DETAILED ACTION
STATUS OF THE APPLICATION
Receipt is acknowledged of Applicants’ Amendments and Remarks, filed 26 December 2025, in the matter of Application No. 18/043,960. Said documents have been entered on the record. The Examiner further acknowledges the following:
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 1-12 are pending.
Claims 1-8 and 10-11 have been amended.
Claims 13-19 have been cancelled.
Thus, claims 1-12 represent all claims currently under consideration.
Information Disclosure Statement (IDS)
The information disclosure statements submitted on 7 October 2025 and 19 December 2025 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the Examiner.
REJECTIONS WITHDRAWN
The status for each rejection and/or objection in the previous Office Action is set out below.
Specification Objections
Applicant’s amendments to the written description have fully overcome the objections to the specification.
Claim Objections
Applicant’s amendments and cancellation of claims 13-19 have fully overcome the claim objections.
35 U.S.C.§ 102
Applicant’s cancellation of claims 13-19 have fully overcome the rejections of claims 13-19 under 35 U.S.C. 102(a)(1) as being anticipated by Hameed et al. (ChemSusChem 2019, 12, 3453-3457; IDS of 03-03-2013, NPL Cite No. 4; hereinafter “Hameed”) and the rejections of claims 13-18 under 35 U.S.C. 102(a)(1) as being anticipated by Benito-Garagorri et al. (Organometallics 2006, 25, 1900-1913; IDS of 04-09-2025, NPL Cite No. 3; hereinafter “Benito-Garagorri”).
35 U.S.C.§ 103
Applicant’s amendments and cancellation of claims 13-19 have fully overcome the rejections of claims 1-9 and 12-19 under 35 U.S.C. 103 as being unpatentable over Huang et al. (WO 2015/083007 A1; IDS of 10-31-2024; hereinafter “Huang”), in view of Hameed et al. (ChemSusChem 2019, 12, 3453-3457; IDS of 03-03-2013, NPL Cite No. 4; hereinafter “Hameed”), and the rejections of claims 10-11 under 35 U.S.C. 103 as being unpatentable over Huang, Hameed, and N.G. Anderson (Practical Process & Research Development, 2000, pages 46-47, 61-62, 98, 132, 169, and 239; PTO-892 of 10-01-2025; hereinafter “Anderson”).
In the response filed 26 December 2025, Applicant’s amendment to claim 1 further limited the scope of the claimed method as (1) comprising reacting hydrogen with a hydrogen carbonate or a carbonate; and (2) a phase transfer catalyst is further used. As a result of these amendments, new rejections for claims 1-12 have been applied as detailed herein, wherein the limitation (1) has been addressed by the teachings of newly cited prior art reference Guan et al. (Green Chem. 2018, 20, 4201-4205; hereinafter “Guan”) and the limitation (2) has been addressed by the teachings of previously cited prior art reference N. G. Anderson (Practical Process & Research Development, 2000, pages 46-47, 61-62, 98, 132, 169, and 239; PTO-892 of 10-01-2025; hereinafter “Anderson”) in a manner consistent with the previous rejections of claims 10-11 of the Office Action mailed 1 October 2025.
Double Patenting
Applicant’s cancellation of claims 13-14 have fully overcome the provisional nonstatutory double patenting rejections of claims 13-14 over claims 1, 10-11, and 13-14 of copending Application No. 18/840,951, the provisional nonstatutory double patenting rejections of claims 13-14 over claims 1 and 4-8 of copending Application No. 18/043,973, and the provisional nonstatutory double patenting rejections of claims 13-14 over claims 1, 5, 7-9 of copending Application No. 18/043,928. In addition, Applicant’ amendments and cancellation of claims 13-14 have fully overcome the provisional nonstatutory double patenting rejections of claims 1-2 and 12-14 over claims 1-4, 6-7, and 11 of copending Application No. 18/841,329,
In response to Applicant’s amendments filed 26 December 2025, the provisional nonstatutory double patenting rejections were maintained and modified for the claims of ‘951, ‘973, and ‘928. In addition, regarding the claims of ‘329, new provisional nonstatutory double patenting rejections were applied as necessitated by amendment, wherein claims 1-2 and 10-12 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-4, 6-7, and 11 of copending Application No. 18/841,329 in view of N.G. Anderson (Practical Process & Research Development, 2000, pages 46-47, 61-62, 98, 132, 169, and 239; PTO-892 of 10-01-2025; hereinafter “Anderson”), as detailed herein, wherein the teachings of Anderson address the newly added claim limitation of a phase transfer catalyst in the method of amended claims 1 as well as the features of claims 10-11.
REJECTIONS-MAINTAINED, MODIFIED, & NEW
The below rejections are modified in view of the amendments to the claims. Modifications are bolded below.
