Ex Parte Martin et al

Board of Patent Appeals and Interferences

Jan 22, 2009

10433612 (B.P.A.I. Jan. 22, 2009)

UNITED STATES PATENT AND TRADEMARK OFFICE
__________

BEFORE THE BOARD OF PATENT APPEALS
AND INTERFERENCES
__________

Ex parte FRIEDRICH-GEORG MARTIN, GERHARD NESTLER,
and JURGEN SCHRODER
__________

Appeal 2008-5535
Application 10/433,612
Technology Center 1600
__________

Decided: January 22, 2009
__________

Before DEMETRA J. MILLS, ERIC GRIMES, and FRANCISCO C.
PRATS, Administrative Patent Judges.

PRATS, Administrative Patent Judge.

DECISION ON APPEAL
This is an appeal under 35 U.S.C. § 134 involving claims to a process
of preparing higher methacrylates. The Examiner has rejected the claims as
being non-enabled. We have jurisdiction under 35 U.S.C. § 6(b).
We reverse.
STATEMENT OF THE CASE
Appeal 2008-5535
Application 10/433,612

Claims 1, 2, 4-11, 15, 16, 19, 21-26, and 28-34 are pending and on
appeal (App. Br. 2).1 Claim 1, the only independent claim, is representative
and reads as follows:
Claim 1: A process for preparing higher (meth)acrylates
comprising:
reacting (meth)acrylic acid and an alcohol in the presence
of at least one acidic catalyst and at least one polymerization
inhibitor and in the presence of a solvent which forms an
azeotropic mixture with water, thereby forming a reaction
mixture,
distilling off and condensing the azeotropic mixture, and
separating the condensate into an aqueous phase and an
organic phase, . . . [2]
wherein the higher (meth)acrylates prepared contain not
more than 0.05% by weight of (meth)acrylic acid.

The Examiner cites the following documents as evidence of
unpatentability:
Olah US 3,766,286 Oct. 16, 1973
Gardner US 3,878,261 Apr. 15, 1975
Matsumura et al. US 4,435,594 Mar. 6, 1984
Dougherty et al. US 5,145,989 Sep. 8, 1992
Esch et al. US 5,187,309 Feb. 16, 1993
Bauer, Jr. et al. US 5,877,345 Mar. 2, 1999

Michael B. Smith and Jerry March, March’s Advanced Organic Chemistry
219 (5th ed. 1992).

ENABLEMENT

1 Appeal Brief filed December 21, 2006.
2 The omitted part of the claim recites specific reaction conditions for the
claimed process, which are not relevant to the rejection on appeal.
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Application 10/433,612

ISSUE
Claims 1, 2, 4-11, 15, 16, 19, 21-26, and 28-34, all of the pending
claims, stand rejected under 35 U.S.C. § 112, first paragraph (Ans. 3-10).3
The Examiner states that while the Specification is “enabling for using
sulfonic acid, sulfuric acid, phosphoric acid, alkanesulfonic acids (e.g.
methanesulfonic acid, trifluoromethanesulfonic acid) and arylsulfonic acids
(e.g. benzene- or p-toluene- or dodecylbenzenesulfonic acid or mixtures
thereof) or acidic ion exchangers as the acidic catalyst, [it] does not
reasonably provide enablement for using any acidic catalysts generally” (id.
at 3-4).
Applying the oft-cited factors set forth in In re Wands, 858 F.2d 731,
737 (Fed. Cir. 1988), the Examiner reasons that the claims encompass the
use of any acidic catalyst in the claimed reactions, whereas the prior art and
the Specification disclose that only certain acids are useful as catalysts in the
type of reaction claimed (Ans. 4-5). The Examiner contends that the
Specification provides only limited guidance, that the claimed invention
resides in an unpredictable art, and that therefore “a person of skill in the art
would have to engage in undue experimentation to test which acidic catalyst
can be employed to produce the desired claimed compound encompassed in
the instant claims, with no assurance of success” (id. at 10).
Appellants contend that, as disclosed in the Specification, “the
preparation of higher (meth)acrylates by acid-catalyzed esterification of
(meth)acrylic acid with corresponding alcohols in the presence of an
inhibitor or inhibitor system and, if required, of a solvent, is generally

