Ex Parte Broell

Patent Trial and Appeal Board

Sep 17, 2013

12517563 (P.T.A.B. Sep. 17, 2013)

1
UNITED STATES PATENT AND TRADEMARK OFFICE
__________

BEFORE THE PATENT TRIAL AND APPEAL BOARD
__________

Ex parte DIRK BROELL
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Appeal 2012-005956
Application 12/517,563
Technology Center 1600
__________

Before ERIC GRIMES, JOHN G. NEW, and SHERIDAN K. SNEDDEN,
Administrative Patent Judges.

SNEDDEN, Administrative Patent Judge.

DECISION ON APPEAL
This appeal1 under 35 U.S.C. § 134 involves claims 1-6 and 8-16. The
Examiner entered rejections under 35 U.S.C. § 103(a). We have jurisdiction
under 35 U.S.C. § 6(b).
We affirm.

1 Appellant identifies the Real Party in Interest as Evonik Roehm GmbH.
(App. Br. 1).
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STATEMENT OF THE CASE
Claims 1, 9 and 15 are representative and read as follows (emphasis
added):
1. A process for preparing unsaturated carboxylic
anhydrides of general formula I
R-C(O)-O-C(O)-R (I)
in which R is an unsaturated organic radical having 2 to
12 carbon atoms
comprising transanhydridizing an aliphatic carboxylic
anhydride with a carboxylic acid of general formula II
R-COOH (II)
in which R is as defined above, in an apparatus
comprising a reaction region and a rectification column,
wherein
a) the reactants are fed into a reaction region in
stoichiometric ratios,
b) the carboxylic acid formed as a by-product is removed
from the reaction mixture,
c) the carboxylic anhydride of the formula I is
subsequently drawn off,
d) the unconverted reactants are recycled into the
reaction region,
e) the reaction region comprises a heterogeneous
catalyst and
f) one or more polymerization inhibitors are added.

9. The process according to Claim 1, wherein said
transanhydridization is conducted at a temperature of from 30
to 120° C.

15. The process according to Claim 1, wherein said catalyst is
in an amount of 1/100 up to 1/1 of said reaction region.

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The sole rejection on appeal is the Examiner’s rejection of claims 1-6
and 8-16 under 35 U.S.C. §103(a) over the combination of Bott,2 Hey3 and
Dupont.4
FINDINGS OF FACT
The following findings of fact (“FF”) are supported by a
preponderance of the evidence of record.
FF1. Bott discloses that
The transanhydridization reaction takes place essentially
in the centre section KM of the column K, specifically between
the acetic anhydride and carboxylic acid II feedstocks
conducted in counter-current. According to the drawing, the
acetic anhydride as the lower-boiling component is introduced
into the column K in the lower region, and the higher-boiling
carboxylic acid II in the upper region, of KM.
In order to be able to convert the carboxylic acid II
substantially completely to the anhydride I, it has to be ensured
that the unconverted reactants, by virtue of appropriate
distillation intensity, arrive from the upper section Ko and from
the lower section Ku back in the centre region KM of the column
K. . . .
(Bott 5, ll. 11-25.)
FF2. Bott discloses as follows:
Since some of the carboxylic acid II and of the acetic anhydride
also gets into the column section Ko, it is likewise possible here
for a transanhydridization to take place to a minor degree. For
this reason, it is advisable to supply the catalyst in the upper
region of Ko. For experimental purposes, however, it is usually

2 Bott et al., DE 35610035 A1, published Sept. 25, 1986 (our citations are to
the English language translation filed Aug. 17, 2011).
3 Hey et al., U.S. 4,110,372, issued Aug. 29, 1978.
4 Dupont et al. US 2003/0018217 A1, Jan. 23, 2003.
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sufficient to introduce the catalyst into the upper section of KM
together with the carboxylic acid II.
(Bott 6, ll. 4-12.)
FF3. Hey discloses
an improved process for removing formic acid from a crude
mixture thereof with an aliphatic or cycloaliphatic carboxylic
acid having 2 to 16 carbon atoms or with an aromatic
monocarboxylic acid having 6 to 8 carbon atoms by reacting
the formic acid component of the mixture with a carboxylic
anhydride, a compound forming an anhydride with a carboxylic
acid, or a mixture thereof, which comprises carrying out the
reaction at a temperature from about 20° to 300° C in the
presence of an acidic catalyst which is a mineral acid, a sulfonic
acid, an acidic salt of a mineral acid, or a heterogeneous acidic
catalyst selected from the group consisting of acidic ion
exchange resins in the H+ form and acid-activated bentonites
and zeolites.
(Hey col. 2, ll. 31-45.)
FF4. Hey discloses that
Especially appropriate are heterogeneous acidic catalysts such
as acidic ion exchangers or activated bentonites or zeolites, for
example activated montmorillonites or activated bleaching
earths which have been treated in the cold with a mineral acid,
for example hydrochloric or sulfuric acid. After complete
reaction, these catalysts insoluble in the crude carboxylic acid
may be separated from the reaction mixture in a very simple
manner by filtration or centrifugation. They are therefore
especially suitable for a large-scale manufacture.