NEW Claim Rejections - 35 USC § 103 – Necessitated by Amendment
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.
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.
Claims 1-12 are rejected under 35 U.S.C. 103 as being unpatentable over Huang et al. (WO 2015/083007 A1; IDS of 10-31-2024; hereinafter “Huang”), in view of Guan et al. (“Conversion of CO2 form air into formate using amines and phosphorus-nitrogen PN3P-Ru(II) pincer complexes”; Green Chem. 2018, 20, 4201-4205; hereinafter “Guan”), Hameed et al. (“Visible-Light Photocatalytic Reduction of CO2 to Formic Acid with a Ru Catalyst Supported by N,N’-Bis(diphenylphosphino)-2,6-diaminopyridine Ligands”; ChemSusChem 2019, 12, 3453-3457; IDS of 03-03-2013, NPL Cite No. 4; hereinafter “Hameed”) and N.G. Anderson (Practical Process & Research Development, 2000, pages 46-47, 61-62, 98, 132, 169, and 239; PTO-892 of 10-01-2025; hereinafter “Anderson”).
Regarding claim 1 and claims 2 and 9-11 depending from claim 1, Huang teaches phosphor-amino pincer-type ligands, metal complexes thereof, and catalytic methods comprising such metal complexes, wherein (Huang; Abstract). Huang further teaches that in certain aspects of the present invention, there are provided a new class of pincer-type ligands, including those having a disubstituted-phosphinoamino (NH-PR2) arm; metal complexes of such ligands are also provided, including complexes that may be used as catalysts for a variety of transformations, including conversion of formic acid to carbon dioxide and hydrogen or hydrogenation of carbon dioxide to form a formate or formic acid (Huang; paragraph [016]). Of particular note, Huang teaches a method to produce formic acid or a formate, comprising the step of contacting carbon dioxide and hydrogen under increased pressure relative to atmospheric pressure with a complex comprising a ligand and a metal or metal ion, wherein the ligand is a compound according to formula (IV), or a deprotonated version thereof, and the ligand is associated with the metal or metal ion, wherein formula (IV) comprises:
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wherein Rl, R2, R3, and R4 are each independently alkyl(C≤12), aryl(C≤12), aralkyl((C≤12), or a substituted version of any of these groups; R5 is a hydrogen atom or an alkyl(C≤12), aryl(C≤12), aralkyl(C≤12), or a substituted version of any of these groups; each Z, independently, is CR6, N or P; and R6 is a hydrogen atom or an alkyl(C≤12), aryl(C≤12), aralkyl(C≤12), amino, hydroxyl, alkoxyl or a substituted version of any of these groups, such that formic acid or a formate is produced (Huang; claim 82). In addition, Huang teaches a composition comprising a compound of formula (V):
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wherein Rl, R2, R3, and R4 are each independently alkyl(C≤12), aryl(C≤12), aralkyl(C≤12), or a substituted version of any of these groups; R5 is a hydrogen atom or an alkyl(C≤12), aryl(C≤12), aralkyl(C≤12), or a substituted version of any of these groups; each Z, independently, is CR6, N or P; R6 is a hydrogen atom or an alkyl(C≤12), aryl(C≤12), aralkyl(C≤12), amino, hydroxyl, alkoxyl or a substituted version of any of these groups; M is a metal or metal ion that is a group 8 metal or metal ion; L is a neutral or an anionic ligand; n is 0, 1 or 2; X is a halide or a hydrogen atom; and provided that when R1, R2, R3 and R4 are t-butyl groups, R5 is not a hydrogen atom and each Z is not CH and when R1, R2, R3 and R4 are isopropyl groups, R5 is not a phenyl group and each Z is not N (Huang; claim 54). This genus reads directly on Formula 1 of instant claim 1 and Formula 3 of instant claim 2 when R0 is hydrogen or an alkyl(C≤12) group; Q1 is NH (as in instant claim 1), or Q2 is NH (as in instant claim 2); R1 is an alkyl(C≤12) group or an aryl(C≤12) group provided that at least one of R1 represents an aryl group (as in instant claim 1), or R3 is an aryl(C≤12) group (as in instant claim 2); A is CH, CR5 or N, wherein R5 represents an alkyl(C≤12), aryl(C≤12), aralkyl(C≤12), amino, hydroxy, or alkoxy group; X represents a halogen atom; n represents 0 to 2; and L represents a neutral or anionic ligand.
