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 and 19 are amended. Claims 2-7 and 13 are cancelled. Claims 20-22 are withdrawn due to an earlier restriction requirement.
The amendment to claim 19 overcomes the previous claimed objection.
Claims 1, 8-12, and 14-19 are pending for examination below.
Response to Arguments
Applicant's arguments filed 04 May 2026 have been fully considered but they are not persuasive.
Applicant argues on pages 8-10 of the Remarks that the process is integrated with bi-directional synergy, which is not appreciated by the numerous references cited in the Office Action in isolation, and that the integration enhances production of benzyl toluene with less waste and enhanced process efficiencies.
In response, the arguments to synergy and enhanced production are mere assertion, with no evidence provided in support. The specification provides no examples showing any synergistic results or enhanced efficiencies, and one of ordinary skill in the art would expect that using streams which are typically waste within a process as feed streams to other processes would provide a process which produces less waste. Thus, the argument is not persuasive.
Applicant argues on page 10 of the Remarks that the Examiner has used the claims as a roadmap, implying improper hindsight for the combinations.
In response, In response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971). As Applicant acknowledges, feeding an effluent from one process as a feed to another process is typically something one skilled in the art can do. Absent any evidence, the claimed process is merely using effluents or unused streams from certain processes as feeds to other processes in order to minimize waste. This remains obvious to one of ordinary skill in the art, and the claims remain rejected.
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 1, 9, 10, 14, and 16-18 are rejected under 35 U.S.C. 103 as being unpatentable over Schmerling (US 3,679,760) as evidenced by Cosford (Copper(II) Chloride) in view of Wulf et al. (US 2,954,412), Ham et al. (US 4,849,092), and Suggitt et al. (US 3,927,135).
With regard to claim 1, Schmerling teaches a process for preparing diarylalkanes (column 1, lines 2-4) comprising
(iii) providing toluene, benzyl chloride, and cupric chloride to an alkylation reactor, where the toluene is provided in excess relative to the benzyl chloride, and
(iv) operating the reactor to produce a stream comprising HCl (second HCl effluent stream) and a benzyl toluene product stream (column 3, Example II). Cosford evidences that cupric chloride is a Lewis acid (page 1, first column).
While Schmerling does not specifically teach that the alkylation is a Friedel-Crafts reaction or that the purpose of the excess toluene is to consume chloride species and limit formation of dibenzyltoluene and other higher order products, because Schmerling teaches the same process of alkylation with the same Lewis acid catalyst and the same excess toluene, one of ordinary skill in the art would reasonably expect that the reaction is a Friedel-Crafts alkylation and the result of the excess toluene is to consume chloride species and limit formation of dibenzyltoluene, as claimed, absent any evidence to the contrary.
Schmerling does not specifically teach the source of the benzyl chloride as claimed steps (i)-(ii). Thus, one of ordinary skill in the art would look to related art to find a known source of benzyl chloride for alkylation reactions.
Wulf teaches a process for reaction of benzyl chloride with benzene hydrocarbons including toluene (column 1, lines 16-17 and lines 57-58). Wulf further teaches that the process comprises:
(i) introducing toluene and chlorine gas to a reactor; and
(ii) operating the reactor to generate a benzyl chloride stream and a hydrogen chloride stream (first HCl effluent stream) (column 3, Example 3).
Wulf further teaches using the benzyl chloride stream in an alkylation reactor to alkylate toluene (column 3, Example 3). Thus, Wulf teaches that benzyl chloride produced by halogenation of toluene is a suitable feed to alkylation reactions comprising toluene.
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 Wulf to produce the benzyl chloride of Schmerling, because Schmerling teaches a process of alkylation of benzyl chloride but is silent as to the source, and Wulf teaches that a halogenation process provides suitable benzyl chloride for alkylation reactions (column 3, Example 3).
Schmerling and Wulf fail to teach the naphtha reforming process in claimed steps (v)-(ix).
Ham teaches a process for regenerating catalysts (Abstract) comprising the following steps:
(v) providing naphtha to a reforming unit comprising a reforming catalyst (column 1, lines 30-36).
