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 .
Response to Amendment
Examiner acknowledges Applicant’s response filed 23 March 2026 containing remarks and amendments to the claims.
The previous rejections have been updated as necessitated by amendments to the claims. The updated rejections follow.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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, 3-6, 15-17, 19 and 24-26 are rejected under 35 U.S.C. 103 as being unpatentable over Van Broekhoven (US 2008/0183025) in view of Bogaard (WO 98/23560), Yang (US 3,851,004) and D’ouville (US 2,338,711).
Regarding claims 1 and 19, van Broekhoven teaches alkylation of aromatics with olefins in the presence of zeolite or silica alumina catalyst having group VIII hydrogenation metals such as platinum or palladium [0001-0005]. Van Broekhoven teaches the metal can be incorporated into the catalyst using ion exchange, or salts, including nitrates (non halide) [0039]. Van Broekhoven teaches the catalyst is regenerated by contact with hydrogen at a temperature of 150-600°C [0032], which includes temperatures higher than the alkylation temperatures of -40-250°C [0031], in order to restore catalytic activity so further alkylation may be performed [0031-0033]. Van Broekhoven teaches that the hydrogen regenerations may be performed as described by Bogaard (WO 98/23560) [0032].
Bogaard teaches that the regeneration temperatures and pressures may be independently the same as or higher than the alkylation reaction step (see page 10). Bogaard teaches that the regeneration may be carried out for a duration, which can be adjusted depending on factors including the duration of the reaction step, and the concentration of the hydrogen (page 10). In this regard, Examiner notes that it would have been obvious to the person having ordinary skill in the art to have selected appropriate temperatures, pressures, duration, and cycles, in order to obtain the desired regeneration. Bogaard further teaches that the catalyst is regenerated for multiple cycles, and that a product of nearly constant composition and high yield is obtained (page 4, see also, examples). Bogaard additionally notes that regeneration processes are known to restore catalyst to original level (page 2), which Examiner considers to read on “within 10% of its pre-regeneration level”. In this regard, Examiner considers the Bogaard regeneration to restore the catalyst to original level.
Van Broekhoven does not explicitly disclose (1) presence of rhodium (2) fractionation of the mixture from step a to recycle unreacted aromatics to step a.
Regarding (1), Yang teaches alkylation of olefin with aromatic in the presence of hydrogen and catalysts (column 1, lines 1-35). Yang teaches the catalyst comprises crystalline zeolite support and hydrogenation metals (column 3, lines 1-75). Yang teaches that the metals employed can include platinum, palladium, rhodium, alone or in combination with each other (column3 , lines 54-75). Yang teaches that the metal can be incorporated in a salt solution.
Therefore, it would have been obvious to the person having ordinary skill in the art to have used rhodium in combination with the platinum/palladium of van Broekhoven, since it is known for the same purpose as hydrogenation metal in alkylation catalyst.
Regarding (2), D’ouville teaches similar process for alkylation of aromatics with olefins (see figure). D’ouville teaches separation of the alkylation product into light vent gas, light and heavy aromatics (unreacted/unalkylated), and alkylated aromatic products (see figure). D’ouville recycles the non-alkylated aromatics to the alkylation zone, in order to recover more of the desired alkylated products (see figure).
Therefore, it would have been obvious to the person having ordinary skill in the art to have incorporated the D’ouville fractionation and recycle steps, for the benefit of recovering more of the desired alkylated products.
Regarding claim 3, Van Broekhoven teaches a similar alkylation, using solid acid can be zeolites including beta, MCM 22, USY, silica alumina, etc [0005].
Regarding claims 4-6 and 24-26, Van Broekhoven teaches 0.01-2% metals [0005]. Additionally, Yang teaches alkylation of olefins with aromatics using hydrogenation catalysts (column 1, lines 1-35). Yang teaches hydrogenation metals including platinum, palladium, and rhodium in combination (column 3, lines 54-75). Yang teaches using 0.05-2% of the hydrogenation metals (column 3, lines 54-75), which encompasses the claimed values.
Therefore, it would have been obvious to the person having ordinary skill in the art to have appropriately selected the amounts of each component as disclosed by van Broakehoven/Yang in order to obtain the desired alkylation activity.
Further, Bogaard teaches selecting appropriate temperatures, pressures, and residence time for regeneration, in order to obtain the desired regeneration (page 10, line 23-page 11, line 5).
Regarding claims 8-10, Van Broekhoven teaches alkylation temperatures of -40-250°C and 1-100 bar [0031], overlapping with the claimed ranges. Van Broekhoven further notes that WO 98/23560 (Bogaard) discloses suitable alkylation conditions [0031].