For a discontinuous operation, the catalysts generally are added
to the reaction mixture in amounts of from 0.01 to 10%,
preferably from 0.1 to 2%, relative to the weight of the crude
carboxylic acids.
(Id. at col. 4, ll. 1-15.)
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FF5. Dupont discloses as follows:
[0033] The reaction temperature is generally between 50 and
120° C. and preferentially between 85 and 105° C.
[0034] The pressure is adjusted as a function of the chosen
reaction temperature. In general, it is between 20 and 200 mm
Hg (0.0267 and 0.2666 bar).
[0035] The reaction may be carried out in “isobar” mode, i.e. by
fixing the pressure and allowing the temperature to change up
to a limit value preferably fixed between 90 and 150° C., or in
“isothermal” mode, i.e. by fixing the temperature and adjusting
the pressure in the plant throughout the reaction so as to
maintain this pressure.

OPINION
Issue
The issue presented is: Does the evidence of record support the
Examiner’s finding that the combined prior art renders obvious the process
of claims 1, 9 and 15?
Principles of Law
In KSR Int’l v. Teleflex Inc., 550 U.S. 398, 415 (2007), the Supreme
Court rejected a rigid application of a teaching-suggestion-motivation test in
the obviousness determination. The Court emphasized that “the
[obviousness] analysis need not seek out precise teachings directed to the
specific subject matter of the challenged claim, for a court can take account
of the inferences and creative steps that a person of ordinary skill in the art
would employ.” Id. at 418. Thus, an “[e]xpress suggestion to substitute one
equivalent for another need not be present to render such substitution
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obvious.” In re Fout, 675 F.2d 297, 301 (CCPA 1982). See also KSR, 550
U.S. at 401 (“The Court [in United States v. Adams, 383 U.S. 39, 40 (1966)]
recognized that when a patent claims a structure already known in the prior
art that is altered by the mere substitution of one element for another known
in the field, the combination must do more than yield a predictable result.”)
Analysis
Claim 1
The Examiner finds that “[t]he difference between the process taught
by Bott and that instantly claimed is that Bott teaches the use of the
homogeneous acid catalyst methanesulfonic acid, while the use of a
heterogeneous catalyst is instantly claimed” (Ans. 6). “Hey is cited for his
teaching that a heterogeneous catalyst may be substituted for a homogeneous
one in a transanhydridization reaction” (id. at 10). The Examiner concludes
that
One of ordinary skill in the art would have been
motivated by two factors to modify the process of Bott by using
the resin catalyst of Hey to replace the methanesulfonic acid of
Bott. Firstly, doing so would allow one of ordinary skill in the
art to control where on the column the reaction occurred by
placement of the resin. Such control was a goal of Bott.
Secondly, the use of the heterogeneous catalyst would reduce
both the complexity and cost of the process of Bott by
removing the need for catalyst separation and recovery. There
would have been a reasonable expectation for success based on
the similarity of the chemistry involved in the processes of Bott
and Hey.
(Id. at 6-7.)
Appellant contends that “[b]y use of a heterogeneous catalyst, in a
static fashion, the basic principle of operation of the counter-current flow of
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Bott is destroyed” (Reply Br. 2). Appellant contends that “the movement of
the catalyst is concurrent with the movement of the carboxylic acid” and
“[s]ince the movement of the catalyst is concurrent with the movement of
the carboxylic acid in the process of Bott, it would not have been obvious to
use a heterogeneous catalyst in such a process” (id. at 3).
We are not persuaded by Appellant’s arguments. Bott discloses a
system that relies on counter-current of reactants. As discussed by the
Examiner, however, “[t]he flow of reactants and products is maintained in
the process in which a heterogeneous catalyst is substituted for a
homogeneous one” (Ans. 10). And, while Bott discusses the introduction of
the catalyst in the upper portion of their column (Ko), it appears that the need
for continuous introduction of catalyst at Ko arises merely from the fact that
Bott uses a homogeneous catalyst, which, due to its chemical properties,
flows in a downward direction (see id. at 9).
In view of the above, we are not persuaded that the ordinary artisan
would not have found it obvious to substitute Bott’s homogeneous catalyst
with a heterogeneous catalyst as disclosed by Hey. Rather, we find that the
Examiner has expressed a proper reason for the combination of Bott and
Hey, namely, the simple substitution of one known element for another that
appears to do no more than yield a predictable result.

