DETAILED ACTION
STATUS OF THE APPLICATION
Receipt is acknowledged of Applicants’ Amendments and Remarks, filed 12 December 2025, in the matter of Application No. 18/797,010. Said documents have been entered on the record. The Examiner further acknowledges the following:
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 1-4, 6, 9, and 11-12 are pending.
Claims 1-2 have been amended.
Thus, claims 1-4, 6, 9, and 11-12 represent all claims currently under consideration.
Claim Interpretation
The phrase “hydrogen-to-ester ratio of hydrogen used in the hydrogenation reduction to the oligomer polyester is in a range of 80-200:1” as recited in instant claim 1 will be interpreted as a molar ratio of the hydrogen to the oligomer polyester, in a manner consistent with the written description (Specification; page 10, paragraph [0072]).
The term “hydrotalcite-like compound” as recited in instant claim 1 will be interpreted in the context of other conventional names for this class of synthetic catalytic solids, such as a layered double hydroxide (LDH), in a manner consistent with the known prior art (c.f., Zhou et al.; page 112, Col. 1, paragraph 3; Catal. Sci. Technol. 2011, 1, 111-122; PTO-892 of 9-12-2025).
REJECTIONS WITHDRAWN
The status for each rejection and/or objection in the previous Office Action is set out below.
35 U.S.C.§ 112(a)
Applicant’s amendments to the claims have fully overcome the rejections over instant claims 1-4, 6, 9, and 11-12.
REJECTIONS-MAINTAINED & MODIFIED
The below rejections are modified in view of the amendments to the claims. Modifications are bolded below.
MAINTAINED & MODIFIED Claim Rejections - 35 USC § 103 – Necessitated by Amendment
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.
Claims 1-4, 6, 9, and 11-12 remain rejected under 35 U.S.C. 103 as being unpatentable over Li et al. (Green Chem. 2023, 25, 627-638 with Supporting Information; published 12-13-2022; hereinafter “Li”), in view of M. Zhou et al. (CN 114524707 A; English language machine translation; PTO-892 of 9-12-2025; hereinafter “Zhou”), C.-H. Zhou et al. (Catal. Sci. Technol. 2011, 1, 111-122; PTO-892 of 9-12-2025; hereinafter “Zhou-2”), and N.G. Anderson (Practical Process & Research Development, 2000, pages 169-170; PTO-892 of 9-12-2025; hereinafter “Anderson”) (partially newly applied as necessitated by amendment).
Regarding claim 1, Li teaches the synthesis of bio-derived 1,4-butanediol (BDO) by succinic acid (SA) esterification and hydrogenation of CuFeAl catalysts (Li; Title). Li further teaches that SA can be produced on an industrial scale through the fermentation of bio-based intermediates, and therefore chemoselective hydrogenation of SA to bio-derived BDO is considered as a potentially sustainable route (Li; page 627, Col. 2, paragraph 2).
The process taught by Li comprises a first step involved in the production of BDO from bio-derived SA is esterification of SA with methanol to yield dimethyl succinate (DMS) and a second step of one-pot chemoselective hydrogenation of DMS to BDO over a Cu1Fe1Al0.5 catalyst that promotes the consecutive hydrogenation of bio-derived DMS to BDO (Li; Abstract; page 628, Col. 2, paragraphs 1-2). Li prepared and investigated ternary Cu-M-Al (M = Fe, Mg, Co, Ni, Sr, or Ba) catalysts derived from layered dihydroxyl hydroxide (LDH) precursors, wherein the Cu1Fe1Al0.5 catalyst displayed superior catalytic performance with 91.2% yield of BDO by segmented-temperature control (Li; page 628, Col. 1, paragraphs 2-3). In addition, Li teaches a preparation of ternary Cu1-M1-Al1-LDHs (M = Fe, Mg, Co, Ni, Sr, or Ba) precursors by a co-precipitation method using Cu1Fe1Al1 as an example: Cu(NO3)2·3H2O (10 mmol), Fe(NO3)2·6H2O (10 mmol), and Al(NO3)3·9H2O (10 mmol) were dissolved in 50 mL of deionized water to give a mixed salt solution; NaOH and Na2CO3 were dissolved in 50 mL of deionized water to form a mixed base solution; then, the metallic salt solution and the base solution were simultaneously added dropwise into a round-bottom flask and stirred at 50 °C for 5 h. The resulting brownish green precipitate was washed with deionized water until pH=7.0 and finally dried at 80 °C for 12 h. Next, the LDHs precursor was calcined in static air at 450 °C for 4 h to obtain Cu1Fe1Al1-mixed metal oxide (MMO), and the resultant Cu1Fe1Al1 catalyst was obtained after reduction in H2 at 350 ºC for 3 h; other Cu1M1Al1 and CuFeAl catalysts with different Cu/Fe/Al molar ratios (Cu/Fe/Al = 1/1/0.5 or 1/0.5/1) were also prepared using the similar procedures (Li; Supporting Information, page 3, Catalyst preparation). Li further characterized these catalysts by XRD and showed that all of the