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 8-17 are pending.
Claims 14-16 have been amended.
Thus, claims 8-17 represent all claims currently under consideration.
Claim Interpretation
Claim 8 recites five process steps a) through e). For the purposes of examination, claim 8 will be interpreted in a manner consistent with the written description (Specification; page 5, lines 14 and 16-17), such that process steps a), b), c), and d) can be effected in any desired sequence, steps d) and e) can be effected simultaneously or successively, and CO can be fed in two or more steps.
REJECTIONS WITHDRAWN
The status for each rejection and/or objection in the previous Office Action is set out below.
Claim Objections
Applicant’s amendments filed 7/15/2026 have fully overcome the objections to claims 14-16.
35 U.S.C. § 103
Applicant’s remarks filed 7/15/2026, wherein on p. 6-9 of the response Applicant argues that the position taken by the Office Action dated 5/18/2026 conflicts with the Office position taken in the grant of US 11,712,688 (parent application) that claims a complex comprising Pt and the structure of ligand L12. Claim 17 is directed to the use of the platinum complex, which includes the L12 ligand. Applicant further argues that the instant specification, which is identical to that of the parent (‘688 patent), illustrates the superiority of the platinum complexes containing the platinum L12 ligand – high yield and selectivity. The use of platinum complex associated with L12 (the patented complex) is reported as resulting in 95% (n/iso = 73/27) and in platinum complexes for L14 and L15 of 54% (n/iso = 73/27) and 24% (n/iso = 77/23), respectively (Specification; page 8, Scheme depicting bidentate phosphine ligands).
Applicant further argues that the catalysis involved with the claimed chemical reaction has a high degree of unpredictability. As such, Dong teaches a complex containing palladium and does not teach a complex containing platinum. Equivalency of platinum and palladium for the claimed method represents an uncertain outcome.
These arguments have been fully considered and are persuasive to overcome the rejections of claims 16-17 under 35 U.S.C. 103 as being unpatentable over Suykerbuyk et al. (WO 98/42717 A1; published 10-01-1998; PTO-892 of 10-02-2025), in view of M. P. Saefong (Market Watch article, pages 1-4; published 02-21-2020; PTO-892 of 10-02-2025), Clark et al. (US 2016/0184811 A1; published 06-30-2016; PTO-892 of 10-02-2025) and Dong et al. (US 2017/0022137 A1; published 08-08-2017; PTO-892 of 05-18-2026) on record of the Office Action dated 5/18/2026. Neither Suykerbuyk nor Suykerbuyk in view of Saefong, Clark, or Dong would sufficiently motivate the skilled artisan to arrive at the process according to claim 8, where R2 and R4 are –(C1-C12)-alkyl or where the compound of formula (I) has formula (1), as recited in claims 16-17, with a reasonable expectation of success. Therefore, the rejections are withdrawn.
NEW Claim Objections
Claims 16-17 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
MAINTAINED Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office Action.
Claims 8-15 are rejected under 35 U.S.C. 103 as being unpatentable over Suykerbuyk et al. (WO 98/42717 A1; published 10-01-1998; PTO-892 of 10-02-2025), in view of M. P. Saefong (Market Watch article, pages 1-4; published 02-21-2020; PTO-892 of 10-02-2025) and Clark et al. (US 2016/0184811 A1; published 06-30-2016; PTO-892 of 10-02-2025).
