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 .
Status of the Claims
Claims 1-20 filed on 06/21/2023 are currently pending.
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1-12 and 14-20 in the reply filed on 01/20/2026 is acknowledged.
Claim 13 is withdrawn by the examiner from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
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.
Claim 10 is 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.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 10 recites the broad recitation pH of 7 or below, and the claim also recites from 3 to 7 which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
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 1-4 and 10 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Patent number US6,137,016 (US’016).
Regarding claims 1-4, US’016 teaches a process for purifying a mixture comprising 1,4-butanediol and an acetal thereof, 2-(4'-hydroxybutoxy)-tetrahydrofuran, comprising the steps of: (a) hydrolysis of the mixture comprising 1,4-butanediol and the acetal using water, resulting in the formation of the relative aldehyde; and (b) reduction of the aldehydes present in the hydrolysis product from step (a) by the addition of a reducing agent, H2, resulting in 1,4-butanediol (col. 4, ln. 1-21 and Example 1).
Regarding claim 1, US’016 is silent that the hydrolysis step results in the formation of the relative diol in addition to the aldehyde as instantly claimed, however, since the reference teaches every limitation of the hydrolysis step, there is a prima facie case of anticipation for the relative diol to be formed in US’016. MPEP § 2112.01.
Regarding claim 10, since the hydrolysis step is conducted with water, a skilled artisan would understand that the reaction is conducted at a pH of 7.
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.
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 8-9 and 17-19 are rejected under 35 U.S.C. 103 as being unpatentable over Patent number US6,137,016 (US’016).
The teachings of US’016 have been set forth above.
Regarding claims 8-9 and 17-19, the reference further exemplifies that the hydrolysis is carried out in the presence of water at an amount of 4 wt% with respect to the total weight of the aqueous solution (Table 1), but fails to exemplify the claimed amount exceeding 20% by weight or 50% by weight with respect to the total weight of the aqueous solution.
However, US’016 teaches in nonexemplified embodiment the 1,4-butanediol feed containing from about 0.1% by weight up to about 0.4% by weight of the acetal 2-(4'-hydroxybutoxy)-tetrahydrofuran (claim 2) and that water is added at a molar ratio of water:2-(4'-hydroxybutoxy)-tetrahydrofuran of at least about 1:1 up to about 1000:1 or more (col. 5, ln. 11-14). If the feed comprises 0.4 wt% of the acetal, the amount of the remaining component, 1,4-butanediol, is 99.6 wt%. In 100 g of the feed, the amount of the acetal and 1,4-butanediol is 0.4 g and 99.6 g, respectively. The amount of the acetal is equivalent to 0.0025 moles (based on 160.21 g/mol). Based on the molar ratio of water:acetal of 1000:1 or more, water is present at 2.5 mol or more (or 45 g or more) per 0.025 mol of the acetal. Thus, the total amount of the aqueous solution is 145 g (99.6 g 1,4-butanediol + 0.4 g acetal + 45 g water), and the amount of water in the aqueous solution is about 31 wt% or more. In view of MPEP § 2144.05, a prima facie case of obviousness exists since the claimed weight percent of water overlaps with that of the reference.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the invention to conduct a process for purifying a mixture comprising at least one diol and at least one acetal thereof, said process comprising the steps of (a) hydrolysis of the mixture comprising at least one diol and at least one acetal thereof, resulting in the formation of the relative aldehydes and/or ketones and the relative diols; and (b) reduction of the aldehydes and/or ketones present in the hydrolysis product from step (a) by the addition of a reducing agent, resulting in a diol of the same species as is present in the starting mixture, in which hydrolysis step (a) is carried out in the presence of water in an amount exceeding 20% or 50% by weight with respect to the total weight of the aqueous solution obtained in view of the teachings of US’016.
Claims 5-7, 14-16 and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Patent number US6,137,016 (US’016) in view of WO2016026726A1 (WO’726).
The teachings of US’016 have been set forth above.
Regarding claims 5-6 and 14-16, the reference further teaches a previous distillation step for the separation from the butane-1,4-diol of other by-products, such as γ-butyrolactone, tetrahydrofuran, water, alkanol (e.g. methanol or ethanol), and n-butanol (col. 5, ln. 1-7). However, US’016 fails to teach a preliminary step of separating a fraction enriched in at least one acetal from the mixture comprising the diol and acetal. The deficiency is cured by WO’726.
Regarding claims 5, 7 and 14-16, WO’726 discusses that 1,4-butanediol, which can be produced, for example, based on diacetoxybutene, propene, 1,4-butynediol, carboxylic acid derivatives such as maleic anhydride or esters of maleic acid, succinic acid, and by fermentation, generally contains 2-(4'-hydroxybutoxy)-tetrahydrofuran, hereinafter referred to as "acetal". Acetal is an undesirable byproduct because, as a monoalcohol, it leads to chain termination in polymer applications. Thus, the reference teaches a method of purifying 1,4-BDO containing the acetal using the steps:
a) extraction of the BDO using an ether as an extraction solvent,
b) separation of the phases into a BDO-rich phase and an ether-rich phase, c) distillative separation of the ether from the BDO-rich phase,
d) distillative purification of the BDO obtained in step c),
e) partial or complete introduction of the ether-rich phase into a hydrogenation step ([0005]-[0008]).
