Dow Global Technologies LLC

Patent Trials and Appeals Board

Oct 8, 2021

2020006222 (P.T.A.B. Oct. 8, 2021)

UNITED STATES PATENT AND TRADEMARK OFFICE
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
APPLICATION NO. FILING DATE FIRST NAMED INVENTOR ATTORNEY DOCKET NO. CONFIRMATION NO.
15/564,543 10/05/2017 Jessica L. Klinkenberg 77653-US-PCT/
DOW 77653 PA
6095
133320 7590 10/08/2021
The Dow Chemical Company/Dinsmore & Shohl LLP
Fifth Third Center
One South Main Street, Suite 1300
Dayton, OH 45402
EXAMINER
QIAN, YUN
ART UNIT PAPER NUMBER
1738
NOTIFICATION DATE DELIVERY MODE
10/08/2021 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):
daytonipdocket@dinsmore.com
kimberly.koen@dinsmore.com
PTOL-90A (Rev. 04/07)

UNITED STATES PATENT AND TRADEMARK OFFICE
____________

BEFORE THE PATENT TRIAL AND APPEAL BOARD
____________

Ex parte JESSICA L. KLINKENBERG and JOHN R. BRIGGS
____________

Appeal 2020-006222
Application 15/564,543
Technology Center 1700
____________

Before CATHERINE Q. TIMM, JAMES C. HOUSEL, and
JANE E. INGLESE, Administrative Patent Judges.

INGLESE, Administrative Patent Judge.

DECISION ON APPEAL
Appellant1 requests review under 35 U.S.C. § 134(a) of the
Examiner’s final rejection of claims 1–5 and 11.2 We have jurisdiction
under 35 U.S.C. § 6(b).
We REVERSE.

1 “Appellant” refers to the “applicant” as defined in 37 C.F.R. § 1.42.
Appellant identifies Dow Global Technologies LLC as the real party in
interest. Appeal Brief filed June 2, 2020 (“Appeal Br.”), 3.
2 Final Office Action entered January 2, 2020 (“Final Act.”), 1.
Appeal 2020-006222
Application 15/564,543

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CLAIMED SUBJECT MATTER
Appellant claims a catalyst composition useful for catalyzing the
telomerization of butadiene. Appeal Br. 4. Claim 1, the sole pending
independent claim, illustrates the subject matter on appeal, and reads as
follows:
1. A catalyst composition useful for catalyzing the
telomerization of butadiene comprising
a complex comprising
palladium,
a 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-
2,4,8-trioxa-6-phosphaada-mantane ligand, and
a ligand selected from a methoxyoctadiene ligand,
an octadienyl ligand, and a protonated octadienyl ligand.

Appeal Br. 14 (Claims Appendix) (emphasis and spacing added).
REJECTION
The Examiner maintains the rejection of claims 1–5 and 11 under 35
U.S.C. § 103 as unpatentable over Launay3 in view of Brenstrum4 in the
Examiner’s Answer entered July 2, 2020 (“Ans.”).
FACTUAL FINDINGS AND ANALYSIS
Upon consideration of the evidence relied upon in this appeal and
each of the Appellant’s contentions, we reverse the Examiner’s rejection of

