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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 12/16/2025 has been entered.
Status of the Claims
The amendment filed on 12/16/2025 has been entered. Claims 1 and 4-5 have been amended and claims 2 and 7-9 have been canceled. Thus claims 1, 3-6 and 10-15 are currently pending and under examination.
Withdrawn Rejection
Claim 1 has been amended to comply with the written description and to be enabled by the specification. Furthermore, claim 5 has been amended to obviate the indefinite language. Thus, the 112(a) and 112(b) rejections of the record have been withdrawn.
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, 3-6 and 10-15 are rejected in a modified form (see underlined) under 35 U.S.C. 103 as being unpatentable over Poshusta (Poshusta, J. C. Patent application publication number US20150126778A1; cited in Office Action 02/06/2024) in view of Han (Han, H-B. et al. “Efficient Preparation of Fluorosulfonyl)(pentafluoroethanesulfonyl)imide and Its Alkali Salts” Chem. Lett. 2010, 39, 472474 and supporting information (SI) pages 1-6; cited in Office Action 02/06/2024).
Regarding claim 1steps b)-c), Poshusta teaches a process for producing
fluorotrifluoromethylsulfonyl imide (FTFSI) from a non-fluoro halogenated trihalomethylsulfonyl imide (i.e., halotrihalomethylsulfonyl imide or XTXSI) compound of the formula:X1—SO2—NR1—SO2—C(X2)3 I
wherein X1 is non-fluoro halide; each of X2 is independently halide; and
R1 is hydrogen, alkyl, or a nitrogen protecting group by reacting XTXSI with hydrogen fluoride under conditions sufficient to produce FTFSI ([0005]).
Poshusta further exemplifies the following reaction ([0050]) wherein a specie of formula (I) is fluorinated with HF to give a specie of formula (II):
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Furthermore, the reference teaches in [0009] that the fluorination does not require a high pressure reaction system but that the scope of the invention includes using a high pressure, high temperature or both. Accordingly, conducting the fluorination reaction at either ambient pressure or at a higher pressure, including the claimed 1.5 to 16 bar, a skilled artisan would still have a reasonable expectation in obtaining the fluorinated product as instantly claimed compound of formula (II). Poshusta also teaches distilling the composition comprising FTFSI.
Regarding claim 1, Poshusta teaches in Fig. 1 and [0048] that the first distillation step (as in claimed step c)) forms a first top stream comprising HF (first stream F’1) and a first bottom stream comprising FTFSI and non-fluorohalogenated trihalomethylsulfonyl imide (XTXSI) (heavy compound) and that the second distillation of the first bottom stream forms a second top stream comprising pure FTFSI (second stream F’2) and a second bottom stream comprising unreacted non-fluorohalogenated trihalomethylsulfonyl imide (XTXSI) (heavy compound) (third stream F’3).
Poshusta is silent about the third stream containing less than 10% by weight of the compound of formula (II) contained in the composition obtained in step b). However, since the reference teaches every limitation of the clamed steps b) to c), there is a prima facie case of anticipation for the third stream in Poshusta to contain less than 10% by weight of the compound of formula (II). See MPEP § 2112.01.
Regarding claim 3, Poshusta also teaches in [0041]-[0042] the following reaction to obtain chlorotrichloromethylsulfonyl imide (CTCSI), specie of the claimed compound of formula (I), by reacting HO—SO2—NH2, specie of compound of formula (A), with a chlorinating agent thionyl chloride:
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Regarding claim 1 step e), while Poshusta teaches the process for obtaining the claimed of compound of formula (II), the reference fails to teach or suggest the claimed process of placing the composition comprising the compound of formula (II) in contact with a composition comprising at least one alkali metal or alkaline-earth metal salt, to give a compound of formula (Ill).
Regarding claims 10 and 11, Poshusta teaches that that the crude product after fluorination is distilled at a reduced pressure to afford CF3SO2NHSO2F in good yield ([0051]), but fails to teach the exact distillation pressure of claim 10 and distillation temperature and/or pressure of claim 11.
The above deficiencies are cured by Han.
