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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 09 February 2026 has been entered.
Priority
This application is a 371 of PCT/US2020/60499 which claims the benefit of EP 20154275.0 and US Provisional 62/936,861 with an effective filing date of 18 November 2019 as reflected in the filing receipt mailed on 09 December 2022. It is noted, however, that applicant has not filed a certified copy of the EP 20154275.0 application as required by 37 CFR 1.55.
Status of the Claims
Claims 1-16 are currently pending.
Claim 16 is new.
Claims 1, 8, and 9 are currently amended.
Response to Amendments
Applicant’s amendments filed 09 February 2026 are acknowledged.
Claim Rejections - 35 USC § 103
Applicant’s amendments to claim 1 adding a first stage comprising the first catalyst and a second stage comprising the second catalyst are not taught by Diamond and are sufficient to overcome the rejections of:
Claims 1-7, 10, 11, and 13-15 under 35 U.S.C. 103 as being unpatentable over Diamond et al. (US20160090346, hereinafter Diamond) in view of Boussie et al. (US20100317823, hereinafter Boussie);
Claims 8 and 9 under 35 U.S.C. 103 as being unpatentable over Diamond et al. (US20160090346, hereinafter Diamond) in view of Boussie et al. (US20100317823, hereinafter Boussie), as applied to claims 1-7, 10, 11, and 13-15 in the 35 USC 103 rejection above, in further view of Weiner et al. (US20120157721, hereinafter Weiner); and,
Claim 12 under 35 U.S.C. 103 as being unpatentable over Diamond et al. (US20160090346, hereinafter Diamond) in view of Boussie et al. (US20100317823, hereinafter Boussie), as applied to claims 1-7, 10, 11, and 13-15 in the 35 USC 103 rejection above, in further view of Dakka et al. (US20100222609, hereinafter Dakka).
Due to the amendments to claim 1 the rejections are withdrawn and a new ground(s) of rejection is/are provided below.
Double Patenting
Applicant’s amendments to claim 1 adding a first stage comprising the first catalyst and a second stage comprising the second catalyst are not taught by the claims Albrecht or Diamond and are sufficient to overcome the rejections of:
Claims 1-7, 10, 11, and 13-15 on the ground of nonstatutory double patenting as being unpatentable over claims 1, 5, and 10-14 of U.S. Patent No. 12122745 to Albrecht et al. (hereinafter Albrecht) in view of Diamond et al. (US20160090346, hereinafter Diamond);
Claims 8 and 9 on the ground of nonstatutory double patenting as being unpatentable over claims 1, 5, 13, and 14 of U.S. Patent No. 12122745 to Albrecht et al. (hereinafter Albrecht) in view of Diamond et al. (US20160090346, hereinafter Diamond) and Weiner et al. (US20120157721, hereinafter Weiner); and,
Claim 12 on the ground of nonstatutory double patenting as being unpatentable over claims 1, 5, 13, and 14 of U.S. Patent No. 12122745 to Albrecht et al. (hereinafter Albrecht) in view of Diamond et al. (US20160090346, hereinafter Diamond) and Dakka et al. (US20100222609, hereinafter Dakka).
Due to the amendments to claim 1 the above nonstatutory double patenting rejections are withdrawn.
Response to Arguments
Applicant’s have not argued the merits of the nonstatutory double patenting rejections. The examiner is treating the current 09 February 2026 reply as “a bona fide attempt to advance the application to final action”, see MPEP 714.03. Therefore, Applicant’s arguments filed 09 February 2026 have been entered and have been fully considered but they are either moot or not persuasive.
Applicant’s argue that Diamond, Boussie, Weiner, and Dakka do not disclose the limitations as recited in amended claim 1. These arguments have been considered but are either moot or not persuasive for the reasons set forth in the new grounds of rejection below and the response to arguments below.
Applicant’s arguments throughout the remarks filed on 09 February 2026 with respect to Diamond have been considered but are moot because the new ground of rejection does not rely on Diamond applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Applicant’s arguments throughout the remarks filed on 09 February 2026 with respect to Weiner have been considered but are moot because the new ground of rejection does not rely on Weiner applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Applicant’s arguments throughout the remarks filed on 09 February 2026 with respect to Dakka have been considered but are moot because the new ground of rejection does not rely on Dakka applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
In response to applicant’s argument on page 6 of the remarks filed on 09 February 2026 that “[p]erforming the oxidation using distinct catalysts in different stages is not a mere rearrangement of parts, as concluded in Japikse.” The examiner is unaware of any Japikse reference or conclusion.
