DETAILED ACTION
STATUS OF THE APPLICATION
Receipt is acknowledged of Applicants’ Amendments and Remarks, filed 21 November 2023, in the matter of Application No. 18/037,550. 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 1-10 are pending.
No claims have been cancelled.
Thus, claims 1-10 represent all claims currently under consideration.
Priority
Acknowledgment is made of Applicant's claim for foreign priority based on parent application PCT/CN2021/075896, filed on 7 February 2021. It is noted, however, that Applicant has not filed a certified copy of the CN202011566880.0 application as required by 37 CFR 1.55.
Applicant claims foreign priority to Application No. CN202011566880.0, filed on 25 December 2020.
Domestic Priority data as claimed by Applicant:
This application is a 371 of PCT/CN2021/075896 (02/07/2021)
Foreign Applications:
CHINA 202011566880.0 (12/25/2020)
Information Disclosure Statement (IDS)
The information disclosure statement (IDS) submitted on 17 May is in compliance with the provisions of 37 CFR 1.97. Accordingly, the IDS is being considered by the Examiner.
Specification
The disclosure is objected to because of the following informalities:
Example 9 of the written description (Specification; pages 9-10) presents the synthesis of compound 3g, yet the disclosed 1H NMR data for compound 3g data reports 34 H and does not match the hydrogen content (i.e., 33 H) of the reported product.
Appropriate correction is required.
Claim Objections
Claim 2 is objected to because of the following informalities:
In lines 3-4 “…substituent phenyl…; should read “…substituted phenyl…”
In line 7, “…substituent phenyl…; should read “…substituted phenyl…”
Claim 6 is objected to because of the following informalities:
In line 1, the extra spaces in the phrase “compound according” should be deleted.
Claim 8 is objected to because of the following informalities:
In lines 1-2, “…the method for preparing carboxylic acid ester compounds…” should read “…the method for preparing the carboxylic acid ester compound“…
Claim 9 is objected to because of the following informalities:
In line 1, “An application of nitrous acid ester…” should read “An application of a nitrous acid ester…”
In lines 1-2, “…a reaction of carboxylic acid compound…” should read “…a reaction of a carboxylic acid compound…”
Claim 10 is objected to because of the following informalities:
In line 1, “…free of a metals…” should read “…free of metals…”
Appropriate correction is required.
Claim Interpretation
The phrase “A carboxylic acid ester compound prepared by the method…according to claim 1.” as recited in instant claim 8 is being interpreted as a product-by-process claim. Although the process steps are not interpreted as actively required, they are considered to the extent that they limit the structure of the composition. See MPEP § 2113.
Claim Rejections - 35 USC § 101
35 U.S.C. 101 reads as follows:
Whoever invents or discovers any new and useful process, machine, manufacture, or composition of matter, or any new and useful improvement thereof, may obtain a patent therefor, subject to the conditions and requirements of this title.
Claims 9-10 are rejected under 35 U.S.C. 101 because the claimed inventions are directed to non-statutory subject matter.
Instant claims 9 and 10 are directed to non-statutory subject matter because it is unclear whether the claims are intended to encompass a product or a process. Specifically, claims 9 and 10 recite “An application of nitrous acid ester in catalyzing…” and is being interpreted as “use” claims because the claims fail to recite any active, positive steps, as recited in instant claim 9 and its dependent claim 10.
MPEP 2173.05(q) states:
A “Use” claim should be rejected under alternative grounds based on U.S.C 101 AND
112. In view of the split of authority, the most appropriate course of action would be to reject
a "use" claim under alternative grounds based on 35 U.S.C. 101 and 112.
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.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1-10 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 1 recites the term “methylene” in lines 5 and 7as a possible substituent for R2 and R3, respectively. However, a methylene group (–CH2–) renders the definition for R2 and R3 incomplete definition because the other substituent on the methylene group is undefined. This ambiguity in the scope of the recited genus renders the instant claim indefinite. Further clarification is required. The Examiner notes that adequately addressing this ambiguity will ameliorate this claim rejection.
Regarding claims 2-8, these dependent claims do not resolve the indefiniteness of claim 1 detailed above.
Claims 9 recites “An application of nitrous acid ester in catalyzing a reaction of carboxylic acid compound and an alcohol to prepare a carboxylic acid ester compound; and the alcohol is ethanol, propanol, or trifluoroethanol.” This claim is indefinite because it merely recites a use without any active, positive steps delimiting how this use is actually practiced. MPEP § 2173.05(q) states that “Attempts to claim a process without setting forth any steps involved in the process generally raises an issue of indefiniteness under 35 U.S.C. 112(b) or pre-AIA 35 U.S.C. 112, second paragraph.” The Examiner notes that amending the claim language to include active, positive steps regarding how the claimed use is practiced will ameliorate this claim rejection.
