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 .
DETAILED ACTION
Claim Status
Claims 1-37 are pending. Claims 1-17 and 21-31 are under examination in their entirety. Claims 1-17 and 21-31 are rejected. No claims allowed.
Election/Restrictions
Claims 18-20 and 32-37 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 01/06/2026.
Specie Election
Upon further consideration the specie election in the restriction requirement mailed 06/30/2025 has been withdrawn. Claims 1-17 and 21-31 are under examination in their entirety.
Filing Receipt
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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.
Claim(s) 1, 13-17 and 21, 23-24, and 27-31 is/are rejected under 35 U.S.C. 103 as being unpatentable over Delcroix et al. (FR3028854, Published 05-2016. Machine translation attached).
Scope of the Prior Art
Delcroix et al. teach “The bioethanol is oxidized to bioacetaldehyde which can be dimerized to biocrotonaldehyde. The bioacetic acid can be pyrolyzed to produce bio- ketene. The reaction of bio-ketene with bio-crotonaldehyde forms a polyester which is degraded by acid hydrolysis or pyrolysis to form sorbic acid. The production of biobased sorbic acid according to this route is advantageously carried out in a manner known to those skilled in the art” (page 2 of 7, past middle of page).
The above reads on the conversion of acetic acid to ketene, reacting ketene with crotonaldehyde to produce a polyester and converting the polyester to sorbic acid made from renewable materials.
Concerning a)-e), the above passage of Delcroix et al. teach bioacetic acid can be pyrolyzed and bioacetaldehyde can be dimerized to biocrotonaldehyde. This is currently claimed b), c), and d).
Ascertain the Differences
The teachings of Delcroix et al. are centralized in one location of the reference.
However, the teachings do allow for choice. For example, “The bioacetic acid can be
pyrolyzed to produce bio- ketene”. Thus, a 103 obvious rejection is warranted.
Obviousness
From the limited options available it would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have prepared sorbic acid from renewable materials via, converting acetic acid to ketene; reacting the ketene with crotonaldehyde to produce a polyester; and converting the polyester to sorbic acid. Wherein the acetic acid is a bio-based acetic acid, the crotonaldehyde is a bio-based crotonaldehyde and the crotonaldehyde is produced by converting a bio-based acetaldehyde to crotonaldehyde. The ordinary artisan would have done so with a reasonable expectation of success due to the teachings of Delcroix et al (page 2 of 7, past middle of page).
The ordinary artisan would have also executed the above argued processes to ensure that the sorbic acid taught by Delcroix et al. was in fact biobased and made from renewable materials. Due to Delcroix et al. teaching biobased sorbic acid (page 2 of 7, past middle of page).
The ordinary artisan would have had motivation to perform the above argued known process steps to prepare biobased sorbic acid from renewable materials because Delcroix et al. teach “The production of biobased sorbic acid according to this route is advantageously carried out in a manner known to those skilled in the art” (page 2 of 7, past middle of page).
In general the ordinary artisan in need of biobased sorbic acid made from renewable materials would have sourced any and all reactants/reagents from biobased renewable material sources and reacted the reactants/reagents in a manner known to those skilled in the art with a reasonable expectation of success to ensure the sorbic
acid is biobased and made from renewable materials.
Concerning the determination of the about 15% or more of the carbon content in the sorbic acid, the current methods do not alter the product. Thus upon completing the processes to prepare the current product and thus obtaining the current product, the determination of the carbon content has been met. Moreover, ASTM D6866-21 is expected to change over time. Thus methods used currently may be altered.
Additionally, upon using known sources of reactants, the amount of biobased carbon utilized to prepare sorbic acid is known and counted. Concerning the percent carbon content, if only biobased reactants/renewable materials in the form of waste, organic and/or nonwaste materials are utilized, the carbon content from biobased sources would necessarily be 100%. Additionally, the biobased carbon would have been necessarily counted due to the knowledge of the biobased reactants/renewable materials utilized in preparing the claimed sorbic acid.
Claim(s) 2 is/are rejected under 35 U.S.C. 103 as being unpatentable over Delcroix et al. (FR3028854, Published 05-2016. Machine translation attached) as applied to claims 1, 13-17 and 21, 23-24, and 27-31 in the above rejection and in further view of Luke et al. (US Patent 2,820,058, Patent date 01-1958).
Scope of the Prior Art
The combined teachings of Delcroix et al. are in the above 103 rejection and are incorporated by reference.