Finally, further regarding the method limitations of instant claims 1-2 and 9, Huang teaches hydrogenation of carbon dioxide to formate catalyzed using Ru(II)-pincer complex 3, wherein the reaction conditions comprise the Ru(II)-pincer complex C3, KOH, hydrogen gas, and a mixture of toluene and H2O as solvent, and Huang proposes the following mechanism for the transformation (Huang; page 35; Table 4, footnotes [a] and [b]):
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One of ordinary skill in the art would recognize that the toluene/H2O reaction solvent of Huang is a two-phase system in which an organic solvent and an aqueous solvent are present in a separated state in the solvent, in a manner consistent with instant claims 1-2 and 9. Overall, the genus of formula (V) taught by Huang significantly overlaps with Formula 1 and Formula 2 of instant claims 1-2, and Huang further discloses the utility of Ru(II) as a preferred group 8 metal for the hydrogenation of carbon dioxide to form a formate or formic acid (c.f., Ru(II)-pincer complex C3 detailed above; Huang; page 35; claims 54 and 82; paragraph [016]; Table 4).
Huang fails to explicitly teach (1) a method for producing formate comprising reacting hydrogen with a hydrogen carbonate or a carbonate; (2) a species that resides within the genus of Formula 1 and Formula 3 of instant claims 1-2; and (3) a phase transfer catalyst is further used, as recited in amended claim 1.
Regarding point (1), although Huang teaches that inclusion of an organic or inorganic base, such as potassium hydroxide, in the reaction mixture also benefits the conversion (Huang; paragraph [0137] and Table 4, footnotes [a] and [b]), the method of Huang does not explicitly disclose hydrogen carbonate or a carbonate as the base additive. However, Guan teaches the conversion of CO2 into formate with hydrogen (H2) in a two-phase system (THF/H2O) using PN3P-Ru(II) pincer complexes of the following formulae, wherein complex 3 is the proposed active species and complex 2 is also active in combination with a base such as NaOH, Na2CO3, and NaHCO3 (Guan; Abstract; page 4202, Scheme 1 and Col. 2, paragraph 3; page 4203, Table 1 and Fig. 5, “Active species A”):
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Complex 3 of Guan is a species described by the genus of Huang detailed above and is structurally similar to the genus of Formula 1 of claim 1 when R0 is hydrogen; Q1 is NH, R1 is phenyl (an aryl group), A is CH, n is 3, and L represents a neutral or anionic ligand (i.e., PPh3, CO, and H). The complex of Guan differs from the claimed Formula 1 of amended claim 1 in that it does not possess a group X representing a halogen atom, and the central pyridine ring is dearomatized. Of particular note, Guan teaches that a maximum average TOF was achieved using Na2CO3 as the base and that interestingly, NaHCO3 affords moderate TOF and TON can serve as both the source of CO2 and the base (Guan; page 4202, Col. 2, paragraph 3; page 4203, Col. 1, paragraph 1; Table 1, entries 3-5). These results prompted Guan to further investigate the hydrogenation of bicarbonates (Guan; page 4203, Col. 1, paragraph 1). Thus, the teachings of Guan would indicate to the skilled artisan that hydrogen carbonate and carbonate bases are suitable alternatives to hydroxide bases for the production of formate with Ru pincer complexes, and confer advantages such as improved TOF and TON (as with Na2CO3) and the ability to serve as both the source of CO2 and the base (as with NaHCO3).
Regarding point (2), Hameed teaches a photocatalytic reduction of CO2 to formic acid with a Ru catalyst supported by N,N'-bis(diphenylphosphino)-2,6-diaminopyridine ligands (Hameed; Title; Abstract). Of particular note, Hameed discloses the preparation of Ru complexes 1+Cl- and 2+Cl- and their use in the catalytic photocatalytic reduction of CO2 to formic acid in the presence of H2, wherein the catalysts have the following structures (Hameed; page 3454; Scheme 1 and Table 1):
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The Ru complex 2+Cl- disclosed by Hameed anticipate Formula 1 and Formula 3 of instant claims 1-2 when R0 is hydrogen; Q1 is NH (as in instant claim 1), or Q2 is NH (as in instant claim 2); R1 is an aryl group (i.e., phenyl, as in instant claim 1) or R3 is an aryl group (i.e., phenyl, as in instant claim 2); A is CH; X is Cl; n is 2; and L is CO (i.e., a neutral ligand).
Regarding point (3) and further regarding claim 10, Huang and Hameed fail to teach wherein a phase transfer catalyst is further used, as recited in instant claim 1, and wherein an ammonium salt is used as a phase transfer catalyst, as recited in instant claim 10. However, Anderson teaches the exemplary use of PTC (phase-transfer catalysis) in the synthesis of ibuprofen using catalytic BnEt3NCl with KOH to avoid the use of strong bases (i.e., the PTC permits the use of KOH instead of LDA in the present example) and high-boiling water-soluble solvents (e.g., DMF and DMSO) that minimizes waste, and Anderson particularly recommends PTC when using alkali hydroxide bases (e.g., NaOH) in biphasic reaction conditions (Anderson; page 46, paragraph 1; page 47, Figure 2.18; page 61, Table 3.5; page 98, Table 4.3). In another reaction example, Anderson teaches the PTC-mediated benzylation of pyrrolidinone using (n-Bu)4NBr and K2CO3 (Anderson; page 132, Figure 5.17). Anderson further teaches that phase-transfer catalyzed reactions are often overlooked, and can provide safe, economic, and very productive alternatives to reactions using strong bases (Anderson; page 62, paragraph 1). Finally, one of ordinary skill in the art would recognize that the phase-transfer catalysts taught by Anderson (i.e., BnEt3NCl and (n-Bu)4NBr) are quaternary ammonium salts, in a manner consistent with the limitation of the instant claims 1 and 10.
