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, 3-5, 7-9, 11-16, 19-25, are pending in this application.
Claims 2, 6, 10, 17-18, are deleted.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
The following is a quotation of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), first paragraph:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1, 3-5, 7-9, 11-16, 19-25, are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Starting with γ-butyrolactone to make α-methylene-γ-butyrolactone is known in the art, e.g. Lee et al. See claims 3, 14. There is no support in the specification for enablement of α-methylene-butyrolactone starting from γ-alkyl-γ-butyrolactones, claims 4, 15. Deleting claims 4, 15, will obviate the rejection.
“[A] secondary alcohol of a tertiary alcohol”, claim 1, line 10, lacks support in the specification. See specification, pp. 4, lines 15-16, and/or claim 13. Replacing “of” with “or” will overcome the rejection.
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, 3-5, 7-9, 11-16, 19-25, 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.
All the claims are drawn to a two-stage process. Therefore, “optional-one-pot” must be deleted in line 1, claims 1, 13. Both claims clearly cite “a first stage”, and “a second stage”.
Lines 2, and 4, claims 4, 15, cite comprising and contains, respectively, which imply applicant is claiming other lactones and alkyls not cited in the claims. Hence, the claims are indefinite. Deleting “the group comprising” and replacing “contains” with “is” will overcome the rejection.
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.
Claims 1, 3-5, 7-9, 11-16, 19-25, are rejected under 35 U.S.C. 103 as being unpatentable over Lee et al., US2015/0073156; in view of Babler, US2009/0270658; Hull, US 2,428,846; Santos et al., Green Chem (2019), 21(23): 6441-50; Gaertner, US 3,170,915; Griffin et al., Tetrahed (1967), 23(5): 2301-13.
Lee et al., teaches a two-phase process comprising: first phase Claisen condensation reaction of a lactone with at least one alkyl formate ester in the presence of at least one metal alkoxide base as solvent to make an enolate. In the second phase, the enolate reacts with paraformaldehyde to form alpha-methylene lactone. Starting with γ-butyrolactone the product is α-methylene-γ-butyrolactone. See reactions 1 and 2. Both phases are preferably at 10-40oC, which is less than 50oC, instant claims 12, 25. The solvent includes alcohols: methanol, ethanol, n-butanol; ethers: THF, dioxolane; aromatic compounds: toluene, xylene; polar solvents; combination thereof. The base is preferably sodium ethoxide; the lactone is preferably 5-6-ring lactones. Recovery step is by filtration and yield is up to 90% (residual starting reagent is 10%), table 1. A POSA who wanted to avoid the prior art would have known and be motivated to optimize the reaction variables to obtain less than 5% of residual starting reagent in instant claims 5, 16. See the entire document, particularly [0013]-[0014], [0030]-[0031],[0034], [0040]-[0041].
The prior art does not teach secondary or tertiary alcohol are solvents, the expected outcome in claims 5, 16, and the inherent properties in claims 21-22. However, the claims are obvious over the prior art in view of the following: Lee et al., teaches primary alcohols and polar solvents.
Primary, secondary, and tertiary alcohols are polar solvents. The polarity of secondary alcohols is about 94-96% of a primary alcohol. https://pmc.ncbi.nlm.gov/articles/PMC9596611, visited 9/26/25. Therefore, a POSA who wanted to avoid Lee et al., would have known and be motivated to replace primary with secondary alcohol in the process, with reasonable expectation of success.
Babler teaches a similar process, an aldol condensation, wherein the solvent is selected from tertiary alcohols: t-butyl alcohol, 2-Me-2-butanol (t-amyl alcohol); ethers: THF; aromatic compounds: toluene; or combination thereof. Recovery is by neutralization, filtering, evaporation at reduced pressure [0038], adding drying agents to the reaction mixture or by molecular sieves. 40 torr in instant claims 9, 11, is a reduced pressure. Therefore, it is embraced and motivated by “reduced pressure” by Babler. See the entire document, particularly [0020], pp. 3, 6.
Distillation is evaporation plus condensation. Therefore, a POSA who wanted to avoid Babler would have known and be motivated to replace evaporation with distillation at the time the invention was made. There is reasonable expectation of success because the procedures are in the same field of endeavor.
Claisen condensation is the ester version of aldol condensation; the mechanisms of both reactions are very similar. LibreTexts Chem: https://chem.libretexts.org/Bookshelves/Organic_ChemistryOCLUE%3A_organic_chemistry-life, visited 9/25/25. Having known this, a POSA would have known and be motivated to replace 1o alcohol with 3o alcohol in the process by Lee et al, at the time the invention was made with reasonable expectation of success.
Hull teaches a similar process, an aldol condensation, wherein after the first stage, the residual alkoxide base catalyst is neutralized to form a weak base by adding glacial acetic acid, C5, lines 59-67. See also the entire document.