Ascertain the Differences
Delcroix et al. does not teach the use of a phosphate catalyst when preparing
ketene from the acetic acid.
Secondary References
Luke et al. teach the triethyl phosphate catalyzed vapor phase conversion of acetic acid to ketene (Example 1).
Luke et al. teach “ketene may be obtained in high yields” (column 1, lines 45-55).
The above teachings of the secondary reference overlap with the teachings of the primary reference and render the secondary reference analogous art to the invention.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have utilized the methods taught by Luke et al. to prepare the bio-ketene taught by Delcroix et al. and arrive at the current invention with a reasonable expectation of success. The ordinary artisan would have done so to satisfy a need for a method and because of the high yields.
The ordinary artisan would have looked to Luke et al. and would have combined the teachings therein with Delcroix et al. due to the overlapping subject matter and because Luke et al. being analogous art the invention.
Claim(s) 3 is/are rejected under 35 U.S.C. 103 as being unpatentable over
Delcroix et al. (FR3028854, Published 05-2016. Machine translation attached) as applied to claims 1, 13-17 and 21, 23-24, and 27-31 in the above rejection and in further view of Weil et al. (JP44 14328, Published 06-1969. Translation attached).
Scope of the Prior Art
The combined teachings of Delcroix et al. are in the above 103 rejection and are incorporated by reference.
Ascertain the Differences
Delcroix et al. does not teach the use of a basic catalyst when preparing crotonaldehyde from the biobased acetaldehyde.
Secondary References
Weil et al. teach the production of crotonaldehyde via the aldol condensation (aldolization) of acetaldehyde and dehydration to produce the unsaturated aldehyde (page 1, 1st column). Weil et al. goes on to teach the aldol condensation is performed with an alkaline catalyst (column 2, bridging columns 8-9).
The above teachings of the secondary reference overlap with the teachings of the primary reference and render the secondary reference analogous art to the invention.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the
effective filing date of the claimed invention to have utilized the base catalyzed methods taught by Weil et al. to prepare the bio-crotonaldehyde taught by Delcroix et al. and arrive at the current invention with a reasonable expectation of success. The ordinary artisan would have done so to satisfy a need for a method of aldol condensation.
The ordinary artisan would have looked to Weil et al. and would have combined the teachings therein with Delcroix et al. due to the overlapping subject matter and because Weil et al. being analogous art the invention.
Claim(s) 4 is/are rejected under 35 U.S.C. 103 as being unpatentable over Delcroix et al. (FR3028854, Published 05-2016. Machine translation attached) as applied to claims 1, 13-17 and 21, 23-24, and 27-31 in the above rejection and in further view of Fernholz et al. (US 3,021,365, Published 02-1962).
Scope of the Prior Art
The combined teachings of Delcroix et al. are in the above 103 rejection and are incorporated by reference.
Ascertain the Differences
Delcroix et al. does not teach the use of a fatty acid salt of a divalent and/or
trivalent metal of subgroup II to VIII of the Periodic Table in the presence of an inert
solvent.
Secondary References
Fernholz et al. teach the production of the polyester via the reaction of ketene
with crotonaldehyde as follows (column 1). The below iron is a group VIII metal.
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Fernholz et al. teach sorbic acid to be obtained in a better yield as compared with the known process (column 1, lines 25-30).
The above teachings of the secondary reference overlap with the teachings of the primary reference and render the secondary reference analogous art to the invention.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have utilized the methods to prepare sorbic acid taught by Fernholz et al. to prepare the sorbic acid from reacting the ketene with crotonaldehyde to produce a polyester; and converting the polyester to sorbic acid as taught by Delcroix et al. to arrive at the current invention. The ordinary artisan would have done so with a reasonable expectation of success to satisfy a method for reacting the ketene with crotonaldehyde to produce a polyester; and converting the polyester to sorbic acid as taught by Delcroix et al. The ordinary artisan would have utilized the
methods of Fernholz et al. due to the teaching of better yields.
The ordinary artisan would have looked to Fernholz et al. and would have
combined the teachings therein with Delcroix et al. due to the overlapping subject matter and because Fernholz et al. being analogous art the invention.
Claim(s) 5 is/are rejected under 35 U.S.C. 103 as being unpatentable over
Delcroix et al. (FR3028854, Published 05-2016. Machine translation attached) as applied to claims 1, 13-17 and 21, 23-24, and 27-31 in the above rejection and in further view of Mollenkopf et al. (USPGPub 2003/0065218, Published 04-2003).
