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 .
DETAILED ACTION
Claims 1-20 are pending.
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1-14, in the reply filed on 3/20/2026 is acknowledged.
Claims 15-20 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 3/20/2026.
Claims 1-14 are examined herein.
Specification
The disclosure is objected to because it contains an embedded hyperlink and/or other form of browser-executable code. See [0067]. Applicant is required to delete the embedded hyperlink and/or other form of browser-executable code; references to websites should be limited to the top-level domain name without any prefix such as http:// or other browser-executable code. See MPEP § 608.01.
Drawings
Color photographs and color drawings are not accepted in utility applications unless a petition filed under 37 CFR 1.84(a)(2) is granted. Any such petition must be accompanied by the appropriate fee set forth in 37 CFR 1.17(h), one set of color drawings or color photographs, as appropriate, if submitted via the USPTO patent electronic filing system or three sets of color drawings or color photographs, as appropriate, if not submitted via the via USPTO patent electronic filing system, and, unless already present, an amendment to include the following language as the first paragraph of the brief description of the drawings section of the specification:
The patent or application file contains at least one drawing executed in color. Copies of this patent or patent application publication with color drawing(s) will be provided by the Office upon request and payment of the necessary fee.
Color photographs will be accepted if the conditions for accepting color drawings and black and white photographs have been satisfied. See 37 CFR 1.84(b)(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.
Claim 12 is 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.
Claim 12 recites the limitation "each oxidation catalyst" in line 1. There is insufficient antecedent basis for this limitation in the claim. “Each” refers to every individual thing within a group, considered separately one by one. However, claim 12 depends from claim 9, which recites “an oxidation catalyst” (singular).
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1-14 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Claim 1 recites a method comprising: providing a lignocellulosic biomass reactant, fractionating the lignocellulosic biomass reactant via reductive catalytic fractionation, thereby generating a RCF oil, deoxygenating the oil via hydrodeoxygenation, thereby generating an HDO oil, and oxidizing the HDO oil, thereby generating a plurality of oxygenated monomers and bioconverting the plurality of oxygenated monomers in the presence of a genetically engineered Pseudomonas putida bacterium, thereby generating muconic acid. The broadest reasonable interpretation of claim 1 does not require oxidizing the HDO oil into any specific oxygenated monomers, so long as the oxygenated monomers can be bioconverted by a genetically engineered Pseudomonas putida bacterium. The structure of the genetically engineered Pseudomonas putida bacterium is also not limited, so long as the genetically engineered P. putida bacterium is capable of producing muconic acid from the oxygenated monomers. Claim 1 does not recite a hydrodeoxygenation or an oxidation catalyst, although these catalysts are required in dependent claims 6-7 and 9-12.
The person of ordinary skill in the art would not have recognized, at the time the application was filed, that the inventors had possession of the claimed genera of hydrodeoxygenation conditions, oxidizing conditions or genetically modified P. putida capable of bioconverting oxygenated monomers into muconic acid.
The specification discloses that the RCF oil was subjected to hydrodeoxygenation over a molybdenum carbide (Mo2C catalyst), which has been described previously ([0076]). The specification discloses the Co/Mn/Br-catalyzed autoxidative C-C cleavage of HDO lignin oil into benzoic, phthalic, isophthalic, and terephthalic acids ([0074]). Figure 1 of the drawings depicts exemplary compounds of the process. Notably, the HDO oil contains a variety of aromatic compounds that are subsequently cleaved during the oxidizing step. The compounds in the HDO oil do not contain any alcohol groups. Example 4 of the specification discloses genetically modified P. putida that converts benzoic acid, terephthalate, isophthalate and orthopthalate to muconolactone. The specification discloses optimizing the oxidation process conditions, including parameters such as temperature ([0079] and Fig. 11), O2 loading ([0080]), and concentrations of individual catalyst components ([0082] and Fig. 11), and residence time ([0083]).
To summarize, the specification discloses a single hydrodeoxygenation catalyst (Mo2C) and a single oxidation catalyst (5/5/0.5 wt% of Co(OAc)2•4H2O/Mn(OAc)2•4H2O/NaBr) capable of performing the claimed reaction sequence. There are no hydrodeoxygenation or oxidation conditions disclosed without a catalyst.
The specification does not show a structure-function correlation between the oxidation conditions and the plurality of oxygenated monomers capable of being bioconverted by genetically engineered P. putida into muconic acid. A single species of oxidation catalyst capable of oxygenating HDO oil into benzoic, phthalic, isophthalic, and terephthalic acids is disclosed.
Regarding the hydrodeoxygenation conditions, although the prior art teaches a variety of HDO conditions, the majority of conditions result in saturated cyclohexane derivatives rather than aromatics. For example, Kumar et al. (Catalysis Today 408 (2023): 182-193; published online 2022) teaches a process comprising RCF to produce a lignin bio-oil followed by catalytic hydrodeoxygenation (page 183, right column, paragraph 2). Kumar teaches a variety of HDO catalysts, including Pt/HY, Ru/TiO2, Pt/TiO2, Ru-NbOPO4, and Ni/Al2O3 ((page 183, right column, paragraph 2). However, the HDO oil (Figure 7a) comprises mostly cyclohexane derivatives rather than aromatics.
Yang et al. (ChemCatChem 14.16 (2022): e202200297) teaches the reductive catalytic fractionation of lignin (RCF) produces bioliquids comprising monomers with methoxy substituents (Abstract). Yang teaches valorizing these liquids through selective catalytic hydrodeoxygenation to obtain alkylated phenols (Abstract). Yang also teaches that 4-n-propylguaiacol is a major product in the bioliquids obtained from the reductive catalytic fractionation of lignin (page 10, 2.2.7 Catalytic experiments using 4-n-propylguaiacol). Yang teaches the conversion of 4-n-propylguaiacol over TiO2-supported MoO3 catalyst into demethoxylated phenolics like 2-n-propylphenol, 4-n-propylphenol, and methylated propylphenol (2-sec-tubylphenol and 4-sec-butylphenol), as well as the minor product propylbenzene (page 10, right column, bottom paragraph through top line in the left column on page 11). Therefore, Yang’s HDO oil contains primarily phenol derivatives, which retain both aromatic and alcohol groups.