CuFeAl-LDHs showed diffraction lines corresponding to hydrotalcite-like materials (Li; page 632, Col. 1, paragraph 3). Thus, the skilled artisan could reasonably ascertain that the LDH construct taught by Li functions as a catalyst support, the CuFeAl-LDHs are ternary hydrotalcite-like compounds that are also supported copper-based catalysts, and the final reduction of the CuFeAl-LDHs in H2 comprises a catalyst activation step, in a manner consistent with instant claim 1. Finally, although Li teaches the use of copper nitrate trihydrate (i.e., Cu(NO3)2·3H2O) rather than copper nitrate hexahydrate, as recited in instant claim 1, one of ordinary skill could “at once envisage” the use of copper nitrate hexahydrate as a functional equivalent of copper nitrate trihydrate for use in the method of Li, and the close structural similarity would provide the expectation that these compounds will have similar properties. MPEP § 2144.09(I) states that “A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities.”
Li fails to teach (1) subjecting the mixture to esterification to obtain an oligomer polyester; (2) wherein a hydrogen-to-ester ratio of hydrogen used in the hydrogenation reduction to the oligomer polyester is in a range of 80-200:1; (3) a reactor temperature of 60 ºC; (4) wherein a pH value of the reaction system is maintained at a range of 8 to 10; (5) aging the precipitated product at 70 ºC for 24 h; (6) a calcination temperature of 500 ºC to 600 ºC; and (7) purifying the 1,4-BDO crude product to obtain the bio-based 1,4-BDO.
Regarding points (1), (6), and (7), Zhou teaches a method for preparing 1,5-pentanediol, characterized in that it comprises the following steps: esterifying a mixed dibasic acid and high-carbon fatty alcohol to obtain an esterification reaction liquid; under the conditions of a catalyst, the esterification reaction liquid is subjected to a hydrogenation reaction to obtain the 1,5-pentanediol (Zhou; Title; Abstract; claim 1; English language machine translation). Zhou further teaches that the mixed dibasic acid comprises succinic acid, glutaric acid, and adipic acid; and the post-treatment following the hydrogenation reaction includes sequentially performing a first distillation, a second distillation, and a third distillation to afford 1,4-butanediol, 1,5-pentanediol, and 1,6-hexanediol, respectively (Zhou; claims 2 and 10; paragraphs [0047]-0050]; English language machine translation). Thus, the method of Zhou also produces 1,4-butanediol from succinic acid and involves purifying the 1,4-BDO crude product, in a manner consistent with instant claim 1. Of particular note, Zhou teaches that the esterification reaction can cause the dibasic acid in the mixed dibasic acid and the alcohol in the high-carbon fatty alcohol to undergo an esterification reaction to form an oligomeric polyester diol with an average molecular weight of 500-1000, and the water generated by the esterification reaction will evaporate out of the reaction system at the esterification temperature (Zhou; paragraph [0039]; English language machine translation). In addition, Zhou teaches a hydrogenation catalyst comprising CuO and ZnO supported on an alumina carrier, wherein the catalyst is preferably obtained by an equal volume impregnation method comprising impregnating Al2O3 in a mixed solution of copper nitrate and zinc nitrate, and then drying and calcining in a sequence to obtain the catalyst, wherein the calcination temperature is preferably 400-600 ºC, and the catalyst is preferably subjected to hydrogenation activation before participating in the hydrogenation reaction (Zhou; claim 7; paragraphs [0042] and [0044]; English language machine translation). The calcination temperature range taught by Zhou overlaps with the range recited in the instant claim. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.” Finally, Zhou teaches several advantages to the method, including: the esterification reaction is carried out without a catalyst, so that catalyst separation after the esterification reaction is avoided; the operation is simple; and the esterification reaction feed liquid obtained by the esterification reaction is directly subjected to the hydrogenation reaction, so that separation and purification of the esterification reaction feed liquid are avoided, and the yields are improved; Zhong further compares the disclosed method to prior art that uses methanol as the reacting alcohol, wherein tedious steps such as solvent methanol recovery and distillation purification is required that lowers the overall product yield (Zhong; Abstract; paragraphs [0006], [0026], Examples 1-10 vs. Comparative Example 1).
