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 .
Priority
Acknowledgment is made of applicant's claim for foreign priority based on application KR10-2021-0164915, filed November 25th, 2021 in Korea and 371 of PCT/ KR2022/018254 filed November 18th ,2022
It is noted, however, that applicant has not filed a certified copy of the English translation application as required by 37 CFR 1.55.
Failure to provide a certified translation may result in no benefit being accorded for the non-English application.
Information Disclosure Statement
The Information Disclosure Statements (IDS) filed May 22nd 2024, September 20th 2024, and March 13th 2025 were considered by the examiner.
Claim Status
Claims examined: 1-9
Claims rejected: 1-9
Claim Rejections - 35 USC § 102
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.
(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 1-3, 5, 6, 8 and 9 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Lei (Shi Lei et al., CN 109503375A, published 03/22/2019, as cited on the IDS dated 09/20/2024).
Lei teaches a production process for preparing catalyzed methyl ethyl carbonate (Abstract).
Regarding claim 1, Lei teaches that dimethyl carbonate, ethanol, and a catalyst are raw materials and entered into a first reactive distillation tower. Lei teaches that the first reaction distillation column bottom product comprises dimethyl carbonate, methyl ethyl carbonate, and diethyl carbonate. Further Lei teaches that the product diethyl carbonate as a recycled byproduct of the reaction (Pg. 5 [0009]).
Regarding Claim 2, Lei teaches the reaction taking place inside the second reaction distillation tower, that has continuous stirring of the product (Pg. 6, [0016]).
Regarding Claim 3, Lei teaches sodium methoxide as a homogenous catalyst (Pg. 6, [0018]).
Regarding Claim 8, Lei teaches diethyl carbonate as a recycled byproduct of the reaction (Pg. 6, [0015]).
Regarding Claim 9, Lei discloses the addition of extra dimethyl carbonate added to the raw materials in the reaction (Pg. 10, [0037]).
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.
Claims 4-7 are rejected under 35 U.S.C. 103 as being unpatentable over Lei (Shi Lei et al., CN 109503375A, published 03/22/2019, as cited on the IDS dated 09/20/2024).
Regarding Claim 4, Lei discloses the mole ratio of ethanol to dimethyl carbonate raw materials is 1:0.5 to 1:2 (Pg. 2, Claim 3).
In the specification of the present invention, 1.0 is disclosed as an embodiment for the lower limit of the ratio of ethanol to dimethyl carbonate, and 2.0 is disclosed as the upper limit for the ratio.
Regarding Claim 4, it would have been obvious for one of ordinary skill in the art before the effective filing date to use the mole ratio of ethanol to dimethyl carbonate disclosed in Lei for a process for preparing catalyzed methyl ethyl carbonate because Lei and the present claims both teach the same method, and an embodiment in the present application teaches the exact ratio disclosed in Lei.
Regarding Claim 5, Lei teaches the dosage of the catalyst used is 0.1% to 5% of the total weight of the raw materials (Pg. 6, [0018]).
Regarding Claim 6, Lei teaches the second reaction step taking place at 90-125 degrees Centigrade (Pg. 7, [0022]).
Regarding Claim 7, Lei teaches the mole ratio of dimethyl carbonate to diethyl carbonate is 1:1 (Pg. 6, [0015]).
Claims 5 and 6 have overlapping ranges with the temperature and total weight of the catalyst disclosed in Lei.
Regarding Claims 5 and 6, the courts found that, in the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In reWertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In reWoodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990) The prior art taught carbon monoxide concentrations of “about 1-5%” while the claim was limited to “more than 5%.” The court held that “about 1-5%” allowed for concentrations slightly above 5% thus the ranges overlapped. Therefore, it would have been prima facie obvious for one of ordinary skill in the arts before the effective filing date to optimize the temperature range of 90-125 ºC, and the dosage of the catalyst used at 0.1%-5% disclosed in Lei, to arrive at the claimed temperature range of 30-100 ºC and the claimed dosage of the catalyst used at 0.02 to 1 part by weight based on 100 parts of dimethyl carbonate because the ranges disclosed in Lei overlap with the ranges disclosed in the present claims.
Regarding Claim 7, see MPEP 2144.05: 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.” In reAller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955) (Claimed process which was performed at a temperature between 40°C and 80°C and an acid concentration between 25% and 70% was held to be prima facie obvious over a reference process which differed from the claims only in that the reference process was performed at a temperature of 100°C and an acid concentration of 10%.); see also Peterson, 315 F.3d at 1330, 65 USPQ2d at 1382 (“The normal desire of scientists or artisans to improve upon what is already generally known provides the motivation to determine where in a disclosed set of percentage ranges is the optimum combination of percentages.”). Therefore, the mole ratio of diethyl carbonate to dimethyl carbonate, and the mole ratio of ethanol to dimethyl carbonate disclosed in Lei do not overlap with the limitations in Claim 7, but would still render the claims obvious.
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 1-9 are provisionally rejected on the grounds of nonstatutory double patenting as being unpatentable over claim 1 of copending Application No. 18/713,312 in view of Lei (Shi Lei et al., CN 109503375A, published 03/22/2019, as cited on the IDS dated 09/20/2024).
Claim 1 in the copending application claims “A method for producing a carbonate comprising: a first step of producing a product containing ethyl methyl carbonate and diethyl carbonate by inducing transesterification in a raw material mixture containing dimethyl carbonate and ethanol in the presence of a catalyst;
a second step of obtaining a distillation column overhead stream and a distillation column bottom stream by distilling the product in a distillation column;
and a third step of filtering the distillation column bottom stream, wherein the distillation column bottom stream includes a catalyst with an average particle diameter (D50) of more than 1 µm”.
Claims 1-9 in the present application do not disclose a distillation column, filtering, or the average particle diameter of the filter for the catalytic process.
Lei teaches that dimethyl carbonate, ethanol and a catalyst, sodium methoxide are mixed and entered into a first reactive distillation column (Pg. 8, [0033]). Lei teaches that the first reaction distillation column bottom product comprises dimethyl carbonate and ethyl methyl carbonate, and that this bottom stream is filtered (Pg. 8, [0033]). Further, Lei teaches that the catalytic process is filtered by a 500-1000 mesh screen (Pg. 7, [0019]).
Regarding Claims 1-6 in the present application, it would have been obvious for one of ordinary skill in the art to use distillation columns and filter the product when preparing a carbonate because the process was completely disclosed in Lei for the same method of preparing a carbonate. Accordingly, claims 1-9 are not patentably distinct from claim 1 in copending application ‘312. This is a provisional nonstatutory double patenting rejection.
Conclusion
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/C.M.R./Examiner, Art Unit 1627
/Kortney L. Klinkel/Supervisory Patent Examiner, Art Unit 1627
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