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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination (RCE) under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 12 December 2025 has been entered.
Status of the Claims
Claims 1-16 are pending.
Claim 16 is amended.
Response to Amendments
Applicant’s amendments filed 12 December 2025 are acknowledged.
Response to Arguments
Applicant’s arguments filed 12 December 2025 have been fully considered and are not persuasive or moot. Due to the RCE filed on 12 December 2025, the 35 USC 103 rejections in the previous office action dated 12 August 2025 (hereinafter POA) have been withdrawn, and the 35 USC 102 rejection in the POA is maintained. Due to the RCE filed on 12 December 2025, upon further consideration, a new ground(s) of 35 USC 102 and 35 USC 103 rejections are provided below.
Applicant argues that Tustin, Horton, Kubic, Jr., Mostrou-Moser and/or Bonnet do not disclose the limitations as recited in previously presented claim 1 and in amended claim 16. These arguments have been considered but are not persuasive or moot for the reasons set forth in the reply to arguments below and in the new grounds of rejection below.
In response to applicant’s arguments on pages 6-7 of the remarks filed on 12 December 2025, that Horton does not disclose claim 16 under 102(a)(1) by referring to Table 3 of Horton and Horton does not teach the low impurity levels of formaldehyde and formic acid. The rejection is based on the crude product Table 1 of Horton not after the first distillation column Table 3 of Horton. Patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123.
As stated on pages 8-9 of the previous office action dated 12 August 2025 (hereinafter POA), Horton Table 1 teaches “non detectable levels of formaldehyde and formic acid before any further purification, i.e., the line 112 crude product mixture was removed, collected, and tested in order to identify the component wt.% concentrations in Table 1, see Paras. [0048];[0051], Table 1 below, and Fig. 1”
PNG
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165
312
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Greyscale
. To clarify, Horton teaches the 100% crude product composition of column 1 in Table 1 containing 89.9 to 90 wt% acetic acid, 5 wt% ethanol, and 5 wt% water, and levels of detection of other components such as formaldehyde and formic acid, and acetaldehyde of 0 to 0.1 wt% aka 0 to 1000 ppm, which is within the range of impurities in claim 16, and the 100% crude product composition of column 3 in Table 1 containing 25 wt% ethanol, 61.8 wt% acetic acid, 10 wt% water, 3 wt% ethyl acetate, 0.2 wt. % acetaldehyde, and 0 to undetectable levels of other components such as formaldehyde and formic acid, which is within the range of impurities in claim 16, see Table 1; Para. [0048].
Horton Table 1 also teaches at least 5 wt.% water; however as detailed below in the new 35 USC 112(a) enablement rejection below, the specification is enabling for the claim 16 bio-acetic acid solution after synthesis before any purification indicated as stream 5 which includes water, see specification Fig. 1B and 3A; Pg. 9, Lns. 7-10; Pg. 10, Lns. 19-21; Pg. 14, Lns. 7-15; Pg. 17, Lns. 1-3, the specification does not reasonably provide enablement for the claim 16 anhydrous/glacial bio-acetic acid solution after synthesis before any purification. Therefore, claim 16 is herein interpreted to state, “with after synthesis levels in formaldehyde and formic acid below 10 ppm before any purification wherein said bio-acetic acid comprises 99.7 wt% bio-based carbon”.
For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant’s arguments of pages 7-9 and 12 of the remarks filed on 12 December 2025, restating the instant specification, restating the claims, that an anhydrous bio-acetic acid solution is obtained after the azeotropic distillation, “a fully bio-based anhydrous acetic acid solution with the claimed characteristics prior to any purification”, and prior art relies upon “conventional distillation to achieve glacial purity, and no evidence existed of any “as-synthesized” bio-acetic acid meeting specification without purification”. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims, see In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993) and MPEP 2111.01.
As detailed above and below in the new 35 USC 112(a) enablement rejection, the specification is enabling for the claim 16 bio-acetic acid solution after synthesis before any purification indicated as stream 5 which includes water, see specification Fig. 1B and 3A; Pg. 9, Lns. 7-10; Pg. 10, Lns. 19-21; Pg. 14, Lns. 7-15; Pg. 17, Lns. 1-3, the specification does not reasonably provide enablement for the claim 16 anhydrous/glacial bio-acetic acid solution after synthesis before any purification.
As indicated in the new 35 USC 112(b) rejection below, the instant specification and instant claims 1 and 5 teach contradictory paths to recovering the anhydrous/glacial acetic acid. For example, instant claim 1 states the step d) distillation is needed to recover the anhydrous acetic acid and instant claim 5 states about 99.8 and 99 % wt. anhydrous acetic acid is recovered after step c) before step d). It is unclear as to where the anhydrous acetic acid is obtained within the process, for example, step c) to 99 % wt., then step d) to greater than 99 % wt., is step d) optional, etc.
For the reasons indicated above and the new 35 USC 112(a) and 112(b) rejections below, applicant’s above arguments are not persuasive.
In response to applicant’s arguments on pages 9-10, 11-12, and 14 of the remarks filed on 12 December 2025, that Tustin “is not concerned with the preparation of highly pure bio-based acetic acid without the need of further purification”, “there was no solution available for high production scale of fully bio-based acetic acid at reasonable price (without the need of further purification steps)”, and “the unexpected result of obtaining fully bio-based glacial acetic acid directly from synthesis with minimal treatment after synthesis”. As stated above, the instant specification and claims require further purification steps to obtain “highly pure bio-based acetic acid” or anhydrous/glacial acetic acid. The test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art, see In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981) and MPEP 2145.
As stated on pages 10-11 of the POA, Tustin is in the known prior art field of the use of azeotropes to separate acetic acid from an aqueous mixture. Claim 1 is not drawn to the production of acetic acid or to a specific copper, iron, and/or nickel content, it is drawn to the separation and purification of “a feedstock aqueous solution of acetic acid”. Tustin also teaches the separation and purification of “a feedstock aqueous solution of acetic acid”.
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 Tustin teaches the azeotropic separation of acetic acid from an aqueous mixture, a person of ordinary skill in the art has good reason to rely upon Tustin before the effective filing date of the claimed invention for knowledge generally available within the organic acid azeotropic aqueous mixture separation art, see MPEP 2143 B & G and 2141, for the benefit of isolating a highly valuable chemical, see Tustin, Abstract; Col. 5, Ln. 57-Col. 7, Ln. 65.
For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant’s arguments on pages 10-11 of the remarks filed on 12 December 2025, that the selection of butyraldehyde from the list of azeotrope agents detailed by Tustin “does not constitute “a finite number of identified predictable solutions””, “runs against the guidance of the reference and standard industrial practice, where esters or ketones are favored for stability and separation behavior”, and there is not motivation to select butyraldehyde. Objective evidence “must be factually supported by an appropriate affidavit or declaration”, see MPEP 716.01(c)I. Patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123.
As stated on pages 6-7 of the POA, “Tustin teaches a variety of azeotrope agents, such as butyraldehyde, that are used instead of ethyl acetate. Tustin’s teaching of ethyl acetate as “preferred” does not lead a person of ordinary skill in the art to not choose a differing azeotrope, such as butyraldehyde, that forms a minimum-boiling azeotrope with water and predictably separates into water-rich and organic-rich liquid phases upon condensation, see Tustin, Col. 7, Lns. 1-22 and Claim 26, step (d). In addition, Tustin teaches the selection of the azeotrope is from “a finite number of identified predictable solutions”, see MPEP 2143 I.E.”
