Elevance Renewable Sciences, Inc.

Patent Trials and Appeals Board

Jun 16, 2020

2019003610 (P.T.A.B. Jun. 16, 2020)

UNITED STATES PATENT AND TRADEMARK OFFICE
UNITED STATES DEPARTMENT OF COMMERCE
United States Patent and Trademark Office
Address: COMMISSIONER FOR PATENTS
P.O. Box 1450
Alexandria, Virginia 22313-1450
www.uspto.gov
APPLICATION NO. FILING DATE FIRST NAMED INVENTOR ATTORNEY DOCKET NO. CONFIRMATION NO.
14/678,749 04/03/2015 Timothy W. Abraham ERS-020-1-US-4 5864
144757 7590 06/16/2020
Elevance Renewable Sciences, Inc. (Main)
Kilpatrick Townsend & Stockton LLP
1100 Peachtree St. NE
Suite 2800
Atlanta, GA 30309
EXAMINER
KEYS, ROSALYND ANN
ART UNIT PAPER NUMBER
1699
NOTIFICATION DATE DELIVERY MODE
06/16/2020 ELECTRONIC
Please find below and/or attached an Office communication concerning this application or proceeding.
The time period for reply, if any, is set in the attached communication.
Notice of the Office communication was sent electronically on above-indicated "Notification Date" to the
following e-mail address(es):
elevance_docketing@cardinal-ip.com
ipefiling@kilpatricktownsend.com
patents@elevance.com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte TIMOTHY W. ABRAHAM, HIROKI HAIDO, CHOON WOO
LEE, RICHARD L. PEDERSON, YANN SCHRODI, and MICHAEL
JOHN TUPY
Appeal 2019-003610
Application 14/678,749
Technology Center 1600
Before JOHN E. SCHNEIDER, RYAN H. FLAX, and
CYNTHIA M. HARDMAN, Administrative Patent Judges.

SCHNEIDER, Administrative Patent Judge.
DECISION ON APPEAL
STATEMENT OF THE CASE
Pursuant to 35 U.S.C. § 134(a), Appellant1 appeals from the
Examiner’s decision to reject claims 91–102 and 107. We have jurisdiction
under 35 U.S.C. § 6(b).
We REVERSE.

1 We use the word Appellant to refer to “applicant” as defined in 37 C.F.R.
§ 1.42(a). Appellant identifies the real party in interest as Elevance
Renewable Sciences, Inc. Appeal Br. 3.
Appeal 2019-003610
Application 14/678,749
2
CLAIMED SUBJECT MATTER
The claims are directed to methods for making organic compounds by
metathesis. Claim 91, reproduced below, is illustrative of the claimed
subject matter:
91. A method comprising:
providing (a) a starting material comprising unsaturated
fatty acid triglycerides and (b) short-chain alpha-olefins;
cross-metathesizing the unsaturated fatty acid
triglycerides of the starting material and the short-chain alpha-
olefins in the presence of a metathesis catalyst to provide cross-
metathesis products comprising olefins and ester-functionalized
alkenes, wherein the ester-functionalized alkenes comprise
unsaturated fatty acid triglycerides;
separating the olefins in the cross-metathesis products and
the ester-functionalized alkenes in the cross-metathesis products
to provide separated olefins and separated ester-functionalized
alkenes, wherein the separated ester-functionalized alkenes
comprise unsaturated fatty acid triglycerides; and
transesterifying the separated ester-functionalized alkenes
in the presence of an alcohol to provide a transesterified product
comprising glycerol and free ester-functionalized alkenes.

