DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claim Status
Claims 1-19 are cancelled. Claims 20-24 are new.
The amendments to the claims and specification overcome the previous specification objection and 112(b) and (d) rejections
Claims 20-24 are pending for examination below.
Response to Arguments
Applicant’s arguments and amendments filed 22 April 2026 with respect to the rejection(s) of claim(s) 1-12 under USC 103 have been fully considered and are persuasive. Wang in view of Radadia and Korelitz does not teach the claimed catalyst composition having Pt and at least two of Cr, Zn, and Mg. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of newly discovered prior art in view of the amendments.
Claim Objections
Claims 20-24 are objected to because of the following informalities:
With regard to claim 20, in step d), the claim recites “in the presence”. This should be “in presence” for antecedent basis purposes.
With regard to claims 21-22, the claim recites that the catalyst is “further functionalized” with Cr and Mg or Cr and Zn, respectively. However, claim 1 already recites that the catalyst is functionalized with “at least two of Cr, Zn, and Mg”. Thus, the recitation of “further” is unnecessary and can be deleted.
Also with regard to claim 21, the claim recites “with a Cr”. The word “a” should be deleted as unnecessary.
With regard to claim 23, the claim recites “a 1/3 vol/vol mixture”. The use of “1/3” could be confusing as / is often used to mean and/or or division, neither of which is intended in this case. The Examiner suggests the use of “1:3” as more typical in the art and clearer.
With regard to claim 24, the claim recites “further produces C6, and C7 aromatics products along with the alkylated aromatic products…” The comma after “C6” is unnecessary and should be deleted.
Appropriate correction is required.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claims 20-22 and 24 are rejected under 35 U.S.C. 103 as being unpatentable over Ou (US 7,902,414, cited on IDS of 03/22/2024) in view of Wang et al. (CN 110028375, cited on IDS of 03/22/2024, machine translation provided herein) and Radadia (Microfluidics for Biochemical and Chemical Reactions).
With regard to claims 20 and 22, Ou teaches a process for selective production of paraxylene from toluene in the presence of carbon monoxide and hydrogen (Abstract) comprising the following steps:
a) providing an HZSM-5 catalyst comprising HZSM-5, Zn, and Cu (claimed HZSM-5 catalyst functionalized with Cr and Zn instant claims 20 and 22) (column 12, claim 12) to a fixed bed reactor (column 6, line 24).
b) reducing the catalyst under a flow of H2 for 2-48 hours at a temperature of 100-700°C (column 6, lines 18-20), which overlaps the ranges of 450-500°C and 5-6 hours of instant claim 20.
c) introducing CO2, H2, and toluene in the reactor and forming methanol as the methylating agent in situ (claimed reducing the CO2 and H2 in the presence of the reduced catalyst to produce an active alkylating species) (column 6, lines 24-30).
d) reacting the toluene with the methylating agent to produce products including xylene (column 6, lines 47-53).
Ou fails to teach i) that the HZSM-5 catalyst also comprises Pt; ii) producing the toluene and H2 in situ by reacting methylcyclohexane and CO2/N2 at a temperature of 300-400°C; iii) wherein at least 93 wt% of the C8+ aromatics comprise C8-C10 aromatics and wherein at least 45 wt% of the C8+ aromatics comprise xylenes; or iv) that the fixed bed reactor is a fixed bed micro-reactor.
With regard to the reaction and catalyst i) and ii), Ou is silent regarding the source of the toluene, H2, and CO2 reactants. Therefore, one of ordinary skill in the art would be motivated to find a source for the toluene, H2, and CO2.
Wang teaches a method for conversion of methylcyclohexane to toluene. Wang teaches that the process comprises feeding methylcyclohexane and CO2 into a reactor at a temperature of 200-500°C and a pressure of 0.1-2 MPa (1 to 20 bar) over a catalyst comprising ZSM-5 and Pt to generate toluene (Abstract). The temperature and pressure of Wang overlap the claimed temperature of 300-400°C and pressure of 20-30 bar, rendering the ranges prima facie obvious. Wang further teaches that the process additionally produces hydrogen (paragraph [0021]), is performed in a fixed bed reactor with a reduced catalyst (paragraph [0030]), and additionally includes N2 in the feed (paragraph [0030]). Wang also teaches that the process is stable and includes a catalyst having good stability (paragraph [0022]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the process of Wang to form the reactants of Ou, because Ou teaches a process for selective para-xylene production over toluene, hydrogen, and CO2, but fails to teach the source of the reactants, and Wang teaches that dehydrogenation of methylcyclohexane in the presence of CO2 produces toluene and hydrogen and that the process is stable.