Tustin teaches the selection of ethyl acetate is preferred because ethyl acetate is already a component of or formed in the aqueous water mixture derived from synthesis gas including carbon monoxide which is used to produce acetic acid, see Col. 1, Ln. 11-Col. 2, Ln. 38; Col. 7, Lns. 1-65, where a second azeotropes having a boiling point lower than ethyl acetate is also applied, such as acetone, see Col. 5, Ln. 57-Col. 7, Ln. 65.
Steitz, Jr. et al. (“Products of Hydrogenation of Carbon Monoxide - Water-Soluble Oxygenated Compounds”, Published February 1953, Industrial and Engineering Chemistry, Vol. 45, No. 2, Pgs. 353-358, herein after Steitz) is in the known prior art field of fractional azeotropic separation of aqueous scrubber solutions obtained from the water stream produced by hydrogenation of carbon monoxide over an iron catalyst, see Abstract; Pgs. 353-356, Figs. 1-2; Tables I-IV. Steitz teaches the produced water stream comprises acetic acid and water along with the azeotropes acetone, ethyl acetate, and butyraldehyde, see Pgs. 354-356, Tables I-IV, where the stream is fractionated to separately produce a fraction containing the acetone, the ethyl acetate, and the butyraldehyde in combination, see Pg. 358, Fig. 4.
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 and published prior art are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and both Tustin and Steitz teach the azeotropic separation of acetic acid from an aqueous mixture, where the azeotrope may be a compound already present in the aqueous mixture, such as ethyl acetate and/or butyraldehyde, in the organic acid azeotropic aqueous mixture separation art, a person of ordinary skill in the art has good reason to modify Tustin by relying upon Steitz before the effective filing date of the claimed invention for knowledge generally available within the organic acid azeotropic aqueous mixture separation art regarding choosing an azeotrope that will fractionate at the same time as ethyl acetate, such as butyraldehyde, see MPEP 2143 B & G and 2141, for the benefit of efficiently recovering the desired organic acid from an aqueous mixture by azeotropic fractionation, see Steitz, Abstract: Pgs. 353-355, Fig. 1, Tables I-III, and MPEP 2141.
For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant’s argument on page 11 of the remarks filed on 12 December 2025, that Bonnet does not relate to the inventive process. “A reference is analogous art to the claimed invention if: (1) the reference is from the same field of endeavor as the claimed invention (even if it addresses a different problem); or (2) the reference is reasonably pertinent to the problem faced by the inventor (even if it is not in the same field of endeavor as the claimed invention).”, see MPEP 2141.01(a).
Tustin is in the known prior art field of catalytically producing hydrocarbons via an iron containing catalyst in the correct oxidation state and further separation of the produced aqueous stream by azeotropic distillation, see Abstract; Col. 8, Lns. 32-42.
Bonnet is in the known prior art field of “a process for producing carboxylic acids by oxidation of a hydrocarbon with oxygen or a gas containing oxygen”, see Abstract, where the oxidation is performed in the presence of an iron catalyst, see Para. [0041]; Claims 22 and 41, further separation of the produced aqueous stream by azeotropic distillation, see Paras. [0021]-[0022];[0087];[0089], and is applied in the POA to teach the known prior art for room/ambient temperature in Celsius, see Para. [0036].
Therefore, it would have been obvious for a person of ordinary skill in the art to modify Tustin by relying upon Bonnet before the effective filing date of the claimed invention for knowledge generally available within the art regarding room temperature in Celsius and the separation of carboxylic acids from a mixed products liquid stream, see MPEP 2143 B & G.
For the reasons indicated above, applicant’s above argument is not persuasive.
In response to applicant’s arguments on pages 11-12 of the remarks filed on 12 December 2025, that one of ordinary skill in the art would not combine the teachings of Horton and Tustin without undue burden. The test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art, see In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981) and MPEP 2145.
As stated above, instant claim 1 is not drawn to the production of acetic acid, it is drawn to the separation and purification of “a feedstock aqueous solution of acetic acid”. Tustin also teaches the separation and purification of “a feedstock aqueous solution of acetic acid”. As stated on pages 13-14 of the POA, Horton also teaches the separation and purification of “a feedstock aqueous solution of acetic acid”.
Therefore, it would have been obvious for a person of ordinary skill in the art to modify Tustin by relying upon Horton before the effective filing date of the claimed invention for knowledge generally available within the art regarding the separation of carboxylic acids from a mixed products liquid stream, see MPEP 2143 B & G.
For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant’s arguments on pages 12-14 of the remarks filed on 12 December 2025, that Kubic, Jr. is not drawn to the production of acetic acid and there is no teaching in Kubic, Jr. “that the use of butanal (butyraldehyde) could be extrapolated to be applicable to the extraction of acetic acid and that such a use would lead to the claimed advantages and allow the obtaining of a product of claim 16”. Patents and published prior art are part of the literature of the prior art relevant for all they contain, see MPEP 2123. “A reference is analogous art to the claimed invention if: (1) the reference is from the same field of endeavor as the claimed invention (even if it addresses a different problem); or (2) the reference is reasonably pertinent to the problem faced by the inventor (even if it is not in the same field of endeavor as the claimed invention).”, see MPEP 2141.01(a).
As stated above, instant claim 1 is not drawn to the production of acetic acid, it is drawn to the separation and purification of “a feedstock aqueous solution of acetic acid”. Tustin also teaches the separation and purification of “a feedstock aqueous solution of acetic acid”.
Kubic, Jr. is in the known prior art field of the separation of hydrocarbons, such as acetic acid, from a fermentation broth, see Abstract; Fig. 1. Kubic, Jr. does teach the azeotropic separation of acetic acid in a feed broth depicted in Fig. 1 containing acetic acid, ethanol, water, and other compounds, with kg/hour of butanal aka butyraldehyde as the azeotrope in the system, and with kg/hour feed broth, see Fig. 1; Pg. 5242, Table 1. Kubic, Jr. teaches butanal in an azeotropic separation of a solution starting with 0.89 wt% acetic acid and after azeotropic distillation with butanal the solution contains 0.96 wt% acetic acid. As a result, Kubic, Jr. teaches butanal in an azeotropic distillation separation of a solution containing acetic acid where a higher concentration of acetic acid is obtained after the butanal azeotropic distillation separation.
Therefore, it would have been obvious for a person of ordinary skill in the art to modify the azeotropic separation of Tustin by relying upon the azeotropic separation of Kubic, Jr. before the effective filing date of the claimed invention for knowledge generally available within the art regarding the azeotropic separation of carboxylic acids from a mixed products liquid stream, see MPEP 2143 B & G.
For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant’s argument on page 14 of the remarks filed on 12 December 2025, that Mostrou-Moser does not teach that butyraldehyde “could be used to the extraction of acetic acid”. The test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art, see In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981) and MPEP 2145.
In this case, Mostrou-Moser is not applied to teach the azeotropic extraction of acetic acid with butyraldehyde. As stated on pages 21-22 and 25 of the POA, Mostrou-Moser is applied to teach the aerobic oxidation synthesis of acetic acid from an ethanol/water solution.
Therefore, it would have been obvious for a person of ordinary skill in the art to modify Tustin to azeotropically separate the aerobic oxidation synthesized acetic acid solution of Mostrou-Moser before the effective filing date of the claimed invention, see MPEP 2143 B & G.
