claytorDETAILED 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 .
Priority
This application is a 371 of PCT/IB2021/058572 which claims the benefit of IT 102020000022387 as reflected in the filing receipt mailed on 11 August 2023.
Information Disclosure Statement
The information disclosure statements (IDSs) submitted are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements have been considered by the examiner.
Claim Objections
Claim 8 is objected to because of the following informalities:
Claim 8, line 2 states “in heterogenous phase”, which appears to include a typographical mistake. Claim 8 is interpreted as “in a heterogenous phase”.
Appropriate correction is required.
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.
Claims 8, 14, and 16 are rejected 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.
Regarding claim 8, the phrase “i.e.” renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention, see MPEP § 2173.05(d).
Regarding claim 14, the phrase “for example” renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention, see MPEP § 2173.05(d).
Regarding claim 16, the parenthetical “(levulinic acid alkyl ester)” renders the claim indefinite because it is unclear whether the limitation within the parenthetical is part of the claimed invention, see MPEP § 2173.05(d).
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 1-6 and 8-21 are rejected 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).
Dumesic teaches the claims 1-4, 6, and 8-20 limitations of 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 and most of step (a) including within the temperature range of reaction in instant application claim 1;
The organic acid catalysts in instant application claim 2;
The Bronsted-Lowry inorganic acid, such as HCl, in instant application claim 3;
The acid catalysts is an acid zeolite in instant application claim 4;
The organic solvent is in admixture with water in instant application claim 6;
The specific pentose is xylose in instant application claim 20;
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, meeting in instant application claim 8;
The furfuryl alcohol is converted to levulinic acid directly by reacting with mineral acids, such as HCl and H2SO4, 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];[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, 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 (a) an organic solvent having a boiling temperature from 60°C to 220°C; and,
The limitations of instant application claims 5 and 21.
Dumesic teaches a method for the selective dehydration of C5 and C6 carbohydrates, preferably xylose, fructose and glucose, to produce furfural, see Para. [0013], all of the products of interest have lower boiling points than the AP solvent and thus can be recovered at a high purity via simple distillation without requiring solvent evaporation, and the boiling point of 2-sec-butylphenol (SBP) is 228 °C, see Paras. [0030];[0073]-[0074], Table 1.
Cui relating to 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:
The specific organic solvent in instant application claim 5;
The specific solvents include specifically instantly claimed solvents, see MPEP 2112.01; therefore, the solvent boiling points are within the temperature range in instant application claim 1; and,
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 solvent and starting feedstock carbohydrate of Dumesic to use 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.
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 both Dumesic and Cui teach solvents with boiling points higher than the product of interest, a person of ordinary skill in the art has good reason to produce a furfural by pursuing the known options within their technical grasp before the effective filing date of the claimed invention, such as choosing the starting feed and optimal extraction solvent, 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.
Selection of a known material, such as extracting solvents, 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.
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,” such as extraction solvents with the desired boiling points, “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.
Claim 7 is rejected 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).
Dumesic teaches yields to furfural in a single stage can be increased by saturating the aqueous acidic phase with salts, such as NaCl, which improves the partitioning of furfural into the extracting solvent, see Para. [0069].
Dumesic does not teach the instant application claim 7 limitation of wherein in step (a) the halide is an iodide.
Jansen relating to processes to produce furfural, comprising: (a) feeding a reactor with an aqueous sugar stream and an organic stream to form a biphasic reaction mixture; wherein the aqueous sugar stream comprises xylose, salt, and an acid, see Para. [0025], teaches the salt can be one that is selected from the group consisting of NaCl, NaBr, NaI, KCl, KBr, KI, CaCl2, FeCl3 and AlCl3, and the acid is a mineral acid catalyst, for example, H2SO4, HCl, etc., see Paras. [0116];[0121], meeting the iodide salt in instant application claim 7.
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 salt of Dumesic to use the iodine salt as taught by Jansen with a reasonable predictability of success for the purpose of efficiently producing a furfural with high yield by employing a salt that is compatible with the acid, see Jansen, Paras. [0026];[0045];[0121].
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 both Dumesic and Jansen teach the addition of halide salts, a person of ordinary skill in the art has good reason to produce a furfural by pursuing the known options within their technical grasp before the effective filing date of the claimed invention, such as using an iodide salt, for the benefit of efficiently producing a furfural with high yield by employing salt that is compatible with the acid, see Jansen, Paras. [0026];[0045];[0121] and MPEP 2141.
Selection of a known material, such as a iodide halide salt, 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.
Conclusion
No claims are allowed.
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/YO/Examiner, Art Unit 1692
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691