Ou in view of Wang does not explicitly teach that the dehydrogenation of methylcyclohexane and toluene alkylation steps can take place in the same reactor comprising both catalysts. However, the reactions each take place in a fixed bed reactor at the similar temperatures of 200-500°C (Wang paragraph [0014]) and 200-600°C (Ou column 6, line 65) and overlapping pressures of 0.1 to 2 MPa (1 to 20 bar) (Wang paragraph [0014]) and 1 to 300 atm (1 to 202 bar) (Ou column 6, line 66) and with similar catalysts comprising ZSM-5 and at least one metal (Wang Abstract and Ou column 12, claim 12) and with similar CO2 feed (Wang Abstract, Ou column 6, lines 24-30). Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to combine the steps of dehydrogenation and alkylation into a single reactor, as claimed, because changes in the sequence of process steps is prima facie obvious absent new or unexpected results (see MPEP 2144.04(IV)C) and the steps of Ou and Wang are designed with similar catalysts and similar temperature and pressures and a similar CO2 cofeed and thus would be expected to function if placed in the same reactor, as claimed, absent any evidence to the contrary.
With regard to the effluent composition iii), Ou in view of Wang teaches the process above which produces a product selective to para-xylenes. Ou exemplifies that the process produces a hydrocarbon product comprising a range of 60.3 to 73.6 wt% xylenes. This is within the range of at least 45 wt% of the alkylated C8+ product is xylenes of instant claim 20. Ou in view of Wang does not specifically teach the amount of C8-C10 aromatics in the product. However, because Ou in view of Wang teaches the similar process with similar conditions, feeds, and catalyst and produces a similar xylenes containing product, one of ordinary skill in the art would reasonably expect that the C8+ product comprises at least 93 wt% C8-C10 alkylated aromatics, as claimed, absent any evidence to the contrary.
With regard to the micro-reactor iv), each of Ou and Wang teaches a fixed bed reactor, but fails to specify the reactor is a microreactor.
Radadia teaches that microreactors for chemical reactions are preferred for improved safety and greater reaction control in chemical reactions (page 3).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use a fixed bed microreactor, as claimed, in the process of Ou in view of Wang, because each of Ou and Wang teaches a fixed bed reactor and Radadia teaches that microreactors are preferred for reactions because of improved safety and greater reaction control (page 3).
With regard to claim 21, Ou teaches that the catalyst comprising Zn and Cr further comprises Mg (column 8, line 35).
With regard to claim 24, Ou in view of Wang does not specifically teach that the process produces benzene and toluene along with the xylenes. However, as the process of Ou in view of Wang comprises the same reactants at similar conditions and over similar catalysts, one of ordinary skill in the art would reasonably expect that the process of Ou in view of Wang also produces benzene and toluene, as claimed, absent any evidence to the contrary.
Claim 23 is rejected under 35 U.S.C. 103 as being unpatentable over Ou (US 7,902,414) in view of Wang et al. (CN 110028375) and Radadia (Microfluidics for Biochemical and Chemical Reactions) as applied to claim 1 above, and further in view of Korelitz et al. (US 3,211,799).
With regard to claim 23, Ou in view of Wang teaches the presence of nitrogen in the feed.
Ou in view of Wang fails to teach the volume ratio of CO2 and nitrogen.
Korelitz teaches a process for alkylation of aromatic hydrocarbons (column 1, lines 10-11). Korelitz teaches that diluent gases such as nitrogen can be used in the alkylation process in a ratio of diluent:alkylating agent of 2-10:1 (column 5, lines 10-13). This range of 2-10:1 N2/CO2 is equivalent to a range of 1:2-10 CO2/N2, which encompasses the ratio of CO2 to N2 of 1:3 of instant claim 23, rendering the ratio prima facie obvious.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to add the diluent to the process of Wang in the claimed amount, because each of Wang and Korelitz teach a process comprising alkylation of an aromatic hydrocarbon, one of ordinary skill in the art understands the purpose of a diluent in a process, and Korelitz teaches it is known to use a diluent in a similar process comprising alkylation of an aromatic hydrocarbon in an amount which encompasses the claimed amount.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALYSSA L CEPLUCH whose telephone number is (571)270-5752. The examiner can normally be reached M-F, 8:30 am-5 pm, EST.
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/Alyssa L Cepluch/Examiner, Art Unit 1772
/Renee Robinson/Primary Examiner, Art Unit 1772
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