Scope of the Prior Art
The combined teachings of Delcroix et al. are in the above 103 rejection and are incorporated by reference.
Ascertain the Differences
Delcroix et al. does not teach the use of an inert solvent and an amine catalyst when preparing sorbic acid from the polyester.
Secondary References
Mollenkopf et al. teach the production of sorbic acid from a polyester as follows.
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The above teachings of the secondary reference overlap with the teachings of the primary reference and render the secondary reference analogous art to the invention.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have utilized the methods to thermally cleave the polyester taught by Mollenkopf et al. to prepare the sorbic acid taught by Delcroix et al. to arrive at the current invention. The ordinary artisan would have done so with a reasonable expectation of success to satisfy a method for cleaving the polyester to sorbic acid as taught by Delcroix et al. The ordinary artisan would have utilized the methods of Mollenkopf et al. to be able to reuse the amine catalyst.
The ordinary artisan would have looked to Mollenkopf et al. and would have combined the teachings therein with Delcroix et al. due to the overlapping subject matter and because Mollenkopf et al. being analogous art the invention.
Claim(s) 6 is/are rejected under 35 U.S.C. 103 as being unpatentable over Delcroix et al. (FR3028854, Published 05-2016. Machine translation attached) as applied to claims 1, 13-17 and 21, 23-24, and 27-31 in the above rejection and in further view of Kouno et al. (US Patent 6,512,142, Patented 01-2003).
Scope of the Prior Art
The combined teachings of Delcroix et al. are in the above 103 rejection and are incorporated by reference.
Ascertain the Differences
Delcroix et al. does not teach the use of potassium hydroxide when preparing
potassium sorbate from the polyester.
Secondary References
Kouno et al. teach the following (column 2, lines 25-40).
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Kouno et al. teach the following (column 1, lines 10-20).
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Kouno et al. teach the overall process to prepare sorbic acid from a polyester prepared from a reaction of ketene and crotonaldehyde as follows (column 1, line 10-30).
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The above teachings of the secondary reference overlap with the teachings of the primary reference and render the secondary reference analogous art to the invention.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the
effective filing date of the claimed invention to have utilized the sorbic acid taught by Delcroix et al. in the methods to prepare potassium sorbate taught by Kouno et al. to prepare potassium sorbate and arrive at the current invention with a reasonable expectation of success. The ordinary artisan would have done so to obtain potassium sorbate which is a food additive and has antiseptic and antimicrobial properties.
The ordinary artisan would have looked to Kouno et al. because of the overlapping synthesis of sorbic acid from ketene/crotonaldehyde with polyester decomposition and because Kouno et al. being analogous art the invention.
Claim(s) 7, 22 and 26 is/are rejected under 35 U.S.C. 103 as being unpatentable over Delcroix et al. (FR3028854, Published 05-2016. Machine translation attached) as applied to claims 1, 13-17 and 21, 23-24, and 27-31 in the above rejection and in further view of Dimian et al. (Novel energy efficient process for acetic acid production by methanol carbonylation, Chemical Engineering Research and Design, 159, pp. 1-12, Published 04-2020).
Scope of the Prior Art
The combined teachings of Delcroix et al. are in the above 103 rejection and are incorporated by reference.
Ascertain the Differences
Delcroix et al. does not teach the production of biobased acetic acid by reacting methanol derived from organic waste with carbon monoxide.
Secondary References
Dimian et al. teach the following (page 1 right column).
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Dimian et al. teach the following (page 2 left column).
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Dimian et al. teach biomass waste (page 2 left column).
The above teachings of the secondary reference overlap with the teachings of the primary reference and render the secondary reference analogous art to the invention.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have obtained 100% green acetic acid via methanol and carbon monoxide (CO) obtained from the biomass taught by Dimian et al. in the process to prepare bio-ketene taught by Delcroix et al. with a reasonable expectation of success. The ordinary artisan would have done so to satisfy a source of biobased acetic acid. As for the claimed organic waste and renewable organic material, Dimian et al. teach the raw materials (methanol, CO) can be obtained from any feedstock that include biogas and biomass.
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have utilized the biomass waste as a feedstock for the generation of the raw materials for green/biobased acetic acid. The ordinary artisan would have done so with a reasonable expectation of success because Dimian et al. teach “the trend of using methanol carbonylation is favorable from a sustainability viewpoint, as both raw materials can be obtained from any feedstock leading to syngas, such as biogas and biomass”.
