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 .
Drawings
The drawings were received on 08/01/2023. These drawings are acceptable.
Priority
Acknowledgment is made of applicant’s claim for foreign priority under 35 U.S.C. 119 (a)-(d). The certified copy has been filed in parent Application No. KR-10-2021-0013970, filed on 02/01/2022.
Claim Rejections - 35 USC § 102
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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1, 2, 4, and 6-16 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Haider et al. (WO2019234553A2).
Regarding claim 1, Haider et al. discloses bimetallic catalyst that is capable of producing butadiene in a single step process (paragraph 0006). The catalyst can include a Column 13 or Column 14 metal and a noble metal deposited on an iron-magnesium-silicon oxide support (paragraph 0002). In an embodiment of the invention, a bimetallic (GaPd) supported catalyst (FeMgSiO support) is created (paragraph 0044). The catalyst is subjected to activation/reduction procedure where the reactor is heated to 250 °C, 350 °C, and 450 °C (paragraph 0045). A ramp rate of 3°C/min is used (paragraph 0045). The gas H2 is flowed (paragraph 0045).
Regarding claim 2, Haider et al. discloses the bimetallic catalyst consists of Pd and Ga (paragraph 0044). Additionally, Haider et al. discloses noble metal and column 13 and 14 periodic table metal alloys of Rh, Pd, Ru, Pt, and Ga (paragraph 0026).
Regarding claim 4, Haider et al. discloses the catalyst is supported with an iron-stabilized alkaline earth metal-silica support (paragraph 0026).
Regarding claim 6, Haider et al. discloses the catalyst of the present is from 0.001 wt% to 20 wt% metal with the balance support (paragraph 0026). This corresponds to 0.0001 parts by weight to 25 parts by weight based on 100 parts by weight of support encompassing the claimed range. An example calculation is shown below.
100 parts by weight of support, 20 wt% of bimetallic, solve for part by weight of bimetallic
Bimetallic wt ratio = 0.2 = Bimetallic part by weight/(Bimetallic part by weight + 100)
Bimetallic part by weight = 25
Regarding claim 7, Haider et al. discloses the ramp rate of the reduction is 3 °C/min (paragraph 0045).
Regarding claim 8, Haider et al. discloses the evaluation of the catalyst is done in a fixed bed reactor (paragraph 0045). The evaluation includes the reduction of the catalyst (paragraph 0045).
Regarding claim 9, Haider et al. discloses 10:90 H2/N2 flow in the reduction process (paragraph 0045).
Regarding claim 10, Haider et al. discloses preparation of the GaPd catalyst. The support solution consists of 20 mL of 1M magnesium chloride solution (1.904 g magnesium chloride), 10.4g of tetraethyl orthosilicate, and 0.25 g ferric citrate crystals (paragraph 0044). The support material is suspended and 0.35 g of Gallium oxide and 0.56 g of Palladium nitrate dihydrate are added (paragraph 0044). Using conservation of mass, we cannot have more than 0.56 g Pd, 0.35 g Ga, and 12.554 g of support. 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.
Gallium (Ga)
Palladium (Pd)
Mass = 0.35 g
Mass = 0.56 g
Wt frac = 0.35 g/(0.35 g + 0.56 g + 12.554 g) = 0.026
Wt frac = 0.56 g/(0.35 g + 0.56 g + 12.554 g) = 0.042
Mol/unit mass = 0.026/69.723 g/mol = 0.00037 mol/g catalyst
Mol/unit mass = 0.042/106.42 g/mol = 0.00039 mol/g catalyst
Moles of bimetallic compound per unit mass of catalyst = 0.00076 mol/g catalyst.
Haider et al. discloses reduction with a flow of 10:90 H2/N2 1200 1/h WHSV (paragraph 0045). The mass of the catalyst in the reactor is 0.5 g (paragraph 0045). Calculations below show how the molar flow rate is found.
WHSV = Mass flow Rate of Feed/Mass of Catalyst
Mass flow rate of feed = 1200 1/h * 0.5 g = 600 g/h
H2 flow rate = 0.1*600 g/h = 60 g/h
H2 molar flow = (60 g/h)/(2.02 g/mol) = 29.7 mol/h
The gas is flowed for over an hour, so we see that the reduction supplies a greater amount of reducing gas than the number of moles of bimetallic compound per mass of catalyst.
Regarding claims 11 and 12, Haider et al. discloses the reactor is held for an hour at a temperature of 250 °C, 350 °C, and 450 °C (paragraph 0045).
Regarding claim 13, Haider et al. discloses heating with a ramp rate of 3 °C/min to temperatures of 250 °C, 350 °C, and 450 °C (paragraph 0045). Each of these temperatures are held for an hour (paragraph 0045). Using this information, we can find the time of heating and temperature maintenance of the reactor.
RT = 20 °C, Final Temperature = 450 °C
(430 °C)/(3 °C/min) = 143 minutes of heating
If we hold at all three of temperatures that is 3 hours.
180 minutes maintenance + 143 minutes heating = 323 total minutes = 5.4 hours
Regarding claims 14-16, the intended use of the product produced is noted. However, it is the
position of the examiner that the intended use does not limit the method of reducing instantly claimed.
Therefore, it is the position of the examiner that the product produced by Haider et al. would be capable of performing the intended use as claimed.
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.
Claim 3 is rejected under 35 U.S.C. 103 as being unpatentable over Haider et al.