Regarding claims 1(e), 4-5 and 12-13, Han teaches (page 4 of SI) obtaining potassium (fluorosulfonyl)(pentafluoroethanesulfonyl)imide (K[(FSO2)(C2F5SO2)N], specie of formula (III)) by reacting K2CO3 powder with (FSO2)(C2F5SO2)NH (specie of formula (II)). Han teaches dissolving (FSO2)(C2F5SO2)NH in dipolar aprotic solvent prior to conversion to K[(FSO2)(C2F5SO2)N] (page 4 of SI).
Han teaches that alkali salts based on (fluorosulfonyl)(pentafluoroethanesulfonyl) imide are used in lithium-ion batteries (LIBs). Thus, a skilled artisan would have been motivated to use the methods of Han in converting the compound of formula (I) of Poshusta to compound of formula (III) having a lithium-ion batteries (LIBs) application.
Regarding claim 6, Han teaches a process of conducting cation exchange of K[(FSO2)(C2F5SO2)N] to obtain Rb[(FSO2)(C2F5SO2)N], Cs[(FSO2)(C2F5SO2)N], Na[(FSO2)(C2F5SO2)N] and Li[(FSO2)(C2F5SO2)N] (pages 4-5 of SI).
Regarding claims 10-11, Han also teaches a process for producing (fluorosulfonyl)(pentafluoroethanesulfonyl)imide ((FSO2)(C2F5SO2)NH, specie of claimed formula (II)), by fluorinating (chlorosulfonyl)(pentafluoroethanesulfonyl)imide ((ClSO2)(C2F5SO2)NH, specie of claimed formula (I)) followed by distilling the resultant mixture at a reduced pressure to obtain crude (FSO2)(C2F5SO2)NH as a colorless liquid and further repeated distillation steps to obtain a high pure FSO2)(C2F5SO2)NH (pages 3-4 of SI). Han teaches that the distillation step is conducted a temperature of 110 °C and at a reduced pressure of 35 mmHg (about 0.047 bar) (page 3 of SI). The temperature, 100 °C, and pressure, 0.03 bar, of claim 11 are merely close to those of Han and MPEP § 2144.05 states that a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. Accordingly, the claimed distillation temperature and pressure are obvious over those of Han absent any showing of unexpected results or criticality.
Regarding claim 14, Han teaches that potassium (fluorosulfonyl)(pentafluoroethanesulfonyl)imide (K[(FSO2)(C2F5SO2)N], specie of formula (III)) is obtained by reacting K2CO3 powder with (FSO2)(C2F5SO2)NH a temperature of 0 °C (page 4 of SI).
Regarding claim 15, Han teaches conducting purification step of K[(FSO2)(C2F5SO2)N].
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 comprising a step (b) of fluorinating a compound of formula (I) R1-(SO2)-NH-(SO2)-CI in which R1 represents one of the following radicals: Cl, F, CF3, CHF2, CH2F, C2HF4, C2H2F3, C2H3F2, C2F5, C3F7, C3H4F3, C3HF6, C4F9, C4H2F7, C4H4F5, C5F11, C6F13, C7F15, C8F17 or C9F19--R4; with at least one fluorinating agent at a pressure ranging from 1.5 to 16 bar to form a composition comprising a compound of formula (II) R2-(SO2)-NH-(SO2)-F in which R2 represents one of the following radicals: F, CF3, CHF2, CH2F, C2HF4, C2H2F3, C2H3F2, C2F5, C3F7, C3H4F3, C3HF6, C4F9, C4H2F7, C4H4F5, C5F11, C6F13, C7F15, C8F17 or C9F19; a step (c) of distilling the composition comprising the compound of formula (II) to form: a recoverable first stream F' 1 comprising HF, optionally the organic solvent OS1 and/or optionally HCl, said stream F' 1 being gaseous or liquid, a recoverable second steam F'2 comprising the compound of formula (II), and a recoverable third stream F'3 comprising heavy compounds and the compound of formula (II), said stream F'3 containing less than 10% by weight of the compound of formula (II) contained in the composition obtained in step b); and a step (e) of placing the composition comprising the stream F’2 comprising the compound of formula (II) in contact with a composition comprising at least one alkali metal or alkaline-earth metal salt, to give a compound of formula (Ill) in view of the teachings of Poshusta and Han.
