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
Claims 1-4, 6, and 8-21 are pending.
Claims 1, 3, 8, 14, and 16 are currently amended.
Claims 5 and 7 are cancelled.
Priority
This application is a 371 of PCT/IB2021/058572 which claims the benefit of IT 102020000022387 with an effective filing date of 23 September 2020 as reflected in the filing receipt mailed on 11 August 2023.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 26 November 2025 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement has been considered by the examiner.
Response to Amendments
Applicant’s amendments filed 17 April 2026 are acknowledged.
Claim Objections
Applicant’s amendment to claim 8 is sufficient to overcome the
objection of the claim. The claim has been amended to correct the typographical mistake. The objection is withdrawn.
Claim Rejections - 35 USC § 112
Applicant’s amendments to claims 8, 14, and 16 are sufficient to overcome the rejection of claims 8, 14, and 16 under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. The claims have been amended to correct the indefiniteness and lack of clarity in each claim. The rejections are withdrawn.
Claim Rejections - 35 USC § 103
Applicant’s amendments to claim 1 adding a list of specific solvents in step (a) not taught by Dumesic and a specific alkali halide in step (a) not taught by Dumesic and Cui, and the cancellation of claim 7 are sufficient to overcome the rejections of:
Claims 1-6 and 8-21 under 35 U.S.C. 103 as being unpatentable over Dumesic et al. (US20120302765, hereinafter Dumesic) in view of Cui et al. (“Conversion of carbohydrates to furfural via selective cleavage of the carbon–carbon bond: the cooperative effects of zeolite and solvent”, 2016, Green Chemistry, Vol. 18, Pgs. 1619-1624 and Supplementary Material, hereinafter Cui); and,
Claim 7 under 35 U.S.C. 103 as being unpatentable over Dumesic et al. (US20120302765, hereinafter Dumesic) in view of Cui et al. (“Conversion of carbohydrates to furfural via selective cleavage of the carbon–carbon bond: the cooperative effects of zeolite and solvent”, 2016, Green Chemistry, Vol. 18, Pgs. 1619-1624 and Supplementary Material, hereinafter Cui), as applied to claims 1-6 and 8-21 in the 35 USC 103 rejection above, in further view of Jansen et al. (US20170210721, hereinafter Jansen).
Due to the amendments to claim 1 and the cancellations of claims 5 and 7, new ground(s) of rejection is/are provided below.
Response to Arguments
Applicant’s arguments filed 17 April 2026 have been fully considered but they are moot or not persuasive.
Applicant’s argue that Dumesic, Cui, and Jansen do not disclose the limitations as recited in amended claim 1. These arguments have been considered but are either moot or not persuasive for the reasons set forth in the new grounds of rejection below and the response to arguments below.
Applicant’s arguments throughout the remarks filed on 17 April 2026 with respect to Dumesic have been considered but are moot because the new ground of rejection does not rely on Dumesic applied in the prior rejection of record for any teaching or matter specifically challenged in the argument. Specifically, the new ground of rejection does not rely on Dumesic to teach instant application claim 1 step (a).
Applicant’s arguments throughout the remarks filed on 17 April 2026 with respect to Jansen have been considered but are moot because the new ground of rejection does not rely on Jansen applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
In response to Applicant’s arguments on pages 7-8 of the remarks filed on 17 April 2026 that “Cui does not disclose or even suggest adding a halide salt, and even less so an iodide salt, to the aqueous reaction medium.” “One cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references”, see MPEP 2145 IV. The test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art, see In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981) and MPEP 2145.
In this case, Cui is not applied to teach adding a halide salt to the reaction medium.
For the reasons indicated above, applicant’s above arguments are not persuasive.
New and Previous Rejections Based on Amendments to the Claims in the reply filed on 17 April 2026
In the Spirit of Compact Prosecution
Throughout prosecution the examiner has attempted to identify all objections and clarity issues amongst the claims, applicant is advised that some objections and clarity issues may still remain. Going forward, the examiner respectfully requests applicant to perform a detailed review of the claims regarding clarity, grammar, antecedent basis, word spacing, and spelling issues.
For clarity between the new and previous rejections, the specific new rejections below are in italics.
Claims 1, 3, and 8-19 are newly rejected under 35 U.S.C. 103 as being unpatentable over Dumesic et al. (US20120302765, published 29 November 2012, hereinafter Dumesic) in view of Binder et al. (US20140235851, published 21 August 2014, hereinafter Binder).