The prior art as taught by Huang, Guan, and Hameed reside in the closely overlapping technical field of producing formate or formic acid by a hydrogenation reaction using ruthenium complex catalysts, in a manner consistent with the instantly claimed invention. Furthermore, the catalyst of Hameed reads directly on formula (V) of Huang and Formulae 1 and 3 of instant claims 1-2. In addition, the prior art as taught by Huang, Guan, Hameed, and Anderson reside in the overlapping technical area of synthetic organic chemistry, Huang, Guan, and Anderson teach synthetic chemistry processes in two-phase systems, and Anderson teaches that the reaction conditions taught in the method of Huang (i.e., KOH in toluene/H2O) and Guan (i.e., hydrogen carbonate and carbonate bases in THF/H2O) are particularly suited for phase transfer catalysis. Thus, the cited prior art references are from the same field of endeavor as the claimed invention and therefore deemed analogous art, as described in MPEP §2141.01(a). As such, one of ordinary skill in the art would be sufficiently motivated to incorporate the catalyst of Hameed into the method of Huang with a reasonable expectation of success. Such an endeavor would result in the simple substitution of one known element for another to obtain predictable results, as described in MPEP §2143(I)(B).
In addition, since the method of Huang teaches the use of KOH as a base in a two-phase system (Huang; Table 4, footnote [a]) and the method of Guan teaches the use of NaOH, Na2CO3, and NaHCO3 bases in a two-phase system (Guan; page 4203, Table 1), the skilled artisan could reasonably deduce from the teachings of Anderson that the incorporation of PTC in the method of Huang in view of Guan and Hameed would permit the effective use of bases weaker than KOH (e.g., Na2CO3, NHCO3 as taught by Guan) with a reasonable expectation of success. Furthermore, since Hameed teaches reaction examples in DMF solvent (Hameed; page 3454, Table 1, footnote [a]), the skilled artisan could reasonably deduce from the teachings of Anderson that the incorporation of PTC in the method of Huang in view of Huang and Hameed would permit the use of solvent other than DMF (i.e., to avoid high-boiling water-soluble solvents) with a reasonable expectation of success. Thus, the skilled artisan would be sufficiently motivated to apply the PTC conditions of Anderson to the method of Huang, Guan, and Hameed with a reasonable expectation of success, and such an endeavor would result in combining prior art elements according to known methods to yield predictable results, as described in MPEP §2143(I)(A).
Therefore, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute a hydrogen carbonate or carbonate base of Guan and the catalyst of Hameed into the method of Huang and further modify Huang to incorporate the teachings of Anderson to implement BnEt3NCl or (n-Bu)4NBr (i.e., an ammonium salt) as a phase transfer catalyst to arrive at the method of instant claims 1-2 and 9-10. The motivation to do so would permit the skilled artisan to pursue, with a reasonable expectation of success, a method that confers advantages such as improved TOF and TON (as with Na2CO3) and the ability to serve as both the source of CO2 and the base (as with NaHCO3) and avoids strong bases (i.e., using a weaker base than KOH), high-boiling water-soluble solvents, minimizes waste, and provides provide safe, economic, and very productive alternatives to reactions using strong bases, as described above.
Regarding claims 3-4 depending from claims 1-2, Hameed teaches the Ru(II) complex 2+Cl- and its use in the production of formic acid in the presence of H2, as detailed above, wherein R1 represents a phenyl group (as in instant claim 1) wherein R3 represents a phenyl group (as in instant claim 2) (Hameed; Abstract; Title; page 3454, Scheme 1 and Table 1).
Regarding claim 5 depending from claim 4, Hameed teaches the Ru(II) complex 2+Cl- and its use in the production of formic acid in the presence of H2, as detailed above, wherein the A represents CH and the Q2 represents NH (Hameed; Abstract; Title; page 3454, Scheme 1 and Table 1).
Regarding claim 6 depending from claim, Hameed teaches the Ru(II) complex 2+Cl- and its use in the production of formic acid in the presence of H2, as detailed above, wherein the R0 represents a hydrogen atom (Hameed; Abstract; Title; page 3454, Scheme 1 and Table 1).
