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
The preliminary amendment filed on 08/01/2023 has been entered. Claims 1-6 are currently pending and are under examination.
Claim Objections
Claims 1-6 are objected to because of the following informalities: the claims are replete with idiomatic errors, for example:
Claim 1, “causing … to react”, “causing a reaction of the unreacted 2-methoxyethanol”, “obtained in the causing (A2)”;
Claim 2, “causing … to react”, “causing a reaction”, “obtained in the causing (A2-2)”;
Claim 3, “wherein the performing (A2-2);
Claim 4, “causing (A1)”
Claim 5, “the removing (A3)”;
Claim 6, “causing a reaction of unreacted 2-methoxyethanol”, “obtained in the causing (B1)”
Applicant is advised is advised to replace the claims by:
Claim 1. A method for producing (2-methoxyethyl) vinyl ether using 2-methoxyethanol as a raw material alcohol, the method comprising:
(A1) reacting 2-methoxyethanol with acetylene to obtain a mixture comprising unreacted 2-methoxyethanol and (2-methoxyethyl) vinyl ether;
(A2) reacting the unreacted 2-methoxyethanol and the (2-methoxyethyl) vinyl ether in the mixture in the presence of an acid catalyst to obtain acetaldehyde bis(2-methoxyethyl)acetal; and
(A3) removing the acetaldehyde bis(2-methoxyethyl)acetal by distillation from an acetal-containing mixture obtained in (A2).
Claim 2. A method for producing (2-methoxyethyl) vinyl ether using 2-methoxyethanol as a raw material alcohol, the method:
(A1) reacting 2-methoxyethanol with acetylene to obtain a mixture comprising unreacted 2-methoxyethanol and (2-methoxyethyl) vinyl ether;
(A2) reacting a reaction of the unreacted 2-methoxyethanol and the (2-methoxyethyl) vinyl ether in the mixture in the presence of an acid catalyst to obtain acetaldehyde bis(2-methoxyethyl)acetal;
(A2-2) performing a treatment selected from the group consisting of neutralization of the acid catalyst and removal of the acid catalyst; and
(A3) removing the acetaldehyde bis(2-methoxyethyl)acetal by distillation from an acetal-containing mixture obtained in (A2-2).
Claim 3. The method of claim 2, wherein (A2-2) comprises the neutralization of the acid catalyst using a basic compound.
Claim 4. The method of claim 1, wherein (A1) is performed in the presence of an alkali metal alcoholate catalyst.
Claim 5. The method of claim 1, wherein a distillation pressure in (A3) is 40 kPaA to atmospheric pressure.
Claim 6. A method for purifying (2-methoxyethyl) vinyl ether from a mixture containing 2-methoxyethanol and (2-methoxyethyl) vinyl ether, the method comprising:
(B1) reacting a reaction of 2-methoxyethanol and (2-methoxyethyl) vinyl ether in the mixture in the presence of an acid catalyst to obtain acetaldehyde bis(2-methoxyethyl)acetal; and
(B2) removing the acetaldehyde bis(2-methoxyethyl)acetal by distillation from an acetal-containing mixture obtained in (B1).
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 1-6 are rejected under 35 U.S.C. 103 as being unpatentable over Oparina (Oparina, L. A. et al. “Vinylation of Hydroxy-Containing Cyclic Formaldehyde Acetals with Acetylene” Russian Journal of Organic Chemistry, 2008, Vol. 44, No. 10, pp. 1434–1437) in view of Patent application publication number US2010/0249465A1 (US’465) as evidenced by Alfa (“Vinyl 2-methoxyethylether”, pages 1-4) and A2B (“6-Methyl-2,5,7,10-tetraoxaundecane”, pages 1-5).
Regarding claims 1-2 and 6, Oparina teaches a method of reacting 2-methoxyethanol with acetylene in the presence of potassium hydroxide followed by distillation to obtain a mixture comprising (2-methoxyethyl)vinyl ether and 22% of unreacted methoxyethanol (pg. 1437, 1st col.).
Oparina fails to teach steps (A2)-(A3) (claims 1-3 and 5) and steps (B1)-(B2) (claim 6), in which (2-methoxyethyl)vinyl ether and methoxyethanol in the mixture are reacted to obtain acetaldehyde bis(2-methoxyethyl)acetal followed by removing acetaldehyde bis(2-methoxyethyl)acetal by distillation. The reference also fails to teach or suggest the use of alkali metal alcoholate as a catalyst in step (A1) (claim 4). The deficiencies are however cured by US’465.
