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
Claim 1 is amended. Claims 24-33 are new. Claims 2, 3, 7, 9-12, 14, 17, 18, and 20-22 are cancelled.
Claims 1, 4-6, 8, 13, 15, 16, 19, and 23-33 are pending for examination below.
Response to Arguments
Applicant’s arguments and amendments, see Remarks, filed 22 December 2025, with respect to the rejection(s) of claim(s) 1, 4-6, 8, 13, 15, 16, 19, and 23 under USC 103 over Calaresu have been fully considered and are persuasive. Calaresu does not teach a fixed bed liquid phase reactor, as claim 1 is interpreted as requiring, and if fact teaches away from this reactor by requiring a trickle flow reactor comprising both liquid and gas flows (paragraphs [0033]-[0034]). Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of new 112(b) issues and newly discovered prior art in view of the amendments.
Applicant's arguments filed 22 December 2025 have been fully considered but they are not persuasive.
Applicant argues on pages 8-9 of the Remarks that the phrase “fixed bed fluid-type reaction apparatus” means that the alkylation reaction takes place in liquid phase, unlike Calaresu, which employs a trickle bed reactor having both gas and liquid phase reactants (Calaresu paragraphs [0033]-[0034]).
In response, the Examiner respectfully cannot agree that the phrase “fluid-type” necessarily means all reactants are in liquid phase. The phrase “fluid-type apparatus” is not used anywhere in the instant specification except Example 1, paragraph [0040]. In this Example, the reactants include benzene and cyclohexene, the temperature is 250°C, and the pressure is 0.9 MPaG. There is no mention of the reactants being liquid or gas phase, and the Examiner was unable to find a phase diagram for cyclohexene to confirm whether the compound is in the liquid or gas phase at that temperature and pressure. As such, there is no evidence within the recitations of the instant specification that the phrase “fluid-type” is meant to mean “liquid phase” as opposed to merely “comprising fluids”. The word “fluid” is often used within the art to refer to both liquids and gases. Further, the phrase “fluid-type” reactor is not used in the art to mean “liquid phase”, but is used in the art to refer to a fluidized bed reactor (see US 2016/0158734 paragraph [0060] and US 2610976 column 2, lines 58-59). Thus, without evidence that the reactants are both in liquid phase for the reaction, the Examiner is unable to agree to this interpretation, and instead will interpret the term more generally, as requiring fluid reactants. As such, Calaresu is maintained because the reactants in the gas phases are still considered to be fluid-type reactants as explained above.
Applicant argues on pages 9-10 of the Remarks that the instant specification provides evidence of unexpected results with the liquid phase reaction.
In response, the Examiner respectfully disagrees. As explained above, there is no evidence that the reaction in the Examples takes place in liquid phase for both reactants. Further, as explained in the Non-Final Office Action of 25 September 2025, while Example 4 of the instant specification does show a decreased selectivity to cyclohexylbenzene at a benzene amount of 50 wt%, there is no data shown for amounts between the amounts of 50 wt% and 75 wt% benzene. The range of benzene of Calaresu starts at 59 wt%, and the Examples do not provide any evidence that 59 wt% is the same as 50% or unexpectedly worse than 75 wt%. Further, Perego (Chapter 2, Advances in Aromatics Processing Using Zeolite Catalysts) teaches that it is obvious that to increase selectivity to the monoalkylate, the alkylation reaction can be operated with a large excess of the aromatic, in other words a high aromatic/olefin ratio (page 122, first paragraph). Thus, even if there was data in the Tables showing that 59 wt% benzene in the feed provides worse selectivity than 75 wt% benzene, the worse selectivity is not unexpected to those of ordinary skill in the art as taught by Perego, and the claimed range remains rendered obvious by Calaresu.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1, 4-6, 8, 13, 15, 16, 19, and 23-33 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
With regard to claim 1, the claim recites “a fixed bed fluid-type reaction apparatus”. The phrase “fluid-type” is unclear and not defined in the specification. Generally in the art “fixed” and “fluid-type” are different types of catalyst beds, “fluid-type” meaning fluidized (see US 2016/0158734 paragraph [0060] and US 2610976 column 2, lines 58-59). However, in the instant application, it is used in conjunction with “fixed bed” and thus cannot mean “fluidized bed”. Thus, it is unclear what is meant by this phrasing, and the claim is indefinite.
