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. Claim Status Claims 1, 2, 7, 8, 14, 15, 19, 21, 22, 30, 33-35, 39, 42, 44, 47, 48, 54, and 60 , as amended May 20, 2024, are currently pending. Claims 3-6, 9-13, 16-18, 20, 23-29, 31 , 32, 36-38, 40, 41, 43, 45, 46, 49-53, and 55-59 are canceled. Claim Objections Claim s 35 and 39 are objected to because of the following informalities : Claim 35 does not contain a proper status identifier (e.g., “Previously presented”) . Claim 39 recites “any one or more of the epoxide, lactone, solvent, carbon monoxide” in lines 1-2. This appears to be grammatically incorrect; “or” should be inserted prior to “carbon monoxide.” Appropriate correction is required. 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 appl icant regards as his invention. Claim s 1, 2, 7, 8, 14, 15, 19, 21, 22, 30, 33-35, 39, 42, 44, 47, 48, 54, and 60 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. Claim 1 recites “a molar ratio of epoxide/catalyst” in line 5. Claim 2 recites a “the epoxide and catalyst have a molar ratio of epoxide/catalyst” in lines 3-4. Claim 47 recites “a molar ratio of epoxide/catalyst” in line 4. Claim 54 recites “a molar ratio of epoxide/catalyst” in line 5. A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, the claim s recites the broader recitation of options of an epoxide or lactone, and then appear to limit the reactant to just an epoxide, which is the narrower statement of the limitation. The claims are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language (epoxide only) is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims. For the purpose of examination, references to “a molar ratio of epoxide/catalyst” have been interpreted as a molar ratio of epoxide or lactone to catalyst. Claim Rejections - 35 USC § 102/ 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 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. (a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention. 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, 8, 14, 15, 19, 21, 22, 30, 33-35, 44, 47, and 48 are rejected under 35 U.S.C. 102(a)(1)/(a)(2) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Sookraj (U.S. Pat. Publ’n No. 2017/0096407) (“ Sookraj ”). Regarding claims 1 , 8, 14, 15, 19, 21, 22, 33- 35 , Sookraj discloses a method of carbonylating an epoxide or lactone (abstract; [0005]; [0042]-[0044]; [0204]) comprising reacting, continuously, the epoxide or lactone in a liquid solvent with carbon monoxide in the presence of a catalyst ([0042]-[0044]; [0201], disclosing reactants entering the reactor as a solution; [0204]) . The epoxide may be ethylene oxide or propylene oxide ([0107]-[0109]; reading on claims 1 and 8 ). The solvent may be tetrahydrofuran ([0201]; reading on claims 14, 33, and 34 ). The catalyst may compris e a multidentate ligand of a porphyrin derivative that is coordinated with a metal such as aluminum, chromium, indium, or gallium ([0129]; [0145]-[0148]; [0153]-[0154]; [0187], [0189]; reading on claims 14, 15, 19, 21, and 22 ). Sookraj discloses that the carbonylation reaction proceeds at a temperature of at least 85°C to at most 130°C ([0205]; disclosing a temperature range between about 60 °C to about 140 °C ) , a carbon monoxide pressure of 700 psi to 2000 psi ([0206]; disclosing pressure ranges from about 50 psig to about 2000 psig ) and that the catalyst being present at a molar ratio of epoxide/catalyst greater than 2000 ([0207]; disclosing molar ratio of epoxide to catalyst of about 10,000, about 5,000 or about 2,500 ) . A carbonylation product is thereby formed in an effluent ([0042]-[0044]; [0208]-[0210]). With respect to the ranges for the reaction temperature and pressure, Sookraj discloses the claimed ranges with sufficient specificity to anticipate the claimed subject matter. See MPEP § 2131.03. Alternatively, i t would have been obvious to one of ordinary skill in the art at the time of invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See , e.g. , In re Wertheim , 541 F.2d 257, 191 USPQ 90 (C . C . P . A . 