Ex Parte HOSHINO et al

Board of Patent Appeals and Interferences

Nov 30, 2011

11850784 (B.P.A.I. Nov. 30, 2011)

UNITED STATES PATENT AND TRADEMARK OFFICE
__________

BEFORE THE BOARD OF PATENT APPEALS
AND INTERFERENCES
__________

Ex parte MASAHIRO HOSHINO,
HAJIME ISHIDA, and TATSUYA SUZUKI
__________

Appeal 2010-009141
Application 11/850,784
Technology Center 1600
__________

Before TONI R. SCHEINER, DEMETRA J. MILLS, and
LORA M. GREEN, Administrative Patent Judges.

GREEN, Administrative Patent Judge.

DECISION ON APPEAL
This is a decision on appeal under 35 U.S.C. § 134 from the
Examiner‟s rejection of claims 1-7. We have jurisdiction under 35 U.S.C.
§ 6(b).
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STATEMENT OF THE CASE
Claim 1 the only independent claim on appeal, reads as follows:
1. A process for producing cycloalkanol and/or cycloalkanone,
which comprises oxidizing cycloalkane with molecular oxygen at 25
to 140°C in the presence of mesoporous silica containing the group 8
and/or 9 element in the periodic table, wherein the content of
phosphorus atom in the mesoporous silica is 0 to 4 mol% based on
silicon atom.

The following grounds of rejection are before us for review:
Claims 1-7 stand rejected under 35 U.S.C. 103(a) as being rendered
obvious by the combination of Carvalho
1
and Liu.
2

We affirm.
ISSUE
Does the preponderance of the evidence of record support the
Examiner‟s conclusion that the combination of Carvalho and Liu renders the
process of claim 1 obvious?

FINDINGS OF FACT
FF1 The Examiner‟s statement of the obviousness rejection may be found
at pages 3-4 of the Answer. As Appellants do not argue the claims
separately, we focus our analysis on claim 1, and claims 2-7 stand or fall
with that claim. See 37 C.F.R. § 41.37(c)(1)(vii).

1
Carvalho et al., Iron and copper immobilised on mesoporous MCM-41
molecular sieves as cataysts for the oxidation of cyclohexane, 144 J.
MOLECULAR CATALYSIS A: CHEMICAL 91-99 (1999).
2
Liu et al., Liquid-Phase Oxidation of Cyclohexane Using Co-P-MCM-41
Catalyst, 15 KOREAN J. CHEM. ENG., 510-515 (1998).
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FF2 The Examiner finds that Carvalho teaches a process of oxidizing
cyclohexane to cyclohexanone and cyclohexanol using a Fe-MCM-41, a
mesoporous silica-containing catalyst (Ans. 3).
FF3 The Examiner notes that Carvalho “does not teach a silicate
containing cobalt” (id. at 4).
FF4 The Examiner finds that Liu teaches the oxidation of cyclohexane
using molecular oxygen as the oxidizing agent, as well as using a cobalt
containing MCM-41 catalyst (id.).
FF5 The Examiner also finds that Liu teaches “that reaction intermediates
such as cyclohexanone and cyclohexanol are produced in large quantities”
(id. at 5).
FF6 Liu tested different amounts of the Co-P-MCM-41 catalyst in
studying the oxidation of cyclohexane (see Liu, pp. 512-513, “Catalytic
Activity”). I n Run 2, using 0.25 g of Co-P-MCM-41 catalyst, Liu notes that
“the reaction intermediates, such as cyclohexanone and cyclohexanol, had a
larger amount in proportion than adipic acid during the reaction” (id. at 512,
second column).
FF7. The product distribution of the reaction is shown in Figure 5 of Liu,
reproduced below:
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(Id. at 513.)
FF8. The graph demonstrates that cyclohexanol and cyclohexanone are
major products of the Run 2 reaction.
FF9. Liu concludes that the results from the three runs “suggest that there
should be an optimal amount of catalyst required for the oxidation of
cyclohexane to produce an optimal yield of adipic acid” (id. at 514, second
column).
FF10. The Examiner concludes that
In view of the combined reference teachings, it would have
been obvious to a person having ordinary skill in the art . . . that
transition metals such as cobalt, iron, copper, etc., can be
substituted in MCM-41 silicates, and using a known oxidizing
agent such as molecular oxygen or hydrogen peroxide, such a
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person would have had a reasonable expectation of providing a
catalyst that would catalyze the oxidation of cyclohexane to the
corresponding alcohol and/or ketone.

(Ans. 4.)
FF11. The Examiner also notes that claim 1 does not limit the metal to
cobalt (id. at 5), and thus “the primary difference between the claims on
appeal and the disclosure of Carvalho . . . is that Carvalho . . . teach[es]
hydrogen peroxide as the oxidizing agent, while the instant claims recite the
use of molecular oxygen” (id. at 4-5).
FF12. The Examiner thus concludes further that “[a] person having ordinary
skill in the art would have reasonably expected to substitute one for the other
and still successfully oxidize cyclohexane to cyclohexanone and/or
cyclohexanol” (id. at 6).

PRINCIPLES OF LAW
“The combination of familiar elements according to known methods
is likely to be obvious when it does no more than yield predictable results.”
KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 416 (2007).
If a person of ordinary skill can implement a predictable
variation, § 103 likely bars its patentability. For the same
reason, if a technique has been used to improve one device, and
a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the
technique is obvious unless its actual application is beyond his
or her skill.

Id., at 417. In determining whether obviousness is established by combining
the teachings of the prior art, “the test is what the combined teachings of the
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references would have suggested to those of ordinary skill in the art.” In re
Keller, 642 F.2d 413, 425 (CCPA 1981). In addition, a reference disclosure
is not limited only to its preferred embodiments, but is available for all that it
discloses and suggests to one of ordinary skill in the art. In re Lamberti, 545
F.2d 747, 750 (CCPA 1976).

