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 .
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.
Amendments
Applicant’s amendments to the claims filed 2 September 2026 have been entered and considered for this action. These amendments overcome the prior claim rejections under 35 USC § 103, which are withdrawn.
Claim Interpretation
The claim interpretations set forth in the prior Office action mailed 2 May 2025 were acknowledged by Applicant in the reply filed 2 October 2025 and continue to be used.
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 12-14 are rejected under 35 U.S.C. 103 as being unpatentable over Okada et al. (Japanese Pat. App. JP 2007269522A) in view of Modisha et al. (Sust. Energy Fuels 2020, 4, 4662-4670; published 1 July 2020). The provided English machine translation of Okada (JP 2007269522 A) is referenced in the analysis below.
Regarding claim 12, Okada teaches a process for purifying an aromatic liquid compound (dimethylbiphenyl mixtures, column 9, lines 49-51), said process comprising the following steps:
providing an aromatic liquid comprising at least one impurity, wherein the impurity is a degradation byproduct of the aromatic liquid compound and is generated by degradation of the aromatic liquid compound ([0048]); and,
contacting said aromatic liquid with at least one zeolitic adsorbent material so as to absorb said at least one impurity onto the at least one zeolitic adsorbent material to produce a purified aromatic liquid ([0069]).
Regarding the level by which the impurities are reduced, Okada further teaches that the impurities may be present at several tens to hundreds of ppm ([0062]) and the impurity removal device can be used to separate and remove as much of the impurities (reaction inhibitors) as possible, including to levels below 10 ppm in order to extend the operating time of the system ([0070]).
While it may be unclear to which impurity removal device Okada is referring in [0070], the distillation device of the adsorption device, in either case it would have been obvious to one of ordinary skill in the art to operate the adsorption device such that recovering the purified aromatic liquid comprised said at least one impurity at a concentration by weight of less than 50% by weight relative to the level of said impurity present in the liquid, the at least one impurity having been reduced by the adsorption of step b. One of ordinary skill in the art would have been motivated to do so in order to reduce the impurity levels as much as possible in order to extend the operating time of the system.
Okada also teaches that when the aromatic liquid serving as the LOHC (hydrogen storage body; [0015]) is toluene/methylcyclohexane the impurities present include benzene, dimethylcyclohexane, bicyclohexyl and/or hydrogenated homologs thereof (Fig. 1 and [0052]).
Okada does not teach the aromatic liquid being any of those recited in the claim.
However, Modisha also teaches about liquid organic hydrogen carrier systems (abstract), and Modisha further teaches that dibenzyltoluene is the most preferred liquid organic hydrogen carrier (p. 4662, ¶ 2). Modisha additionally teaches that the degradation products of this aromatic liquid include benzene, toluene and xylenes (Fig. 9 and p. 4668, col. 2, ¶ 2). Like Okada, Modisha also teaches applying a purification to remove undesired by-products (p. 4666, col. 1, ¶ 3).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to apply a zeolitic adsorption method of Okada to remove impurities such as xylene that are generated from the degradation of the aromatic liquid dibenzyltoluene, as taught by Modisha. One of ordinary skill in the art would have been motivated to do so because Modisha teaches that dibenzyltoluene is a preferred substitute for toluene and because Okada and Modisha each teach that purification of the aromatic liquid is desirable.
Regarding claim 13, modified Okada teaches the process of claim 12 where Modisha teaches said aromatic liquid comprising dibenzyltoluene, which has at least one aromatic ring in the nonhydrogenated form.
Regarding claim 14, modified Okada teaches the process of claim 12 where Modisha teaches said aromatic liquid comprising dibenzyltoluene, which corresponds to the formula (A-X)n-B, where n is equal to zero and B is an aromatic ring substituted with one saturated C1 hydrocarbon radical and (methyl) and two partially unsaturated C7 hydrocarbon radicals (benzyl).
Claims 16-20 and 22 are rejected under 35 U.S.C. 103 as being unpatentable over Okada et al. (Japanese Pat. App. JP 2007269522A) in view of Modisha et al. (Sust. Energy Fuels 2020, 4, 4662-4670; published 1 July 2020), as applied to claim 12 above, and further in view of Marme et al. (“Studies on the Use of Synthetic Zeolites for the Purification and Isolation of Value-Added Chemicals,” Proceedings of the 2nd Polish-German Zeolite Colloquium, Torun, Poland, Apr. 20-22, 1995. Pp. 243-252; cited and provided with PTO-892 mailed 2 June 2026), and with respect to claim 16, as evidenced by Argauer et al. (US 3702886 A). The provided English machine translation of Okada (JP 2007269522 A) is relied upon in the analysis below.
Regarding claims 16, modified Okada teaches the process of claim 12 but is silent on the identity and form of the zeolitic adsorbent.
However, Marme also teaches that synthetic zeolites can be used to purify aromatic liquid compounds and further teaches that ZSM-5 in particular is well suited to adsorb small molecules from liquids comprised of larger molecules (p. 246, ¶ 1). Argauer provides evidence that ZSM-5 is a crystalline zeolite (col. 1, line 15), and can therefore be considered as existing in the form of crystals.