1976) ; In re Woodruff , 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990) . Further, Sookraj discloses that the control and optimization of these parameters is a routine matter in the field and that conditions are selected to effect efficient conversion of the epoxide to the desired products ([0204]). Although Sookraj does not explicitly disclose that the effluent ha s a concentration of water of at most 150 ppm , or at most about 75 ppm ( claims 1 and 35 ) , the reactants to the carbonylation reaction and reaction conditions in the process of Sookraj (as set forth above) are the same as those disclosed by the instant invention. Therefore, the effluent product of Sookraj will inherently have the same composition as the instant invention with respect to the concentration of water in the effluent. Alternatively, as Sookraj discloses that the control and optimization of the reaction parameters is a routine matter in the field and that conditions are selected to effect efficient conversion of the epoxide to the desired products ([0204]), it would have been obvious to one having ordinary skill in the art to adjust the reaction conditions in order to achieve the desired concentration of water in the effluent. Regarding claim 30 , Sookraj discloses all of the limitations as set forth above. Additionally, Sookraj discloses that the reactor may be a continuously stirred reactor or plug flow reactor ([0211]) . Regarding claim 44 , Sookraj discloses all of the limitations as set forth above. Additionally, Sookraj discloses that the carbonylation product is a beta lactone in the substantial absence of an anhydride ([0210]; reaction is performed to prevent formation of a succinic anhydride) . Regarding claims 47 and 48 , Sookraj discloses a method of carbonylating an epoxide or lactone (abstract; [0005]; [0042]-[0044]; [0204]) comprising reacting, continuously, the epoxide or lactone in a liquid solvent with carbon monoxide in the presence of a catalyst ([0042]-[0044]; [0201], disclosing reactants entering the reactor as a solution; [0204]). The epoxide may be ethylene oxide or propylene oxide ([0107]-[0109]). The solvent may be tetrahydrofuran ([0201]). The catalyst may comprise a multidentate ligand of a porphyrin derivative that is coordinated with a metal such as aluminum, chromium, indium, or gallium ([0129]; [0145]-[0148]; [0153]-[0154]; [0187], [0189]). Sookraj discloses that the carbonylation reaction proceeds at a temperature of at least 85°C ([0205]; disclosing a temperature range between about 60 °C to about 140 °C ) , a carbon monoxide pressure of at least 700 psi ([0206]; disclosing pressure ranges from about 50 psig to about 2000 psig ) and that the catalyst being present at a molar ratio of epoxide/catalyst greater than 2000 ([0207]; disclosing molar ratio of epoxide to catalyst of about 10,000, about 5,000 or about 2,500) . A carbonylation product is thereby formed in an effluent ([0042]-[0044]; [0208]-[0210]). The reacting step described above is performed in the absence of recycling of the catalyst ([0042]-[0044]; [0204]; [0005], catalyst recycling is not performed in real-time with the reacting step; reading on claim 48 ). With respect to the ranges for the reaction temperature and pressure, Sookraj discloses the claimed ranges with sufficient specificity to anticipate the claimed subject matter. See MPEP § 2131.03. Alternatively, i t would have been obvious to one of ordinary skill in the art at the time of invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See , e.g. , In re Wertheim , 541 F.2d 257, 191 USPQ 90 (C . C . P . A . 1976) ; In re Woodruff , 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990) . Further, Sookraj discloses that the control and optimization of these parameters is a routine matter in the field and that conditions are selected to effect efficient conversion of the epoxide to the desired products ([0204]). Although Sookraj does not explicitly disclose that the effluent is substantially in the absence of a by-product polymer and having a concentration of water of at most 150 ppm , the reactants to the carbonylation reaction and reaction conditions in the process of Sookraj (as set forth above) are the same as those disclosed by the instant invention. Therefore, the effluent product of Sookraj will inherently have the same composition as the instant invention with respect to the concentration of by-product polymer and water in the