Adnan Al-Hajji et al.

Patent Trials and Appeals Board

Jul 30, 2019

13181043 - (D) (P.T.A.B. Jul. 30, 2019)

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.
13/181,043 07/12/2011 Adnan Al-Hajji 211,315 3591
38137 7590 07/30/2019
ABELMAN, FRAYNE & SCHWAB
666 THIRD AVENUE, 10TH FLOOR
NEW YORK, NY 10017
EXAMINER
DOYLE, BRANDI M
ART UNIT PAPER NUMBER
1771
MAIL DATE DELIVERY MODE
07/30/2019 PAPER
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.
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
____________

BEFORE THE PATENT TRIAL AND APPEAL BOARD
____________

Ex parte ADNAN AL-HAJJI, ABDENNOUR BOURANE, and
OMER REFA KOSEOGLU1
____________

Appeal 2018-000793
Application 13/181,043
Technology Center 1700
____________

Before ROMULO H. DELMENDO, CHRISTOPHER C. KENNEDY, and
LILAN REN, Administrative Patent Judges.

KENNEDY, Administrative Patent Judge.

DECISION ON APPEAL
This case is an appeal under 35 U.S.C. § 134(a) from the Examiner’s
decision rejecting claims 1–23. An oral hearing was held on July 25, 2019.
We have jurisdiction under 35 U.S.C. § 6(b). We AFFIRM.
BACKGROUND
The subject matter on appeal relates to processes for removing sulfur-
containing compounds from hydrocarbon feedstocks. E.g., Spec. ¶ 1;
Claim 1. Claim 1 is reproduced below from page 23 (Claims Appendix) of
the Appeal Brief:

1 The real party in interest is identified as the Saudi Arabian Oil Company.
See App. Br. 2.
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1. A method of upgrading a hydrocarbon feedstock by removal of
sulfones and sulfoxides therefrom, which comprises the steps of:
a. supplying a hydrocarbon feedstock to an oxidation reactor,
the hydrocarbon feedstock comprising sulfur-containing
compounds;
b. contacting the hydrocarbon feedstock with an oxidant in the
presence of an aqueous catalyst in the oxidation reactor
under conditions sufficient to selectively oxidize sulfur
compounds present in the hydrocarbon feedstock to produce
a hydrocarbon stream that comprises hydrocarbons and
oxidized sulfur-containing compounds;
c. separating the oxidized sulfur-containing hydrocarbon
stream into an aqueous phase and a non-aqueous oxidized
effluent;
d. recovering the non-aqueous oxidized effluent and contacting
it with an electron donor agent to reduce sulfones and
sulfoxides present in the non-aqueous oxidized effluent for
decomposition by reductive cleavage of carbon-to-sulfur
bonds in the sulfones and sulfoxides to yield by-product salts
and desulfurized hydrocarbons; and,
e. separating the by-product salts and recovering desulfurized
hydrocarbons stream
REJECTIONS ON APPEAL
The claims stand rejected under 35 U.S.C. § 103(a) as follows:
1. Claims 1–14, 21, and 23 over Wallace (US 3,505,210, issued
Apr. 7, 1970) and Schoenebeck (Franziska Schoenebeck et al., Reductive
Cleavage of Sulfones and Sulfonamides by a Neutral Organic Super-
Electron-Donor (S.E.D.) Reagent, 129 J. Am. Chem. Soc. 13368 (2007));
2. Claims 15–20 over Wallace, Schoenebeck, and Karas
(US 7,314,545 B2, issued Jan. 1, 2008);
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3. Claim 22 over Wallace, Schoenebeck, and Kocal (US 7,790,021
B2, issued Sept. 7, 2010).
ANALYSIS
The Appellants argue the claims as a group. We select claim 1 as
representative, and the remaining claims will stand or fall with claim 1.
After review of the cited evidence in the appeal record and the
opposing positions of the Appellants and the Examiner, we determine that
the Appellants have not identified reversible error in the Examiner’s
rejections. Accordingly, we affirm the rejections for reasons set forth below,
in the Final Office Action, and in the Examiner’s Answer.
The Examiner finds, and the Appellants do not contest, that Wallace
teaches a process that falls within the scope of claim 1 except that, relevant
to step (d), Wallace contacts non-aqueous oxidized effluent with an alkali
metal hydroxide and does not expressly state that alkali metal hydroxides are
electron donor agents that reductively cleave carbon-sulfur bonds as recited
by claim 1. Ans. 3–4. The Examiner finds that Schoenebeck “teaches
reductive cleavage of sulfones and sulfonamides with neutral organic
electron donors from tetraazaalkene family,” and that Schoenebeck teaches
that such electron donors “provide a number of advantages” over the use of
alkali metals including that they have “superior selectivity towards mildly
active sulfones” and that they “are mild, neutral reagents, and easily
prepared.” Id. at 4. The Examiner determines that, because “Schoenebeck
teaches an improvement to treating oxidized sulfur compounds in the second
stage of Wallace,” it would have been obvious to substitute Schoenebeck’s
super-electron-donor agent for Wallace’s alkali metal hydroxide “for the
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benefit of improved oxidized sulfur removal using mild, reactive, and easily
prepared reagents.” Id. at 4–5.
With support from the declaration of named inventor Adnan Al-Hajji,
the Appellants argue that “Wallace and Schoenebeck are not properly
combinable” because cleavage by the alkali metal hydroxide of Wallace
takes place by a different reaction mechanism than cleavage by the super-
electron-donor reagents of Schoenebeck. App. Br. 16–17.
That argument is not persuasive. Even accepting the Appellants’
description of the involved reaction mechanisms as accurate, the Appellants
provide no persuasive explanation as to why the differences in reaction
mechanisms would have dissuaded a person of ordinary skill in the art from
substituting one reagent known to cleave carbon-sulfur bonds (Wallace’s
alkali metal hydroxides) for another reagent known to cleave carbon-sulfur
bonds (Schoenebeck’s super-electron-donor reagents). The use of known
elements according to their established functions, or the substitution of one
known element for another, typically does not result in nonobvious subject
matter. See KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 416–21 (2007)
(“The combination of familiar elements according to known methods is
likely to be obvious when it does no more than yield predictable results.”);
see also id. at 416 (“[W]hen a patent claims a structure already known in the
prior art that is altered by the mere substitution of one element for another
known in the field, the combination must do more than yield a predictable
result.”). Wallace states that “[t]he reaction mechanism for the cleavage of
sulfones by alkali metal hydroxides is not clear cut,” Wallace at 5:23–24,
indicating that the specific mechanism by which Wallace’s cleavage reaction
takes place is not critical to Wallace’s process. As the Examiner explains in
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the Answer, the net result of both reaction mechanisms is that C-S bonds are
cleaved “to decompose the oxidized sulfur compounds.” Ans. 9.
The Appellants insinuate that Schoenebeck’s disclosure that super-
electron-donor reagents, rather than “alkali metals,” see Schoenebeck at
13368, can be used for cleavage of sulfur-containing compounds is
irrelevant because Wallace uses alkali metal hydroxides rather than
elemental “alkali metals.” See App. Br. 18. That argument is not persuasive
because Schoenebeck refers to “metal-containing reducing agents” and is not
as narrowly-focused on elemental alkali metals as the Appellants suggest.
See Schoenebeck at 13368. In any event, Wallace itself discloses that alkali
metals are known desulfurization agents, but that they are not desirable due
to cost and difficulties in “regeneration of the alkali metal,” reasonably
indicating that alkali metal hydroxides were known substitutes for elemental
alkali metals. See Wallace at 2:15–25. The record supports the Examiner’s
finding that a person of ordinary skill in the art, in view of Wallace and
Schoenebeck, would have had a reasonable expectation that Schoenebeck’s
super-electron-donor reagent would perform the same function, i.e., cleaving
C-S bonds, as Wallace’s alkali metal hydroxides.
The Appellants also argue that the Examiner’s rejection is
impermissibly based on hindsight because, e.g., (1) Wallace concerns
petroleum desulfurization while Schoenebeck does not, (2) Schoenebeck is
based on laboratory experiments in which other compounds present in
petroleum products would not be present, and (3) Schoenebeck “is not
concerned with an integrated process” that includes the other steps of
claim 1. See App. Br. 19–21.
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Those arguments are not persuasive. As set forth above, the
Examiner’s rejection proposes the substitution of one known C-S bond
cleaving reagent for another, and the references themselves—not
hindsight—indicate the suitability of the substitution. Moreover, the
Examiner identifies benefits disclosed by Schoenebeck that a person of
ordinary skill in the art would have associated with the substitution, see Ans.
4–5, and the Appellants do not meaningfully dispute those benefits.
We understand the Appellants’ argument, in effect, to be that a person
of ordinary skill in the art would not have been certain that Schoenebeck’s
super-electron-donor reagents would function the same way in a commercial
oil refinery (i.e., Wallace) as they did in Schoenebeck’s laboratory
experiments. See App. Br. 20–21. Even if we were to agree that the
references in this case do not provide certainty of success, that argument is
not persuasive because obviousness does not require certainty of success; it
requires only a reasonable expectation of success. PAR Pharm., Inc. v. TWI
Pharm., Inc., 773 F.3d 1186, 1198 (Fed. Cir. 2014) (“The reasonable
expectation of success requirement for obviousness does not necessitate an
absolute certainty for success.”). While the Appellants identify various
factors that would be different in a refinery relative to a controlled
experiment, see App. Br. 20, the Appellants do not persuasively explain why
those differences would have caused a person of ordinary skill in the art to
doubt that Schoenebeck’s reagents would successfully function in Wallace’s
process. Nor do the Appellants dispute the Examiner finding that “[i]t is
within the skill of one in the art to tailor the conditions of the process, i.e.
concentration of super-electron-donor contacted with the feedstock, to
achieve the desired sulfur removal.” Ans. 11.
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On this record, we are not persuaded that the Examiner’s rejection
was impermissibly guided by hindsight.
We have carefully considered the Appellants’ arguments, but we are
not persuaded of reversible error in the Examiner’s rejection of claim 1.
CONCLUSION
We AFFIRM the Examiner’s rejections of claims 1–23.
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