Claim 9
The Examiner finds that “[s]ince the materials and pressures
employed by Bott correspond to those instantly employed, the Examiner
presumes that the temperatures correspond as well” (Ans. 6). The Examiner
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further finds that “Bott teaches … the reaction of methacrylic acid and acetic
anhydride at 30 mbar” and finds that “Dupont teaches (Para [0033]-[0035])
that distillation at this pressure produces the instantly claimed temperatures”
(Ans. 11).
Appellant contends that
Claims 9-11 are separately patentable since there is no
disclosure in the cited art of any temperature range for
conducting the transanhydridization reaction and therefore do
not suggest operating at a reaction temperature within the range
of 30-120°C. Nowhere in the reference is a reaction
temperature disclosed. Although the reaction is conducted
under distillative conditions, there is no specification of a
specific temperature with a specific substrate or pressure such
that a temperature range of 30-120°C is not suggested.
(App. Br. 9-10).
We are not persuaded by Appellant’s argument because it fails to
adequately rebut the Examiner’s reliance on Dupont to suggest that Bott’s
distillation process performed at 30mbar would have inherently been
conducted at a temperature of between 30-120° C. See, e.g., In re Spada,
911 F.2d 705, 708 (Fed. Cir. 1990) (“[W]hen the PTO shows sound basis for
believing that the products of the applicant and the prior art are the same, the
applicant has the burden of showing that they are not.”). See also, In re
Rijckaert, 59 F.3d 1531 (Fed. Cir. 1993); In re Newell, 891 F.2d 899, 901
(Fed. Cir. 1989); In re Napier, 55 F.3d 610, 613 (Fed. Cir. 1995)). In any
event, temperature is a well-known reaction condition (see FF5), and “where
the general conditions of a claim are disclosed in the prior art, it is not
inventive to discover the optimum or workable ranges by routine
experimentation.” In re Aller, 220 F.2d 454, 456 (CCPA 1955).
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Claim 15
The Examiner finds that
Bott, not Hey, is relied upon for his teaching of the reaction
apparatus and Bott clearly sets forth (See figure in abstract) a
reactor in which the reaction region corresponds to one third of
the column volume which lies within the instantly claimed
range of 1/100 up to 1/1. The reaction region in the process in
which heterogeneous catalyst replaces homogeneous catalyst as
set forth in the rejection of record necessarily has a 1/1 volume
ratio of catalyst to reaction volumes since reaction occurs on the
spatially-fixed catalyst.
(Ans. 11.)
Appellant’s arguments do not specifically address the Examiner’s
finding that Bott as modified by Hey would result in a process where the
catalyst is present in an amount of 1/100 up to 1/1 of said reaction region
(see App. Br. 10). Rather, Appellant’s additional arguments address the
cited reference individually, not the combined teachings of the references,
and thus fail to persuade us that the subject matter of claim 15 is non-
obvious. See In re Merck & Co. Inc., 800 F.2d 1091, 1097 (Fed. Cir. 1986)
(Each reference “must be read, not in isolation, but for what it fairly teaches
in combination with the prior art as a whole.”). We further note that Hey
discloses the use of catalysts in amounts of 0.01 to 10% relative to the
weight of the carboxylic acid reactan, which reasonably appears to be
encompassed by the claims (FF4). We are therefore not persuaded by
Appellant’s arguments to the contrary.
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SUMMARY
We affirm the Examiner’s rejection of claims 1-6 and 8-16 under 35
U.S.C. §103(a) over the combination of Bott, Hey, and Dupont.
TIME PERIOD FOR RESPONSE
No time period for taking any subsequent action in connection with
this appeal may be extended under 37 C.F.R. § 1.136(a).

AFFIRMED

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