effluent. Alternatively, as Sookraj discloses that the control and optimization of the reaction parameters is a routine matter in the field and that conditions are selected to effect efficient conversion of the epoxide to the desired products ([0204]), it would have been obvious to one having ordinary skill in the art to adjust the reaction conditions in order to achieve the desired concentration of by-product polymer and water in the effluent. Claims 2 and 7 are rejected under 35 U.S.C. 103 as being unpatentable over Sookraj (U.S. Pat. Publ’n No. 2017/0096407) (“ Sookraj ”), as applied to the claims above. Regarding claims 2 and 7 , Sookraj discloses all of the claim limitations as set forth above. In particular, Sookraj discloses that the carbonylation reaction proceeds at a temperature of at least 85°C to at most 130°C ([0205]; disclosing a temperature range between about 60 °C to about 140 °C ) , a carbon monoxide pressure of 700 psi to 2000 psi ([0206]; disclosing pressure ranges from about 50 psig to about 2000 psig ) and that the catalyst being present at a molar ratio of epoxide/catalyst greater than 2000 ([0207]; disclosing molar ratio of epoxide to catalyst of about 10,000, about 5,000 or about 2,500) . With respect to the ranges for the reaction temperature and pressure, Sookraj discloses the claimed ranges with sufficient specificity to anticipate the claimed subject matter. See MPEP § 2131.03. Alternatively, i t would have been obvious to one of ordinary skill in the art at the time of invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See , e.g. , In re Wertheim , 541 F.2d 257, 191 USPQ 90 (C . C . P . A . 1976) ; In re Woodruff , 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990) . Sookraj does not explicitly disclose the molar ratio of carbon monoxide to epoxide being from 1.2 to 20. The reference does disclose, however, that the ratio of reactants to each other affect the reaction speed and efficiency ([0204]). Further, Sookraj discloses that the control and optimization of these parameters is a routine matter in the field and that conditions are selected to effect efficient conversion of the epoxide to the desired products ([0204]). Therefore, a s the reaction speed and efficiency are variables that can be modified, among others, by adjusting the molar ratio of carbon monoxide to epoxide in the carbonylation reaction , the precise molar ratio would have been considered a result effective variable by one having ordinary skill in the art at the time the invention was made. As such, without showing unexpected results, the claimed molar ratio cannot be considered critical. Accordingly, one of ordinary skill in the art at the time the invention was made would have optimized, by routine experimentation, the molar ratio of carbon monoxide to epoxide in the reaction of Sookraj to obtain the desired reaction speed and efficiency ( In re Boesch, 617 F.2d. 272, 205 USPQ 215 (C . C . P . A . 1980)), since it has been held that where the general conditions of the claim are disclosed in the prior art, discovering the optimum or workable ranges involves only routine skill in the art ( In re Aller , 105 USPQ 233, 235 (C . C . P . A . 1955) ). Claim 39 is rejected under 35 U.S.C. 103 as being unpatentable over Sookraj (U.S. Pat. Publ’n No. 2017/0096407) (“ Sookraj ”), as applied to the claims above , and further in view of Luinstra et al. (U.S. Pat. Publ’n No. 2005/0256320) (“ Luinstra ”). Re garding claim 39 , Sookraj discloses all of the claim limitations as set forth above. While Sookraj discloses that the reaction conditions may be optimized to effect efficient conversion of the epoxide to the desired products ([0204]), the reference does not explicitly disclose that any one or more of the epoxide, solvent, or carbon monoxide are dried prior to reacting. Luinstra discloses methods for the preparation of lactones through catalytic carbonylation reactions ([0001]). The reaction can be carried out at superatomospheric pressure and elevated temperatures ([0034]; disclosing pressures from about 145 psi to about 3625 psi, and temperatures from 20 to 150 °C ). The epoxide for the reaction may be ethylene oxide ([0037]) and solvents may include tetrahydrofuran ([0035]). Luinstra teaches