E 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 .
Specification
The disclosure is objected to because of the following informalities:
On pages 3 and 4 (see paragraphs 0014, 0016 and 0017) references 36-41 are mentioned. However, the list of references ended with number 35 (see paragraph 0115 at page 15).
Appropriate correction is required.
Claim Rejections - 35 USC § 102
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.
Claims 1-2 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Yang et al (Electrochemical oxidation of biomass derived 5-hydroxymethylfurfural (HMF): pathway, mechanism, catalysts and coupling reactions, Green Chem., 2021, 23, 4228-4254, published on 21 May 2021)
Yang teaches a method of polyethylene furanoate (PEF) production, which includes dehydration of hexoses (mainly fructose) producing 5-Hydroxymethylfurfural (HMF) (see page 4229, left column) and electrooxidation of HMF to furandicarboxylic acid (FDCA) (see Abstract), which pair to Hydrogen production (see page 4244, left column , chapter “Coupling hydrogen evolution reaction (HER)”).
Claim Rejections - 35 USC § 103
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.
Claim 3 and 8-9 is rejected under 35 U.S.C. 103 as being unpatentable over Yang in view of
Claim3 and 8-9 are rejected under 35 U.S.C. 103 as being unpatentable over Yang as applied to claims 1-2 above, and further in view of Lu et al (Identifying the Geometric Site Dependence of Spinel Oxides for the Electrooxidation of 5-Hydroxymethylfurfural, Angew. Chem. Int. Ed. 2020, 59, 19215 – 19221).
Yang teaches activated ZnCo2O4 for HMF electrooxidation (see page 4240, left column).
However, the reference fails to teach a detailed description of the process above.
Lu teaches ZnCo2O4 activated spinel catalyst (see Figure 1 at page 19216) for HMF electrooxidation.
In reference to claim 3, Lu teaches that Co3O4 , ZnCo2O4 and CoAl2O4 were prepared via the one step solvothermal method (see page 19216, left column), at the calcination temperature of up to 600C (see Figure 1 (e) at page 19216).
The reference does not disclose Ni foam substrate for ZnCo2O4 catalyst. However, such substrate is used for similar CuCo2O4 and Co3O4 catalysts (see Figure 3c at page 19219) and therefore, it can be used for all Cobalt- based catalysts.
Lu discloses a record performance of Co-based catalysts (see Figure 3d and page 19219, right column).
Therefore, it would have been obvious to a person of ordinary skills in the art before the effective filing date of the invention to use Lu’s activated spinel catalyst in Yang’s process since it demonstrated very good performance in an analogous process.
Note that highest performance is recorded for CuCo2O4 on Nickel foam substrate.
The position is taken the similar performance can be expected for analogous ZnCo2O4 catalyst on the same substrate.
In accordance to MPEP 2144.09 the structural analogs are prima facie obvious in the absence of showing unexpected results.
Therefore, it would have been obvious to a person of ordinary skills in the art before the effective filing date of the invention to expect high performance of ZnCo2O4 for HMF electrooxidation on Ni foam substrate, since such results were achieved on similar CuCo2O4 catalyst, unless unexpected results are demonstrated.
In reference to claims 8-9, Lu teaches that electrochemical performances of ZnCo2O4 and CuCo2O4 catalysts are very similar to the catalytic system of instant Application. For instance, the onset potential of HMF oxidation for CuCo2O4 is only 1.23 VRHE, which is much lower than the pristine Co3O4 (1.30 VRHE) and CuO (1.41 VRHE) (see Figure 3 at page 19219). Note electrochemical activity of CuCo2O4 electrocatalysts determined in 1.0 m KOH with 50 mm HMF electrolyte, which is similar to Applicant’s experimental conditions (see printed publication, Figure 6).
However, the prior art cited does not teach the exact production characteristics disclosed in claims 8 and 9.
The position is taken that since Yang modified by Lu and Applicant teach the same ZnCo2O4 catalyst in the alkaline media, their performances are expected to be identical.
The claiming of a new use, new function or unknown property, which is inherently present in the prior art, does not necessarily make the claim patentable. In re Best, 562 F.2d 1252, 1254, 195 USPQ 430, 433 (CCPA 1977).
