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 07/09/2024 has been entered. Claims 1, 3-6, 8-12, 15-20 and 22-24 have been amended. Thus claims 1-6, 8-12, 15-20 and 22-24 are currently pending and are under examination.
Claim Objections
Claims 3, 11 and 17-23 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Claim 17 is objected to because of the following informalities: the conjunction word “and” is missing before step c). Appropriate correction is required.
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.
Claim 24 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by TCI (“2-Chloro-1,1,2-trifluoroethyl methyl ether” Deposit and available date 2010-03-02, pages 1-2).
TCI teaches 2-chloro-1,1,2-trifluoroethyl methyl ether at a purity of >99.0%.
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 1-2, 4-6, 8-12 and 15-16 are rejected under 35 U.S.C. 103 as being unpatentable over Patent number CS246644B1 (CS’644; cited in IDS in 05/23/2024 and machine translation attached herein) in view of Patent application publication number US2012/0114527A1 (US’527).
Regarding claims 1, 12 and 15, CS’644 teaches a process for the preparation of (2-chloro-1,1,2-trifluoroethyl) methyl ether (FClHC-CF2OCH3), the process comprising a step of reacting 1,2-dichloro-1,1,2-trifluoroethane (FClHC-CClF2), with alkali metal hydroxide (base) and methanol, wherein the base is used in solution.
Regarding claim 10, CS’644 teaches the base used is an amount within 1-30% by weight relative to the total weight of base and methanol. Example 3 uses 40 g of sodium hydroxide and 160 mL of methanol (equivalent to 125.85 g), and thus sodium hydroxide used is 24.1 wt.% relative to the total weight of base and methanol.
Regarding claim 16, the reaction is conducted at a temperature of 20 to 50 °C.
Regarding claim 1, CS’644 further teaches a batch reaction, however, the reference fails to teach the continuous reaction by introducing the starting material components in a plate reactor, wherein a. 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 b. the halogenated alkoxyethane is formed at least upon the reaction components mixing, with the so formed halogenated alkoxyethane flowing out of the plate reactor in a reactor effluent. The deficiency is however cured by US’527.
Regarding claim 1, US’527 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.
US’527 teaches that the plate reactor is to provide a continuous flow module, which has good accessibility and is easy to handle, etc., has a good heat transfer performance, and opportunity to control temperature, is suitable for chemical reactions, extractions, separations etc., and has improved pressure properties. The reference further teaches the flow module using plate reactor can be used to perform different reaction types. Accordingly, a skilled artisan would have been motivated to use the continuous plate reactor of US’527 in place of the batch reactor of CS’644 with a reasonable expectation of success in controlling the aforementioned parameters.
Regarding claim 2, the plate reactor is US’527 comprises a stack of fluidic modules ([0015]).
Regarding claim 4, the reference 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 ([0080]), and thus the internal volume is 0.000288 m3 or 288 mL.
Regarding claim 5, as indicated above, 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 CS’644 by controlling such parameters and thus in increasing the amount of the product in the reactor effluent to at least 90% by volume.
Regarding claims 6 and 9, US’527 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]:
The nozzle can be operated under pulsed or un-pulsed modes, and is used for making fluids sprays at a given average flow rate. The nozzle size is selected to give a sufficient flow rate at the pressure available and the pressure level may be set to give a certain droplet size. This means that the droplet size could be adjusted by changing the pump pressure at a constant flow rate. The pump speed may be controlled to give a set flow rate through the open valve i.e. un-pulsed mode.
Thus, 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 reference further teaches that the fluids are mixed prior to passing the channels of the plate reactor:
A mix or a dispersion need sometime to be re-mixed or re-dispersed after some holding time or after a going through a channel plate, then it can be suitable to inject the mix or the dispersion again into the channel. ([0019])
The fluids passing the “three-dimensional” channel may be pure liquids, mixtures of liquids, immiscible liquids, liquids with particles or liquids with dissolved or free gas. ([0030])
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a process for continuous preparation of halogenated alkoxyethane of general formula XCIHC-CF2OR, where X is -Cl or -F and OR is C1-4 alkoxy, the process comprising a step of introducing in a plate reactor reaction components comprising (i) a compound of general formula XCIHC-CYF2, where each of X and Y is independently -Cl or -F, (ii) a base, and (iii) a C1-4 alkanol, wherein a. 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 b. the halogenated alkoxyethane is formed at least upon the reaction components mixing, with the so formed halogenated alkoxyethane flowing out of the plate reactor in a reactor effluent, and c. the base is one that forms a salt soluble in the alkanol during formation of the halogenated alkoxyethane, the base is used in solution with C1-4 alkanol, and the base comprises an alkali metal cation, an ammonium base cation or a phosphonium base cation in view of the teachings of CS’449 and US’527.
Allowable Subject Matter
The subject matter of claims 3, 11 and 17-23 are free of prior art. The closest prior art references have been set forth above.
Regarding claim 3, US’527 fails to teach or suggest the fluidic module(s) is/are at a temperature of from about 100 to about 150 °C. At best, the combination of CS’449 and US’527, a skilled artisan would have kept the temperature of the fluidic module(s) at a temperature of 20 to 50 °C, i.e. the temperature at which CS’449 teaches the production of FClHC-CF2OCH3 from FClHC-CClF2 and would not have been motivated to increase the temperature to the claimed temperature of from about 100 to about 150 °C.
Regarding claim 11, CS’449 fails to teach or even suggest that the compound of general formula XCIHC-CYF2 is Cl2HC-CF3 or FCIHC-CF3, and the halogenated alkoxvethane is CI2HC-CF2OCH3 (methoxvflurane) or CIFHC-CF2OCH3, respectively.
Regarding claim 17, CS’449 further teaches that after completion of the reaction, excess water was added to the reaction mixture, the organic layer was separated, dried and distilled. However, the reference fails to teach a) adding one of an amine and an acid to the reactor effluent or an organic phase separated from the reactor effluent, b) adding a polar liquid to the mixture obtained in step a) to induce phase separation and formation of a polar phase and a separate organic phase, the organic phase containing the halogenated alkoxyethane, and c) adding the other of the amine and the acid not used in step a) to the organic phase obtained in step b) to thereby purify the halogenated alkoxyethane.
In view of the foregoing, claims 3, 11 and 17-23 are deemed unobvious over the combination of CS’644 and US’527.
Conclusion
Claims 1-2, 4-6, 8-12 and 15-16 are rejected and no claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm.
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/MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692
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