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 .
Status of the Claims
The preliminary amendment filed on 06/13/2023 has been entered. Claims 4-5, 7-12, 15-18, 20, 22, 25 and 31 have been amended and claims 6, 14, 19, 21, 23-24, and 26-30 have been canceled. Thus, claims 1-5, 7-13, 15-18, 20, 22, 25 and 31 are currently pending and are under examination.
Claim Objections
Claim 5 is objected to because of the following informalities: the claim recites “selected from the group consisting is selected from the group consisting of” is replete with idiomatic errors. Appropriate correction is required.
Claim 13 is objected to because of the following informalities: replace “(VO(acac)2” in line 4 with “VO(acac)2”.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1-5, 7-13, 15-18, 20, 22, 25 and 31 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Regarding claims 1 and 30, the phrase “related compound” renders the claims vague and indefinite because the phrase does not limit the claims to the recited specie, vanillin, and thus is unclear as to how much variation of the recited specie is tolerated by the use of phrase “related compound”.
Claims 2-5, 7-13, 15-18, 20, 22, 25 and 31 are also rendered indefinite for their dependency on claim 1.
Regarding claims 2-3, the limitation “monomeric analogues thereof” is indefinite because it is unclear what monomers of lignin are encompassed by the limitation.
Regarding claim 2:
The phrase "such as" in lines 2 and 3 renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
The phrase “derivatives thereof” renders the claims vague and indefinite because the phrase does not limit the claim to the recited specie, cinnamic acid, and thus is unclear as to how much variation of the recited specie is tolerated by the use of phrase “derivatives thereof”.
Regarding claims 13 and 16, the phrase "such as" renders the claims indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
Regarding claim 18, the claim is dependent on the canceled claim 14 and thus the scope of the claim is vague and indefinite. For purpose of applying art, the claim is interpreted as depending on claim 12.
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.
Claims 1-5, 7, 22 and 25 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Popova (Popova, N. P. et al “Supported Polyoxometalate Catalysts for Oxidation Processes” Russian Journal of Applied Chemistry, 2018, Vol. 91, No. 1, pp. 49−52) as evidenced by Zexer (Zexer, N. et al. “Unique lignin modifications pattern the nucleation of silica in sorghum endodermis” Journal of Experimental Botany, Vol. 71, No. 21 pp. 6818–6829, 2020).
Regarding claim 1-2, 4 and 7, Popova teaches a process for the production of vanillin by reacting ferulic acid with peroxyacetic acid in the presence of a vanadium compound catalyst (Table on pg. 52).
Regarding claims 1-3, Popova is silent that ferulic acid is a lignin monomer, however as evidenced by Zexer, ferulic acid is a common monomer of lignin (pg. 6819, 2nd col.).
Regarding claim 5, the structure of ferulic acid is as follows, which is a specie of claimed formula (I):
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Regarding claims 22 and 25, Popova teaches in the table that the reaction is conducted at a temperature of 25 °C for 30 min.
Claims 1-4, 7, 10-12, 15, 22, 25 and 31 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Huang (Huang, H. et al “Ionic Liquid-mediated Catalytic Oxidation of Isoeugenol to Vanillin via Oxovanadium 1,3,5-Benzenetricarboxylate” Chinese J. Appl. Chem. 2014, 31, 8, 952-957 and machine translation of Experimental) as evidenced by Du (Du, B. et al. “A Comparison of Phenolic Monomers Produced from Different Types of Lignin by Phosphotungstic Acid Catalysts” Chemistry Open 2019, 8, 643–649).
Regarding claim 1-2, 4, 7 and 10, Huang teaches a process for the production of vanillin and vanillin derivatives by reacting isoeugenol with H2O2 in the presence of different vanadium compound catalysts (Table 1 on pg. 954).
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Regarding claims 1-3, Huang is silent that isoeugenol is a lignin monomer, however as evidenced by Du, isoeugenol is one of the monomers derived from lignin.
Regarding claim 11, Huang teaches that H2O2 is provided as 50% aqueous solution.
Regarding claim 12, one of the vanadium compound catalysts is V2O5.
Regarding claim 15, 25 mg of V2O5 (equivalent to about 1.37x10-4 moles based on 181.88 g/mol) and 10 mmol of isoeugenol (equivalent to 1.62 g based on 164.2 g/mol) have been used. In isoeugenol, there is one aromatic ring, C6H3, wherein 75.10 g/mol is the molar mass of the aromatic ring in isoeugenol. The amount of the aromatic ring in 1.62 g of isoeugenol is 0.74 g (or about 0.0098 moles based on 75.1 g/mol). Thus, the catalyst is employed in an amount of about 0.014 equivalents per the aromatic ring (calculated from 1.37x10-4 moles/0.0098 moles).
Regarding claims 22 and 25, Huang teaches in Table 1 that the reaction is conducted at a temperature of 20 °C for 4 h.
Regarding claim 31, Huang teaches recovering of vanillin and vanillin derivatives by extraction with ethyl acetate (machine translation in the last page).
Claims 1-4, 7, 10-11, 16, 20, 22 and 25 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Maurya (Maurya, M. et al “Synthesis and characterization of di-µ-oxidovanadium(V), oxidoperoxido-vanadium(V) and polymer supported
dioxidovanadium(V) complexes and catalytic oxidation of isoeugenol” Inorg. Chim. Acta 2015, 434, 230-238) as evidenced by Du (Du, B. et al. “A Comparison of Phenolic Monomers Produced from Different Types of Lignin by Phosphotungstic Acid Catalysts” Chemistry Open 2019, 8, 643–649).