that solvents used in the reaction are dried over molecular sieves and degassed before use ([0053]). The reference suggests that this method represents an uncomplicated and efficient process for the carbonylation reaction of epoxides ([0010]). It would have been obvious to one having ordinary skill in the art at the time of the invention to pretreat at least the solvent in the method of Sookraj by drying the solvent over a molecular sieve and degassing, as suggested by Luinstra , since doing so represents a known pretreatment step for reagents in a carbonylation reaction of epoxides and will further optimize the efficient conversion of the epoxide to the desired products. Claim 42 is rejected under 35 U.S.C. 103 as being unpatentable over Sookraj (U.S. Pat. Publ’n No. 2017/0096407) (“ Sookraj ”), as applied to the claims above , and further in view of Nguyen et al. (U.S. Pat. Publ’n No. 2006/0257293) (“Nguyen”) . Re garding claim 42 , Sookraj discloses all of the claim limitations as set forth above. Sookraj teaches that the solvent, catalyst, and epoxide may be fed together to the reactor and may be preheated before entering the reactor ([0201]; disclosing that the reactants may be fed into the reactor in separate streams or with solvent fed to reactor along with catalyst and epoxide; [0205]) and the carbon monoxide is fed into the reactor ([0206]). Additionally, Sookraj discloses that the reactor may be a plug flow reactor ([0211]) . Sookraj does not explicitly disclose the molar ratio of carbon monoxide to epoxide being from 1.2 to 20. The reference does disclose, however, that the ratio of reactants to each other affect the reaction speed and efficiency ([0204]). Further, Sookraj discloses that the control and optimization of these parameters is a routine matter in the field and that conditions are selected to effect efficient conversion of the epoxide to the desired products ([0204]). Therefore, a s the reaction speed and efficiency are variables that can be modified, among others, by adjusting the molar ratio of carbon monoxide to epoxide in the carbonylation reaction , the precise molar ratio would have been considered a result effective variable by one having ordinary skill in the art at the time the invention was made. As such, without showing unexpected results, the claimed molar ratio cannot be considered critical. Accordingly, one of ordinary skill in the art at the time the invention was made would have optimized, by routine experimentation, the molar ratio of carbon monoxide to epoxide in the reaction of Sookraj to obtain the desired reaction speed and efficiency ( In re Boesch, 617 F.2d. 272, 205 USPQ 215 (C . C . P . A . 1980)), since it has been held that where the general conditions of the claim are disclosed in the prior art, discovering the optimum or workable ranges involves only routine skill in the art ( In re Aller , 105 USPQ 233, 235 (C . C . P . A . 1955) ). While Sookraj discloses that the reactor may be a plug flow reactor and that there are no particular limits on the type, size, or geometry of the reactor ([0211]), the reference does not explicitly state that the reactor is a vertical plug flow reactor. Nguyen discloses a plug flow reactor used to prepare compositions (abstract). Nguyen teaches that is it known to configure plug flow reactors as vertical vessels as well as horizontal vessels and that one in the art would make selections for the vessel based on compatibility with the product fluid using techniques known in the art ([0027]). It would have been obvious to one having ordinary skill in the art at the time of the invention to select a vertical plug flow reactor among known options of vertical and horizontal plug flow reactors for the plug flow reactor of Sookraj , as suggested by Sookraj and Nguyen, since Sookraj indicates there are no particular limits on the geometry of the reactor and Nguyen teaches that one in the art would make selections for a reactor vessel based on compatibility with the particular reaction and reactants using known techniques in the art. Claim s 54 and 60 are rejected under 35 U.S.C. 103 as being unpatentable over Sookraj (U.S. Pat. Publ’n No. 2017/0096407) (“ Sookraj ”) in view of Luinstra et al. (U.S. Pat. Publ’n No. 