Therefore, it would have been obvious to a person of ordinary skills in the art before the effective filing date of the invention to expect the same production characteristics from modified Yang’s and Applicant reacting systems, since they are identical.
Claim 4 -7 and 12 are rejected under 35 U.S.C. 103 as being unpatentable over Yang in view of Lu as applied to claims 1-3 above, and further in view of Chen et al (Highly Efficient Two-Step Synthesis of 2,5-Furandicarboxylic Acid from Fructose without 5‑Hydroxymethylfurfural (HMF) Separation: In Situ Oxidation of HMF in Alkaline Aqueous H2O/DMSO Mixed Solvent under Mild Conditions, Ind. Eng. Chem. Res. 2018, 57, 16172−16181).
Yang and Lu disclose sodium hydroxide solution, but fail to teach potassium carbonate-based alkaline solution.
Regarding claims 3 and 7, Chen teaches a method of making FDCA from HMF using different media, including NaOH, KHCO3 and K2CO3 (see Abstract and Table 2 at page 16176, left column).
The reference teaches that when potassium carbonate was used, the FDCA yield reached 91.1% at 12 h, with only 0.3% FFCA formed as byproduct (see page 16176, left column).
Therefore, it would have been obvious to a person of ordinary skills in the art before the effective filing date of the invention to use potassium carbonate based solution for synthesis of FDCA from HMF, since it demonstrates best result among alkali solutions in terms of yield and by-product content.
Regarding dosage of potassium carbonate, recited in claims 5 and 6, Chen teaches that K2CO3/HMF ratio as high as 2 is necessary in theory for HMF oxidation. At K2CO3/HMF ratio of 2, excessive K2CO3 always exists to promote the oxidation reaction because only partial K2CO3 is used to dissolve FDCA, FFCA, and HMFCA in the reaction system before reaching 100% FDCA yield (see page 16177, left column).
Regarding claim 12, Chen discloses that the reaction mixture obtained under the optimized
oxidation condition was filtrated to remove catalyst and any other possible insoluble solids. The filtrate was concentrated by rotary evaporation and then acidified with hydrochloric acid (until pH 2) to precipitate FDCA. After filtration, washing with 5 mL of deionized water three times, and drying at 80 °C
for 24 h, FDCA was finally obtained (see page 16173, right column).
Claim 10 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Yang in view of Zhang et al (Facile synthesis and isolation of 5-hydroxymethylfurfural from diphenyl sulfoxide, Green Chem., 2021, 23, 3241–3245).
Yang fails to teach a synthesis of HMF from fructose using diphenyl sulfoxide.
Zhang teaches a 5-hydroxymethylfurfural (HMF) from fructose using diphenyl sulfoxide (DPhSO) (see Abstract).
The reference discloses that the reaction carries out at 140C (see page 3243, left column) with following easy HMF extraction (see Abstract). Thus, pure HMF can be directly fed to the cell for subsequent synthesis (meeting the corresponding limitations of claim 11)
In addition, Zhang teaches that DPhSO possesses catalytic ability.
Therefore, it would have been obvious to a person of ordinary skills in the art before the effective filing date of the invention to use DPhSO in HMF synthesis from fructose, since it is environmentally friendly solvent, having catalytic activity.
Claim 13 and 14 are rejected under 35 U.S.C. 103 as being unpatentable over Yang in view of Van Berkel (On the Physical Properties of Poly(ethylene 2,5-furandicarboxylate), PhD thesis, Institut de Chimie de Nice).
Yang fails to teach specifics of PEF synthesis from FDCA and polymer pellets.
Van Berkel teaches a two- step synthesis of PEF from FDCA, which includes pre-condensation and solid state polymerization (SSP) with following pelletization (see Figure 7 at page 20).
Van Berkel further discloses that the process above is widely used in industry and identical to a process for polyethylene terephthalate synthesis and processing (see page 20)
Therefore, it would have been obvious to a person of ordinary skills in the art before the effective filing date of the invention to use Van Berkel’s two step polycondensation of FDCA to PEF withy following palletization, since it is commercially known process.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to GREGORY LISTVOYB whose telephone number is (571)272-6105. The examiner can normally be reached 9am-5pm EST M-F.
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GL
/GREGORY LISTVOYB/Primary Examiner, Art Unit 1765