Santos et al., teaches Claisen condensation for making γ-alkyl-α-methylene-γ-butyrolactone, wherein the alkyl is linear or branched C1-C6-alkyl. The solvent is selected from primary alcohol, tertiary alcohol, toluene, 2-MTHF and combination thereof, pp. 6442. After the first stage, the reaction medium was neutralized, which enhance the yield and selectivity of the product, pp. 6442, C2, ¶1, lines 17-20. See also the entire document. Hence, a POSA would have known and be motivated to try neutralizing the reaction media to enhance the yield and selectivity of the product at the time the invention was made with reasonable expectation of success.
Gaertner teaches a similar process, wherein alkoxide base is neutralized with anhydrous sodium bicarbonate (pKa 10.3), C9, lines 16-18. 10.3 pKa is between 9.0 and 13.5 in claims 21-22. A POSA would have known and be motivated to try neutralizing the base with anhydrous sodium bicarbonate, claim 24, at the time the invention was made with reasonable expectation of success.
Griffin et al., teaches a similar process, wherein alkoxide base is neutralized with a trialkylammonium salt of a mineral acid, pp. 2309, ¶2. A POSA would have known and be motivated to try neutralizing the base with a trialkylammonium salt, Claim 23, at the time the invention was made with reasonable expectation of success.
Claims 13, 21-22, cite inherent property of the neutralization agents. Under the US patent practice, inherent property is not a limitation of a product or compound. See In re Best, 562 F.2d 1252; 195 USPQ 430 (CCPA, 1977), Titanium Metals Corp. v Banner, 778 F.2d 775 (Fed. Cir. 1985), Continental Can Co. v Monsanto Co., 948 F.2d 1264 (Fed. Cir. 1991), In re Cruciferous Sprout Litig., 301 F.3d 1343 (Fed. Cir. 2002), In re Crish, 393 F.3d 1253 (Fed. Cir. 2004).
Claims 5, 16, cite expected outcome of the reaction. Under the US patent practice expected result is not given patentable weight in a method claim, In re Milton 67 USPQ2d 1614 (Fed. Cir. 2003).
The process is no more than a selective combination of prior arts, done in a manner obvious to one of ordinary skill in the art. There is no indication in the prior arts that would lead a POSA to doubt the combination could not be made. In re Mostovych, 144 USPQ 38 (CCPA 1964).
“[R]eason, suggestion, or motivation to combine may be found explicitly or implicitly: 1) in the prior art references themselves; 2) in the knowledge of those of ordinary skill in the art that certain references, or disclosures in those references, are of special interest or importance in the field; or 3) from the nature of the problem to be solved.” Ruiz v. A.B. Chance Co., 234 F.3d 654, 665; 57 USPQ2d 1161 (Fed. Cir. 2000); see In re Dembiczak, 175 F.3d 994, 999; 50 USPQ2d 1614 (Fed. Cir. 1999). Also, KSR Int. Co. v. Teleflex Inc, 550 U.S. 82 USPQ2d 1385 (2007), instructs courts to take a more “expansive and flexible approach” in determining whether a patented invention was obvious at the time it was filed. 550 U.S. at 415. In particular, the Court emphasized the role of “common sense”. “Rigid preventative rules that deny fact finders recourse to common sense … are neither necessary under our case law nor consistent with it.” Id. at 421. See Wyers v. Master Lock Co, 95 USPQ2d 1525, (Fed. Cir. 2010).
The motivation to selectively combine the prior arts is because 1) Claisen and aldol condensation reactions have similar reaction mechanisms; 2) the steps are common techniques well-known in the art, e.g. the prior arts; 3) the problem applicant wanted to solve: applicant wanted to avoid the prior arts; 4) applicant wanted to improve the purity and yield of the product. There is reasonable expectation of success because the invention and the prior arts and in the same field of endeavor.
As held in KSR Int. Co. v. Teleflex Inc, 550 U.S. 82 USPQ2d 1385 (2007), “when 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.”
In the instant, it is not beyond the ordinary skill of a scientist to selectively combine conventional techniques by the prior arts. Such is deemed invention of reasoning not of creativity, KSR, supra.
The claims are not allowable over the combination of the prior arts and knowledge well-known in the art.
IDS
Publications listed on the IDS filed 5/9/24, are not submitted. The listing of references in the specification is not a proper information disclosure statement. 37 CFR 1.98(b) requires a list of all patents, publications, or other information submitted for consideration by the Office, and MPEP § 609.04(a) states, "the list may not be incorporated into the specification but must be submitted in a separate paper." See the MPEP 2000 and 37 CFR 1.97, 1.98. The references and English translations of all foreign documents must be submitted.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Taofiq A. Solola, whose telephone number is (571) 272-0709.
If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Andy Kosar, can be reached on (571) 272-0913. The fax phone number for this Group is (571) 273-8300.
Any inquiry of a general nature or relating to the status of this application or proceeding should be directed to the Group receptionist whose telephone number is (571) 272-1600.
/TAOFIQ A SOLOLA/ Primary Examiner, Art Unit 1625
September 26, 2025