6: 2 aldehyde and alcohols.

9) Mass Spectroscopic Studies of Telomer Alcohols and Products ( Ellis)

A systematic mass spectrometry study of the telomer alcohols along with their oxidized products, saturated and  ,    unsaturated fluoroacids, was conducted using negative and positive chemical ionization ( NCI and PCI). The compounds investigated are shown in Table 6.

Table 6. Chemical I. D. and acronymns for the telomer based chemicals used in the MS study. Telomer Alcohols Telomer Acids Telomer    Unsaturated Acids n = 2 ( 4: 2)* n = 2 ( 4: 2A) n = 2 ( 4: 2UA) n = 4 ( 6: 2) n = 4 ( 6: 2A) n = 4 ( 6: 2UA) n = 6 ( 8: 2) n = 6 ( 8: 2A) n = 6 ( 8: 2UA) n = 8 ( 10: 2) n = 8 ( 10: 2A) n = 8 ( 10: 2UA) * Acronyms are given for each in parenthesis. CF3( CF2) 5I + 13CH2 13CHOC( O) CH3 AIBN CF3( CF2) 5 13CH2 13CHIOC( O) CH3 CF3( CF2) 5 13CH2 13CHO ( 6: 2 Aldehyde) H3O+

NaBD4 CF3( CF2) 5 13CH2 13CDHOH ( 6: 2 Alcohol)

CF3( CF2) nCF2CH2CH2OH CF3( CF2) nCF2CH2C( O) OH CF3( CF2) nCFCHC( O) OH In the case of the fluoroalcohols, NCI resulted in the production of more elaborate spectra than the other classes. Moreover, it showed the interesting production of HF2  and the complexation of this species with the parent molecule ( Figure 6).

Figure 6. NCI mass spectrum for the 6: 2 alcohol showing the production of HF2

Alteration of the functional group attached to fluoroalkyl moiety had a large impact upon the fragmentation channels, which were identified ( see, for example, Figures 12a and b) and also on the magnitude of fragment produced.

Figure 7. a) Hypothesized fragmentation pattern for the 6: 2 telomer alcohol in NCI mode and, b) fragmentation pattern for the 6: 2 telomer acid. a) b)

CHCO O m/ z 357  FCO2 CH m/ z 294  HF m/ z 274 C E Isomer Z Isomer CCO O m/ z 318  F CHCO O  HF m/ z 338  CO2 CF3( CF2) 2CF2CF2CF CF3( CF2) 2CFCF2CF CF3( CF2) 2CFCF2C CF3( CF2) 2CFCF2C CF3( CF2) 2CFCF2CF O m/ z 377 CF3( CF2) 2CF2CF2CH2CO  HF O m/ z 378 CF3( CF2) 2CF2CF2CH2COH  H m/ z 364 CF3( CF2) 4CF2CH2CH2OH . F CF3( CF2) 4CF2CH2CH2OH . HF2 m/ z 383 m/ z 403 + F  H CF3( CF2) 4CF2CH2CH2O + HF2 CF3( CF2) 4CF2CH2CH2OH m/ z 363 m/ z 323  F C8F11H2O C8F10H2O m/ z 304  HF C8F9HO m/ z 284  HF Pressure Dependant Channel  CO C7F9H m/ z 256 C8F8O m/ z 264  CO C7F8 m/ z 236 m/ z 294  HF C7F10H4O C7F9H3O m/ z 274  CO C6F9H3 m/ z 246  CF3  2HF Although the exact structure of these intermediates requires further investigation, other researchers, in the case of hydrofluorocarbons, have invoked a six membered back bonding transition state between the hydrocarbon portion of the chain and the fluorocarbon portion to support the sequential loss of HF in similar systems ( Napoli et. al.). Previous x ray crystallographic studies suggest that the perfluoro portion of the molecular chain adopts a ridged zigzag geometry with the end hydrocarbon segment of the chain folding back on top of that fluorinated portion ( Wang and Ober, Erkoc and Erkoc). It has also been shown that there is evidence for the cleavage of the CF2   CH2 bond within the molecule suggesting there is unusually high stability of this bond which could be explained by a H F bridging interaction.

Such intramolecular interaction in the case of telomer alcohols in the liquid phase is supported by the studies conducted by Von Werner and Wrackmeyer. They showed that fluorination in the   position to a CH2OH group had a marked effect on the 13C NMR chemical shift while having little effect upon the   CH2, an effect which has been assigned to the hyperconjugative interaction of the lone pair of electrons of the fluorine at that carbon. In later studies Von Werner and Wrackmeyer also employed 17O NMR and showed that electron density at the oxygen is increased as observed through the oxygen shielding effect. This strongly suggests that the terminal ethanolic group is closely associated with the fluorocarbon potion of the molecule. We believe it is this association, and with it changes in electron density distributions, that lead to the favoured complexations of F and HF2 . Futhermore, this association would not occur in the case of CF3CH2CH2OH and thus this molecule would exhibit differences in it physical and reactive properties relative to the Telomer alcohols.

Detailed analysis and comparisons of the mass spectral data obtained collectively from all analytes allowed certain conclusions to be drawn concerning their thermodynamic physical properties and from this hypotheses can be made toward environmental fate. For example, the unique geometries associated with the compounds and the resultant effect this imparts upon the physical properties may lead to novel and interesting chemistries in the atmospheric gas phase. For example, these results suggest that the telomer alcohols may have a close association, an association that one would not expect for alcohols, with tropospheric charged species and/ or polar species as evidenced from their universal association with F and HF2 . Complexation with gas phase species such as sulphate, or even with non charged polar molecules such as water vapor, may effect their dissemination. Atmospheric lifetimes, for example reaction rates with tropospheric cleansing reagents such as hydroxy radicals may also be effected by such complexations, allowing longer range transport.

It would appear from the fragmentation that occurs that the lowest energy pathway for the degradation of the alcohols, either biotically or abiotically, would result in the production of stable polyflourometabolites, which in turn might be expected to be environmentally persistent. From these results, it can be postulated that the electron density distribution associated with such unique structural geometries will impact physical properties such as vapor pressures, ( e. g. vapor pressures will be greater than expected from linear predictions based upon the molecules size and functional groups) which is indeed experimentally observed to be the case. The unique differences in geometry of these molecules is also expected to influence physical properties of the molecules such as Kow and hence bioaccumulation. This postulation is supported by the recent observation that bioaccumulation potential increases ten fold for every additional CF2 unit within the alkyl chain for perfluoroacids ( Martin et al).