REFERENCES
The prior art relied upon by the Examiner is:
Name Reference Date
Lysenko et al. US2005/0154221 A1 July 14, 2005
J.C. Mol, Metathesis of unsaturated fatty acid esters and fatty oils, 90 J.
Mol. Cat. 185 (1994)
Patel et al., High conversion and productive catalyst turnovers in cross-
metathesis reactions of Natural oils with 2-butene, 8 Green Chem. 450
(2006)

Appeal 2019-003610
Application 14/678,749
3
REJECTIONS
The Examiner has rejected the pending claims as follows:
Claims 91–93, 96–98, and 107 have been rejected under 35 U.S.C.
§ 103(a) as unpatentable over Lysenko.
Claims 91–102 and 107 have been rejected under 35 U.S.C. § 103(a)
as unpatentable over Mol in view of Lysenko and Patel.
Claims 91–99 and 107 have been rejected under 35 U.S.C. § 103(a) as
unpatentable over Lysenko in view of Mol and Patel.
OBVIOUSNESS BASED ON LYSENKO
Issue
The issue with respect to this rejection is whether a preponderance of
the evidence supports the Examiner’s conclusion that the subject matter of
claims 91–93, 96–98, and 107 would have been obvious to one of ordinary
skill in the art at the time the invention was made over the teachings of
Lysenko.
The Examiner finds that Lysenko teaches a process whereby a fatty
acid ester feedstock is metathesized with a lower olefin using a metathesis
catalyst to produce a mixture comprising a reduced chain olefin and a
reduced chain fatty ester. Final Act. 9. The Examiner finds that Lysenko
teaches that the mixture can be separated by conventional methods and the
reduced chain unsaturated esters can be transesterified with a polyol such as
glycerol. Id. The Examiner finds that Lysenko teaches that the feedstock
may comprise plant and vegetable oils such as “castor, olive, peanut,
rapeseed, corn, sesame, cottonseed, soybean, sunflower, canola, safflower,
linseed, and the like,” and the olefins can include C2 to C5 olefins including
alpha-olefins. Id.
Appeal 2019-003610
Application 14/678,749
4
Appellant contends that Lysenko does not teach or suggest the direct
cross-metathesis of an unsaturated fatty acid triglyceride with a short chain
alpha-olefin. Appeal Br. 9. Appellant contends that paragraph 14 of
Lysenko only refers to unsaturated fatty acid esters and that paragraph 50 of
the reference discourages the use of unsaturated triglycerides. Id.
Appellant also contends that Lysenko does not teach or suggest
transesterification of a glyceride ester to yield glycerol as a product. Id.
Appellant contends that Lysenko teaches the opposite reaction, namely the
reaction of a lower alkyl ester with glycerol to produce a glyceride ester and
a lower alkanol product. Id. at 10.
Legal Principles
“[T]he examiner bears the initial burden, on review of the prior art or
on any other ground, of presenting a prima facie case of unpatentability. If
that burden is met, the burden of coming forward with evidence or argument
shifts to the applicant.” In re Oetiker, 977 F.2d 1443, 1445 (Fed. Cir. 1992).
A prima facie case for obviousness “requires a suggestion of all
limitations in a claim,” CFMT, Inc. v. Yieldup Int’l Corp., 349 F.3d 1333,
1342 (Fed. Cir. 2003), and “a reason that would have prompted a person of
ordinary skill in the relevant field to combine the elements in the way the
claimed new invention does.” KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398,
418 (2007).
Analysis
We have considered the arguments advanced by both the Examiner
and Appellant and conclude that the Appellant has the better positon. We
agree with the Appellant that the Examiner has not established that Lysenko
teaches a transesterification step which results in “a transesterified product
comprising glycerol and free ester-functionalized alkenes.” Appeal Br. 14.
Appeal 2019-003610
Application 14/678,749
5
Lysenko teaches the use of glycerol as a reactant to esterify a lower alkyl
ester to produce a glyceride ester and a lower alkanol product. Lysenko ¶
80.
The Examiner contends that since the reaction mixture includes
glycerol, there is likely some glycerol remaining in the final product, thus
meeting the requirement that the product include glycerol. Ans. 10. We are
not persuaded by this argument.
As Appellant points out, the Examiner’s argument appears to be based
on inherency. Reply Br. 4. To establish inherency, the Examiner must show