Regarding points (4) and (5), Zhou-2 teaches the preparation of CuAlMg layered double hydroxide (LDH) materials, wherein a series of LDH materials were synthesized by simultaneous co-precipitation and hydrothermal treatments (Zhou-2; Abstract; page 112, Col. 2, paragraph 2, 2.1: Catalysts preparation). Of particular note, Zhou-2 teaches that typically, a mixture of MgCl2·6H2O (20.39 g, 0.10 mol) and AlCl3·6H2O (12.07 g, 0.05 mol), and the desired amount of Cu(NO3)2·3H2O was dissolved in 200 mL of deionized water; then, 2 M of NaOH aqueous solution was added to the above Mg–Al solution while stirring at 25 ºC until pH 10 was reached; the pH was then maintained by the continual addition of 0.2 M Na2CO3; thereafter, the resulting suspension was kept in a shaking water bath at 70 ºC for 24 h (Zhou-2; page 112, Col. 2, paragraph 2, 2.1: Catalysts preparation). Thus, Zhou-2 teaches the preparation of supported copper-based catalysts that are ternary hydrotalcite-like compounds in a manner consistent with instant claim 1. Of particular note, the adjustment of the pH up to pH 10 taught by Zhou-2 overlaps with the range recited in the instant claim. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.” In addition, the skilled artisan would reasonably interpret the method step of shaking the resulting suspension in a water bath at 70 ºC for 24 h as taught by Zhou-2 as an aging of the precipitated product, in a manner consistent with instant claim 1, wherein the temperature and time of aging read directly on the instant claim.
Regarding points (2) and (3), Anderson teaches that changing the proportion of reaction components, including changing the proportions of reaction components (e.g., change mole ratios), is a fundamental concept in practical chemical process optimization, as shown below (Anderson; page 169, Figure 8.5, part 1):
PNG
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415
1175
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Furthermore, Anderson reviews several conditions to vary for optimizing reactions, including the adjustment of temperature, and that increasing a reaction temperature usually increases the reaction rate (Anderson; page 169, Table 8.2; page 170, paragraph 4, ‘Optimizing Reaction Temperature’).
The prior art as taught by both Li and Zhou teach an esterification-hydrogenation production method for 1,4-butanediol from succinic acid using supported copper-based catalysts and thus reside in a closely overlapping technical field, such that the skilled artisan would be sufficiently motivated to incorporate the teachings of Zhou into the method of Li, especially since the method of Zhou teaches advantages compared to methods that employ an esterification reaction that uses a catalyst and with methanol as the reacting alcohol, as taught by Li. In addition, both Li and Zhou-2 reside in the overlapping technical field of supported copper-based catalysts that are ternary hydrotalcite-like compounds and their methods of preparation, such that the skilled artisan would be sufficiently motivated to incorporate the pH range adjustment and catalyst aging method steps of Zhou-2 into the method of Li with a reasonable expectation of success. This would result in a combination of prior art elements according to known methods to yield predictable results, as recited in MPEP § 2143(I)(A). Finally, the prior art as taught by both Li and Anderson reside in the overlapping technical field of synthetic organic chemistry processes, such that one of ordinary skill would be sufficiently motivated to incorporate the teachings of Anderson into the method of Li to achieve optimization of mole ratios of reactants in the hydrogenation step of Li and optimization of the reactor temperature of Li in the catalyst preparation step through means of routine experimentation. MPEP § 2144.05(II) states that “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” Therefore, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified Li to incorporate the teachings of Zhou, Zhou-2, and Anderson to implement (1) subjecting the mixture to esterification to obtain an oligomer polyester; (2) wherein a hydrogen-to-ester ratio of hydrogen used in the hydrogenation reduction to the oligomer polyester is in a range of 80-200:1; (3) a reactor temperature of 60 ºC; (4) wherein a pH value of the reaction system is maintained at a range of 8 to 10; (5) aging the precipitated product at 70 ºC for 24 h; (6) a calcination temperature of 500 ºC to 600 ºC; and (7) purifying the 1,4-BDO crude product to obtain the bio-based 1,4-BDO. The motivation to do so would yield the predictable results of combining prior art elements according to known methods, achieving reaction optimization through means of routine experimentation, and realizing a method wherein the esterification reaction is carried out without a catalyst, so that catalyst separation after the esterification reaction is avoided and the operation is simplified because the esterification reaction feed liquid obtained by the esterification reaction is directly subjected to the hydrogenation reaction, so that separation and purification of the esterification reaction feed liquid are avoided, and the yields are improved, as described above; this prior art combination further improves the method of Li wherein methanol is the reacting alcohol, wherein tedious steps such as solvent methanol recovery and distillation purification is required that lowers the overall product yield, as described above.