Regarding claim 7 depending from claim 1, Hameed teaches the Ru(II) complex 2+Cl- and its use in the production of formic acid in the presence of H2, as detailed above, wherein the X represents a chlorine atom (Hameed; Abstract; Title; page 3454, Scheme 1 and Table 1).
Regarding claim 8 depending from claim 1, Hameed teaches the Ru(II) complex 2+Cl- and its use in the production of formic acid in the presence of H2, as detailed above, wherein the L each independently represents carbon monoxide (Hameed; Abstract; Title; page 3454, Scheme 1 and Table 1).
Regarding claim 11 depending from claim 1, although Huang and Hameed teach a catalyst genus or species, respectively, that comprises the ligand structure of Formula 4 of the instant claim, as detailed above, Huang and Hameed fail to teach wherein a ligand represented by Formula 4 is further added, as recited in instant claim 11.
However, Anderson teaches steps to optimizing reactions, wherein varying the reaction conditions and comparing the results to the baseline results allows the chemist to select conditions that lead to complete reactions while generating minimal impurities; Anderson further teaches that changing the proportion of reaction components, is a fundamental concept in practical chemical process optimization, as shown below (Anderson, page 169, paragraph 1 and Figure 8.5, part 1):
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Finally, Anderson teaches several conditions to vary for optimizing reactions, including catalyst, catalyst concentration, ligand, and ligand concentration (Anderson; page 169, Table 8.2):
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Thus, the teachings of Anderson would inform one of ordinary skill in the art that the reaction conditions, including the use of ligand and adjusting its concentration, are variable and amenable to optimizing. MPEP § 2144.05(II) states that “[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.”
Therefore, as with claim 1, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to combine Huang, Guan, Hameed, and Anderson and arrive at the claimed invention. The motivation to do so would achieve the predictable results of optimizing the reactions conditions through means of routine experimentation, as described above.
Regarding claim 12 depending from claim 1, Hameed teaches a proposed mechanism for catalytic reduction of CO2 to formic acid, wherein formic acid is formed during the reaction after reductive elimination of formate and protonation in situ with a H+ source (Hameed; page 3455, Scheme 2):
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Furthermore, Huang teaches a method for obtaining formate or formic acid as using a two-phase reaction system (i.e., toluene/H2O) as detailed above (Huang; claim 82; Table 4, footnotes [a] and [b]), such that the skilled artisan would recognize based on the teachings of Huang alone or Huang in view of Hameed that formate ion generated in a biphasic aqueous system would intrinsically perform the step of protonating at least a part of the formate to form formic acid by virtue of water acting as a H+ source (i.e., an equilibrium of formate and formic acid exists), in a manner consistent with the instant claim.
Based on the combined teachings of the references, the Examiner submits that a person of ordinary skill in the art would have had a reasonable expectation of success of arriving at the instantly claimed method and catalyst. Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, and absent a clear showing of evidence to the contrary.
Response to Arguments
Claim Rejections - 35 USC § 103
Applicant’s arguments filed 26 December 2025, asserting that none of the cited references discloses or suggests the claimed method for producing a formate from a hydrogen carbonate or a carbonate as recited in amended claim 1, have been fully considered but they are not persuasive in view of the new rejections for claims 1-12 that have been applied in response to a new search necessitated by Applicant’s amendments and detailed above.
MAINTAINED, MODIFIED, & NEW Double Patenting Rejections – Necessitated by Amendment
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 1-2, 9-10, and 12 remain provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 10-11, and 13-14 of copending Application No. 18/840,951.
Although the claims at issue are not identical, they are not patentably distinct from each other.
Regarding instant claims 1-2, claim 1 of copending Application No. 18/840,951 teaches a method for producing a formate through reaction between hydrogen, and a compound C including at least one selected from the group consisting of carbon dioxide, hydrogen carbonate, and carbonate in the presence of a solvent by using a metal catalyst, wherein the solvent includes an organic solvent and an aqueous solvent, a ligand is added to the solvent as necessary, the reaction between hydrogen and the compound C is performed in a two-phase system in which the organic solvent and the aqueous solvent are separate. In addition, claim 10 of copending Application No. 18/840,951 teaches the method for producing a formate according to claim 1, wherein the metal catalyst includes at least one selected from the group consisting of a ruthenium complex represented by General formula (1) indicated below, a tautomer of the ruthenium complex, a stereoisomer of the ruthenium complex, and salt compounds thereof,
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(in General formula (1), R0 represents a hydrogen atom or an alkyl group, each Q1 independently represents CH2, NH, or O, each R1 independently represents an alkyl group or an aryl group (in a case where Q1 represents NH or O, at least one R1 represents an aryl group), each A independently represents CH, CR5, or N, R5 represents an alkyl group, an aryl group, an aralkyl group, an amino group, a hydroxy group, or an alkoxy group, X represents a halogen atom, n represents 0 to 3, and in a case where the number of Ls is plural, each L independently represents a neutral or anionic ligand). Furthermore, claim 13 of copending Application No. 18/840,951 teaches wherein a phase transfer catalyst is further used in the reaction.
