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 Office action is based on the 18/698933 application originally filed April 05, 2024.
Amended claims 1-3, 5 and 6, filed April 05, 2024, are pending and have been fully considered.
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 1-6 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 is unclear to the term “a base” making the claim indefinite. It is unclear as to what defines “a base”. Applicants should amend and/or clarify claim 1.
Claim 5 is unclear as to if the claim is directed to a method or product due to the claim states a product but also list a method step in the preamble. Further amending and/or clarification of claim 5 is required.
Claim 5 contain the trademark/trade name(s):
Entech7200 automated concentrator manufactured by Entech Instruments Inc.
Sumitomo Seika Chemicals Company, Limited.
Agilent 7890B gas chromatography system manufactured by Agilent Technologies, Inc.
ODP3 (sniffing system) manufactured by Gestel, Inc.
MSD5977B (mass spectrometer) Agilent 5977B MSD manufactured by Agilent Technologies, Inc.
Where a trademark or trade name is used in a claim as a limitation to identify or describe a particular material or product, the claim does not comply with the requirements of 35 U.S.C. 112, second paragraph. See Ex parte Simpson, 218 USPQ 1020 (Bd. App. 1982), and MPEP 2173.05(u). The claim scope is uncertain since the trademark or trade name cannot be used properly to identify any particular material or product. A trademark or trade name is used to identify a source of goods, and not the goods themselves. Thus, a trademark or trade name does not identify or describe the goods associated with the trademark or trade name.
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)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claim(s) 1-3 is/are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Shimizu et al. (WO 2021/132340 A1) hereinafter cited under US 20220354760 “Shimizu”.
Regarding Claims 1-3
Shimizu discloses in paragraph 0010, removing by-products from crude 1,3-butylene glycol to obtain high-purity 1,3-butylene glycol has been required.
Shimizu discloses in paragraph 0012, a method capable of manufacturing high-purity 1,3-butylene glycol having a high potassium permanganate test value, a very low content of low boiling point components, and a high initial boiling point with a high recovery rate. Shimizu discloses in paragraph 0225, a method for manufacturing 1,3-butylene glycol, which is a method for obtaining purified 1,3-butylene glycol from a crude reaction liquid containing 1,3-butylene glycol, the method including: (paragraph 0226) a dehydration step of removing water by distillation; a high boiling substance removal step of removing a high boiling point component by distillation; and a product distillation step of obtaining purified 1,3-butylene glycol, (paragraph 0227) wherein in the dehydration step, a dehydration column is used in which a liquid feed containing 1,3-butylene glycol and water with an acetaldehyde content of 1000 ppm or lower, and a crotonaldehyde content of 400 ppm or lower; is distilled under a condition of a reflux ratio of higher than 0.3 and a liquid concentrated with a low boiling point component containing water is distilled off from above a feed plate.
Shimizu discloses in paragraph 0073, the raw material for hydrogenation may or may not contain water but preferably contains water from the viewpoint of the purity of 1,3-butylene glycol product. The water content in the raw material for hydrogenation is not particularly limited but is, for example, preferably 2 wt. % or higher. The upper limit may be, for example, 90 wt. %, 80 wt. %, 70 wt. %, 60 wt. %, 50 wt. %, 40 wt. %, 30 wt. % or 20 wt. %. With the water content within the above ranges, the acetal of 1,3-butylene glycol and acetaldol contained in the resulting crude 1,3-butylene glycol is decreased, and thus this tends to increase the purity of the 1,3-butylene glycol product finally obtained. This is because the raw material for hydrogenation contains water to a certain extent, and the acetal is hydrolyzed into 1,3-butylene glycol accordingly as well as coexisting acetaldol is reduced into 1,3-butylene glycol.