Fate Pathways 10) Atmospheric Degradation Processes ( Ellis & Martin)

The telomer alcohols are proposed to degrade in the atmosphere following a mechanism outlined in Figure 8.

Figure 8. Proposed atmospheric degradation of Telomer alcohols, 6: 2 alcohol is used as an illustrative example. F F F F F F F F F F CH2CH2OH F F F F F F F F F F F F F CH2 F F F C O OH F F F F F F F F F F CH2CHOH F F F F F F F F F F F F F CH2 F F F C O H F F F F F F F F C F F F C O H H F C°

F F F F F F F F C F F F C O H H F OH C F F F F F F F F C F F F C O H H F OH O O° C F F F F F F F F C F F F C O H H F OH O° C F F F F F F F F ° C F F F C O H H OH O F C F F F F F F F F F F F O OH F F F F F F F F F F CH2°

F F F F F F F F F F F F F CH2 F F F C° O F F F F F F F F F F CH2OO°

F F F F F F F F F F F F F CH2O°

F F F F F F F F F F F F F C F F F O H F F F F F F F F F F CH2 F F F COO° O F F F F F F F F F F CH2 F F F CO° O C ° F F F F F F F F F F OH O2 NO NOT OBSERVED 6: 2 FTOH Tropospheric Reactions; Possibilities OH h  F F F UnZips 6:: 2 Ald PFHxA OH O2 H2O/ particles loss of HF OH O2 NO H2O h  OH O2 NO O2 O2 NO Note: ? whether this is an artifact pathway. °

Cavalli et al, 2002, ES& T 36: 1263 1270 Mashimi et al, 2000. J. Phys. Chem A, 104: 7255 7260; Vesine et al, 2000. J. Phys. Chem A, 104: 8512 8520. Vesine et al, 2000. J. Phys. Chem A, 104: 8512 8520. This hypothesis was tested using a 10m3 artificial atmospheric smog chamber. The 6: 2 alcohol was introduced to the system along with cyclohexane ( a reference compound), NO gas, and isopropylnitrite ( an indirect source of OH). The system was irradiated using black lights and sample aliquots were taken and analyzed as a function of time. Real time NOx and O3 concentrations were monitored in order to eliminate possible secondary loss reactions. Samples were collected in real time by SPME and analyzed using GC/ MS. Samples were also taken using XAD and Na2CO3 denuders, low temperature gas phase condensation bubblers, and by passing gas samples through DNPH SPE cartridges for further analysis. Continuous air flow from the chamber was passed through nylon and XAD coated filters which were collected and analyzed for particulate formation. Post chamber analyses were conducted using 19F NMR, LC/ MS/ MS and GC/ MS. The telomer alcohol does not undergo photolysis at the wavelengths of light used and it does not undergo significant wall reactions, or with NOx and O3 under the conditions used. The gas phase condensate obtained from the smog chamber at low temperature ( 78 ° C) by bubbling the air through acetone was analyzed directly using 19F NMR. The resultant spectra, acquired over a 24 hour period clearly indicated the presence of the 6: 2 alcohol and a second fluorinated species that we have tentatively assigned as fluoride. No other fluorinated intermediates were observed, possibly due to the low concentrations of fluorinated intermediates coupled with the low sensitivity of the NMR experiment. GC/ MS analysis of samples acquired by passing smog chamber air through an XAD bed have thus far only indicated the presence of starting material. Due to the volatility of the proposed intermediates it was recognized this may be result of poor trapping efficiency. Larger volumes of air have been passed icwe pre coated XAD denuders that have a greater capacity for such materials. These samples are currently being analyzed.

The pseudo first order kinetics for the reaction of the 6: 2 telomer with OH relative to cyclohexane is shown in Figure 9.

Figure 9. Relative rates of reaction for cyclohexane with 6: 2 telomer OH Degradation of 6: 2 Telomer y = 0. 4006x + 0.0237 R2 = 0.981 0 0.05 0.1 0.15 0.2 0.25 0.3 0.35 0.4 0 0.2 0.4 0.6 0.8 1 ln([ Cyclohex ane] t0/[ Cyclohexane] t) ln([ Telomer] t0/[ Telomer] t) Using a rate constant of 7.49 x10 12 molecule cm3 s 1 at 298K for the reaction of OH with cyclohexane resulted in a calculated rate constant for the 6: 2 telomer alcohol of 2.8 ± 0.1 molecule cm3 s 1 ( n= 2). The reported literature value for the OH initiated degradation of butanol is 8.24 ± 0.84 x10 12 molecule cm3 s 1 which is as expected greater than the measured value for the 6: 2 telomer alcohol due to the effect of fluorination. However, this rate is greater than would be predicted using the Kwok and Atkinson method of prediction. We believe that this is a result of secondary, through space interaction of the ethanolic substituent with the fluorinated tail of the molecule, a hypothesis that is supported by MS data obtained ( details of which are presented in above) and from the literature dealing with similar compounds. The product perfluorohexanoic acid was positively identified ( n= 3) by LC/ MS/ MS ( Figure 10) and is currently being quantified relative to the starting material ~ it does not appear to be the major route for degradation. Overall we have had significant difficulties in isolating and identifying the bulk of the FTOH degradation products. For instance we've only obtained sporadic evidence for the initial aldehyde via GC/ MS and we do observe fluoride in some samples. These results may indeed indicate that the ` unzipping' route is the dominate fate pathway for the FTOHs ( see Fig 8). A good deal of further work must be done obtaining a mass balance of products and confirming the degradation pathway.

Figure 10. LC/ MS/ MS indicating the production of perfluorohexanoic Acid The proposed intermediate aldehyde and acids ( Section 5) that potentially lead to the formation of perfluorohexanoic and longer chain acids ( Figure 5) were synthesized by the methods outlined in Figure 8 for the use as standards for the identification of these intermediates. 0.00 0.25 0.50 0.75 1.00 1.25 1.50 1.75 2.00 2.25 2.50 2.75 3.00 Time 0 100 % cmII84k Sm ( Mn, 2x3) MRM of 15 Channels ES 313 > 269 1.07e3 0.82 PFHxA Figure 11. Synthesis of fluoro aldehyde and acid standards.