Thus, claims 1, 10, and 13 of copending Application No. 18/840,951 teach every limitation of instant claim 1, and every limitation of instant claim 2 when R1 is an aryl group and when Q1 independently represents NH or O.
Regarding instant claim 9, claim 11 of copending Application No. 18/840,951 teaches wherein the organic solvent includes toluene.
Regarding instant claim 10, claim 13 of copending Application No. 18/840,951 teaches wherein a quaternary ammonium salt is further used as a phase transfer catalyst in the reaction.
Regarding instant claim 12, claim 14 of copending Application No. 18/840,951 teaches protonating at least part of the formate to generate formic acid.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-2 and 10-12 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-4, 6-7, and 11 of copending Application No. 18/841,329 in view of N.G. Anderson (Practical Process & Research Development, 2000, pages 46-47, 61-62, 98, 132, 169, and 239; PTO-892 of 10-01-2025; hereinafter “Anderson”).
Although the claims at issue are not identical, they are not patentably distinct from each other.
Regarding instant claims 1-2 and 10, claims 1-2 of copending Application No. 18/841,329 teaches a catalyst reaction method using a catalyst selected from the group consisting of a metal complex represented by the general formula (1A) and (2A), a tautomer or stereoisomer of the metal complex, and a salt of the metal complex or the tautomer or stereoisomer, and claim 3 of copending Application No. 18/841,329 teaches the catalyst reaction method of claim 2, wherein the metal complex represented by the general formula (1A) is a metal complexrepresented by the following general formula (3A),
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(in the general formula (3A), R0 represents a hydrogen atom or an alkyl group, A each independently represents CH, CR5, or N, R5 represents an alkyl group, an aryl group, an aralkyl group, an amino group, a hydroxy group, or an alkoxy group, Q1 each independently represents CH2, NH, or O, CH2 and NH may further have a substituent, Y1 each independently represents a phosphorus atom or a nitrogen atom, R each independently represents an alkyl group, an aryl group, or an aralkyl group, which may further have a substituent, M represents a metal atom, Z represents a halogen atom or a hydrogen atom, n represents an integer of 0 to 3, and when more than one L are present, L each independently represents a neutral or anionic ligand). In addition, claim 4 of copending Application No. 18/841,329 teaches wherein the metal atom represented by M is ruthenium. Furthermore, claim 6 of copending Application No. 18/841,329 teaches wherein the catalyst reaction is a formate forming reaction, and claim 7 of copending Application No. 18/841,329 teaches the catalyst reaction method according to claim 6, wherein the formate forming reaction is a method for producing a formate by allowing hydrogen to react with at least one compound selected from the group consisting of carbon dioxide, a hydrogen carbonate, and a carbonate in the presence of a solvent, and the formate forming reaction is a two-phase system reaction in which an organic solvent and an aqueous solvent are present in a separated state in the solvent.
Overall, claim 1-4 and 6-7 teach every claim limitation of Formula 1 of instant claim 1 when Y1 represents a phosphorous atom, M is ruthenium, Z is a halogen atom, and R represents an alkyl group or an aryl group (provided that when Q1 represents NH or O, at least one of R represents an aryl group) in the catalyst of general formula (3A). In addition, the copending claims teach the catalyst of Formula 3 of instant claim 2 when Q1 is NH or O, Y1 represents a phosphorous atom, M is ruthenium, Z is a halogen atom, and R represents an aryl group in the catalyst of general formula (3A).
Claims 1-4 and 6-7 of copending Application No. 18/841,329 fails to teach that a phase transfer catalyst is further used, as recited in amended claim 1, and wherein an ammonium salt is used as the phase transfer catalyst, as recited in instant claim 10.
This deficiency is remedied by Anderson, who teaches the following.
Anderson teaches the exemplary use of PTC (phase-transfer catalysis) in the synthesis of ibuprofen using catalytic BnEt3NCl with KOH to avoid the use of strong bases (i.e., the PTC permits the use of KOH instead of LDA in the present example) and high-boiling water-soluble solvents (e.g., DMF and DMSO) that minimizes waste, and Anderson particularly recommends PTC when using alkali hydroxide bases (e.g., NaOH) in biphasic reaction conditions (Anderson; page 46, paragraph 1; page 47, Figure 2.18; page 61, Table 3.5; page 98, Table 4.3). In another reaction example, Anderson teaches the PTC-mediated benzylation of pyrrolidinone using (n-Bu)4NBr and K2CO3 (Anderson; page 132, Figure 5.17). Anderson further teaches that phase-transfer catalyzed reactions are often overlooked, and can provide safe, economic, and very productive alternatives to reactions using strong bases (Anderson; page 62, paragraph 1). Finally, one of ordinary skill in the art would recognize that the phase-transfer catalysts taught by Anderson (i.e., BnEt3NCl and (n-Bu)4NBr) are quaternary ammonium salts, in a manner consistent with the limitation of the instant claims 1 and 10.
