Cytec Industries Inc.

Patent Trials and Appeals Board

Oct 19, 2020

2020000322 (P.T.A.B. Oct. 19, 2020)

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.
14/136,660 12/20/2013 Susie C. Martins 13036S-US-CIP 5615
8015 7590 10/19/2020
CYTEC INDUSTRIES INC.
1937 WEST MAIN STREET
STAMFORD, CT 06902
EXAMINER
JEONG, YOUNGSUL
ART UNIT PAPER NUMBER
1772
NOTIFICATION DATE DELIVERY MODE
10/19/2020 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):
Cheryle.Telesco@solvay.com
StamfordPatent@solvay.com
PTOL-90A (Rev. 04/07)

UNITED STATES PATENT AND TRADEMARK OFFICE
____________

BEFORE THE PATENT TRIAL AND APPEAL BOARD
____________

Ex parte SUSIE C. MARTINS, DOUGLAS A. NAFIS, and
ALAKANANDA BHATTACHARYYA

Appeal 2020-000322
Application 14/136,660
Technology Center 1700
____________

Before ROMULO H. DELMENDO, MICHAEL P. COLAIANNI, and
MICHAEL G. MCMANUS, Administrative Patent Judges.

DELMENDO, Administrative Patent Judge.

DECISION ON APPEAL
The Appellant1 appeals under 35 U.S.C. § 134(a) from the Primary
Examiner’s final decision to reject claims 1, 6–13, 30, and 31.2,3 We have
jurisdiction under 35 U.S.C. § 6(b).
We affirm.

1 We use the word “Appellant” to refer to “applicant” as defined in
37 C.F.R. § 1.42—i.e., “UOP LLC” (Application Data Sheet filed December
20, 2013 at 5). The Appellant identifies “Cytec Industries Inc.” as the real
party in interest (Substitute Appeal Brief filed May 23, 2019 (“Appeal Br.”)
at 2).
2 See Appeal Br. 4–14; Reply Brief filed October 9, 2019 (“Reply Br.”) at
2–6; Final Office Action entered October 1, 2018 (“Final Act.”) at 2–12;
Examiner’s Answer entered August 13, 2019 (“Ans.”) at 3–7, 10–17.
3 Claims 14 and 15 are objected to as depending from a rejected base claim
but are indicated as reciting allowable subject matter (Ans. 8–10).
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I. BACKGROUND
The subject matter on appeal relates to phosphonium-haloaluminate
compounds, which are useful as catalysts in processes for alkylation of
paraffins with olefins (Specification filed December 20, 2013 (“Spec.”) ¶ 2).
Representative claim 1 is reproduced from the Claims Appendix to the
Appeal Brief, as follows:
1. An asymmetric quaternary phosphonium ionic
liquid compound according to Formula (I):

wherein
each of R1-R3 is the same and is chosen from a C3-
C6 alkyl group; and
R4 is chosen from a C4-C12 alkyl group, wherein the
R4 alkyl group contains more carbon atoms than the R1,
R2, and R3 alkyl groups; and
wherein the asymmetric quaternary phosphonium ionic
liquid compound according to Formula (I) provides a higher
Research Octane Number (RON) than ammonium
chloroaluminates when reacting olefins and isoparaffins to
produce high octane alkylates under reaction operating
conditions having a temperature from 20 °C to 70 °C.
(Appeal Br. 15).
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II. REJECTION ON APPEAL
Claims 1, 6–13, 30, and 31 stand rejected under 35 U.S.C. § 103 as
unpatentable over Randolph et al.4 (“Randolph”), as evidenced by Elomari et
al.5 (“Elomari”) (Ans. 3–7, 10–17; Final Act. 2–12).
III. DISCUSSION
1. Grouping of Claims
Unless separately argued pursuant to 37 C.F.R. § 41.37(c)(1)(iv), the
rejected claims stand or fall with claim 1, which we select as representative.
Skeletal arguments based merely on what a claim recites are not arguments
for separate patentability that require our separate consideration. In re
Lovin, 652 F.3d 1349, 1357 (Fed. Cir. 2011).
2. The Examiner’s Position
The Examiner finds that Randolph describes an alkylation catalyst
including a cation that may be a symmetric or asymmetric phosphonium
cation and an anion that may be a halide of a Group IIIA metal including,
e.g., AlCl3 (Ans. 3–4; Final Act. 8–9). According to the Examiner,
Randolph “anticipate[s]” the R1–R4 limitations as recited in claim 1 (Ans. 4;
Final Act. 9 (citing Titanium Metals Corp. v. Banner, 778 F.2d 775 (Fed.
Cir. 1985)). The Examiner states that “[a]lthough Randolph does not
specifically disclose the anion haloaluminate of Al2Cl7[–] as per applicant
claim 1, it is known that ionic liquid comprising quaternary phosphonium
cation and Al2Cl7[–] anion[ is] formed via reacting Lewis acid AlCl3 with a
cation component in the ionic liquid as evidenced by Elomari” (Ans. 4; Final

