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 .
Response to Amendment
The amendment filed on 06/22/2026 has been entered. Claims 1-11 are pending in the application. Applicant’s amendments to the claims have not introduced new matter and are supported in the specification in at least the claims filed 06/26/2023.
Applicant’s amendments to the claims have overcome each and every Claim Objection previously set forth in the office action mailed 03/20/2026.
Response to Arguments
Applicant's arguments filed 06/22/2026 have been fully considered but they are not persuasive.
Applicant argues on Pg. 8-9 that Hattori is cited only for the process and the catalyst claim element Hattori is relied on is inaccurate. Applicant argues Hattori is relied on to teach the platinum group metal ion-supported catalyst according to claim 1. Applicant argues Hattori uses Pd/C metal nanoparticles on carbon but neither ions/complexes nor an ion exchanger.
However, in response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
Hattori is not relied on to teach the limitations according to claim 1 (i.e. “a platinum group metal ion-supported catalyst” and that “the platinum group metal ion-supported catalyst is a platinum group metal ion-supported catalyst in which platinum group metal ions or platinum group metal complex ions are supported on a non- particulate organic porous ion exchanger, wherein the non-particulate organic porous ion exchanger is formed of a continuous framework phase and a continuous pore phase; has a thickness of a continuous framework of 1 to 100 4m, an average diameter of continuous pores of 1 to 1000 pm, and a total pore volume of 0.5 to 50 ml/g; has an ion exchange capacity per weight in a dry state of 1 to 9 mg equivalent/g; and has ion exchange groups wherein the ion exchange groups are uniformly distributed in the organic porous ion exchanger,”) nor is Hattori relied on to teach “platinum group metal ions or platinum group metal complexes” are supported on the support.
Each of these limitations is taught by Takada and Trejo O’Reilly, respectively, as presented in the non-final rejection of 03/20/2026 and again in the 103 rejection below.
Applicant argues on Pg. 10 Takada is not merely silent regarding ions or complexes explicitly being on the support, but rather that the inventive concept of Takada is the reduction of metal nanoparticles formed by adsorbed ions. Applicant argues keeping the adsorbed ions without reducing them to nanoparticles would contradict Takada’s teaching.
However, Takada is not relied on to teach the metal ions on the support, but rather Trejo O’Reilly is. Trejo O’Reilly teaches a heterogenous catalyst for performing carbon-carbon bond forming reactions where the heterogenous catalyst includes a palladium loaded cationic exchange resin where the palladium can be loaded as an ion ([0011]). Advantageously, supports loaded with ionic palladium provides catalysts with higher efficiency compared with supported palladium catalysts produced otherwise, while also displaying higher thermal stability ([0003]).
Applicant argues on Pg. 10 Trejo O’Reilly teaches a core catalyst supported on macroreticular beads and not monoliths. Applicant argues the rejection does not explain why a skilled artisan would apply ionic Pd to a monolith rather than the bead architecture taught in Trejo O’Reilly.
However, in response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). Trejo O’Reilly is not relied on to teach the monolithic support but rather Takada is. Advantageously, the supported catalyst taught by Takada displays high activity in carbon-carbon bond forming reactions and allows for efficient reactions (Pg. 2, Description, par. 6-7).
Furthermore, in response to applicant's argument that the ionic Pd would not be incorporated into a monolithic support, such as that taught by Takada, the test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981). Trejo O’Reilly teaches independently that supports loaded with ionic palladium provides catalysts with higher efficiency compared with supported palladium catalysts produced otherwise, while also displaying higher thermal stability ([0003]).
Applicant argues Trejo O’Reilly teaches a methanol/toluene solvent while Hattori uses an aqueous EtOH solution. Applicant argues this incompatibility was not addressed.
However, Examiner notes claim 10 uses water or a hydrophilic solvent while claim 11 uses hydrophobic solvent. These solvents encompass essentially all solvents known to skilled artisans and arguments regarding the nature of the solvent would require factual support or showings of criticality. Further, the test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981). Trejo O’Reilly teaches independently that supports loaded with ionic palladium provides catalysts with higher efficiency compared with supported palladium catalysts produced otherwise, while also displaying higher thermal stability ([0003]).
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C.
102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the
statutory basis 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.
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 8-10 are rejected under 35 U.S.C. 103 as being unpatentable over Hattori et al. (Catalysts 2015, 5, 18-25) in view of Takada et al. (JP2014015420A; cited in IDS dated 06/26/2023) and Trejo O Reilly et al. (US20150353445A1). Note, the English translation of Takada cited below is provided by the Examiner, as the copy provided by Applicant only has an English abstract.