For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant’s arguments on page 14 of the remarks filed on 12 December 2025 regarding the use of an oxidation-derived feedstock already containing extremely low C1 impurities, it is noted that claim 16 is the only claim appearing to recite limitations relating to this argument, and the synergistic effects drawn from the combined teachings of Horton, Bonnet, Tustin, and Mostrou-Moser. Claim 16 is herein rejected under 35 USC 102(a)(1) applying the teachings of Horton alone and newly rejection applying the teachings of Gorbanev et al. (“Acetic Acid Formation by Selective Aerobic Oxidation of Aqueous Ethanol over Heterogeneous Ruthenium Catalysts”, published 28 February 2012, ACS Catalysis, Vol. 2, Pgs. 604-612, hereinafter Gorbanev) alone, see below. Therefore, applicant’s arguments regarding the synergistic effects drawn from the combined teachings of Horton, Bonnet, Tustin, and Mostrou-Moser are moot. For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicants arguments on page 15 of the remarks filed on 12 December 2025 “that the use of butaraldehyde also provides for improved purification of acetic acid (as compared to ethyl acetate) since the use of butaraldehyde avoids the extraction of transition metals, like copper, iron, and nickel (which not transferred to the extract stream (stream 12))” and such “a difference and improvement (avoiding extraction of transition metals) is not taught or suggested by the prior art”. It is noted that the avoidance of the extraction of transition metals, like copper, iron, and nickel is not instantly claimed. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims, see In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993) and MPEP 2111.01. For the reasons indicated above, applicant’s above arguments are not persuasive.
Maintained and New Rejections based on the RCE filed on
12 December 2025
For clarity between the maintained and new rejections, the specific maintained
35 USC 102 rejection is in italics.
Claim Objections
Claims 11, 13, and 15 are newly objected to because of the following informalities:
Claim 11, step iv) states “in presence” and “in ethanol”, which appear to include typographical mistakes. Claim 11 is interpreted to state “in the presence” and “in the ethanol”.
Claim 13, line 3 states “wt. %which”, which appears to include a typographical mistake. Claim 13 is interpreted as “ which”.
Claim 15 states “platin-based”, which appears to include a spelling mistake. Claim 15 is interpreted as “platinum-based”.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
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.
Claim 16 is newly rejected under 35 U.S.C. 112(a) as failing to comply with the enablement requirement. The claim contains subject matter which was not described in the specification in such a way as to enable one skilled in the art to which it pertains, or with which it is most nearly connected, to make and/or use the invention.
Claim 16 is rejected under 35 U.S.C. 112(a) because the specification; while being enabling for the claim 16 bio-acetic acid solution after synthesis before any purification indicated as stream 5 which includes water, see specification Fig. 1B and 3A; Pg. 9, Lns. 7-10; Pg. 10, Lns. 19-21; Pg. 14, Lns. 7-15; Pg. 17, Lns. 1-3, the specification does not reasonably provide enablement for the claim 16 anhydrous bio-acetic acid solution after synthesis before any purification. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the invention commensurate in scope with the claim. This is a scope of enablement rejection.
To be enabling, the specification of the patent must teach those skilled in the art how to make and use the full scope of the claimed invention without undue experimentation. In re Wright, 999 F.2d 1557, 1561 (Fed. Cir. 1993). Explaining what is meant by “undue experimentation,” the Federal Circuit has stated:
The test is not merely quantitative, since a considerable amount of experimentation is permissible, if it is merely routine, or if the specification in question provides a reasonable amount of guidance with respect to the direction in which the experimentation should proceed to enable the determination of how to practice a desired embodiment of the claimed invention. PPG v. Guardian, 75 F.3d 1558, 1564 (Fed. Cir. 1996).
The factors that may be considered in determining whether a disclosure would require undue experimentation are set forth by In re Wands, 8 USPQ2d 1400 (CAFC 1988) at 1404 where the court set forth the eight factors to consider when assessing if a disclosure would have required undue experimentation. Citing Ex parte Formal, 230 USPQ 546 (BdApls 1986) at 547 the court recited eight factors:
1) the quantity of experimentation necessary,
2) the amount of direction or guidance provided,
3) the presence or absence of working examples,
4) the nature of the invention,
5) the state of the prior art,
6) the relative skill of those in the art,
7) the predictability of the art, and
8) the breadth of the claims.
These factors are always applied against the background understanding that scope of enablement varies inversely with the degree of unpredictability involved. In re Fisher, 57 CCPA 1099, 1108, 427 F.2d 833, 839, 166 USPQ 18, 24 (1970). Keeping that in mind, the Wands factors are relevant to the instant fact situation for the following reasons:
Factor 8, the Breadth of the Claims and Factor 4, the Nature of the Invention
Claim 16 recites an anhydrous bio-acetic acid solution after synthesis before any purification. The specification recites the after the reaction stream is stream 5 which contains water, see Fig. 1B and 3A; Pg. 9, Lns. 7-10; Pg. 10, Lns. 19-21; Pg. 14, Lns. 7-15, and glacial or anhydrous acetic acid is only produced after purification of stream 5 to stream 7, then to stream 10, then to stream 12, then to stream 14, see Figs. 1A-1B, 3A-3B; Pg. 9, Lns. 7-10; Pg. 10, Lns. 19-28; Pg. 12, Ln. 24-Pg. 13, Ln. 6; Pg. 14, Ln. 7-Pg. 15, Ln. 2; Pg. 17, Lns. 1-12 and 18-31.
Factor 6, the Relative Skill Level, Factor 5, the State of the Prior Art, and Factor 7, the Level of Predictability in the Art
The invention relates to a method for the preparation of bio-acetic acid and the product thereof. The relative skill of those in the art is high, that of an MD or PHD with experience in inorganic chemistry for the selection of the catalyst, organic chemistry for the selection of the reactants and azeotropes, industrial chemistry for the selection of the differing reactors, industrial processes for the selection of the sequence of differing purification reactors, and environmental industrial process chemistry for the selection of bio-based materials and environmentally friendly processing.
Catalytic synthesis of hydrocarbons is a highly technical experienced choice of the organic and inorganic constituents and the reactors employed throughout the process. The variety of choices amongst the organic and inorganic constituents and the reactors employed throughout the process enables vast opportunities for the synthesis of a variety of hydrocarbons, leading to materials with intrinsically variable properties, yield, and purity. Due to the almost unlimited choice between the organic and inorganic constituents and the reactors employed throughout the process, the state of the art leads to a vast amount of experimental techniques in order to synthesize an anhydrous hydrocarbon.
The instant specification provides no guidance as to the synthesis of an anhydrous bio-acetic acid solution after the reaction without any purification. On the contrary, the specification is drawn to an aqueous acetic acid solution after synthesis that undergoes multiple purification steps after synthesis in order to obtain glacial or anhydrous acetic acid. Without guidance from the specification, the variety of choices in synthesizing an anhydrous bio-acetic acid solution after the reaction without any purification leads to a lack of predictability in various outcomes. A highly skilled MD or PHD would need to perform a vast amount of experimentation in inorganic chemistry for the selection of the catalyst, in organic chemistry for the selection of the reactants and azeotropes, in industrial chemistry for the selection of the differing reactors, in industrial processes for the selection of the sequence of differing purification reactors, and in environmental industrial process chemistry for the selection of bio-based materials and environmentally friendly processing in order to synthesize an anhydrous bio-acetic acid solution after the reaction without any purification.