In response to applicant’s argument on page 6 of the remarks filed on 09 February 2026 that “Boussie likewise does not disclose performing oxidation of glucose to glucaric acid in separate stages.” Patents are part of the literature of the prior art, relevant for all they contain, see MPEP 2123. Boussie teaches “preparation of an adipic acid product includes chemocatalytic conversion of a glucose source to glucaric acid”, see Para. [0038], in the presence of oxidation catalysts, see Paras. [0088]-[0089]; Table 1, where the catalyst is “two of more metals (M1 and M2)” “supported on different support materials”, see Para. [0061], and the “catalysts mixtures (co-catalysts or mixed metal catalysts) containing more than one metal may affect separate steps of the mechanistic reaction pathway”, see Para. [0068], i.e., the oxidation reaction of glucose to glucaric acid is in separate stages applying mixtures of differing metal catalysts on differing supports in differing steps. Therefore, Boussie does teach performing oxidation of glucose to glucaric acid in separate stages.
For the reasons indicated above, applicant’s above argument is not persuasive.
In response to applicant’s argument on pages 7-8 of the remarks filed on 09 February 2026 that “Applicant achieved new and unexpected results relative to the prior art. The endpoint of Diamond (60%) and the maximum yield of Boussie (65%) are far below the glucaric acid yield achieved by Applicant (>80%)”. It is noted the endpoint glucaric acid yield is not instantly claimed.
The fact that the inventor has recognized another advantage which would flow naturally from following the suggestion of the prior art cannot be the basis for patentability when the differences would otherwise be obvious, see Ex parte Obiaya, 227 USPQ 58, 60 (Bd. Pat. App. & Inter. 1985). In addition, “[t]o establish unexpected results over a claimed range, applicants should compare a sufficient number of tests both inside and outside the claimed range to show the criticality of the claimed range” In re Hill, 284 F.2d 955, 128 USPQ 197 (CCPA 1960), see MPEP 716.02(d).
Please note: Instant application claim 1 has been amended to effectively nullify the reacting steps “(i) an aldose of formula (I) and/or lactone(s) thereof” and “(iii) a uronic acid of formula (III) and/or lactone(s) thereof” by adding “wherein the reacting further comprises: reacting the aldonic acid of formula (II) and/or the lactone(s) thereof in the presence of oxygen and the first catalyst in a first stage of the reaction zone to form a first reaction mixture comprising the uronic acid of formula (III) and/or the lactone(s) thereof; and contacting the first reaction mixture with oxygen and the second catalyst in a second stage of the reaction zone to form a second reaction mixture comprising the aldaric acid and/or the lactone(s) thereof of formula (IV)”. Therefore, the aldose and the uronic acid are no longer part of the claim 1 lines 3-12 first reacting step process. See the 35 USC 112(b) rejection below.
Instant application claim 1 is drawn to the oxidation reaction of the aldonic acid, gluconic acid, to the aldaric acid, glucaric acid, in separate stages applying differing metal catalysts on differing supports in differing stages. Applicant’s argue, as stated above, this reaction mechanism achieves “new and unexpected results relative to the prior art” regarding the “the glucaric acid yield”; however, Applicant’s have not provided a proper comparison to the closest prior art and have not established test points inside and outside the claimed range of the oxidation reaction of glucose to glucaric acid in separate stages applying differing metal catalysts on differing supports in differing stages in order to support the argument of surprising and unexpected results, see MPEP 716.02(e).
The instant specification is relied upon for any comparison tests/examples. Please note: The application contains two specifications both with 59 pages and both filed on 17 May 2022. Herein, the specification with the Para. [0001] priority information is the specification that is relied upon. See the objection to the specification below.
Glucose is converted to gluconic acid which is then converted to glucaric acid, see Paras. [0085]-[0087]. Table 1 details the oxidation reaction of gluconic acid with a Pt/C catalyst and a maximum glucaric acid yield of 65.2%. Table 2 details the oxidation reaction of gluconic acid with a Pt/TiO2 catalyst and a glucaric acid yield of 47.19%. Table 4 details the oxidation reaction of gluconic acid with a Pt-Au/TiO2 catalyst and a maximum glucaric acid yield of 56%. Table 5 details the oxidation reaction of gluconic acid with a mixture of Pt/C and Au/TiO2 catalyst and a maximum glucaric acid yield of 67.1%. Table 6 details varying the temperature and flow rate of the mixture of Pt/C and Au/TiO2 catalyst increases the maximum glucaric acid yield to 72.0. Table 7 details varying the temperature and pressure of the mixture of Pt/C and Au/TiO2 catalyst increases the maximum glucaric acid yield to 86.1%. The rest of the Examples and Tables do not appear to perform the instantly claimed oxidation reaction of gluconic acid to glucaric acid. Tables 6 and 7 detail the catalyst is not the only factor in increasing the glucaric acid yield. There appears to be no example of the instantly claimed oxidation reaction of gluconic acid to glucaric acid in separate stages applying differing metal catalysts on differing supports in differing stages. Therefore, the instant specification does not provide a comparison to the closest prior art and tests inside and outside the instantly claimed oxidation reaction of gluconic acid to glucaric acid in separate stages applying differing metal catalysts on differing supports in differing stages in order to support the argument of surprising and unexpected results relating to the glucaric acid yield, see MPEP 716.02(e).