WO’726 teaches that the acetal content in BDO before the extraction step is in the range of 1000 to 10000 ppm ([0012]) and after step d), the acetal content is less than 1000 ppm ([0026]). In other words, a fraction enriched in the acetal is removed to reach an acetal content of less than 1000 ppm.
Regarding claim 6, if the acetal content in BDO before the extraction step is 10000 ppm, and after step d), the acetal content is less than 1000 ppm, the enriched fraction has the acetal content of 9000 ppm (10000-1000ppm).
It is noted that the process in US’016, which comprises hydrolysis of acetal to aldehyde followed by reduction of the aldehyde to BDO, reduces the amount of acetal to as low as 270 ppm from 1910 ppm (Table 1, Run 5). Thus, a skilled artisan would thus have been motivated to further purify BDO of WO’726 that contains less than 1000 ppm after the distillation step using the purification method of US’016 with a reasonable expectation of success in further reducing the amount of the acetal in 1,4-butanediol.
Regarding claim 20, US’016 teaches in nonexemplified embodiment the 1,4-butanediol feed containing from about 0.1% by weight up to about 0.4% by weight of the acetal 2-(4'-hydroxybutoxy)-tetrahydrofuran (claim 2) and that water is added at a molar ratio of water:2-(4'-hydroxybutoxy)-tetrahydrofuran of at least about 1:1 up to about 1000:1 or more (col. 5, ln. 11-14). If the feed comprises 0.4 wt% of the acetal, the amount of the remaining component, 1,4-butanediol, is 99.6 wt%. In 100 g of the feed, the amount of the acetal and 1,4-butanediol is 0.4 g and 99.6 g, respectively. The amount of the acetal is equivalent to 0.0025 moles (based on 160.21 g/mol). Based on the molar ratio of water:acetal of 1000:1 or more, water is present at 2.5 mol or more (or 45 g or more) per 0.025 mol of the acetal. Thus, the total amount of the aqueous solution is 145 g (99.6 g 1,4-butanediol + 0.4 g acetal + 45 g water), and the amount of water in the aqueous solution is about 31 wt% or more. In view of MPEP § 2144.05, a prima facie case of obviousness exists since the claimed weight percent of water overlaps with that of the reference.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the invention to conduct a process for purifying a mixture comprising at least one diol and at least one acetal thereof, said process comprising the steps of (a) hydrolysis of the mixture comprising at least one diol and at least one acetal thereof, resulting in the formation of the relative aldehydes and/or ketones and the relative diols; and (b) reduction of the aldehydes and/or ketones present in the hydrolysis product from step (a) by the addition of a reducing agent, resulting in a diol of the same species as is present in the starting mixture, wherein the process further comprises a preliminary step of separating a fraction enriched in at least one acetal from said mixture comprising at least one diol and at least one acetal thereof in view of the teachings of US’016 and WO’726.
Claims 11-12 are rejected under 35 U.S.C. 103 as being unpatentable over Patent number US6,137,016 (US’016) in view of Chaikin (Chaikin, S. W. et al. “Reduction of Aldehydes, Ketones and Acid Chlorides by Sodium Borohydride” J. Am. Chem. Soc. 1949, 71, 122-125).
The teachings of US’016 have been set forth above.
Regarding claims 11-12, the reference further teaches that the reduction step of the aldehyde is conducted with hydrogen as the reducing agent in the presence of a catalyst (col. 4, ln. 36-53 and col. 6). However, US’016 fails to teach that the reducing agent is a complex hydride. The deficiency is cured by Chaikin.
Chaikin teaches reduction of aldehydes, ketones and acid chlorides to alcohols by sodium borohydride. The reference further teaches the reactions can occur rapidly at room temperature in most cases and that the corresponding alcohols are formed in comparable yields.
US’016 teaches the reduction of aldehyde with H2 as the reducing agent to 1,4-butanediol is conducted at an elevated temperature of from about 30° C to about 170° C (col. 5, ln. 15-17), whereas Chaikin’s reducing agent can convert aldehydes to alcohols at room temperature. A skilled artisan would thus have been motivated in conducting the hydrogenation process at room temperature using the reducing agent of Chaikin, sodium borohydride, in place of H2 of US’016 and would have a reasonable expectation of success in reducing the aldehyde to 1,4-butanediol.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the invention to conduct a process for purifying a mixture comprising at least one diol and at least one acetal thereof, said process comprising the steps of (a) hydrolysis of the mixture comprising at least one diol and at least one acetal thereof, resulting in the formation of the relative aldehydes and/or ketones and the relative diols; and (b) reduction of the aldehydes and/or ketones present in the hydrolysis product from step (a) by the addition of a reducing agent, resulting in a diol of the same species as is present in the starting mixture, wherein the reducing agent is a complex borohydride in view of the teachings of US’016 and Chaikin.
Conclusion
Claims 1-12 and 14-20 are rejected and no claims are allowed.
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/MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692