DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Priority
This application is a 371 CON of PCT/CN2022/133407 which claims the benefit of CN 2022104345782 with an effective filing date of 24 April 2022 as reflected in the filing receipt mailed on 10 February 2023.
Status of the Claims
Claims 1-3 and 5-13 are pending.
Claims 11-13 are new.
Claims 1, 5, and 7 are currently amended.
Claim 4 is currently cancelled.
Response to Amendments
Applicant’s amendments filed 08 January 2026 are acknowledged.
Claim Objections
Applicant’s amendments to claims 1 and 7 and cancellation of claim 4 are sufficient to overcome the objections of the claims. Claim 1 and 7 have been amended to correct the grammatical mistakes. The objections are withdrawn.
Response to Arguments
Applicant’s arguments filed 08 January 2026 have been fully considered but they are not persuasive.
Applicant’s argue that Wang, Meng, Guo, Sahu, Zhang, and Okazaki do not disclose the limitations as recited in amended claim 1. These arguments have been considered but are not persuasive for the reasons set forth in the modified and new grounds of rejection below and the response to arguments below.
In response to applications arguments on page 7 of the remarks filed on 08 January 2026 that “the high dispersion of boric acid can be ensured, thereby enhancing catalytic activity. Moreover, it is beneficial to promoting the generation of esterification products and the separation, recovery and utilization of catalysts by the composite catalysts composed of active carbon and boric acid. i.e., yielding unpredictable result.”
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, [appellants] 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).
Newly amended instant application claim 1 states the previously unexamined limitations of “a composite catalyst composed of boric acid and activated carbon”. On pages 12-13 of the previous office action dated 29 October 2025 (hereinafter POA), Sahu was applied to teach a composite catalyst of boric acid and zeolite, rendering a composite catalyst of boric and activated carbon optionally moot.
Applicant’s argue, as stated above, the boric acid and activated carbon composite catalyst promotes “the generation of esterification products and the separation, recovery and utilization of catalysts by the composite catalysts composed of active carbon and boric acid. i.e., yielding unpredictable result”; however, Appellant’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 a composite catalyst composed of boric acid and activated carbon in order to support their argument of surprising and unexpected results, see MPEP 716.02(e).
The instant specification is relied upon for any comparison tests/examples. Embodiment 6 details “the catalyst is a composite catalyst composed of boric acid and activated carbon” resulting in properties of the esterification products “as follows: the purity is 99.8%, the yield is 96%, colorless, and the smell is aromatic”, see Paras. [0078]-[0083]. Embodiment 1 details the “catalyst is boric acid” resulting in properties of the esterification products “as follows: the purity is 99.5%, the yield is 98%, colorless, and the smell is aromatic”, see Paras. [0048]-[0053]. Embodiment 5 details “the catalyst is boric acid” resulting in properties of the esterification products “as follows: the purity is 99.0%, the yield is 90%, colorless, and the smell is aromatic”, see Paras. [0072]-[0077]. Embodiment 1 with only boric acid as the catalysts details substantially the same purity and a higher yield than Embodiment 6 with the composite catalyst comprising boric acid and activated carbon. These two embodiments do not provide support for an argument of surprising and unexpected results relating to the composite catalyst comprising boric acid and activated carbon.
In addition, applicants have not provided a comparison to the closest prior art relating to the composite catalyst comprising boric acid and activated carbon in order to support the argument of surprising and unexpected results relating to this composite catalyst, see MPEP 716.02(e).
For the reasons indicated above, applicant’s above arguments are not persuasive.
New and Modified Rejections Based on Amendments to the Claims in the reply filed on 08 January 2026
For clarity between the new, modified, and previous rejections, the specific new and modified rejections are in italics.
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 and 5-8 are newly rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN101314567, published 03 December 2008, see machine translation, hereinafter Wang) in view of Meng et al. (CN108640813, published 12 October 2018, see machine translation, hereinafter Meng) and Guo et al. (CN102351696, published 15 February 2012, hereinafter Guo), in further view of Zhu et al. (“B-doped activated carbon as a support for a high-performance Zn-based catalyst in acetylene acetoxylation”, published online 04 August 2020, Green Energy & Environment, Vol. 7, Pgs. 221-228, hereinafter Zhu).