Dumesic is in the known prior art of “a process to make furanic products (HMF, furfural) and any of their derivatives (furfuryl alcohol, LA, levulinate esters, GVL)” “in mono- or biphasic systems”, where “furfuryl alcohol may be converted into levulinic acid (through contact with an aqueous solution preferentially containing an acidic catalyst) or levulinate esters (through contact with an esterifying solvent such as alcohols or olefins)” by first “dehydrating a feedstock solution containing a carbohydrate, in the presence of an acid catalyst” to obtain furan derivatives “in the aqueous reaction solution” which “are continuously extracted into [an] organic extracting solvent” to produce the products, “such as furfural and hydroxymethylfurfural”, which are processed “to obtain other derivatives such as furfuryl alcohol, levulinic acid, levulinate esters, and/or GVL” aka γ-valerolactone, sees Para. [0014];[0017];[0028]; Fig. 7.
Regarding the limitations of instant application claims 1 and 8-19, Dumesic teaches a method for the selective dehydration of C5 and C6 carbohydrates, preferably xylose, fructose and glucose, to produce furfural and hydroxymethylfurfural and other furan derivatives, such as furfuryl alcohol, levulinic acid, levulinate esters, and/or gamma-valerolactone using organic solvent, see Para. [0013]. The process comprises the dehydration of xylose in aqueous solutions to obtain furfural by using mineral acids, such as HCl, HF, HBr, acetic acid, oxalic acid, sulfonic acid, trifluoroacetic acid, sulfated zirconia, zeolites, an organic extracting solvent, such as 2-sec-butylphenol (SBP), and a salt, such as NaCl, at a temperature of 170 °C, see Paras. [0013]-[0016];[0024];[0056];[0058]-[0060];[0068]-[0069];[0109]-[0112], Table 3, meeting:
The product produced in instant application claim 1;
The obtained furfural is then hydrogenated to obtain furfuryl alcohol by contacting the furfuryl with a hydrogen donor, such as various C3-C6 secondary alcohols including isopropanol (IPA), 2-butanol (2BuOH), and 2-hexanol (2HO), and a homogeneous or heterogeneous metal oxide catalyst, such as ZrO2, at 90 °C to 150 °C, see Paras. [0016];[0053]-[0056];[0077];[0116]-[0117], Table 4, meeting:
Step (b) in instant application claim 1;
Within the temperature range in instant application claim 11;
The specific Lewis acid of ZrO2 and the specific C3-C6 secondary alcohol protic solvents in instant application claim 9 and in instant application claim 10;
The specific Lewis acid and protic solvent reactants are the same as instantly claimed, see MPEP 2112.01; therefore, step (b) is carried out in a heterogeneous phase with the specific insoluble Lewis acid, meeting in instant application claim 8;
The furfuryl alcohol is converted to levulinic acid directly by reacting with mineral acids, such as “any mineral-containing acid, including (by way of example and not limitation), hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, boric acid, hydrofluoric acid, hydrobromic acid, and the like)”, i.e., hydrobromic acid is a Lewis acid and hydrochloric acid is a Bronsted-Lowry acid, and solid acid catalysts, such as acid zeolites or acid ion exchange resin Amberlyst-15, in a biphasic/heterogenous system that comprises an organic layer, furfuryl alcohol in extracting solvent, and an aqueous layer containing the acid catalyst, such as 1 M H2SO4, Amberlyst-15, or in a single layer/homogenous system with only organic solvent, both conducted at temperatures between 110 °C to 125 °C, see Paras. [0017];[0056];[0058]-[0060];[0118], Table 5, meeting:
Step (c) in instant application claim 1;
The aqueous acid catalysts conversion in instant application claim 12;
The Bronsted-Lowry acid, such as HCl and H2SO4, the Lewis acid hydrobromic acid, or acid zeolites and ion exchange resins in instant application claim 13 and in instant application claim 14;
Within the temperature range in instant application claim 15;
The furfuryl alcohol is converted to levulinic acid indirectly by first conversion to levulinic acid ester and further hydrolyzed to levulinic acid by mixing a primary alcohol with the furfuryl alcohol feed and reacted using a solid acid catalyst, such as acid zeolites or acid ion exchange resin Amberlyst-15, in an aqueous or non aqueous all organic solvent system at temperatures between 110 °C to 125 °C, see Para. [0058]-[0060];[0119], Table 5, meeting:
Steps (c1) and (c2) in instant application claim 16;
Steps (c1) and (c2) with or without water in instant application claim 17 and in instant application claim 18; and,
The acid catalysts and within the temperature range in instant application claim 19.
Dumesic does not teach:
The instant application claim 1 limitation of step (a); and,
The limitations of instant application claims 3, 6, and 20.