Regarding claim 8, Hattori teaches a method for performing Suzuki-Miyaura Coupling reactions in a continuous flow system with a palladium on carbon supported catalyst (Title). Hattori teaches the Suzuki-Miyaura Coupling reaction is a reaction between aryl halides and arylboronic acids that forms carbon-carbon bonds in the presence of sodium carbonate (Na2CO3) base and EtOH/H2O solvent mixtures (Pg. 18-19, Introduction; Table 1). Hattori teaches the arylboronic acids are organic compounds (see Pg. 20) and accordingly the combination of aryl halide and arylboronic acid taught by Hattori meet the claimed option of “(1) reaction of an aromatic halide with an organoboron compound”. Additionally, this mixture meets the limitations of “a raw material liquid (i) containing the aromatic halide and the organoboron compound”.
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Hattori teaches the reaction is performed by preparing a solution of Na2CO3 in water, mixing with an aryl halide, then mixing with an EtOH solution of arylboronic acid prior to passing the solution through a catalyst-packed cartridge, where the catalyst contains Pd supported on carbon, and collecting the reaction solution exiting the catalyst-packed cartridge (i.e. Pd/C) (Pg. 22, 3.2). A catalyst-packed cartridge that is fed an initial solution and that has a reaction solution exit necessitates an “introduction path” and a “discharge path”.
The claim further requires “a platinum group metal ion-supported catalyst” and that “the platinum group metal ion-supported catalyst is a platinum group metal ion-supported catalyst in which platinum group metal ions or platinum group metal complex ions are supported on a non- particulate organic porous ion exchanger, wherein the non-particulate organic porous ion exchanger is formed of a continuous framework phase and a continuous pore phase; has a thickness of a continuous framework of 1 to 100 4m, an average diameter of continuous pores of 1 to 1000 pm, and a total pore volume of 0.5 to 50 ml/g; has an ion exchange capacity per weight in a dry state of 1 to 9 mg equivalent/g; and has ion exchange groups wherein the ion exchange groups are uniformly distributed in the organic porous ion exchanger,” to which Hattori teaches use of a 10% Pd/C (dry type) catalyst (Pg. 22, 3.1).
Takada teaches a platinum group metal supported catalyst for performing carbon-carbon bond forming reactions where the support is a non-particulate organic porous ion exchanger that comprises a continuous skeleton phase and a continuous pore phase, a thickness of the continuous skeleton is 1 to 100 µm, the average diameter of the continuous pores is 1 to 1000 µm, the total pore volume is 0.5 to 50 mL/g, the ion exchange capacity in a dry state is 1 to 6 mg equivalent/g, and the ion exchange groups are uniformly distributed in the organic porous ion exchanger (Abstract). In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP 2144.05 (I). In the instant case, the ranges taught by Takada (thickness of the continuous skeleton is 1 to 100 µm, the average diameter of the continuous pores is 1 to 1000 µm, the total pore volume is 0.5 to 50 mL/g, the ion exchange capacity in a dry state is 1 to 6 mg equivalent/g) overlap with the claimed ranges (thickness of a continuous framework of 1 to 100 µm, an average diameter of continuous pores of 1 to 1000 µm, and a total pore volume of 0.5 to 50 ml/g; has an ion exchange capacity per weight in a dry state of 1 to 9 mg equivalent/g). Therefore, the ranges in Takada render obvious the claimed ranges.
Advantageously, the catalyst of Takada displays high activity in carbon-carbon bond forming reactions and allows for efficient reactions (Pg. 2, Description, par. 6-7).
Thus, prior to the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to use a platinum group metal supported catalyst where the support is a non-particulate organic porous ion exchanger that comprises a continuous skeleton phase and a continuous pore phase, a thickness of the continuous skeleton is 1 to 100 µm, the average diameter of the continuous pores is 1 to 1000 µm, the total pore volume is 0.5 to 50 mL/g, the ion exchange capacity in a dry state is 1 to 6 mg equivalent/g, and the ion exchange groups are uniformly distributed in the organic porous ion exchanger in the process of Hattori in order to use a catalyst with high activity in carbon-carbon bond forming reactions that enable efficient reactions, as taught by Takada.
The claim further requires “platinum group metal ions or platinum group metal complexes” are supported on the support. Hattori is silent regarding this limitation and Takada teaches platinum group metal nanoparticles are supported on the support (Claims, Pg. 2, Description, par. 8) but is silent regarding ions or complexes explicitly being on the support.