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to use ZSM-5 as the zeolitic adsorbent in the method of modified Okada, as taught by Marme, which is a zeolite in the form of crystals, as evidenced by Argauer. One of ordinary skill in the art would have been motivated to do so because Marme teaches that this zeolite may be used to purify organic liquids comprised of large molecules by adsorbing smaller molecules, which is situation one of ordinary skill would recognize as applicable to removing the xylene impurities from dibenzyltoluene.
Regarding claims 17, 19, and 22, modified Okada teaches the process of claim 12 but is silent on the identity of the zeolitic adsorbent.
However, Marme also teaches that synthetic zeolites can be used to purify aromatic liquid compounds and further teaches that ZSM-5 in particular is well suited to adsorb small molecules from liquids comprised of larger molecules (p. 246, ¶ 1), and that the ZSM-5 may have a Si/Al (module) of 27 or lower or greater than 200 (Table 4), each of which overlaps with the claimed range of between 8 and 500. ZSM-5 is MFI type per instant specification (page 9 lines 29-33).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to use in the method of modified Okada a synthetic zeolite of type MFI (ZSM-5) having an atomic ratio Si/Al of 27 or less or greater than 200, as taught by Marme. One of ordinary skill in the art would have been motivated to do so because Marme teaches that this zeolite may be used to purify organic liquids comprised of large molecules by adsorbing smaller molecules, which is situation one of ordinary skill would recognize as applicable to removing the xylene impurities from dibenzyltoluene.
It is noted that the courts have stated where the claimed ranges “overlap or lie inside the ranges disclosed by the prior art” a prima facie case of obviousness exists (see In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990); Titanium Metals Corp. of America v. Banner, 778 F2d 775. 227 USPQ 773 (Fed. Cir. 1985) (see MPEP 2144.05.01). Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
Regarding claims 18 and 20, modified Okada teaches the process of claim 12 but is silent on the identity of the zeolitic adsorbent.
However, Marme also teaches that synthetic zeolites can be used to purify aromatic liquid compounds and further teaches that zeolite Y is well suited to adsorb non-polar molecules (p. 246, ¶ 2). Marme further teaches that zeolite Y comprising sodium (Na), potassium (K), strontium (Sr), and barium (Ba) have been effective at separating xylene-containing mixtures (Table 1, rows 1-2).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to use zeolite Y, an FAU type zeolite, comprising sodium, potassium, strontium, and/or barium in order to remove xylene impurities in the method of modified Okada, thereby arriving at the invention of claims 18 and 20. One of ordinary skill in the art would have been motivated to do so because Marme teaches that this zeolite has high adsorption ability, is suitable for non-polar compounds, and has been employed successfully in separations of aromatic mixtures that include xylene.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 12-14 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 9, 10, and 12-17 of copending Application No. 17/998,938. Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of the co-pending application teach the purification of aromatic liquids having the instantly claimed structures using zeolites.
Claim 12 of the cited ’938 application teaches using zeolites to remove oxygenated degradation productions, which would include phenol of instant claim 12, from an aromatic liquid and claim 14 of the ‘938 application teaches the aromatic liquid being the same as those of instant claim 12.
Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to purify the aromatic liquids recited in claim 14 of the ‘938 application to remove phenol using a zeolitic adsorbent.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claim 16-20 and 22 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 9, 10, and 12-17 of copending Application No. 17/998,938, as applied to instant claim 12 above, and further in view of Marme et al. (“Studies on the Use of Synthetic Zeolites for the Purification and Isolation of Value-Added Chemicals,” Proceedings of the 2nd Polish-German Zeolite Colloquium, Torun, Poland, Apr. 20-22, 1995. Pp. 243-252; cited and provided with PTO-892 mailed 2 June 2026).
The claims of the ‘938 application teach the method of instant claim 12, but do not teach the limitations on zeolitic adsorbent material recited in instant claims 16-20 and 22.
However, Marme teaches that zeolites such as ZSM-5 (p. 246, ¶ 1) and zeolite Y that includes sodium (Na), potassium (K), strontium (Sr), and barium (Ba) (p. 246, ¶ 2 and Table 1) are effective at purifying aromatic liquids. Therefore, it would have been obvious to use any of these zeolites in the method of the ‘938 patent, thereby arriving at the inventions of the instant claims.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Response to Arguments
Applicant’s arguments, pages 7-9 of the reply filed 2 September 2026, with respect to the rejection(s) of claims 12-14, 16-19, and 22 under 35 USC § 103 have been fully considered and are persuasive: the combination of Paek and Dakka does not teach all the limitations of the amended claim. Therefore, the rejection has been withdrawn. However, upon further consideration, a new grounds of rejection is made in view of Okada and Modisha, and with respect to claims 16-20 and 22, further in view or Marme, as analyzed above.
Applicant’s intent to file a terminal disclaimer in order to overcome the non-statutory double patenting rejection is noted. Until such time as that disclaimer is filed the rejections are maintained.
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 Nicholas A Piro whose telephone number is (571)272-6344. The examiner can normally be reached Mon-Fri, 8:00 am-5:00 pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Sally Merkling can be reached at (571) 272-6297. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/NICHOLAS A. PIRO/Assistant Examiner, Art Unit 1738
/PAUL A WARTALOWICZ/Primary Examiner, Art Unit 1735
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