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 .
Non-Final Rejection
The Status of Claims:
Claims 1-20 are pending.
Claims 1-20 are rejected.
Claims 5-6 are objected.
DETAILED ACTION
1. Claims 1-20 are under consideration in this Office Action.
Priority
2. It is noted that this application is a 371 of PCT/US2021/054451 10/11/2021 PCT/US2021/054451 has PRO of 63090836 10/13/2020 .
Drawings
3. None.
IDS
4. The IDS filed on 4/12/23, 2/20/25 & 8/13/25 are reviewed by the examiner.
Claim Objections
Claims 5-6 are objected to because of the following informalities:
In claims 5-6, the expressions of parentheses in the terms “(e.g.,manganese oxide)”, “(e.g., sodium oxychloride)”, “ (e.g., sodium percarbonate)”, “(e.g., potassium permanganate)”, “(e.g., potassium perchlorate)”, “(e.g., potassium bromate)”, “(e.g., sodium periodate)”, (e.g.,potassium hydrogen monopersulfate, or Oxone®)”, “(e.g., hydrogen peroxide)”, and “(e.g., peracetic acid or meta-chloroperoxybenzoic acid)” and “Oxone®)” are recited. These parentheses can be confusing. The examiner recommends to remove them from the claims. 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.
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 5-6 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 pre-AIA the applicant regards as the invention.
In claim 5, the expressions “(e.g.,manganese oxide)”, “(e.g., sodium oxychloride)”, “ (e.g., sodium percarbonate)”, “(e.g., potassium permanganate)”, “(e.g., potassium perchlorate)”, “(e.g., potassium bromate)”, “(e.g., sodium periodate)”, (e.g.,potassium hydrogen monopersulfate, or Oxone®)”, “(e.g., hydrogen peroxide)”, and “(e.g., peracetic acid or meta-chloroperoxybenzoic acid) are recited. These expressions contain an abbreviation “e.g.”, which means "for example"; this phrase 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).
In claims 5-6, the expression “ Oxone®” is recited. This is vague end indefinite
because the source of this trademark is not disclosed in the specification. Thus, the examiner recommends to remove it from the claims.
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.
Claim 11 is rejected under 35 U.S.C. 112, first paragraph, because the specification, while being enabling for Co and Mn and nitric acid as the catalyst, does not reasonably provide enablement for any catalysts generally. The specification does not enable any skilled process chemist or pilot-plant operator to make the invention commensurate in scope with these claims. “The factors to be considered [in making an enablement rejection] have been summarized as the quantity of experimentation necessary, the amount of direction or guidance presented, the presence or absence of working examples, the nature of the invention, the state of the prior art, the relative skill of those in that art, the predictability or unpredictability of the art and the breadth of the claims”, In re Rainer, 146 USPQ 218 (1965); In re Colianni, 195 USPQ 150, Ex parte Formal, 230 USPQ 546. The three issues here are the lack of guidance in the specification, the limited working examples, and the unpredictability of the catalytic arts.
a) Determining if the a 6-carbon sugar unit substrate would react under Applicants conditions would require synthesis of the substrate and subjecting it to the oxidation with a variety of catalysts, a small quantity of experimentation. b) The direction concerning any acid catalyst is found in line 5, page 11. c) There is one working example of the " catalyst" Co and MN and /or nitric acid in lines 15-16, page 29. d) The nature of the invention is a chemical synthesis to make the 2,5-furandicarboxylic acid (FDCA) compound. This requires chemical catalysis. e) The state of the art is a patent (CN 109574962), which describes a method for preparing 2,5-furandicarboxylic acid from sugar in the presence of an acid catalyst comprises one or more of hydrochloric acid, phosphoric acid, sulfuric acid, ferric chloride, lead chloride, zinc chloride, manganese chloride, strontium chloride, bismuthchloride, cobalt chloride, cerium chloride, lanthanide chloride and actinide chloride and an oxidant.