that glycerol is necessarily present in the finished product, not that it might
be present. In re Montgomery, 677 F.3d 1375, 1379–80 (Fed. Cir. 2012).
Here the Examiner has not offered any evidence that glycerol is necessarily
present in the final product. In fact, Lysenko teaches that an excess amount
of the ester is used in the reaction and the lower alkanol is removed from the
reaction to drive the reaction forward. Lysenko ¶ 80. This supports the
conclusion that the final product does not contain any unreacted glycerol.
Reply Br. 4.
Conclusion
Based on the foregoing, we conclude that a preponderance of the
evidence does not support the Examiner’s conclusion that claims 91–93, 96–
98, and 107 would have been obvious to one of ordinary skill in the art at the
time the invention was made over the teachings of Lysenko.
OBVIOUSNESS BASED ON MOL, LYSENKO, AND PATEL
Issue
The issue with respect to this rejection is whether a preponderance of
the evidence supports the Examiner’s conclusion that the subject matter of
claims 91–102 and 107 would have been obvious of one of ordinary skill in
Appeal 2019-003610
Application 14/678,749
6
the art at time the invention was made over Mol combined with Lysenko and
Patel.
The Examiner finds that Mol teaches a method whereby vegetable oils
are cross-metathesized with lower olefins. Final Act. 7. The Examiner finds
that Mol does not teach or suggest the use of a short chain alpha-olefin, but
that the element is taught by Lysenko. Id. at 8. The Examiner also finds that
Mol does not teach the additional steps of separating the olefins from the
ester-functionalized alkenes followed by transesterification of the ester-
functionalized alkenes, but that those steps are taught by Patel. Id.
Appellant contends that the Examiner has failed to set forth any
reason why one skilled in the art would have modified the process of Mol to
incorporate the teachings of Lysenko and Patel to arrive at the claimed
invention. Appeal Br. 10. Appellant contends that the Examiner has not
explained why one skilled in the art would use the lower alpha olefins of
Lysenko when one example does not use an olefin as a reactant and another
uses internal olefins not alpha olefins. Id. at 10–11. Appellant contends that
for the one example which uses an alpha olefin, there is no teaching or
suggestion to transesterify the product of the metathesis reaction. Id.
Appellant contends that the modifications proposed by the Examiner would
result in significantly less product than the method recited in Mol or would
result in a completely different product. Id.
Legal Principles
“Obviousness requires more than a mere showing that the prior art
includes separate references covering each separate limitation in a claim
under examination.” Unigene Labs., Inc. v. Apotex, Inc., 655 F.3d 1352,
1360 (Fed. Cir. 2011). “Rather, obviousness requires the additional showing
that a person of ordinary skill at the time of the invention would have
Appeal 2019-003610
Application 14/678,749
7
selected and combined those prior art elements in the normal course of
research and development to yield the claimed invention.” Id.
Analysis
We have considered the arguments advanced by both the Examiner
and Appellant and conclude that Appellant has the better position. While the
individual elements of the claims may appear in the individual references,
we discern no motivation to combine the references in the manner suggested
by the Examiner. Specifically the Examiner has not convincingly explained
why one skilled in the art would use a lower alpha olefin in the first and
third processes taught by Mol, nor has the Examiner explained why one
skilled in the art would subject the product of the second reaction described
in Mol to transesterification such that an ester-functionalized alkene and
glycerol are produced.
The Examiner argues that both Lysenko and Mol teach that
transesterification can be performed on the products of metathesis and that
Patel teaches that transesterification can be used to liberate fatty acids and
esters including those produced in Mol. Ans. 12–13. While this may be
true, those teachings only show that the transesterification step is possible
and what the result might be. The Examiner does not explain why one