Regarding claim 2 depending from claim 1, Zhou teaches that the alcohol includes a monohydric alcohol or a dihydric alcohol, including butanol, pentanol, hexanol, and butanediol (Zhou; claim 4; paragraph [0035]; English language machine translation).
Regarding claim 3 depending from claim 1 and claim 11 depending from claim 2, Zhou teaches that the mass ratio of the mixed dibasic acid to the high-carbon aliphatic alcohol is 1:(1.1-1.6); furthermore, Zhou teaches that the mixed dibasic acid comprises succinic acid, glutaric acid, and adipic acid wherein the total mass percentage is preferably ≥ 99%, and the high-carbon alcohol includes a monohydric or dihydric alcohol, wherein the dihydric alcohol includes one or more of butanediol, 1,5-pentanediol, and hexanediol (Zhou; claims 2-5; English language machine translation). In addition, Zhou teaches a specific embodiment wherein the mass percentage of succinic acid in the mixed dibasic acid is 25%, the mass percentage of glutaric acid is 54%, and the mass percentage of adipic acid is 20% (Zhou; paragraph [0034]; English language machine translation). Thus, based on the teachings of Zhou, a 100 gram sample of this acid mixture would be reacted 110-160 grams of the high-carbon alcohol (e.g., butanediol); a 100 gram sample of the acid mixture according to the specific embodiment of Zhou detailed above would contain 0.2117 moles (25 g/118.09 g/mol) of succinic acid, 0.4087 moles (54 g/132.12 g/mol) of glutaric acid, and 0.1369 moles (20 g/146.14 g/mol) of adipic acid, for a total of 0.7573 moles; 110-160 grams of butanediol (i.e., 1,4-butanediol) corresponds to 1.221-1.775 moles (110 g/90.12 g/mol – 160 g/90.12 g/mol) of butanediol; overall, this corresponds to a diacid:butanediol molar ratio of 1-1.6-1.3, and this range overlaps significantly with the range recited in the instant claims. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.” Furthermore, one of ordinary skill incorporating the method of Zhou into the method of Li, as with claim 1 above, would be expected to implement this same molar ratio using the succinic acid starting material of Li and therefore, as with claim 1, it would have been prima facie obvious to combine Li, Zhou, Zhou-2, and Anderson and arrive at the claimed invention.
Regarding claim 4 depending from claim 1 and claim 12 depending from claim 2, Zhou teaches that the temperature of the esterification reaction is 90-220 ºC (Zhou; claim 6; English language machine translation). This temperature ranges overlaps with the range recited in the instant claims. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.” Although Zhou is silent regarding the esterification reaction time, Li teaches an esterification reaction time of 3 hours, which is close the range recited in the instant claims. MPEP § 2144.05(I) states that “a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.” Finally, Anderson reviews several conditions to vary for optimizing reactions, including the adjustment of temperature, and that increasing a reaction temperature usually increases the reaction rate, as detailed above (Anderson; page 169, Table 8.2; page 170, paragraph 4, ‘Optimizing Reaction Temperature’). Therefore, one of ordinary skill could reasonably arrive at the claimed range of reaction time based on the cited prior art and through means of routine experimentation. MPEP § 2144.05(II) states that “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” Therefore, as with claim 1, it would have been prima facie obvious to combine Li, Zhou, Zhou-2, and Anderson and arrive at the claimed invention.
Regarding claim 6 depending from claim 1, Zhou teaches that the temperature of the hydrogenation reaction is 100-220 ºC and the pressure is 1-20 MPa (Zhou; claim 9; English language machine translation). These temperature and pressure ranges read directly on the ranges recited in the instant claim. In addition, Li teaches optimization of reaction parameters on the one-pot hydrogenation reaction, including temperatures ranging from 170-250 ºC, pressures ranging from 1-6 MPa, and times ranging from 0-24 hours (Li; page 630, Fig. 2). These temperature, pressure, and time ranges overlap with the ranges recited in the instant claim. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.” Furthermore, the skilled artisan would recognize from these teachings that the hydrogenation reaction time is dependent on other reaction parameters (i.e., temperature and pressure) and therefore the instantly claimed reaction time range could be further arrived at through reaction optimization through means of routine experimentation. MPEP § 2144.05(II) states that “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” Therefore, as with claim 1, it would have been prima facie obvious to combine Li, Zhou, Zhou-2, and Anderson and arrive at the claimed invention.
