Ex Parte Bulick et al

Patent Trial and Appeal Board

Oct 25, 2018

14733016 (P.T.A.B. Oct. 25, 2018)

UNITED STA TES p A TENT AND TRADEMARK OFFICE
APPLICATION NO. FILING DATE FIRST NAMED INVENTOR
14/733,016 06/08/2015 Allen S. Bulick
21898 7590 10/29/2018
ROHM AND HAAS COMPANY
c/o The Dow Chemical Company
P.O. Box 1967
2040 Dow Center
Midland, MI 48641
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.
76422-US-NP 4150
EXAMINER
KEYS,ROSALYNDANN
ART UNIT PAPER NUMBER
1622
NOTIFICATION DATE DELIVERY MODE
10/29/2018 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):
FFUIMPC@dow.com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte ALLEN S. BULICK, SARAH L. HRUBY,
and MUHUNTHAN SATHIOSATHAM 1
Appeal2017-009409
Application 14/733,016
Technology Center 1600
Before RICHARD M. LEBOVITZ, ULRIKE W. JENKS, and JOHN E.
SCHNEIDER, Administrative Patent Judges.
LEBOVITZ, Administrative Patent Judge.
DECISION ON APPEAL
This appeal involves claims directed to a process for converting a
phosphonate to a hydroxyalkyl phosphonic acid utilizing a sulfonated or
phosphonated heterogeneous catalyst. The Examiner rejected the claims as
obvious under 35 U.S.C. § 103. Appellants appeal the rejection pursuant to
35 U.S.C. § 134. We have jurisdiction under 35 U.S.C. § 6(b ). The
rejection is affirmed-in-part.
1 The Appeal Brief ("Br.") 1 identifies Rohm and Haas Company as the real
party in interest.
Appeal2017-009409
Application 14/733,016
STATEMENT OF THE CASE
Claims 1-8 stand finally rejected by the Examiner under 35 U.S.C.
§ 103 as obvious in view of Schumann et al. (Zur Chemie Der 2-
hydroxyethanphosphonsaure, Phosphorus and Sulfur and the Related
Elements, 13(3): 363-370, 1982 ("Schumann")2 and Dow Liquid
Separations, Dowex Ion Exchange Resins, Poweiful Chemical Processing
Tools, 12 pages, June 2002 ("Dow"). Examiner's Answer ("Ans.") 3.
Claim 1, the only independent claim on appeal, is reproduced below:
1. A process for converting a phosphonate, which is a
hydroxyalkyl- or acyloxyalkylphosphonate, to a hydroxyalkyl
phosphonic acid comprising the step of contacting together
water, the phosphonate, and a sulfonated or phosphonated
heterogeneous catalyst under conditions sufficient to convert at
least 50% of the phosphonate to the hydroxyalkyl phosphonic
acid.
REJECTION
Claim 1 recites a process in which a "hydroxyalkyl- or
acyloxyalkylphosphonate" is converted to a "hydroxyalkyl phosphonic
acid". The process comprises contacting the phosphonate with (1) water and
(2) a "sulfonated or phosphonated heterogeneous catalyst". The contacting
is done "under conditions sufficient to convert at least 50% of the
phosphonate to the hydroxyalkyl phosphonic acid."
The Examiner found that Schumann ( on the top of page 3 64)
describes a reaction in which 2-acetoxyethanephosphonic acid dimethyl
ester 2 ( compound 2) - an "acyloxyalkylphosphonate" as required by claim
2 Schumann is a German language document. An English translation
provided by the Examiner is relied upon herein.
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Application 14/733,016
1 - is converted into 2-hydroxyethanephosphonic acid ( compound 1) - a
"hydroxyalkyl phosphonic acid" as also required by claim 1. Final Office
Action ("Final Act.") 6; Ans. 3, 5.
The reaction shown in Schumann is reproduced below: 3
f--4 }~i)(:l!J(:.}{~f~((}}§h
i
l
·. ,, , .. ,.,,. , ,. ~l, ·"-<" ,., • W'.,_·'H,~', lf . , ,, ,, ,,,.,, if ·, "· ,,.,,.), .·~,C h,P,, ,,. h,t·, .................. , ........ ., A,,-,){.~"-·' !-:J,l\fJt1 i-
, '~ -:0..>. .. ..!. \"..i, •,,,~.,, t:t~t:::• \ -<' '1.."., ,A.:,.~\;,'-,,-.;~~ ,r •.S.:,:
, \
_..,.._ ...
