AL-MALKI, Abdullah R.Download PDFPatent Trials and Appeals BoardDec 2, 201914887912 - (D) (P.T.A.B. Dec. 2, 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. 14/887,912 10/20/2015 Abdullah R. AL-MALKI 0004159.005462 (SA5462) 9191 35979 7590 12/02/2019 Bracewell LLP P.O. Box 61389 Houston, TX 77208-1389 EXAMINER FANG, SHANE ART UNIT PAPER NUMBER 1766 NOTIFICATION DATE DELIVERY MODE 12/02/2019 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): docketing@bracewell.com PTOL-90A (Rev. 04/07) UNITED STATES PATENT AND TRADEMARK OFFICE ____________ BEFORE THE PATENT TRIAL AND APPEAL BOARD ____________ Ex parte ABDULLAH R. AL-MALKI Appeal 2019-001088 Application 14/887,912 Technology Center 1700 ____________ Before JEFFREY B. ROBERTSON, MONTÉ T. SQUIRE, and MICHAEL G. McMANUS, Administrative Patent Judges. McMANUS, Administrative Patent Judge. DECISION ON APPEAL Pursuant to 35 U.S.C. § 134(a), Appellant1 seeks review of the Examiner’s decision to reject claims 1−7. We have jurisdiction under 35 U.S.C. § 6(b). We REVERSE. 1 We use the word “Appellant” to refer to “applicant” as defined in 37 C.F.R. § 1.42. Appellant identifies the real party in interest as Saudi Arabian Oil Company. Appeal Br. 4. Appeal 2019-001088 Application 14/887,912 2 CLAIMED SUBJECT MATTER The present Application generally relates to methods and compositions for manufacturing polymers of thiophene, benzothiophene, and their alkylated derivatives. Spec. ¶ 2. The Application further relates to the separation of thiophene and benzothiophene from a naphtha feed. Id. ¶¶ 6, 9. The Application teaches to manufacture polymers by reacting thiophene, benzothiophene, or their alkylated derivatives with super acids. Id. ¶ 2. Claim 1 is illustrative of the subject matter on appeal and is reproduced below with certain limitations bolded for emphasis: 1. A process for manufacturing a polymer of sulfur-containing heterocyclic compounds, the process comprising the steps of: isolating a sulfur-containing heterocyclic compound from cracked naphtha, comprising the steps of: isolating the cracked naphtha from a reaction product gas stream of a fluid catalytic cracking unit in a distillation column; feeding the cracked naphtha to a secondary distillation column, wherein the sulfur-containing heterocyclic compound is isolated from the cracked naphtha according to a boiling point of the sulfur-containing heterocyclic compound; and polymerizing the sulfur-containing heterocyclic compound with a super acid to produce the polymer of the sulfur-containing heterocyclic compound. Appeal Br. 22 (Claims App’x) (emphasis added). Appeal 2019-001088 Application 14/887,912 3 REFERENCES The Examiner relies upon the following prior art: Name Reference Date Burnett et al. (“Burnett”) US 2006/0081502 Al April 20, 2006 Wang CN202047021U November 23, 2011 Feng et al., (“Feng”) Activation of Thiophenes by Superacids: Protonation and Polymerization, Chemistry of Materials, Vol. 9, No. 3, 641–643 March 1997 REJECTION The Examiner maintains the following rejection: Claims 1–7 are rejected under 35 U.S.C. § 103(a) (pre-AIA) as being unpatentable over Feng in view of Burnett and further in view of Wang. Non-Final Act. (mailed May 19, 2017) 2–4.2 DISCUSSION The Examiner rejects claims 1–7 as obvious over Feng, Burnett, and Wang. Id. In support of the rejection, the Examiner finds that Feng teaches a process of producing polythiophene activated by super acids and using 2 The present claims stand rejected by Final Action dated Oct. 20, 2017 (“Final Act.”). In that action, the Examiner states that “[t]he rejections of claims 1–7 as stated in the previous office action are repeated here as such.” Final Act. 2. Accordingly, we cite to the Non-Final Action (“Non-Final Act.”). Appeal 2019-001088 Application 14/887,912 4 dichloromethane as a solvent for polymerization. Id. at 3. The Examiner further finds that Burnett teaches a process for removal of thiophene by fractionation from crack naphtha. Id. The Examiner additionally finds that Wang teaches to isolate chemicals by extraction. Id. The Examiner further determines that a person of ordinary skill in the art would have had reason to combine the teachings of the references “because the resultant process would yield an environmentally friendly method to produce polythiophene using thiophene monomers from the byproducts of FCC refinery.” Id. at 3–4. The Examiner adds that the “abundant thiophene source taught by Burnette enables producing polythiophene based on Feng’s scheme at manufacturing scale.” Id. at 4. Appellant argues that the rejection is in error. Appeal Brief (filed June 19, 2018) (“Appeal Br.”) 10–20. First, Appellant argues that Burnett does not teach “isolating a sulfur-containing heterocyclic compound from cracked naphtha . . . wherein the sulfur-containing heterocyclic compound is isolated from the cracked naphtha according to a boiling point of the sulfur- containing heterocyclic compound” as required by claim 1. Id. at 13, 15–17. Appellant argues that Burnett teaches