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 amendment filed on 01/07/2026 has been entered. Claims 25-26 and 29-30 have been amended. Thus claims 25-26, 28-32 and 35-43 are currently pending and are under current examination.
Withdrawn Rejection
The indefinite language of claim 26 has been withdrawn in view of the amendment.
Claim Rejections - 35 USC § 112 – New Matter
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 25-26, 28-32 and 35-43 stand rejected in a modified form under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention. The rejection has been set forth in the previous Office Action 10/08/2025 and is reiterated herein.
The following claims recite the following limitations that introduce new matter.
Claim 25 recites (i) chilling the HF and catalyst to about -10 °C to about -30 °C, adding the 2-chloro-3,3,3-trifluoropropene to the reactor, and heating the mixture to about 0 °C to about 65 °C and stopping the reaction upon reaching the about 0 °C to about 65 °C… (ii) wherein a selectivity from the 2-chloro-3,3,3-trifluoropropene to the hydrofluoroalkane is about 99 mole % or greater and the hydrofluoroalkane is 2-chloro-1,1,1,2-tetrafluoropropane.
Claim 26, that encompasses claim 25, recites the conversion of at least 98 mole %. Note: the claimed conversion is interpreted as the conversion from 2-choro-3,3,3-trifluoropropene to the hydrofluoroalkane which is 2-chloro-1,1,12-tetrafluoropropane.
Claims 29-30 and 36-43, that encompasses claim 25, recite a narrower chilling, heating or stopping temperature.
Claim 32, that encompasses claim 25, recites wherein the reacting is continuous.
Claim 35, that encompasses claim 25, recite a conversion from 2-chloro-3,3,3-trifluoropropene to hydrofluoroalkane is at least 98 mole %.
Regarding (a)(i) and (c), the instant specification appears devoid of such description regarding the specific steps of 25 other than in Examples 1-2, however, the chilling temperature, the heating temperature, and the stopping temperature in these examples are narrow in claims 25, 29-30 and 36-43 (see below).
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The above examples fail to disclose either explicitly or implicitly, the entire range of the chilling temperature, the heating temperature, and the stopping temperature. Furthermore, the non-exemplified embodiment of the specification discloses that the hydrofluorination reaction is conducted at a temperature ranging from about -30 °C to about 65 °C ([0038]). This temperature range is the temperature at which the hydrofluorination reaction is conducted, i.e. the reaction of 2-chloro-3,3,3-trifluoropropene with HF in the presence of the SbF5 catalyst. However, nowhere in this disclosure describes the step-wise change in the temperature, including the chilling temperature after only loading HF and the catalyst in the reactor, the heating temperature from the chilling temperature after adding 2-chloro-3,3,3-trifluoropropene, and the stopping temperature after the heating temperature.
Regarding (a)(ii), the entirety of the claimed selectivity is also not supported by the original disclosure. As discussed above, the only disclosure that specifies the step-wise chilling temperature, heating temperature and stopping temperature is in Examples 1-2. However, as shown in Tables 1-2, the selectivities to 2-chloro-1,1,1,2-tetrafluoropropane (244bb) are narrower, i.e. 99.42% and 98.236%, respectively.
Regarding (b) and (e), the entirety of the claimed conversions from 2-choro-3,3,3-trifluoropropene to 2-chloro-1,1,12-tetrafluoropropane is also not supported by the original disclosure. As discussed above, the only disclosure that specifies the step-wise chilling temperature, heating temperature and stopping temperature is in Examples 1-2. However, nowhere in these examples describe the conversion of 2-choro-3,3,3-trifluoropropene to 2-chloro-1,1,12-tetrafluoropropane as claimed.
Regarding (d), as indicated above, claim 32 encompasses all the limitations of claim 25 and recites that the reacting is continuous, however, Examples 1-2 that support the specific steps of claim 25 fail to support that the reaction is a continuous reacting. Examples 1-2 stops the reaction once a certain temperature is reached by quenching the catalyst with water and transferring the organic layer for GC-MS analysis. This process where the reaction is stopped and analyzed is equivalent to a batch reaction and not to a continuous process, in which the latter occurs without interruption, where reactants are constantly added and products are continuously.
Thus, at the time the application was filed, a skilled artisan would not recognize from the disclosure that Applicant was in possession of the limitations set forth above.
MPEP § 2163.06 notes:
If new matter is added to the claims, the examiner should reject the claims under 35 U.S.C. 112(a) or pre-AIA 35 U.S.C. 112, first paragraph - written description requirement. In re Rasmussen, 650 F.2d 1212, 211 USPQ 323 (CCPA 1981).
MPEP § 2163.02 states:
Whenever the issue arises, the fundamental factual inquiry is whether the specification conveys with reasonable clarity to those skilled in the art that, as of the filing date sought, applicant was in possession of the invention as now claimed. See, e.g., Vas-Cath, Inc. v. Mahurkar, 935 F.2d 1555, 1563-64, 19 USPQ2d 1111, 1117 (Fed. Cir. 1991). An applicant shows possession of the claimed invention by describing the claimed invention with all of its limitations using such descriptive means as words, structures, figures, diagrams, and formulas that fully set forth the claimed invention. Lockwood v. Am. Airlines, Inc., 107 F.3d 1565, 1572, 41 USPQ2d 1961, 1966 (Fed. Cir. 1997). Possession may be shown in a variety of ways including description of an actual reduction to practice, or by showing that the invention was "ready for patenting" such as by the disclosure of drawings or structural chemical formulas that show that the invention was complete, or by describing distinguishing identifying characteristics sufficient to show that the applicant was in possession of the claimed invention. See, e.g., Pfaff v. Wells Elecs., Inc., 525 U.S. 55, 68, 119 S.Ct. 304, 312, 48 USPQ2d 1641, 1647 (1998); Regents of the Univ. of Cal. v. Eli Lilly, 119 F.3d 1559, 1568, 43 USPQ2d 1398, 1406 (Fed. Cir. 1997); Amgen, Inc. v. Chugai Pharm., 927 F.2d 1200, 1206, 18 USPQ2d 1016, 1021 (Fed. Cir. 1991) (one must define a compound by "whatever characteristics sufficiently distinguish it").