For purposes of examination, the instant specification uses the language of “fixed bed fluid-type apparatus” in paragraph [0040] Example 1, but does not further recite what parts of the apparatus are the “fluid-type” parts, and does not state any phases for the reactants or products of the reaction. Thus, the Examiner will give the language the broadest reasonable interpretation, which is that the reactants are fluid reactants, where “fluid” is understood as a term meaning gas or liquid within the art. Appropriate clarification and amendment are respectfully requested.
With regard to claims 2-6, 8, 13, 15, 16, 19, and 23-33, the claims are rejected as being dependent on a rejected base claim.
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, 4-6, 8, 13, 15, 16, 19, and 23-33 are rejected under 35 U.S.C. 103 as being unpatentable over Calaresu et al. (US 2014/0142348).
With regard to claim 1, 5, 23, and 28, Calaresu teaches a method for alkylation of aromatic hydrocarbons with C2-C8 olefins (paragraph [0002]) with a ZSM-12 catalyst (paragraph [0040]) at a temperature of 160-250°C (paragraph [0036]). This temperature touches the claimed range of 250-400°C at 250°C, rendering the range prima facie obvious. Calaresu further teaches that the aromatic is preferably benzene (paragraph [0023]) and that the olefin is preferably cyclohexene (paragraph [0024]). Calaresu further teaches that the molar ratio of aromatic to olefin in the feed is at least 1 (paragraph [0016]). Using the molar mass of benzene of 78.11 g/mol and the molar mass of cyclohexene of 82.14 g/mol, this gives an amount of benzene in the feed of at least 59 wt%, which overlaps the ranges of 75 to 99 wt% of instant claim 1, 90 to 99 wt% of instant claim 5, 95 to 99 wt% of instant claim 23, and 90 to 95 wt% of instant claim 28, rendering the ranges prima facie obvious. Calaresu further teaches the reactor is a trickle flow (fixed bed) reactor where the benzene and cyclohexene are in vapor form (fluid-type) and alkylation product is in liquid form (fluid-type) (paragraphs [0032]-[0033]).
With regard to claims 4, 8, 25, and 31, Calaresu teaches that the pressure is 1 to 5 MPaG, the temperature is 160-250°C (paragraph [0036]) and the WHSV is 1 to 8 h-1 (paragraph [0031]). This overlaps the ranges of 0.5 to 3 MPaG, touches (overlaps) the range of 250-350°C, and is within the range of 1 to 100 h-1, wherein all the listed ranges are in each of instant claims 4, 8, 25, and 31, rendering the overlapping ranges prima facie obvious.
With regard to claims 6, 13, 15, 16, 19, 24, 26, 27, 29, 30, 32, and 33, Calaresu teaches that the reaction mixture is cooled and separated from water, then divided into two substreams, where a non-recycled part can have a purity which does not require subsequent treatment, and the desired purity of the monoalkylated aromatic product is higher than 95 wt% (paragraphs [0051]-[0052]). The monoalkylated product of the reaction of benzene and cyclohexene is known by one of ordinary skill in the art to be cyclohexylbenzene. Thus, Calaresu teaches that the alkylation produces a product comprising 95 wt% or more cyclohexylbenzene, which overlaps the ranges of 97 wt% or more of instant claims 6, 15, 16, 26, 27, 29, 30, 32, and 33 and 99 wt% or more of instant claims 13 and 19, rendering the ranges prima facie obvious. When the product comprises 95 wt% or more cyclohexylbenzene, the amount of bicyclohexyl is 5 wt% or less, which overlaps the ranges of 1 wt% or less of instant claims 6, 15, 16, 26, 27, 29, 30, 32, and 33 and 0.5 wt% or less of instant claims 13 and 19, rendering the ranges prima facie obvious.
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
/IN SUK C BULLOCK/Supervisory Patent Examiner, Art Unit 1772
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