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 .
Claim Status
Claims 1-15 were filed on 2/29/2024. In a preliminary amendment filed on the same day, claims 1-15were canceled and claims 16-33 were newly added. Claims 16-33 are pending.
Priority
The application was filed on 2/29/2024 and claims the benefit of priority to:
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See filing receipt dated 8/5/2024. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Drawings
The drawings are objected to because where only a single view is used in an application to illustrate the claimed invention, it must not be numbered and the abbreviation "FIG." must not appear. See 37 CFR 1.84(u)(1).
Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Claim Rejections - 35 USC § 112(b)
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 29-31 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.
Claim 29 is rejected because it requires that the muconic compound has a formula (IA). Formula (IA) is not included in claim 16, from which claim 29 depends. Therefore, the limitation is indefinite. This formula is not introduced until claim 17. Claims 30 and 31 are rejected for depending from a rejected claim and failing to cure the deficiency.
Allowable Subject Matter
Claims 16-28, 32, and 33 are allowed and claims 29-31 are also free from the prior art.
The following is a statement of reasons for the indication of allowable subject matter: Frost (US 2011/0282078, published on 11/17/2011, of record in the IDS filed on 4/11/2024) and Tessonnier (US 2017/0129839, published on 5/11/2017, of record in the IDS filed on 4/11/2024) are the closest prior art.
Frost teaches cyclohexenes having carboxylate derivatives at the 1 and 4, and optionally the 2, position. The invention also relates to processes for preparing such compounds wherein a portion of the starting materials utilized is derived from renewable resources. See abstract and claims. Frost teaches the following Example 4 in [0066]:
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. Frost teaches that when cis, cis muconic acid, a compound of formula (IA) in instant claim 17 wherein all variables are H, is heated to reflux for 15 minutes in water, a polar protic solvent, that the major product is cis, trans-muconic acid the isomer of cis,cis-muconic acid. When the cis,trans-muconic acid is precipitated from the aqueous reaction mixture, the mother liquor was collected and concentrated to provide a mixture of 3% of the total muconic acid remained in solution as the cis-trans isomer, 25% of internal lactone (muconolactone-compound of formula (IB) in claim 17, wherein all variables are H), and 3% lactone-hydrolysis to provide levulinic acid.
Tessonnier teaches the isomerization of muconic acid. See abstract. Tessonnier teaches that cis,cis-muconic acid (ccMA) was isomerized to cis,trans-muconic acid within 20 minutes at 83°C in water to produce muconolactone (Mlac) and the corresponding dilactone (compound of formula (IC) in claim 17 wherein all variables are H):
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. See [0083-0085]. Tessonnier teaches that when catalysts and non-protic polar solvents are used, that the reaction could be influenced to produce trans,trans-muconic acid. See [0091-0118].
Neither Frost nor Tessonnier teach or suggest that muconic acid, or a lactone thereof, can be reacted under the instantly claimed conditions (protic polar solvent at a temperature greater than or equal to about 120°C at a pressure greater than or equal to autogenic pressure) to produce levulinic acid in any desirable quantity. Levulinic acid is only produced as a minor by-product in Frost and is not mentioned at all in Tessonier. Therefore, there would also be no motivation or reasonable expectation of success of modifying the prior art processes to arrive at that claimed. The examples in the specification further teach that levulinic acid can be produced in high yields and selectivity under the claimed conditions. Therefore, the claimed process is free from the prior art.
Reference is also made to Ver Elst (“Synthesis of Levulinic Acids from Muconic Acids in Hot Water”, Angew. Chem. Int.Ed. 2023, e202309597). The reference is an NPL authored by the inventors which does not qualify as prior art and teaches the claimed process. There is no indication that the claimed invention was known before being disclosed by the inventors.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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