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 .
Priority
This application claims the benefit of US Provisional Application 63/442,532 with an effective filing date of 01 February 2023 as reflected in the filing receipt mailed on 02 April 2024.
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.
Specification
Abstract
The abstract of the disclosure is objected to because line 4 contains the undefined acronym “HTO”. As per page 5, line 3 of the instant specification, line 4 of the abstract is interpreted to state “disclosure is required and must be presented on a separate sheet, apart from any other text, see MPEP § 608.01(b).
Claim Objections
Claims 1, 9, 11, 19, and 21 are objected to because of the following informalities:
The claims appear to incorporate grammatical mistakes:
Claim 1, lines 8-9 state “in hydrogen environment” instead of “in a hydrogen environment”;
Claim 1, lines 9-10 state “to complete conversion of” instead of “to complete the conversion of”;
Claim 9, line 3 states “amino moiety and having fewer carbon atoms” instead of “amino moiety
Claim 11, lines 1-2 state “is monosaccharide” instead of “is a monosaccharide”.
Claim 19, line 1 states “wherein amino alcohol precursor” instead of “wherein the amino alcohol precursor”;
Claim 19, lines 2-3 state “amino moiety and having fewer carbon atoms” instead of “amino moiety
Claim 21, lines 2-3 state “in hydrogen environment” instead of “in a hydrogen environment”.
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 1-24 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.
If the language of the claim is such that a person of ordinary skill in the art could not interpret the metes and bounds of the claim so as to understand how to avoid infringement, a rejection of the claim under 35 USC 112(b) is appropriate, see MPEP 2173.02.
Claims 1 and 13 state general “hydrogenation-active species”.
Claims 6 and 16 state general “doping elements”.
It is well known within the catalytic art that there are a vast amount of categories of metallic, non-metallic, organic, non-organic, and inorganic “hydrogenation-active species” and “doping elements”. It is not clear within the art as to which category of “hydrogenation-active species” and “doping elements” the claims refer. Therefore, the interpretation of the metes and bounds of the claim language so as to understand how to avoid infringement is unclear to a person of ordinary skill in the art.
The instant specification appears to define “hydrogenation-active species” and “doping elements” as “Ni-loaded HT Cu-loaded HT, Ru-loaded HT and other metal-loaded HT”, see Pg. 3, Last Para.-Pg. 4, Ln. 1; Pg. 6, Last Para.-Pg. 7, Ln. 12. Herein, the “hydrogenation-active species” and “doping elements” are interpreted as metals.
Claims 2-12 and 14-24 depend from base claim 1 or base claim 13 and are included in this rejection as they do not correct the above informalities identified in base claim 1 or base claim 13.
Claims 1-8 and 10-12 are rejected under 35 U.S.C. 112(b) as being incomplete for omitting essential steps, such omission amounting to a gap between the steps, see MPEP § 2172.01. The omitted steps are:
Claim 1 states “[a] method for conversion of β-hydroxy carbonyl species …” without stating a step as to what compound the β-hydroxy carbonyl species is converted; therefore, the method of claim 1 is incomplete. Herein, claim 1 is interpreted to incorporate the step of claim 9 stating “the conversion of the β-hydroxy carbonyl species produces an alcohol compound containing an N-acyl-substituted amino moiety
Claims 2-8 and 10-12 depend from base claim 1 and are included in this rejection as they do not correct the above informalities identified in base claim 1.
In the Spirit of Compact Prosecution
While 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.
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 1-24 are rejected under 35 U.S.C. 103 as being unpatentable over Zheng et al. (“Towards the Efficient Catalytic Valorization of Chitin to N-Acylethanolamine over Ni/CeO2 Catalyst: Exploring the Shape-Selective Reactivity”, published 20 April 2022, Catalysts, Vol. 12, No. 460, Pgs. 1-14 and Supplementary Materials, hereinafter Zheng) in view of Beckham et al. (US20140107381, published 17 April 2014, hereinafter Beckham).