A further interesting observation is that 1H, 1H, 2H, 2H perfluorodecyliodide, which is an impurity contained within the manufactured 6: 2 telomer, is not observed to degrade under these conditions, thus indicating greatly reduced reactivity with OH and ultimately a much longer tropospheric lifetime.

11) Biodegradation of FTOHs ( Ye & Dinglasan)

Range finding experiments have been initiated on the suite of FTOHs with initial experiments focused on the fate of the 6: 2 FTOH in a mixed culture of microbes. Mixed enrichment aerobic degrading cultures were obtained from a 1, 2 DCA site in LA, U. S. and subsequently maintained on either 1,2 DCA or ethanol. Two isolates have been identified to date from this mixed culture ~ a Ralstonia sp. and a Xanthobacter sp.. These experiments have clearly shown that the 6: 2 fluorotelomer alcohol is efficiently oxidized to the 6: 2 telomer acid ( see Fig 12) which then either hydrolyzes or further metabolizes to the 6: 2  ,   acid. Low but clearly measurable quantities of the perfluoroacid PFHxA are observed to build up in the reaction vessels. Work currently is focused on optimizing analytical methods to monitor all compounds of interest during the biodegradation experiment with particular focus on observing the relevant intermediates ( e. g. the 6: 2 aldehyde which has been synthesized). To accurately determine the reaction pathway subsequent experiments will dose the microbial media with the 6: 2 aldehyde, acid, alpha beta acid, and PFHxA in order to obtain rates and pathway information on each. We will then compare the relative suscepbilities of the 4: 2 through 10: 2 FTOHs and confirm whether the degradation pathway is similar across the varied chain length. CF3( CF2) nCH2COH O CF3( CF2) nCH2CH2OH ( n = 3, 5, 7, 9) CrO3/ H2SO4 CF3( CF2) nCH2COH O NaOH ( aq) THF ( n = 3, 5, 7, 9) CF3( CF2) n 1CF CHCOH O CF3( CF2) 5CH2CH O CF3( CF2) 5CH2CH2OH CF3( CF2) 4CF CHCH O PCC Dess Martin CH2CCl2 CH2CCl2 CF3( CF2) 5CH2CH2OH Figure 12. Proposed biodegradation pathway of 6: 2 FTOH with intermediates so far confirmed by LC/ MS/ MS. We are unclear specifically where PFHxA arises but it appears to follow the build up slowly after high concentrations of the 6: 2  ,   acid are formed.

References Bidleman, T. F. Estimation of Vapour Pressures for Nonpolar Organic Compounds by Capillary Gas Chromatography. Anal. Chem. 1984, 56, 2490 2496.

Delle Site, A. The Vapor Pressure of Environmentally Significant Organic Chemicals: A Review of Methods and Data at Ambient Temperature. J. Phys. Chem. Ref. Data 1997, 26, 157 193.

Erkoc S and Erkoc F. J. Mol. Struc Theochem. 2001; 549: 289.

Hinckley, D. A.; Bidleman, T. F.; Foreman, W. T.; Tuschall, J. R. Determination of Vapor Pressures for Nonpolar and Semipolar Organic Compounds from Gas Chromatographic Retention Data. J. Chem. Eng. Data 1990, 35, 232 237. F F F F F F F F F F CH2CH2OH F F F F F F F F F F F F F CH2 F F F C O H F F F F F F F F F F CH2 F F F C O OH C F F F F F F F F C F F F C O OH H F C F F F F F F F F F F F 6: 2  ,   6: 2 FTOH 6: 2 Aldehyde 6: 2 Acid O OH ? others? observed observed observed Martin, J. W.; Muir, D. C. G.; Solomon, K. R.; Moody, C. A.; Ellis, D. A.; Kwan, W.; Mabury, S. A. Anal. Chem. 2001, 74, 584 590.

Martin, J., S. A. Mabury, K. S. Solomon, D. C. G. Muir. 2002 Bioconcentration and Tissue Distribution of Perfluorinated Acids in Rainbow Trout ( Oncorhynchus mykiss Environ. Tox. Chem. Accepted.

Martin, J., S. A. Mabury, K. S. Solomon, D. C. G. Muir. 2002 Dietary Accumulation of Perfluorinated Acids in Rainbow Trout ( Oncorhynchus mykiss. Environ. Tox. Chem. Accepted. Napoli M, Krotz L, Conte L, Seraglia R, Traldi P. Rapid Commun. Mass Sp. 1993; 7: 1012.

Svoboda, V. C.; Koutek, B. Determination of saturated vapor pressures and heats of vaporization from gas chromatography retention data. Chemicke Listy 2002, 96, 10 18.

Von Werner K and Wrackmeyer B. J. Fluorine Chem. 1981; 19: 163.

Von Werner K and Wrackmeyer B. J. Fluorine Chem. 1986; 31: 196.

Wang J and Ober CK. Liq. Cryst. 1999; 26: 637 Presentations S. A. Mabury, " Environmental and Analytical Chemistry of Fluorinated Surfactants". DIOXIN 2002, Barcelona, Espana, August, 2002. Invited Speaker, Organizer of the session on " New POPs". Published Short Paper in " Xenobiotics".

S. A. Mabury, " Fluorinated Chemicals in the Environment ~ Redefining Persistence?" GLRM. American Chemical Society, Minneapolis, MN, June, 2002. Invited platform.

Martin, J. W., Muir, D. C. G., Stock, N., Moody, C. A., Ellis, D. A., Kwan, W. C., Mabury, S. A. " Detection of Fluorinated Organic Contaminants in Atmospheric Samples by GC/ CI/ MS". International Association of Great Lakes Research 45th Annual Conference, Winnipeg, May, 2002. Platform Presentation.

S. A. Mabury, " Redefining Persistence ~ Fluorinated Chemicals in the Environment". Environalysis 2002. Toronto, ON. May, 2002. Invited Keynote.