Regarding claim 8, Suykerbuyk diphosphine ligands for carbonylation catalysts obtainable by combining: (i) a metal cation selected from the groups (8, 9, or 10) of the Periodic Table of Elements; and (ii) the new diphosphine; and furthermore to a process for carbonylating unsaturated compounds in the presence of the carbonylation catalyst (Suykerbuyk; Abtract; claims 1 and 9). Suykerbuyk further teaches that the invention relates to novel disphosphines, novel carbonylation catalysts and a process for the carbonylation of unsaturated compounds by reaction thereof with carbon monoxide and a coreactant in the presence of the novel carbonylation catalysts, wherein the metal cation of the carbonylation catalyst is preferably Rh, Pd, or Pt; wherein the unsaturated compound is an ethylenically unsaturated compound of 2 to 30 carbon atoms per molecule; wherein the ethylenically unsaturated compound is an alpha- or internal olefin having from 2 to 22 carbon atoms per molecule, or a cycloalkadiene; and wherein the coreactant is molecular hydrogen, monohydric alcohols have from 1 to 6 carbon atoms per molecule, dihydric alcohols have from 2 to 6 carbon atoms per molecule, and alkylphenols (Suykerbuyk; claims 10-14). In one embodiment, Suykerbuyk teaches a carbonylation reaction wherein the autoclave was charged with 50 mL of methanol, 0.1 mmol of palladium(II) acetate, 0.15 mmol of 1,3-P,P'-di(2-phospha-l,3,5,7-tetramethyl-6,9,10-trioxatricyclo [3.3.1.1{3.7}decyl)propan (DPA3, a diphosphine ligand), and 0.2 mmol of methanesulphonic acid (MSA); after being flushed, the autoclave was pressurised with carbon monoxide and ethene to a partial pressure of 30 bar and 20 bar respectively; next, the reactor was sealed; the contents of the autoclave were heated to a temperature of 90 °C and maintained at that temperature for 0.25 hours; after cooling, a sample was taken from the contents of the autoclave and analysed by Gas Liquid Chromatography; ethene was fully converted with 100% selectivity into methyl propanoate at an average rate of 8000 mole per mole Pd per hour (mol/mol•hr) (Suykerbuyk; page 10, Example 2). Of particular note, Suykerbuyk teaches an embodiment wherein Example 2 was repeated, however using 0.1 mmol of platinum(II) acetylacetonate, 0.12 mmol of DPA3 (i.e., a diphosphine ligand), and 0.25 mmol of MSA; besides, the contents of the autoclave were heated to 125 °C; the autoclave was cooled after 3 hours; ethene was fully converted with 100% selectivity into methyl propionate at an average rate of 500 mol/mol•hr. (Suykerbuyk; page 11, Example 8).
Overall, the teachings of Suykerbuyk explicitly suggests that Pt and Pd are equivalents in the reaction (Suykerbuyk; claims 10-14; Examples 2 and 8). Furthermore, one of ordinary skill in the art could reasonably prefer to use Pt in the method of Suykerbuyk rather than Rh or Pd due to its drastically lower cost, as evidenced by Saefong, who teaches that (as of late February 2020) the most-active March futures contract for palladium settled at a record $2,605.40 an ounce (highest since November 1984), platinum settled at $976.10, and rhodium also increased to $12,700 an ounce; Saefong further teaches that given the price differences between the metals, talk of a switch to the use of platinum, instead of palladium, for catalytic converters in motor vehicles, which help control exhaust emissions, has grown (Saefong; page 2, paragraphs 2-4).
Suykerbuyk fails to teach adding a compound having formula (I), as recited in instant claim 8, but otherwise teaches every limitation of the instant claim. However, Clark teaches aryl phosphines with fused ring ortho-alkoxy substitution as ligands for a variety of transition metals, including, but not but not limited to titanium (Ti), copper (Cu), palladium (Pd), cobalt (Co), rhodium (Rh), ruthenium (Ru), chromium (Cr) and platinum (Pt); these ligands include a P atom covalently bonded to an aryl ring for a variety of transition metal catalyzed reactions, including methoxycarbonylation of olefins, which is analogous to the reaction of Suykerbuyk, wherein the alcohol is methanol (Clark; Abstract; paragraph [0002]). In addition, Clark teaches that the present disclosure provides for the surprising discovery that an aryl phosphine with a fused ring ortho-alkoxy substitution allows for an electronic benefit associated with the ortho-alkoxy group (e.g., electron donating group) while reducing steric bulk around the catalyst compared to an alkoxy group lacking a fused ring, enabling increased performance of catalysts containing this aryl phosphine as a ligand; increased performance can refer to higher rate of reaction, higher conversion of reagents, increased catalyst turnover number, longer catalyst lifetime, and/or improved selectivity for a desired product relative to side products (Clark; paragraph [0004]). Of particular note, Clark teaches ligand (LXXV) for use in methoxycarbonylation and/or hydroformylation (Clark; paragraph [0023]):
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This compound reads directly on formula (I) of the instant claim when R1-R4 is a C8-heteroaryl radical having at least six ring atoms.