4 US 2005/0059848 A1, published March 17, 2005.
5 US 2007/0142211 A1, published June 21, 2007.
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Act. 9) (emphases removed)). Regarding the Research Octane Number
(RON) property recited in claim 1, the Examiner states that this property
would necessarily follow from Randolph’s teachings (Ans. 5; Final Act. 10).
As for the Appellant’s argument based on evidence of unexpected results,
the Examiner emphasizes that Randolph discloses asymmetric phosphonium
ionic liquid compounds that are substantially the same as those recited in
claim 1, and, therefore, the argument based on the proffered evidence is
unpersuasive (Ans. 16–17; Final Act. 6–7).
3. The Appellant’s Contentions
The Appellant concedes that “the Office has identified three species of
phosphonium cations in the broad disclosure of Randolph together with an
anion component comprising AlCl3 which might be encompassed by present
[c]laim 1” (Appeal Br. 4).6 The Appellant argues, however, that “the fact
that a claimed species or subgenus is encompassed by a prior art genus is not
sufficient by itself to establish a prima facie case of obviousness” (id. at 4–5
(citing In re Baird, 16 F.3d 380, 382 (Fed. Cir. 1994)). In the Appellant’s
view, the Examiner’s rejection does not follow the steps for analyzing the
broad prior art genus-narrow claimed subgenus-species as set forth in MPEP

6 In the Reply Brief, the Appellant argues belatedly that AlCl3 is mentioned
in the context of mixtures of Bronsted acid and Lewis acid 5)—not an anion
that is part of the ionic liquid 6) (Reply Br. 2). Therefore, the Appellant’s
position in the Reply Brief that AlCl3 is not an anion contradicts the position
set forth in the Appeal Brief (id.). Consequently, we conclude that the
Appellant’s new argument in the Reply Brief has been waived. See
37 C.F.R. § 41.41(b)(2). Even if AlCl3 is, in fact, not an anion, Randolph
teaches AlCl3 as a Lewis acid, which may be used in combination with an
ionic liquid (Randolph ¶¶ 11, 16). Therefore, any error on the part of the
Examiner in this regard is harmless.
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§ 2144.08 (id. at 6). According to the Appellant, the choices of ionic liquids
in Randolph include over 86,000 possibilities (id. at 7–8).
The Appellant also argues that “the combined art fails to suggest
which alkylation catalyst would be successful in solving the technical
problem of having to refrigerate reactors when ionic liquids are utilized in
the alkylation of paraffins with olefins” (id. at 9). The Appellant alleges that
“based on Randolph’s teaching of six chemical classes of alkylation
catalsyts [sic], and of over 86,000 alkylation catalysts based on ionic liquids
alone, Randolph and Elomari . . . fail to provide a small number of
alkylation catalysts that could be easily investigated without undue
experimentation” (id.).
As for Elomari, the Appellant argues that “the only specific class of
ionic liquids disclosed in Elomari . . . is 1-alkyl-pyridinium
chloroaluminates” (id.). The Appellant acknowledges that “while there is a
single mention of phosphonium ionic liquids being suitable for Friedel-
Crafts alkylation in [Elomari’s] Background of the Invention[,]” the
reference “is silent as to the chemical structure of the phosphonium ionic
liquids” (id.).
Furthermore, the Appellant argues that “unexpected advantages are
associated with the presently claimed asymmetric quarternary [sic]
phosphonium chloroaluminates” (id. at 10). In support, the Appellant relies
on Figures 4 and 5 (Drawings filed December 20, 2013) (id. at 10–14).
4. Opinion
We have fully considered the Appellant’s arguments but find that they
fail to identify reversible error in the Examiner’s rejection. In re Jung, 637
F.3d 1356, 1365 (Fed. Cir. 2011).
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Randolph describes an alkylation catalyst composition comprising an
acid component and a polymer, wherein the acid component is selected from
the group consisting of 1) a sulfuric acid, 2) a fluorosulfonic acid, 3) a
perhaloalkylsulfonic acid, 4) an ionic liquid, 5) mixtures of Bronsted acids
and Lewis acids, and 6) combination of any two or more thereof (Randolph
¶¶ 10–11). With respect to the ionic liquid 4), Randolph discloses that it
comprises a cation and an anion, wherein the cation may be selected from
the group consisting of four identified ions and combinations thereof, and
the anion is selected from the group consisting of halides of: Group IIIA
metals, copper, zinc, iron, phosphorus, and combinations thereof (id. ¶¶ 12–
14). One of the four identified cations is described as being a phosphonium
cation having a structure, as follows:

wherein R5, R6, and R7 are selected from saturated and unsaturated
hydrocarbyl groups containing 1–7 carbon atoms, and R8 is also selected
from saturated and unsaturated hydrocarbyl groups containing 1–7 carbon
atoms (id.). In addition, Randolph teaches the inclusion of compounds such
as AlCl3 (id. ¶ 16).
As picking and choosing from Randolph’s disclosure would be
required to arrive at the claimed compound, Randolph does not describe
with sufficient specificity (e.g., exemplify) a catalyst composition containing
a phosphonium cation species that falls within the broad genus of cations
recited in claim 1 and AlCl3. Therefore, we disagree with the Examiner’s
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position that Randolph “anticipate[s]” the R1–R3 and R4 limitations as
recited in claim 1 (Ans. 4; Final Act. 9). Atofina v. Great Lakes Chem.
Corp., 441 F.3d 991, 999 (Fed. Cir. 2006) (“Titanium Metals stands for the
proposition that an earlier species reference anticipates a later genus claim,
not that an earlier genus anticipates a narrower species.”).
The Examiner’s erroneous finding, however, was harmless to the
overall obviousness analysis because Randolph would have reasonably
suggested to a person having ordinary skill in the art a composition
including: a phosphonium cation in which Randolph’s R5, R6, and R7 are
each identically C3, C4, C5, or C6 alkyl and R8 is C4, C5, C6, or C7 where R8
has a greater number of carbon atoms than R5–R7; and AlCl3 (Randolph
¶¶ 14, 16). Thus, even if the Appellant is correct that Randolph’s disclosure
encompasses 86,000 possibilities (Appeal Br. 7–8), such a number of
possibilities—where each would reasonably be expected to provide
comparable, successful results in terms of alkylation and product properties
based on structural similarity and use in view of Randolph’s teachings—is
not the same as that involved in Baird in which our reviewing court held that
a “disclosure of millions of compounds does not render obvious a claim to
three compounds, particularly when that disclosure indicates a preference
leading away from the claimed compounds” (emphases added). Baird, 16
F.3d at 383.
Rather, the mere fact “[t]hat the [reference] discloses a multitude of
effective combinations does not render any particular formulation less
obvious.” Merck, 874 F.2d at 807. See also In re Corkill, 771 F.2d 1496,
1500 (Fed. Cir. 1985) (upholding obviousness rejection of claims based on
prior art teaching that “hydrated zeolites will work” in detergent
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formulations, even though “the inventors selected the zeolites of the claims
from among ‘thousands’ of compounds”); In re Arkley, 455 F.2d 586, 587
(CCPA 1972) (plurality) (“picking and choosing may be entirely proper in
the making of a [§] 103, obviousness rejection.”).
As for the Al2Cl7– anion recited in claim 1, the Examiner finds that
Elomari provides evidence that Al2Cl7– anion would be present when an
ionic liquid contains AlCl3 (Ans. 12). In this regard, Elomari discloses that
Al2Cl7– anion would form from AlCl3 in an ionic liquid in which pyridinium
or imidazolium cations are most commonly used but other cations such as
phosphonium cations may also be used (Elomari ¶ 4). Given these facts, we
detect no error in the Examiner’s finding that when AlCl3 is included in
Randolph, it would reasonably appear that Al2Cl7– anion would necessarily
form. The Appellant does not direct us to any evidence to the contrary.