Zheng is in the known prior art field of the “fully compatible with the concept of the United Nations’ Circular Carbon Economy” “catalytic valorization of chitin to N-acylethanolamine over cost-effective Ni/CeO2-based materials”, where “[i]n the quest to find a more benign reaction condition using a cheaper heterogeneous catalyst”, “marine/food-waste derived chitin, the only nitrogen-containing sustainable biomass, contain[ing] the unique N-acetylglucosamine units, [are] synthetically manipulated to a plethora of organonitrogen chemicals”, see Abstract; Pgs. 1-3, 1. Introduction; Fig. 1, with or without the need of an added base, such as NaHCO3, and expensive precious metals, such as ruthenium, see Table S2; Pg. 7, 2.2. Catalysis: Chitin Valorization; Pgs. 1-3, 1. Introduction, where the pace of the degradation/valorization of chitin Pathway A retro-aldol reaction then hydrogenation as compared to the Pathway B hydrogenation reaction is determined based upon the composition of the nickel oxide catalyst, see Pgs. 8-10, 2.3. Catalysis: Reaction Mechanism and Scheme 1.
Regarding the limitations of instant application claims 1-4, 8, 10, 11, 13, 14, 18, 20, and 23, Zheng teaches a method of the catalytic conversion of a beta-hydroxy carbonyl species aka an amino monosaccharide, such as N-acetylglucosamine (NAG), to N-acylethanolamine “over cost-effective Ni/CeO2-based materials”, see Abstract; Fig. 1; Pgs. 7-10, 2.2. Catalysis: Chitin Valorization – 2.3. Catalysis: Reaction Mechanism; Fig. 6; Pg. 9, Scheme 1., meeting:
The conversion of beta-hydroxy carbonyl species containing a nitrogen-group at the C alpha position of specifically N-acetylglucosamine in instant application claim 1, in instant application claim 2, in instant application claim 3, and in instant application claim 4;
The monosaccharide derivative specifically N-acetylglucosamine in instant application claim 10 and in instant application claim 11;
The amino saccharide specifically N-acetylglucosamine in instant application claim 13, in instant application claim 14, in instant application claim 20, and in instant application claim 23;
The amino alcohol precursor specifically N-acylethanolamine in instant application claim 13 and in instant application claim 23;
The reaction takes place by placing “NAG (66.1 mg, 0.3 mmol), the catalytic material (e.g., 10 wt% Ni/CeO2 catalyst, 15 mg), magnetic stirrer, NaHCO3 (25.2 mg, 0.3 mmol), and distilled water (5 mL)” “into a 20 mL glass reaction tube, and then inserted into a high-pressure batch reactor … Next, the batch reactor was subjected to 4 MPa H2, and heated to 393 K. The reaction was carried out for an appropriate time”, see Pgs. 11-12, 3.5. Catalytic Tests, where “[d]uring the degradation under hydrogen pressure, NAG initially undergoes a retro-aldol condensation reaction to produce 2-acetamidoacetaldehyde and erythrose … the former is then hydrogenated to N-acetylethanolamine (I) over a Ni catalyst … (Pathway A in Scheme 1) … The formation of ADS indicated the direct transformation of the NAG route (Pathway B in Scheme 1), followed by C–C bond cleavage to give our desired product, N-acetylethanolamine (I)” and the pace of the degradation/valorization of chitin Pathway A retro-aldol reaction then hydrogenation as compared to the Pathway B hydrogenation reaction is determined based upon the composition of the nickel oxide catalyst, see Pgs. 8-10, 2.3. Catalysis: Reaction Mechanism and Scheme 1. As indicated in Scheme 1, NAG is transformed over Ni/CeO2 catalysts by retro-aldol reaction then hydrogenation to N-acetylethanolamine in Pathway A, Pg. 9, Scheme 1, meeting:
The mixing NAG with a composite catalyst, such as Ni/CeO2, and catalyzing to perform retro-aldol then hydrogenation reactions in an H2 environment to complete the conversion of NAG to N-acetylethanolamine in instant application claim 1 and in instant application claim 13; and,
The composite catalyst is composed of nickel as the hydrogen-active species and CeO2 as the oxide, see Pgs. 8-10, 2.3. Catalysis: Reaction Mechanism and Scheme 1., where the “Ni/CeO2 catalysts were prepared by the wet impregnation method … Typically, 0.1781 g Ni(NO3)2·6H2O was dissolved in 0.5 mL deionized water and then 0.3594 g CeO2 nanocrystals were added”, see Pg. 10, 3.2. Synthesis of CeO2 Supports-3.3. Synthesis of Ni/CeO2 Catalysts, and nickel nanoparticles are present on the CeO2 support by “[g]reen circles indicat[ing] the plausible position of metallic Ni on catalytic materials”, see Figs. 4, 5, S1, and S6, meeting:
The nickel nanoparticle hydrogen active species on the surface of the oxide support in instant application claim 1, in instant application claim 8, in instant application claim 13, and in instant application claim 18.