f) The artisan using Applicants' invention to prepare the claimed compound would be a process chemist or pilot plant operator with a BS degree in chemistry and several years of experience. As suggested by Applicants in the parent application, he would know how to use the acid catalyst for oxidation reactions but be unaware of any other catalyst to use.
g) Chemical reactions are well-known to be unpredictable, In re Marzocchi, 169 USPQ 367, In re Fisher, 166 USPQ 18. Additionally, catalytic processes, such as are present here, are inherently unpredictable. The U.S. District Court District of Connecticut held in MOBIL OIL CORPORATION v. W.R. GRACE & COMPANY, 180 USPQ 418 that “there is an inherent mystery surrounding the unpredictability of the performance of catalysts; a mystery which is generally recognized and acknowledged by chemists in the cracking art. This is one more reason why the presumption of patent validity "should not be disregarded especially in a case of this sort where the intricate questions of [bio]chemistry involved are peculiarly within the particular competence of the experts of the Patent Office.” Merck & Co. v. Olin Mathieson Chemical Corp., 253 F.2d 156, 164, 116 USPQ 484, 490 (4th Cir. 1958)". "The catalytic action can not be forecast by its chemical composition, for such action is not understood and is not known except by actual test, Corona Cord Tire Co. v. Dovan Chemical Corp., 276 U.S. 358, 368-369 (1928). Also see, Application of Grant, 304 F.2d 676, 679, 134 USPQ 248, 250-251 (CCPA 1962); Rich Products Corp. v. Mitchell Foods, Inc., 357 F.2d 176, 181, 148 USPQ 522, 525-526 (2d Cir. 1966), cert. denied 385 U.S. 821, 151 USPQ 757 (1966); Ling-Temco-Vought, Inc. v. Kollsman Instrument Corp., 372 F.2d 263, 268, 152 USPQ 446, 450-451 (2d Cir. 1967); Georgia-Pacific Corp. v. United States Plywood Corp., 258 F.2d 124, 132-133, 118 USPQ 122, 128-129."
h) The breadth of the claims includes the presently unknown list of catalysts embraced by limitation "a catalyst". Thus, the breadth of the claim is moderate.
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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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.
5. Claims 1-20 are rejected under 35 U.S.C. 103 as being unpatentable over Howard et al (WO 2016/168233 A1) in view of Yao et al (CN109574962A).
Applicant claims the followings:
1. A process for pretreating a dehydration product of one or more carbohydrates having a 6-carbon sugar unit, the process comprising:in an oxidative pretreatment step, contacting the dehydration product with an oxidizing agent to provide a pretreated dehydration product having an improved property resulting from modifying humins present in the dehydration product,wherein a yield of 2,5-furandicarboxylic acid- (FDCA-) forming furanics in the pretreated dehydration product is at least about 80 mol-%.
2. The process of claim 1, wherein the improved property is a reduction in an absorption of ultraviolet or visible radiation, a reduction in color of downstream products, a decrease in average molecular weight of humins, an increase in a quantity of precipitated humins, or an increase in stability as an oxidation feed for producing FDCA.
3. The process of claim 2, wherein the improved property is the reduction in the absorption of light having a wavelength of 460 nanometers (nm).
4. The process of claim 3, wherein the absorption of light having a wavelength of 460 nm is about 60% or less, relative to that of the dehydration product.
5. The process of claim 1, wherein the oxidizing agent is a transition metal oxide (e.g.,manganese oxide), an alkali or alkaline earth metal oxyhalide (e.g., sodium oxychloride), an alkali or alkaline earth metal percarbonate (e.g., sodium percarbonate), an alkali or alkaline earth metal permanganate (e.g., potassium permanganate), an alkali or alkaline earth metal chlorate or perchlorate (e.g., potassium perchlorate), an alkali or alkaline earth metal bromate or perbromate (e.g., potassium bromate), an alkali or alkaline earth metal iodate or periodate (e.g., sodium periodate), an alkali or alkaline earth metal sulfate or persulfate (e.g.,potassium hydrogen monopersulfate, or Oxone®), a peroxide (e.g., hydrogen peroxide), a peroxy acid (e.g., peracetic acid or meta-chloroperoxybenzoic acid), or oxygen.