Regarding claim 10, this dependent claim does not resolve the indefiniteness of claim 9 detailed above.
Claims 10 recites “The application according to claim 9, wherein the reaction is free of metals or a metal compound.” This claim is indefinite because it merely recites a use without any active, positive steps delimiting how this use is actually practiced. MPEP § 2173.05(q) states that “Attempts to claim a process without setting forth any steps involved in the process generally raises an issue of indefiniteness under 35 U.S.C. 112(b) or pre-AIA 35 U.S.C. 112, second paragraph.” The Examiner notes that amending the claim language to include active, positive steps regarding how the claimed use is practiced will ameliorate this claim rejection.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 8 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Forbes et al. (“Brønsted acidic ionic liquids: the dependence on water of the Fischer esterification of acetic acid and ethanol”; J. Mol. Catal. A Chem. 2004, 214, 129-132; hereinafter “Forbes”).
Regarding claim 8 depending from claim 1, this claim is being interpreted as a product-by-process claim. Although the process steps are not interpreted as actively required, they are considered to the extent that they limit the structure of the composition. See MPEP § 2113.
Further regarding claim 8, Forbes discloses the preparation of ethyl acetate from acetic acid and ethanol via Fischer esterification (Forbes; page 130, Scheme 1):
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Thus, Forbes teaches a carboxylic acid ester compound derived from a carboxylic acid and ethanol, and therefore anticipates the limitation of product-by-process claim 8.
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.
Claims 1-6 and 9-10 are rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (CN101914014A; IDS of 05-17-2023; English language machine translation; hereinafter “Liu”), in view of Li et al. (“tert-Butyl Nitrite (TBN) as a Versatile Reagent in Organic Synthesis”; Synthesis 2018, 50, 711-752; hereinafter “Li”).
Regarding claims 1 and 9 and claims 3 and 8 depending from claim 1, Liu teaches a method for synthesizing and purifying synthetic ester oils for cosmetics (Liu; Title; Abstract; English language machine translation). The method of Liu comprises an esterification reaction between alcohol and acid reactants in the presence of a catalyst and a co-catalyst (Liu; claim 1; English language machine translation). The acid reactant is preferably a carboxylic acid, and the alcohol reactant may be monohydric or polyhydric organic alcohols, including ethanol and propanol (Liu; paragraphs [0035]-[0036]; English language machine translation). Furthermore, Liu teaches those suitable co-catalysts for the esterification reaction includes nitrous acid (Li; claim 6; paragraphs [0021] and [0042]). Thus, Liu teaches a method for preparing carboxylic acid esters from carboxylic acids and alcohols such as ethanol and propanol in the presence of nitrous acid via an esterification reaction, in a manner consistent with the limitations of instant claim 1.
Liu fails to teach a method for preparing a carboxylic acid ester compound comprising a nitrous acid ester, as recited in instant claim 1, or an application of a nitrous acid ester in catalyzing the preparation of a carboxylic acid ester compound, as recited in instant claim 9.
However, Li teaches that tert-butyl nitrite (TBN) is an important metal-free reagent that is widely applied in various organic transformations (Li; Title; Abstract). Of particular note, Li teaches that TBN has various advantages, such as commercial availability, inexpensiveness, good solubility in organic solvents, and easy handling (Li; page 711, Col. 1, paragraph 1). Li further teaches that TBN is a versatile reagent that can participated in various reactions and can release nitrous acid under acidic or aqueous conditions (Li; page 711, Col. 1, paragraph 1).
Thus, the teachings of Li inform the skilled artisan that tert-butyl nitrite (TBN), a nitrous acid ester, can generate nitrous acid in situ and is therefore functionally equivalent to the nitrous acid esterification co-catalyst described in the method of Liu.
The prior art as taught by Liu and Li reside in the overlapping technical field of structurally related nitrous acid esters or nitrous acid as reagents in organic synthesis, respectively, and are therefore deemed analogous art as described in MPEP § 2141.01(a). In addition, the teachings of Li inform the skilled artisan that the nitrous acid ester (i.e., tert-butyl nitrite) taught by Li is functionally equivalent to the nitrous acid of Liu because Li teaches that tert-butyl nitrite can release nitrous acid in situ under acidic or aqueous conditions. As such, the skilled artisan would be sufficiently motivated to substitute the nitrous acid of Liu with the nitrous acid ester (i.e., tert-butyl nitrite) of Li to pursue a method that implements a nitrous acid precursor with several advantages, such as commercial availability, inexpensiveness, good solubility in organic solvents, and easy handling with a reasonable expectation of success. Such an endeavor would result in the simple substitution of one known element for another to obtain predictable results, as described in MPEP § 2143(I)(B).