MPEP § 2163.06 further notes:
When an amendment is filed in reply to an objection or rejection based on 35 U.S.C. 112(a) or pre-AIA 35 U.S.C. 112, first paragraph, a study of the entire application is often necessary to determine whether or not "new matter" is involved. Applicant should therefore specifically point out the support for any amendments made to the disclosure.
This is a new matter rejection.
Claims 26, 28-32 and 35-43 also introduce new matter for depending on claim 25.
Response to Arguments
Applicant argues limitations indicated in (a)-(c) and (e) are supported by paragraphs [0038] and examples in [0065]-[0066] of the specification and limitation regarding (d) is supported by paragraph ([0029]).
Applicant also refers to the argument presented in the remarks 05/29/2025 with respect to the calculation of selectivity obtained in the examples, i.e. 99.89% (Example 1) and 99.02% (Example 2).
The arguments have been considered but were not found persuasive.
Regarding (a)-(c) and (e)
The specific reaction steps of claim 19 of loading.., evacuating the reactor, chilling.., adding the 2-chloro-3,3,3-trifluoropropene…, heating the mixture…, and stopping the reaction…are not supported by the entirety of the nonexemplified embodiment of the specification. The examiner maintains that the exemplified loading.., evacuating the reactor, chilling.., adding the 2-chloro-3,3,3-trifluoropropene…, heating the mixture…, and stopping the reaction…are not described in the specification as embodiments that can be combined with the entire range of -30 °C to about 65 °C of paragraph [0038]. The aforementioned claimed specific steps are only supported by Examples 1-2 in which the chilling temperature, the heating temperature, and the weight percent of SbF5 are narrower than those of claim 25.
The non-exemplified embodiment of the specification discloses that the hydrofluorination reaction is conducted at a temperature ranging from about -30 °C to about 65 °C ([0038]). This temperature range, however, is the temperature at which the hydrofluorination reaction is conducted, i.e. the reaction of 2-chloro-3,3,3-trifluoropropene with HF in the presence of the SbF5 catalyst. Nowhere in this disclosure, including paragraph [0038], describes the step-wise change in the temperature as claimed, including the chilling temperature after only loading HF and the catalyst in the reactor, the heating temperature from the chilling temperature after adding 2-chloro-3,3,3-trifluoropropene, and the stopping temperature after the heating temperature.
Furthermore, nowhere in the above examples that conducts the specific steps of claim 25 disclose narrower selectivity, even after calculation as Applicant argues, but does not support the entire selectivity range of 99 mole% or greater as recited in claim 25.
The examiner also maintains that these examples do not describe the conversion rates of 2-chloro-3,3,3-trifluoropropene to the hydrofluoroalkane as recited in claims 26 and 35.
Regarding (d)
While the examiner agrees the disclosure of a continuous reaction is set forth in [0029], the examiner maintains that Applicant was not in possession of conducting the continuous reaction in the step-wise process of claim 25. Nowhere in the non-exemplified embodiment discloses that the continuous process can be applied to when the reaction includes the steps of chilling temperature after only loading HF and the catalyst in the reactor, heating temperature from the chilling temperature after adding 2-chloro-3,3,3-trifluoropropene, and stopping temperature after the heating temperature and thus would not warrant the possession of claim 32. Examples 1-2 are the only parts of the disclosure that are encompassed in claim 25, and as explained earlier, these examples are not run in a continuous mode.
In view of the foregoing, the 112(a) rejection of the record is maintained for introducing new matter.
Allowable Subject Matter
The subject matter of claims 25-26, 28-32 and 35-43 is free of prior art reference. The closest prior art references are Han (Han, S. et al. Patent number CN104140354A, Published Nov. 12, 2014; cited in IDS 03/31/2022 and machine translation cited on 02/01/2023) and Mahler (Mahler, B. A. et al. Patent application publication number US2011/0031436A1; cited in IDS 02/01/2023).
The teachings of Han and Mahler have been made of record in the Office Actions 11/08/2023 and 02/12/2025, respectively, however the references fail to teach or suggest the claimed method for preparing 2-chloro-1,1,1,2-tetrafluoropropane (HCFC- 244bb) comprising: reacting HF with 2-chloro-3,3,3-trifluoropropene in a liquid phase in the presence of a catalyst consisting essentially of SbF5, the reacting comprising: loading the HF and the catalyst into a reactor; evacuating the reactor; chilling the HF and the catalyst to about -10 °C to about -30 °C; adding the 2-chloro-3,3,3-trifluoropropene to the reactor; and heating the mixture to about 0 °C to about 65 °C and stopping the reaction upon reaching the about 0 °C to about 65 °C; to produce a hydrofluoroalkane composition a hydrofluoroalkane composition comprising a hydrofluoroalkane, wherein a percent selectivity from the 2-chloro-3,3,3- trifluoropropene to the hydrofluoroalkane is about 99 mole % or greater and the hydrofluoroalkane is 2-chloro-1,1,1,2-tetrafluoropropane.
Conclusion
Claims 25-26, 28-32 and 35-43 stand rejected and no claims are allowed.
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692