Ex Parte Clark et al

Patent Trial and Appeal Board

Sep 15, 2016

13514148 (P.T.A.B. Sep. 15, 2016)

UNITED STA TES p A TENT AND TRADEMARK OFFICE
APPLICATION NO. FILING DATE FIRST NAMED INVENTOR
13/514,148 06/06/2012 Thomas P. Clark
76104 7590 09/19/2016
The Dow Chemical Company/Brooks Cameron & Huebsch
1201 MARQUETTE A VENUE SOUTH, SUITE 400
Minneapolis, MN 55403
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
ATTORNEY DOCKET NO. CONFIRMATION NO.
66892-US-PCT 3622
EXAMINER
NGUYEN, TAMM
ART UNIT PAPER NUMBER
1772
NOTIFICATION DATE DELIVERY MODE
09/19/2016 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):
DOW.DOCKETING@BIPL.NET
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte THOMAS P. CLARK, KEVIN A. FRAZIER,
FRANCIS J. TIMMERS, and BRIAN W. KOLTHAMMER1
Appeal2015-002970
Application 13/514,148
Technology Center 1700
Before JAMES C. HOUSEL, CHRISTOPHER L. OGDEN, and
LILAN REN, Administrative Patent Judges.
OGDEN, Administrative Patent Judge.
DECISION ON APPEAL
Appellants appeal under 35 U.S.C. § 134(a) from the Examiner's final
decision rejecting claims 1, 2, and 6-10 in the above-identified application.
We have jurisdiction pursuant to 35 U.S.C. § 6(b).
We AFFIRM.
1 According to Appellants, the real parties in interest are The Dow Chemical
Company and its wholly owned subsidiary Dow Global Technologies LLC.
Appeal Br. 2.
Appeal2015-002970
Application 13/514,148
BACKGROUND
Appellants' invention relates to "methods for producing alpha-olefins
( a-olefins), and in particular for selectively isomerizing an a-olefin to a
mixture ofbeta-olefins (B-olefins) and ethenolyzing at least a portion of the
B-olefin to an a-olefin." Spec. iJ 1. Claim 1, the sole independent claim, is
representative:
1. A method for producing alpha-olefins comprising:
converting a first alpha-olefin of either a 1-octene or a 1-
nonene, each without polar impurities, to isomers of beta-
olefins of either 2-octene or 2-nonene, respectively, with a
homogeneous catalyst complex to achieve a greater than 90%
conversion of the first alpha-olefin to the isomers of beta-
olefins, and
ethenolyzing at least a portion of the isomers ofbeta-olefins
to propylene and a second alpha-olefin having one less
methylene group than the first alpha-olefin.
Appeal Br. 14 (emphasis added).
The Examiner maintains the following grounds of rejection:
I. Claims 1, 2, and 7-10 are rejected under 35 U.S.C. § 103(a) as
being unpatentable over U.S. Patent No. US 6,355,855 B 1 (issued Mar. 12,
2002) [hereinafter Nguyen] in view of U.S. Patent No. 5,055,628 (published
Oct. 8, 1991) [hereinafter Lin] and Int'l Pub. No. WO 2008/046106 A2
(published Apr. 17, 2008) [hereinafter Schrodi]. Final Action 5-8.
II. Claim 6 is rejected under 35 U.S.C. § 103(a) as being
unpatentable over Nguyen, Lin, and Schrodi, and further in view of
Guisheng Li et al., Ring-substituted Cyclopentadienyltitanium Complexes
(CsH4CR1R2 Ar)2 Ti Cb: Efficient Catalyst Precursors for Stereoselective
Conversion of Terminal Olefins to (2E)-alkenes, 72 J. Molecular Catalysis
Ll5 (1992) [hereinafter Li]. Final Action 8-10.
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Application 13/514,148
Appellants argue the claims as a group. See Appeal Br. 6-12.
Therefore, consistent with the provisions of 37 C.F.R. § 41.37(c)(l)(iv)
(2013), we limit our discussion to independent claim 1, and all other claims
stand or fall together with claim 1.
DISCUSSION
The Examiner finds that Nguyen teaches the step in claim 1 of
"converting a first alpha-olefin ... to isomers of beta-olefins," including all
its limitations, and that Lin and Schrodi teach the step of "ethenolyzing at
least a portion of the isomers ofbeta-olefins." See Final Action 5-8. In
particular, the Examiner finds that Nguyen teaches the use of a
homogeneous catalyst to achieve greater than 90% conversion of the a-
olefin to the isomers of the B-olefins. See id. at 6 (citing Nguyen 3:64-67
("In most cases the 2-alkene will account for at least about 50%, particularly
at least about 60% and up to 70% or more of the internal alkenes formed.")).
The Examiner finds that Nguyen teaches that conversion to internal alkenes
may be "close to 100%," and that the 2-alkene content of this internal alkene
mixture may be "70% or more," which "suggests no upper limit for the 2-
alkene content of the internal olefin product." Answer 6-7. In light of these
findings, the Examiner determines that
at the time of invention, it would have been obvious to one of
ordinary skill in the art to modify the process of Nguyen to
ethenolize the 2-alkenes to produce propylene and a 1-alkene
having one less methylene group than the 1-alkene fed to
isomerization, as taught by Lin and evidenced by Schrodi,
because Lin teaches that the alpha-olefins produced are useful
products.
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Appeal2015-002970
Application 13/514,148
Final Action 7-8 (internal citations omitted). The Examiner further
determines that
it is within the level of one of skill in the art to have modified
the process of Nguyen by utilizing the product of Nguyen in the
process of Lin because Lin teaches that ... a feedstock such as
a product of Nguy en can be further processed to produce
different products such as propylene and a smaller alpha-olefin.
Answer 6.
First, Appellants argue that combining the process of Nguyen with the