Binder is in the known prior art field of a “method for converting a carbohydrate to a furan in a polar aprotic solvent in the presence of a chloride, bromide, or iodide salt or a mixture thereof and optionally in the presence of an acid catalyst, a metal halide catalyst and/or an ionic liquid (up to 40 wt %)” “to produce furfural or 5-hydroxymethylfurfural” (HMF)), see Abstract, where “[a]queous acid and high temperatures and pressures (250-400° C., 10 MPa) enable conversion of cellulose into HMF and levulinic acid”, see Para. [0010], and is applied to teach the same.
Regarding the limitations of instant application claims 1, 3, 6, and 20, Binder teaches “a method for converting a carbohydrate to a furan in a polar aprotic solvent in the presence of a chloride, bromide, or iodide salt or a mixture thereof and optionally in the presence of an acid catalyst, a metal halide catalyst or an ionic liquid (up to 40 wt %)”, where “the furan is furfural”, see Para. [0014], “the carbohydrate is or comprises a 5-carbon sugar”, such as “arabinose, xylose, ribose or xylose”, see Para. [0020], the a polar aprotic solvent comprises dimethylsulfoxide, see Para. [0021], the carbohydrate is mixed in water, see Table 2 stating “glucose was 45% in water”, Para. [0006], “the catalyst is a Bronsted acid or a metal halide or a mixture of such catalysts”, such as the Bronsted acids “HCl, sulfuric acid, and nitric acid” and the Lewis acids “CrCl2, CrCl3, CrBr3 or mixtures thereof”, see Para. [0023], and “the iodide salt is NaI or KI”, see Para. [0022], meeting:
The step (a) converting a pentose into a furfural in the presence of an acid catalysts and an alkali metal halide in an organic solvent in instant application claim 1;
The reaction includes organic solvent and water in instant application claim 6;
The specific pentose arabinose or xylose in instant application claim 20;
The specific solvent dimethyl sulfoxide is a specifically instantly claimed solvent, see MPEP 2112.01; therefore, the specific solvent in step (a) is within the boiling point temperature range in instant application claim 1;
The specific metal halide in step (a) in instant application claim 1;
The Bronsted or Lewis acids in instant application claim 3; and,
“The carbohydrate conversion reaction is carried out at ambient pressure and at temperatures ranging from 50 to 200° C”, see Para. [0027], meeting within the temperature range of step (a) in instant application claim 1.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the carbohydrate dehydration to produce furfural of Dumesic to use the carbohydrate dehydration to produce furfural as taught by Binder with a reasonable predictability of success for the purpose of efficiently and economically converting “biomass, including lignocellulosic biomass, to useful fuels and chemicals”, such as the conversion of biomass “to HMF and furfural” then to levulinic acid, see Binder, Paras. [0010]-[0014].
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying the carbohydrate dehydration to produce furfural of Dumesic by applying the known technique of the carbohydrate dehydration to produce furfural as taught by Binder with a reasonable predictability of success for the purpose of efficiently and economically converting “biomass, including lignocellulosic biomass, to useful fuels and chemicals”, such as the conversion of biomass “to HMF and furfural” then to levulinic acid, see Binder, Paras. [0010]-[0014]; and MPEP 2143 I. B-D.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Dumesic and Binder both teach carbohydrate dehydration to produce furfural in the conversion of carbohydrates to useful chemicals and fuels industry, a person of ordinary skill in the art has good reason to modify Dumesic by relying upon Binder before the effective filing date of the claimed invention for knowledge generally available within the conversion of carbohydrates to useful chemicals and fuels art regarding the production of furfural, see MPEP 2143 B & G and 2141, for the benefit of efficiently and economically converting “biomass, including lignocellulosic biomass, to useful fuels and chemicals”, such as the conversion of biomass “to HMF and furfural” then to levulinic acid, see Binder, Paras. [0010]-[0014]; and, MPEP 2141 and 2143 I. B-D.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its actual application is beyond his or her skill”, see MPEP 2141.
In addition, “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions. In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929)”, see MPEP 2144.05.
Claims 2, 4, 6, and 21 are newly rejected under 35 U.S.C. 103 as being unpatentable over Dumesic et al. (US20120302765, published 29 November 2012, hereinafter Dumesic) in view of Binder et al. (US20140235851, published 21 August 2014, hereinafter Binder), as applied to claims 1, 3, and 8-19 in the 35 USC 103 rejection above, in further view of Cui et al. (“Conversion of carbohydrates to furfural via selective cleavage of the carbon–carbon bond: the cooperative effects of zeolite and solvent”, published 2016, Green Chemistry, Vol. 18, Pgs. 1619-1624 and Supplementary Material, hereinafter Cui).