The prior art as by copending Application No. 18/841,329 and Anderson reside in the overlapping technical area of synthetic organic chemistry and chemistry processes in two-phase systems. Thus, the cited prior art are from the same field of endeavor as the claimed invention and therefore deemed analogous art, as described in MPEP §2141.01(a). Thus, the skilled artisan would be sufficiently motivated to apply the PTC conditions of Anderson to the method of copending Application No. 18/841,329 with a reasonable expectation of success, and such an endeavor would result in combining prior art elements according to known methods to yield predictable results, as described in MPEP §2143(I)(A).
Therefore, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the method of copending Application No. 18/841,329 to incorporate the teachings of Anderson to implement BnEt3NCl or (n-Bu)4NBr (i.e., an ammonium salt) as a phase transfer catalyst to arrive at the method of instant claims 1-2 and 9-10. The motivation to do so would permit the skilled artisan to pursue, with a reasonable expectation of success, a method that avoids strong bases (i.e., using a weaker base than KOH), high-boiling water-soluble solvents, minimizes waste, and provides provide safe, economic, and very productive alternatives to reactions using strong bases, as described above.
Regarding instant claim 11, Anderson teaches steps to optimizing reactions, wherein varying the reaction conditions and comparing the results to the baseline results allows the chemist to select conditions that lead to complete reactions while generating minimal impurities; Anderson further teaches that changing the proportion of reaction components, is a fundamental concept in practical chemical process optimization, as shown below (Anderson, page 169, paragraph 1 and Figure 8.5, part 1):
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Finally, Anderson teaches several conditions to vary for optimizing reactions, including catalyst, catalyst concentration, ligand, and ligand concentration (Anderson; page 169, Table 8.2):
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Thus, the teachings of Anderson would inform one of ordinary skill in the art that the reaction conditions, including the use of ligand and adjusting its concentration, are variable and amenable to optimizing. MPEP § 2144.05(II) states that “[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.”
Therefore, as with claim 1, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to combine Claims 1-4 and 6-7 of copending Application No. 18/841,329 and Anderson to arrive at the claimed invention. The motivation to do so would achieve the predictable results of optimizing the reactions conditions through means of routine experimentation, as described above.
Regarding instant claim 12, claim 11 of copending Application No. 18/841,329 teaches a first step of producing a formate by the catalyst reaction method according to claim 7; and a second step of protonating at least a part of the formate to form formic acid.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-2 and 9-12 remain provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 4-8 of copending Application No. 18/043,973.
Although the claims at issue are not identical, they are not patentably distinct from each other.
Regarding instant claims 1-2, claim 1 of copending Application No. 18/043,973 teaches a method for producing a formate, the method comprising: a first step of reacting hydrogen with carbon dioxide, a hydrogen carbonate or a carbonate using a catalyst in the presence of a solvent to form the formate in a reaction liquid, wherein the reaction is a two-phase system in which an organic solvent and an aqueous solvent are present in a separated state in the solvent. In addition, claim 4 of copending Application No. 18/043,973 teaches wherein the catalyst is at least one selected from a ruthenium complex represented by the following formula (1), a tautomer or stereoisomer thereof, and a salt compound of the complex, tautomer or stereoisomer:
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wherein R0 represents a hydrogen atom or an alkyl group, Q1 each independently represents CH2, NH or O, R1 each independently represents an alkyl group or an aryl group (provided that when Qi represents NH or O, at least one of R1 represents an aryl group), A each independently represents CH, CR5 or N, R5 represents an alkyl group, an aryl group, an aralkyl group, an amino group, a hydroxy group or an alkoxy group, X represents a halogen atom, n represents 0 to 3, and when more than one L are present, L each independently represents a neutral or anionic ligand. Thus, claims 1 and 4 of copending Application No. 18/043,973 teach every limitation of instant claim 1, and every limitation of instant claim 2 when R1 is an aryl group and when Q1 independently represents NH or O. In addition, claim 7 of copending Application No. 18/043,973 teaches wherein a phase transfer catalyst is further used.
Thus, claims 1, 4, and 7 of copending Application No. 18/043,973 teaches every limitation of instant claims 1-2.
Regarding instant claim 9, claim 6 of copending Application No. 18/043,973 teaches wherein the organic phase contains toluene or dioxane.