In addition, Applicant’s argument of “the glucaric acid yield achieved by Applicant (>80%)” is the Table 7 oxidation reaction varying the temperature and pressure of the mixture of Pt/C and Au/TiO2 catalyst with the maximum glucaric acid yield of 86.1%. This appears to be the highest yield of glucaric acid obtained without the instantly claimed oxidation reaction of gluconic acid to glucaric acid in separate stages applying differing metal catalysts on differing supports in differing stages.
For all of the reasons indicated above, applicant’s above arguments are not persuasive.
New Rejections Based on Amendments to the Claims and the RCE filed on 09 February 2026
Specification
A substitute specification excluding the claims is required pursuant to 37 CFR 1.125(a) because the application contains two specifications both with 59 pages and both filed on 17 May 2022. The specifications are not the same. For example, one specification states “[0001] This application is a national stage entry of International Application No. PCT/US20/60499, filed November 13, 2020, which itself claims priority to U.S. Provisional Patent Application No. 62/936,861, filed November 18, 2019, and EP Patent Application No. 20154275.0, filed January 29, 2020, the contents of each are incorporated herein by reference”, and the other states “[0001] Various processes for preparing aldaric acids, aldonic acids, uronic acids, and/or lactone(s) thereof are described. For example, processes for preparing a C2-C7 aldaric acid and/or lactone(s) thereof by the catalytic oxidation of a C2-C7 aldonic acid and/or lactone(s) thereof and/or a C2-C7 aldose are described.” Herein, the specification with the Para. [0001] priority information is the specification that is relied upon.
A substitute specification clearly indicating the specification with the priority information in Para. [0001] is the accurate and current version of the specification is required.
A substitute specification must not contain new matter. The substitute specification must be submitted with markings showing all the changes relative to the immediate prior version of the specification of record. The text of any added subject matter must be shown by underlining the added text. The text of any deleted matter must be shown by strike-through except that double brackets placed before and after the deleted characters may be used to show deletion of five or fewer consecutive characters. The text of any deleted subject matter must be shown by being placed within double brackets if strike-through cannot be easily perceived. An accompanying clean version (without markings) and a statement that the substitute specification contains no new matter must also be supplied. Numbering the paragraphs of the specification of record is not considered a change that must be shown.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Claims 1-16 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Regarding claim 1, a broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired, see MPEP § 2173.05(c). In the present instance, the claim 1 lines 3-12 reacting recites the broad recitation “reacting (i) an aldose of formula (I) and/or lactone(s) thereof: HOCH2(HCOH)wCHO (I) wherein w is an integer from 0 to 10; or (ii) an aldonic acid of formula (II) and/or lactone(s) thereof: HOCH2(HCOH)xCOOH (II) where x is an integer from 0 to 10; or (iii) a uronic acid of formula (III) and/or lactone(s) thereof: HOOC(HCOH)yCHO (III) wherein y is an integer from 0 to 10”, and the claim also recites at the end “wherein the reacting further comprises: reacting the aldonic acid of formula (II) and/or the lactone(s) thereof in the presence of oxygen and the first catalyst in a first stage of the reaction zone to form a first reaction mixture comprising the uronic acid of formula (III) and/or the lactone(s) thereof; and contacting the first reaction mixture with oxygen and the second catalyst in a second stage of the reaction zone to form a second reaction mixture comprising the aldaric acid and/or the lactone(s) thereof of formula (IV)” which is the narrower statement of the range/limitation eliminating (i) an aldose and (iii) a uronic acid from the claim 1 lines 3-12 first reacting step. The claim is considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
Herein, the claim is interpreted to be drawn to only (ii) an aldonic acid in the claim 1 lines 3-12 first reacting step. The examiner suggests deleting reacting steps (i) and (iii) and placing the formula (III) in a different place within the claim, such as after the first stage first reaction mixture product recitation.
