DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 02/12/2026 has been entered.
Response to Amendment
The examiner acknowledges Applicant’s response filed on 02/12/2026 containing remarks and claims amendments.
Response to Arguments
Applicant’s arguments (see Remarks) with respect to the rejection of claims 1-20 under 35 USC 103 over Wang (CN 106518602 A), in view of White (US 4,645,585) and Kiss (US 2015/0099910 A1), have been fully considered and are persuasive. Claim 1 has been amended to remove “iron” from the list for the “second active metal,” and the cited references do not teach the remaining metals of the second active metal (i.e., vanadium, chromium, manganese, or copper).
Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground of rejection is made in view of Wang et al. (CN 106518601 A, cited in IDS dated 08/04/2023) in view of White (US 4,645,585, applied in the previous rejection).
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1- 20 are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN 106518601 A, cited in IDS dated 08/04/2023; see attached translation), in view of White (US 4,645,585).
Regarding claim 1, Wang discloses a process comprising:
introducing hydrogen gas into a benzene feed stream ([0009]; [0056]);
directing the benzene feed stream into a catalytic reaction zone comprising a catalyst ([0009]; [0056]); and
heating the benzene feed stream in the presence of the catalyst to form a product stream ([0056], “the reaction temperature is 170°C”); wherein the product stream comprises cyclohexylbenzene, cyclohexane, methylcyclopentylbenzene, and dicyclohexylbenzene (Table 1), which can correspond to a commodity fraction (e.g., cyclohexylbenzene) and bottoms containing diesel range aromatics (e.g., dicyclohexylbenzene, which has a boiling point of 365.8°C or 690.44°F).
Wang discloses that the catalyst comprises a noble metal active component comprising at least one of palladium, ruthenium, platinum, rhodium, or iridium, and a transition metal auxiliary active component comprising vanadium, chromium, manganese, and/or copper ([0015]-[0016]). The noble metal active component and the transition metal auxiliary active component correspond to the first active metal and the second active metal of claim 1, respectively.
Wang does not teach that the benzene feed stream is a heart-cut reformate stream comprising benzene from a catalytic reforming process.
However, White teaches a method comprising obtaining a reformate comprising BTX and subjecting all or part of the BTX to a hydroalkylation step to produce non-fused double ring compounds (col. 14, lines 26-56).
Therefore, before the effective filing date of the instant invention, it would have been obvious to one of ordinary skill in the art to modify Wang by employing a heart-cut reformate stream comprising benzene as a benzene feed stream to the hydroalkylation process, as taught by White, because (i) Wang is silent on suitable sources of the benzene feed stream, (ii) White suggests that a heart-cut reformate comprising benzene can be used as a feedstock to the hydroalkylation, and (iii) this merely involves application of a known source of feedstock to a known process to yield predictable results.
Regarding claims 2 and 5, Wang provides examples in which the benzene conversions are 41.64%, 46.53%, and 40.53% (Table 1 ), which read on the benzene conversion range of "at least 40%." With regard to the claimed benzene concentration of “about 5% to about 75% by weight benzene” in the feed stream, White teaches employing a heart-cut reformate stream comprising BTX, exemplified by a reformate including 5.76 wt% benzene (Table 4).
Regarding claim 3, Wang discloses that the reaction conditions include a temperature of 100-300 °C ([0019]). The claimed temperature range of “about 100°C to about 250°C” falls within the temperature range taught by Wang and is considered prima facie obvious. In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. MPEP 2144.05. I.
Regarding claim 4, Wang discloses that the reaction conditions include a pressure of 0.5-5.0 MPa, i.e., about 72.5-725.2 psig ([0019]). The claimed pressure range of “about 50 psig to about 500 psig” overlaps the pressure range taught by Wang and is considered prima facie obvious.
Regarding claim 6, Wang discloses that reaction products include cyclohexane whose formula is C6H12 (Table 1). The reaction products further include cyclohexylbenzene, methylcyclopentyl benzene, and dicyclohexylbenzene (Table 1) Therefore, the reaction products are considered to include a naphtha fraction (e.g., cyclohexane), a commodity fraction (e.g., cyclohexylbenzene), and a diesel fraction (e.g., methylcyclopentyl benzene and dicyclohexylbenzene).
Regarding claims 7-9, Wang, in view of White(“Wang/White”), does not explicitly teach that (i) the naphtha fraction comprises alkyl substituted or unsubstituted C6-Cs alkyl hydrocarbon and isomers thereof having a formula CnH2n wherein the index n is about 6 to about 8 (claim 7); (ii) the diesel fraction comprises dicyclohexylbenzene, dicyclohexylcyclohexane, and isomers thereof, and (iii) the commodity fraction comprises cyclohexylbenzene, bicyclohexyl, and isomers thereof.
However, the processes of Wang/White and the instant application are identical or substantially identical, i.e., they are both drawn to a process of hydroalkylating benzene in the presence of a catalyst comprising identical or essentially identical amounts of the same components (i.e., a noble active metal, an auxiliary active metal, organosilicon microporous zeolite, and a binder), the process operating under the same or overlapping reaction temperature and pressure conditions (Wang: [0009]-[0021], [0056]; see also Spec.: [0028], [0035], [0037], [0056]-[0061], [0069]-[0070]). Therefore, one of ordinary skill in the art would reasonably expect the process of Wang to have the same or substantially the same results as the claimed invention, in the absence of any evidence to the contrary. MPEP 2112.01 I. Specifically, the naphtha fraction, the diesel fraction, and the commodity fraction in the hydroalkylation effluent of Wang are expected to comprise the components recited in claims 7-9.