S. A. Mabury, " Flights of Fancy ~ Fluorinated Chemicals in the Environment". University of California Davis. May, 2002. Invited Seminar.

S. A. Mabury, " Perfluorinated Surfactants in Environmental Samples ~ Analysis by LC/ MS/ MS." 223rd American Chemical Society, Environmental Chemistry Division. April, 2002. Invited Platform.

S. A. Mabury, " 19F NMR in Analytical Chemistry", Asia Pacific Conference on Analytical Science, 19 22 Feb, 2002, Shangri La Hotel, Manila, Philippines. Invited Keynote Speaker. S. A. Mabury, " Analytical and Environmental Chemistry of Fluorinated Pollutants", Department of Chemistry, University of the Philippines Los Banos, Feb, 2002. Invited Seminar.

S. A. Mabury, " Carbonate Radical and the PhotoFate Test System. Institute of Chemistry, University of the Philippines Diliman, Feb, 2002. Invited Seminar.

S. A. Mabury, " A New Class of Pollutant ~ Fluorinated Compounds", Natural Science Research Institute, University of the Philippines Diliman, Feb, 2002. Invited Seminar.

S. A. Mabury, " Fluorinated Chemicals in the Environment: Analytical and Environmental Chemistry" Stanford University, Nov. 30, 2001. Invited Seminar.

S. A. Mabury. " What Makes a Chemical a Pollutant". Inaugural speaker in the " University of Toronto Lecture Series in Markham". October 3, 2001. Invited platform.


RFS2 Meeting Log

Includes all face-to-face meetings between EPA personnel and non-government stakeholders following signature of the RFS2 Notice of Proposed Rulemaking on May 5, 2009.

Date:  5-11-09	Location: DC and Video Conf to AA

EPA attendees:

Margo Oge, Paul Machiele, Karl Simon, Sarah Dunham, Paul Argyropolous, Lori Stewart, Robert Larson, Paul Machiele and Lester Wyborny

	Stakeholder attendees and affiliation:

Fulcrum BioEnergy

Jim Marcias, Ted Kniesche, Jessica Lenard, Stephen Sayle

Topics/issues/agenda:

Discussion of their new biofuel technology

Date:  5-11-09	Location: DC and Video Conf to AA

EPA attendees:

Paul Machiele, Lester Wyborny, Aaron Levy, Aron Butler, Dallas Burkholder, Doris Wu, Jefferson Cole, Julie Boledovich, Michael Shelby, Robert Larson

	Stakeholder attendees and affiliation:

Amyris

Kindeat Reiling, Fernando Garcia

Topics/issues/agenda:

Discussion of their new biofuel technology

Date:  5-13-09	Location: DC and Video Conf to AA

EPA attendees:

Aaron Levy, Aron Butler, Dallas Burkholder, David Korotney, Doris Wu, Jeff Herzog, Jefferson Cole, Jim Caldwell, Jose Solar, Julie Boledovich, Michael Shelby, Paul Machiele, Robert Larson, Sharyn Lie, Solveig Irvine, Vincent Camobreco, Zoltan Jung

	Stakeholder attendees and affiliation:

Bell Bioenergy

Topics/issues/agenda:

Discussion of their new cellulosic biofuel technology

Date:  5-13-09	Location:  Webinar from RFA's Offices

EPA attendees:

Sarah Dunham, Paul Argyropoulos, John Weihrauch, Karl Simon, David Korotney, Paul Machiele, Megan Brachtl, Robert Larson, Vincent Camobreco

	Stakeholder attendees and affiliation:

Renewable Fuels Association Webinar

Topics/issues/agenda:

Overview Briefing of the RFS2 NPRM

Date:  5-18-09	Location:  Conference Call

EPA attendees:

Paul Argyropoulos, John Weihrauch, David Korotney, Paul Machiele, Megan Brachtl, Robert Larson, Vincent Camobreco

	Stakeholder attendees and affiliation:

Conference Call with the Advanced Biofuel Association (Mike McAdams)

Topics/issues/agenda:

Overview Briefing of the RFS2 NPRM

Date:  5-20-09	Location:  Webinar

EPA attendees:

Paul Argyropoulos, John Weihrauch, David Korotney, Paul Machiele, Megan Brachtl, Robert Larson, Vincent Camobreco

	Stakeholder attendees and affiliation:

Webinar with HART

Topics/issues/agenda:

Overview Briefing of the RFS2 NPRM

Date:  5-20-09	Location:  Webinar

EPA attendees:

Paul Argyropoulos, John Weihrauch, David Korotney, Paul Machiele, Megan Brachtl, Robert Larson

	Stakeholder attendees and affiliation:

Webinar with Clean Fuels Clearinghouse (Clayton McMartin)

Topics/issues/agenda:

Overview Briefing of the RFS2 NPRM

Date:  5-21-09	Location:  Meeting in Ann Arbor and Conference Call

EPA attendees:

Paul Argyropoulos, John Weihrauch, David Korotney, Paul Machiele, Megan Brachtl, Robert Larson, Vincent Camobreco

	Stakeholder attendees and affiliation:

NPRA and API Fuels Committee

Topics/issues/agenda:

Overview Briefing of the RFS2 NPRM

Date:  5-22-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Sarah Dunham, Karl Simon, Paul Argyropoulos, John Weihrauch, David Korotney, Paul Machiele, Megan Brachtl, Robert Larson, Vincent Camobreco

	Stakeholder attendees and affiliation:

Kate McMahon at Friends of the Earth

Debbie Hammel from Natural Resources Defense Council

Ralph Heimlich (via phone)

Brit Lungdren at Environmental Defense Fund

Erin Lieberman at Defenders of Wildlife

Jason Hill (via phone)

Jesse Prentice-Dunn at Sierra Club

Brian Sit at Natural Resource Defense Council

Peter Ashcroft at Environmental Defense Fund

Barbara Bramble at National Wildlife Fund

Lena Moffitt at Union of Concerned Scientists

Topics/issues/agenda:

Overview Briefing of the RFS2 NPRM

Date:  5-27-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Paul Argyropoulos, Karen Laughlin, others

	Argentine Renewable Energies Chamber

RFS2 and Argentina Soy / Biodiesel

Topics/issues/agenda:

Overview Briefing of the RFS2 NPRM

Date:  5-29-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Paul Argyropoulos, Karen Laughlin, others

	US State Department

Participants: Rick Driscol, others

RFS2 and Argentina Soy / Biodiesel

Topics/issues/agenda:

Overview RFS2 NPRM and Brazil

Date:  6-2-09	Location:  Conference Call

EPA attendees:

Paul Machiele, Sarah Dunham, Paul Argyropoulos

	Stakeholder attendees and affiliation:

NAACA Membership

Topics/issues/agenda:

Overview Briefing of the RFS2 NPRM

Date:  6-5-09	Location:  Conference Call

EPA attendees:

Paul Machiele, Karl Simon, Paul Argyropoulos, Sarah Dunham

	Stakeholder attendees and affiliation:

Iogen

Chris Hessler

Topics/issues/agenda:

Cellulosic credit provisions

Date:  6-12-09	Location:  Webinar

EPA attendees:

John Weihrauch, David Korotney, Robert Larson

	Stakeholder attendees and affiliation:

Webinar with Informa

Topics/issues/agenda:

Overview Briefing of the RFS2 NPRM

Date:  6-12-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Rob Brenner, Paul Argyropoulos, others

	Stakeholder attendees and affiliation:

Live Fuels

Topics/issues/agenda:

Overview RFS2 NPRM – Live Fuels Technology

Date:  6-15-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Karl Simon, Meg McCarthy, Paul Machiele

	Stakeholder attendees and affiliation:

RFA, NCGA, NGFA and Farm Bureau

Topics/issues/agenda:

Renewable Biomass Proposal

Date:  6-16-09	Location:  Meeting in D.C. and Video Conference in AA

EPA attendees:

Karl Simon, Lori Stewart, Paul Argyropoulos, Sarah Dunham

	Stakeholder attendees and affiliation:

Iowa Ethanol and Biodiesel Producers

Monte Shaw, IRFA

Denny Mauser, Western Iowa Energy

Jim Johnston, Central Iowa Energy

TBD, Golden Grain Energy

Scott Poor, Green Plains Renewable Energy

Bill Couser, Lincolnway Energy

TBD, Little Sioux Corn Processors

Mike Jerke, Quad County Corn Processors

TBD, Renewable Energy Group

Bernie Punt, Siouxland Energy

Topics/issues/agenda:

Biodiesel related aspects of the proposal

Date:  6-16-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Paul Argyropoulos, others

	Stakeholder attendees and affiliation:

Terry Wigglesworth, Biodiesel Interests

Topics/issues/agenda:

RFS2 and Biodiesel Issues

Date:  6-16-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Paul Argyropoulos, Vincent Camobreco, others

	Stakeholder attendees and affiliation:

American Bakers Association

Topics/issues/agenda:

RFS2 Overview

Date:  6/18/09	Location:  Meeting in D.C. and Video Conference AA

EPA attendees:

Robert Larson, Vincent Camobreco, Aaron Levy, Venu Ghanta

	Stakeholder attendees and affiliation:

Brooke Coleman

Topics/issues/agenda:

Petroleum indirect impacts

Date:  6-18-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Paul Argyropoulos

	Stakeholder attendees and affiliation:

Cargill

John Hixson

Jackie Fee

Topics/issues/agenda:

RFS2

Date:  6-19-09	Location:  Conference Call

EPA attendees:

Pat Hamman, Paul Argyropoulos

	Stakeholder attendees and affiliation:

Drew Wallace

Topics/issues/agenda:

RFS2 and Biodiesel

Date:  6/25/09	Location:  Meeting in D.C. and Video Conference AA

EPA attendees:

Robert Larson, Vincent Camobreco,

	Stakeholder attendees and affiliation:

John Sheehan and Richard Nelson

Topics/issues/agenda:

Land use modeling

Date:  6-30-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Meg McCarthy, Paul Argyropoulos, others	Stakeholder attendees and affiliation:

NAFO

Topics/issues/agenda:

Renewable Biomass Proposal

Date:  7-9-09	Location:  Conference Call

EPA attendees:

Russ Smith, Julie Boledovich, Lester Wyborny

	Stakeholder attendees and affiliation:

Virent

Gregory Kenman, Mary Blanchard and Bob Razweik of Virent Energy Systems

Topics/issues/agenda:

Technology/Process/LCA

Date:  7-9-09	Location:  Conference Call

EPA attendees:

Barry Garelick, Erv Pickell, Jeff Kodish, John Hannon, Paul Machiele, Roland Dubois, Scott Christian

	Stakeholder attendees and affiliation:

Beacon Landfill

Jim Schretter

Topics/issues/agenda:

Treatment of Biogas

Date:  7/13/09	Location:  Meeting in D.C.

EPA attendees:

Robert Larson,

	Stakeholder attendees and affiliation:

National Corn Growers Association

Topics/issues/agenda:

Presentation by EPA on lifecycle assessment as in proposal

Date:  7/14/09	Location:  Meeting in D.C.

EPA attendees:

Robert Larson, Vincent Camobreco, Aaron Levy, Jefferson Cole, Michael Shelby, Sharyn Lie

	Stakeholder attendees and affiliation:

RFA, Bob Dineen, Tom Darlington

Topics/issues/agenda:

RFA’s analysis of LCA including land use changes; comparison of FASOM/FAPRI results and GTAP; yield projections; DGs use; marginal impact analysis

Conference Call with Small Business Refiners on RFS2

Date: 7/15/09, 1:00-3:00pm Eastern	Location: Varied (conference call)

EPA attendees:

David Korotney, Paul Machiele, Chris McKenna, Tia Sutton

	Stakeholder attendees and affiliation:

AGE- Cindy Fuqua, Lisa _____ (didn't catch the last name), Diane Williams

American Refining Group- John Robinson, Steve Sherk

Calumet- Gary Lindgren

CHS- Dustin Haaland

Countrymark- Mark Mauro, John Stern

CVR Energy- Robert Panchak

Frontier- Gerry Faudel??