Wang teaches the claims 1-3 and 6 limitations of a method for catalytic synthesis of a chiral compound, namely a tartrate, by utilization of boric acid, see Abstract. The method utilizes an acid-alcohol esterification reaction mechanism, where the synthesis steps are as follows: first, chiral 15 g tartaric acid and a desired alcohol, such as 27 ml/23.13 g n-pentanol, are mixed in a flask capable of oil-water separation, then 30 ml/25.86 g toluene used as a solvent and 0.5 g boric acid used as a catalyst are added with magnetic stirring and heating to the temperature of 70 ◦C, then 0.5 g boric acid is added every half hour for a duration of less than 6-7 hours, i.e., the next reflux step is for a certain amount of time, the following distillation steps are conducted for about 1-2 hours, and the total reaction time is 8-9 hours; also, since no pressure range is provided the stirring is inherently under normal pressure, see Paras. [0010];[0022]-[0034], and MPEP 2112, as calculated by the examiner a mass ratio of the alpha-hydroxycarboxylic acid : the alcohol : the catalyst : the water-carrying agent at up to 3 hours is 23.13 : 15 : 0.5-3.0 : 25.86 multiplied by 4.323 is 100 : (64.85) : (2.16 – 12.97) : (111.79), note: a zero lower ratio limit of the water-carrying agent implies the water-carrying agent may not be present, meeting:
The synthesis of alpha-hydroxycarboxylic acid ester, adding alpha-hydroxycarboxylic acid, alcohol, a catalyst and a water-carrying agent into a separator reaction device within the mass ratio under heated stirring for esterification and within the reaction time range, the specific catalyst, and the specific water-carrying agent in instant application claim 1;
The specific alpha-hydroxycarboxylic acid in instant application claim 2;
The specific primary alcohol with a C5 alkyl chain in instant application claim 3;
The mixture continues to separate and is refluxed until no more water is discharged into the upper layer, i.e., 100% of the water is in the upper layer, and toluene is in the lower layer, then the temperature is raised to 80 ◦C to distill off the n-pentanol and toluene until none are further distilled to obtain a crude product, see Paras. [0024];[0031]-[0032], meeting:
The reflux in instant application claim 1;
Within the range of the theoretical water yield of the esterification reaction and the distillation of the water-carrying and alcohol within the temperature range in instant application claim 6;
After the synthesis the unconverted tartaric acid in the distillation residue is recovered, and the separated residual liquid is concentrated or recycled several times until the boric acid reaches saturation, then boric acid is recovered by crystallization and directly returned to the process, see Para. [0029], meeting most of step (2) in instant application claim 1;
The crude product is washed, dried, and distilled under reduced pressure, cooled, and the product n-pentyl tartrate is obtained, see Paras. [0025]-[0027];[0032]-[0033], and the toluene is recovered and recycled, see Paras. [0011];[0032], meeting the vacuum fractionation, water-carrying agent recycle, and obtained product of step (4) in instant application step 1.
Wang does not teach:
The instant application claim 1 limitations of step (1), performing an esterification reaction at a temperature in a range of 100-160 Celsius degrees (°C);
step (3), neutralization and water washing, comprising: washing the filtered product obtained in the step (2) to neutral with water, or neutralizing the filtered product with an aqueous solution of sodium carbonate and then washing with water, to thereby obtain a neutral esterification product;
step (4), the neutral esterification product obtained in the step (3); and,
The vacuum distillation in instant application claims 6 and 7.