The prior art as taught by Suykerbuyk and Clark reside in the closely overlapping technical field of transition metal complexes comprising diphosphines and platinum for application as catalysts in alkoxycarbonylation/methoxycarbonylation reactions, in a manner consistent with the instant claim, such that the skilled artisan would be sufficiently motivated to incorporate the ligand of Clark to the method of Suykerbuyk to arrive at a predictably functional alkoxycarbonylation catalyst with a reasonable expectation of success. Furthermore, the evidentiary teaching of Saefong would inform the skilled artisan that employing Pt as the active metal species in the method of Suykerbuyk would be economically advantageous due to its significantly lower cost as compared with Pd and Rh, respectively, and the method of Suykerbuyk teaches that Pd, Pt, and Rh are functionally equivalent at performing the claimed process. 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 have modified Suykerbuyk to incorporate the teachings of Clark to implement the use of diphosphine ligand (LXXV) in the method of Suykerbuyk with the preferential use of less expensive Pt metal, as evidenced by Saefong. There is a reasonable expectation of success that the catalyst will work in the reaction of Suykerbuyk because replacing one known phosphine catalyst for another known to work in the same reaction is predictable and prima facie obvious. MPEP § 2143(I)(B). Further, as Clark teaches that the disclosed catalysts have improved activity in the reaction, the skilled artisan would be further motivated to replace the catalyst of Clark with that of Suykerbuyk in order to impart those advantages to the process of Suykerbuyk.
Regarding claim 9 depending from claim 8, Suykerbuyk teaches wherein the ethylenically unsaturated compound is ethene (Suykerbuyk; pages 10-11, Examples 2 and 8).
Regarding claims 10-11 depending from claim 8, Suykerbuyk teaches wherein the alcohol is methanol (Suykerbuyk; pages 10-11, Examples 2 and 8).
Regarding claims 12-13 depending from claim 8, Suykerbuyk teaches wherein the substance comprising Pt is platinum(II) acetylacetonate (Suykerbuyk; page 11, Example 8).
Regarding claims 14-15 depending from claim 8, Clark teaches ligand (LXXV) for use in methoxycarbonylation and/or hydroformylation, as detailed above (Clark; paragraph [0023]). The ligand of Clark comprises -(C6-C20)-heteroaryl groups having at least six ring atoms and are benzofuranyl groups, in a manner consistent with the instant claims.
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. 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 7/15/2026, asserting that the teachings of Suykerbuyk, Saefong, Clark, and Dong would not sufficiently motivate the skilled artisan to arrive at the platinum complex containing the L12 ligand has been fully considered and was found to be persuasive.
Applicant’s arguments further asserting that all stated grounds of the rejection have been properly traversed, accommodated, or rendered moot have been fully considered, but are not found to be persuasive.
Applicant refers platinum complexes L12-L16, and argues the following:
“The Examiners' position has been considered.
Clarification is requested. The position taken here conflicts with the Office position taken in the grant of US 11,712,688 (parent application). Claim 17 is directed to the use of the platinum complex, which includes the L12 ligand.
The instant specification, which is identical to that of the parent (the '688 patent). Presented in the specification are results illustrating the superiority of the platinum complexes containing the platinum L12 ligand - high yield and product selectivity.
The comparisons provided in the specification reflect a wide range of ligand types. All include platinum. The range of results ranges from inactive to active. The reported ligand structures are varied.
Of these, the use of platinum complex associated with L12 (the patented complex) is reported as resulting 95% (n/iso = 73/27) and in platinum complexes for L14 and L15 54% (n/iso = 73/27) and 24% (n/iso = 77/23), respectively. The n/iso ratio shows a predominantly linear product…
…The structural effects of the phenyl, the hetero group and t-butyl group are clear - a linear product in high yields. The yield reported for the use of the platinum complex L12. increase is significant, almost a twofold increase.
The teachings of Suykerbuyk et al., M. P. Saefong and Clark et al. have been considered. The overall characterization of each of the references is accurate. The technology represented illustrates a technical area which is not in its infancy. Many reactions are known. What is at issue is a path that would lead one a particular product in high yield. The product is selectively produced. Catalysis like chemistry has a high degree of unpredictability.
