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 Claims
Claims 1-3, 6, 8-14, 16 have been amended pursuant to the amendment filed on 29 August 2024. Claims 1-18 are pending.
Priority
This application, filed on 29 August 2024, is a National Stage entry from International Application No. PCT/IL2023/050207, filed on 28 February 2023, which claims benefit under 35 U.S.C. 120 or 365 to US Provisional Application No. 63/315,220, filed on 1 March 2022.
Information Disclosure Statement
The information disclosure statement (IDS) filed on 18 January 2025 has been acknowledged and considered.
Specification Objections
Applicant is reminded of the proper language and format for an abstract of the disclosure. The abstract should be in narrative form and generally limited to a single paragraph on a separate sheet within the range of 50 to 150 words in length. The abstract should describe the disclosure sufficiently to assist readers in deciding whether there is a need for consulting the full patent text for details. The language should be clear and concise and should not repeat information given in the title. It should avoid using phrases which can be implied, such as, “The disclosure concerns,” “The disclosure defined by this invention,” “The disclosure describes,” etc. In addition, the form and legal phraseology often used in patent claims, such as “means,” “said,” and “comprising” should be avoided.
The words “comprising” and “said” are recited in the abstract. Appropriate correction is requested.
Claim Objections
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Claims 1 and 2 are objected to because there are no bonds indicating where the floating atoms are connected to in the formulas claimed (shown below).
Claims 11-14 and 16-18 are objected to because the term HMF is used but was not properly defined anywhere in the claims. While the definition is clear based on the specification, to avoid confusion, acronyms should be defined in the claims, at least in the first instance. Examiner recommends amending claim 1 in the claim set to include HMF in the parenthetical directly after where the first instance of 5-hydroxymethylfurfural appears in the preamble (i.e., “5-hydroxymethylfurfural (HMF)”) or in similar manner to how claim 2 defines AMF.
Appropriate correction is required.
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 10 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.
Regarding claim 10, a broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 10 recites the broad recitation “cooling the reaction mass”, and the claim also recites “preferably to room temperature” which is the narrower statement of the range/limitation. The claim is considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
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.
(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 1-4, 10, and 16-17 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by US20080200698 (“Reichert”).
Claim 1 is drawn to a process for preparing an ester of 5-hydroxymethylfurfural (HMF) comprising adding to a reaction vessel a C6 carbohydrate, an organic acid, and a salt which is at most sparingly soluble in said organic acid to form a reaction mass; heating the reaction mass, allowing the reaction to proceed, separating the salt from a liquid phase and recovering a reaction product comprising the ester of HMF. Claims 2-5 specify the acid as acetic acid, the C6 carbohydrate is a monosaccharide, fructose, or disaccharide, sucrose. Claim 6 specifies the salt selected from the group consisting of alkali metal halides, ammonium halides, metal bisulfates, ammonium bisulfate, ammonium sulfate, and monovalent, divalent, and trivalent metal sulfates and their hydrates, and mixtures consisting of two or more salts. Claim 10 is drawn to the process of recovering the reaction product by cooling the reaction mass, separating the salt from the liquid phase, to obtain a solution comprising a mixture of HMF and the ester of HMF, or the ester alone. Claim 16 is drawn to the process of isolating AMF from the mixture in of HMF and AMF. Claim 17 is drawn to a process of oxidizing, reducing, or hydrolyzing AMF.
Reichert teaches preparation of AMF using MgCl2 in Example 1A. The preparation process involves adding 0.6 mmol of D-fructose and 0.6 mmol of MgCl2·6H2O into a 2L three-neck flask with stirring and heated to 75°C for 30 min. The mixture was admixed with glacial acetic acid and heated to 90°-95°C for 4 hours. The acetic acid was distilled off, and the mixture was cooled to room temperature and 0.04 mmol of 4-(N,N-dimethylamino)pyridine was added. With stirring 6.5 mmol of acetic anhydride was added drop wise to the reaction mixture at 30°-40°C and the acetic anhydride was distilled off. The resulting reaction mixture was admixed with water, methyl isobutyl ketone and activated carbon. After filtration, through a pressure filter the organic phase and aqueous phase were separated and the organic phase was dried under reduced pressure provided AMF at 45% yield (¶ [0084]). Accordingly, claims 1-4, 10, and 16-17 are anticipated by Reichert.