Factor 2, the Amount of Direction or Guidance Provided and Factor 3, the Presence or Absence of Working Examples
The specification provides no direction or guidance for the synthesize of an anhydrous bio-acetic acid solution after the reaction without any purification. No reasonably specific guidance is provided concerning the synthesis of an anhydrous bio-acetic acid solution after the reaction without any purification. The synthesis is not corroborated by any working example. On the contrary, the specification is drawn to an aqueous acetic acid solution after synthesis that undergoes multiple purification steps after synthesis in order to obtain glacial or anhydrous acetic acid.
Factor 1, the Quantity of Experimentation Necessary
Because of the known unpredictability of the art, and in the absence of experimental evidence, no person of skill in the art would accept the assertion that the instantly claimed synthesize of an anhydrous bio-acetic acid solution after the reaction without any purification could be predictably made or used without vase experimentation with no guidance from the specification. Accordingly, claim 16 does not comply with the enablement requirement of 35 U.S.C. 112(a), since to practice the invention claimed in the patent a person of ordinary skill in the art would have to engage in undue experimentation, with no assurance of success.
Claim 16 is herein interpreted to state, “Awith after synthesis levels in formaldehyde and formic acid below 10 ppm before any purification wherein said bio-acetic acid comprises 99.7 wt% bio-based carbon.
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 1-15 are newly 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.
Claim 1, step b) recites the limitation “the obtained mixture”. There is insufficient antecedent basis for this limitation in the claim. Claim 1, step b) is interpreted to state “an obtained mixture”.
Regarding claims 1 and 4, claim 1, step c) and claim 4 recite the limitations “acetic acid from butyraldehyde”. There is insufficient antecedent basis for these limitations in the claims. The claims are interpreted to state “the acetic acid from the butyraldehyde”.
Claim 1, steps b) and c) lack clarity. Step b) states “a water-poor phase rich in butyraldehyde” and step c) states “water-poor phase rich in butyraldehyde and acetic acid”. The claim lacks clarity as it does not establish whether there are differing separate water-poor phases, one containing acetic acid and one not containing acetic acid or just one water-poor phase containing butyraldehyde and acetic acid. For clarity, step b) is interpreted to state, “a water-poor phase rich in butyraldehyde and acetic acid”.
Claim 1, step d) lacks clarity. Step d) states “d) recovering anhydrous acetic acid by distillation of the water-poor phase rich in butyraldehyde”. The claim lacks clarity as it does not establish which water-poor phase from step b) or step c) is subjected to distillation in step d), and it does not establish which extracted phase the separated acetic acid or the separated butyraldehyde in step c) is or is not subjected to distillation in step d). For clarity, step d) is interpreted to state, “d) recovering anhydrous acetic acid by distillation of the step c) separated acetic acid
Claims 1 and 5 appear to teach contradictory paths to recovering the anhydrous/glacial acetic acid. For example, claim 1 states the step d) distillation is needed to recover the anhydrous acetic acid and claim 5 states about 99.8 and 99 % wt. anhydrous acetic acid is recovered after step c) before step d). It is unclear as to where the anhydrous acetic acid is obtained within the process, for example, step c) to 99 % wt., then step d) to greater than 99 % wt., is step d) optional, etc. Claims 1 and 5 lack clarity.
Claims 2-15 depend from base claim 1 and are included in this rejection as they
do not correct the informalities identified in base claim 1.
Claim 2 recites the limitations “the feedstock mass” and “butyraldehyde”. There is insufficient antecedent basis for these limitations in the claim.
Claim 3 recites the limitation “the extraction vessel”. There is insufficient antecedent basis for this limitation in the claim.
Claim 4 depends from claim 1. Claim 4 states “a water-poor phase rich in butyraldehyde”. Claim 1, step b) states “a water-poor phase rich in butyraldehyde” and step c) states “water-poor phase rich in butyraldehyde and acetic acid”. The claim lacks clarity as it does not establish whether there are differing separate water-poor phases, one containing acetic acid and one not containing acetic acid or just one water-poor phase containing butyraldehyde and acetic acid. For clarity, claim 4 is interpreted to state, “a water-poor phase rich in butyraldehyde and acetic acid”.
Claim 5 recites the limitation “the bottom liquid phase”. There is insufficient antecedent basis for this limitation in the claim.
Claim 6 recites the limitation “the distillate”. There is insufficient antecedent basis for this limitation in the claim.
Claim 8, line 7 recites the limitation “the reaction products”, line 9 recites “the volatiles” and “the remaining liquid phase”, line 11 recites “the aqueous solution”, and line 13 recites “the distillates”. There is insufficient antecedent basis for these limitations in the claim.
Claim 10, line 3 states “the molar content in ethanol”, which appears to lack antecedent basis and include a typographical mistake. Claim 10 is interpreted to state “a molar content in the ethanol”.
Claim 11 depends from claim 8. It is unclear as to whether claim 11 is drawn to differing ethanol/water mixtures, reaction vessels, heterogeneous catalysts, pressures, oxidations, reaction products, distillation step, evaporation step, etc. as claim 8 or whether most of the limitations in claim 11 lack antecedent basis because they are drawn to the same limitations as claim 8. It appears most of the limitations in claim 11 have insufficient antecedent basis.
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 § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim 16 stands rejected under 35 U.S.C. 102(a)(1) as being anticipated by Horton et al. (US20110190549, published 04 August 2011, hereinafter Horton).
Horton teaches the claim 16 limitations of an acetic acid synthesized from biomass, i.e., 100% bioderived or bio-based carbon content acetic acid, see Paras. [0039];[0041], is used in a hydrogenation process, see Para. [0045], which leads to a crude solution in line 112 containing unreacted synthesized biomass derived acetic acid at levels of up to 90 wt.% and non detectable levels of formaldehyde and formic acid before any further purification, i.e., the line 112 crude product mixture was removed, collected, and tested in order to identify the component wt.% concentrations in Table 1, see Paras. [0048];[0051], Table 1 below, and Fig. 1, meeting the limitations of instant claim 16.
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Claims 16 is newly rejected under 35 U.S.C. 102(a)(1) as being anticipated by Gorbanev et al. (“Acetic Acid Formation by Selective Aerobic Oxidation of Aqueous Ethanol over Heterogeneous Ruthenium Catalysts”, published 28 February 2012, ACS Catalysis, Vol. 2, Pgs. 604-612, hereinafter Gorbanev).
Regarding instant application claim 16, Gorbanev discloses a highly “selective and efficient aerobic oxidation of aqueous ethanol (2.5−50 wt %) to acetic acid with supported ruthenium hydroxide catalysts at elevated temperatures and oxygen pressures”, see Pg. 611, 4. Conclusions, where the ethanol is 100% bio-based ethanol from biomass, see Pg. 604, 1. Introduction, Scheme 1, and the product yield after the oxidation reaction of the 100% bio-based ethanol is greater than 99% bio-based acetic acid having 100% bio-based carbon content and less than 1% bio-based acetaldehyde, i.e., less than 1% to zero formic acid and formaldehyde, see Pg. 607, Table 3, Entry 2, Pg. 609, Table 4, Entry 4, Figs. 4-5, before any further purification, see Pg. 606, Col. 2, Last Para. – Pg. 607, Col. 1, Ln. 14; Pgs. 607-609, 3.4. Reference Experiments with Ru(OH)x/CeO2 - 3.5. Effect of the Ru(OH)x Loading on Supports, meeting the limitations of instant application claim 16.