The platinum complex containing the L12 ligand requires a suggestion of a design that would lead one with a reasonable expectation of increased yields and product selectivity. Hindsight makes an invention to appear simpler than it is. At issue, is a process that results in a product selectively and in high yield. The Dong et al, relied upon below, is not relied upon here. It teaches selectivity and a ligand that might be responsible. Dong et al. is not a teaching the complex at issue here. It contains palladium. Equivalency of platinum and palladium for the purpose here is not taught by Dong et al. In hindsight, it is easily said that it would be possible to try. The outcome is not a certainty. A teaching is missing. Reconsideration is respectfully requested…
…The relevancy the teachings of Dong et al. is discussed above. There is no teaching in Dong et al. of equivalency of palladium and platinum in the context of their invention. Selectivity improvements are mentioned by Dong et al. for their palladium complex.
Claim 17 is limited to platinum complexes containing L12. Claims 14-16 increasing narrow the scope of the ligand. The examiner recognizes that platinum complex having L12 is not taught. The use of this complex has been shown to increase yields and selectivity. This is shown for the platinum complex. For L12, the results are unexpected. The Office recognizes this by the patent grant.
Applicant submits the Office has not addressed the result support issue. Evidence has not been provided as to why the results do not support a rebuttal of the prima facie obviousness as to one or more of claims 14-16.
Reconsideration is respectfully requested.”
These arguments have been fully considered and are found to be persuasive. Upon consideration of Applicant’s arguments, the 103 rejections of claims 16-17 on record of the Office Action dated 5/18/2026 have been withdrawn. Neither Suykerbuyk nor Suykerbuyk in view of Saefong, Clark, or Dong would sufficiently motivate the skilled artisan to arrive at the process according to claim 8, where R2 and R4 are –(C1-C12)-alkyl or where the compound of formula (I) has formula (1), as recited in claims 16-17, with a reasonable expectation of success. Therefore, the rejections are withdrawn.
Applicant argues the following:
“All of the stated grounds of rejection have been properly traversed, accommodated, or rendered moot. Therefore, it is respectfully requested that the Examiner reconsider all presently outstanding rejections and that they be withdrawn. It is believed that a full and complete response has been made to the outstanding Official Action and, as such, the present application is in condition for allowance.”
This argument has been fully considered but is not found to be persuasive. Although Applicant’s arguments were found to be persuasive regarding the 103 rejections of claims 16-17 of the previous Office Action dated 5/18/2026, the unexpected results of ligand L12 is not commensurate in scope with respect to the broader structural genus recited in claims 8 and 14-15. See MPEP § 2145.
Furthermore, the ligand (LXXV) of Clark for use in methoxycarbonylation and/or hydroformylation with metals including Pt resides within the claimed genus of claim 8 and subgenera of claims 14-15, respectively (Abstract; 0002 and 0023). Since Suykerbuyk teaches the process limitations of claims 8-13 and both Suykerbuyk and Clark teach analogous methods for Pt-catalyzed methoxycarbonylation with diphosphine ligands, it would have been prima facie obvious to substitute the ligand of Suykerbuyk with that of Clark to arrive at the invention of claims 8-15 with a reasonable expectation of success. Therefore, the rejections of claims 8-15 are maintained for the reasons of record and the reasons set forth above.
Subject Matter Free From the Prior Art
Claims 16-17 appear to be free from the prior art and could be allowable if rewritten or amended to overcome the objections to claim 16-17 set forth in this Office Action.
The following is a statement of reasons for the indication of allowable subject matter:
The prior art of record does not teach or suggest the process according to claim 8, where R2 and R4 are –(C1-C12)-alkyl or where the compound of formula (I) has formula (1):
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as recited in claims 16-17,
Exemplary prior art includes:
Suykerbuyk et al. (WO 98/42717 A1; published 10-01-1998; PTO-892 of 10-02-2025), who teaches diphosphine ligands for carbonylation catalysts and a process for the carbonylation of unsaturated compounds by reaction thereof with carbon monoxide and a coreactant in the presence of the novel carbonylation catalysts, wherein the metal cation of the carbonylation catalyst is preferably Rh, Pd, or Pt; wherein the unsaturated compound is an ethylenically unsaturated compound of 2 to 30 carbon atoms per molecule, and wherein the coreactant is molecular hydrogen, monohydric alcohols have from 1 to 6 carbon atoms per molecule, dihydric alcohols have from 2 to 6 carbon atoms per molecule, and alkylphenols. Example 2 of Suykerbuyk teaches a carbonylation reaction comprising methanol, CO, ethene, palladium(II) acetate, and 1,3-P,P'-di(2-phospha-l,3,5,7-tetramethyl-6,9,10-trioxatricyclo [3.3.1.1{3.7}decyl)propan (DPA3, a diphosphine ligand) (Abstract; claims 1 and 9-14; page 10, Example 2).
