Ex Parte Lebedev

Board of Patent Appeals and Interferences

Dec 1, 2009

11489100 (B.P.A.I. Dec. 1, 2009)

UNITED STATES PATENT AND TRADEMARK OFFICE
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BEFORE THE BOARD OF PATENT APPEALS
AND INTERFERENCES
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Ex parte MIKHAIL Y. LEBEDEV

Appellant
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Appeal 2009-008879
Application 11/489,100
Technology Center 1600
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Decided: December 1, 2009
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Before RICHARD TORCZON, SALLY GARDNER LANE, and
MICHAEL P. TIERNEY Administrative Patent Judges.

LANE, Administrative Patent Judge.

DECISION ON APPEAL
I. STATEMENT OF THE CASE
The appeal, under 35 U.S.C. § 134(a), is from a Final Rejection of
Appellant’s claims 1-20. We have jurisdiction under 35 U.S.C. § 6(b). We
affirm.
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Appellant’s application is directed to a method of preparing
tricyclodecenyl esters, which are used as fragrance compounds. (Spec. 1,
ll. 5-7).
The Examiner relied on the following references:
Name Number Issue Date
Bruson 2,395,452 February 26, 1946
Gruffaz 4,281,176 July 28, 1981

The Examiner rejected claims 1-20 under 35 U.S.C. § 103(a) as being
rendered obvious by Bruson and Gruffaz. Appellant did not argue
separately for the patentability of any of the claims. We focus our review on
claim 1. See 37 C.F.R. § 1.37(c)(1)(vii).
II. PRINCIPLES OF LAW
“If a person of ordinary skill can implement a predictable variation,
§ 103 likely bars its patentability.” KSR Int’l Co. v. Teleflex, Inc., 550 U.S.
398, 417 (2007). “When there is a design need or market pressure to solve a
problem and there are a finite number of identified, predictable solutions, a
person of ordinary skill has good reason to pursue the known options within
his or her technical grasp. If this leads to the anticipated success, it is likely
the product not of innovation but of ordinary skill and common sense. In
that instance the fact that a combination was obvious to try might show that
it was obvious under § 103.” Id. at 421.
III. FINDINGS OF FACT
1. Appellant’s claim 1 recites:
A process comprising reacting a C2-C4 carboxylic acid and a
dicyclopentadiene [“DCPD”] at a carboxylic acid:dicyclopentadiene
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molar ratio within the range of 0.8 to 1.3 in the presence of triflic acid
under conditions effective to produce a tricyclodecenyl ester.

(App. Br. 11, Claims App’x.).
2. Bruson teaches reacting glacial acetic acid (a C2-C4 carboxylic
acid) and DCPD in the presence of sulfuric acid, as a catalyst, (Bruson p. 3,
col. A, ll. 58-61) to form carboxylic esters (Id. p. 1, col. A, ll. 1-6).
3. Bruson does not teach using triflic acid as a catalyst in the
reaction of C2-C4 carboxylic acids and DCPD, as claimed.
4. Gruffaz teaches using triflic acid1 as a catalyst between
carboxylic acid and ethylene to form ethyl esters. (Gruffaz col. 5, ll. 16-20).
5. Gruffaz reports using sulfuric acid as a catalyst between acetic
acid and ethylene to form ethyl acetate. (Gruffaz col. 4, ll. 15-26 and 40,
Table I).
IV. ISSUE
Would it have been obvious for those of skill in the art to use triflic
acid in a reaction with DCPD based on the teaching of Gruffaz to use triflic
acid in a reaction with ethylene?
V. ANALYSIS
The process taught in Bruson is different from the claimed process
because it does not employ triflic acid to react a C2-C4 carboxylic acid with
DCPD to form an ester. (FFs 1 and 3). Instead, Bruson uses sulfuric acid as
a catalyst. (FF 2).