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, 3-7, and 14 are newly rejected under 35 U.S.C. 103 as being unpatentable over Tustin et al. (US6121498, patented 19 September 2000, hereinafter Tustin), as evidenced by Bonnet et al. (US20060106251, published 18 May 2006, hereinafter Bonnet), in view of Steitz, Jr. et al. (“Products of Hydrogenation of Carbon Monoxide - Water-Soluble Oxygenated Compounds”, Published February 1953, Industrial and Engineering Chemistry, Vol. 45, No. 2, Pgs. 353-358 , herein after Steitz) in further view of Horton et al. (US20110190549, published 04 August 2011, hereinafter Horton).
Tustin is in the known prior art field of the use of azeotropes to separate acetic acid from an aqueous mixture, see Abstract, and catalytically producing hydrocarbons via an iron containing catalyst in the correct oxidation state and further separation of the produced aqueous stream by azeotropic distillation, see Abstract; Col. 8, Lns. 32-42.
Regarding instant application claims 1 and 3, Tustin teaches a method for the preparation/separation of acetic acid, see Col. 5, Ln. 57-Col. 6, Ln. 50, Figs. 1, and 2, comprising the steps of:
Providing a feedstock aqueous solution of acetic acid into an extraction vessel with an azeotrope, such as butyraldehyde instead of ethyl acetate, that forms a minimum-boiling azeotrope with water in order to separate the solution into water-rich and organic-rich butyraldehyde acetic acid liquid phases upon condensation, see Col. 5, Ln. 57-Col. 6, Ln. 50, Fig. 2, Col. 7, Lns. 1-22 and Claim 26, step (d), meeting step a) and step b) in instant claim 1, where the extraction is a liquid-liquid extraction carried out at room temperature, see Col. 5, Ln. 57-Col. 6, Ln. 50, Fig. 2, and Col. 7, Lns. 1-22, as evidenced by Bonnet, Para. [0036], room or “ambient temperature (10° C.-30° C.)”, meeting and within the range in instant application claim 3;
The extracted water-poor phase rich in azeotrope butyraldehyde and acetic acid is fed to an azeotropic distillation to separate acetic acid from butyraldehyde, see Col. 4, Lns. 53-61, Col. 5, Ln. 57-Col. 6, Ln. 50, Fig. 2; Col. 7, Lns. 1-22, meeting step c) in instant application claim 1; and,
Water is removed from the acetic acid and the acetic acid is recovered by distillation of the water-poor phase rich in azeotrope butyraldehyde, see Col. 5, Ln. 57-Col. 6, Ln. 50, Fig. 2, i.e., anhydrous acetic acid, meeting step d) in instant application claim 1.
Tustin does not teach:
The instant application claim 1 limitations of bio-based acetic acid comprising 99.7 wt% bio-based carbon content, a feedstock aqueous solution of acetic acid having an acetic acid concentration from about 1 to about 50 wt.%; b) specifically butyraldehyde as the azeotrope; and, e) recovering purified water by distillation of the water-rich phase; and,
The limitations of instant application claims 4-15.
Regarding the azeotrope agent, Tustin teaches in Col. 7, Lns. 1-22 “[m]ass-separating agents other than ethyl acetate are possible. Such agents may be selected from those organic compounds that from a minimum-boiling azeotrope with water and separate into water-rich and organic-rich liquid phases upon condensation. Those skilled in the art of separations may select such an alternate to ethyl acetate and modify the process depicted in FIG. 2 appropriately. … as ethyl acetate is a coproduct of the process its use as an azeotroping agent avoids introducing another compound to the process and as such is used in the preferred embodiment. In the preferred embodiment the azeotroping agent both forms a minimum boiling azeotrope with water and forms two liquid phases upon condensation. Potential azeotroping agents include, but are not limited to, … butyraldehyde”. Tustin teaches the selection of the azeotrope is from “a finite number of identified predictable solutions”, see MPEP 2143 I.E. Therefore, 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 Tustin to select butyraldehyde as the azeotrope for the liquid-liquid separation of acetic acid based on the ability of butyraldehyde to separate into water-rich and organic-rich liquid phases upon condensation, see Tustin, Col. 7, Lns. 1-22 and Claim 26, step (d).
Tustin teaches the selection of ethyl acetate is preferred because ethyl acetate is already a component of or formed in the aqueous water mixture derived from synthesis gas including carbon monoxide which is used to produce acetic acid, see Col. 1, Ln. 11-Col. 2, Ln. 38; Col. 7, Lns. 1-65, where a second azeotropes having a boiling point lower than ethyl acetate is also applied, such as acetone, see Col. 5, Ln. 57-Col. 7, Ln. 65.
Steitz is in the known prior art field of fractional azeotropic separation of aqueous scrubber solutions obtained from the water stream produced by hydrogenation of carbon monoxide over an iron catalyst, see Abstract; Pgs. 353-356, Figs. 1-2; Tables I-IV.
Regarding instant application claim 1, Steitz teaches the produced water stream comprises acetic acid and water along with the azeotropes acetone, ethyl acetate, and butyraldehyde, see Pgs. 354-356, Tables I-IV, where the stream is fractionated to separately produce a fraction containing the acetone, the ethyl acetate, and the butyraldehyde in combination, see Pg. 358, Fig. 4.
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 and published prior art are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and both Tustin and Steitz teach the azeotropic separation of acetic acid from an aqueous mixture, where the azeotrope may be a compound already present in the aqueous mixture, such as ethyl acetate and/or butyraldehyde, in the organic acid azeotropic aqueous mixture separation art, a person of ordinary skill in the art has good reason to modify Tustin by relying upon Steitz before the effective filing date of the claimed invention for knowledge generally available within the organic acid azeotropic aqueous mixture separation art regarding the choosing an azeotrope that will fractionate at the same time as ethyl acetate, such as butyraldehyde, see MPEP 2143 B & G and 2141, for the benefit of efficiently recovering the desired organic acid from an aqueous mixture by azeotropic fractionation, see Steitz, Abstract: Pgs. 353-355, Fig. 1, Tables I-III, and MPEP 2141, meeting butyraldehyde azeotrope in instant application claim 1.
Horton is in the known prior art field of continuous bio-based acetic acid and bio-based ethanol production, see Paras. [0039];[0041];[0051], Tables 1-5, and Figs. 1-2, and the separation of the produced azeotropic aqueous solutions, see Tables 1-5; Paras. [0069];[0074].
Regarding instant application claims 1 and 14, Horton teaches bio-based acetic acid continuously synthesized from biomass, i.e., 100% bioderived or bio-based carbon content acetic acid, see Paras. [0039];[0041];[0051], is used in a hydrogenation process, see Para. [0045], which leads to a crude solution in line 112 containing unreacted biomass derived acetic acid at levels of up to 90 wt.% and non detectable levels of formaldehyde and formic acid before any further purification, see Paras. [0048];[0051], Table 1 below, and Fig. 1, meeting:
Within the range of bio-based content in instant application claim 1;
The continuous flow in instant application claim 14;
A feedstock aqueous solution of acetic acid having up to 90 wt.% acetic acid, such as 25 wt.% ethanol, 10 wt.% water, 3 wt.% ethyl acetate, 0.2 wt.% acetaldehyde, 61.8 wt.% acetic acid, undetectable levels of others, such as aldehydes, see Para. [0048], and Table 1
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. The feed maybe subject to flash evaporation resulting in a feed with up to 90 wt.% acetic acid and 5 to 35 wt.% water , see Paras. [0051]-[0055], and Table 2
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, meeting and within the range of the feedstock solution in instant application claim 1;
Water is separated by distillation to form a water stream of 99 to 100 wt.% water that is essentially free of organic impurities, see Paras. [0008];[0014];[0078], and Table 5
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, meeting:
Step e) in instant application claim 1;
Regarding instant application claims 4 and 5, Horton teaches the extracted water-poor phase rich in azeotrope is subjected to an azeotropic distillation at a temperature from about 95° C. to 120° C. under atmospheric pressure to separate acetic acid from azeotrope, i.e., the azeotrope ethyl acetate is separated from the majority of acetic acid, where the residue contains 60 to 100 wt.% acetic acid, i.e., 100% includes 0% water, see Paras. [0008];[0063], and Table 3,
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, meeting:
Within the range in instant application claim 4; and,
Within the range in instant application claim 5.