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 substituted the nitrous acid of Liu with the nitrous acid ester (i.e., tert-butyl nitrite) of Li to arrive at the invention of instant claims 1, 3 and 8-9. The motivation to do so would permit the skilled artisan to pursue, with a reasonable expectation of success, a method that implements a nitrous acid precursor with several advantages, such as commercial availability, inexpensiveness, good solubility in organic solvents, and easy handling, as described above.
Regarding claim 2 depending from claim 1, Liu teaches the esterification of isononanoic acid (Liu; Example 1; paragraphs [0061]-[0062]; English language machine translation). Isononanoic acid resides within the genus of instant claim 2 when R1 and R3 are hydrogen and R2 is methylene, or when R1 is C9 alkyl and R2 and R3 are hydrogen, respectively.
Regarding claims 4-5 depending from claim 1, Liu teaches that based on the total weight of the reactant acid and alcohol, the amount of co-catalyst used is 50-200 wt%, preferably 50-100 wt% (Liu; paragraph [0042]; English language machine translation). In addition, Liu teaches that if the alcohol is a monohydric alcohol and the acid is a monocarboxylic acid, the molar ratio of the alcohol to the acid is particularly recommended to be between 1.2 and 1.5 (Liu; paragraph [0039]; English language machine translation). Thus, the skilled artisan could arrive at an embodiment wherein the alcohol is 1.5 mol of ethanol (69.1 grams) and the carboxylic acid is 1 mol of butyric acid (88.1 grams) to arrive at a total weight of the reactant and alcohol of 157.2 grams based on the teachings of Liu alone (Liu; paragraphs [0035]-[0036] and [0039]; English language machine translation). When considering Liu in view of Li, the skilled artisan could arrive at an embodiment wherein 103.1 grams of tert-butyl nitrite is used (65.6 wt% relative to the total weight of reactant acid and alcohol). This embodiment would result in a molar ratio of carboxylic acid to nitrous acid ester of 1:1, and this ratio resides within the range recited in instant claim 4 and is identical to the ratio recited in instant claim 5. 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.” Therefore, as with claim 1, it would have been prima facie obvious to arrive at claimed invention based on the method of Liu in view of Li.
Regarding claim 6 depending from claim 1, Liu teaches that the esterification process is carried out a temperature of about 80-260 ºC and the reaction time is usually about 3-48 hours (Liu; paragraph [0040]; English language machine translation). The reaction temperature and time ranges of Liu 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.”
Regarding claim 10 depending from claim 9, Li teaches that tert-butyl nitrite (TBN) is an important metal-free reagent that is widely applied in various organic transformations (Li; Title; Abstract).. Thus, the method of Liu in view of Li is free of metals or a metal compound.
Claims 7 is rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (CN101914014A; IDS of 05-17-2023; English language machine translation; hereinafter “Liu”), in view of Li et al. (“tert-Butyl Nitrite (TBN) as a Versatile Reagent in Organic Synthesis”; Synthesis 2018, 50, 711-752; hereinafter “Li”) as applied to claims 1-6 and 9-10 above, and further in view of Sakakura et al. (“Open-air and solven-free ester condensation catalyzed by sulfonic acids”; Tetrahedron Lett. 2008, 49, 5017-5020; hereinafter “Sakakura”).
Regarding claim 7, claim 1 is rendered obvious over Liu in view of Li as detailed above.
Liu and Li fail to explicitly teach wherein the reaction is carried out in air, as recited in instant claim 7.
However, Sakakura teaches open-air and solvent-free ester condensation reactions catalyzed by sulfonic acids (Sakakura; Title; Abstract). Sakakura further teaches that the esterification method is highly practical and atom-economical since it does not require any solvent as well as additional equipment or additional amounts of materials and energy for dehydration.
The prior art as taught by Liu and Sakakura reside in the closely overlapping technical field of acid catalyzed esterification methods, the teachings of Liu, Li, and Sakaura reside in the overlapping technical field of synthetic organic chemistry. Therefore, the prior art is deemed analogous art as described in MPEP § 2141.01(a). As such, the skilled artisan would be sufficiently motivated to incorporate the teachings of Sakakura to the method of Liu and Li to pursue a highly practical and economical esterification method with a reasonable expectation of success. Such an endeavor would result in combining prior art elements according to known methods to yield predictable results, as described in MPEP § 2143(I)(A).
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 Liu and Li to incorporate the teachings of Sakakura to arrive at an esterification method wherein the reaction is carried out in air. The motivation to do so would permit the skilled artisan to pursue, with a reasonable expectation of success, an esterification method that is highly practical and economical since it does not require any solvent as well as additional equipment or additional amounts of materials and energy for dehydration, as described above.
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.
Conclusion
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
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