Meng relates to a method for synthesizing terpinyl acetate from the esterification of turpentine, glacial acetic acid, water, alpha-hydroxycarboxylic acid, and a cocatalyst, such as acetic anhydride, see Abstract; Paras. [0019];[0250]. The esterification is carried out by adding turpentine, glacial acetic acid, lactic acid and boric acid in a mass ratio of 100:200:18:12 or turpentine oil, glacial acetic acid, L-malic acid, boric acid, zinc sulfate and acetic anhydride in a mass ratio of 100:300:30:10:2 into a reactor with stirring at a temperature from 12-100 ◦C, see Paras. [0012];[0019];[0042];[0081], meeting and within the esterification temperature range in instant application claim 1;
The synthesis includes after esterification the recovered product layer is sent to a water washing tank and neutralized with sodium carbonate water, followed by further washing with water 2-3 times to obtain a crude product containing neutralized terpineol acetate, see Paras. [0012]-[0014];[0057], meeting step (3) and the neutralized product of step (4) in instant application claim 1;
The synthesis includes the use of acetic acid as a catalysts, where after the reaction is completed, the synthesized product is transferred to a freezing tank and cooled to ≤10 ◦C, to crystallize unreacted acetic acid in the system, then the reaction solution and the acetic acid crystals are filtered to separate, then the acetic acid crystals are subjected to low-temperature centrifugation at a temperature of ≤5°C, where the centrifuged acetic acid crystals are used as a raw material for the next reaction and the centrifuged liquid is mixed with the filtrate to obtain the target product containing terpineol acetate, see Para. [0043], meeting step (2), catalyst recovery, comprising: cooling the crude product filtering out the catalyst to obtain a filtered product and centrifugal drying the catalyst in instant application claim 1;
The distillation is performed by vacuum distillation to make the vacuum degree in the distillation tower ≤-0.09MPa, see Paras. [0024]-[0025], meeting and within the range of pressure in instant application claim 6; and,
The distillation by vacuum fractionation includes:
S4: heating the tower to maintain the bottom temperature at 120-130 ◦C and the top temperature at 90-105 ◦C, with a reflux ratio of 20:1, and collecting the intermediate fractions of borneol, fenchol, terpineol, and fenchyl acetate;
S5: Increase the vacuum degree in the tower to ≤-0.1MPa, maintain the tower bottom temperature at 130-155 ◦C, maintain the tower top temperature at 110-120 ◦C, and collect the tower top product as pine acetic acid at a reflux ratio of 15:1, see Paras. [0046]-[0051], meeting:
The distillation of acetic acid and residuals, such as acetic anhydride, in instant application claim 7.
Wang and Meng do not teach:
The instant application claim 1 limitations of step (2), catalyst recovery, comprising: cooling the crude product to a room temperature, and wherein the fractionated alcohol is used for a next reaction; and,
The specific acetylation reaction limitations in instant application claims 7 and 8.
Guo relating to synthesizing citrate by adding citrate, alcohol and a catalyst into a reactor for esterification and performing an acylation reaction while recovering and reusing waste, see Abstract; Para. [0010]. Guo exemplifies the prior art synthesis of citrate by step 1. adding citric acid, n-butanol, and sodium bisulfate monohydrate to a reactor, stirring and reacting under reflux, cooling and filtering to recover the catalyst, i.e., cooling implies cooling at least to room temperature, see MPEP 2112, adding an alkaline solution to the filtrate for neutralization, washing with water until neutral, recovering the n-butanol by atmospheric distillation, and removing residual water by reduced pressure distillation to obtain a crude tributyl citrate product, see Para. [0008] and MPEP 2123 stating ““[t]he use of patents as references is not limited to what the patentees describe as their own inventions or to the problems with which they are concerned. They are part of the literature of the art, relevant for all they contain.” In re Heck, 699 F.2d 1331, 1332-33, 216 USPQ 1038, 1039 (Fed. Cir. 1983)”, meeting within the temperature range of cooling the crude product and recovering the alcohol in instant application claim 1;
Then in step 2. a composite decolorizing agent of activated carbon and aluminum oxide are added to the cooled reaction mixture for decolorization to obtain a finished tributyl citrate product mixture, then to the finished tributyl citrate product mixture, acetic anhydride, and the catalysts sodium bisulfate monohydrate are added with stirring and reacted at 60-90 ◦C for 1.0-3.5 hours, followed by cooling and filtering to recover the catalyst and the activated carbon, where the acetic anhydride, activated carbon, and a catalyst are added in step 1. before the alcohol is recovered, then reduced pressure/vacuum distillation to recover the product, see Paras. [0008];[0014]-[0018]. The molar ratio of the (hydrated) citric acid to the acetic anhydride is 1:1-2, see Para. [0022], and the amount of the catalyst added during the acetylation is 0.005% to 2.0% of the mass of the finished citrate ester, see Para. [0019], meeting:
The acetylation reaction and within the ranges of the acetylation reaction in instant application claim 7; and,
Within the sodium bisulfate range in instant application claim 8.