Dumesic does not teach:
The limitations of instant application claims 2, 4, 6, and 21.
Cui is in the known prior art field of converting carbohydrates, such as “cellulose, starch, inulin, maltose, sucrose, glucose and fructose” “arabinose or xylose” “into furfural efficiently over Hβ zeolite in a γ-butyrolactone–water solvent”, see Abstract; Pg. 1622, Col. 1, Second Para; Table S7, and is applied to teach the same.
Regarding the limitations in instant application claims 2, 4, and 6, Cui teaches the conversion of carbohydrates to furfural and “levulinic acid (LA)” by reaction with “Brønsted acids (H2SO4 and Amberlyst-15), Lewis acids (AlCl3) or their combination (Amberlyst-15 + AlCl3)”, i.e., as stated in the instant specification Pg. 9, Ln. 29-Pg. 10, Ln. 5, “Amberlyst resin (acid sulphonic resin)” aka an organic acid, “over a series of acidic zeolites (HY, H-mordenite, HZSM-5 and Hβ)” in various solvents, such as “γ-butyrolactone (GBL)” in water or “1,4-dioxane” in water, see Pg. 1620, Results and discussion, Tables 1, 2, and S7, meeting:
The step (a) organic acid, acid zeolite, and solvent in water in instant application claim 2, in instant application claim 4, and in instant application claim 6.
Regarding the limitations in instant application claim 21, Cui teaches the production of furfural from hexose and the conversion of furfural to levulinic acid, see Abstract, Pg. 1620, Results and discussion, Table 1, teaches a C-C bond is removed from glucose and/or fructose by a catalytic reaction in contact with a zeolite acid catalysts, solvents, such as γ-valerolacatone (GVL) and γ-butyrolactone (GBL) which are not associated with the longer times and heating required for removal and separation, and Brønsted acids, such as H2SO4 and Amberlyst-15, Lewis acids, such as AlCl3, or their combination, to obtain arabinose which is converted in situ to furfural and levulinic acid, see Pg. 1620-Pg. 1621, Results and discussion, Table 1, meeting:
Step (a0) in instant application claim 21.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the carbohydrate dehydration to produce furfural, the solvent and starting feedstock carbohydrate of Dumesic to use the carbohydrate dehydration to produce furfural, the in situ derived arabinose to furfural and solvent as taught by Cui with a reasonable predictability of success for the purpose of efficiently producing a furfural with high yield by employing minimal process steps without the need for high temperature solvent evaporation separation, see Cui, Pg. 1620-Pg. 1621, Results and discussion, Tables 1-3.
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying the carbohydrate dehydration to produce furfural of Dumesic by applying the known technique of the carbohydrate dehydration to produce furfural over acid zeolite catalysts with organic acids and the desired water-organic solvent mixtures as taught by Cui with a reasonable predictability of success for the purpose of efficiently producing a furfural with high yield by employing minimal process steps without the need for high temperature solvent evaporation separation, see Cui, Pg. 1620-Pg. 1621, Results and discussion, Tables 1-3; and MPEP 2143 I. B-D.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Dumesic and Cui both teach carbohydrate dehydration to produce furfural in the conversion of carbohydrates to useful chemicals and fuels industry, a person of ordinary skill in the art has good reason to modify Dumesic by relying upon Cui before the effective filing date of the claimed invention for knowledge generally available within the conversion of carbohydrates to useful chemicals and fuels art regarding the production of furfural, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing a furfural with high yield by employing minimal process steps without the need for high temperature solvent evaporation separation, see Cui, Pg. 1620-Pg. 1621, Results and discussion, Tables 1-3; and, MPEP 2141 and 2143 I. B-D.
Selection of a known material, such as aqueous and organic solvents, zeolite acid catalysts, and organic acids, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
“It is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions. In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929)”, see MPEP 2144.05.
In addition, “[w]here applicant claims a composition in terms of a function, property or characteristic and the composition of the prior art is the same as that of the claim but the function is not explicitly disclosed by the reference, the examiner may make a rejection under both 35 U.S.C. 102 and 103.”, see MPEP 2112 III. In this case, when the starting feed of Dumesic is glucose or fructose, the in situ conversion to arabinose to furfural as instantly claimed will inherently also take place in the zeolite acid catalysts reaction taught by Dumesic, see MPEP 2112 and Dumesic, Paras. [0013]-[0015];[0055]-[0056];[0058]-[0060].
Conclusion
No claims are allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Y. Lynnette Kelly-O'Neill whose telephone number is (571) 270-3456. The examiner can normally be reached Tuesday-Friday, 8:30 a.m. - 6:30 p.m., EST, with Flex Time.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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