Gary-Williams Energy Corp- Sally Allen, John Goodrich, Phil Waters

Holly- Gary Fuller

Hunt Refining- Casey Frederick

Kern Oil & Refining Co- Jerry Frost, Bob Richards

Montana Refining- Mike Raile

NCRA- David Balzar, Galen Menard, Dana Kresky, Terry Hardman, Jason Henrikson, Ben Oard

Petro Star, Inc.- Richard Curtin

Pasadena Refining- ?? (don't think anyone attended for Pasadena)

Placid- Pam Posster

San Joaquin Refining Company, Inc.- David Campbell

Silver Eagle- Blaine Zwahlen

Sinclair- Clint Ensign

Somerset Refining- Kevin Williams

United Refining- Bob Ennis, Lara Larson, Dean Stanton

U.S. Oil & Refining- Al Cabodi, Brent Brigham

Western Refining Co- Neil Gunn, Jeff Nichols (Stancil & Co)

Wyoming Refining Co- ?? (don't think Bob joined)

Topics/issues/agenda:

Overview briefing of the RFS2 NPRM

Discussion on small refiner flexibilities in the NPRM and the DOE Small Refinery Study

Initial feedback from small refiners on NPRM

Date:  7/16/09	Location:  Meeting in D.C. and Video Conference AA

EPA attendees:

Karen Laughlin, Robert Larson, Vincent Camobreco, Doris Wu

	Stakeholder attendees and affiliation:

Mendel Biotechnology

Jonathon Lehman

Neal Gutterson

Topics/issues/agenda:

Overview of company which provides new seed trait technologies for traditional crops and developing bioenergy seed business, efforts are focused on Miscanthus, development of a “perennial crop” pathway

Date:  7/16/09	Location:  Meeting in D.C. and Video Conference AA

EPA attendees:

Margo Oge, Karl Simon, Paul Argyropoulos, Paul Machiele, Robert Larson, Sarah Dunham

	Stakeholder attendees and affiliation:

Pat Raher

NRDC and UCS

Fulcrum

Topics/issues/agenda:

Treatment of MSW

Date:  7/20/09	Location:  Meeting in D.C. and Video Conference AA

EPA attendees:

David Korotney, Anne-Marie Pastorkovich, Anthony Miller, John Weihrauch, Karl Simon, Meg McCarthy, Megan Brachtl, Paul Machiele, Scott Christian

	Stakeholder attendees and affiliation:

Unica

Joel Valesco

Topics/issues/agenda:

Implications of the proposed registration, recordkeeping, reporting provisions, etc. on imports from Brazil

Date:  7/21/09	Location:  Meeting in D.C. and Video Conference AA

EPA attendees:

Karen Laughlin, Robert Larson, Vincent Camobreco, Paul Argyropoulos, Doris Wu

	Stakeholder attendees and affiliation:

Biofuels Manufacturers of Illinois

Peter Johnson

Topics/issues/agenda:

Discussion of use of pennycress as a feedstock for biodiesel

Date:  7/21/09	Location:  Meeting in D.C.

EPA attendees:

Anne-Marie Pastorkovich, Barry Garelick, Scott Christian

	Stakeholder attendees and affiliation:

Poet

Bob Whiteman

Topics/issues/agenda:

Discussion of waste-derived ethanol

  Date:  7/22/2009	Location:  Meeting in D.C and Video AA

EPA attendees:

Robert Larson, Vincent Camobreco, Karen Laughlin, Paul Argyropoulos Stakeholder attendees and affiliation:

Malaysian Palm Oil Board

Rosidah Radzian

Salleh Kassim

Malaysian palm oil production

Date:  7/23/09	Location:  Meeting in D.C. and Video Conference AA

EPA attendees:

Robert Larson, Vincent Camobreco, Doris Wu, Aaron Levy, Jefferson Cole, Michael Shelby

	Stakeholder attendees and affiliation:

National Biodiesel Board

Larry Schafer (NBB)

Manning Feraci (NBB)

Sandra Franco (Bingham)

Don O’Connor (S&T)2

John Urbanchuk (LEGG)

James Fry (LMC International)

Topics/issues/agenda:

Lifecycle analysis for biodiesel feedstocks

Date:  7/29/09	Location:  Meeting in D.C. and Video Conference AA

EPA attendees:

Vincent Camobreco, Doris Wu, Robert Larson, Paul Argyropoulos

	Stakeholder attendees and affiliation:

Novogy

Colin  South

Jay  Niles

Maureen  Walsh

Sarah  Litke

Topics/issues/agenda:

Their technology, process, energy use, costs, LCA, etc.

Date:  7/29/09	Location:  Meeting in D.C. and Video Conference AA

EPA attendees:

Aaron Levy, Dallas Burkholder, Lester Wyborny, Paul Machiele, Robert Larson, Russ Smith, Sharyn Lie, Vincent Camobreco, Robert Larson

	Stakeholder attendees and affiliation:

Syngenta

Lisa Jaeger

Topics/issues/agenda:

Their biogenetics technology and its implications with respect to LCA

Date:  8/05/2009	Location:  Meeting in D.C and video Conference AA

EPA attendees:

Aaron Levy, Vincent Camobreco, Robert Larson	Stakeholder attendees and affiliation:

Ken Copenhaver

Stefan Unnasch from Life Cycle Associates

Topics/issues/agenda

Land use assessment

Date:  8/06/09	Location:  Meeting in D.C. and Video Conference AA

EPA attendees:

Robert Larson, Vincent Camobreco, Doris Wu, Paul Argyropoulos

	Stakeholder attendees and affiliation:

Petroalgae

Topics/issues/agenda:

Commercial plans and technology overview, algae definition to microcrops

Meeting with Chevron

Date:  8/6/09 1pm to 3pm	Location:  Ann Arbor

EPA attendees:

Paul Machiele

Julie Boledovich

Lester Wyborny

David Korotney

John Weihrauch

Tony Miller

Meg McCarthy	Stakeholder attendees and affiliation:

Peter Dahling

Al Jessel

Bob Anderson

Dennis Halleron

Karen Means

Topics/issues/agenda:

BBD RIN Compliance / Program Start Date

Obligated Party / Point of Regulation / Producer Separation of RINs

Cellulosic Biofuel Volume Projection / Adjusted Mandate Volumes / Allowance Program