The biomass waste taught by Dimian et al. is the claimed organic waste of current claim 7, renewable organic material of current claims 22 and 26.
The ordinary artisan would have looked to Dimian et al. and would have combined the teachings therein with Delcroix et al. due to the overlapping subject matter and because Dimian et al. being analogous art the invention.
Claim(s) 8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Delcroix et al. (FR3028854, Published 05-2016. Machine translation attached) as applied to claims 1, 13-17 and 21, 23-24, and 27-31 in the above rejection and in further view of Rana et al. (Chapter 3, Catalytic Transformation of Ethanol to Industrially Relevant Fine Chemicals, Biorefinery of Alternative Resources: Targeting Green Fuels and Platform Chemicals, Spronger, pp. 50-74, Published 2020).
Scope of the Prior Art
The combined teachings of Delcroix et al. are in the above 103 rejection and are
incorporated by reference.
Ascertain the Differences
Delcroix et al. does not teach the production of biobased acetic acid via the oxidation of biobased ethanol.
Secondary References
Rana et al. teach the following (page 51 top half of page).
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Rana et al. teach the following (page 50 second full paragraph).
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Rana et al. teach the oxidation of ethanol to produce acetic acid (page 52, Fig. 3.2, and page 58).
The above teachings of the secondary reference overlap with the teachings of the primary reference and render the secondary reference analogous art to the invention.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have obtained acetic acid via the oxidation of ethanol. The ordinary artisan would have done so with an expectation of
success because of the teachings of Rana et al. (page 52, Fig. 3.2, and page 58).
The ordinary artisan would have then used bioethanol to prepare the biobased acetic acid with a reasonable expectation of success because Rana et al. teach it is expected that ethanol will be used for the synthesis of industrially important chemicals such as acetaldehyde, acetic acid, ethylene…. In doing so the ordinary artisan would have arrived at the invention.
The ordinary artisan would have looked to Rana et al. and would have combined the teachings therein with Delcroix et al. due to the overlapping subject matter and because Rana et al. being analogous art the invention.
Claim(s) 9 is/are rejected under 35 U.S.C. 103 as being unpatentable over Delcroix et al. (FR3028854, Published 05-2016. Machine translation attached) as applied to claims 1, 13-17 and 21, 23-24, and 27-31 in the above rejection and in further view of Van Heiningen et al. (WO2009/059228, Published 05-2009).
Scope of the Prior Art
The combined teachings of Delcroix et al. are in the above 103 rejection and are incorporated by reference.
Ascertain the Differences
Delcroix et al. does not teach the production of biobased acetic acid recovered from wood extract.
Secondary References
Van Heiningen et al. teach the following.
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Van Heiningen et al. teach the following.
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The above teachings of the secondary reference overlap with the teachings of the primary reference and render the secondary reference analogous art to the invention.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have utilized the recovered acetic acid from wood extracts as taught by Van Heiningen et al. in the process to prepare the biobased sorbic acid taught by Delcroix et al. with a reasonable expectation of success. In doing so the ordinary artisan would have arrived at the current invention.
The ordinary artisan would have looked to Van Heiningen et al. and utilized the
acetic acid due to the high quantities, economic value and a biobased source of acetic
acid.
The ordinary artisan would have looked to Van Heiningen et al. and would have combined the teachings therein with Delcroix et al. due to the overlapping subject matter and because Van Heiningen et al. being analogous art the invention.
Claim(s) 10 and 25 is/are rejected under 35 U.S.C. 103 as being unpatentable over Delcroix et al. (FR3028854, Published 05-2016. Machine translation attached) as applied to claims 1, 13-17 and 21, 23-24, and 27-31 in the above rejection and in further view of Rana et al. (Chapter 3, Catalytic Transformation of Ethanol to Industrially Relevant Fine Chemicals, Biorefinery of Alternative Resources: Targeting Green Fuels and Platform Chemicals, Spronger, pp. 50-74, Published 2020).
Scope of the Prior Art
The combined teachings of Delcroix et al. are in the above 103 rejection and are incorporated by reference. The teachings of Rana et al. in the above 103 rejection are incorporated by reference.
Ascertain the Differences
Delcroix et al. does not teach the production of acetaldehyde from bioethylene and the catalytic dehydration of bioethanol.