(vi) reforming the naphtha to produce a reaction product (column 1, lines 50-52) and a catalyst to be regenerated (spent catalyst) (column 2, line 47).
(vii) providing the catalyst to a regenerator along with HCl gas (column 2, lines 66-68 and column 3, lines 48-49).
(viii) producing a regenerated catalyst from the regeneration (column 3, lines 8-10).
(ix) providing the regenerated catalyst back to the reactor (reforming unit) (column 4, lines 15-18).
Ham does not specifically teach a source for the HCl gas used in the regenerator. However, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the HCl streams produced by Schmerling and Wulf (first and second HCl effluent streams instant claims 1 and 2) as the HCl gas stream in the regeneration process of Ham, because one of ordinary skill in the art is capable of using HCl gas from any source in the process, which includes the HCl streams of Schmerling and Wulf, and the use of HCl streams which would otherwise be waste streams from the process is of environmental benefit for the chemical reaction processes.
Schmerling in view of Wulf and Ham fails to teach steps (x)-(xiii) of separating and using aromatics streams from the reformate effluent.
Suggitt teaches a process for preparing hydrocarbons (column 1, lines 5-7) comprising reforming naphtha to form a reformate, and
(x) separating the reformate product in a complex (claimed aromatics complex) comprising extractive distillation 13 and distillation 15 to obtain a benzene stream, toluene stream, and xylenes (understood to be mixed xylenes) stream (column 14, claim 10 and column 8, lines 32 and 40).
(xii) passing the benzene and mixed xylenes to a transalkylation reactor to obtain an effluent comprising toluene (claimed reverse transalkylation) (column 14, claim 10).
(xiii) recycling the transalkylation effluent to the aromatics separation unit (column 5, lines 56-59).
Suggitt further teaches that the separation of the reformate, transalkylation, and transalkylation effluent separation steps upgrade gasoline, thus removing undesired benzene from gasoline (column 1, lines 33-35 and 52-53).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to add the steps of separation and transalkylation of Suggitt to the process of Ham, because each of Ham and Suggitt teach reforming naphtha to produce an aromatic fraction which can be used for gasolines, Ham is silent regarding further use of the reformate, and Suggitt teaches that separating the benzene, toluene, and xylenes streams allows for using the benzene and C8 aromatics for further purposes such as upgrading gasoline (column 1, lines 33-35 and 52-53).
Schmerling in view of Wulf, Ham, and Suggitt does not specifically teach step (xi) of passing the toluene separated from the reformate to each of the halogenation and alkylation reactors as part of the toluene feed.
However, it would have been obvious to one of ordinary skill in the art at the time of the invention, having obtained the toluene in the process of Ham in view of Suggitt, to find a use for the toluene, and one of ordinary skill in the art would be motivated to use the toluene as the feed in the halogenation and alkylation reactors in order to save costs within the process by reducing the need for fresh feed for the halogenation and alkylation steps.
With regard to claims 9-10, Wulf teaches that the halogenation reaction proceeds both with heating (thermally) and with ultraviolet light (photochemically) (column 2, lines 6-9).
With regard to claim 14, Ham teaches that the regeneration is continuous (column 6, lines 64-65).
With regard to claim 16, Ham teaches the regeneration comprises a first step of combustion comprising heating to a temperature of 350-550°C in a nitrogen stream comprising 0.01 to 1% oxygen (column 3, lines 16-27). This overlaps the ranges of 500-600°C and 0.8 to 1.3 wt% oxygen of instant claim 16, rendering the ranges prima facie obvious.
With regard to claim 17, Ham teaches the catalyst for reforming comprises platinum on alumina (column 1, lines 65-66).
With regard to claim 18, Ham teaches the regeneration comprises a second step of contacting the combusted (decoked) catalyst with the HCl gas stream and oxygen at a temperature of 350-550°C (column 3, lines 44-46 and 67). This overlaps the range of 475-525°C of instant claim 18, rendering the range prima facie obvious. Ham does not specifically teach that the chlorination is for redispersing platinum and replenishing chlorine, however, it is well known in the art that the purpose of the chlorination step in regeneration of a reforming catalyst is to redisperse the platinum and replenish the chlorine.
