DETAILED ACTION
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 08/10/2026 has been entered.
The papers submitted on 10 Aug. 2026, amending claim 1 are acknowledged.
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 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 (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 1-4, 6-9, and 11-15 are rejected under 35 U.S.C. 103 as being unpatentable over Riguetto et al. (“Ru-Sn catalyst for selective hydrogenation of crotonaldehyde: Effect of the Sn/(Ru+Sn) ratio”), and further in view of Bai et al. (US 20160193592 A1).
Regarding claim 1, Riguetto et al. discloses production of Ru-Sn/SiO2 catalyst by incipient wetness impregnation of silica with aqueous solution containing appropriate amounts of ruthenium and tin precursors (2.1 Sample preparation). The Ru-Sn/SiO2 catalyst samples are dried and then reduced in a fixed-bed glass reactor heated to 773K while flowing H2 (2.1 Sample preparation).
Riguetto et al. discloses heating the reactor at rate of 10Kmin-1 (equivalent to 10 C/min), but does not disclose heated a rate of 1°C/min to 5°C/min.
Bai et al. discloses a method of preparing a hydrogenation catalyst comprising a treated silica-supported ruthenium (Abstract). The silica-supported ruthenium catalyst is prepared by incipient wetness impregnation and dried in air followed by calcination in air (paragraph 0058). The calcined catalyst is reduced at 425 °C for 2.5 hours with 100% hydrogen (paragraph 0059). The reduction reactor is ramped from room temperature to 425 °C at 5 °C/min (paragraph 0059).
Therefore, it would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention, to reduce Riguetto et al. catalyst with a 5 °C/min ramp rate because such heating rates of 1 to 5 °C/min are known and conventional in the art for incipient-wetness impregnated catalysts.
Additionally, a 103 rejection without the Bai et al. reference can be made. Riguetto et al. discloses the heating rate of 10K/min (equivalent to 10°C/min) (2.1 Sample preparation). A prima facie case of obviousness exists when the claimed range or amount does not overlap with the prior art but is merely close. One skilled in the art would expect a bimetallic catalyst reduced at a ramp rate of 10°C/min to have the same properties as a bimetallic catalyst with a ramp rate of 1°C/min to 5°C/min. See MPEP 2144.05, I. Titanium Metals Corp. of America v. Banner, 778 F.2d 775, 783, 227 USPQ 773, 779 (Fed. Cir. 1985). Further support for the prior art and present invention having the same properties is in the applicant’s specification: a rate exceeding 15 °C/min can cause accelerated metal sintering due to rapid supply of heat (specification, paragraph 61). The rate disclosed in Riguetto et al. is below this critical value.
Regarding claim 2, Riguetto et al. discloses the first metal can be Pt, Ru, or Rh and the second metal can be Fe or Sn (1. Introduction).
Regarding claim 3, Riguetto et al. discloses a sample that is 3% by mass ruthenium and 5% by mass tin (2.1 Sample preparation) (Table 1). With a 100g basis the molar ratio of ruthenium to tin is 0.705. This is within the claimed range of 1/3 to 2.
Regarding claim 4, Riguetto et al. discloses a carrier that is silica (2.1 Sample preparation).
Regarding claim 6, Riguetto et al. discloses a sample that is 3% ruthenium by mass and 5% tin by mass for a total of 8% bimetallic compound by mass (Table 1). The claimed range is 1-20 parts by weight of bimetallic compound based on 100 parts by weight carrier which is a mass percentage of 1/101 to 20/120 bimetallic compound. 8% is within this range.
Regarding claim 7, Riguetto et al. discloses a heating rate of 10K/min (equivalent to 10°C/min) (2.1 Sample preparation).
Regarding claim 8, Riguetto et al. discloses the reduction being carried out in a fixed-bed glass reactor (2.1 Sample preparation).
Regarding claim 9, Riguetto et al. discloses the reduction in hydrogen (2.1 Sample preparation).
Regarding claim 11, Riguetto et al. discloses keeping the reactor at a high temperature for 20 minutes (2.1 Sample preparation).
Regarding claim 12, Riguetto et al. discloses the reactor being kept at 773 K (500 °C) (2.1 Sample preparation).
Regarding claim 13, Riguetto et al. discloses a rate of 10 K/min from room temperature to 773 K. If we assume room temperature is 298 K. heating will take roughly 48 minutes. Plus 20 minutes of temperature maintenance gives a little over an hour of total time.
Regarding claim 14, Riguetto et al. discloses the catalyst are used for the vapor-phase hydrogenation of crotonaldehyde (2.3 Catalytic reaction).