6. The process of claim 5, wherein the oxidizing agent is selected from the group consisting of MnO2, NaOCl,H202, KHSOs (Oxone®), Na2CO31.5H202, meta- chloroperoxybenzoic acid, peracetic acid, KMnO4, NaIO4, KBrO3, and combination thereof.
7. The process of claim 1, wherein the oxidizing agent is a bromine source.
8. The process of claim 1, wherein, in the oxidative pretreatment step, the oxidizing agent is present, or is added, in an amount representing from about 5 mol-% to about 70 mol-% of oxidizing equivalents, relative to FDCA-forming furanics in the dehydration product.
9. The process of claim 1, wherein, in the oxidative pretreatment step, an average residence time is at least 1 hour.
10. The process of claim 1, wherein, in the oxidative pretreatment step, an average temperature is from about 20°C to about 120°C.
11. The process of claim 1, wherein, in the oxidative pretreatment step, the dehydration product and the oxidizing agent are contacted in the presence of a catalyst.
12. The process of claim 11, wherein the catalyst comprises Co and/or Mn.
13. The process of claim 12, wherein the Co and/or Mn are independently present in an amount, or present in a combined amount, representing from about 0.1 mol-% to about 10 mol-% of FDCA-forming furanics in the dehydration product.
14. The process of claim 11, wherein the catalyst comprises an acid.
15. The process of claim 14, wherein the acid is present in an amount representing from about 0.05 mol-% to about 5 mol-% of FDCA-forming furanics in the dehydration product.
16. A process for making a monomer composition comprising 2,5-furan dicarboxylic acid (FDCA), the process comprising:in an oxidative pretreatment step, contacting a dehydration product of one or more carbohydrates having a 6-carbon sugar unit with an oxidizing agent to provide a pretreated dehydration product,in an oxidation step, contacting the pretreated dehydration product in the presence of oxygen, with an oxidation catalyst to provide the composition comprising FDCA, wherein, in the oxidation step, a yield of FDCA, based on FDCA-forming furanics in the pretreated dehydration product, is at least about 60 mol-%.
17. The process of claim 16, wherein an oxidative pretreatment temperature used in the oxidative pretreatment step is lower than an oxidation temperature used in the oxidation step.
18. The process of claim 17, wherein the oxidative pretreatment temperature is from about 20°C to about 120°C.
19. A process for making a monomer composition comprising 2,5-furan dicarboxylic acid (FDCA), the process comprising:in an oxidative pretreatment step, contacting a dehydration product of one or more carbohydrates having a 6-carbon sugar unit with an oxidizing agent to provide a pretreated dehydration product, in an oxidation step, contacting the pretreated dehydration product in the presence of oxygen, with an oxidation catalyst to provide the composition comprising FDCA,wherein an amount of the oxidizing agent that is added, or that is present, relative to FDCA-forming furanics in the dehydration product, is adjusted based on (i) a dry solids content of a dehydration feed that is subjected to a dehydrating step to obtain the dehydration product or (ii) a humin content of the dehydration product.
20. The process of claim 19, wherein the dry solids content of the dehydration feed is from about 5 wt-% to about 35 wt-%.
Determination of the scope and content of the prior art
Howard et al discloses that an integrated process for producing 2,5-furandicarboxylic acid and/or a derivative thereof from a six carbon sugar-containing feed, comprises: a) dehydrating a feed comprising a six-carbon sugar unit, in the presence of a bromine source as in claim 7 and of a solvent, at an elevated temperature from about 120 to about 250 degrees Celsius as in claims 10 and 18 (see page 21, a paragraph#0082) and for a time sufficient to generate an oxidation feed comprised of at least one of 5-hydroxymethylfurfural and/or a derivative or derivatives of 5 hydroxymethylfurfural in the solvent, together with at least one bromine containing species such as HBr as in claim 14(see page 8 , a paragraph#0030); b) contacting the oxidation feed from step (a) with a metal catalyst comprising either or both of Co and Mn as in claims 11-12 (see page 8, a paragraph #0027) and with an oxygen source at an elevated temperature for a time sufficient to produce an oxidation product mixture comprising 2,5-furandicarboxylic acid (FDCA) and/or a derivative thereof, the solvent, and a residual catalyst; c) purifying and separating the mixture obtained in step (b) to obtain FDCA and/or a derivative thereof and the solvent; and d) recycling at least a portion of the solvent obtained in step (c) to step (a) as in claim 16 (see abstract).