Claim 8 is rejected under 35 U.S.C. 103 as being unpatentable over Schmerling (US 3,679,760) as evidenced by Cosford (Copper(II) Chloride) in view of Wulf et al. (US 2,954,412), Ham et al. (US 4,849,092), and Suggitt et al. (US 3,927,135) as applied to claim 1 above, and further in view of Weiss et al. (WO 2022/122495).
US 2024/0034621 is used as the English language equivalent of the WO document herein.
With regard to claim 8, Schmerling in view of Wulf, Ham, and Suggitt teaches the process above which produces benzyl toluene.
Schmerling in view of Wulf, Ham, and Suggitt does not specifically teach a further reaction of the benzyl toluene.
Weiss teaches a method for utilization of hydrogen (Abstract) comprising using perhydrobenzyltoluene as a hydrogen carrier medium (paragraph [0023]). Weiss further teaches that the hydrogen carrier medium is formed by hydrogenating the hydrogen carrier medium in a hydrogenation reactor upstream of the use of the hydrogen carrier medium (page 11, claim 4). When the hydrocarbon carrier is perhydrobenzyltoluene, it is understood that the carrier medium before hydrogenating is benzyl toluene, as claimed.
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 Weiss to hydrogenate the benzyl toluene of Schmerling in view of Wulf, Ham, and Suggitt, because Schmerling in view of Wulf, Ham, and Suggitt teaches producing benzyl toluene but does not specifically teach further reaction, and Weiss teaches that hydrogenating the benzyl toluene to form perhydrobenzyltoluene allows for the compound to be used as a hydrogen carrier medium, which simplifies the use of hydrogen as a resource (paragraph [0007]).
Weiss does not specifically teach the hydrogen is obtained from catalytic reforming. However, Schmerling in view of Wulf, Ham, and Suggitt teaches reforming naphtha, as claimed. It is understood that the aromatics formed by the reforming release hydrogen in the reaction. Thus, Ham implicitly teaches the presence of hydrogen, but does not specifically teach a further use of the hydrogen. Thus, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the hydrogen from the reforming in the process of hydrogenating the benzyl toluene, as claimed, because using hydrogen produced within the process would save cost by diminishing the need for fresh hydrogen.
Claim 11 is rejected under 35 U.S.C. 103 as being unpatentable over Schmerling (US 3,679,760) as evidenced by Cosford (Copper(II) Chloride) in view of Wulf et al. (US 2,954,412), Ham et al. (US 4,849,092), and Suggitt et al. (US 3,927,135) as applied to claim 1 above, and further in view of Wang et al. (CN 107473931, machine translation provided herein).
With regard to claim 11, Schmerling in view of Wulf, Ham, and Suggitt teaches the method above, where the halogenation comprises a chlorination unit (Wulf column 3, Example 3).
Schmerling in view of Wulf, Ham, and Suggitt fails to teach separation of toluene from the product and recycling toluene to the chlorination unit as feed.
Wang teaches a method of producing benzyl chloride (paragraph [0001]). Wang teaches the process comprises chlorination of toluene in a chlorination reactor, followed by passing the effluent to a separation tower to recover toluene, which is recycled to the chlorination reactor (paragraph [0012]). Wang teaches that the process comprising these steps produces benzyl chloride with a purity of greater than or equal to 99.5%.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the reaction setup comprising a chlorination reactor and separation tower of Wang in the process of Schmerling in view of Wulf, Ham, and Suggitt, because Wulf and Wang each teach halogenation of toluene with chlorine to produce benzyl chloride, and Wang teaches the benzyl chloride has a purity of greater than or equal to 99.5% when produced and separated in the manner of Wang including separating and recycling the toluene to the chlorination reactor.
