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 .
Election/Restrictions
Applicant’s election without traverse of Group II, claims 8-11, in the reply filed on 02/05/2026 is acknowledged. Claims 1-7 are withdrawn.
Claim Objections
Claims 8-11 are objected to because of the following informalities:
Regarding claim 8, lines 1-2, the phrase “…for forming a carbon-carbon bond to form a carbon-carbon bond by performing…” is redundant and is likely intended to read “for forming a carbon-carbon bond
Regarding claim 8, line 10, the phrase “supported catalyst, into the filling container, passing…” appears to be redundant, as the prior phrase in line 9 “through an introduction path of a filling container filler with a platinum group metal-ion supported catalyst” effectively introduces the raw material liquid into the filling container. Therefore, the phrase “into the filling container” in line 10 appears redundant.
Claims 9-11 depend from claim 8 and are also objected to.
Appropriate correction is required.
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.
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”.
[AltContent: textbox (Figure 1. Reproduced reaction scheme from Hattori showing the carbon-carbon bond forming reaction)]
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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 the platinum group metal ion-supported catalyst according to claim 1,” 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) overlaps with the claimed range (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
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/JORDAN W TAYLOR/Examiner, Art Unit 1738