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 Wang to adjust the esterification reaction temperature based on the reactants to esterify, see MPEP 2144.05 II., to neutralize the product, to recover the catalysts, and vacuum distill/fractionate as taught by Meng with a reasonable predictability of success for the purpose of efficiently esterifying an alpha-hydroxycarboxylic acid using a simple industrial production process that has a low emission of wastes, low corrosion, no toxicity, and is environmental friendly, see Meng, Abstract, Paras. [0005];[0009].
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 Wang to adjust the catalyst recovery cooling temperature, see MPEP 2144.05 II., to recover and reuse the alcohol, and to also acetylate the reactants as taught by Guo with a reasonable predictability of success for the purpose of efficiently esterifying an alpha-hydroxycarboxylic acid using an integrated simple industrial production process that has a low emission of wastes, a short production period, low cost, and is environmental friendly, see Guo, Abstract, Paras. [0005];[0028].
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 Wang, Meng, and Guo all teach the catalytic esterification of an alpha-hydroxycarboxylic acid, a person of ordinary skill in the art has good reason to produce an alpha-hydroxycarboxylic acid ester, by pursuing the known options within their technical grasp for the benefit of efficiently esterifying an alpha-hydroxycarboxylic acid using an integrated simple industrial production process that has a low emission of wastes, a short production period, low cost, and is environmental friendly, see Guo, Abstract, Paras. [0005];[0028], Meng, Abstract, Paras. [0005];[0009], 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.
Selection of a known material, such as recovery and recycle of reactants, 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 regard to the selection of reaction temperatures, reaction times, vacuum distillations, and pressures, “[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”, In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929), see MPEP 2144.05.
Wang does not teach the newly amended instant application claim 1 limitations of “a composite catalyst composed of boric acid and activated carbon”; and,
The limitations of claim 5.
Zhu is in the known prior art field of boron doped activated carbon containing catalysts for the conversion of carboxylic acid containing hydrocarbons, see Abstract; Pg. 222, Eq. 1, Col. 1; Pg. 223, 2.3. Catalytic performance test -Pg. 224, 3.2. The effect of B-doping for the catalyst, Table 1.
Regarding the limitations of instant application claims 4 and 5, Zhu teaches a boron-doped activated carbon catalyst is prepared by “[f]irstly, 0.1 g boric acid was dissolved in 20 mL deionized water. Subsequently, 10 g of AC was added to the solution and the reaction mixture was stirred for 24 h before drying for 12 h at 60 C. A series of B-doped AC was prepared by addition of 0.05–0.4 g of boric acid. The as-prepared B-doped AC were named 0.005 B-AC, 0.01 B-AC, 0.015 B-AC, 0.02 B-AC and 0.04 B-AC, according to their respective mass ratios.”, see Pg. 222, 2.1. Catalyst preparation. The prepared boron doped activated carbon containing catalysts are then applied in a reaction for the conversion of carboxylic acid containing hydrocarbons, see Abstract; Pg. 222, Eq. 1, Col. 1; Pg. 223, 2.3. Catalytic performance test -Pg. 224, 3.2. The effect of B-doping for the catalyst, Table 1, where the B-doped activated carbon provides for enhanced adsorption of the carboxylic acid and reduced adsorption of the desired reaction species; while, increasing the conversion rate of the carboxylic acid, see Abstract; Pgs. 223-224, 3.2. The effect of B-doping for the catalyst, Table 1, meeting the boron activated composite catalyst limitations in instant application claim 1.
In regard to the instant claim 5 limitations of “wherein the composite catalyst is prepared by …”, see MPEP 2113(I) stating ““even though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process.” In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985) (citations omitted)”. Zhu teaches the product composite catalyst; therefore, the process of production is not given patentable weight, meeting the limitations in instant application claim 5.
[deleted]
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 Wang to use the boric acid activated carbon composite catalyst as taught by Zhu with a reasonable predictability of successfully providing for enhanced adsorption of the carboxylic acid and reduced adsorption of the desired reaction species; while, increasing the conversion rate of the carboxylic acid, see Abstract; Pgs. 223-224, 3.2. The effect of B-doping for the catalyst, Table 1.