2005/0256320) (“ Luinstra ”). Regarding claims 54 and 60 , Sookraj discloses a method of carbonylating an epoxide or lactone (abstract; [0005]; [0042]-[0044]; [0204]) comprising reacting, continuously, the epoxide or lactone in a liquid solvent with carbon monoxide in the presence of a catalyst ([0042]-[0044]; [0201], disclosing reactants entering the reactor as a solution; [0204]). The epoxide may be ethylene oxide or propylene oxide ([0107]-[0109]). The solvent may be tetrahydrofuran ([0201]). The catalyst may comprise a multidentate ligand of a porphyrin derivative that is coordinated with a metal such as aluminum, chromium, indium, or gallium ([0129]; [0145]-[0148]; [0153]-[0154]; [0187], [0189]). Sookraj discloses that the carbonylation reaction proceeds at a temperature of at least 85°C ([0205]; disclosing a temperature range between about 60 °C to about 140 °C ) , a carbon monoxide pressure of at least 700 psi ([0206]; disclosing pressure ranges from about 50 psig to about 2000 psig ) and that the catalyst being present at a molar ratio of epoxide/catalyst greater than 2000 ([0207]; disclosing molar ratio of epoxide to catalyst of about 10,000, about 5,000 or about 2,500) . A carbonylation product is thereby formed in an effluent ([0042]-[0044]; [0208]-[0210]). With respect to the ranges for the reaction temperature and pressure, Sookraj discloses the claimed ranges with sufficient specificity to anticipate the claimed subject matter. See MPEP § 2131.03. Alternatively, i t would have been obvious to one of ordinary skill in the art at the time of invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See , e.g. , In re Wertheim , 541 F.2d 257, 191 USPQ 90 (C . C . P . A . 1976) ; In re Woodruff , 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990) . Further, Sookraj discloses that the control and optimization of these parameters is a routine matter in the field and that conditions are selected to effect efficient conversion of the epoxide to the desired products ([0204]). While Sookraj discloses that the reaction conditions may be optimized to effect efficient conversion of the epoxide to the desired products ([0204]) and that the carbon monoxide may be supplied in a pure form ([0124]), the reference does not explicitly disclose that the epoxide and solvent have a total water concentration of at most 40 ppm, or at most 20 ppm. Luinstra discloses methods for the preparation of lactones through catalytic carbonylation reactions ([0001]). The reaction can be carried out at superatomospheric pressure and elevated temperatures ([0034]; disclosing pressures from about 145 psi to about 3625 psi, and temperatures from 20 to 150 °C ). The epoxide for the reaction may be ethylene oxide ([0037]) and solvents may include tetrahydrofuran ([0035]). Luinstra teaches that solvents used in the reaction are dried over molecular sieves and degassed before use ([0053]). The reference suggests that this method represents an uncomplicated and efficient process for the carbonylation reaction of epoxides ([0010]). It would have been obvious to one having ordinary skill in the art at the time of the invention to pretreat the liquid reactants in the method of Sookraj to reduce the water concentration in the reactants to at most 20 ppm by drying the reactants over a molecular sieve and degassing, as suggested by Luinstra , since doing so represents a known pretreatment step for reagents in a carbonylation reaction of epoxides and will further optimize the efficient conversion of the epoxide to the desired products. Conclusion The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Any inquiry concerning this communication or earlier communications from the examiner should be directed to FILLIN "Examiner name" \* MERGEFORMAT KATHERINE M ZALASKY MCDONALD whose telephone number is FILLIN "Phone number" \* MERGEFORMAT (571) 270-7064 . The examiner can normally be reached FILLIN "Work Schedule?" \* MERGEFORMAT M-F, 9:00 AM to 5:30 PM . Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, FILLIN "SPE Name?" \* MERGEFORMAT JACOB BETIT can be reached at FILLIN "SPE Phone?" \* MERGEFORMAT (571) 272-4075 . The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /KATHERINE ZALASKY MCDONALD/ Primary Examiner, Art Unit 6221