\ ('.\
\ ~f ' ,,
\ .. ;, ~··•·j('''J,ri.,J•,Y1:q, · -~·., .t i~:1c..-} 1,i,.~ ...,,v..~ J...r-.0
As shown in the reaction scheme, compound 2, an
acyloxyalkylphosphonate ( the same reactant as in claim 1 ), is converted to
compound 1, a hydroxyalkyl phosphonic acid (the same end product as in
claim 1 ), in the presence of HC1/H20 at 100°C. Schumann discloses that
77% of the resulting product is of compound 1. Schumann 3 64, 1. 1. Thus,
Schumann starts with the same reactant as in claim 1 and produces the same
end product as in claim 1.
The Examiner recognized that Schumann does not describe contacting
compound 2, an "acyloxyalkylphosphonate", in the presence of "a
sulfonated or phosphonated heterogeneous catalyst" as required by claim 1,
but instead utilizes "HC1/H20." Final Act. 3--4; Ans. 3 (see reaction scheme
reproduced above). However, the Examiner found the Dow describes an ion
exchange resin which meets the limitations of the claimed "heterogeneous
catalyst." Final Act. 2-3; Ans. 3--4. The Examiner determined it would
3 Best copy available.
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Appeal2017-009409
Application 14/733,016
have been obvious to one of ordinary skill in the art at the time of the
invention to substitute Dow's ion exchange resin for "HC1/H20" (a soluble
acid) in Schumann's reaction for the advantages described in Dow for such
resins. Final Act. 2-3; Ans. 3--4. The Examiner provided a reasoned
statement as to why it would have been obvious to modify Schumann with
Dow's teaching:
Dow discloses that ion exchange resins can be used in the place
of soluble acids [HC1/H20] in reactions which include
hydrolysis reactions (see entire disclosure, in particular page 4).
The catalysts can be used as acid catalysts at temperatures as
high as 120°C (see page 4 under the heading Stability
Considerations). Advantages offered by the use of Dowex ion
exchange resins as acid catalysts include separation of the
catalyst from the reaction mass is greatly simplified, the resin
catalyst can be used reused repeatedly, greater selectivity of
reaction direction, and easier to handle ( see page 4 under the
heading Advantages).
Final Act. 2-3.
DISCUSSION
Appellants contend that Schumann "does not teach acid catalyzed
conversion of the starting material 2-acetoxyethanephosphonic acid dimethyl
ester or 2-hydroxyethanephosphonic acid dimethyl ester to 2-
hydroxyethanephosphonic acid." Br. 8. Appellants state there is no
teaching by Schumann of the conversion of compound 2 to compound 1 by
"acid catalysis." Id. Rather, Appellants argue that Schumann utilizes a
stoichiometric excess of acid to accomplish the conversion. Id. Appellants
further argue:
Dr. Sathiosatham [a co-inventor] explained in the interview
with Examiners Keys and Fereydoun, he attempted to convert
the ester of Compound 2 to the acid of Compound 1 via
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Appeal2017-009409
Application 14/733,016
hydrolysis using HCl catalysis but gave up when the conversion
didn't work after several attempts. It was only out of
desperation that he tried the ion exchange resin, which, to his
surprise worked beyond his wildest expectations.
Id. at 10.
This argument does not persuade us that the Examiner erred in
rejecting the claims.
First, Appellants have not explained how the "splitting of [ compound]
2 with concentrated hydrochloric acid" in an acidolytic step as disclosed by
Schumann (Schumann 363) differs from "HCl catalysis." Second,
Appellants contend that Dr. Sathiosatham failed "to convert the ester of
Compound 2 to the acid of Compound 1 via hydrolysis using HCl catalysis,"
but provided no objective evidence of the "attempt" nor disclose the failed
conditions of "hydrolysis using HCl catalysis" nor explain how the
conditions utilized by Schumann differ from HCl catalysis. Br. 10.
Appellants have not adequately explained how "HCl catalysis" is any
different from the acidolytic step carried out by Schumann in the presence of
HCl (Schumann 363).
Appellants cite the disclosure in Dow that "Strong Acid Resins are
used in a number of instances as strong acid catalysts in place of soluble
acids." Dow 4 (quoted on Br. 10). Based on this teaching in Dow,
Appellants argue:
Schumann teaches away from using acid catalysis to convert
Compound 2 to Compound 1 in the first place; therefore, there
would be no motivation to replace the acid catalyst that isn't
being used with a catalytic amount of the strong acid resin.