Also, Howard et al teaches that the six carbon sugar-containing feed comprises fructose and glucose etc. and the mole yield of the fructose and glucose conversions is a total average conversion of 96.2%, as in claim 1 (partially) with a standard deviation of 0.20% (see page 35, a paragraph #0124).
In addition, Howard discloses that the molar yield of 2,5-furandicarboxylic acid from the oxidation step on the basis of the FDCA-forming furanics in the oxidation feed is at least 60 percent as in claim 1 (partially)(see page 22, a paragraph#0083; page 40, table 4).
The current invention, however, differs from the prior art in that the claimed pretreated dehydration product having an improved property resulting from modifying humins present in the dehydration product, the improved property being a reduction in an absorption of ultraviolet or visible radiation having a wavelength of 460 nanometers (nm), an average residence time in the oxidative pretreatment step, an amount of the Co and/or Mn, an oxidative pretreatment temperature being lower than the oxidation temperature, an oxidizing agent being hydrogen peroxide and dry solids contents of the dehydration feed are unspecified in the prior art.
Yao et al discloses a method for preparing 2,5-furandicarboxylic acid (FDCA) from sugar. The method specifically includes converting hexacarbon saccharide as a raw material into 5-hydroxymethylfurfural (5-HMF) through a reaction in a tetramethylurea solvent in the presence of an acid as a catalyst, and an oxidant selected from hydrogen peroxide, oxygen, air, ozone, peroxide, and hypohalite (see page , converting the 5-HMF into the FDCA through a reaction, at reaction time from 1-24 hours as in claim 9 (see page 6, paragraphs# 0017-0018) and at 50-2200 C (see page 8 a paragprah#0025).
Ascertainment of the difference between the prior art and the claims
1. The difference between the application and the applied art is that the
applied art do not expressly teach the claimed pretreated dehydration product having an improved property resulting from modifying humins present in the dehydration product, the improved property being a reduction in an absorption of ultraviolet or visible radiation having a wavelength of 460 nanometers (nm), an amount of the Co and/or Mn, an oxidative pretreatment temperature being lower than the oxidation temperature, and dry solids contents of the dehydration feed.
The difference between the application and the applied Howard art is that the Howard does not expressly teach the claimed pretreated dehydration product having an improved property resulting from modifying humins present in the dehydration product, the improved property being a reduction in an absorption of ultraviolet or visible radiation having a wavelength of 460 nanometers (nm), an average residence time in the oxidative pretreatment step, an amount of the Co and/or Mn, an oxidative pretreatment temperature being lower than the oxidation temperature, an oxidizing agent being hydrogen peroxide and dry solids contents of the dehydration feed. The deficiencies of the Howard art is partially cured by the Yao et al.
The difference between the application and the applied Yao et al art is that the Yao et al does not expressly teach the claimed pretreated dehydration product having an improved property resulting from modifying humins present in the dehydration product, the improved property being a reduction in an absorption of ultraviolet or visible radiation having a wavelength of 460 nanometers (nm), an amount of the Co and/or Mn, an oxidative pretreatment temperature being lower than the oxidation temperature, and dry solids contents of the dehydration feed. The deficiencies of the Yao et al art are partially cured by the Howard.
Resolving the level of ordinary skill in the pertinent art.