Regarding claim 1, the second to last line of page 1 of claim 1 recites “wherein in alternative (i) the reaction zone further comprises an oxidation catalyst”. As stated above, alternative (i) is nullified by the current amendment and the limitation appears to be redundant. Instant specification Para. [0081], states “various processes of the present invention can further comprise reacting an aldose (e.g., glucose) in the presence of oxygen and an oxidation catalyst. In these embodiments, the oxidation catalyst can include, for example, the first catalyst or second catalyst as described herein or any combination thereof. In some embodiments, the oxidation catalyst comprises the second catalyst as described herein.” The claim already states reacting aldose with a first catalyst and a second catalyst. The limitation is unclear as to whether the claim is drawn to an aldose reaction also with a third catalyst in a third catalytic reaction.
Claim 16 states “wherein a feed mixture comprising the aldose, the aldonic acid, the uronic acid, or the respective lactone(s) thereof”. As stated above, claim 1 is amended to only have a feed mixture of the aldonic acid. Therefore claim 16 lacks clarity.
Claims 2-16 depend from base claim 1 and are included in this rejection as they do not correct the informalities identified in base claim 1.
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, 5-11, and 13-15 are newly rejected under 35 U.S.C. 103 as being unpatentable over Boussie et al. (US20100317823, published 16 December 2010, hereinafter Boussie), as evidenced by Diamond et al. (US20160090346, published 31 March 2016, hereinafter Diamond), in view of Durndell et al. (“Cascade Aerobic Selective Oxidation over Contiguous Dual Catalyst Beds in Continuous Flow”, published 29 April 2019, ACS Catalysis, Vol. 9, Pgs. 5345-5352 and supporting information Pgs. S1-S17, hereinafter Durndell).
Boussie is in the known prior art field of “processes for the chemocatalytic conversion of a glucose source to an adipic acid product” by the “catalytic oxidation of glucose to glucaric acid or derivative thereof and processes comprising the catalytic hydrodeoxygenation of glucaric acid or derivatives thereof to an adipic acid product”, see Abstract, where “the oxidation reaction can be conducted in a batch, semi-batch, or continuous reactor design using fixed bed reactors, trickle bed reactors, slurry phase reactors, moving bed reactors, or any other design that allows for heterogeneous catalytic reactions”, see Para. [0028].
Regarding the limitations of instant application claim 1, Boussie teaches “reacting glucose with oxygen in the presence of an oxidation catalyst”, “wherein at least 50% of the glucose is converted to glucaric acid”, see Paras. [0017];[0020]-[0021], where the “preparation of an adipic acid product includes chemocatalytic conversion of a glucose source to glucaric acid”, see Para. [0038], in the presence of oxidation catalyst, see Paras. [0088]-[0089]; Table 1, where the catalyst is “two of more metals (M1 and M2)”, such as platinum and gold, “supported on different support materials”, see Paras. [0029]-[0034];[0061]-[0062], and the “catalysts mixtures (co-catalysts or mixed metal catalysts) containing more than one metal may affect separate steps of the mechanistic reaction pathway”, see Para. [0068], i.e., the oxidation reaction of glucose to glucaric acid is in separate stages applying mixtures of differing metal catalysts on differing supports in differing steps. As evidenced by Diamond, the catalytic conversion of glucose to glucaric acid with “at least platinum and gold as the catalytically active component” is known to have the following separate steps of the mechanistic reaction pathway:
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, see Diamond, Paras. [0098]-[0103], meeting:
The aldonic acid of formula (II) is gluconic acid and x is 4 in instant application claim 1;
The reaction takes place in the presence of oxygen in instant application claim 1;
The first catalyst comprises platinum, the second catalyst comprises gold, the catalysts differ, and the catalysts comprise differing supports in instant application claim 1;
The uronic acid of formula (III) is guluronic acid and y is 4 in instant application claim 1;
The aldaric acid of formula (IV) is glucaric acid and z is 4 in instant application claim 1;
The “oxidation reaction can be conducted in a batch, semi-batch, or continuous reactor design using fixed bed reactors, trickle bed reactors, slurry phase reactors, moving bed reactors, or any other design that allows for heterogeneous catalytic reactions”, where “[i]t should be understood that glucose, oxygen, any solvent, and the oxidation catalyst may be introduced into a suitable reactor separately or in various combinations”, see Para. [0028], “the oxidation catalyst comprises a heterogeneous catalyst”, see Claims 19, 22, 23, and 24, and, as stated above, the catalyst is “two of more metals (M1 and M2)”, such as platinum and gold, “supported on different support materials”, see Paras. [0061]-[0062], and the “catalysts mixtures (co-catalysts or mixed metal catalysts) containing more than one metal may affect separate steps of the mechanistic reaction pathway”, see Para. [0068], i.e., the oxidation reaction of glucose to glucaric acid is in separate stages applying mixtures of differing metal catalysts on differing supports in differing steps, meeting:
The reaction zones to form a mixture comprising the aldaric acid, glucaric acid, in instant application claim 1;
The second catalyst is a heterogenous catalyst in instant application claim 1; and,
A process for preparing the aldaric acid, glucaric acid, by reacting glucose with a catalyst, such as a mixture of platinum and gold on differing supports, to create the aldonic acid, gluconic acid, that is further reacted in another step with another catalyst mixture, such as gold and platinum on differing supports, i.e. first catalyst, to create the uronic acid, gluronic acid, that is further reacted with another catalyst mixture, such as platinum and gold on differing supports, i.e., second catalyst, to create the aldaric acid, glucaric acid, in instant application claim 1.