The 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. One of ordinary skill in the art would have been capable of modifying the boric acid catalyst of Wang by applying the known technique of the impregnation of boric acid into activated carbon as taught by Zhu with a reasonable predictability of success for the purpose of providing for enhanced adsorption of the carboxylic acid and reduced adsorption of the desired reaction species; while, increasing the conversion rate of the carboxylic acid, see Abstract; Pgs. 223-224, 3.2. The effect of B-doping for the catalyst, Table 1; 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 Wang and Zhu both teach the use boric acid as a catalyst in the conversion of carboxylic acid containing hydrocarbons, a person of ordinary skill in the art has good reason to modify Wang by relying upon Zhu before the effective filing date of the claimed invention for knowledge generally available within the boric acid hydrocarbon conversion catalyst art regarding the desired boric acid support, see MPEP 2143 B & G and 2141, for the benefit of providing for enhanced adsorption of the carboxylic acid and reduced adsorption of the desired reaction species; while, increasing the conversion rate of the carboxylic acid, see Abstract; Pgs. 223-224, 3.2. The effect of B-doping for the catalyst, Table 1; and MPEP 2143 I. B-D; 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.
Selection of a known material, such as a boric acid activated carbon catalyst composite, 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.
Claim 9 is newly rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN101314567, published 03 December 2008, see machine translation, hereinafter Wang) in view of Meng et al. (CN108640813, published 12 October 2018, see machine translation, hereinafter Meng) and Guo et al. (CN102351696, published 15 February 2012, hereinafter Guo), in further view of Zhu et al. (“B-doped activated carbon as a support for a high-performance Zn-based catalyst in acetylene acetoxylation”, published online 04 August 2020, Green Energy & Environment, Vol. 7, Pgs. 221-228, hereinafter Zhu), as applied to claims 1-3 and 5-8 in the 35 USC 103 rejection above, and in further view of Zhang (CN106381191, published 08 February 2017, see machine translation).
Wang does not teach the limitations of instant application claim 9.
Zhang relating to the drying of a boron containing catalyst problem to be solved, see MPEP 2143 B & G, teaches drying boric acid to powdery crystal form by heating at a temperature 110-120 ◦C for 2-3 hours, see Paras. [0032];[0047], meeting and within the ranges in instant application claim 9.
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 Wang to dry the boric acid as taught by Zhang with a reasonable predictability of success for the purpose of efficiently recovering and recycling the boric acid into dry powdery crystals without lumps in order to increase the reactive surface area of the boric acid, see Zhang, Paras. [0032];[0047].
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 Wang teaches recovery of a boric acid catalyst with crystallization and Zhang teaches drying boric acid to powdery crystals, a person of ordinary skill in the art has good reason to solve the problem of drying boric acid by pursuing the known options within their technical grasp for the benefit of efficiently recovering and recycling the boric acid into dry powdery crystals without lumps in order to increase the reactive surface area of the boric acid, see Zhang, Paras. [0032];[0047], MPEP 2141, and MPEP 2143 B & G.
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.
Claim 10 is newly rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN101314567, published 03 December 2008, see machine translation, hereinafter Wang) in view of Meng et al. (CN108640813, published 12 October 2018, see machine translation, hereinafter Meng) and Guo et al. (CN102351696, published 15 February 2012, hereinafter Guo), in further view of Zhu et al. (“B-doped activated carbon as a support for a high-performance Zn-based catalyst in acetylene acetoxylation”, published online 04 August 2020, Green Energy & Environment, Vol. 7, Pgs. 221-228, hereinafter Zhu), as applied to claims 1-3 and 5-8 in the 35 USC 103 rejection above, and in further view Okazaki et al. (US20100022740, hereinafter Okazaki).
Wang does not teach the limitations in instant application claim 10.
Meng teaches the distillation is by the vacuum fractionation steps of:
S1: First, exhaust the air from the distillation tower to make the vacuum degree in the distillation tower ≤-0.09MPa;
S2: drying the preliminarily refined terpineol acetate product and transporting it to the reactor of a distillation tower;
S3: heating to maintain the bottom temperature at 100-120 ◦C and the top temperature at 70-90°C, reflux for 1 hour, and collect the front fractions of ramie and terpinene at a reflux ratio of 12:1, which will also collect the water-carrying agent and unreacted alcohol;
S4: heating the tower to maintain the bottom temperature at 120-130 ◦C and the top temperature at 90-105 ◦C, with a reflux ratio of 20:1, and collecting the intermediate fractions of borneol, fenchol, terpineol, and fenchyl acetate;
S5: Increase the vacuum degree in the tower to ≤-0.1MPa, maintain the tower bottom temperature at 130-155 ◦C, maintain the tower top temperature at 110-120 ◦C, and collect the tower top product as pine acetic acid at a reflux ratio of 15:1, see Paras. [0046]-[0051], meeting and within the ranges of steps S1-S4 in instant application claim 10.