only “separating the hydrocarbon feed stream into a stream of light hydrocarbons with reduced organic nitrogen and organic sulfur species and a stream of heavy hydrocarbons with an increased nitrogen content and sulfur content.” Id. at 15 (citing Burnett ¶¶ 72–78). Appellant argues that this is less than the separation of sulfur compounds. Appellant further argues that Burnett teaches that multiple types of sulfur-containing compounds, including mercaptans, may be found in the liquid hydrocarbon feed. Id. at 16. Appeal 2019-001088 Application 14/887,912 5 Appellant argues that “[t]here is no disclosure in Burnett of separating the sulfur-containing heterocyclic compounds from the mercaptans.” Id. In the Answer, the Examiner responds that the “application does not claim or exclude separating sulfur containing heterocyclic compounds from nitrogen species.” Answer (mailed Oct. 2, 2018) 4. The Examiner further determines that the fractioning taught by Burnett would “inherently” separate sulfur containing heterocyclic compounds from mercaptans. Id. The Examiner further finds that “Burnette (48-51, claim 19) particularly discloses a process and apparatus for removing thiophene (bp° 84 °C) by fractionating (using distillation column) from the crack naphtha separated from FCC via fractionating (using distillation column).” Id. Similarly, the Examiner finds that “Burnett (0061) intends to remove high boiling point sulfur and nitrogen compound above 150 °C. Thiophene (bp° 84 °C) appears to be removed by heating. Burnette (48-51, claim 19).” Id. The Examiner’s findings go beyond the teachings of Burnett. Broadly speaking, Burnett teaches to react nitrogen compounds and sulfur compounds in a hydrocarbon feed with an alkylating agent so that the resulting compounds have increased boiling points. See, e.g., Burnett ¶¶ 19– 20. Burnett teaches that nitrogen compounds react with an alkylating agent in a first reaction zone and sulfur compounds react with an alkylating agent in a second reaction zone. Id. The reaction of sulfur compounds and alkylating agent yields “organic sulphur species of higher boiling point and organic nitrogen species of higher boiling point.” Id. ¶ 20. Subsequent to such reaction, Burnett teaches to fractionate the resulting hydrocarbon feed “to remove the organic nitrogen species of higher boiling point and the organic sulphur species of higher boiling point to Appeal 2019-001088 Application 14/887,912 6 generate a liquid hydrocarbon feed comprising a reduced alkylating agent content and a reduced nitrogen and sulphur content.” Id. ¶ 21. In another embodiment, Burnett teaches a process where the alkylated nitrogen compounds are fractionated prior to alkylation of the sulfur compounds. Id. ¶¶ 75–78, Figure 3. The sulfur compounds are then alkylated and the liquid hydrocarbon feed is passed to a second fractionating unit where it is separated into one stream with a lower boiling point range and a decreased sulfur content and a second stream with a higher boiling point range and an increased sulfur content. Id. ¶ 78. Burnett teaches that the sulfur compounds are modified so that they will be a part of the higher boiling fraction. Burnett teaches that the alkylating agent “reacts with the organic sulphur species to produce alk[y]lated organic sulphur species usually having a boiling point of between 100-250° C.” Id. ¶ 57. The Examiner appears to find that this higher boiling fraction necessarily includes the sulfur compounds of the claim. Answer 4. The Examiner, however, does not make any findings regarding alkylated thiophenes (or any other alkylated sulfur-containing compound). Final Act. 3. The Specification teaches that “[e]xamples of the sulfur-containing heterocyclic hydrocarbon include thiophene, which has a boiling point of about 84 °C and benzothiophene, which has a boiling point of about 221 °C” (Spec. ¶ 13), which suggests that in Burnett’s process thiophene would be found in the lower boiling fraction. Burnett, however, describes the lower boiling fraction as “a hydrocarbon feed stream with a lower boiling range and a decreased nitrogen and sulphur content.” Burnett ¶ 74. Absent more, we are not persuaded Burnett’s disclosure in this regard is a clear teaching or Appeal 2019-001088 Application 14/887,912 7 suggestion of the sulfur-containing heterocyclic compound being “isolated from the cracked naphtha,” as required by claim 1. In view of the foregoing, we determine that Appellant has shown error in the Examiner’s finding that Burnett teaches “isolating a sulfur-containing heterocyclic compound from cracked naphtha . . . wherein the sulfur- containing heterocyclic compound is isolated from the cracked naphtha according to a boiling point of the sulfur-containing heterocyclic compound” as required by claim 1. CONCLUSION The Examiner’s rejection of claim 1–7 is reversed. In summary: Claims Rejected 35 U.S.C. § Reference(s)/Basis Affirmed Reversed 1–7 103(a) Feng, Burnett, Wang 1–7 REVERSED Copy with citationCopy as parenthetical citation