Regarding instant application claim 6, Horton teaches the distillate containing azeotrope extracted from the azeotropic distillation contains from 10 to 90 wt.% ethyl acetate azeotrope and 1 to 25 wt.% water, see Paras. [0008];[0059];[0063], and Table 4
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, meeting and within the range in instant application claim 6.
Regarding instant application claim 7, Horton teaches water is separated by distillation to form a water stream of 99 to 100 wt.% water that is essentially free of organic impurities, see Paras. [0008];[0014];[0078], and Table 5
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, meeting the purification in instant application claim 7.
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 acetic acid feed solution and purification techniques of Tustin to use the bio-based crude acetic acid product mixture of Table 1, the bio-based acetic acid feed composition of Table 2, and/or the Table 3 distillation of bio-based acetic acid mixture and purification techniques of Horton and to further distill/purify/flash evaporate to recover and separate any additional products from the crude product mixture including purified water as taught by Horton with a reasonable predictability of success for the benefit of producing an environmentally friendly acetic acid with reduced production costs, see Horton, Paras. [0039];[0059];[0060].
In reference to the above claims, it would have also been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the ethyl acetate azeotrope of Tustin with the butyraldehyde azeotrope of Steitz with a reasonable predictability of success for the benefit of efficiently recovering the desired organic acid from an aqueous mixture by azeotropic fractionation, see Steitz, Abstract: Pgs. 353-355, Fig. 1, Tables I-III.
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 and prior art publications are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Tustin, Horton, and Steitz all teach the recovery and separation of acetic acid from a crude product mixture in the organic acid azeotropic aqueous mixture separation art, a person of ordinary skill in the art has good reason to modify Tustin by relying upon Horton and Steitz before the effective filing date of the claimed invention for knowledge generally available within the azeotropic aqueous mixture separation art, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing an environmentally friendly acetic acid with reduced production costs, see Horton, Paras. [0039];[0059];[0060], and separation efficiency, see Steitz, Abstract: Pgs. 353-355, Fig. 1, Tables I-III and MPEP 2141.
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.
Further, In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929) states “[i]t is
a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions”, see MPEP 2144.05 II.A.
Selection of a known material, such as bio-based acetic acid and/or a butyraldehyde azeotrope, 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, “[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 % compounds in the mixtures throughout the process, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), see MPEP 2144.05.
Claim 1-7 and 14 are newly rejected under 35 U.S.C. 103 as being unpatentable over Tustin et al. (US6121498, patented 19 September 2000, hereinafter Tustin), as evidenced by Bonnet et al. (US20060106251, published 18 May 2006, hereinafter Bonnet), in view of Steitz, Jr. et al. (“Products of Hydrogenation of Carbon Monoxide - Water-Soluble Oxygenated Compounds”, Published February 1953, Industrial and Engineering Chemistry, Vol. 45, No. 2, Pgs. 353-358 , herein after Steitz) in further view of Horton et al. (US20110190549, published 04 August 2011, hereinafter Horton), as applied to claims 1, 3-7, and 14 in the 35 USC 103 rejection above, in further view of Kubic, Jr. et al. (“Reactive Extraction Process for Separating 2,3-Butanediol from Fermentation Broth”, 16 March 2023, Industrial & Engineering Chemistry Research, Vol. 62, Pgs. 5241-5251, hereinafter Kubic).
Tustin does not teach the limitations of instant application claim 2.
Regarding instant application claim 2, Steitz teaches the produced water stream comprises acetic acid and water along with the azeotropes acetone, ethyl acetate, and butyraldehyde, see Pgs. 354-356, Tables I-IV, where the stream is fractionated to separately produce a fraction containing the acetone, the ethyl acetate, and the butyraldehyde in combination, see Pg. 358, Fig. 4.
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 and published prior art are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and both Tustin and Steitz teach the azeotropic separation of acetic acid from an aqueous mixture, where the azeotrope may be a compound already present in the aqueous mixture, such as ethyl acetate and/or butyraldehyde, in the organic acid azeotropic aqueous mixture separation art, a person of ordinary skill in the art has good reason to modify Tustin by relying upon Steitz before the effective filing date of the claimed invention for knowledge generally available within the organic acid azeotropic aqueous mixture separation art regarding the choosing an azeotrope that will fractionate at the same time as ethyl acetate, such as butyraldehyde, see MPEP 2143 B & G and 2141, for the benefit of efficiently recovering the desired organic acid from an aqueous mixture by azeotropic fractionation, see Steitz, Abstract: Pgs. 353-355, Fig. 1, Tables I-III, and MPEP 2141, meeting the butyraldehyde azeotrope in instant application claim 2.
Kubic relating to azeotropic separation applying butyraldehyde aka butanal as the azeotrope and water, see Abstract and Pg. 5241, Col. 1, teaches wherein butanal aka butyraldehyde is provided at 140% of the stoichiometric amount with equal flow to each stage of the reactive extraction with the feedstock broth mass, as calculated by the examiner a mass ratio of about 1.4, see Pg. 5242, Col. 2, 3.2.1. Reactive Extraction. -Pg. 5243, Col. 1, Ln. 5, and Fig. 1 depicts the feed broth contains acetic acid, ethanol, water, and other compounds, kg/hour of butanal in the system, and kg/hour feed broth, see Fig. 1, meeting and within the range in instant application claim 2.
Therefore, 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 butanal azeotropic distillation separation of Tustin with the butanal azeotropic distillation separation concentration as taught by Kubic with a reasonable predictability of success for the purpose of separating desired materials from a reaction broth with reduced production costs, see Kubic, Pg. 5242, Middle of Col. 2.
It would have also been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the ethyl acetate azeotrope of Tustin with the butyraldehyde azeotrope of Steitz with a reasonable predictability of success for the benefit of efficiently recovering the desired organic acid from an aqueous mixture by azeotropic fractionation, see Steitz, Abstract: Pgs. 353-355, Fig. 1, Tables I-III.
By applying “routine optimization” and “predictable results” to select the optimal azeotrope concentration, as taught by Kubic, one of ordinary skill in the art would have been motivated to make these modifications because Kubic provides a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to efficiently produce a separated composition, such as via azeotrope solvent extraction techniques, for the benefit of separating desired materials from a reaction broth with reduced production costs, see Kubic, Pg. 5242, Middle of Col. 2 and MPEP 2141.