Guo teaches in step 1. adding citric acid, n-butanol, and sodium bisulfate monohydrate to a reactor, stirring and reacting under reflux, cooling and filtering to recover the catalyst, i.e., cooling implies cooling at least to room temperature, see Para. [0008] and MPEP 2112, and in step 2. a composite decolorizing agent of activated carbon and aluminum oxide are added to the cooled reaction mixture for decolorization to obtain a finished tributyl citrate product mixture, then to the finished tributyl citrate product mixture, acetic anhydride, and the catalysts sodium bisulfate monohydrate are added with stirring and reacted at 60-90 ◦C for 1.0-3.5 hours, followed by cooling and filtering to recover the catalyst and the activated carbon, where the acetic anhydride, activated carbon, and a catalyst are added in step 1. before the alcohol is recovered, then reduced pressure/vacuum distillation to recover the product, see Paras. [0008];[0014]-[0018], meeting most of step S5 in instant application claim 10.
Okazaki relating to the decolorization problem to be solved, see MPEP 2143 B & G, teaches the decolorization of a glycolate mixture through use of activated carbon in the solution, heating, and stirring for a sufficient amount of time, then the recovered supernatant was vacuum filtered to remove powdered activated carbon particles, where the amount of activated carbon used is preferably reduced as much as possible from the economical point of view and is not more than 20 weight % based on the solution containing a glycolate which the activated carbon is added, more suitably from 1 to 12.5 weight %, see Paras. [0100]-[0101];[0164], meeting and within the range of the activated carbon and pressure filtration separation of step S5 in instant application claim 10.
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 Wang to use the vacuum filtration fractionation as taught by Meng and the activated carbon decolorization as taught by Guo and Okazaki, with a reasonable predictability of success for the purpose of efficiently esterifying an alpha-hydroxycarboxylic acid to produce an alpha-hydroxycarboxylic acid ester of excellent color using an integrated simple industrial production process that has a low emission of wastes, a short production period, low cost, and is environmental friendly, see Guo, Abstract, Paras. [0005];[0028], Meng, Abstract, Paras. [0005];[0009]; Okazaki, Paras. [0061];[0164].
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 Wang, Guo, Meng, and Okazaki all teach the purification of an alpha-hydroxycarboxylic acid ester, a person of ordinary skill in the art has good reason to purify an alpha-hydroxycarboxylic acid ester, by pursuing the known options within their technical grasp for the benefit of efficiently esterifying an alpha-hydroxycarboxylic acid to produce an alpha-hydroxycarboxylic acid ester of excellent color using an integrated simple industrial production process that has a low emission of wastes, a short production period, low cost, and is environmental friendly, see Guo, Abstract, Paras. [0005];[0028], Meng, Abstract, Paras. [0005];[0009]; Okazaki, Paras. [0061];[0164], MPEP 2141, and MPEP 2143 B & G.
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 regard to the selection of reaction temperatures, reaction times, vacuum distillations, and pressures, “[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”, In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929), see MPEP 2144.05.
Claims 11-13 are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (CN101314567, published 03 December 2008, see machine translation, hereinafter Wang ‘567) in view of Meng et al. (CN108640813, published 12 October 2018, see machine translation, hereinafter Meng) and Guo et al. (CN102351696, published 15 February 2012, hereinafter Guo), in further view of Zhu et al. (“B-doped activated carbon as a support for a high-performance Zn-based catalyst in acetylene acetoxylation”, published online 04 August 2020, Green Energy & Environment, Vol. 7, Pgs. 221-228, hereinafter Zhu), as applied to claims 1-3 and 5-8 in the 35 USC 103 rejection above, and in further view of Wang et al. (CN10131566, published 03 December 2008, see machine translation, hereinafter Wang ‘566).
Wang ‘567 is in the known prior art field of “a chemical synthesis method, in particular to a method for catalytic synthesis of a chiral compound,
namely n-Amyl tartrate, by utilization of boric acid,” see Abstract.