Br. 10.
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Application 14/733,016
We do not agree that Schumann teaches away from utilizing the Dow
resin. As explained by the Examiner, Dow has broad disclosure that its
resins have exchangeable H+ and therefore can be used as "reactive acids."
In this regard, Dow teaches:
Strong Acid Resins. As produced, these resins contain
exchangeable H+ cations which give the resins the ability to
behave as insoluble, but very reactive acids. Not only can these
resins be used to exchange the H+ ion for the cations of a salt in
solution, effectively "salt splitting" and forming the acid of the
salt involved in solution, but they can be used in place of
soluble acid in many catalytic reactions.
Dow 3.
Thus, even if it were true that Schumann's acidolytic step utilizing
HCl is not the same as HCl catalysis, there still would be reason to replace
HCl with the resin of Dow in order to utilize the Dowex resin as a source of
H+ ions instead ofHCl. See Ans. 4:3-7. Dow's ion exchange resin is being
used for its known and expected properties as an acid source. As held in
KSR Int 'l Co. v. Teleflex Inc., 550 U.S. 398, 417 (2007):
[I]f 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 .
. . . [A] court must ask whether the improvement is more than
the predictable use of prior art elements according to their
established functions.
Nonetheless, as explained by the Examiner, because HCl is present in
Schumann's reaction, it is reasonable to believe that it acted as a catalyst for
the reaction. Ans. 5. Again, Appellants have not provided evidence that the
HCl present in Schumann's reaction would not function as a catalyst.
Appellants mention experiments performed by co-inventor Dr.
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Appeal2017-009409
Application 14/733,016
Sathiosatham, but do not direct our attention to a declaration or other
objective evidence describing the details of these experiments so their
relevance to Schumann and Dow cannot be determined.
Appellants also state that Dow "makes it clear that the replacement is
suitable for sulfuric acid catalysts, not HCl catalysts, much less HCl used in
stoichiometric excess, as taught by Schumann." Br. 10. We do not agree.
With regard to sulfuric acid, while Dow mentions its resins as a replacement
for sulfuric acid (Dow 4 ), Dow has broad disclosure teaching that its resins
can be used in place of soluble acids (Dow 3). Thus, contrary to Appellants'
argument, Dow is not limited to replacing sulfuric acid with its ion exchange
resms.
With respect to the "stoichiometric excess" argument, Appellants
have not identified where Schumann teaches such an excess, and even if it
does, how this would teach away from utilizing the Dow ion exchange resin.
Appellants make such statements, but provided no objective evidence that
that the reaction in Schumann, listing HCl above the arrow, does not proceed
by "HCl catalysis" as asserted. As explained above, Dow teaches that its
resin can supply H+ ions, making it obvious (for the reason stated by the
Examiner) to have used it in the place of Schumann's HCl, which also is a
source of H + ions.
Appellants refer to the reaction described in Schumann with water at
160°C. Br. 10. However, the Examiner clearly referred to the reaction
carried out at l00°C utilizing acid. Final Act. 3--4; Ans. 3. Thus,
Appellants' argument has no merit.
Appellants also contend they solved a problem that had not been
recognized and not solved since at least 1982. Br. 11. Appellants state that
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Application 14/733,016
"the sole reliance in the published literature to using a stoichiometric excess
of HCl to convert alkylphosphonate esters to phosphonic acid, unaltered for
40 years in spite of the stated disadvantages of this methodology,
demonstrates a lack of appreciation for a better approach." Id.
This argument is not supported by adequate evidence. Appellants
have not identified the unsolved problem. Schumann converts 2-
acetoxyethanephosphonic acid dimethyl ester 2 (compound 2)-
"acyloxyalkylphosphonate" as recited by claim 1 - into 2-
hydroxyethanephosphonic acid ( compound 1) - "hydroxyalkyl phosphonic
acid" as also recited by the claim. It was not disputed by Appellants that
Schumann produces the same compound which is claimed, starting with the
same reactant as claimed. Thus, the problem of converting
acyloxyalkylphosphonate into a hydroxyalkyl phosphonic acid had already
been solved by Schumann. The only difference is that Schumann uses a
soluble acid a source of H+, while the claims use a known ion exchange resin
as the H+ source. As explained above, utilizing the resin in place of the
soluble acid would have been obvious to one of ordinary skill in the art
because it is using the resin for its known and expected advantages.
