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 .
DETAILED ACTION
This Final Office action is based on the 1/889590 application originally filed September 19, 2024.
Amended claims 1-15, filed March 26, 2026, are pending and have been fully considered. Claims 6 and 8-13 are withdrawn from consideration due to being drawn to a nonelected invention.
Claim Rejections - 35 USC § 103
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 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.
Claim(s) 1-5, 7, 14 and 15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Chang et al. (WO 2013/183872 A1) hereinafter English Translation “Chang” in view of Otera “Transesterification” Chemical Reviews Vol. 93 No. 4. 1993. ppgs 1449-1470.
Regarding Claims 1-5, 7, 14 and 15
Chang discloses in the abstract, a method for manufacturing a biodegradable ester lubricating base oil by using a solid acid catalyst, and more specifically, to a method for manufacturing a biodegradable ester lubricating base oil having the advantage of increasing product yield by using a highly-reactive solid acid catalyst in a transesterification reaction of triglyceride and polyvalent alcohol, or by using the solid acid catalyst in a transesterification reaction of a fatty acid and polyvalent alcohol, at the same time as the transesterification reaction of the triglyceride and the polyvalent alcohol.
Chang discloses on page 4, (a) Process 1 for transesterifying triglyceride with alcohol and
Process 2 (b) esterifying a fatty acid derived from triglycerides with an alcohol 2.
Chang discloses on page 3, a biodegradable ester lubricant base oil according to the present invention includes the step of transesterifying a triglyceride with an alcohol in the presence of a catalyst having a surface area of 36.5-103.7 m 2 / g and an acid point of 237-842 μmol / g.
Chang further discloses on page 3, the triglyceride used in the reaction of the present invention is not limited as long as it is biodegradable vegetable or animal fats and oils, soybean oil, rapeseed oil, corn oil, rapeseed oil, sunflower oil, castor oil, palm oil, linseed oil, poppy. It may be at least one selected from oil, walnut oil, peanut oil, cottonseed oil, rice bran oil, camellia oil, olive oil, tallow, pork, sunny, fish oil and diesel.
Chang discloses on pages 3 and 4, the alcohol used in the reaction of the present invention may be monoalcohol or polyhydric alcohol, and in the case of monoalcohol, in order to exert the effect as a lubricating base oil, it is preferable that it is 8 to 20 carbon atoms (includes 2-ethylhexanol). The polyhydric alcohol is preferably in the case of glycerol, neopentyl glycol, diethyl propanediol, trimethylol propane, pentaerythritol, dipentaerythritol, or sorbitol.
Chang discloses on page 4, the production method obtains an ester lubricating base oil by step 1 of obtaining an ester lubricating base oil by a transesterification reaction of triglyceride and an alcohol, or an esterification reaction of a fatty acid derived from triglyceride or a fatty acid derived from mineral oil and an alcohol. Step 2 occurs simultaneously to produce a biodegradable ester lubricant base oil.
Here, the fatty acids used for the simultaneous progression are octanoic acid, 2-ethylnucleic acid, isooctanoic acid, isononanoic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid and oleic acid. It may be at least one selected from elic acid, linoleic acid, linolenic acid, arachidic acid, eicosane acid, behenic acid, erucic acid, lignoseric acid, nerbonic acid, serotosan.
Chang discloses on page 3, under transesterification and esterification, the catalyst is a solid acid catalyst, characterized in that obtained by treating sulfuric acid to the zirconia precursor.
Chang discloses known catalyst used for transesterification and esterification but fails to teach the claimed catalyst of an alkali metal octoxide for transesterification and a sulfonic acid for esterification.