Regarding the limitations of instant application claim 11, Wang ‘567 teaches to synthesis the tartrate “chiral tartaric acid is mixed with required alcohol” “and the mixture ratio is different according to the variety of the synthesized chiral tartrate and then the mol ratio is different”, then “the chiral n-Amyl tartrate is obtained by adoption of toluene as solvent and the boric acid as catalyst”, see Abstract; Paras. [0008];[0010]-[0014], meeting tartaric acid and toluene in instant application claim 11.
Wang ‘567 does not teach:
The instant application claim 11 limitations of butanol and dibutyl tartrate; and,
The instant application claim 12 specific mass ratio.
Wang ‘566 is in the known prior art field of “a chemical synthesis method, in particular to a method for catalytic synthesis of a chiral compound, namely n-butyl tartrate, by utilization of boric acid” see Abstract, n-butyl tartrate aka dibutyl tartrate.
Regarding the limitations of instant application claim 11, Wang ‘566 teaches to synthesis “the chiral source compound n-butyl tartrate using boric acid” “[t]he synthesis steps are as follows: First, chiral tartaric acid and the desired alcohol, such as n-butanol, are mixed. The mixing ratio varies depending on the type of chiral tartaric acid ester being synthesized. Then, toluene is used as the solvent and boric acid as the catalyst.”, see Paras. [0010]-[0014], meeting the tartaric acid, the butanol, the toluene, and n-butyl tartrate aka dibutyl tartrate in instant application claim 11.
Regarding the limitations of instant application claim 12, Wang ‘567 teaches “[t]he mixing ratio and the molar ratio vary depending on the type of chiral tartaric acid ester to be synthesized”, where one mixing ratio synthesis is to “[w]eigh 15g (0.1mol) of tartaric acid into a three-necked flask, then weigh 27ml of n-pentanol and 30ml of toluene and mix well; weigh 0.5g of boric acid and add it to the flask; start heating, control the temperature of the magnetic stirrer to 70℃; then add 0.5g of boric acid every half hour”, see Paras. [0010]-[0014];[0020];[0022];[0031];[0034], as calculated by the examiner, 15 g of tartaric acid : 0.811 g/ml x 27 ml is 21.90 g n-pentanol : 0.863 g/ml x 30 is 25.89 g of toluene : 0.5 g boric acid.
Regarding the limitations of instant application claim 12, Wang ‘566 teaches “[t]he mixing ratio and the molar ratio vary depending on the type of chiral tartaric acid ester to being synthesized”, where one mixing ratio synthesis is to “[w]eigh 15g (0.1mol) of tartaric acid and add it to a three-necked flask. Then, measure 36ml of n-butanol and 30ml of toluene and add them to the flask, mixing thoroughly. Weigh 0.5g of boric acid and add it to the flask. Start heating, controlling the temperature of the magnetic stirrer at 70℃. Then, add 0.5g of boric acid every half hour”, see Paras. [0010]-[0014];[0020];[0022];[0031];[0034], as calculated by the examiner, 15 g of tartaric acid : 0.811 g/ml x 36 ml is 29.20 g n-butanol : 0.863 g/ml x 30 is 25.89 g of toluene : 0.5 g boric acid.
Since “a prima facie case of obviousness exists” where the claimed ranges or amounts do not overlap with the prior art but are merely close, see MPEP 2144.05, one of ordinary skill in the art, before the effective filing date of the claimed invention, would be able to predictably utilize the teachings of Wang ‘567 and Wang ‘566 to determine the variations in the mixing ratio and the molar ratio depending on the type of chiral tartaric acid ester being synthesized, meeting within the specific mass ratio 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 reactants based upon the desired tartrate to be synthesize of Wang ‘567 to choose butanol as the desired alcohol in order to synthesis dibutyl tartrate as taught by Wang ‘566 with a reasonable predictability of successfully synthesizing the desired “type of chiral tartaric acid ester” based upon variations in the mixing ratios of reactants and the desired starting alcohol, see Wang ‘566, Paras. [0010];[0020];[0022];[0031];[0034].