In addition, “[w]here applicant claims a composition in terms of a function, property or characteristic and the composition of the prior art is the same as that of the claim but the function is not explicitly disclosed by the reference, the examiner may make a rejection under both 35 U.S.C. 102 and 103”, see MPEP 2112 III. In this case, the catalytic conversion of glucose to glucaric acid with at least platinum and gold as the catalytically active component of Boussie will inherently result in the separate steps of the mechanistic reaction pathway as specifically evidenced by Diamond.
Regarding the limitations of instant application claims 2, 3, and 5-7, Boussie teaches, as stated above, “reacting glucose with oxygen in the presence of an oxidation catalyst”, “wherein at least 50% of the glucose is converted to glucaric acid”, see Paras. [0017];[0020]-[0021];[0038]. As evidenced by Diamond, the catalytic conversion of glucose to glucaric acid with “at least platinum and gold as the catalytically active component” is known to have the following separate steps of the mechanistic reaction pathway:
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, see Diamond, Paras. [0098]-[0103], meeting:
The aldonic acid of formula (II) is gluconic acid and x is 4 and the aldaric acid of formula (IV) is glucaric acid and z is 4 in instant application claim 2 and in instant application claim 7; and,
The C4 aldaric acid of formula (IV) is glucaric acid in instant application claim 3, in instant application claim 5, and in instant application claim 6.
Regarding the limitations of instant application claims 10 and 11, Boussie teaches “the oxidation catalyst comprises a first metal (M1) and a second metal (M2) at a surface of a support, wherein the M1 metal is selected from the group consisting of palladium and platinum and the M2 metal is selected from the group consisting of d-block metals, rare earth metals, and main group metals,” such as gold, “wherein the M1 metal is not the same metal as the M2 metal”, the “M1:M2 molar ratio may vary, for example, from about 500:1 to about 1:1”, and, “the weight percents of M1 and M2 relative to the catalyst weight may vary. Typically, the weight percent of M1 may range from about 0.5% to about 10%, more preferably from about 1% to about 8%, and still more preferably from about 2.5% to about 7.5% (e.g., about 5%). The weight percent of M2 may range from about 0.25% to about 10%, from about 0.5% to about 8%, or from about 0.5% to about 5%”, see Paras. [0029]-[0034];[0061]-[0062]. As stated above, the catalyst is “two of more metals (M1 and M2)”, such as platinum and gold, “supported on different support materials”, see Paras. [0061]-[0062], and the “catalysts mixtures (co-catalysts or mixed metal catalysts) containing more than one metal may affect separate steps of the mechanistic reaction pathway”, see Para. [0068], i.e., a mixture of Pt on a support and Au on a different support with a loading of Pt of about 0.5% to about 10% in the first catalyst stage and a mixture of Pt on a support and Au on a different support with a loading of Au of about 0.25% to about 10% on the second catalyst stage, meeting:
Within the range of the first catalyst Pt loading in instant application claim 10; and,
Within the range of the second catalyst Au loading in instant application claim 11.
Regarding the limitations of instant application claims 13-15, Boussie teaches “the temperature of the oxidation reaction mixture is at least about 40° C., more typically 60° C., or higher. In various embodiments, the temperature of the oxidation reaction mixture is from about 40° C. to about 150° C., from about 60° C. to about 150° C., from about 70° C. to about 150° C., from about 70° C. to about 140° C., or from about 80° C. or about 120° C.”, “the partial pressure of oxygen is at least about 15 pounds per square inch absolute (psia) (104 kPa), at least about 25 psia (172 kPa), at least about 40 psia (276 kPa), or at least about 60 psia (414 kPa). In various embodiments, the partial pressure of oxygen is up to about 1000 psia (6895 kPa), or more typically in the range of from about 15 psia (104 kPa) to about 500 psia (3447 kPa)”, aka 15 psig to 1000 psig, see Paras. [0025]-[0026], and “oxygen can be supplied to the reaction as air, oxygen-enriched air, oxygen alone, or oxygen with other constituents substantially inert to the reaction”, see Para. [0021], meeting:
Within the temperature range in instant application claim 13;
Within the pressure range in instant application claim 14; and,
The specific oxygen in instant application claim 15.