However, Otera discloses on page 1450, in this article, the classical acid- or base-catalyzed transesterification is touched rather briefly so as simply to provide readers with the basic idea. Otera discloses on page 1450, transesterification/esterification has been carried out traditionally and most frequently by the use of acid catalysts such as sulfuric, sulfonic, phosphoric, and hydrochloric acids. Otera discloses on page 1451, base-catalyzed reaction is another conventional, popular transesterification. A wide variety of metal alkoxides are employable but the most popular are sodium and potassium alkoxides. Besides the alkoxides, metal acetate, oxides, and carbonates also work on occasion.
It is to be noted, the potassium alkoxides would include or are the same as the claimed alkali metal n-octoxide.
A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) (discussed in more detail below) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) (discussed below and in MPEP § 2144) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. See also MPEP § 2144.08, paragraph II.A.4.(c). The prior art element performs the identical function specified in the claim in substantially the same way, and produces substantially the same results as the corresponding element disclosed in the specification. Kemco Sales, Inc. v. Control Papers Co., 208 F.3d 1352, 54 USPQ2d 1308 (Fed. Cir. 2000).
It would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to use an acid or base catalyst for transesterification or esterification of Otera as the transesterification and esterification catalyst of Chang. The motivation to do so is to use an acid or base catalyst for transesterification or esterification for aiding in the production of esters.
Response to Arguments
Applicant's arguments filed March 26, 2026 have been fully considered but they are not persuasive.
Applicants argued: “The Applicant disagrees with the asserted basis of obviousness and urges that the rejection would not be maintained if proper attention is given to the facts that (i) neither reference specifically discloses or specifically suggests the use of the claimed catalysts with the octanols, and (ii) neither reference suggests that the use of the claimed catalysts with an octanol would provide a process which yields octyl esters which contain less than 10 ppm methanol and/or less than 10 ppm ethanol, i.e., "methanol-free" and "ethanol- free" (see the Specification at paragraph [0018]) as recited in claim 1 and in claim 7. Not only does the applied art fail to recognize the surprising "methanol-free" and "ethanol-free" result from using the recited catalysts, Otera specifically mentions the problem that transesterification is hampered by the generation of alcohols during transesterification using other catalysts, and teaches that continuous removal of the alcohol is indispensable for a good yield of the desired esters. Nothing in Chang teaches a process which would yield "methanol-free" and "ethanol-free" biofuel.”.
Applicants arguments are not deemed persuasive. First, as stated in the above rejection, Chang modified by Otera discloses the claimed acid or base catalysts that are known in the art to be used for transesterification or esterification. In response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). Second, in response to applicant's argument that the references fail to show certain features of the invention, it is noted that the features upon which applicant relies (i.e., a process which yields octyl esters which contain less than 10 ppm methanol and/or less than 10 ppm ethanol) are not recited in the rejected claim(s). 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). It is maintained Chang discloses transesterification that forms esters of fatty acids. It is to be noted, Chang does not disclose the formed esters having methanol and/or ethanol and therefore Chang has met the limitation of the present invention of having esters that are methanol and/or ethanol free. Therefore, Chang modified by Otera has met the limitations of the presently claimed invention.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Lichtenberger et al. (US 2007/0219340) discloses in paragraph 0003, an apparatus for esterification and transesterification reactions and associated methods of use is disclosed. More particularly, methods, systems and apparatus are disclosed which increase the efficiency of esterification and transesterification reactions.
Ruwwe et al. (US 2012/0066965) discloses in the abstract, a method to transesterify triglycerides in the presence of a catalyst system comprising a transesterification catalyst selected from the group of the alkali metal and alkaline earth metal alkoxides and the alkali metal hydroxides, and at least one activator other than the transesterification catalyst, selected from the group comprising salt compounds, titanates and non-salt compounds having a density of at least 0.9 g/ml, is provided. Additionally provided is a method to prepare biodiesel by transesterification of a natural fat.
THIS ACTION IS MADE FINAL. 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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LATOSHA D HINES whose telephone number is (571)270-5551. The examiner can normally be reached Monday thru Friday 9:00 AM - 6:00 PM.
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/Latosha Hines/Primary Examiner, Art Unit 1771
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