Reichert also teaches a process of hydrolyzing AMF to HMF by dissolving AMF in methanol which is admixed with K2CO3 at 20°-25°C. After 1 h, the reaction mixture is admixed with 10g activated carbon stirred for 20 min and the solid constituents were filtered off and washed with methanol. The transparent methanolic solution was dried under reduced pressure and recrystallized using methyl tert-butyl ether to provide HMF at 73% yield (based on AMF starting material) (¶ [0086]). Accordingly claim 17 is anticipated by Reichert.
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.
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.
Claims 1-17 are rejected under 35 U.S.C. 103 as being unpatentable over Reichert in view of Zhao et al., RSC Adv., 2018, 8, 7235 (“Zhao”) further in view of Fang et al., ChemistrySelect 2018, 3, 12243– 12249 (“Fang”).
Reichert teaches preparation of AMF using MgCl2 in Example 1A. The preparation process involves adding 0.6 mmol of D-fructose (sucrose is also taught as a starting material (¶[0051])) and 0.6 mmol of MgCl2·6H2O into a 2L three-neck flask with stirring and heated to 75°C for 30 min. The reaction mixture was admixed with glacial acetic acid and heated to 90°-95°C for 4 hours. The acetic acid was distilled off, and the mixture was cooled to room temperature and 0.04 mmol of 4-(N,N-dimethylamino) pyridine was added. With stirring 6.5 mmol of acetic anhydride was added drop wise to the reaction mixture at 30°-40°C and the acetic anhydride was distilled off. The resulting reaction mixture was admixed with water, methyl isobutyl ketone and activated carbon. After filtration, through a pressure filter the organic phase and aqueous phase were separated and the organic phase was dried under reduced pressure provided AMF at 45% yield (¶ [0084]). The metal cations in the reaction are selected from alkali metal ions, alkaline earth metal ions, aluminum ions and mixtures thereof. The metal cations preferred are Mg2+, Ca2+, Na+, and Al3+ (¶[0055]) and it is assumed that the cation stabilizes the furanose form of the hexose which is believed to play an important role in the formation of the furan compound, in a sugar cation complex and hence catalyzes the dehydration (¶[0056]).
Reichert also teaches a process of hydrolyzing AMF to HMF by dissolving AMF in methanol which is admixed with K2CO3 at 20°-25°C. After 1 h, the reaction mixture is admixed with 10g activated carbon stirred for 20 min and the solid constituents were filtered off and washed with methanol. The transparent methanolic solution was dried under reduced pressure and recrystallized using methyl tert-butyl ether to provide HMF at 73% yield (based on AMF starting material) (¶[0086]).
Reichert does not teach the use of metal bisulfates as reagents nor does it explicitly teach the significance of promoting the equilibrium of a carbohydrate like fructose to its furanose form over its pyranose form.
Zhao teaches the influence of Lewis and Bronsted acids on the conversion of cellulose to HMF. AlCl3 and H3PO4 were chosen as the Lewis acid and Bronsted acid, respectively (p. 7235, Abstract). Zhao teaches as the AlCl3 – H3PO4 ratio increases the formation of furan products increases (Fig. 5). Zhao states: “This chemical family [furan products] was mainly generated by the dehydration reaction of furanose or the rearrangement of acyclic fragments coming from monosaccharide retroaldolization. In general, it was easy for furans to be formed in the presence of Lewis acid, whereas they presented a lower yield with Brønsted acid as the catalyst. It could be inferred that reaction conditions containing sufficient Lewis acid would promote the generation of furanose, and therefore the formation of furan products was greatly facilitated.” (p. 7240).
Zhao does not teach using metal bisulfates as reagents.
Fang teaches the conversion of cellulose to HMF using NaHSO4/ZrO2/H-2O-THF biphasic systems. Fang also teaches that in the co-catalytic system, H+ ions given from NaHSO4 was promotive to all steps of the cellulose to HMF conversion and abundant alkaline sites of ZrO2 was particularly favorable to the glucose to fructose isomerization (Abstract). Combining water and THF with NaSO4, as a salting out agent, and another co-catalyst namely ZrO2 was employed to catalyze the cellulose to HMF decomposition (p. 12244, 1st col.). Fang states: “NaHSO4 played an important role in promoting all steps of the cellulose-to-HMF conversion, through a salting-out effect and by catalysis of H+ ions…” (p. 12248, Conclusions).