Regarding the limitations of instant application claims 8, and 9, Boussie teaches, as stated above, the catalyst is “two of more metals (M1 and M2)”, such as platinum and gold, “supported on different support materials”, see Paras. [0061]-[0062], and the “catalysts mixtures (co-catalysts or mixed metal catalysts) containing more than one metal may affect separate steps of the mechanistic reaction pathway”, see Para. [0068], where the “M1:M2 molar ratio may vary, for example, from about 500:1 to about 1:1”, see Para. [0031], i.e., a co-catalyst mixture of Pt on a support and Au on a different support with a loading of Pt of about 0.5% to about 10% and a co-catalyst mixture of Pt on a support and Au on a different support with a loading of Au of about 0.25% to about 10% in any stage with the molar ratio of the co-catalyst to each other of about 500:1 to about 1:1, meeting:
Physical mixtures of Pt-Au and Au-Pt catalysts within the weight or volume range in instant application claim 8 and in instant application claim 9.
Boussie does not specifically teach:
The instant application claim 1 limitations in one single express embodiment and the reaction stages; and,
The reaction stage limitations of instant application claims 8 and 9.
Durndell is in the known prior art field of “a sequence of packed catalyst beds” “to facilitate a cascade oxidation, whereby the downstream bed activates a molecular function produced over the upstream bed” “enabling the use of readily available catalysts that are selective for the individual steps”, see Abstract; Pgs. 5345-5346, Introduction; Scheme 1; Fig. 1, and is applied to teach the same.
Regarding the limitations of instant application claims 1, 8, and 9, Durndell teaches cascade catalytic oxidation reactions, where intermediates are produced and catalytically converted to achieve the final desired product, are performed in a continuous “flow across the PdPt sequential dual bed configuration”, see Fig. 1; Pg. 5346, Results and Discussion-Pg. 5348, First Col., Ln. 9, where the catalyst in each bed may be a mixture of Pd-Pt with differing loadings of each metal in the differing beds, see Pg. 5346, Scheme 1; Fig. 1; Pg. 5346, Results and Discussion-Pg. 5348, First Col. Ln. 9; Pg. S15, Table S2, meeting:
The differing physical mixtures of catalysts in differing sequential reaction beds in a continuous oxidation reaction in instant application claim 1, in instant application claim 8, and in instant application claim 9.
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 differing catalyst embodiments as taught by Boussie and to place the mixture of catalyst metal on differing supports with differing volumes/weights of each catalyst into the cascade oxidation sequence of packed catalyst beds as taught by Durndell with a reasonable predictability of success for the purpose of efficiently producing a cascade reaction product, such as glucaric acid, with a high single pass yield “and high stability for >14000 turnovers in the cascade oxidation” by judiciously ordering the catalysts so that the “intrinsic catalytic performance of each bed is preserved in the optimal dual-bed configuration, enabling quantitative prediction of final product yields for reactants/intermediates”, see Durndell, Abstract.
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying the mixture of catalyst metal on differing supports with differing volumes/weights of each catalyst oxidation reaction of Boussie by applying the known technique of the cascade oxidation sequence of packed catalyst beds as taught by Durndell with a reasonable predictability of success for the purpose of efficiently producing a cascade reaction product, such as glucaric acid, with a high single pass yield “and high stability for >14000 turnovers in the cascade oxidation” by judiciously ordering the catalysts so that the “intrinsic catalytic performance of each bed is preserved in the optimal dual-bed configuration, enabling quantitative prediction of final product yields for reactants/intermediates”, see Durndell, Abstract; and MPEP 2143 I. B-D.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Boussie and Durndell both teach cascade catalytic oxidation reactions, a person of ordinary skill in the art has good reason to modify Boussie by relying upon Durndell before the effective filing date of the claimed invention for knowledge generally available within the cascade catalytic oxidation reaction art regarding the placement of the catalyst beds, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing a cascade reaction product, such as glucaric acid, with a high single pass yield “and high stability for >14000 turnovers in the cascade oxidation” by judiciously ordering the catalysts so that the “intrinsic catalytic performance of each bed is preserved in the optimal dual-bed configuration, enabling quantitative prediction of final product yields for reactants/intermediates”; and, MPEP 2141 and 2143 I. B-D.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
“The 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 % metal loading, “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 an oxygen source, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
In addition, “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions,” such as mixtures of the catalysts with the desired weight/volume, and oxidation temperatures and pressures, “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.
