Adnan Al-Hajji et al.Download PDFPatent Trials and Appeals BoardJul 30, 201913181043 - (D) (P.T.A.B. Jul. 30, 2019) Copy Citation 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. Appeal 2018-000793 Application 13/181,043 2 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); Appeal 2018-000793 Application 13/181,043 3 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 Appeal 2018-000793 Application 13/181,043 4 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 Appeal 2018-000793 Application 13/181,043 5 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. Appeal 2018-000793 Application 13/181,043 6 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. Appeal 2018-000793 Application 13/181,043 7 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 Copy with citationCopy as parenthetical citation