Regarding claim 15, Riguetto et al. discloses the catalysts are used for the vapor-phase hydrogenation of crotonaldehyde which is an aldehyde (2.3 Catalytic reaction). The Ru-Sn catalyst is active in the hydrogenation of both the C=O and C=C bonds (3.4 Reaction data) which forms butanol and crotyl alcohol.
Claims 5, 10, and 16-18 are rejected under 35 U.S.C. 103 as being unpatentable over Riguetto et al. in view of Bai et al. as applied to claims 1-4, 6-9, and 11-15 above, and further in view of Kim et al. (KR 20200082915 A).
Regarding claim 5, modified Riguetto et al. discloses the catalyst is supported by Silica but does not disclose a carbon carrier.
Kim et al. discloses reducing a bimetallic hydrogenation catalyst by heating and supplying a reducing gas (paragraph 0089 & 0091). Kim et al. discloses the catalyst has a carbon carrier that can be activated carbon, carbon black, graphite, graphene, OMC, or CNT (paragraph 0062).
Therefore, it would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention, to further modify Riguetto et al. by substituting the silica carrier with one of the carbon carriers in Kim et al. because those forms of carbon are common for supporting catalytic metals in hydrogenation catalysts.
Regarding claim 10, Kim et al. discloses preparation of a catalyst using ruthenium and tin precursors solutions with 3.9 g of RuCl3 and 3.5 g of SnCl2 (paragraph 0100). The precursor solution is added to 10 g of the carbon carrier. Using conservation of mass, we cannot have more than 3.9 g of Ru, 3.5 g of Sn, and 10 g of carbon. Therefore we will use the absolute maximum values to anticipate this claim since the gas supplied needs to be greater. A table below shows calculations.
Ruthenium (Ru)
Tin (Sn)
Mass = 3.9 g
Mass = 3.5 g
Wt frac = 3.9g/(10 g + 3.5 g + 3.9 g) = 0.224
Wt frac = 3.5 g/(10 g + 3.5 g + 3.9 g) = 0.201
Mol/unit mass = 0.224/101.07 g/mol = 0.00222 mol/g catalyst
Mol/unit mass = 0.201/118.71 g/mol = 0.00169 mol/g catalyst
Moles of bimetallic compound per unit mass of catalyst = 0.00222 mol/g catalyst + 0.00169 mol/g catalyst = 0.00391 mol/g catalyst. Kim et al. discloses reducing at a flowrate of 100 cubic cm/min 30% H2 and flowing for 3 hours (paragraph 0100). Calculations are shown below for the total mols of H2
Assuming ideal gas: PV=nRT
30 cc/min = 0.03 L/min
(1atm)(0.03L/min)=n(0.08206 L*atm/(mol*K))(773K)
n =(5*10-4 mol/mins)(60min/1hr)(3hrs) = 0.09 mol
Therefore, the experimental example supplies a greater amount of reducing gas than the number of moles of bimetallic compound per mass of catalyst.
Regarding claim 16, Kim et al. discloses producing a cyclohexane dimethanol through a hydrogenation reaction of cyclohexane dicarboxylic acid (paragraph 0001). The dicarboxylic acid is reduced to a dialcohol group.
Regarding claims 17-18, Kim et al. discloses using a reduced bimetallic catalyst in a hydrogenation reaction of cyclohexane dicarboxylic acid producing cyclohexane dimethanol at a yield of 85-99% (paragraph 0074). It is noted that claims 17-18 are directed to a process of using a product by process. The product by process limitations are noted. However, when the examiner has found a substantially similar product as in the applied prior art, the burden of proof is shifted to applicant to establish that their product is patentably distinct and not he examiner to show the same process of making. In re Brown, 173 USPQ 685 and In re Fessmann, 180 USPQ 324.
Response to Arguments
Applicant’s arguments, see pages 6-11, filed 08/10/2026, with respect to the rejection(s) of claims 1, 2, 4, and 6-16 under 35 U.S.C. 102(a)(1) (Haider), claim 3 under 35 U.S.C. 103 (Haider), and claims 1-5, 9-12, 14-18 under 35 U.S.C. 103 (Kim in view of Haider) have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground of rejection is made in view of Riguetto et al. and further in view of Bai et al. under 35 U.S.C. 103. Riguetto et al. contains the amended limitation of co-impregnating with incipient-wetness and all other original limitations, and Bai et al. contains the heating rate. Additionally, rejections have been made in further view of Kim et al. for all limitations not disclosed in Bai et al. and Riguetto et al.
Conclusion
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/DAVID ANDREW CALDERON/Examiner, Art Unit 1742 /CHRISTINA A JOHNSON/Supervisory Patent Examiner, Art Unit 1742