Regarding the limitations of instant application claims 9 and 19, Zheng teaches, as stated above, a method of the catalytic conversion of a beta-hydroxy carbonyl species aka an amino monosaccharide, such as N-acetylglucosamine (NAG), to N-acylethanolamine “over cost-effective Ni/CeO2-based materials”, see Abstract; Fig. 1; Pgs. 7-10, 2.2. Catalysis: Chitin Valorization – 2.3. Catalysis: Reaction Mechanism; Fig. 6; Pg. 9, Scheme 1., i.e., NAG
PNG
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256
308
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with 8 carbon atoms is converted to N-acylethanolamine
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202
352
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with 4 carbon atoms, meeting:
The beta-hydroxy species converted to an N-acyl-substituted amino alcohol with fewer carbon atoms in instant application claim 9; and,
The amino alcohol precursor having an N-acyl-substituted amino alcohol with fewer carbon atoms than the amino saccharide in instant application claim 19.
Regarding the limitations of instant application claims 12 and 21, Zheng teaches, as stated above, “the batch reactor was subjected to 4 MPa H2, and heated to 393 K” or 119.85 C, see Pgs. 11-12, 3.5. Catalytic Tests; Tables S1-S2, meeting within the temperature range in a hydrogen environment in instant application claim 12 and in instant application claim 21.
Regarding the limitations of instant application claim 24, Zheng teaches the “catalytic valorization of chitin to N-acylethanolamine over cost-effective Ni/CeO2-based materials”, see Abstract; Fig. 1, where “chitins are constructed by NAG units, which could be utilized as feedstock to produce organonitrogen compounds. Among them, 2-acetamido-2-deoxysorbitol (ADS) and N-acylethanolamine (AMEA) are the two potential target molecules from chitin”, see Pg. 2, Last Para., and the reaction uses “valorization of chitin-derived molecules”, such as NAG, by “the valorization or degradation of chitin” containing biomass, see Abstract; Pgs. 8-10, 2.3. Catalysis: Reaction Mechanism, meeting:
The providing the amino saccharide by depolymerizing chitin biomass in instant application claim 24.
Zheng does not teach:
The instant application claim 1 limitations of a composite catalyst derived from layered double hydroxides (LDHs), wherein the composite catalyst includes a basic LDHs-derived mixed oxide support and hydrogenation-active species on the basic LDHs-derived mixed oxide support;
The instant application claim 13 limitations of a composite catalyst derived from layered double hydroxides (LDHs), wherein the composite catalyst includes a basic LDHs-derived mixed oxide support and hydrogenation-active species on the basic LDHs-derived mixed oxide support; and,
The limitations of instant application claims 5, 6, 7, 15, 16, and 17.