3 Examiner’s Answer mailed July 20, 2007.
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known” (App. Br. 4). Thus, Appellants argue, the gist of the claimed
invention is not the use of any particular acid catalyst, but instead “lies in the
timing of addition of various components and the conditions extant during
said addition” (id. at 5).
Appellants further argue that the “Examiner fails to appreciate that the
disclosure is directed to persons skilled in the art,” and that because “the
fundamental acid-catalyzed reaction of (meth)acrylic acid and an alcohol to
prepare higher (meth)acrylates is generally well-known in the art, it is clear
that one skilled in the art could routinely choose applicable acid catalysts
beyond those specifically listed in the specification herein” (id. at 5-6).
In view of the respective positions advanced by the Examiner and
Appellants, the issue with respect to this rejection is whether the Examiner
erred in concluding that a person skilled in the art would have to resort to
undue experimentation in order to practice the claimed invention using the
full scope of acid catalysts encompassed by the claims.
FINDINGS OF FACT (“FF”)
1. Claim 1 recites a process of preparing higher (meth)acrylates by
reacting (meth)acrylic acid and an alcohol “in the presence of at least one
acidic catalyst,” among other things.
2. Regarding the acid catalyst recited in the claimed process, the
Specification states the following:
Suitable esterification catalysts are the conventional mineral
acids and sulfonic acids, preferably sulfuric acid, phosphoric
acid, alkanesulfonic acids (e.g. methanesulfonic acid,
trifluoromethanesulfonic acid) and arylsulfonic acids (e.g.
benzene-, p-toluene- or dodecylbenzenesulfonic acid) or
mixtures thereof, but acidic ion exchangers are also possible.

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Sulfuric acid, methanesulfonic acid and p-toluenesulfonic acid
and mixtures thereof are particularly preferred.

(Spec. 13.)
3. The reaction mixtures in Appellants’ Examples 1, 6, 8, and 9 contain
hypophosphorous acid and p-toluenesulfonic acid (Spec. 25 and 27-30), and
the reaction mixture in Appellants’ comparative example 4 contains
methanesulfonic acid (Spec. 27).
4. The Examiner acknowledges that processes of esterifying acrylic
acids in the presence of acid catalysts as recited in claim 1 are generally
known in the art, as evidenced by Matsumura (using sulfonic acid cation-
exchange resin as catalyst), Dougherty (sulfuric acid), Bauer (sulfuric acid),
and Esch (strongly acidic cationic resins) (Ans. 5).
5. As evidence of the unpredictability in the art, the Examiner cites
Gardner as disclosing the super acid catalyst SbF5 in combination with
CF3SO3H for isomerizing four to twelve carbon paraffins, and March’s as
disclosing the use of the super acid FSO3H-SbF6 for forming a carbocation
from isobutane, “unlike the claimed process” (id. at 6).
6. As further evidence that the claims encompass acidic compounds that
would not function in accordance with the claimed invention, the Examiner
cites Olah’s disclosure of a number of super acids used for isomerizing
paraffinic and/or alkyl substituted aromatic hydrocarbons (id. at 12).
The Examiner reasons that applying the super acids of Olah to the
claimed process would yield an “unpredictable and completely different
[result] . . . because those super acids had a high likelihood of removing
hydrogen ions from either of the reactants, the acrylic acid and the alcohol,
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instead of helping them to form the desired acrylate product, thereby
detrimentally affecting the yield of the desired final product” (id. at 13).
7. The Examiner states, and Appellants do not dispute, that the pKa of
methanesulfonic acid is -1.9, and the pKa for p-toluenesulfonic acid is -2.8
(id. at 8). Given these facts, the Examiner reasons that
[F]rom this information, it follows that the optimum workable
pKa range for the claimed process is from -1.9 to -2.8.
However, this can not be the representatives for all the pKa
range of the acidic catalysts outside the workable pKa range of
the claimed invention, which would work for the claimed
process. Thus, the specification fails to provide working
examples as to how other types of acidic catalysts can be
resulted in the claimed products, i.e. again, there is no
correlation between the functional language of any acidic
catalyst and the desired final product.