3 Launay et al., US 2016/0271601 A1, published September 22, 2016.
4 Brenstrum et al., Phosphaadamantanes as Ligands for Palladium
Catalyzed Cross-Coupling Chemistry: Library Synthesis, Characterization,
and Screening in the Suzuki Coupling of Alkyl Halides and Tosylates
Containing ß-Hydrogens with Boronic Acids and Alkylboranes,
69(22) J. Org. Chem. 7635–7639 (2004).
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claims 1–5 and 11 under 35 U.S.C. § 103 for reasons set forth in the Appeal
and Reply Briefs, and below.
Claim 1 requires the recited catalyst composition to comprise a
complex comprising, in part, palladium and a 1,3,5,7-tetramethyl-6-(2,4-
dimethoxyphenyl)-2,4,8-trioxa-6-phosphaada-mantane ligand.
The Examiner finds that Launay discloses “a catalyst for butadiene
telomerization” comprising palladium acetyl acetonate (Pd(acac)2),
methanol, 1-methoxy-2,7-octadiene, and 1,3,5,7-tetramethyl-6-(2-
methoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane (TMPTPA-OMe).
Final Act. 3 (citing Launay ¶¶ 15–47). The Examiner finds that Launay
does not disclose that the catalyst includes 1,3,5,7-tetramethyl-6-(2,4-
dimethyoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane (TMPTPA-di-OMe),
as recited in claim 1. Final Act. 4.
The Examiner finds, however, that Brenstrum discloses
“phosphaadamantanes as ligands for palladium catalyst[s] comprising
TMPTPA-OMe and 1,3,5,7-tetramethyl-6-(2,4-dimethyoxyphenyl)-2,4,8-
trioxa-6-phosphaadamantane (TMPTPA-di-OMe).” Final Act. 4 (citing
Brenstrum 7635–7636). The Examiner determines that this disclosure in
Brenstrum indicates “the equivalence and interchangeability” of TMPTPA-
OMe and TMPTPA-di-OMe as ligands for palladium catalysts. Ans. 5–6.
The Examiner concludes that it would have been obvious to one of
ordinary skill in the art to substitute the 1,3,5,7-tetramethyl-6-(2,4-
dimethyoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane ligand (TMPTPA-di-
OMe) taught by Brenstrum for the TMPTPA-OMe ligand disclosed in
Launay “as an alternative tertiary phosphine ligand, . . . and one of ordinary
skill in the art would expect to achieve the same beneficial results and same
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function” due to the close structural similarity between TMPTPA-OMe and
TMPTPA-di-OMe. Final Act. 4; Ans. 5, 9–10.
For the reasons expressed by the Appellant (Appeal Br. 8–13) and
discussed below, however, we agree with the Appellant that, on the record
before us, the Examiner does not establish that the relied-upon disclosures of
Launay and Brenstrum would have led one of ordinary skill in the art to
produce a catalyst that comprises palladium and a 1,3,5,7-tetramethyl-6-
(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaada-mantane (TMPTPA-di-
OMe) ligand, as required by claim 1.
Launay discloses a process for preparing a telomerization catalyst
precursor for catalyzing the telomerization of butadiene that comprises
palladium and 1,3,5,7-tetramethyl-6-(2-methoxyphenyl)-2,4,8-trioxa-6-
phosphaadamantane (TMPTPA-OMe). Launay ¶¶ 2, 14, 27, 47.
Brenstrum describes synthesizing a library of tertiary
phosphaadamantane ligands, including three TMPTPA-OMe ligands and a
TMPTPA-di-OMe ligand, and determining the effectiveness of the ligands
in facilitating Suzuki-type coupling of alkyl halides containing β-hydrogens
with boronic acids.5 Brenstrum 7635–7636. More specifically, Brenstrum
discloses that the “[l]igands were tested for their ability to affect the
coupling of 1-bromododecane and phenylboronic acid in the presence of