As for the Appellant’s argument that “the combined art fails to
suggest which alkylation catalyst would be successful in solving the
technical problem of having to refrigerate reactors when ionic liquids are
utilized in the alkylation of paraffins with olefins” (Appeal Br. 9), the
Supreme Court of the United States stated that such an approach to
obviousness is incorrect. KSR Int’l Co. Teleflex Inc., 550 U.S. 398, 420
(2007) (“The first error of the Court of Appeals in this case was to foreclose
[an obviousness] reasoning by holding that . . . patent examiners should look
only to the problem the patentee was trying to solve.”). “Under the correct
analysis, any need or problem known in the field of endeavor at the time of
invention and addressed by the [prior art] can provide a reason for
combining the elements in the manner claimed.” Id. See also In re Kemps,
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97 F.3d 1427, 1430 (Fed. Cir. 1996) (the motivation or reason in the prior art
need not be the same as that of the inventor).
With respect to unexpected results, we agree with the Examiner’s
assessment that the evidence is insufficient because Randolph teaches
phosphonium cations that are substantially the same as that recited in claim
1 (Ans. 16–17). Randolph discloses only four possible classes of cations for
the ionic liquid—one of which is a phosphonium cation (Randolph ¶ 12).
The Appellant’s proffered data appear to be limited to a comparison of two
compounds falling within the broad scope of claim 1—namely,
tributylpentylphosphonium chloroaluminate (TBPP) and
tributylhexylphosphonium chloroaluminate (TBHP), which provided a
higher trimethylpentane (TMP)/dimethylhexane (DMH) ratio than
butylpyridinium chloroaluminate (BPy) and l-butyl-3-methylimidazolium
chloroaluminate (BMIM) (Appeal Br. 11–12 (relying on Figs. 4–5)).
Therefore, the relied-upon comparative data do not include a direct
comparison against the closest prior art, which discloses phosphonium
cations. In re Baxter Travenol Labs., 952 F.2d 388, 392 (Fed. Cir. 1991)
(“[W]hen unexpected results are used as evidence of nonobviousness, the
results must be shown to be unexpected compared with the closest prior art .
. . Mere recognition of latent properties in the prior art does not render
nonobvious an otherwise known invention.”).
Moreover, the comparative data are not reasonably commensurate in
scope with the broad scope of claim 1, which encompasses numerous
variations or possible choices in terms of combinations for R1 through R4.
See, e.g., In re Grasselli, 713 F.2d 731, 743 (Fed. Cir. 1983) (“With respect
to appellants’ broad claims to a catalyst with ‘an alkali metal,’ the
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experiments detailed in Friedrich III, being limited to sodium only, are not
commensurate in scope, and are, therefore, insufficient to rebut the prima
facie case.”). Alternatively, claim 1 should have been narrowed to be
commensurate in scope with the proffered showing. In re Harris, 409 F.3d
1339, 1344 (Fed. Cir. 2005).
For these reasons, we sustain the rejection as maintained against claim
1.
The same analysis applies to claims 6–15, for which the Appellant
offers only a skeletal argument (Appeal Br. 5–6). Therefore, we uphold the
rejection as to these claims for the same reasons discussed above.

IV. CONCLUSION
In summary:
Claims
Rejected
35 U.S.C. § Reference(s)/Basis Affirmed Reversed
1, 6–13, 30, 31 103 Randolph, Elomari 1, 6–13, 30, 31

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