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.
Claim Amendments
Applicant’s amendments to the claims filed on 28 July 2026 have not been entered, because the amendments to claim 1 redirect the claims to only non-elected species.
Accordingly, the action below is made with respect to the claim set filed 27 April 2026.
New Examiner
This application has been transferred to a new examiner, Nicholas Piro of Art Unit 1738, who can be reached at 571-272-6344.
Election/Restrictions
Claims 6-11 stand withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 11 November 2025 and further clarified in the Interview conducted on 24 December 2025.
Claims 15-20 stand withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 11 November 2025.
Response to Arguments
Applicant’s arguments, see page 11-12 of the reply filed 28 July 2026, with respect to the rejection of claim 14 under 35 USC § 103 have been fully considered and are persuasive: Yu does not teach the conditions under which a cyclic carbonate is prepared from an epoxide and carbon dioxide, and therefore the use of Yu’s temperature and pressure conditions in the method of Zhou is not appropriate. The prior rejection of claim 14 has been withdrawn.
However, upon further consideration a new ground of rejection for claim 14 is made in view of Xia (CN 1275960 C), as analyzed below.
The rejections of claims 5 and 13 have also been modified and are now presented under 35 USC § 103.
The finality of the Office action mailed 28 July 2026 is withdrawn, and this action is NOT FINAL.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1-4 and 12 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Zhou et al. (CN 108440487 A, published on 08/24/2018). The newly provided English machine translation of Zhou (CN 108440487 A) is relied upon in the analysis below.
Regarding claim 1, Zhou et al. teach a method for preparing a cyclic carbonate by using a catalyst for catalyzing a reaction of an epoxide compound (epichlorohydrin; Example 1) and carbon dioxide, wherein the catalyst comprises a quaternary ammonium salt compound having the formula below where R is an alkyl group and B is nitrogen, and X is a halide (claim 7 and [0025] of the original, copied below), where the method comprises adding the catalyst in a reactor introducing the epoxide compound into the reactor, and introducing carbon dioxide into the reactor to adjust the pressure of the reaction system to allow the epoxide compound to react with carbon dioxide and generate the cyclic carbonate (In a 50 mL stainless steel high-pressure reactor, [epoxide, catalyst, and co-catalyst] were added. The reactor was sealed, and carbon dioxide was continuously introduced to maintain the pressure inside the reactor at 0.1 MPa….to obtain the product 4-chloromethyl-[1,3]dioxane-2-one cyclic carbonate; Examples 1, 5, and 7).
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Regarding claims 2-4, Zhou discloses the method of claim 1, where R is ethyl, an alkyl group of 2 carbons, and X is bromide (N-diethylpyrrol[idine] bromide; Example 5). It is noted that while the translation refers to compounds of the formula represented in the figure above as a “pyrrole” quaternary ammonium salt, the structures reveal them to be the unsaturated pyrrolidine quaternary ammonium salts.
Regarding claim 12, Zhou discloses the method of claim 1, where the epoxide compound taught by Zhou is epichlorohydrin (Examples 1, 5, and 7) which corresponds to the instant formula (3), wherein R2=H and R3=CH2Cl.
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.
9. 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 5 and 13 are rejected under 35 U.S.C. 103 as being unpatentable over Zhou et al. (CN 108440487 A, published on 08/24/2018). The newly provided English machine translation of Zhou (CN 108440487 A) is relied upon in the analysis below.
Regarding claim 5, Zhou discloses the method of claim 1, where Zhou teaches a specific embodiment where R is ethyl and X is bromide (Example 5). Zhou further teaches that the catalyst may also have the general structure illustrated in [0025] and copied above, where in addition to ethyl, R may be methyl, a C1 alkyl (Wherein R1 is H or methyl or the same as R2; R2 is a C1 to C6 alkyl group; [0027]-[0029] of the translation, [0024]-[0026] of the original).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to replace the N,N-diethylpyrrolidinium bromide of Example 5 with N,N-dimethylpyrrolidinium bromide, thereby arriving at the instantly claimed invention. One of ordinary skill in the art would have been motivated to do so because Zhou teaches that compounds with both substitution patterns would make effective catalysts.
Regarding claim 13, Zhou discloses the method of claim 1, where Zhou teaches a molar ratio of catalyst to epoxide reactant being 0.004 mol to 0.1 mol (Example 5, with reference to Example 1), which is equivalent to a ratio of 4 x 10-2 :1, which lies outside the instantly claimed range.
However, Zhou also teaches that the epoxide to catalyst ratio may be in the range of 2000:1 to 10:1 ([0034]), which is equivalent to a catalyst to epoxide ratio of (0.5 x 10-3 to 10 x 10-2):1, which overlaps with the instantly claimed range.
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.
Claim 14 is rejected under 35 U.S.C. 103 as being unpatentable over Zhou et al. (CN 108440487 A, published on 08/24/2018), as applied to claim 1 above, and further in view of Xia et al. (CN 1275960 C). The newly provided English machine translations of Zhou (CN 108440487 A) and Xia (CN 1275960 C) are relied upon in the analysis below.
Regarding claim 14, Zhou discloses the method of claim 1, but Zhou does not specifically disclose the pressure being 1 to 5 MPa or a temperature in the range of 100-200 0C, as required by the instant claim. Zhou does disclose that their reactions take place over 48 hours (Example 1).
However, it would be well understood by one of ordinary skill in the art that as reaction temperature increases, so does reaction rate, and that therefore reaction time can be decreased by increasing reaction temperature.
Furthermore, Xia also teaches a process wherein a quaternary ammonium salt catalyzes the reaction of an epoxide with carbon dioxide to produce a cyclic carbonate product ([0010]), and Xia further teaches that temperatures in the range of 50 °C to 200 °C and pressures of 0.5 to 5 MPa can be used, and that such reactions proceed in only 0.5 to 6 hours ([0010]).
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to increase the temperature and pressure of reaction used in the method of Zhou, including into the instantly claimed range of 100 °C to 200 °C and 1 to 5 MPa, as taught by Xia. One of ordinary skill in the art would have been motivated to do so in order to increase reaction rate and carry out the reaction in less time.
Furthermore, generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. "[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation." See MPEP 2144.05 and In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). Therefore the claimed range of temperature merely represents an obvious variation or routine optimization of the conditions in the cited prior art.
It is noted that while Zhou teaches their operating conditions are preferable those of higher temperatures used in other prior art ([0007]), such an observation would not discourage one of ordinary skill in the art from utilizing higher temperatures when other concerns, like increasing yield or rate, would otherwise point in that direction.
Conclusion
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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