ANALYSIS
Appellants argue that while Carvalho discloses liquid phase oxidation
with aqueous hydrogen peroxide in the presence or iron or copper
mesoporous metallosilicates, the reference fails “to disclose or suggest (i)
oxidixing cyclohexane with an oxygen containing gas, and (ii) a silicate
containing cobalt” (App. Br. 9). Appellants assert further that while Liu
discloses the testing of a Co-P-MCM-41 catalyst for a one step liquid
oxidation of cyclohexane to adipic acid, Liu does not “disclose or suggest
what kind of catalyst should be preferably used in the production of
cycloalkanol and/or cycloalkanone, as targeted by the present invention”
(id.). Appellants assert that the combination of Carvalho and Liu is a “mere
demonstration that all of the elements of the presently claimed invention are
independently known,” which is impermissible under KSR (App. Br. at 10).
Appellants further assert that “the Examiner fails to identify any reason that
would have prompted one of ordinary skill in the art to combine the
elements in the way Applicants have done” (id.).
Appellants also argue that the object of Liu is a one step oxidation of
cyclohexane to adipic acid, and while Liu teaches that cyclohexanol and
cyclohexanone are formed as reaction intermediates, Liu teaches that such
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intermediates are undesirable (id.). Appellants argue that in the present
invention, “adipic acid is a by-product which forms as a result of further
oxidizing cycloalkanol and/or cycloalkanone” (id.). Thus, Appellants assert,
one desiring to produce cycloalkanol and/or cycloalkanone would avoid the
catalysts of Liu since Liu discloses that the catalyst is used in the production
of an undesired by-product (adipic acid) at the expense of desired products
(cycloalkanol and/or cycloalkanone) (id. at 11). Specifically, according to
Appellants:
[A]ccording to the present invention, the selectivity for
cyclohexanone and cyclohexanol ranges from 80.6-84.0%. See,
Table 1, at page 14 of the specification as filed. In this regard,
Appellants note that Liu et al. discloses that the first stage of the
commercial method of producing adipic acid, discussed above,
has a selectivity for cyclohexanone and cyclohexanol of 80%
when cobalt naphthenate or cobalt octate is used as the catalyst.
Thus, one of ordinary skill in the art would not expect that the
use of the MCM-41 catalyst of Liu et al. would result in a high
selectivity for cyclohexanone and cyclohexanol, as presently
claimed. Rather, it appears that one skilled in the art would be
motivated to use cobalt naphthenate or cobalt octate given Liu
et al.‟s disclosure, not the MCM-41 catalyst as the Examiner
asserts.

(Reply Br. 5.)
Appellants‟ arguments have been carefully considered, but are not
found to be convincing. First, as noted by the Examiner (FF 11), the
primary difference between the process of claim 1 and Carvalho is the
requirement of molecular oxygen as the oxidant, rather than hydrogen
peroxide as taught by Carvalho. We agree with the Examiner that the use of
either hydrogen peroxide or molecular oxygen as the oxidant would have
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been prima facie obvious, especially in view of the teachings of Liu that
molecular oxygen may be used in the oxidation of cycloalkanone.
Second, to the extent that the Examiner relies on Liu for teaching a
cobalt containing catalyst, while the primary focus of Liu is the production
of adipic acid, Liu also teaches that cyclohexanol and/or cyclohexanone are
also major oxidation products under certain reaction conditions (see, eg., FFs
5-8). Liu concludes further that there should be an optimal amount of
catalyst required for the oxidation of cyclohexane to produce an optimal
yield of adipic acid (FF9). Thus, the ordinary artisan, desiring to produce
cyclohexanol and/or cyclohexanone as taught by Carvalho, would also
understand that there should also be an optimal amount of catalysts and
optimal run time to produce an optimal yield of those products. See, e.g.,
Merck & Co. Inc. v. Biocraft Laboratories Inc., 874 F.2d 804, 807 (Fed. Cir.
1989) (“[I]n a section 103 inquiry, „the fact that a specific [embodiment] is
taught to be preferred is not controlling, since all disclosures of the prior art,
including unpreferred embodiments, must be considered.‟”).
Moreover, claim 1 does not require that the reaction produce a high
selectivity for cyclohexanol and/or cyclohexanone, but merely is drawn to a
process of producing cyclohexanol and/or cyclohexanone. Liu, while
desiring adipic acid as the final product, does also teach a process that
produces cyclohexanol and/or cyclohexanone, even if in the method of Liu
those compounds are undesired reaction intermediates.
Finally,
In order for a showing of “unexpected results” to be
probative evidence of non-obviousness, it falls upon the
applicant to at least establish: (1) that there actually is a
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difference between the results obtained through the claimed
invention and those of the prior art . . .; and (2) that the
difference actually obtained would not have been expected by
one skilled in the art at the time of invention.

In re Freeman, 474 F.2d 1318, 1324 (CCPA 1973) (citations omitted).
While Appellants assert that the reaction disclosed in the Specification has a
selectivity for cyclohexanone and cyclohexanol ranging from 80.6-84.0%,
Appellants do not assert that selectivity is unexpected, nor do Appellants
point to evidence or data demonstrating that the results are unexpected when
compared to the closest prior art.

CONCLUSION OF LAW
We conclude that the preponderance of the evidence of record
supports the Examiner‟s conclusion that the combination of Carvalho and
Liu render the process of claim 1 obvious. We thus affirm the rejection of
claim 1 under 35 U.S.C. 103(a) as being rendered obvious by the
combination of Carvalho and Liu. As claims 2-7 stand or fall with claim 1,
we affirm the rejection as to those claims as well.

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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