E10 Blend Wall

Palm Oil as a Bio/Renewable Diesel Feedstock

Implementation of EMTS

Date:  8-6-09	Location:  Conference Call

EPA attendees:

Paul Argyropoulos

	Stakeholder attendees and affiliation:

ABA

Mike McAdams

Topics/issues/agenda:

RFS2

Meeting with Catherine Almirall

Date:  8/06/2009	Location:  Meeting in D.C. and Video Conference to Ann Arbor

EPA attendees:

Aaron Levy, Vincent Camobreco, Jefferson Cole, Doris Wu, Robert Larson, Sharyn Lie

	Stakeholder attendees and affiliation:

Catherine Almirall

Topics/issues/agenda:

Sugarcane and soybean acres in Brazil

Date:  8-12-09	Location: DC

EPA attendees:

Tony Miller

John Weihrauch

Scott Christian

	Stakeholder attendees and affiliation:

RINxchange – John Gelbard and Rob Burroughs

Topics/issues/agenda:

Discussion of EMTS functionality and integration.

Date:  8-20-09	Location:  DC

EPA attendees:

Tony Miller

John Weihrauch

Scott Christian

	Stakeholder attendees and affiliation:

RINStar – Clayton McMartin and Melissa Donovan

Topics/issues/agenda:

Discussion of EMTS functionality and integration.

Date:  9-10-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Paul Argyropoulos, others

	Stakeholder attendees and affiliation:

Endicott Biofuels

Stephen Brown

Topics/issues/agenda:

General on RFS2

Meeting with Coskata

Date:  9/15/09 1pm to 3pm	Location:  Ann Arbor

EPA attendees:

Paul Machiele

Lester Wyborny

Julie Boledovich

Dallas Burkholder

Aron Butler

Doris Wu

	Stakeholder attendees and affiliation:

Wes Bolsen

Loula Merkel

Topics/issues/agenda:

Obtain update on pilot plant and commercial plant operations and plans

Request updated, projected plant operations information for life cycle analysis

Discuss some aspects of the proposed rulemaking

Date:  9-18-09	Location:  Meeting in D.C.

EPA attendees:

Paul Argyropoulos

	Stakeholder attendees and affiliation:

BP

Ruthie

Topics/issues/agenda:

General on RFS2

Date:  9/18/09	Location:  Meeting in D.C. and Video Conference AA

EPA attendees:

Robert Larson, Vincent Camobreco, Doris Wu, Aaron Levy, Jefferson Cole, Michael Shelby, Sharyn Lie

	Stakeholder attendees and affiliation:

Monsanto

Beth Calabotta

Topics/issues/agenda:

Crop yield and technologies

Date:  9-22-09	Location:  Conference Call

EPA attendees:

Paul Argyropoulos, others

	Stakeholder attendees and affiliation:

Clean Fuels Clearing House

Clayton McMartin

Topics/issues/agenda:

RFS2 – RIN Program

Date:  9/28/09	Location:  Meeting in D.C. at Exxon

EPA attendees:

Margo Oge, Karl Simon, Sarah Dunham, Chet France

	Stakeholder attendees and affiliation:

Exxon

John Medley contact

Topics/issues/agenda:

Various Topics, some of which touched on RFS2 rulemaking issues

Date:  9-30-09	Location:  Meeting in D.C. or Conference Call

EPA attendees:

Paul Argyropoulos

	Stakeholder attendees and affiliation:

Clean Fuels Development Coalition

Doug Durante

Burl Haigwood

Topics/issues/agenda:

General on RFS2

Date:  10-1-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Paul Argyropoulos

	Stakeholder attendees and affiliation:

REG

Steve Falck

Sara Taylor (Bluefront Group)

Topics/issues/agenda:

RFS2

Date:  10-2-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Paul Argyropoulos, Paul Machiele, Karl Simon, John Weihrauch, others

	Stakeholder attendees and affiliation:

IOGEN

John Foody, Chris Hessler

Topics/issues/agenda:

RFS2, Cellulosic Standards

Date:  10-5-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Paul Argyropoulos

	Stakeholder attendees and affiliation:

Synthetic Genomes

Ari Patrinos

Topics/issues/agenda:

General on RFS2

Date:  10-6-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Gina McCarthy, Sarah Dunham, Paul Argyropoulos, others

	Stakeholder attendees and affiliation:

Biodiesel Producers

Topics/issues/agenda:

Biodiesel issues and RFS2

Date:  10-7-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

OCIR, Paul Argyropoulos, others

	Stakeholder attendees and affiliation:

Senator Sessions Staff

Topics/issues/agenda:

RFS2 RIN Issues

Date:  10-8-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Paul Argyropoulos

	Stakeholder attendees and affiliation:

Carribbean Basin Initiative – Jamaican Embassy

Topics/issues/agenda:

CBI Compliance – RFS2- Dehydrator Interests

Date:  10-13-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Meg McCarthy, CISD, Paul Argyropoulos, TCD

	Stakeholder attendees and affiliation:

UNICA

Topics/issues/agenda:

Brazilian Ethanol – RINs, Product Tracking, etc.

Date:  10-13-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Paul Argyropoulos, Others

	Stakeholder attendees and affiliation:

BASF

Mike Heltzer, Steve Goldberg, Dr. Mike Pcolinski, Dr. Stefan Koser

Topics/issues/agenda:

RFS2 - Technology

Meeting with Enerkem	Location:  Meeting in D.C. and Conference Call

Date:  10/14/09  9am to 10:30 am	Stakeholder attendees and affiliation:

REG

Steve Falck, Sara Taylor (Bluefront Group)

EPA attendees:

Russ Smith

Lester Wyborny

Julie Boledovich

Dallas Burkholder

Aron Butler

Topics/issues/agenda:

Obtain update on pilot plant and commercial plant operations and plans

Request updated, projected plant operations information for life cycle analysis

Discuss some aspects of the proposed rulemaking

Date:  10-14-09	Location:  DC

EPA attendees:

Tony Miller

John Weihrauch

Scott Christian

	Stakeholder attendees and affiliation:

Renewable Fuels Association - Jim Redding

ADM – Amanda Akers, Wayne Sharp, Bruce Logan, Carrie Young

Topics/issues/agenda:

EMTS demonstration and overview.

