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 responsive to Applicant’s response to restriction requirement, filed July 30, 2026. As filed, claims 1-6, 8, 9, 15-23 are pending in the instant application. Claims 7, 10-14 are cancelled.
Priority
This application filed 12/18/2023 is a National Stage entry of PCT/AU2022/050616 , International Filing Date: 06/17/2022 claims foreign priority to 2021901842, filed 06/18/2021.
Information Disclosure Statement
Applicants' information disclosure statements (IDS) have been considered except where lined through. Please refer to Applicants' copy of the 1449 submitted herewith.
Election/Restrictions
Applicants’ election without traverse of Group I, claims 1-6, 8, 9, 15-22, drawn to the process as recited in the claims in the reply filed on 07/31/2026 is acknowledged.
Claim 23 is withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Claims 1-6, 8, 9, 15-22 will be examined on the merits herein.
Claim Objections
1.Claims 1, 15, 18 and 19 are objected for reciting improper Markush language: the recitation in claim 1 “the base comprises” should be changed to “is selected from the group consisting of”. The recitation in claims 15 and 18, 19 “selected from” should be changed to “is selected from the group consisting of See MPEP 803.02. “A Markush-type claim recites alternatives in a format such as "selected from the group consisting of A, B and C."
2.Claims 1 and 16 recite the “used” language. The objected claim is not viewed as “use” claim, but proper transition wording should be present.
3. Claim 18 appears to contain a typographical error:” (1,2-diamnoethane)”
Appropriate correction is required.
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 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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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.
Claims 1-6, 8, 9, 15 are rejected under 35 U.S.C. 103 as being unpatentable over Ismagilov et al., Russian Journal of General Chemistry, 1993, 63, 1, pages 146-150 (cited by Applicants in IDS) in view of US2012/0114527A1 May, 2012, by Hoglund (the ‘527 publication; cited in PTO-892 attached herewith).
Regarding claims 1 and 15, the article by Ismagilov teaches synthesis of 1,1-
dichloro-2 ,2-difl uoro-3-oxabutane (IV) which corresponds to the claimed methoxyflurane of formula ClClHC-CF2OCH3 by reacting compound I of formula Cl2C=CF2 in a solution of a base – alkali metal base NaOCH3 in methanol (scheme on page 547):
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The experimental on page 150 of the cited reference teaches that prior to mixing in the reaction flask, the reactants, dichlorodifluoroethylene (I) and sodium methoxide (II), had been dissolved in a binary CH3OH-CC14 (1:1 by volume) system and thermostated; the reactions were performed at temperatures of -10 to +5°C, at concentrations of the starting compounds varied from 0.06 to 0.25 M; the rate constant of the formation of the product -the results on Table 1 and Table 2 on page 147 (instant claim 1).
The method of the present application differs from the method described in the article by Ismagilov in that prior art does not teach introducing in a plate reactor for the reaction components of claimed process, wherein the plate reactor comprises a fluidic module defining one or more fluidic path(s) through which the reaction components flow as a reaction mixture, and the methoxyflurane is formed at least upon the reaction components mixing, with the so formed methoxyflurane flowing out of the plate reactor in a reactor effluent.
With regards to conducting the reaction in a continuous mode and in a plate reactor comprises a fluidic module defining one or more fluidic path(s) through which the reaction components flow as a reaction mixture, these limitations are taught in the ’527 publication.
The ’527 publication teaches the use of plate reactor for the continuous reaction, wherein the plate reactor comprises a fluidic module defining one or more fluidic path(s) through which the reaction components flow as a reaction mixture (instant claim 1).
The ’527 publication teaches that the plate reactor is utilized to provide a continuous flow module, which has good accessibility and is easy to handle, with a good heat transfer performance, and opportunity to control temperature, and is suitable for chemical reactions, extractions, separations and has improved pressure properties. The reference further teaches the flow module using plate reactor can be used to perform different reaction types (abstract; [0004]-[0015]; Fig 1-25). Accordingly, a skilled artisan would have been motivated to use the continuous plate reactor of the ’527 publication in place of the batch reactor of Ismagilov with a reasonable expectation of success in controlling the process parameters.
Moreover, regarding the continuous reaction mode of instant claims, although the cited reference does not discuss a continuous reaction mode, it would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art, to operate the process for the formation of the same compound in a continuous mode and have reasonable expectation of success in producing claimed compound. See also MPEP 2144.04: “In re Dilnot, 319 F.2d 188, 138 USPQ 248 (CCPA 1963) (Claim directed to a method of producing a cementitious structure wherein a stable air foam is introduced into a slurry of cementitious material differed from the prior art only in requiring the addition of the foam to be continuous. The court held the claimed continuous operation would have been obvious in light of the batch process of the prior art.)”
Regarding instant claim 2, the plate reactor, the ’527 publication teaches the reactor comprises a stack of fluidic modules (see [0015]).
Regarding instant claim 4, the ’527 publication teaches that the dimensions of the flow channel of the reactor plate are: cross-section 3.0 mm×16 mm in average, length of the flow channel approximately 6 m (see [0080]), and thus the internal volume is 0.000288 m3 or 288 mL.
Regarding instant claim 5, the ’527 publication teaches the plate reactor provides a good heat transfer performance, and control of temperature that is suitable for chemical reactions, and thus a skilled artisan would have a reasonable expectation in enhancing the yield of the product of the process disclosed by Ismagilov, by controlling such parameters and thus in increasing the amount of the product in the reactor effluent to at least 90% by volume.
Regarding instant claims 6 and 9, the ’527 publication teaches that by the use of the channel plate high mixing rates can be created and a narrow distribution of the residence time is obtained ([0011]). Furthermore, the reference teaches a pump may be connected for supplying and to pressurize the fluid to the nozzle ([0023]) and further teaches in [0024]:
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Therefore, it would be within the purview of a skilled artisan to control and determine through routine experimentation an optimal workable range of the residence time and flow with a reasonable expectation in optimizing the reaction using the plate reactor.
Regarding claim 8, the ’527 publication further teaches that the fluids are mixed prior to passing the channels of the plate reactor:
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While on [0030] it teaches the three-dimensional channels::
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It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention, to combine the teachings of Ismagilov regarding synthesis of methoxyflurane by reacting compound I of formula Cl2C=CF2 in a solution of a base – alkali metal base NaOCH3 in methanol with the teachings of the ‘527 publication regarding utilizing the plate reactor which comprises a fluidic module defining one or more fluidic path(s) through which the reaction components flow as a reaction mixture for converting batch processes to continuous processes because the ’527 publication teaches the plate reactor provides a good heat transfer performance, and control of temperature that is suitable for chemical reactions. Therefore, a skilled artisan would have a reasonable expectation in enhancing the yield of the product of the process disclosed by Ismagilov.
The rationale to support a conclusion that the claim would have been obvious is that teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention. KSR, 550 U.S. at_, 82 USPQ2d at 1395.
Thus, the claimed invention as a whole is prima facie obvious over the combined teachings of the prior art.
Claim Objections
Claims 16-22 are objected to as being dependent upon a rejected base claim.
Conclusion
Claims 1-6, 8, 9, 15 are rejected. Claims 16-22 are objected to. Claim 23 is withdrawn from further consideration.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANA MURESAN whose telephone number is (571)-270-7587. The examiner can normally be reached on Monday through Friday, 8:30 am to 5:30 pm EST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ANA Z MURESAN/Primary Examiner, Art Unit 1692
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