Appellants have also not identified the disadvantages of Schumann's
process. As explained by the Examiner:
The Applicants are not the first to discover the problems
associated with the use of soluble acids as catalyst. In the
instant case, Dow discloses that ion exchange resins are easier
to handle than their soluble counterparts (in the instant case that
would be HCI). They do not present the hazard to personnel nor
do they cause severe equipment corrosion ( see item 4 of the
Advantages on page 4 of Dow) .... Thus, one having ordinary
skill in the art at the time the invention was made would have
been motivated to substitute ion exchange resins of Dow for the
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Application 14/733,016
HCI of Schumann for easier handability, safety to personnel
and to avoid equipment corrosion.
Final Act. 3--4.
Appellants further argue:
when one considers the unpredictability of chemical reactions,
it could not be known until the reaction was attempted whether
it would work at all, much less within the scope of the claimed
conversion - greater than 50% for Claim 1, greater than 70% for
Claim 3, and greater than 85% for Claim 8.
Br. 11.
This argument is not persuasive. Schumann teaches that its
conversion reaction results in a product yielding content of 77%. Schumann
364: 1. Furthermore, the Examiner's finding that "the preparation of a
hydroxyalkyl phosphonic acid from a hydroxyalkyl- or acyloxyalkyl
phosphonate by acidolysis or hydrolysis is not an unpredictable reaction" as
evidenced by Schumann's teaching of the success of such reaction is
supported by preponderance of the evidence. Final Act. 4. An argument
made by counsel in a brief does not substitute for evidence lacking in the
record. Estee Lauder, Inc. v. L 'Orea!, S.A., 129 F.3d 588, 595 (Fed. Cir.
1997).
The Examiner also explained why the specific conversion amounts
recited in claims 1 and 3 would have been obvious to one of ordinary skill in
the art:
Further, given the teaching of Dow that the ion exchange resin
can be reused repeatedly, has greater selection of reaction
direction, and leads to reduction or elimination of side
reactions, the skilled artisan at the time the invention was made
would have reasonably expected that the use of the ion
exchange resin of Dow in the process of Schumann would
allow one to obtain higher yields of the desired hydroxyalkyl
phosphonic acid.
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Application 14/733,016
Final Act. 4.
Appellants did not identify a defect in the argument and we find none.
Claims 5-8
Claim 5 recites "wherein methyl acetate and methanol are formed in
addition to the hydroxyalkyl phosphonic acid." The reaction occurs at a
temperature of 80°C to 120°C (see claim 3 from which claim 5 indirectly
depends). Claims 6-8 depend from claim 5. Appellants argued these claims
separately.
The Examiner states that claim 5 would have been obvious because
Dow teaches that methyl acetate and methanol are produced when water and
a temperature of 160°C is used: "One having ordinary skill in the art would
find it obvious that methyl acetate and methanol would also be produced
during the reaction at the top of page 364, since 2 and water are present and
the presence of the hydrochloric acid would allow for the reaction to occur at
the lower temperature." Ans. 10.
The Examiner's argument is not supported by a preponderance of the
evidence. Schumann describes the production of the methyl acetate and
methanol as having "surprisingly" occurred when compound 2 is converted
to compound 1 with water at a reaction temperature of 160°C under
hydrolytic conditions. Schumann 364. The Examiner did not provide
adequate reason why this surprising reaction using water and a temperature
of 160°C would occur at 100°C (as in Schumann) or at 80°C to 120°C (as in
claim 5) in the additional presence of HCl under acidolytic conditions or
using the Dow ion exchange column as the acid source. Because the
Examiner did not meet the burden of establishing that claim 5 is obvious in
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Application 14/733,016
view of Schumann and Dow, we reverse the rejection of claim 5, and
dependent claims 6-8.
SUMMARY
The obviousness rejection of claims 1 and 3 is affirmed. Claims 2 and
4 fall with claims 1 and 3 because separate reasons for their patentability
were not provided. 37 C.F.R. § 4I.37(c)(l)(iv). Thus, the Examiner's
determination that claims 1--4 are unpatentable is affirmed.
The obviousness rejection of claims 5-8 is reversed.
TIME PERIOD
No time period for taking any subsequent action in connection with
this appeal may be extended under 37 C.F.R. § 1.136(a)(l )(iv).
AFFIRMED-IN-PART
11