Shimizu discloses in paragraph 0074, examples of the hydrogenation catalyst include Raney nickel. The hydrogenation catalyst can be used in a suspended state, or can also be added into a reaction vessel and used. The amount of the hydrogenation catalyst to be used is not particularly limited but is, for example, preferably from 1 to 30 parts by weight, relative to 100 parts by weight of the raw material for hydrogenation. The amount of hydrogen to be used in the reduction reaction is not particularly limited but is, for example, preferably from 0.5 to 40 parts by weight, weight relative to 100 parts by weight of the raw material for hydrogenation. A pressure (total pressure; gauge pressure) in a reaction system in the reduction reaction is not particularly limited, but is, for example, preferably from 9 to 70 MPa. A hydrogen pressure (partial pressure of hydrogen) in the reaction system is not particularly limited, but is, for example, from 7 to 60 MPa. The reaction temperature in the reduction reaction is not particularly limited but is, for example, preferably from 40 to 150° C. The reaction time (residence time) in the reduction reaction is not particularly limited but is, for example, from 10 to 500 minutes. The present reaction can be carried out in any of a batch, semi-batch, or continuous manner.
Shimizu discloses in paragraph 0075, thus-obtained crude 1,3-butylene glycol contains acetaldehyde (AD); butylaldehyde; crotonaldehyde (CR); acetone; a low boiling point substance (low boiling point compound) having an unsaturated bond, such as methyl vinyl ketone; a condensate of these; a condensate of 1,3-butylene glycol and the above low boiling point substance (e.g., an acetal of 1,3-butylene glycol and acetaldol); an alcohol such as ethanol, isopropyl alcohol, or butanol; water (for example, solvent), a salt produced by neutralization or the like, a catalyst (when used in suspension) or the like. By removing these impurities in the purification step, a 1,3-butylene glycol product (purified 1,3-butylene glycol) can be obtained.
Shimizu discloses in paragraph 0112, in the product column F for use in the product distillation, a 1,3-butylene glycol liquid feed with an acetaldehyde content of 500 ppm or lower and a crotonaldehyde content of 200 ppm or lower is distilled under a condition of a reflux ratio of higher than 0.1, a liquid concentrated with a low boiling point component is distilled off from above a feed plate (corresponding to “X-6” in FIG. 1), and a 1,3-butylene glycol product is extracted from below the feed plate (corresponding to “Y” in FIG. 1).
Shimizu discloses in paragraph 0113, the product column F can be, for example, a perforated-plate column, a bubble column, or the like, but is more preferably a packed column with a low pressure loss, filled with Sulzer Packing, Melapack (trade names owned by Sumitomo Heavy Industries, Ltd.). This is because 1,3-butylene glycol and trace impurities would be thermally decomposed at a high temperature (e.g., 150° C. or higher) and produce a low boiling point substance, which is a coloring component, and thus the distillation temperature is to be lowered. In addition, this is also because a long thermal history (residence time) for 1,3-butylene glycol would also have a similar effect. Thus, the reboiler employed is preferably one with a short residence time of the process side fluid, for example, a thin-film evaporator, such as a natural downward flow thin-film evaporator or a forced-stirring thin-film evaporator.
Shimizu discloses in paragraph 0115, in charging the product column F, the column top vapor from the dealkalization column E is condensed in the condenser E-1, and the resulting condensed liquid is fed, but the column top vapor from the dealkalization column E may be directly fed to the product column F.
The claimed invention is anticipated by the reference because the reference teaches a composition which comprises all of the claimed components. In the alternative, no patentable distinction is seen to exist between the reference and the claimed invention absent evidence to the contrary.
In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Allowable Subject Matter
Claims 5 and 6 would be allowable if rewritten or amended to overcome the rejection(s) under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), 2nd paragraph, set forth in this Office action.
The applied prior art fails to teach and/or suggest the high-purity 1,3-butylene glycol, wherein in GC/MS-olfactometry under the following conditions, a toluene-d8-equivalent concentration of methyl vinyl ketone is 0.25 vol ppb or less.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Tsuji et al. (JP 2001-213823 A) discloses in the abstract, to produce 1,3-butylene glycol by hydrogenating acetoaldols, by using by-product crotonaldehyde, to obtain by-product butanol with less impurities, and then to obtain high-quality butanol.
Shimada et al. (WO 2019/240009 A1) discloses in the abstract, provided is a method for producing 1,3-butylene glycol, the method including a step for hydrogenating 4-hydroxy-2-butanone, and involving the use of a metal catalyst supported on a support in the aforementioned step. In the aforementioned step, the metal catalyst preferably includes at least one selected from the group consisting of platinum, palladium, cobalt, ruthenium, and rhodium, and the support preferably includes alumina.
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/Latosha Hines/Primary Examiner, Art Unit 1771
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