Claim 4 is newly rejected and claim 16 is rejected under 35 U.S.C. 103 as being unpatentable over Boussie et al. (US20100317823, published 16 December 2010, hereinafter Boussie), as evidenced by Diamond et al. (US20160090346, published 31 March 2016, hereinafter Diamond), in view of Durndell et al. (“Cascade Aerobic Selective Oxidation over Contiguous Dual Catalyst Beds in Continuous Flow”, published 29 April 2019, ACS Catalysis, Vol. 9, Pgs. 5345-5352 and supporting information Pgs. S1-S17, hereinafter Durndell), as applied to claims 1-3, 5-11, and 13-15 in the 35 USC 103 rejection above, in further view of Diamond et al. (US20160090346, published 31 March 2016, hereinafter Diamond).
Boussie does teach:
The limitations of instant application claims 4 and 16.
Diamond is in the known prior art field of “various processes for preparing an aldaric acid by the selective oxidation of an aldose. Aldoses include, for example, pentoses and hexoses (i.e., C-5 and C-6 monosaccharides). Pentoses include ribose, arabinose, xylose, and lyxose, and hexoses include glucose, allose, altrose, mannose, gulose, idose, galactose, and talose. Generally, processes for the selective oxidation of an aldose to an aldaric acid comprise reacting the aldose with oxygen in the presence of an oxidation catalyst in an oxidation reaction zone to form an oxidation product comprising the aldaric acid”, see Para. [0089], and is applied to teach the same.
Regarding the limitations of instant application claim 4, Diamond teaches “various processes for preparing an aldaric acid by the selective oxidation of an aldose. Aldoses include, for example, pentoses and hexoses (i.e., C-5 and C-6 monosaccharides) … Pentoses include ribose, arabinose, xylose, and lyxose, and hexoses include glucose, allose, altrose, mannose, gulose, idose, galactose, and talose. … for the selective oxidation of glucose to glucaric acid and pentose to pentaric acid”, see Paras. [0089];[0129], meeting:
The specific aldaric acid, pentaric acid, in instant application claim 4.
Regarding the limitations of instant application claim 16, Diamond teaches a “30 wt. % solution of glucose was fed into the reactor under 2 different flow conditions”, see Paras. [0147]-[0149], meeting:
Within the aldose, glucose, feed to the reaction zone concentration range in instant application claim 16.
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 feed material and concentration of Boussie with the variety of aldose feeds and concentration as taught by Diamond with a reasonable predictability of success for the purpose of efficiently producing the desired aldose oxidation aldaric acid product “with enhanced overall process yield”, see Diamond, Paras. [0024];[0089]-[0091];[0112].
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying the feed material and concentration of Boussie by applying the known technique of the variety of aldose feeds and concentration as taught by Diamond with a reasonable predictability of success for the purpose of efficiently producing the desired aldose oxidation aldaric acid product “with enhanced overall process yield”, see Diamond, Paras. [0024];[0089]-[0091];[0112]; and MPEP 2143 I. B-D.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Boussie and Diamond both teach aldose oxidation reactions, a person of ordinary skill in the art has good reason to modify Boussie by relying upon Diamond before the effective filing date of the claimed invention for knowledge generally available within the aldose oxidation reaction art regarding the starting aldose feed and the concentration of the feed, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing the desired aldose oxidation aldaric acid product “with enhanced overall process yield”, see Diamond, Paras. [0024];[0089]-[0091];[0112]; and, MPEP 2141 and 2143 I. B-D.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
“The normal desire of scientists or artisans to improve upon what is
already generally known provides the motivation to determine where in a disclosed set
of percentage ranges”, such as the % concentration of the aldose feed, “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 the aldose feed to produce the desired aldaric acid product, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
In addition, “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions,” such as the % concentration of the aldose feed, “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.
Claim 12 is newly rejected under 35 U.S.C. 103 as being unpatentable over Boussie et al. (US20100317823, published 16 December 2010, hereinafter Boussie), as evidenced by Diamond et al. (US20160090346, published 31 March 2016, hereinafter Diamond), in view of Durndell et al. (“Cascade Aerobic Selective Oxidation over Contiguous Dual Catalyst Beds in Continuous Flow”, published 29 April 2019, ACS Catalysis, Vol. 9, Pgs. 5345-5352 and supporting information Pgs. S1-S17, hereinafter Durndell), as applied to claims 1-3, 5-11, and 13-15 in the 35 USC 103 rejection above, in further view of Bedard et al. (WO2008060985, published 22 May 2008, hereinafter Bedard).