Beckham is in the known prior art field of “methods for degrading lignin by contacting the lignin with a layered double hydroxide (LDH) catalyst”, see Para. [0007], where “the LDH catalysts are very active in the cleavage of a β-O-4 linkage in a lignin model compound as well as for the depolymerization of biomass-derived lignin”, see Para. [0034]; Fig. 2, for converting the biomass to alcohols, “hydrocarbons, or other advanced fuels”, see Paras. [0039]-[0042]; Fig. 2, and the “solid base catalysts avoid the cost of liquid-phase, non-recyclable base, and downstream processing steps such as neutralization”, see Paras. [0004];[0025].
Regarding the limitations of instant application claims 1 and 13, Beckham teaches “the LDH catalyst comprises a solid base support combined with nickel. The solid base support may be hydrotalcite (HTC), and the amount of nickel combined with the hydrotalcite may be between 1 wt % Ni/HTC and 25 wt % Ni/HTC or between 5 wt % Ni/HTC and 15 wt % Ni/HTC” “for degrading lignin by contacting the lignin with [the] layered double hydroxide (LDH) catalyst in the presence of water or an organic solvent, wherein the LDH catalyst comprises hydrotalcite impregnated with nickel”, see Paras. [0008];[0011]-[0012], where the “[h]ydrotalcite (HTC), Mg6Al2(OH)16(CO3).4H2O, represents a specific example of LDH that exhibits a well-defined structure”, see Para. [0027]; Fig. 1, and “the oxidized nickel on a solid-basic support can function as an effective lignin depolymerization catalyst and demonstrates that layered double hydroxides offer a novel, active support in multifunctional catalyst applications”, see Para. [0030], meeting:
The basic LDH composite mixed-oxide support with nickel hydrogenation-active species impregnated on the support in instant application claim 1 and in instant application claim 13.
Regarding the limitations of instant application claims 5, 7, 15, and 17, Beckham teaches the “LDH catalysts typically comprise a divalent metal ion component for which a water-soluble salt exists. Examples include chlorides or nitrates of first row transition metals. Specific suitable examples include magnesium (Mg), nickel (Ni), iron (Fe), cobalt (Co), copper (Cu), zinc (Zn), calcium (Ca), tin (Sn) and lead (Pb)”, and the “LDH catalysts typically also comprise a trivalent metal ion component that is present in a particular ratio in relation to the divalent cation. Suitable examples include aluminum (Al), scandium (Sc), gallium (Ga), or indium (In).”, where the “layered double hydroxide, such as hydrotalcite (HTC),” “Mg6Al2(OH)16(CO3).4H2O”, is “used as a support material to harbor hydroxide anions in the brucite-like layers, which may participate as a catalytic species … An exemplary catalyst is a 5 wt % Ni/HTC catalyst, which is particularly effective at C—O bond cleavage”, see Paras. [0027]-[0031]; Fig. 1, meeting:
The LDH are doped M3+/N2+−LDHs, with M3+ trivalent metal, such as Al3+, and N2+ bivalent metal, such as Mg2+, in instant application claim 5, in instant application claim 7, in instant application claim 15, and in instant application claim 17.
Regarding the limitations of instant application claims 6 and 16, Beckham teaches doping agents, such as nickel, are combined with the solid base support, such as HTC “Mg6Al2(OH)16(CO3).4H2O”, in “metal percentages by weight range from about 1 wt % to 50 wt %, such as about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 15, 16, 17, 18, 19, 20, 25, 30, 35, 40, 45 or 50 wt %, as well as values between these integers … nickel may be combined with the hydrotalcite in amounts between 1 wt % Ni/HTC and 25 wt % Ni/HTC or between 5 wt % Ni/HTC and 15 wt % Ni/HTC” and the “ratio of the divalent component” such as Mg, “to the trivalent component”, such as Al, “can vary from 1:1 to 10:1, such as 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1 or any fractional value within these ranges” see Paras. [0027]-[0031]; Table 3, for example, where “5 wt % Ni/HTC gave Al 10.46 wt. %, Mg 17.36 wt. %, and Ni 4.44 wt. %”, see Paras. [0046]-[0050], meeting:
Within the weight percent which relates to and within the molar quantity of doping element Ni and Mg to Al in instant application claim 6 and in instant application claim 16.