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 and prior art publications are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Tustin, Steitz, and Kubic all teach the recovery and separation of acetic acid from a crude product mixture in the organic acid azeotropic aqueous mixture separation art, a person of ordinary skill in the art has good reason to modify Tustin by relying upon Steitz and Kubic before the effective filing date of the claimed invention for knowledge generally available within the azeotropic aqueous mixture separation art, see MPEP 2143 B & G and 2141, for the benefit of efficiently separating desired materials from a reaction broth with reduced production costs, see Kubic, Pg. 5242, Middle of Col. 2; see Steitz, Abstract: Pgs. 353-355, Fig. 1, Tables I-III and MPEP 2141.
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 % azeotrope agent, “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 a butyraldehyde azeotrope, 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.
Claims 1, 3-9, and 12-15 are newly rejected under 35 U.S.C. 103 as being unpatentable over Tustin et al. (US6121498, patented 19 September 2000, hereinafter Tustin), as evidenced by Bonnet et al. (US20060106251, published 18 May 2006, hereinafter Bonnet), in view of Steitz, Jr. et al. (“Products of Hydrogenation of Carbon Monoxide - Water-Soluble Oxygenated Compounds”, Published February 1953, Industrial and Engineering Chemistry, Vol. 45, No. 2, Pgs. 353-358 , herein after Steitz) in further view of Horton et al. (US20110190549, published 04 August 2011, hereinafter Horton), as applied to claims 1, 3-7, and 14 in the 35 USC 103 rejection above, in further view of Mostrou-Moser et al. (WO2021239641, 02 December 2021, hereinafter Mostrou-Moser).
Tustin does not teach the limitations of instant application claims 8, 9, 12, 13, and 15.
Regarding instant application claim 8, Horton teaches bio-based an acetic acid synthesized from biomass, i.e., 100% bioderived or bio-based carbon content acetic acid, see Paras. [0039];[0041], is used in a hydrogenation process, see Para. [0045], which leads to a crude solution in line 112 containing unreacted biomass derived acetic acid at levels of up to 90 wt.% and non detectable levels of formaldehyde and formic acid before any further purification, see Paras. [0048];[0051], Table 1 below, and Fig. 1, meeting and within the range of bio-based content in instant claim 8; where an ethanol and water mixture of 5 to 70 wt.% ethanol and 5 to 35 wt.% water is fed to a distillation vessel, see Paras. [0008];[0053]-[0055], Table 2, Figs. 1 and 2, meeting the feeding and within the range in instant application claim 8; reaction products containing acetic acid, water, unreacted ethanol, traces of acetaldehyde, unreacted oxygen, nitrogen and impurities are recovered, subjected to flash evaporation, and distilled, see Paras. [0044];[0048][0079], and Table 3
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, i.e., the reaction products are recovered in order for the wt.% to be measured and presented in the table. Table 3 shows the residue has acetic acid, zero acetaldehyde, and less than 1 wt.% ethanol and 60 to 100 wt.% acetic acid and less than 30% water, see Table 3. Additional flashers or distillation for evaporation of volatiles are used throughout the process, see Paras. [0060];[0062];[0065];[0079], meeting the recovering reaction products, volatile removal, distillation, and recovering of acetic acid aqueous solution within the range in instant application claim 8; and,
The distillates obtained from the distillation step are evaporated by evaporative distillation or a flasher to obtain water and ethanol, see Paras. [0008];[0060];[0062];[0065];[0072], and Table 4 above, meeting the subjecting evaporative step in instant application claim 8.
Regarding instant application claims 12 and 13, Horton teaches the feed between the reaction zone 101 and the distillation zone 102, including line 112 to 115, is stored at a temperature of about 21° C before being fed to further flashers and distillation, see Paras. [0060];[0065]-[0067], Tables 1-3, and Fig. 1. The evaporative distillation is performed at pressures from 10 KPa to 3000 KPa or 0.1 bar to 30 bar and temperatures of 95° C. to 120° C, see Paras. [0062]-[0063]. The flasher evaporation is performed at temperatures of from 50° C. to 500° C and pressures from 75 KPa to 1500 KPa 0.75 bar to 15 bar, see Para. [0051]. The distillation is performed to recover 20 to 75 wt.% ethanol and 30 to 70 wt.% water which is recycled back to the reaction vessel, see Paras. [0045];[0057];[0077], Fig. 2 recycle lines, and Table 4 below
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, meeting:
Within the ranges in instant application claim 12; and,
Within the ranges in instant application claim 13.
Tustin in view of Horton do not teach:
The claim 8 limitations of subjecting the ethanol/water mixture to aerobic oxidation under a temperature from about 160 to about 250°C at a pressure of 20-60 bar in presence of a heterogeneous catalyst; and,
The limitations of claims 9 and 15.
Mostrou-Moser is in the known prior art field of “preparing carboxylic acids by oxidizing primary alcohols in the liquid phase in the presence of ruthenium dioxide as a catalyst”, see Abstract.
Regarding instant application claims 8, 9, and 15, Mostrou-Moser teaches feeding an ethanol/water mixture containing from 0.5 to 95 vol.-% ethanol into a reaction vessel to perform an aerobic oxidation reaction in the presence of a ruthenium dioxide, RuO2, catalysts at a temperature of 75 to 250°C and at a pressure of 10 hPa to 10 MPa or 0.01 bar to 100 bar, see Pg. 4, Lns. 4-8, Pg. 5, Last Para., Pg. 6, Second Para.-Third Para., Pg. 8, Lns. 10-17, where the ethanol/water mixture is a bioethanol mixture obtainable by bioethanol production processes, see Pg. 1, Lns. 15-20 and Pg. 5, Sixth Para., meeting:
The subjecting step in instant application claim 8;
The bioethanol in instant application claim 9; and,
The catalysts in instant application claim 15.
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 acetic acid feed solution and purification techniques of Tustin to use the bio-based crude acetic acid product mixture of Table 1, the bio-based acetic acid feed composition of Table 2, and/or the Table 3 distillation of bio-based acetic acid mixture and purification techniques of Horton and the bio-based acetic acid oxidation production method of Mostrou-Moser, and to further distill/purify/flash evaporate to recover and separate any addition products from the crude product mixture including purified water as taught by Horton with a reasonable predictability of success for the purpose of producing an environmentally friendly acetic acid with reduced production costs, see Horton, Paras. [0039]; [0059];[0060] and Mostrou-Moser, Pg. 1, Lns. 15-20; Pg. 5, Sixth Para.
By applying “routine optimization” and “predictable results” to select the optimal acetic acid feedstock and purification techniques, as taught by Horton and Mostrou-Moser, one of ordinary skill in the art would have been motivated to make these modifications because Horton and Mostrou-Moser provide a finite number of identified, predictable solutions. A person of ordinary skill in the art has good reason to efficiently produce an acetic acid composition, such as via the use of bio-based materials and further purification techniques, for the benefit of producing an environmentally friendly acetic acid with reduced production, see Horton, Paras. [0039]; [0059];[0060] and Mostrou-Moser, Pg. 1, Lns. 15-20; Pg. 5, Sixth Para.
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 and published prior art are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Tustin, Horton, and Mostrou-Moser all teach the separation of acetic acid from an aqueous mixture in the organic acid aqueous mixture separation art, a person of ordinary skill in the art has good reason to modify Tustin by relying upon Horton and Mostrou-Moser before the effective filing date of the claimed invention for knowledge generally available within the organic acid aqueous mixture separation art, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing an environmentally friendly acetic acid with reduced production costs, see Horton, Paras. [0039]; [0059];[0060] and Mostrou-Moser, Pg. 1, Lns. 15-20; Pg. 5, Sixth Para. and MPEP 2141.