Reichert, Zhang, and Fang are all analogous art because they are in the same field of using catalysts to stabilize the furanose form of a carbohydrate to make furan products. Therefore, it would have been prima facie obvious to a person having ordinary skill in the art (PHOSITA), before the effective filing date of the claimed invention, to follow the combined teachings of Reichert, Zhang, and Fang to arrive at the process instantly claimed. A PHOSITA would have found it obvious to react fructose or sucrose in acetic acid with an alkali metal halide, as taught by Reichert; leverage the alkali metal halide to stabilize the furanose form to specifically obtain furan products, as taught by Zhang; and substitute the metal halide with NaHSO4 to promote all steps of converting a saccharide to a furan product, as taught by Fang, to synthesize AMF. The combination of these prior art elements would have yielded reasonably predictable results because Fang teaches that NaHSO4 is a catalyst that promotes all steps of the cellulose to HMF conversion (MPEP §2143(A)). While the product formed is HMF, a PHOSITA would have been motivated to substitute a metal halide for a metal bisulfate like NaHSO4 because not only does it catalyze the reaction of a saccharide to a furan product, like AMF, but it also produces a salting out effect which encourages ease of isolation of said furan product because NaHSO4 promotes the solubility of the furan product in the organic phase (MPEP §2144.06(II)). Accordingly, claims 1-6, 8-9, 14-16 are prima facie obvious.
Regarding claim 7, Reichert teaches alkali metal ions, alkaline earth metal ions, aluminum ions and mixtures thereof can be used in step (a)(i) of the reaction and that suitable salts included are the chlorides, bromides, and fluorides. The explicit teachings of using the same salts in the process instantly claimed would have been prima facie obvious to a PHOSITA (MPEP §2143(G)).
Regarding claims 10-11, Reichert teaches that the temperature in step(a) of the reaction can be performed in a range from 80°-140°C (¶¶ [0053]-[0062]). The range overlaps with the ranges instantly claimed and are therefore prima facie obvious (MPEP §2144.05(I)).
Regarding claim 17, Reichert explicitly teaches hydrolysis of AMF to HMF (vide supra) and would therefore be prima facie obvious to a PHOSITA to follow (MPEP §2143(G)).
Claim 18 is rejected under 35 U.S.C. 103 as being unpatentable over Reichert in view of US 10,259,797 (“Gordillo”).
The teachings of Reichert are discussed above and are incorporated by reference herein.
Regarding claim 18, Reichert does not teach subsequent oxidation of HMF after hydrolysis of AMF to HMF.
Gordillo teaches a process for preparing furan-2,5-dicarboxylic acid by further processing a mixture containing 5-(hydroxymethyl)furfural and/or said one or more HMF esters. The steps comprising subjecting the mixture to oxidation conditions so that a product mixture results comprising furan-2,5-dicarboxylic acid and one or more carboxylic acids of formula (III) (wherein R1 is hydrogen or a substituted or unsubstituted, branched or linear, saturated or unsaturated or aromatic hydrocarbon radical
having a total number of 21 carbon atoms or less (Col. 6, lines 25-32)) (Col. 8, lines 33-49).
Reichert and Gordillo are both analogous art because they are in the same field of synthesizing AMF from fructose. Therefore, it would have been prima facie obvious to a PHOSITA to follow the combined teachings of Reichert and Gordillo to arrive at the process instantly claimed. A PHOSITA would have found it obvious to synthesize and isolate AMF and further hydrolyze it to make HMF, as taught by Reichert, and then subject the HMF to oxidation to form FDCA, as taught by Gordillo. The combination of these prior art elements would have yielded reasonably predictable results because a PHOSITA would have been motivated to purify the AMF prior to hydrolysis and the resulting HMF, as taught by Reichert, to ensure the product excludes impurities prior to oxidizing said HMF to synthesize FDCA as taught by Gordillo (MPEP §2143(A)).
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SAHIL CHANDER AGGARWAL whose telephone number is (571)272-7755. The examiner can normally be reached 7am-5pm.
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/SAHIL CHANDER AGGARWAL/Examiner, Art Unit 1623
/CLINTON A BROOKS/Supervisory Patent Examiner, Art Unit 1621
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