Date:  10-15-09	Location:  DC

EPA attendees:

Tony Miller

John Weihrauch

Scott Christian

	Stakeholder attendees and affiliation:

American Petroleum Institute – Al Mannato, Keyo Didier, Patrick Kelly

Topics/issues/agenda:

EMTS demonstration and overview.

Date:  10-15-09	Location:  DC

EPA attendees:

Tony Miller

John Weihrauch

Scott Christian

	Stakeholder attendees and affiliation:

National Petrochemical and Refiners Association – Tim Hogan

Topics/issues/agenda:

EMTS demonstration and overview.

Date:  10-20-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Paul Argyropoulos

	Stakeholder attendees and affiliation:

Clean Energy, Andrew Littlefair

Scott Reed

Topics/issues/agenda:

RFS2 and Biofuel Issues

Date:  10/20/09	Location:  Meeting in Chicago Ill

EPA attendees:

Robert Larson,

	Stakeholder attendees and affiliation:

Various

Topics/issues/agenda:

CRC workshop on LCA

Date:  10/20/09	Location:  Meeting in Chicago Ill

EPA attendees:

Robert Larson,

	Stakeholder attendees and affiliation:

Neste Oil

Neville Fernandes

Topics/issues/agenda:

Biofuel plans

Date:  10-26-09	Location:  DC

EPA attendees:

Tony Miller

John Weihrauch

Scott Christian

	Stakeholder attendees and affiliation:

Petroleum Marketers Association of America – Brandon Wright, Dan Gilligan, Mark Morgan

Topics/issues/agenda:

EMTS demonstration and overview.

Meeting with Darlington Int’l

Date:  11/03/2009	Location: Meeting in DC and Video AA

EPA attendees:

Paul Argyropoulos

Doris Wu

Aron Butler

	Stakeholder attendees and affiliation:

Darlington Int’l

Topics/issues/agenda:

Developing pathway for animal fats

Renewable diesel expansion plans

Feedstock Availability

Date: 11/12/09 10:00 AM to 11:00 AM	Location:  Conference Call

EPA attendees:

Barry Garelick

Roland Dubois

	Stakeholder attendees and affiliation:

Nathaniel Greene, NRDC

Topics/issues/agenda:

Discussion of EISA definition of renewable biomass and whether MSW qualifies as such.

Discussed aspects of their comments and what constitutes adequate “separation”.

Discussed aspects of NPRM.

Date: 11/12/09 1:00 PM to 2:00 PM	Location:  Conference Call

EPA attendees:

Scott Christian, EPA

	Stakeholder attendees and affiliation:

Jim Redding, Renewable Fuels Assn

Samantha Slater, Renewable Fuels Assn

Sandra Franco, Renewable Fuels Assn

Wes Golson, Coskata

Loula Merkel, Coskata

Eric Gockel NES Bio

Chris Hessler, representing Iogen

Topics/issues/agenda:

We discussed the invitee’s comments that were provided to the docket on the cellulosic biofuel waiver credits provision.

Date:  11-16-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Paul Argyropoulos and others

	Stakeholder attendees and affiliation:

NPRA / API

Tim Hogan and Members

Topics/issues/agenda:

RFS2 and E15.

Meeting with Iowa Soybean Association

Date:  11/18/09	Location:  Meeting in D.C. and Video Conference to Ann Arbor

EPA attendees:

Margo Oge

Paul Argyropoulos

Paul Machiele

Robert Larson

Sarah Dunham

	Stakeholder attendees and affiliation:

Grant Kimberley

Karen Long

Topics/issues/agenda:

Treatment of biodiesel and Soy

Meeting with Endicott Biofuels

Date:  11/19/09	Location:  Meeting in Ann Arbor and Conference Call

EPA attendees:

Paul Machiele

Lester Wyborny

Aron Butler

Julie Boledovich

Russ Smith

Dallas Burkholder

Dori Wu

	Stakeholder attendees and affiliation:

Christopher Frantz

Topics/issues/agenda:

Obtain update on pilot plant and commercial plant operations and plans

Request updated, projected plant operations information for life cycle analysis

Discuss some aspects of the proposed rulemaking

Date:  11/18/09	Location:  Meeting in D.C. and Video Conference to Ann Arbor

EPA attendees:

Margo Oge

Paul Argyropoulos

Paul Machiele

John Hannon

Sarah Dunham

	Stakeholder attendees and affiliation:

Pat Raher

Lattiny Montegue

CEOs of Fulcrum, Coskata, etc.

Topics/issues/agenda:

Treatment of MSW

Date:  11/30/09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

John Weihrauch, EPA

David Korotney, EPA

Scott Christian, EPA

Paul Argyropoulos, EPA

Pascal Dedjinou, EPA

Karl Simon, EPA	Stakeholder attendees and affiliation:

Jim Redding, Renewable Fuels Assn

Samantha Slater, Renewable Fuels Assn

Loula Merkel, Coskata

Amy Ehlers, BIO

Chris Hessler, representing Iogen

Topics/issues/agenda:

We discussed the invitee’s comments that were provided to the docket on the cellulosic biofuel waiver credits provision.

Date:  12-1-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Paul Argyropoulos, others

	Stakeholder attendees and affiliation:

Coskata, RFA, AJW, BIO

Chris Hessler, Amy Ehlers, others

Topics/issues/agenda:

RFS2.

Date:  12-10-09	Location:  Meeting in D.C. and Conference Call

EPA attendees:

Paul Argyropoulos

	Stakeholder attendees and affiliation:

US Renewable Group

Tim Newell

Topics/issues/agenda:

RFS2

Meeting with HydroMentia

Date:  12/15/09	Location:  Meeting in D.C. and Video Conference to Ann Arbor

EPA attendees:

Margo Oge

Paul Argyropoulos

Paul Machiele

Robert Larson

Karl Simon

Roberta Parry

Robert Bastian

	Stakeholder attendees and affiliation:

Don Panoz

William Sawyer

Topics/issues/agenda:

Their Algae Technology

Date:  12-18-09	Location:  Conference Call

EPA attendees:

Paul Argyropoulos

	Stakeholder attendees and affiliation:

Roundtable for Sustainable

Topics/issues/agenda:

Overview – RFS2