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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 11 December 2025 has been entered.
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 21-23 are rejected under 35 U.S.C. 103 as being unpatentable over Yang (US 3,851,004) in view of Chang (US 5,516,954), D’ouville (US 2,338,711) and Van Broekhoven (US 2008/0183025).
Regarding claims 1 and 19, Yang teaches alkyation 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, ruthenium, alone or in combination with each other (column3 , lines 54-75).
Yang does not explicitly disclose (1) group vii metals (2) fractionation of the mixture from step a to recycle unreacted aromatics to step a (3) h2 regeneration of catalyst.
Regarding (1), Chang teaches a similar process for alkylation of aromatics with olefins (column 1, lines 14-45). Chang teaches suitable hydrogenation metals include platinum, palladium, and group vii metals including rhenium (column 4, lines 15-31).
Therefore, it would have been obvious to the person having ordinary skill in the art to have selected any appropriate catalytic metals, such as the Chang combination of platinum, palladium, and rhenium. It is not seen where such a mixture would result in any new or unexpected results.
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 (3), Van Broekhoven teaches a similar alkylation process, wherein 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].
Therefore, it would have been obvious to the person having ordinary skill in the art to have performed the regeneration of Van Broekhoven, for the benefit of obtaining the desired catalytic activity.
Regarding claim 3, the previous combination teaches the limitations of claim 1 above.
Yang teaches using zeolites, but not specifics.
Van Broekhoven teaches a similar alkylation, using solid acid can be zeolites including beta, MCM 22, USY, silica alumina, etc [0005].
Therefore, it would have been obvious to the person having ordinary skill in the art to have used an appropriate zeolite, such as one disclosed by Van Broekhoven, for the benefit of obtaining the desired products.
Regarding claims 4-6 and 21-23, 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 selected appropriate metal amounts, as disclosed by Yang, for the benefit of obtaining the desired alkylation behavior.
Regarding claim 15-17, Van Broekhoven teaches hydrogen regeneration temperatures of 150-600°C [0032], overlapping with the claimed range.
Claims 7 is rejected under 35 U.S.C. 103 as being unpatentable Yang (US 3,851,004) in view of Chang (US 5,516,954), D’ouville (US 2,338,711) and Van Broekhoven (US 2008/0183025) 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.
Claims 8-14 and 18 are rejected under 35 U.S.C. 103 as being unpatentable over Yang (US 3,851,004) in view of Chang (US 5,516,954), D’ouville (US 2,338,711) and Van Broekhoven (US 2008/0183025) as applied to claim 1 above, and further in view of Bogaard (WO 98/23560).
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 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.
Response to Arguments
Applicant's arguments filed 11 December 2025 have been fully considered and are addressed by the updated rejections as necessitated by amendments to the claims.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
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).
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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/MICHELLE STEIN/Primary Examiner, Art Unit 1771