Regarding claim 9 depending from claim 1, Li teaches molar ratios of the copper nitrate trihydrate (i.e., a functional equivalent and obvious variant of copper nitrate hexahydrate, as detailed above), the metal in the active metal salt (i.e., Fe), and the aluminum nitrate nonahydrate of 1:1:1, 1:1:0.5, and 1:0.5:1 (Li; Supporting Information, page 3, Catalyst preparation). These ratios read directly on the range recited in the instant claim.
Based on the combined teachings of the references, the Examiner submits that a person of ordinary skill in the art would have had a reasonable expectation of success of arriving at the instantly claimed method. Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, and absent a clear showing of evidence to the contrary.
Response to Arguments
Claim Rejections - 35 USC § 103
Applicant's arguments filed 12 December 2025, asserting that amended claim 1 is patentable over the combination of Li, Zhou, Zhou-2, and Anderson have been fully considered but they are not persuasive.
Applicant recites case law and MPEP sections pertinent to 35 USC § 103, and argues the following:
“Instant claim 1 is different from Li at least in that:
(1) in instant claim 1, the succinic acid from the bio-based source is derived from
biological fermentation, while Li is silent as to this feature; and
(2) in instant claim 1, a hydrogen-to-ester ratio of hydrogen used in the hydrogenation
reduction to the oligomer polyester is in a range of 80-200: 1, while Li is silent as
to this feature.
With regard to the distinguishing feature (1), Li only discloses that the succinic acid is a chemical reagent purchased from Shanghai Aladdin Biochemical Technology Co., LTD (see the first paragraph on page 1 in the supporting information of Li), implying that the succinic acid in Li is a chemical synthesis reagent. That is to say, Li does not teach or suggest that the succinic acid is derived from the bio-based source, let alone be derived from biological fermentation.
In the claimed invention, the succinic acid from a bio-based source has an extensive
source and is renewable, thus reducing carbon emissions and realizes recycling, utilizing biomass energy. The method cannot only increase an added value of the product, but also reduces environmental pollution, as well as brings considerable economic benefits.
Clearly Li is silent on the succinic acid derived from biological fermentation, much less the effects stemming from this. In view of this, Applicant submits that it is not obvious for one of ordinary skill in the art to select a succinic acid from the bio-based source from biological fermentation, let alone to know whether the succinic acid from the bio-based source from biological fermentation, as recited in instant claim 1, can increase the added value of the product.
Similarly, Zhou, Zhou-2, and Anderson do not teach or suggest that the succinic acid from the bio-based source is derived from biological fermentation. Thus, the other cited references do not cure the deficiencies of Li.”
This argument has been fully considered, but is not found to be persuasive. As detailed in the modified 103 rejection above, Li explicitly teaches that succinic acid can be derived from biological fermentation and is thus a useful starting material for the sustainable production of 1,4-butanediol (Li; page 627, Col. 2, paragraph 2). Furthermore, the process taught by Li comprises a first step involved in the production of BDO from bio-derived SA is esterification of SA with methanol to yield dimethyl succinate (DMS) and a second step of one-pot chemoselective hydrogenation that promotes the consecutive hydrogenation of bio-derived DMS to BDO (Li; Abstract; page 628, Col. 2, paragraphs 1-2). Finally, Applicant’s argument that the succinic acid is a chemical reagent purchased from Shanghai Aladdin Biochemical Technology Co., LTD is not persuasive, absent any evidence to the contrary, because Li specifically teaches SA as the bio-based source for bio-derived BDO, and therefore the skilled artisan would unambiguously realize the utility of bio-derived SA from biological fermentation as a sustainable starting material for BDO production. Furthermore, there does not appear to be any evidence that succinic acid obtained from “a bio-based source” derived from “biological fermentation” is chemically distinct from any other source of succinic acid. Nor does the claim actively require a step for obtaining the “bio-based” succinic acid. The term “bio-based” is only used passively to describe the source of the succinic acid, which will be chemically identical to any other source of succinic acid absent any evidence to the contrary. See MPEP § 2112.01. Therefore, the modified claim rejections are maintained for the reasons of record and the reasons set forth above.