skilled in the art would want to transesterify the products produce in Mol or
why the resulting products might be desirable.
Conclusion
We conclude that a preponderance of the evidence does not support
the Examiner’s conclusion that the subject matter of claims 91–102 and 107
would have been obvious of one of ordinary skill in the art at time the
invention was made over Mol combined with Lysenko and Patel.
Appeal 2019-003610
Application 14/678,749
8
OBVIOUSNESS BASED ON LYSENKO, MOL, AND PATEL
Issue
The issue with respect to this rejection is whether a preponderance of
the evidence supports the Examiner’s conclusion that the subject matter of
claims 91–99 and 107 would have been obvious to one skilled in the art at
the time the invention was made over Lysenko combined with Mol and
Patel.
The Examiner finds that Lysenko teaches a process wherein a fatty
acid ester feedstock is metathesized with a lower olefin to produce a reduced
chain olefin and reduced chain unsaturated fatty ester. Final Act. 9. The
Examiner finds that Lysenko also teaches that the metathesis products can be
separated and the reduced chain unsaturated esters can be esterified. Id. The
Examiner finds that while Lysenko does not specifically teach the use of an
unsaturated fatty acid triglyceride as a feedstock, Lysenko teaches that the
feedstock can be any fatty acid or fatty acid ester feedstock “provided that
the unsaturated fatty acids or unsaturated fatty acid esters contained therein
can be metathesized to form reduced chain olefins and reduced chain
unsaturated acids or esters.” Id. at 10 (quoting Lysenko ¶ 53). The
Examiner finds that Patel and Mol teach the cross-metathesis of triglycerides
with lower olefins for produce reduced chain olefins and reduced chain
unsaturated acids and esters. Id.
The Examiner concludes
One having ordinary skill in the art at the time the
invention was made would have found it obvious that an
unsaturated fatty acid triglyceride, such as disclosed by Patel et
al. and J. C. Mol could be cross-metathesized in the process of
Lysenko et al., since Patel et al. and J.C. Mol have shown that
triglycerides derived from natural oils can be cross-
metathesized with lower olefins to form reduced chain olefins
Appeal 2019-003610
Application 14/678,749
9
and reduced chain unsaturated acids and esters and Lysenko et
al. disclose that any fatty acid ester feedstock can be suitably
employed in the metathesis provided that the unsaturated fatty
acids contained therein can be metathesized to form reduced
chain olefins and reduced chain unsaturated esters.
Id.
Appellant contends that the Examiner has not provided an adequate
motivation to combine the references. Appeal Br. 11. Appellant contends
that Lysenko does not teach or suggest the use of unsaturated triglycerides as
a reactant and in fact teaches away from using triglycerides as reactants. Id.
at 12. Appellant contends that neither Mol nor Patel cure this deficiency of
Lysenko. Id. at 11–12.
Analysis
We have considered the arguments advanced by the Examiner and
Appellant and conclude that the Examiner has not established that the
subject matter of the claims would have been obvious over Lysenko
combined with Mol and Patel.
In making this rejection, the Examiner relies on Lysenko for the
transesterification step. Final Act. 10. However, as discussed above, the
transesterification step in Lysenko does not yield glycerol as a reaction
product. See Lysenko ¶ 80. The Examiner has not pointed to, nor have we
discerned any teaching in Mol or Patel of, a transesterification step which
yields a product comprising glycerol and free ester-functionalized alkenes.
Conclusion
We conclude that a preponderance of the evidence does not support
the Examiner’s conclusion that claims 91–99 and 107 would have been
obvious to one skilled in the art at the time the invention was made over
Lysenko combined with Mol and Patel.
Appeal 2019-003610
Application 14/678,749
10
CONCLUSION
The Examiner’s rejections under 35 U.S.C. §103(a) are reversed.
DECISION SUMMARY
In summary:
Claims
Rejected
35 U.S.C. § Reference(s)/Basis Affirmed Reversed
91–93, 96–
98, 107
103(a) Lysenko 91–93, 96–
98, 107
91–102,
107
103(a) Mol, Lysenko,
Patel
91–102,
107
91–99, 107 103(a) Lysenko, Mol,
Patel
91–99, 107
Overall
Outcome
91–102,
107

REVERSED