Regarding claim 3, Haider et al. discloses the molar ratio of Ga:Pd can be 0.01 to 0.5 (paragraph 0007). A Pd:Ga ratio which is the first to second metal of the present invention would be the inverse so 1/0.01 to 1/0.5 or 100 to 2. A molar ratio of 2 is the same as the upper extreme of the claimed range 1:0.5.
A prima facie case of obviousness exists when the claimed ranges or amount do not overlap with the prior art but are merely close. One skilled in the art would expect a bimetallic catalyst with the lower portion of the molar ratio range of metals disclosed in Haidar et al. to have the same properties as a bimetallic catalyst as the claimed molar ratio range of 0.33 to 2. See MPEP 2144.05, I. Titanium Metals Corp. of America v. Banner, 778 F.2d 775, 783, 227 USPQ 773, 779 (Fed. Cir. 1985).
Claims 1-5, 9-12, and 14-18 are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (KR20200082916), and further in view of Haider et al.
Regarding claim 1, Kim et al. discloses reducing a bimetallic hydrogenation catalyst by heating and supplying a reducing gas (paragraph 0089) (paragraph 0091). The bimetallic catalyst is added to a
convection oven which serves as a reactor (paragraph 0103). Kim et al. does not disclose heating the reactor at a rate of 1 °C/min to 5 °C/min.
Haider et al. discloses bimetallic catalyst that is capable of producing butadiene in a single step process (paragraph 0006). The catalyst can include a Column 13 or Column 14 metal and a noble metal deposited on an iron-magnesium-silicon oxide support (paragraph 0002). In an embodiment of the invention, a bimetallic (GaPd) supported catalyst (FeMgSiO support) is created (paragraph 0044). The catalyst is subjected to activation/reduction procedure where the reactor is heated to 250 °C, 350 °C, and 450 °C (paragraph 0045). A ramp rate of 3°C/min is used (paragraph 0045). The gas H2, which is a reducing gas, is flowed (paragraph 0045).
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 the Kim et al. catalyst with a 3 °C/min ramp rate because such heating rates of 1 to 5 °C/min are known and conventional in the art. Kim et al. discloses a catalyst with a first metal of Pd, Rh, Ru, or Pt (paragraph 0083) and a second metal of Sn, Fe, Re, or Ga (paragraph 0084). Therefore, Kim et al. also discloses a GaPd bimetallic catalyst. One having ordinary skill in the art would have had a reasonable expectation of success to use a heating rate of 3 °C/min on the catalyst in Kim et al. because it is made of the same metals as Haidar et al.
Regarding claim 2, Kim et al. discloses a first metal of Pd, Rh, Ru or Pt (paragraph 0083) and a second metal of Sn, Fe, Re, or Ga (paragraph 0084).
Regarding claim 3, Kim et al. discloses a molar ratio of 0.5-3 with second metal/first metal (paragraph 0058). When we take the inverse to get the same ratio that is claimed, we get 0.33-2.
Regarding claim 4, Kim et al. discloses a carbon carrier (paragraph 0062).
Regarding claim 5, Kim et al. discloses a carbon carrier that can be activated carbon, carbon black, graphite, graphene, OMC, or CNT (paragraph 0062).
Regarding claim 9, Kim et al. discloses a reducing gas that is hydrogen (paragraph 0089).
Regarding claim 10, Kim et al. discloses a preparation of a catalyst using a ruthenium tin precursor solution 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 = 3.9 g/(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/min)(60min/1hr)(3hrs) = 0.09 mol
Therefore, we see that the experimental example supplies a greater amount of reducing gas than the number of moles of bimetallic compound per mass of catalyst.
Regarding claim 11, Kim et al. discloses maintaining the temperature of the reactor (paragraph 0100).
Regarding claim 12, Kim et al. discloses the reactor being maintained at 500 °C (paragraph 0100).
Regarding claim 14, Kim et al. discloses the noble metal-transition metal composite catalyst is used in a hydrogenation reaction (paragraph 0001)
Regarding claim 15, Kim et al. discloses producing cyclohexane dimethanol through a hydrogenation reaction of cyclohexane dicarboxylic acid (paragraph 0001). The carboxylic acid is reduced to an alcohol group.
Regarding claim 16, Kim et al. discloses producing 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 the 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 05/11/2026, with respect to the rejections of claims 1-4, 6-9, and 11-16 under 35 U.S.C. 102(a)(1) (Riguetto et al.) and claims 1-5, 9-12, and 14-18 under 35 U.S.C. 102(a)(1) (Kim et al.) 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 Haider et al. under 35 U.S.C. 102(a)(1) to anticipate the amended heating rate of claim 1. Additionally, a rejection of the remainder of claims not anticipated by Haider et al. is made under 35 U.S.C. 103 with Kim et al. as the primary reference and Haider et al. as the secondary.
The examiner notes that a heating rate exceeding the claim 1 range to causing metal sintering does not align with the disclosure of the application. The disclosure states that a reactor heated at a rate exceeding 15 °C/min can cause accelerated metal sintering due to rapid supply of heat (paragraph 61). Therefore, the examiner argues the claimed range of 1-5 °C/min is not a critical range that achieves the unexpected technical result of preventing sintering.
Conclusion
THIS ACTION IS MADE FINAL. 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.
/DAVID ANDREW CALDERON/Examiner, Art Unit 1742
/CHRISTINA A JOHNSON/Supervisory Patent Examiner, Art Unit 1742
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