Bogaard teaches space velocity of 0.1-500 hr-1 (page 8, lines 14-30).
Therefore, it would have been obvious to the person having ordinary skill in the art to have used the Bogaard space velocity, since Van Broekhoven teaches using Bogaard conditions.
Regarding claim 11, Van Broekhoven teaches using Bogaard conditions [0031-32]. Bogaard teaches the hydrogen regeneration can be performed at approximately the same pressures as used in the alkylation step, including 1-100 bars (page 10, lines 1-22).
Regarding claims 12-14, Bogaard teaches selecting appropriate residence time for regeneration, in order to obtain the desired regeneration (page 10, line 23-page 11, line 5).
Therefore, it would have been obvious to the person having ordinary skill in the art to have appropriately selected residence time of the regeneration step, in order to obtain the desired catalyst regeneration.
Regarding claim 15-17, Van Broekhoven teaches hydrogen regeneration temperatures of 150-600°C [0032], overlapping with the claimed range.
Regarding claim 18, Bogaard teaches using as high of a saturation of hydrogen as possible, in order to reduce regeneration time (page 9, lines 13-30).
Therefore, it would have been obvious to the person having ordinary skill in the art to have selected an appropriate amount of hydrogen, in order to reduce regeneration time. It is not seen where such a selection would result in any new or unexpected results.
Claims 7 is rejected under 35 U.S.C. 103 as being unpatentable Van Broekhoven (US 2008/0183025) in view of Bogaard (WO 98/23560), Yang (US 3,851,004) and D’ouville (US 2,338,711) as applied to claim 1 above, and further in view of Dakka (WO 2008/101616).
Regarding claim 7, the previous combination teaches the limitations of claim 1, as discussed above.
The previous combination does not explicitly disclose hydrogenation of the alkylaromatics using a hydrogenation catalyst.
However, Dakka teaches a similar process for aromatic alkylation with olefins [0013]. Dakka teaches treating the effluent with hydrogen under hydrogenation conditions with rhodium catalyst, in order to obtain hydrogenated products [0013]. It is expected that the same products would result, since Dakka teaches the same steps as claimed.
Therefore, it would have been obvious to the person having ordinary skill in the art to have performed the Dakka hydrogenation, in order to obtain further products from the alkylaromatics. It is not seen where such a modification would result in any new or unexpected results.
Response to Arguments
Applicant's arguments filed 23 March 2026 have been fully considered but they are not persuasive.
Examiner considers Applicant’s argument to be:
The prior art does not disclose the combination of platinum, palladium, and rhodium from halide-free precursor on silica alumina/or zeolite, which results in the ability to regenerate fully with hydrogen for multiple cycles and restoration of alkylation activity within 10% of its pre regeneration level. Applicant’s specification teaches the ability to regenerate the catalyst fully with hydrogen is an unexpected benefit obtained by the combination of metals and lack of halide.
In response, Examiner notes that van Broekhoven teaches incorporation of metals by nitrate salt (non halide) [0039] and regeneration with hydrogen to original activity levels [0032], see also Bogaard (page 2 and 10). In this regard, it is not seen where the regeneration level is an “unexpected” benefit. Examiner notes that the comparison must be made to the closest prior art of record. Van Broekhoven/Bogaard teaches full regeneration with hydrogen. Thus, it is not seen where such a result is unexpected.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Chang (US 5,516,954) – previously relied upon for teachings of rhenium (group 7)
Zhang (US 5,489,732) - teaches alkylation of aromatics with olefins and hydrogen regeneration (abstract).
Umansky (US 2006/0194998) – teaches alkylation of aromatics with olefins [0029].
Yang (US 3,851,00) – teaches hydrocarbon alkylation with regeneration (column 1, lines 10-20).
Fenton (US 3,342,887) – teaches alkylation of aromatics with rhenium catalyst (column 1, lines 1-40).
Clark (US 2008/0139859) – teaches alkylaromatic production process (abstract).
Tabak (US 4,594,143) -teaches reacting olefins with aromatics to produce alkyl aromatics (abstract).
Chen (US 4,871,444) -teaches alkylation of fcc cycle oils (column 1, lines 1-15).
Harandi (US 4,992,607) -teaches alkylation of aromatics and catalyst regeneration (see abstract and figure).
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 MICHELLE STEIN whose telephone number is (571)270-1680. The examiner can normally be reached Monday-Friday 8:30 AM-5:00 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Prem C Singh can be reached at 571-272-6381. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/MICHELLE STEIN/Primary Examiner, Art Unit 1771
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