The 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. One of ordinary skill in the art would have been capable of modifying the mixing ratios of reactants and the desired starting alcohol of Wang ‘567 to produce the desired tartrate by applying the known technique of varying the mixing ratios of reactants and the desired starting alcohol as taught by Wang ‘566 with a reasonable predictability of success for the purpose of synthesizing the desired “type of chiral tartaric acid ester” based upon variations in the mixing ratios of reactants and the desired starting alcohol, see Wang ‘566, Paras. [0010];[0020];[0022];[0031];[0034]; 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 Wang ‘567 and Wang ‘566 both teach synthesizing the desired “type of chiral tartaric acid ester” based upon variations in the mixing ratios of reactants and the desired starting alcohol, a person of ordinary skill in the art has good reason to modify Wang ‘567 by relying upon Wang ‘566 before the effective filing date of the claimed invention for knowledge generally available within the methods for the catalytic synthesis of a chiral compound art regarding the desired “type of chiral tartaric acid ester” to synthesize, see MPEP 2143 B & G and 2141, for the benefit of synthesizing the desired “type of chiral tartaric acid ester” based upon variations in the mixing ratios of reactants and the desired starting alcohol, see Wang ‘566, Paras. [0010];[0020];[0022];[0031];[0034]; and MPEP 2143 I. B-D; 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.
Selection of a known material, such as the starting alcohol n-butanol to synthesize dibutyl tartrate, 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 specific molar mass of the reactants, “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.
Wang ‘567 does not teach the limitations of instant application claim 13.
Regarding the limitations of instant application claim 13, Wang ‘566 teaches to synthesis “the chiral source compound n-butyl tartrate using boric acid” “[t]he synthesis steps are as follows: First, chiral tartaric acid and the desired alcohol, such as n-butanol, are mixed. The mixing ratio varies depending on the type of chiral tartaric acid ester being synthesized. Then, toluene is used as the solvent and boric acid as the catalyst.”, see Paras. [0010]-[0014], meeting the butanol, the toluene, and n-butyl tartrate aka dibutyl tartrate in instant application claim 13.
Meng teaches the distillation is by the vacuum fractionation steps of:
“S1: First, exhaust the air from the distillation tower to make the vacuum degree in the distillation tower ≤-0.09MPa”;
“S2: drying the preliminarily refined terpineol acetate product and transporting it to the reactor of a distillation tower”;
“S3: heating to maintain the bottom temperature at 100-120 ◦C and the top temperature at 70-90°C, reflux for 1 hour, and collect the front fractions of ramie and terpinene” at a reflux ratio of 10-15:1, which will also collect the water-carrying agent and unreacted alcohol; and,
“S4: heating the tower to maintain the bottom temperature at 120-130 ◦C and the top temperature at 90-105 ◦C, with a reflux ratio of 20:1, and collecting the intermediate fractions of borneol, fenchol, terpineol, and fenchyl acetate”, see Paras. [0027];[0046]-[0051], meeting and within the ranges of steps S1-S4 in instant application claim 13.
Regarding instant application claim 13, 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 Wang ‘567 to use the vacuum filtration fractionation as taught by Meng with a reasonable predictability of success for the purpose of efficiently esterifying an alpha-hydroxycarboxylic acid to produce an alpha-hydroxycarboxylic acid ester of excellent color using an integrated simple industrial production process that has a low emission of wastes, a short production period, low cost, and is environmental friendly, see Guo, Abstract, Paras. [0005];[0028], Meng, Abstract, Paras. [0005];[0009].
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 Wang ‘567 and Meng both teach the purification of an alpha-hydroxycarboxylic acid ester, a person of ordinary skill in the art has good reason to purify an alpha-hydroxycarboxylic acid ester, by pursuing the known options within their technical grasp for the benefit of efficiently esterifying an alpha-hydroxycarboxylic acid to produce an alpha-hydroxycarboxylic acid ester of excellent color using an integrated simple industrial production process that has a low emission of wastes, a short production period, low cost, and is environmental friendly, see Guo, Abstract, Paras. [0005];[0028], Meng, Abstract, Paras. [0005];[0009], MPEP 2141, and MPEP 2143 B & G.
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 regard to the selection of reaction temperatures, reaction times, vacuum distillations, and pressures, “[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”, In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929), see MPEP 2144.05.
Conclusion
No claims are allowed.
Applicant's amendment necessitated the new 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 nonprovisional extension fee (37 CFR 1.17(a)) 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.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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