Secondary References
Rana et al. teach the following (page 51 top half of page).
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Rana et al. teach the following (page 51 top half of page).
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Rana et al. teach the following (page 50 second full paragraph).
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The above teachings of the secondary reference overlap with the teachings of the primary reference and render the secondary reference analogous art to the invention.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have obtained acetaldehyde via the catalytic oxidation of ethylene, wherein the ethylene being obtained via the dehydration of ethanol. The ordinary artisan would have done so with an expectation of success because of the teachings of Rana et al. (page 51 top half of page).
The ordinary artisan would have then used bioethanol to prepare the acetaldehyde with a reasonable expectation of success because Rana et al. teach it is expected that ethanol will be used for the synthesis of industrially important chemicals
such as acetaldehyde, acetic acid, ethylene…. In doing so the ordinary artisan would
have arrived at the invention.
The ordinary artisan would have looked to Rana et al. and would have combined
the teachings therein with Delcroix et al. due to the overlapping subject matter and
because Rana et al. being analogous art the invention.
Claim(s) 11 and 12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Delcroix et al. (FR3028854, Published 05-2016. Machine translation attached) as applied to claims 1, 13-17 and 21, 23-24, and 27-31 in the above rejection and in further view of Dimian et al. (Novel energy efficient process for acetic acid production by methanol carbonylation, Chemical Engineering Research and Design, 159, pp. 1-12, Published 04-2020) and Rana et al. (Chapter 3, Catalytic Transformation of Ethanol to Industrially Relevant Fine Chemicals, Biorefinery of Alternative Resources: Targeting Green Fuels and Platform Chemicals, Spronger, pp. 50-74, Published 2020).
Scope of the Prior Art
The combined teachings of Delcroix et al. are in the above 103 rejection and are incorporated by reference. The teachings of Rana et al. and Dimian et al. are in the above 103 rejections are incorporated by reference.
Ascertain the Differences
Delcroix et al. does not teach the production of acetaldehyde from bioethylene
and the catalytic dehydration of bioethanol. Delcroix et al. does not teach the production of biobased acetic acid by reacting methanol derived from organic waste with carbon monoxide.
Secondary References
Rana et al. teach the following (page 51 top half of page).
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Rana et al. teach the following (page 51 top half of page).
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Rana et al. teach the following (page 50 second full paragraph).
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Dimian et al. teach the following (page 1 right column).
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Dimian et al. teach the following (page 2 left column).
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Dimian et al. teach biomass waste (page 2 left column).
The above teachings of the secondary references overlap with the teachings of the primary reference and render the secondary references analogous art to the invention.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have obtained acetaldehyde via the catalytic oxidation of ethylene, wherein the ethylene being obtained via the dehydration if ethanol. The ordinary artisan would have done so with an expectation of success because of the teachings of Rana et al. (page 51 top half of page).
The ordinary artisan would have then used bioethanol to prepare the acetaldehyde with a reasonable expectation of success because Rana et al. teach it is expected that ethanol will be used for the synthesis of industrially important chemicals such as acetaldehyde, acetic acid, ethylene…. In doing so the ordinary artisan would
have arrived at the invention.
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have obtained 100% green acetic acid via methanol and carbon monoxide (CO) obtained from the biomass taught by Dimian et al. in the process to prepare bio-ketene taught by Delcroix et al. with a reasonable expectation of success. The ordinary artisan would have done so to satisfy a source of biobased acetic acid. As for the claimed organic waste, Dimian et al. teach the raw materials (methanol, CO) can be obtained from any feedstock that include biogas and
biomass.
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have utilized the biomass waste as a feedstock for the generation of the raw materials for green acetic acid. The ordinary artisan would have done so with a reasonable expectation of success because Dimian et al. teach “the trend of using methanol carbonylation is favorable from a sustainability viewpoint, as both raw materials can be obtained from any feedstock leading to syngas, such as biogas and biomass”.
The ordinary artisan would have looked to Rana et al. and Dimian et al. and would have combined the teachings therein with Delcroix et al. due to the overlapping subject matter and because Rana et al. and Dimian et al. being analogous art the invention.
Conclusion
Any inquiry concerning this communication or earlier communications from the
examiner should be directed to BLAINE G DOLETSKI whose telephone number is (571)272-2766. The examiner can normally be reached M-F 7-4 EST.
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/B.G.D/
Examiner, Art Unit 1692 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625