Regarding the Claims 1-2 with respect to the lack of disclosing the pretreated dehydration product having an improved property resulting from modifying humins present in the dehydration product and the increase in stability as an oxidation feed for producing FDCA, From the Howard reference, the different feature can be easily considering that the use of the same acetic acid or acetic acid and water solvent in the dehydration and oxidation steps enables the use of the more stable 5-(acetoxymethyl)furfural (AcMF) precursor to FDCA (see page 23, a paragraph #0089). Also, extraction of the crude oxidation feed liquid was used to minimize precipitation of humins in the water phase (see page 32, a paragrepah#00116). Thus, the prior art is relevant to the claimed invention.
Regarding the Claims 3-4 with respect to the lack of disclosing the improved property being a reduction in an absorption of ultraviolet or visible radiation having a wavelength of 460 nanometers (nm) being 60 % or less relative to that of the dehydration product, the prior art are silent about them. However, these features can be easily derived from Howard by measuring the absorption of the light of the desired FDCA product relative to that of the dehydration product by a routine practice without difficulty and the effect of it would be predictable.
Regarding claims 8 and 15, Howard odes mention that the concentration of the HBr relative to fructose and glucose was kept constant at 1.99% mol based on HPLC analysis of the feed (see page 33, a paragraph#0120). Although there is a little difference between the claimed mole% and prior art mole %concentration of the oxidizing agent, the limitation of a process claim with respect to the mole % does not impart patentability to the process when such a value is one of those which could be adjusted by one of ordinary skill in the field of a chemical art in achieving optimum condition for the reaction process. This is because the skilled artisan in the art would expect such a manipulation to be within the purview of the skilled artisan in the art.
Regarding Claim 13 with respect to the lack of disclosing the amount of the Co and/or Mn, this is a merely variation of Howard process and a person skilled in the art would arrive at the claimed inventions by general experimentation alone without exercising any ingenuity, especially since the resulting advantages are readily foreseeable.
Regarding Claims 17 and 20 with respect to the lack of the oxidative pretreatment temperature which is lower than the oxidation temperature; the dry solids contents of the dehydration feed, the prior art silent about them . However, they are merely variations of the Howard process and a person skilled in the art would arrive at the claimed inventions by general experimentation alone without exercising any ingenuity, especially since the resulting advantages are readily foreseeable.
Considering objective evidence present in the application indicating obviousness or nonobviousness.
Howard et al expressly discloses that the integrated process for producing 2,5-furandicarboxylic acid from a six carbon sugar-containing feed by the steps: a) dehydrating a feed comprising a six-carbon sugar unit, in the presence of a bromine source and the solvent, at an elevated temperature and for a time sufficient to generate an oxidation feed comprised of at least one of 5-hydroxymethylfurfural and/or a derivative or derivatives of 5 hydroxymethylfurfural in the solvent, together with at least one bromine containing species and b) contacting the oxidation feed from step (a) with the metal catalyst comprising either or both of Co and Mn and with an oxygen source at the elevated temperature for a time sufficient to produce an oxidation product mixture comprising 2,5-furandicarboxylic acid (FDCA) and/or a derivative thereof.
Similarly, Yao et al does teach the method for preparing 2,5-furandicarboxylic acid (FDCA) from converting a hexacarbon saccharide as a raw material into 5-hydroxymethylfurfural (5-HMF) through a reaction in the presence of an acid catalyst, and hydrogen peroxide as an oxidant, at the reaction time from 1-24 hours.
Both processes are commonly involved in the production of FDCA from a 6 carbon sugar unit in the presence of the acid catalyst by a way of the dehydration of fructose. Furthermore, Yao et al does giver guidance that hydrogen peroxide as an oxidizing agent can be added to the process of forming FDCA to promote the overall process efficiently.
So, it would have been obvious to the skilled artisan in the art before the effective filing date of the claimed invention to be motivated to incorporate Yao’s hydrogen peroxide as an oxidizing agent into the Howard process in order to enhance the overall reaction process efficiently. This is because the skilled artisan in the art would expect the combined processes to be successful and feasible as guidance shown in the prior art.
Conclusion
Claims 1-20 are rejected.
Claims 5-6 are objected.
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/TAYLOR V OH/Primary Examiner, Art Unit 1625 12/12/2025