Regarding claim 1-2, 4, 7 and 10, Maurya teaches a process for the production of vanillin and vanillin derivatives by reacting isoeugenol with H2O2 in the presence of different vanadium compound catalysts (sect. 2.5, pg. 232 and scheme on pg. 235).
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Regarding claims 1-3, Maurya is silent that isoeugenol is a lignin monomer, however as evidenced by Du, isoeugenol is one of the monomers derived from lignin.
Regarding claim 11, Maurya teaches that H2O2 is provided as 30% aqueous solution.
Regarding claim 16, 0.2 g of the catalyst (equivalent to about 2.68x10-4 moles based on 746.47 g/mol) and 0.82 g of isoeugenol have been used. In isoeugenol, there is one aromatic ring, C6H3, wherein 75.10 g/mol is the molar mass of the aromatic ring in isoeugenol. The amount of the aromatic ring in 0.82 g of isoeugenol is 0.375 g (or about 0.00499 moles based on 75.1 g/mol). Thus, the catalyst is employed in an amount of about 0.05 equivalents per the aromatic ring (calculated from 2.68x10-4 moles/0.00499 moles).
Regarding claim 20, Maurya teaches that the solvent is acetonitrile.
Regarding claim 22, Maurya teaches that the reaction is conducted at a temperature of 80 °C for 2 h.
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.
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.
Claim 8 is rejected under 35 U.S.C. 103 as being unpatentable over Maurya (Maurya, M. et al “Synthesis and characterization of di-µ-oxidovanadium(V), oxidoperoxido-vanadium(V) and polymer supported dioxidovanadium(V) complexes and catalytic oxidation of isoeugenol” Inorg. Chim. Acta 2015, 434, 230-238).
The teachings of Maurya have been set forth above.
Regarding claim 8, as set forth above, the amount of the aromatic ring in 0.82 g of isoeugenol is 0.375 g (or about 0.00499 moles based on 75.1 g/mol). Furthermore, 10 mmol of 30% H2O2 has been used. Thus, H2O2 is employed in an amount of about 2 equivalents per aromatic of the aromatic compound (calculated from 10 mmol/0.00499 moles), which is close to the claimed amount of 5 to 40 equivalents per aromatic of the aromatic compound. In view of MPEP § 2144.05, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close absent any showing of unexpected results or criticality.
It would thus have been prima facie obvious to a skilled artisan to produce vanillin or a related compound comprising the step of reacting an aromatic compound with a peroxide in the presence of a suitable catalyst, wherein said catalyst is a vanadium compound, wherein the peroxide is employed in amount of t to 40 equivalents per aromatic ring of the aromatic compound in view of the teachings of Maurya.
Claim 16 is rejected under 35 U.S.C. 103 as being unpatentable over Huang (Huang, H. et al “Ionic Liquid-mediated Catalytic Oxidation of Isoeugenol to Vanillin via Oxovanadium 1,3,5-Benzenetricarboxylate” Chinese J. Appl. Chem. 2014, 31, 8, 952-957 and machine translation of Experimental).
The teachings of Huang have been set forth above.
Regarding claim 16, the amount of 0.014 equivalents per the aromatic ring taught by Huang is merely close to that of claim 16, 0.02 to 0.1. In view of MPEP § 2144.05, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.
It would thus have been prima facie obvious to a skilled artisan to produce vanillin or a related compound comprising the step of reacting an aromatic compound with a peroxide in the presence of a suitable catalyst, wherein said catalyst is a vanadium compound, wherein the catalyst is vanadium oxide and the vanadium oxide is employed in amount of 0.02 to 0.1 equivalents per aromatic ring of the aromatic compound in view of the teachings of Huang.
Allowable Subject Matter
The subject matter of claims 9 and 17-18 is free of prior art references. The closest prior art reference is Patent number KR20200125037A (KR’037).
KR’037 teaches a method for producing vanillin or vanillic acid from a composition comprising lignin, the method comprising an oxidizing agent, a base catalyst, and an oxide catalyst comprising Cu or Mn, wherein the oxidizing agent is oxygen (O2), ozone (O3) nitrobenzene, hydrogen peroxide (H2O2 ), halogens (fluorine, chlorine, etc.), nitrogen oxides (N2O, NO2, etc.), organic peroxides, peracid (peracetic acid, performic acid, persulfuric acid, pernitric acid, metachloroperoxybenzoic acid, perchloric acid, etc.) and peroxides ([0013], [0017] and [0024]). However, KR’037 fails to teach or suggest that the catalyst is a vanadium compound.
Furthermore, the references set forth above, Popova, Huang, and Maurya, teach the use of vanadium compound as the catalyst and peroxide as an oxidizing agent in converting different aromatic starting compounds to vanillin and vanillin derivatives. Due to the difference in the chemical nature of lignin from these aromatic starting compounds, the conversion of the aromatic compounds of Popova, Huang, and Maurya to vanillin would be expected to undergo via a different mechanism than the conversion of lignin to vanillin. As such, replacing Cu or Mn catalyst of KR’037 with the vanadium compound catalyst of Popova, Huang, or Maurya, one of ordinary skill in the art would not have a reasonable expectation of success in obtaining vanillin or vanillic acid from lignin.
In view of the foregoing, claims 9, 17 and 19 are deemed novel and unobvious over the closest prior art.
Conclusion
Claims 1-5, 7-13, 15-18, 20, 22, 25 and 31 are rejected and no claims are allowed.
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/MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692