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 re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929) states “[i]t is
a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions”, see MPEP 2144.05 II.A.
Selection of a known material, such as bio-based acetic acid and/or a ruthenium oxidation 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, “[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 % compounds in the feed mixtures, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), see MPEP 2144.05.
Further, “[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 distillation pressures, temperatures, and reactant concentrations, “or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions.” In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929), see MPEP 2144.05.
Claims 1, 3-7, 10, 11, and 14 are newly rejected under 35 U.S.C. 103 as being unpatentable over Tustin et al. (US6121498, patented 19 September 2000, hereinafter Tustin), as evidenced by Bonnet et al. (US20060106251, published 18 May 2006, hereinafter Bonnet), in view of Steitz, Jr. et al. (“Products of Hydrogenation of Carbon Monoxide - Water-Soluble Oxygenated Compounds”, Published February 1953, Industrial and Engineering Chemistry, Vol. 45, No. 2, Pgs. 353-358 , herein after Steitz) in further view of Horton et al. (US20110190549, published 04 August 2011, hereinafter Horton), as applied to claims 1, 3-7, and 14 in the 35 USC 103 rejection above, in further view of Mostrou-Moser et al. (WO2021239641, 02 December 2021, hereinafter Mostrou-Moser) and Bonnet et al. (US20060106251, published 18 May 2006, hereinafter Bonnet).
Tustin does not teach the limitations of instant application claims 10 and 11.
Regarding instant application claim 10, Mostrou-Moser teaches the aerobic oxidation comprises supplying the reaction vessel with air flow with an amount of oxygen, such as dioxygen O2, in ethanol of the mixture at a pressure of 10 hPa to 10 MPa or 0.01 bar to 100 bar, see Pg. 6, Second Para.-Third Para., Pg. 10, meeting the oxygen and within the range of pressure in instant application claim 10.
Regarding instant application claim 11, Mostrou-Moser teaches said method comprising the following steps:
i) feeding an ethanol/water mixture containing from 0.5 to 95 vol.-% ethanol into a heating vessel, see Pg. 5, Last Para.; Pg. 10, Last Para., meeting and within the range of step i) in instant application claim 11;
ii) bringing the temperature of the ethanol/water mixture to a temperature from 75 to 250°C, see Pg. 5, Last Para.; Pg. 10; Fig. 1;Pg. 8, Lns. 10-17, meeting and within the range of step ii) in instant application claim 11;
A reaction vessel is used to perform an aerobic oxidation reaction in the presence of a ruthenium dioxide, RuO2, catalysts at a temperature of 75 to 250°C and at a pressure of 10 hPa to 10 MPa or 0.01 bar to 100 bar, see Pg. 4, Lns. 4-8, Pg. 5, Last Para., Pg. 6, Second Para.-Third Para., Pg. 8, Lns. 10-17, Pg. 10, meeting and within the range of step iii) in instant application claim 11 and meeting and within the range of most of step iv) in instant application claim 11.
Regarding instant application claim 11, Horton teaches v) recovering the reaction products containing acetic acid, water, unreacted ethanol, traces of acetaldehyde, unreacted oxygen, nitrogen and minor impurities, see Table 3,
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231
309
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; Paras. [0044];[0048];[0079], meeting step v) in instant application claim 11;
vi) removing the volatiles by evaporation, see Paras. [0062];[0079], i.e., impurities are removed via evaporative distillation, and transferring the remaining liquid phase containing acetic acid, water and unreacted ethanol to a distillation step for the removal of ethanol and traces of acetaldehyde, see Table 3 above, the residue has acetic acid, zero acetaldehyde, and less than 1 wt.% ethanol, meeting step vi) in instant application claim 11;
vii) recovering the aqueous solution from the distillation step, wherein the aqueous solution comprises acetic acid having at a concentration from 60 to 100 wt.% acetic acid and less than 30% water, see Para. [0008] and Table 3 above, meeting and within the range of step vi) in instant application claim 11; and
viii) subjecting the distillates obtained from the distillation step to an evaporation step to recover the unreacted ethanol in water, see Paras. [0008];[0062];[0072], and Table 4,
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314
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, i.e., evaporative distillation to obtain water and ethanol, meeting step viii) in instant application claim 11.
Tustin in view of Horton in further view of Mostrou-Moser do not teach the molar concentrations in instant application claims 10 and 11.
Bonnet is in the known prior art field of “a process for producing carboxylic acids by oxidation of a hydrocarbon with oxygen or a gas containing oxygen”, see Abstract, where the oxidation is performed in the presence of an iron catalyst, see Para. [0040]; Claim 41, and further separation of the produced aqueous stream by azeotropic distillation, see Paras. [0021]-[0022];[0087];[0089].
Regarding instant application claims 10 and 11, Bonnet teaches an amount of oxygen that is 1 times to 1000 times the molar content of the hydrocarbon compound to be oxidized of the mixture, see Paras. [0033];[0041];[0066], meeting and within the molar concentration range in instant application claim 10 and in instant application claim 11.
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 acetic acid feed solution and purification techniques of Tustin to use the bio-based crude acetic acid product mixture of Table 1, the bio-based acetic acid feed composition of Table 2, and/or the Table 3 distillation of bio-based acetic acid mixture and purification techniques of Horton, the bio-based acetic acid oxidation production method of Mostrou-Moser, and the oxidation concentrations of Bonnet, and to further distill/purify/flash evaporate to recover and separate any addition products from the crude product mixture including purified water as taught by Horton with a reasonable predictability of success for the purpose of producing an environmentally friendly acetic acid with reduced production costs, see Horton, Paras. [0039];[0059];[0060] and Mostrou-Moser, Pg. 1, Lns. 15-20; Pg. 5, Sixth Para.
By applying “routine optimization” and “predictable results” to select the optimal acetic acid feedstock and purification techniques, as taught by Horton, Mostrou-Moser, and Bonnet, one of ordinary skill in the art would have been motivated to make these modifications because Horton, Mostrou-Moser, and Bonnet provide a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to efficiently produce an acetic acid composition, such as via the use of bio-based materials and further purification techniques, for the benefit of producing an environmentally friendly acetic acid with reduced production costs, see Horton, Paras. [0039]; [0059];[0060] and Mostrou-Moser, Pg. 1, Lns. 15-20; Pg. 5, Sixth Para.
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 and published prior art are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Tustin, Horton, Mostrou-Moser, and Bonnet all teach the separation of acetic acid from an aqueous mixture in the organic acid aqueous mixture separation art, a person of ordinary skill in the art has good reason to modify Tustin by relying upon Horton, Mostrou-Moser, and Bonnet before the effective filing date of the claimed invention for knowledge generally available within the organic acid aqueous mixture production and separation art, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing an environmentally friendly acetic acid with reduced production costs, see Horton, Paras. [0039]; [0059];[0060] and Mostrou-Moser, Pg. 1, Lns. 15-20; Pg. 5, Sixth Para. and MPEP 2141.
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 re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929) states “[i]t is
a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions”, see MPEP 2144.05 II.A.
Selection of a known material, such as bio-based acetic acid and/or a ruthenium oxidation 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, “[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 % compounds in the feed mixtures, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), see MPEP 2144.05.
Further, “[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 distillation pressures, temperatures, and reactant concentrations, “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