Trejo O’Reilly teaches a heterogenous catalyst for performing carbon-carbon bond forming reactions where the heterogenous catalyst includes a palladium loaded cationic exchange resin where the palladium can be loaded as an ion ([0011]).
Advantageously, supports loaded with ionic palladium provides catalysts with higher efficiency compared with supported palladium catalysts produced otherwise, while also displaying higher thermal stability ([0003]).
Thus, prior to the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to incorporate palladium ions in the support of Takada in the process Hattori in order to provide a catalyst with improved efficiency and high thermal stability, as taught by Trejo O’Reilly.
Regarding claim 9, Hattori teaches the cross-coupling reaction was performed with Na2CO3 (i.e. sodium carbonate) (Table 1; Pg. 22, 3.2). Inorganic bases are described in the instant specification at [0242] to “include sodium carbonate, sodium bicarbonate, potassium carbonate, cesium carbonate, potassium acetate, sodium phosphate, potassium phosphate, potassium phenoxide, barium hydroxide, sodium methoxide, sodium ethoxide, potassium butoxide, trimethylamine, and triethylamine.” Accordingly, Hattori teaching sodium carbonate meets the limitation of an “inorganic base”.
Regarding claim 10, Hattori teaches the inorganic base, sodium carbonate, is a solution in water which is combined with the aryl halide and arylboronic acid raw materials as a solution that is then passed through a catalyst-packed cartridge, where the catalyst contains Pd supported on carbon, prior to collecting the reaction solution exiting the catalyst-packed cartridge (i.e. Pd/C) (Pg. 22, 3.2).
Claim 11 is rejected under 35 U.S.C. 103 as being unpatentable over Hattori et al. (Catalysts 2015, 5, 18-25) in view of Takada et al. (JP2014015420A; cited in IDS dated 06/26/2023) and Trejo O Reilly et al. (US20150353445A1) and further in view of Bolton et al. (Tet. Lett. 2006, 47, 9321-9324) with evidentiary support provided by Cao et al. (RSC Adv. 2017, 7, 25535).
Regarding claim 11, Hattori in view of Takada and Trejo O Reilly teach the process of claim 8.
The claim further requires the raw material liquid is “a hydrophobic solvent raw material liquid” and that the raw material is “dissolved in a hydrophobic organic solvent” when the carbon-carbon bonding forming reaction is performed. Hattori, Takada and Trejo O Reilly are silent regarding using a hydrophobic solvent.
Bolton teaches a process for using solid microporous monoliths anchored with palladium complexes to perform Suzuki-Miyaura couplings in continuous flow capillary microreactors (Title; Abstract; Pg. 9322, right col.). Bolton teaches the reagents for the Suzuki-Miyaura reaction are iodobenzene and p-tolyboronic acid that are dissolved in a 9:1 ratio of toluene/methanol solvent before being fed to the capillary containing the catalyst monolith (Pg. 9322, left and right col.; Pg. 9323, left col.; Table 1). Toluene is known by skilled artisans to be a hydrophobic solvent, as evidenced by Cao et al. (Pg. 25536, left col.).
Regarding the term “hydrophobic solvent,” the term is not given an expressed definition in the instant specification and the art-accepted meaning of “hydrophobic solvent” was applied. Additionally, the carbon-carbon cross-coupling reaction solvent is described in the instant specification as “not particularly limited as long as the solvent does not inhibit the carbon-carbon bond-forming reaction” and that the solvent can include toluene and methanol [0240].
Accordingly, Bolton teaching a solvent of 9:1 toluene/methanol that effectively carries out Suzuki-Miyaura cross-coupling reactions (Table 1) meets the limitation of a “hydrophobic solvent”.
Advantageously, the 9:1 toluene/methanol solvent mixture ensures that the reaction raw materials form a homogenous liquid phase that does not block the microreactor pathway (Pg. 9322, right col.).
Thus, prior to the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to utilize a hydrophobic solvent like toluene as a 9:1 toluene/methanol solvent mixture to dissolve the aryl halide and organoboron in the process Hattori in order to ensure a homogenous liquid phase of the reactants and limit blockage of the flow reactor, as taught by Bolton.
Conclusion
Applicant's amendment necessitated the new 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 nonprovisional extension fee (37 CFR 1.17(a)) 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 Jordan Wayne Taylor whose telephone number is (571)272-9895. The examiner can normally be reached Monday - Friday, 7:30 AM - 5 PM EST; Second Fridays Off.
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/JORDAN W TAYLOR/Examiner, Art Unit 1738
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