Regarding claims 1-3 and 6, in the same field of endeavor as Oparina, US’465 teaches a process for producing vinyl ether by reacting a raw material alcohol with acetylene. The reference has recognized that the crude vinyl ether forms an azeotropic mixture with unreacted raw material alcohol, making the separation vinyl ether from the unreacted alcohol via distillation difficult ([0005]). Thus, the method of US’465 ([0014]-[0029]) is drawn to a method for producing a high-purity vinyl ether efficiently from the crude vinyl ether containing the unreacted raw material alcohol even when the vinyl ether and the alcohol form an azeotropic mixture and which includes a purification step of easy handling, wherein the method comprises:
a first step (similar to (A1)); a vinyl ether synthesis step of subjecting an alcohol (I) represented by the general formula (1)
R—O—H (1)
(wherein R is an aliphatic hydrocarbon group or an alicyclic hydrocarbon group), to a vinyl ether formation reaction in the presence of a catalyst to synthesize a vinyl ether (II) represented by the general formula (2)
R—O—CH═CH2 (2)
(wherein R is an aliphatic hydrocarbon group or an alicyclic hydrocarbon group)
a second step (similar to (A2)); a catalyst removal step of removing the catalyst from the reaction mixture obtained in the first step to obtain a crude vinyl ether containing the vinyl ether (II) and the unreacted raw material alcohol (I)
a third step (similar to (A3) and (A2-2)); an acetal formation step of reacting the unreacted raw material alcohol (I) in the crude vinyl ether, with the vinyl ether (II) in the presence of an acid catalyst, to convert the alcohol (I) and vinyl ether (II) into an acetal (III) represented by the general formula (3)
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(wherein R is an aliphatic hydrocarbon group or an alicyclic hydrocarbon group), followed by neutralizing the acid catalyst by the addition of a basic compound ([0074]-[0075], as in (A2-2))
a fourth step (similar to (A3)); a distillation and purification step of subjecting a crude vinyl ether containing the acetal (III) to distillation to obtain a high-purity vinyl ether.
Regarding claim 4, US’465 further teaches that the first step (as in (A1)) is conducted in the presence of alkali metal alcoholate ([0057]-[0058]).
It is noted that the distillation in Oparina does not effectively separate the (2-methoxyethyl) vinyl ether from the unreacted 2-methoxyethanol as 22% of the latter is still present in the mixture after distillation.
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It appears, the same distillation problem is encountered in Oparina as discussed in US’465. Thus, one of ordinary skill in the art would have been motivated to use the teachings of US’465 in the process of Oparina by reacting (2-methoxyethyl) vinyl ether with the unreacted 2-methoxyethanol to acetaldehyde bis(2-methoxyethyl)acetal followed by distilling acetaldehyde bis(2-methoxyethyl)acetal with a reasonable expectation of success in obtaining (2-methoxyethyl) vinyl ether at a high purity.
Regarding claim 5, US’465 teaches that the distillation pressure of the acetal is 0.1 to 13.3 kPa ([0080]) but not 40 kPa to atmospheric pressure as instantly claimed. However, determining a distillation pressure would be within the purview of a skilled artisan through routine experimentation. In fact, as evidenced by Alfa and A2B, (2-methoxyethyl) vinyl ether and acetaldehyde bis(2-methoxyethyl)acetal have a large boiling point at atmospheric pressure of 101.4 °C and 197.2 °C, respectively. Thus, based on the boiling point difference, the skilled artisan would have been motivated to use atmospheric pressure to separate (2-methoxyethyl) vinyl ether from acetaldehyde bis(2-methoxyethyl)acetal. Furthermore, conducting a distillation process under vacuum, which also includes the claimed 40 kPa to less than atmospheric pressure, is also a known process to the skilled artisan in order to lower the boiling points of the materials to be separated and prevent thermal degradation. Thus, the skilled artisan would also determine the optimal workable distillation pressure through routine optimization and would arrive at the claimed distillation pressure range.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a method for producing/purifying (2-methoxyethyl) vinyl ether as instantly claimed in view of the combination of Oparina and US’465.
Conclusion
Claims 1-6 are rejected and no claims are allowed.
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/MEDHANIT W BAHTA/Primary Examiner, Art Unit 1692