Regarding instant claim 10, claim 7 of copending Application No. 18/043,973 teaches wherein a quaternary ammonium salt is used as a phase transfer catalyst.
Regarding instant claim 11, claim 5 of copending Application No. 18/043,973 teaches wherein a ligand represented by the following formula (4) is further added:
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wherein R0 represents a hydrogen atom or an alkyl group, Q2 each independently represents NH or O, R3 each independently represents an aryl group, A each independently represents CH, CR5 or N, and R5 represents an alkyl group, an aryl group, an aralkyl group, an amino group, a hydroxy group or an alkoxy group.
Regarding instant claim 12, claim 8 of copending Application No. 18/043,973 teaches a second step of protonating at least a part of the formate by electrodialysis to form formic acid and water.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
It is further noted that the claims of copending Application No. 18/043,973 have been indicated as being allowable in the NOA dated 1/2/2026.
Claims 1-2 and 9-11 remain provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 5, 7-9 of copending Application No. 18/043,928.
Although the claims at issue are not identical, they are not patentably distinct from each other.
Regarding instant claims 1-2, claim 1 of copending Application No. 18/043,928 teaches a method for producing an alkaline earth metal formate, the method comprising: a first step of reacting hydrogen and carbon dioxide with a carbonate or hydrogen carbonate of an alkaline earth metal using a homogeneous catalyst in the presence of a solvent in a two-phase system in which an organic phase and an aqueous phase are present in a separated state in the solvent to produce a formate of an alkaline earth metal. In addition, claim 7 of copending Application No. 18/043,928 teaches wherein the homogeneous catalyst is at least one selected from a ruthenium complex represented by the following formula (1), a tautomer or stereoisomer thereof, and a salt compound of the complex, tautomer or stereoisomer:
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wherein R0 represents a hydrogen atom or an alkyl group, Q1 each independently represents CH2, NH or O, R1 each independently represents an alkyl group or an aryl group (provided that when Qi represents NH or O, at least one of R1 represents an aryl group), A each independently represents CH, CR5 or N, R5 represents an alkyl group, an aryl group, an aralkyl group, an amino group, a hydroxy group or an alkoxy group, X represents a halogen atom, n represents 0 to 3, and when more than one L are present, L each independently represents a neutral or anionic ligand. Thus, claims 1 and 7 of copending Application No. 18/043,928 teach every limitation of Formula 1 of instant claim 1, and every limitation of Formula 3 of instant claim 2 when R1 is an aryl group and when Q1 independently represents NH or O. Furthermore, claim 7 of copending Application No. 18/043,928 teaches every limitation of instant claim 13, and every limitation of instant claim 14 when R1 is an aryl group and when Q1 independently represents NH or O, respectively. Finally, claim 9 of copending Application No. 18/043,928 teaches wherein a phase transfer catalyst is further used.
Thus, claims 1, 7, 9, and 13 of copending Application No. 18/043,928 teaches every limitation of instant claims 1-2.
Regarding instant claim 9, claim 5 of copending Application No. 18/043,928 teaches wherein the organic phase contains at least one selected from toluene, dioxane, tetrahydrofuran, ethyl acetate, methylcyclohexane, and cyclopentyl methyl ether.
Regarding instant claim 10, claim 9 of copending Application No. 18/043,928 teaches wherein a quaternary ammonium salt is further used as a phase transfer catalyst in the first step.
Regarding instant claim 11, claim 8 of copending Application No. 18/043,928 teaches wherein a ligand represented by the following formula (4) is further added:
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wherein R0 represents a hydrogen atom or an alkyl group, Q2 each independently represents NH or O, R3 each independently represents an aryl group, A each independently represents CH, CR5 or N, and R5 represents an alkyl group, an aryl group, an aralkyl group, an amino group, a hydroxy group or an alkoxy group.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Response to Arguments
Claim Rejections – Double Patenting
Applicant’s arguments filed 26 December 2025, asserting that the subject matter presently recited in the instant claims is not addressed by the provisional double patenting rejections, have been fully considered but they are not persuasive.
As detailed above and in response to Applicant’s amendments filed 26 December 2025, the provisional nonstatutory double patenting rejections were maintained and modified for the claims of ‘951, ‘973, and ‘928. In addition, regarding the claims of ‘329, new provisional nonstatutory double patenting rejections were applied, wherein claims 1-2 and 10-12 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-4, 6-7, and 11 of copending Application No. 18/841,329 in view of Anderson.
Conclusion
No claims are allowed.
Applicant’s amendment under 37 CFR 1.97(c) with the fee set forth in 37 CFR 1.17(p) on 26 December 2025 necessitated and prompted the maintained and modified 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 extension fee 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.
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/D.R./Examiner, Art Unit 1692
/AMY C BONAPARTE/Primary Examiner, Art Unit 1692