1 Gruffaz refers to “trifluoromethanesulfonic acid,” which Appellant’s
specification acknowledges is “triflic acid.” (See Spec. p. 3, l. 13).
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Gruffaz uses triflic acid to catalyze formation of ethyl esters, but in a
reaction with ethylene, not DCPD. (FFs 4 and 5).
According to the Examiner, those of skill in the art would have had a
reasonable expectation of success in substituting triflic acid for sulfuric acid
as a catalyst because both Gruffaz and Bruson teach forming esters by
adding carboxylic acid to an olefin with an acid. (Ans. 4-5). As further
support that triflic acid and sulfuric acid would both be expected to catalyze
the reaction taught in Bruson, the Examiner relies on the teaching in Gruffaz
that sulfuric acid, like triflic acid, catalyzes reactions to form esters. (Ans.
12-13; FF 5). Finally, the Examiner cites the extensive analysis by Gruffaz
of the efficiencies of the reaction with triflic acid as evidence that those of
skill in the art would have been motivated to make this substitution. (Ans.
4-5).
Appellant argues that there are differences between the double bonds
of DCPD and ethylene that would make the claimed addition reaction
unpredictable. (Reply Br. 2-3). Appellant asserts that ethylene has no
substituents, while both double bonds of DCPD are alkyl-substituted and
that the alkyl-substituted groups of DCPD would stabilize the carbon-carbon
bonds, making them “less inclined” than ethylene to react with electrophiles.
(Reply Br. 3). In addition, Appellant argues that DCPD and ethylene are not
sterically equivalent because ethylene is planar while DCPD is complex and
has a three-dimensional geometry. (Reply Br. 3).
We are not persuaded by Appellant’s argument that the Examiner has
not presented a prima facie case for the obviousness of the claimed process.
In general, Appellant argues that “[a] skilled person would hardly consider
any organic compound having a ‘double bond’ as an equivalent of the
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DCPD required by Appellant’s claims.” (App. Br. 4 and 7-8). Appellant
notes some differences between the double bonds of ethylene and DCPD,
but does not support these observations with sufficient evidence that the
differences would have been considered by those of skill in the art
significant enough that triflic acid would not have been expected to catalyze
reactions with DCPD. (Reply Br. 2-3). Appellant cites to a text book in
support of its argument that DCPD is less likely to react due to the alkyl-
disubstituted double bonds of DCPD (Reply Br. 3). Appellant failed to
provide any portion of the text book or to cite to specific sections or pages.
As Appellant has not pointed to any teaching that compares the electron
donating or withdrawing strength of DCPD and ethylene, we have not
considered any teaching from the text book.2 Appellant has not directed us
to persuasive evidence establishing that the cited differences would preclude
using triflic acid as a catalyst, or at least trying it where ethylene was useful
See KSR, 550 U.S. 420. Thus, we are not persuaded that Appellant’s
evidence or arguments contradict the Examiner’s prima facie case. See KSR,
550 U.S. at 417.
Appellant also argues that both Bruson and Gruffaz limit the
compounds each discloses (App. Br. 4-5) and that Bruson expresses a
preference for sulfuric acid as the catalyst (App. Br. 7). “Non-obviousness

2 We remind Appellant that failing to cite specific pages of large references
offers little, if any, help for their argument. Cf., Halliburton Energy Servs.,
Inc. v. M-I LLC, 514 F.3d 1244, 1250 (Fed. Cir. 2008) (quoting United
States v. Dunkel, 927 F.2d 955, 956 (7th Cir. 1991) (“Judges are not like
pigs, hunting for truffles buried in briefs.”)).
.

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cannot be established by attacking references individually where the
rejection is based upon the teachings of a combination of references.” In re
Merck & Co., Inc., 800 F.2d 1091, 1097 (Fed. Cir. 1986). Appellant has not
persuaded us that, after reading Gruffaz, those of skill in the art would not
have found it obvious to use triflic acid instead of sulfuric acid.
Appellant argues that the process taught in Gruffaz requires a polar
aprotic solvent, but that the modification of the process taught in Bruson to
achieve the claimed process would selectively adopt the catalyst and not the
solvent. (App. Br. 4). Again, Appellant has not directed us to evidence
sufficient to support the argument. “Argument of counsel cannot take the
place of evidence lacking in the record.” Meitzner v. Mindick, 549 F.2d 775,
782 (CCPA 1977). We do not read Gruffaz as being specifically limited to a
particular solvent, but as providing examples of solvents that are useful.
(See Gruffaz col. 2, ll. 6-8). Furthermore, nothing in the claimed process
excludes the use of a polar aprotic solvent. Thus, Appellant has not
provided us with persuasive arguments that those of skill in the art would not
have found the claimed process obvious.
Appellant attempts to rebut the Examiner’s prima facie case for
obviousness by arguing that the claimed process produces unexpected
results. Appellant points to the 0.8 to 1.3 molar ratio of carboxylic acid to
DCPD when triflic acid is used as an unexpected result because Bruson
teaches using a three to four-fold excess of carboxylic acid. (App. Br. 8). In
addition, Appellant points to the ability to use crude DCPD instead of high-
purity DCPD, which is more costly, when triflic acid is used. (App. Br. 8).
Finally, Appellant argues that nothing in the prior art would lead skilled
artisans to expect that the stringent isomer composition and odor
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requirements of the fragrance industry would be met by using triflic acid.
(App. Br. 8-9).
“It is well settled that unexpected results must be established by
factual evidence. Mere argument or conclusory statements in the
specification does not suffice.” In re De Blauwe, 736 F.2d 699, 705 (Fed.
Cir. 1984) (citing In re Lindner, 457 F.2d 506 (CCPA 1972)). Appellant has
not provided sufficient evidence to support the attorney statements about
what those of skill in the art would have expected with triflic acid.
Accordingly, we are not persuaded that there are unexpected results to rebut
the Examiner’s prima facie case for the obviousness of the claimed process.
VI. CONCLUSIONS
It would have been obvious for those of skill in the art to use triflic
acid in a reaction with DCPD based on the teaching of Gruffaz to use triflic
acid in a reaction with ethylene.
Because Appellant has failed to persuade us that the Examiner’s
prima facie case for obviousness is flawed or can be rebutted, the Examiner
did not err in rejecting the claims under 35 U.S.C. § 103(a).
VII. ORDER
Upon consideration of the record and for the reasons given the
rejection of claims 1-20 under 35 U.S.C. § 103(a) over Bruson and Gruffaz
is AFFIRMED.
FURTHER ORDERED that no time period for taking any subsequent
action in connection with this appeal may be extended under
37 C.F.R. § 1.136(a).
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AFFIRMED

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