5 A Suzuki-type coupling reaction “is an organic coupling reaction of an
organohalide with an organoborane to give a coupled product using a
palladium catalyst and base. Boronic acid or boronic ester . . . can be used
as well. This reaction is used to create carbon-carbon bonds to produce
conjugated systems of alkenes, styrenes, or biaryl compounds.” Chemistry
Learner, https://www.chemistrylearner.com/suzuki-reaction.html.
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Pd(OAc)2 and potassium tert-butoxide in dioxane at room temperature.”
Brenstrum 7636.
Brenstrum discloses that a 1,3,5,7-tetramethyl-6-(3-methoxyphenyl)-
2,4,8-trioxa-6-phosphaadamantane (TMPTPA-OMe) ligand yielded 34% of
the desired product, a 1,3,5,7-tetramethyl-6-(4-methoxyphenyl)-2,4,8-trioxa-
6-phosphaadamantane (TMPTPA-OMe) ligand yielded 64% of the desired
product, a 1,3,5,7-tetramethyl-6-(2-methoxyphenyl)-2,4,8-trioxa-6-
phosphaadamantane (TMPTPA-OMe) ligand yielded 71% yield of the
desired product, and a 1,3,5, 7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-
trioxa-6-phosphaada-mantane (TMPTPA-di-OMe) ligand yielded 96% of
the desired product. Brenstrum 7636 (Table 1).
Brenstrum thus discloses experimental data demonstrating that tertiary
phosphaadamantane ligands having very similar structures exhibit
considerable variability in their effectiveness at facilitating palladium-
catalyzed Suzuki-type coupling reactions. Significantly, in this vein,
Brenstrum explains that “a review of the current chemical literature reveals
that while certain phosphines accelerate a particular reaction, the same
phosphine may have little effect on a different palladium-catalyzed cross-
coupling.” Brenstrum 7635. Brenstrum further explains that catalyst
systems incorporating l,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-
phosphaadamantane “allowed for effective Suzuki cross-coupling of a
variety of aryl halides and boronic acids under mild conditions,” but
“attempts to use the ligand in Suzuki couplings of alkyl halides containing
β-hydrogens with alkylboranes have met with less than satisfactory results.”
Brenstrum 7635–7636.
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Therefore, contrary to the Examiner’s determination that Brenstrum
discloses “the equivalence and interchangeability” of TMPTPA-OMe and
TMPTPA-di-OMe ligands for palladium catalysts, Brenstrum’s disclosures
actually demonstrate otherwise, as Appellant argues (Appeal Br. 10–12;
Reply Br. 3), and as explained in the Declaration of Devon Rosenfeld filed
October 31, 2019. Rosenfeld Dec. ¶¶ 5–9 (indicating that “as noted in
Brenstrum, minor structural differences in the phosphine ligands may
completely alter the catalytic activity of the catalyst”).
The Examiner does not address the Rosenfeld Declaration. The
Examiner also does not address Brenstrum’s explicit disclosure that while a
particular phosphine ligand effectively facilitates a certain Suzuki-type
coupling reaction, the same phosphine ligand may have little effect on a
different cross-coupling reaction. Nor does the Examiner address
Brenstrum’s explicit disclosure that minor structural differences in
phosphine ligands significantly impact the effectiveness of the ligands in
facilitating Suzuki-type coupling reactions. The Examiner does not explain
why, in view of these disclosures in Brenstrum, one of ordinary skill in the
art reasonably would have considered a TMPTPA-di-OMe ligand to be
interchangeable with a TMPTPA-OMe ligand for a palladium catalyst
including a further ligand selected from methoxyoctadiene,
octadienyl, and protonated octadienyl, and used to catalyze the
telomerization of butadiene, as recited in claim 1.
Although Brenstrum does disclose that both TMPTPA-OMe and
TMPTPA-di-OMe ligands may be used to facilitate Suzuki-type coupling of
alkyl halides containing β-hydrogens with boronic acids, the Examiner does
not provide objective evidence establishing the art-recognized equivalence
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TMPTPA-OMe and TMPTPA-di-OMe ligands for palladium catalysts used
to catalyze the telomerization of butadiene. See In re Christensen, 82 F.2d
715, 716 (CCPA 1936); see also Graver Tank & Mfg. Co. v. Linde Air
Prods. Co., 339 U.S. 605, 609 (1950) (“In determining equivalents, things
equal to the same thing may not be equal to each other . . . . Consideration
must be given to the purpose for which an ingredient is used in a patent . . .
and the function which it is intended to perform.”); see also MPEP
§ 2144.06(II) (“In order to rely on equivalence as a rationale supporting an
obviousness rejection, the equivalency must be recognized in the prior art,
and cannot be based on applicant’s disclosure or the mere fact that the
components at issue are functional or mechanical equivalents.” (citing In re
Ruff, 256 F.2d 590 (CCPA 1958))).
On the record before us, therefore, the Examiner does not provide
sound technical reasoning supported by objective evidence establishing that
one of ordinary skill in the art reasonably would have expected that a
1,3,5,7-tetramethyl-6-(2,4-dimethyoxyphenyl)-2,4,8-trioxa-6-
phosphaadamantane (TMPTPA-di-OMe) ligand as disclosed in Brenstrum
could be substituted for Launay’s 1,3,5,7-tetramethyl-6-(2-methoxyphenyl)-
2,4,8-trioxa-6-phosphaadamantane (TMPTPA-OMe) ligand to produce a
palladium catalyst including a further ligand selected from
methoxyoctadiene, octadienyl, and protonated octadienyl that would
successfully catalyze the telomerization of butadiene. In re Gordon, 733
F.2d 900, 902 (Fed. Cir. 1984) (“The mere fact that the prior art could be so
modified would not have made the modification obvious unless the prior art
suggested the desirability of the modification.”); see also Belden v. Berk-Tek
LLC, 805 F.3d 1064, 1073 (Fed. Cir. 2015) (“[O]bviousness concerns
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whether a skilled artisan not only could have made but would have been
motivated to make the combinations or modifications of [the] prior art to
arrive at the claimed invention.”).
We, accordingly, do not sustain the Examiner’s rejection of claims 1–
5 and 11 under 35 U.S.C. § 103 as unpatentable over Launay in view of
Brenstrum.

DECISION SUMMARY

Claims
Rejected
35 U.S.C.
§
Reference(s)/Basis Affirmed Reversed
1–5, 11 103 Launay, Brenstrum 1–5, 11

REVERSED