Regarding claim 10, Wang teaches that the product stream comprises cyclohexylbenzene, methylcyclopentylbenzene, and dicyclohexylbenzene (Table 1), which can correspond to a diesel fraction containing a commodity fraction (cyclohexylbenzene) and a pre-diesel fraction (methylcyclopentylbenzene and dicyclohexylbenzene).
Regarding claim 11, Wang/White teaches the method of claim 1, as discussed above.
White further teaches subjecting a hydroalkylation effluent to hydrogenation to increase the amount of bicyclohexyl (col. 14, lines 26-56; col. col. 15, lines 1-5). White teaches that the resulting product has improved diesel properties in cetane number and density due to increased saturation, e.g., to bicyclohexyl, and can be used as a blend material for diesel fuels (col. 9, lines 29-34; see also Table 2).
Therefore, before the effective filing date of the instant invention, it would have been also obvious to further modify Wang/White by subjecting a hydroalkylation effluent to hydrogenation to produce a material suitable for diesel blend, as taught by White, because (i) Wang/White teaches a process for hydroalkylation of benzene, (ii) White teaches hydrogenating a effluent from benzene hydroalkylation to improve diesel properties, and (iii) this involves application of a known technique to improve a known process to yield predictable results.
Regarding claims 12 and 13, Wang teaches a catalyst comprising:
(a) 0.05-5 wt% of a noble metal active component (“first active metal”), such as ruthenium, palladium, and/or platinum ([0009]-[0010], [0014]);
(b) 40-85 wt% of organosilicon microporous zeolite (Wang, [0012]); and
(c) 10-50 wt% of a binder, such as aluminum oxide, titanium oxide, zinc oxide, and/or zirconium oxide (Wang, [0013], [0020]).
The concentrations of the first active metal, the organosilicon microporous zeolite, and the binder taught by Wang overlap and render obvious the following claimed ranges: “about 0.1 wt% to about 10 wt% of the first active metal,” “about 40 wt% to about 90 wt% of an organosilicon microporous zeolite” and “about 10 wt% to about 60 wt% of a binder,” respectively.
Regarding claims 14-16, Wang teaches a catalyst comprising:
(a) 0.05-5 wt% of a noble metal active component (“first active metal”), such as ruthenium, palladium, and/or platinum ([0009]-[0010], [0014]);
(b) 40-85 wt% of organosilicon microporous zeolite (Wang, [0012]); and
(c) 10-50 wt% of a binder, such as aluminum oxide, titanium oxide, zinc oxide, and/or zirconium oxide (Wang, [0013], [0020]).
The concentrations of the first active metal, the organosilicon microporous zeolite, and the binder taught by Wang overlap and render obvious the following claimed ranges: “about 0.1 wt% to about 10 wt% of the first active metal,” “about 40 wt% to about 90 wt% of an organosilicon microporous zeolite” and “about 10 wt% to about 60 wt% of a binder,” respectively.
Wang does not explicitly teach that the catalyst additionally comprises “about 1 wt% to about 20 wt% of a total of a rare earth metal oxide and/or zirconium oxide.” However, Wang discloses that the binder can be a mixture of alumina, titanium dioxide, zinc oxide, and zirconium oxide ([0020]). Therefore, the binder of Wang, which is in an amount of 10-50 wt% and which may include zirconium oxide in mixture with other binder materials, encompasses and renders obvious the claimed limitation of “about 1 wt% to about 20 wt%” of zirconium oxide.
Wang does not disclose that the catalyst comprises is cerium oxide and/or lanthanum oxide as a rare earth metal oxide component, as recited in claim 16. However, claim 16 merely further limits one of the alternative limitations recited in claim 15: “a rare earth metal oxide and/or zirconium oxide.” Since Wang teaches the zirconium oxide alternative, the entire genus of claim 15 is rendered unpatentable. Where a claim recites a Markush group, the entire claim is unpatentable if any one of the alternatives is taught or suggested by the prior art. Therefore, claim 16, which only narrows the rare earth metal oxide element of the alternative limitations, is not considered inventive. If Applicant intends to distinguish the recitation of claim 16 over Wang, it is suggested that claim 16 be amended such that catalyst does require a rare earth oxide.
Regarding claims 17-19, Wang teaches a catalyst comprising:
(a) 0.05-5 wt% of a noble metal active component (“first active metal”), such as ruthenium and/or palladium ([0009]-[0010], [0014]);
(b) 0.05-10 wt% of an auxiliary metal active component (“second active metal”), such as copper ([0011], [0015]);
(b) 40-85 wt% of organosilicon microporous zeolite (Wang, [0012]); and
(c) 10-50 wt% of a binder (Wang, [0013], [0020]).
The concentrations of the first active metal, the second active metal, the organosilicon microporous zeolite, and the binder taught by Wang correspond to or render obvious the following claimed ranges: “about 0.5 wt% to about 10 wt% of the first active metal,” “about 0.05 wt% to about 10 wt% of the second active metal,” “about 40 wt% to about 85 wt% of an organosilicon microporous zeolite” and “about 10 wt% to about 60 wt% of a binder,” respectively.
Regarding claim 20, Wang discloses that the organosilicon microporous zeolite has a formula of (1/n)Al2O3:SiO2:(m/n)R, where n=5-250, and R is at least one of an alkyl group or a phenyl group with 1-8 carbon atom ([0016]).
Citation of Pertinent Prior Art
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Wang et al. (CN 106518602 A, applied in the prior Office Action) teaches the use of rare earth oxides, such as cerium oxide or lanthanum oxide, as auxiliary active catalytic components for the same purpose as the auxiliary active components of CN 106518601 (applied in the above rejection): to be used as electronic additive to inhibit the adsorption of cyclohexene on the first metal active components ([0016], [0030]).
Conclusion
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/JASON Y CHONG/Examiner, Art Unit 1772