Claim 12 is rejected under 35 U.S.C. 103 as being unpatentable over Schmerling (US 3,679,760) as evidenced by Cosford (Copper(II) Chloride) in view of Wulf et al. (US 2,954,412), Ham et al. (US 4,849,092), and Suggitt et al. (US 3,927,135) as applied to claim 1 above, and further in view of Schmerling (US 3,637,883).
Schmerling (US 3,679,760) is referred to as Schmerling I and Schmerling (US 3,637,883) is referred to as Schmerling II herein.
With regard to claim 12, Schmerling I in view of Wulf, Ham, and Suggitt teaches the method of alkylation above, where the catalyst comprises cupric chloride.
Schmerling I fails to teach the catalyst comprises one of the Lewis acids in claim 12.
Schmerling II teaches a process for alkylation of aromatic compounds with alkylating agents in the presence of a catalyst comprising a mixture of two metal halides (column 1, lines 20-25) which are preferably zinc chloride (ZnCl2 instant claim 12) and cupric chloride (column 3, lines 20 and 36-37). Schmerling II further teaches that this catalyst combination allows the alkylation reaction to take place at relatively low operating temperatures (column 1, line 13).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the combination of catalysts in Schmerling II in the process of Schmerling I, because Schmerling I and Schmerling II each teach alkylation of aromatic compounds with alkylating agents in the presence of cupric chloride, and Schmerling II teaches that including ZnCl2 allows the alkylation to be effected at relatively low operating temperatures (column 1, line 13).
Claim 15 is rejected under 35 U.S.C. 103 as being unpatentable over Schmerling (US 3,679,760) as evidenced by Cosford (Copper(II) Chloride) in view of Wulf et al. (US 2,954,412), Ham et al. (US 4,849,092), and Suggitt et al. (US 3,927,135) as applied to claim 15 above, and further in view of Frey et al. (US 2008/0161622).
With regard to claim 15, Schmerling in view of Wulf, Ham, and Suggitt teaches the method above, including reforming.
Schmerling in view of Wulf, Ham, and Suggitt fails to teach the presence of two reactors and regenerators and alternating the operation of the reactors such that the first reactor is operated while the second reforming unit catalyst is being regenerated, and vice versa.
Frey teaches a process for production of aromatics (paragraph [0002]). Frey further teaches that a known arrangement for naphtha reforming includes swing-reactor operation in which an individual reactor is isolated, regenerated, and reactivated while other reactor(s) remain on stream (paragraph [0026]). Thus, Frey teaches that it is known to operate naphtha reforming reactors in the claimed manner where a first reactor is operated while the second catalyst is being regenerated, and vice versa.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use multiple reactors arranged in the manner taught by Frey, such that the first reactor is operated while the second is regenerating and vice versa, as claimed, because Schmerling in view of Wulf, Ham, and Suggitt is silent regarding the specific arrangement for the naphtha reforming and Frey teaches that the claimed arrangement is known and suitable for naphtha reforming.
Claim 19 is rejected under 35 U.S.C. 103 as being unpatentable over Schmerling (US 3,679,760) as evidenced by Cosford (Copper(II) Chloride) in view of Wulf et al. (US 2,954,412), Ham et al. (US 4,849,092), and Suggitt et al. (US 3,927,135) as applied to claim 18 above, and further in view of Hallman (US 3,684,698).
With regard to claim 19, Schmerling in view of Wulf, Ham, and Suggitt teaches the method above, where the regeneration process comprises contacting the catalyst with chlorine and oxygen to redisperse platinum and replenish chlorine.
Schmerling in view of Wulf, Ham, and Suggitt fails to teach a drying step before reusing the regenerated catalyst in the reforming unit.
Hallman teaches that regeneration of platinum and halogen containing reforming catalysts produces water by oxidation, which then must be removed by a drying process before placing the catalyst back onstream to avoid rapid deactivation of the catalyst (column 2, lines 24-33).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to include a drying step as taught by Hallman for the catalyst of Ham, because each of Ham and Hallman teach reforming over a platinum and halogen containing catalyst where the regeneration includes oxidation, and Hallman teaches that the oxidation produces water which must be removed by drying before the catalyst is returned to the reactor (column 2, lines 24-33).
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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