Boussie teaches “[g]lucose can be obtained from various carbohydrate-containing sources including conventional biorenewable sources such as corn grain (maize), wheat, potato, cassava and rice as well as alternative sources such as energy crops, plant biomass, agricultural wastes, forestry residues, sugar processing residues and plant-derived household wastes”, see Para. [0019], and is used “as a feedstock to replace or supplement crude oil”, see Para. [0004].
Boussie does teach:
The limitations of instant application claim 12.
Bedard is in the known prior art field of “[o]xidation processes using a catalyst composition”, see Abstract, where the catalyst is homogeneous and heterogeneous catalysts containing platinum and gold, the reaction takes place in the liquid or in the gas phase, see Paras. [0008]-[0011];[0054], and the “[c]atalyst compositions are also useful for treating emissions (e.g., auto emissions, refinery emissions, utility plant emissions, etc.) and other process discharge streams for reducing the content of potentially harmful components that could adversely affect individual health or the environment”, see Paras. [0003]-[0007], and is applied to teach the same.
Regarding the limitations of instant application claim 12, Bedard teaches “a process comprising oxidation of a process stream using a catalyst composition to oxidize at least a portion of the process stream, the process stream comprising at least one compound having at least one oxidizable site”, see Para. [0023], where the “[p]rocess streams suitable for treatment with such oxidation processes, using the catalyst compositions of the type described above, generally include hydrocarbons with 1 to about 30 carbon atoms, including, without limitation, normal- and iso-alkanes, normal and iso-alkenes (whether monoenes or polyenes), normal- and iso-alkynes (whether monoynes or polyynes) and substituted aromatics and/or hetero-hydrocarbons with 1 to about 40 about carbon atoms and 1 to about 20 heteroatoms (e.g., N, S, O, etc.) … A process stream includes, without limitation, a feed stream, an intermediate transfer stream, a recycle stream and/or discharge stream”, see Paras. [00164]-[00167], and the “conditions for the oxidation process depend on the individual process application, and again, depending on the desired product, yield and/or process efficiency, can vary significantly, but for many oxidation processes, in which the catalyst compositions of the type described above can be used, suitable process conditions include: … (d) for selective oxidation, LHSV in the reactor generally ranging from about 0.1 hr-1 to about 50 hr-1 and for deep oxidation, GHSV in the reactor generally ranging from about 0.1 hr-1 to about 50 hr-1”, see Paras. [00166]-[00173], meeting:
Within the LHSV range for an oxidation reaction in instant application claim 12.
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 continuous oxidation reaction of recycled glucose of Boussie with the LHSV ranges as taught by Bedard with a reasonable predictability of success for the purpose of efficiently oxidizing a recycled hydrocarbon containing feed stream, such as glucose, in order to produce the desired product, such as an aldaric acid product, under “suitable process conditions” to obtain a high yield, see Bedard, Paras. [0003]-[0007];[00165]-[00173].
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying the continuous oxidation reaction of recycled glucose of Boussie by applying the known technique of the LHSV ranges as taught by Bedard with a reasonable predictability of success for the purpose of efficiently oxidizing a recycled hydrocarbon containing feed stream, such as glucose, in order to produce the desired product, such as an aldaric acid product, under “suitable process conditions” to obtain a high yield, see Bedard, Paras. [0003]-[0007];[00165]-[00173]; and MPEP 2143 I. B-D.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Boussie and Bedard both teach oxidizing a recycled hydrocarbon containing feed stream, a person of ordinary skill in the art has good reason to modify Boussie by relying upon Bedard before the effective filing date of the claimed invention for knowledge generally available within the oxidizing a recycled hydrocarbon containing feed stream art regarding the LHSV range, see MPEP 2143 B & G and 2141, for the benefit of efficiently oxidizing a recycled hydrocarbon containing feed stream, such as glucose, in order to produce the desired product, such as an aldaric acid product, under “suitable process conditions” to obtain a high yield, see Bedard, Paras. [0003]-[0007];[00165]-[00173]; and, MPEP 2141 and 2143 I. B-D.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
“It is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions,” such as the LHSV range, “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.
Relevant Art
Abashar et al. (“Investigation of low temperature decomposition of ammonia using spatially patterned catalytic membrane reactors”, published 2002, Applied Catalysis A: General, Vol. 236, Pgs. 35-53) teaches catalysts bed patterns, where the spatially layered beds have mixtures of catalysts in differing sections/stages of differing sizes and volumes, see Pg. 40, 6. Catalysts bed patterns; Fig. 2, and below.
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Conclusion
No claims are allowed.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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