teachings of Lin or Schrodi "would render Nguyen unsatisfactory for its
intended purpose," which, according to Appellants, is "to produce internal
alkanes from 1-alkenes." Appeal. Br. 6-7. Appellants also argue that
Nguyen teaches that 1-alkenes are available from refineries, and does not
teach that 1-alkenes may be formed from the process disclosed by Nguyen.
See id. at 7.
We find this argument unpersuasive of reversible error. The
Examiner cites Lin and Schrodi to establish a reason for using the reaction
products of Nguyen to produce 1-alkenes. Appellants have not shown that
Nguy en teaches away from the further processing steps taught by Lin or
Schrodi. See In re Fulton, 391 F.3d 1195, 1201 (Fed. Cir. 2004) (Teaching
away requires a reference to "criticize, discredit, or otherwise discourage the
solution claimed.")
Second, Appellants argue that the combination of Nguy en, Lin, and
Schrodi would "change the principle of operation of Nguyen," which,
according to Appellants, "is isomerization." Appeal Br. 8-9; Reply Br. 6
(citing a dictionary definition of the terms isomerization and isomer).
Appellants argue that "[i]n contrast to Nguyen, Lin is directed toward
preparation of alpha-olefins by ethenolysis." Appeal Br. 9 (citing Lin,
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Application 13/514,148
Title). Moreover, Appellants argue that "Lin explicitly teaches that 'strong
isomerization activity,' as in the unmodified Nguyen process, is not useful in
the ethenolysis process." Id.
We find this argument unpersuasive of reversible error. According to
the Examiner's rejection, see Final Action 6-8, Lin and Schrodi relate to the
second step of "ethenolysing at least a portion of the isomers," which occurs
after the first step of "converting a first alpha-olefin ... to isomers ofbeta-
olefins" as recited in claim 1. See Appeal Br. 14. Thus, Appellants have not
shown how the teachings of Lin and Schrodi regarding the second step teach
away from the use of isomerization in the production of beta-olefins in the
first step.
Finally, Appellants argue that Nguyen, Lin, and Schrodi do not teach
the limitation of claim 1 requiring "greater than 90% conversion of the first
alpha-olefin to the isomers ofbeta-olefins." Id. at 10-12. In particular,
Appellants argue that even with "close to 100% isomerization," conversion
of "up to 70% or more of the internal alkenes" to 2-alkenes does not overlap
with requirement of "greater than 90% conversion." Id. at 11. Appellants
argue that there is only one example (Example 3) in Nguyen that specifically
indicates the proportion of 2-alkene in the mixture of internal alkenes, and
the proportion is only "59% of a 96% isomerization." Id. at 12. Noting that
claim 42 of Nguyen is directed to "forming internal olefin comprised of at
least about 60 mole-% of 2-alkene(s)," Nguyen 12:41-42, Appellants argue
that the difference between the claimed value and the disclosed value of
59% is 1 %; therefore, "the clear meaning and/or required correspondence
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Application 13/514,148
between the specification and claims for '70% or more of the internal
alkenes' is 70% 2-alkene plus 1 % 2-alkene." Reply Br. 8.
We do not find this argument persuasive of reversible error. By its
literal terms, the range of "at least about 60 mole-% of2-alkene(s)" specified
by claim 42 of Nguyen constitutes a range of 60-100%, and claim 42
specifies a much broader set of reaction conditions and potential catalysts
than reflected in Example 3. Moreover, the Examiner's conclusion of
obviousness is based on the fact that Nguyen teaches a range ("up to 70% or
more" of a conversion "close to 100%") that overlaps the range of "greater
than 90% conversion" specified in claim 1. Appellants have not pointed to
any evidence that the prior art teaches away from the range of "greater than
90%," that the catalysts taught by Nguyen are incapable of conversion rates
within the range required by claim 1, or any other factual evidence sufficient
to show that that a person of ordinary skill in the art would not have
considered the range of "70% or more" disclosed by Nguyen to include
"greater than 90% conversion." ivioreover, in the context of rejecting
dependent claim 6, the Examiner found that "Li also discloses high
conversion rates, over 90%, for the isomerization of 1-octene and 1-nonene"
when using a homogeneous catalyst complex. Final Action 9 (citing Li
Tbls. 1, 2). Appellants have not directed our attention to factual evidence
disputing this finding, which supports the Examiner's determination that a
person of ordinary skill in the art would have understood Nguyen as
teaching a range that includes greater than 90% conversion.
Therefore, by a preponderance of the evidence on this appeal record,
we are not persuaded that the Examiner reversibly erred in rejecting claim 1.
For the same reasons, we find no reversible error in the Examiner's decision
to reject claims 2 and 6-10, which depend from claim 1.
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DECISION
The Examiner's decision is affirmed.
No time period for taking any subsequent action in connection with
this appeal may be extended under 37 C.F.R. § l .136(a)(l )(iv).
AFFIRMED
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