(Id. at 8-9.)
8. The Examiner finds that a skilled artisan in the field of the claimed
invention “would know how to use the taught acid catalyst, but not how to
select other catalyst without trial and error” (id. at 9).
PRINCIPLES OF LAW
The Examiner bears the burden of establishing that practicing the full
scope of the claimed subject matter would have required undue
experimentation. In re Wright, 999 F.2d 1557, 1561-62 (Fed. Cir. 1993)
(“[T]he PTO bears an initial burden of setting forth a reasonable explanation
as to why it believes that the scope of protection provided by that claim is
not adequately enabled by the description of the invention provided in the
specification of the application.”).
“The scope of enablement . . . is that which is disclosed in the
specification plus the scope of what would be known to one of ordinary skill
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in the art without undue experimentation.” National Recovery Technols.,
Inc. v. Magnetic Separation Sys., Inc., 166 F.3d 1190, 1196 (Fed Cir. 1999).
While the Specification must enable the skilled artisan to practice the
full scope of the claimed subject matter, “[i]t is well settled that patent
applicants are not required to disclose every species encompassed by their
claims, even in an unpredictable art.” In re Vaeck, 947 F.2d 488, 496 (Fed.
Cir. 1991). Moreover, a claim does not lack enablement merely because it
encompasses inoperative embodiments. Atlas Powder Co. v. E.I. du Pont
De Nemours & Co., 750 F.2d 1569, 1576 (Fed. Cir. 1984).
For example, in In re Angstadt, 537 F.2d 498 (CCPA 1976), our
reviewing court’s predecessor explicitly recognized that the relevant art was
unpredictable, and that the claim at issue encompassed a number of
inoperative embodiments. Id. at 502. The court nonetheless held that the
claim, which encompassed using thousands of different catalysts, was
enabled, in view of the specification’s disclosure of a large but finite list, and
40 working examples. See id. at 502-503.
Thus, as our current reviewing court has noted:
[T]here must be sufficient disclosure, either through illustrative
examples or terminology, to teach those of ordinary skill how to
make and how to use the invention as broadly as it is claimed.
This means that the disclosure must adequately guide the art
worker to determine, without undue experimentation, which
species among all those encompassed by the claimed genus
possess the disclosed utility.

Vaeck, 947 F.2d at 496 (footnote omitted).
ANALYSIS
We acknowledge the Examiner’s explicit findings in accordance with
the Wands factors. However, we do not agree that the facts presented
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support the Examiner’s conclusion of non-enablement. Rather, we agree
with Appellants that the Examiner erred in concluding that a person skilled
in the art would have to resort to undue experimentation in order to practice
the claimed invention using the full scope of acid catalysts encompassed.
In the instant case, as the Examiner concedes, the Specification
provides a number of different types of acid catalysts suitable in the claimed
esterification reaction (FF 2, 3), and the prior art acknowledges that the
named compounds function as catalysts in the type of reaction claimed (FF
4). In our view, however, the Specification’s disclosure of a variety of
different art-recognized acid catalysts as suitable in the claimed reactions
undermines, rather than supports, the Examiner’s contention that the
Specification provides insufficient guidance to practice the full scope of the
claims.
That is, because the Specification and the prior art apprised a skilled
artisan of the types of compounds useful in the claimed process, the artisan
was informed of the suitable structural and functional properties of
compounds useful as acid catalysts. Moreover, as the Examiner concedes,
because of the art-recognized functional properties of the catalysts, i.e. the
pKa values of the exemplified compounds (see FF 7), the Specification
advised one skilled in the art of suitable pKa ranges for potential catalysts.
Thus, contrary to the Examiner’s position, the Specification as filed
provided the art-informed skilled artisan with structural and functional
guidance regarding compounds that would be suitable as acid catalysts.
Because of that guidance, we do not agree with the Examiner that the skilled
artisan seeking to ascertain suitable acid catalysts for the claimed process
would have needed to experiment unduly.
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As noted above, the Examiner argues that the claims encompass a
number of acid catalysts, including super acids, that would not be expected
to function in the claimed process to yield the claimed product (FF 5, 6).
However, even assuming for argument’s sake that the asserted super acids
would not work in accordance with the claimed process, a claim does not
lack enablement merely because it encompasses inoperative embodiments.
See Atlas Powder, 750 F.2d at 1576.
Thus, even in the relatively unpredictable chemical arts, claims
encompassing numerous species, including inoperative ones, will be enabled
if supported by sufficient guiding disclosure. See Angstadt, 537 F.2d at 502-
503. In the instant case, as discussed above, the Specification and prior art
provide substantial guidance as to the identities and properties of compounds
suitable as acid catalysts in the claimed process. The Examiner’s ability to
provide examples of acids that might not function in accordance with the
claimed invention therefore does not persuade us that the claims are not
enabled.
In sum, we agree with Appellants that the Examiner erred in
concluding that a person skilled in the art would have to resort to undue
experimentation in order to practice the full scope of the claimed invention.
We therefore reverse the Examiner’s rejection of claims 1, 2, 4-11, 15, 16,
19, 21-26, and 28-34 35 U.S.C. § 112, first paragraph.

REVERSED

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cdc
OBLON, SPIVAK, MCCLELLAND MAIER & NEUSTADT, P.C.
1940 DUKE STREET
ALEXANDRIA VA 22314
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