Regarding the limitations of instant application claim 22, Zheng teaches a method of the catalytic conversion of a beta-hydroxy carbonyl species aka an amino monosaccharide derived from chitin biomass, such as N-acetylglucosamine (NAG), to N-acylethanolamine “over cost-effective Ni/CeO2-based materials”, see Abstract; Fig. 1; Pgs. 7-10, 2.2. Catalysis: Chitin Valorization – 2.3. Catalysis: Reaction Mechanism; Fig. 6; Pg. 9, Scheme 1, meeting the biomass amino saccharide in instant application claim 22.
Zheng does not teach the instant application claim 22 saccharide to the composite catalyst ratio.
Regarding the limitations of instant application claim 22, Beckham teaches the compound derived from biomass, such as 2-phenoxy-1-phenethanol (PE), “to catalyst loading of 1:2” or “2:1 catalyst loading” of “5 wt % Ni/HTC”, see Paras. [0017];[0033]-[0044];[0056];[0071], meeting within the ratio of biomass material and the composite catalyst in instant application claim 22.
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 nickel oxide catalyst of Zheng to use the nickel oxide LDH catalyst and the catalyst to biomass concentrations as taught by Beckham with a reasonable predictability of success for the purpose of efficiently producing renewable resources by “biomass conversion technologies” using solid “layered double hydroxides (LDHs) as recyclable, heterogeneous catalysts for” “base-catalyzed depolymerization (BCD) of” biomass to compounds, such as alcohols, “hydrocarbons, or other advanced fuels” without the addition of added base, such as NaOH, thus avoiding “the cost of liquid-phase, non-recyclable base, and downstream processing steps such as neutralization”, see Beckham, Paras. [0003]-[0004];[0025];[0039]-[0042]; Fig. 2.
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 substituting the biomass degradation nickel oxide catalyst of Zheng by applying the known biomass degradation nickel-LDH catalyst as taught by Beckham with a reasonable predictability of success for the purpose of efficiently producing renewable resources by “biomass conversion technologies” using solid “layered double hydroxides (LDHs) as recyclable, heterogeneous catalysts for” “base-catalyzed depolymerization (BCD) of” biomass to compounds, such as alcohols, “hydrocarbons, or other advanced fuels” without the addition of added base, such as NaOH, thus avoiding “the cost of liquid-phase, non-recyclable base, and downstream processing steps such as neutralization”, see Beckham, Paras. [0003]-[0004];[0025];[0039]-[0042]; Fig. 2; 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 Zheng and Beckham both teach cost effective biomass degradation nickel oxide catalysts, a person of ordinary skill in the art has good reason to modify Zheng by relying upon Beckham before the effective filing date of the claimed invention for knowledge generally available within the cost effective biomass degradation nickel oxide catalyst art regarding the selection of the specific oxide catalyst, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing renewable resources by “biomass conversion technologies” using solid “layered double hydroxides (LDHs) as recyclable, heterogeneous catalysts for” “base-catalyzed depolymerization (BCD) of” biomass to compounds, such as alcohols, “hydrocarbons, or other advanced fuels” without the addition of added base, such as NaOH, thus avoiding “the cost of liquid-phase, non-recyclable base, and downstream processing steps such as neutralization”, see Beckham, Paras. [0003]-[0004];[0025];[0039]-[0042]; Fig. 2; 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, “[t]he normal desire of scientists or artisans to improve upon what is
already generally known provides the motivation to determine where in a disclosed set
of percentage ranges”, such as the concentration of the biomass and the catalyst, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), see MPEP 2144.05.
Selection of a known material, such as biomass degradation nickel impregnated/supported metal oxide catalysts, 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 reactant concentrations and reaction temperatures, “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.
Conclusion
No claims are allowed.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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