In contrast to the above HDO catalysts, Chen et al. (Applied Catalysis A: General 510 (2016): 42-48) teaches the conditions for hydrodeoxygenation to aromatic compounds and the removal of alcohol groups. Chen teaches vapor phase hydrodeoxygenation (HDO) of phenolic compound mixtures containing m-cresol, anisole, 1,2-dimethoxybenzene, and guaiacol over molybdenum carbide catalysts (Mo2C) under atmospheric pressure at 533–553 K (Abstract). The catalyst has a much greater product selectivity for aromatics than cyclohexane compounds (Fig. 2).
Regarding the oxidation conditions taught by the prior art, Yuan et al. (Journal of Catalysis 339 (2016): 284-291) teaches the aerobic oxidation of methyl aromatic compounds using Co(CH3COO)2–Mn(CH3COO)2–KBr (Abstract). Yuan exemplifies the conversion of p-substituted toluene over a Co-Mn-Br catalyst to a substituted benzoic acid (Scheme 1).
Räisänen et al. (Catalysis Science & Technology 4.8 (2014): 2564-2573) teaches that oxidation of various alcohols with the homogeneous Mn(OAc)2/tBuOOH catalyst system (Table 1 on page 2566). Räisänen teaches that the catalyst catalyzes the conversion of benzyl alcohol to benzoic acid with 84% conversion and 80% selectivity to benzoic acid in 21 h (Table 1 footnote d).
The specification discloses the Co/Mn/Br-catalyzed autoxidative C-C cleavage of HDO lignin oil into benzoic, phthalic, isophthalic, and terephthalic acids ([0074]). Dong et al. (Journal of Catalysis 394 (2021): 94-103) teaches Caromatic-C bonds cleavage in lignin over NbOx-supported Ru catalyst (Title). However, Dong’s Caromatic-C bonds cleavage occurs in the presence of H2 (page 96, left column, 2.4 Catalytic test and product analysis) rather than oxygen and thus generates different products (see, for example Fig. 6 of Dong) than benzoic, phthalic, isophthalic, and terephthalic acids.
Wang et al. (Green Chemistry 19.3 (2017): 702-706) teaches an oxidative copper catalyst that promotes C–C bond oxidative cleavage of β-O-4 and β-1 lignin models to esters (Title). Although Wang teaches the cleavage of lignin-type molecules to products that include benzoic acid (see Table 1, product c), the majority of Wang’s oxidation conditions produce phenyls and esters rather than acids (see Table 2) due to the presence of BF3·OEt2, which catalyzes the esterification of acid with an alcohol solvent to an ester (page 705, right column, paragraph 1).
Wang 2016 et al. (ACS Catal., 2016, 6, 6086–6090) also teaches C-C bond oxidative cleavage to convert lignin models to aromatic acids (Title). Wang’s process requires two separate catalytic conversions: a two-step strategy for lignin C−C bond conversion via first, β-O-4 alcohol oxidation to ketone over the VOSO4/TEMPO catalyst, and second ketone oxidation over Cu(OAc)2/1,10-phenanthroline catalyst to acids and phenols (page 6089, left column, bottom paragraph).
Thus, although several different oxidizing catalysts are taught by the prior art, these catalysts were applied to lignin models rather than HDO oil. The structure of HDO oil is distinct from lignin itself (compare Fig. 7a of Kumar to Table 1 of Wang).
Regarding the genetically engineered P. putida, Salvachúa et al. (Green Chemistry 20.21 (2018): 5007-5019) teaches that converting lignin from biorefineries to muconic acid and then catalytically upgrading muconic acid to adipic acid is economically desirable (page 5007, right column, bottom paragraph). Salvachúa also teaches producing muconic acid from benzoate by engineered P. putida KT2400 (Fig. 1). Salvachúa presents in Fig. 1 an overview of metabolic pathways and genotype differences of muconic acid-producing strains of P. putida. However, the process of producing muconic acid requires benzoate or benzoic acid, ferulate, or p-coumarate as starting points (Fig. 1). Salvachúa teaches that benzoic acid is not a typical monomer released during lignin depolymerization (page 5008, left column, paragraph 1). Ferulate, or p-coumarate are released from alkaline biomass treatment methods (page 5009, left column, paragraph 1), which are distinct from the presently claimed RCF/HDO approach.
To summarize, the prior art does not teach any other HDO and oxidation conditions that allow the combination of RCF/HDO with bioconversion by genetically engineered P. putida to produce muconic acid. Although the person of ordinary skill in the art would have recognized the structural requirements in P. putida required for bioconverting benzoic acid into muconic acid (see Fig. 1 of Salvachúa), the claims are broader than this narrower embodiment disclosed by prior art. The person of ordinary skill in the art would have been unable to reasonably predict and visualize the structures of all the species of the claimed HDO and oxidation conditions that generate oxygenated monomers capable of being converted by genetically engineered P. putida into muconic acid.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to CANDICE LEE SWIFT whose telephone number is (571)272-0177. The examiner can normally be reached M-F 8:00 AM-4:30 PM (Eastern).
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Louise Humphrey can be reached at (571)272-5543. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/LOUISE W HUMPHREY/Supervisory Patent Examiner, Art Unit 1657
/CANDICE LEE SWIFT/Examiner, Art Unit 1657
Prosecution Insights