Applicant argues the following:
“It can be seen from the examples of instant application, the bio-based 1,4-BDO prepared by the method, as recited in instant claim 1, has a purity of greater than or equal to 99.5%, a raw material conversion rate of greater than or equal to 99.5%, and a 1,4-BDO selectivity of greater than or equal to 98.0%. Thus, the technical solutions of instant claim 1 have produced a surprising and unexpected technical effect…
… It can be seen from the examples of instant application, the oligomer polyester has a conversion rate of greater than or equal to 99.5%, while the 1,4-BDO has a selectivity of greater than or equal to 98.0%, which proves that the catalytic activity of the catalyst has been significantly improved. Thus, the technical solutions as claimed in instant claim 1 have produced a surprising and unexpected technical effect.”
This argument has been fully considered, but is not found to be persuasive. The ranges recited by Applicant regarding the BDO purity, raw material conversion rate, and BDO selectivity are moot because these features are not recited in the rejected claims. 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).
Nevertheless, Li teaches reaction examples with raw material conversions of 100% and BDO selectivities of 99-100%, respectively (Li; page 631, Table 3). Therefore, based on the cited prior art, Applicant’s assertion of producing a surprising and unexpected technical effect is not persuasive. Therefore, the modified claim rejections are maintained for the reasons of record and the reasons set forth above.
Applicant argues the following:
“With regard to the distinguishing feature (2), Anderson only discloses that changing the proportion of reaction components (e.g., changing mole ratios) is a fundamental concept in practical chemical process optimization (see page 169, Figure 8.5, part 1). However, Anderson does not teach or suggest how to adjust the proportion of reaction components to improve the catalytic activity of the catalyst. In view of this, Applicant submits that it is not obvious for one of ordinary skill in the art to know how to adjust the proportion of reaction components, let alone which range can improve the catalytic activity of the catalyst.”
This argument has been fully considered, but is not found to be persuasive. Although the claim limitation of a hydrogen-to-ester ratio of hydrogen used in the hydrogenation reduction to the oligomer polyester is in a range of 80-200:1 is not explicitly taught in the recited prior art, Li teaches ranges of hydrogenation reaction temperature, pressure, and time that overlap with the ranges recited in the instantly claimed method (Li; page 630, Fig. 2), and Zhou also teaches a hydrogenation reaction temperature and pressure range identical to the ranges recited in the instantly claimed method (Zhou; claim 9; English language machine translation). Thus, the skilled artisan would recognize that there is an excess of hydrogen relative to the ester in the reaction solution, as is typical for hydrogenation reactions. The supporting teaching of Anderson is relied upon to further indicate that adjusting the proportions of chemical reagents is a common technique employed by one of ordinary skill and merely reflects a result of routine experimentation that is non-inventive in nature. MPEP § 2144.05(II).
Finally, absent any demonstration of criticality, there is no clear indication in the present application that the recited range for the hydrogen-to-ester ratio of hydrogen used in the hydrogenation reduction to the oligomer polyester is in a range of 80-200:1 is critical to the claimed invention, which would have supported the non-obviousness of the claimed ratio. None of the examples shown in the written description indicate instantly claimed the hydrogen-to-ester ratio, and there are no comparative examples clearly showing a special technical effect of said ratio. Therefore, it is unclear to what extent (if any) extent this parameter contributes to the criticality of the claimed invention, and as a result the present application does not clearly demonstrate a criticality for the range recited in amended claim 1. MPEP § 2144.05(III)(A) states that “The law is replete with cases in which the difference between the claimed invention and the prior art is some range or other variable within the claims… In such a situation, the applicant must show that the particular range is critical, generally by showing that the claimed range achieves unexpected results relative to the prior art range.”
Therefore, the modified claim rejections are maintained for the reasons of record and the reasons set forth above.
Conclusion
No claims are allowed.
Applicant’s amendment under 37 CFR 1.97(c) with the fee set forth in 37 CFR 1.17(p) on 12 December 2025 necessitated and prompted the maintained and modified ground(s) of rejection presented in this Office Action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any extension fee pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the Examiner should be directed to Derek Rhoades whose telephone number is (703)-756-5321. The Examiner can normally be reached Monday–Thursday, 7:30 am-5:00 pm EST; Friday, 7:30 am-4:00 pm EST.
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/D.R./Examiner, Art Unit 1692
/AMY C BONAPARTE/Primary Examiner, Art Unit 1692