Suykerbuyk does not teach or suggest a platinum complex with a ligand of the genus of formula (I) where R2 and R4 are –(C1-C12)-alkyl, or where the compound of formula (I) has formula (1), as recited in claims 16-17.
Clark et al. (US 2016/0184811 A1; published 06-30-2016; PTO-892 of 10-02-2025), who teaches aryl phosphines with fused ring ortho-alkoxy substitution as ligands for a variety of transition metals, including platinum (Pt). These ligands include a P atom covalently bonded to an aryl ring for a variety of transition metal catalyzed reactions, including methoxycarbonylation of olefins wherein the alcohol is methanol. Clark further teaches ligand (LXXV) for use in methoxycarbonylation and/or hydroformylation (Abstract; 0002 and 0023):
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Although Clark teaches phosphine ligands that include a t-butyl group (i.e., a -(C4)-alkyl group; Clark; paragraph [0025], Formula (LXXX)), Clark does not explicitly teach or suggest a compound of formula (I) wherein R2 and R4 are -(C1-C12)-alkyl, as recited in instant claim 16, or the compound of formula (1) as recited in instant claim 17.
Dong et al. (US 2017/0022137 A1; published 08-08-2017; PTO-892 of 05-18-2026), who teaches teaches benzene-based diphosphine ligands, metal complexes of these compounds and to the use thereof for alkoxycarbonylation of ethylenically unsaturated compounds. Dong further teaches formulae (1) and (18) of the following structures and their complexes comprising Pd as catalysts for alkoxycarbonylation:
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Dong further teaches that the ligands of the present invention provide higher yields of esters and are suitable for the alkoxycarbonylation of long-chain ethylenically unsaturated compounds, for example C8 olefins, and of mixtures of ethylenically unsaturated compounds, and the presence of functional groups is also tolerated. In addition, Dong teaches that the ligands according to the invention improve the n/iso selectivity of the alkoxycarbonylation (Title; 0001-0002, 0005-0006, 0052-0053; claims 8 and 12)
While formula (1) of Dong is structurally similar to the genus of claim 16 and formula (1) of instant claim 17, it differs in that Dong teaches a 1,2-disubsituted benzene comprising the bis-benzylphosphorus ligands, whereas the genus of instant claim 16 and formula (1) of instant claim 17 comprises a 1,3-disubstituted benzene nucleus with otherwise identical substituents. Furthermore, Dong is directed towards complexes of Pd, and Dong does not teach or suggest the use of Pt as recited in the instant claims.
Although Suykerbuyk, Clark, and Dong teach the use of phosphine ligands for carbonylation reactions, none of the cited prior art, alone or in combination, teach each and every element of instant claims 16-17. Furthermore, the skilled artisan would not be sufficiently motivated to modify or combine the cited prior art to arrive a compound comprising the genus of claim 16 or formula (1) of claim 17 with a reasonable expectation of success. Therefore, the claims are free from the prior art for the reasons of record and the reasons set forth above.
Conclusion
The prior art made of record and not relied upon is considered pertinent to Applicant’s disclosure.
Applicant’s amendment under 37 CFR 1.97(c) with the fee set forth in 37 CFR 1.17(p) on 7/15/2026 necessitated and prompted the maintained 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.
Any inquiry concerning this communication or earlier communications from the Examiner should be directed to Derek Rhoades whose telephone number is (703)-756-5321. The Examiner can normally be reached Monday–Thursday, 7:30 am-5:00 pm EST; Friday, 7:30 am-4:00 pm EST.
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/D.R./Examiner, Art Unit 1692
/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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