Claims 1, 3, 12 and 14 are rejected in a modified form (see underlined) under 35 U.S.C. 103 as being unpatentable over Schmidt (Schmidt, G. et al. Patent application publication number US2017/0047607A1; cited in IDS 04/20/2021) in view of Poshusta (Poshusta, J. C. Patent application publication number US20150126778A1; cited in Office Action 02/06/2024).
Regarding claim 1 step b), Schmidt teaches in [0099] a process for producing fluorotrifluoromethylsulfonyl imide of formula
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by fluorinating a compound of the formula:
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wherein
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Schmidt teaches that the fluorination process is conducted by reacting formula (IIa) with anhydrous hydrofluoric acid at a pressure of between 0 and 16 bar absolute ([0037]).
Regarding claims 1 step e), 12 and 14, the reference further teaches in claim 16 and paras. [0121] and [0127] that the fluoro compound of formula (IIIa) obtained is neutralized with a base chosen from alkali metal carbonates, alkaline-earth metal carbonates, alkali metal hydroxides, alkaline-earth metal hydroxides, tertiary amines in a polar organic solvent, and mixtures thereof at a temperature of between −10° C. and 40° C. to obtain a compound of formula:
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in which M represents a monovalent cation.
Regarding claim 3, Schmidt also teaches in claim 1 obtaining the above compound of formula (IIa) by the reaction of formula
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with a sulfureous avid and a chlorinating agent.
Regarding claim 1 step c), Schmidt fails to teach distilling the compound of formula (II) to form stream containing the compound of formula (II).
However, the deficiency is cured by Poshusta.
Poshusta, like Schmidt, teaches a process for producing
fluorotrifluoromethylsulfonyl imide (FTFSI) from a non-fluoro halogenated trihalomethylsulfonyl imide (i.e., halotrihalomethylsulfonyl imide or XTXSI) compound of the formula:X1—SO2—NR1—SO2—C(X2)3 I
wherein X1 is non-fluoro halide; each of X2 is independently halide; and
R1 is hydrogen, alkyl, or a nitrogen protecting group by reacting XTXSI with hydrogen fluoride under conditions sufficient to produce FTFSI ([0005]).
Poshusta further exemplifies the following reaction ([0050]) wherein a specie of formula (I) is fluorinated with HF to give a specie of formula (II):
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Furthermore, the reference teaches in [0009] that the fluorination does not require a high pressure reaction system but that the scope of the invention includes using a high pressure, high temperature or both. Poshusta also teaches distilling the composition comprising FTFSI.
Accordingly, using the methods of Poshusta in the process of Schmidt, a skilled artisan has a reasonable expectation of success in purifying Schmidt’s compound of formula (IIa).
Poshusta teaches in Fig. 1 and [0048] that the first distillation step (as in claimed step c)) forms a first top stream comprising HF (first stream F’1) and a first bottom stream comprising FTFSI and non-fluorohalogenated trihalomethylsulfonyl imide (XTXSI) (heavy compound) and that the second distillation of the first bottom stream forms a second top stream comprising pure FTFSI (second stream F’2) and a second bottom stream comprising unreacted non-fluorohalogenated trihalomethylsulfonyl imide (XTXSI) (heavy compound) (third stream F’3).
Poshusta is silent about the third stream containing less than 10% by weight of the compound of formula (II) contained in the composition obtained in step b). However, since the reference teaches every limitation of the clamed steps b) to c), there is a prima facie case of anticipation for the third stream in Poshusta to contain less than 10% by weight of the compound of formula (II). See MPEP § 2112.01.
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 comprising a step (b) of fluorinating a compound of formula (I) R1-(SO2)-NH-(SO2)-CI in which R1 represents one of the following radicals: Cl, F, CF3, CHF2, CH2F, C2HF4, C2H2F3, C2H3F2, C2F5, C3F7, C3H4F3, C3HF6, C4F9, C4H2F7, C4H4F5, C5F11, C6F13, C7F15, C8F17 or C9F19--R4; with at least one fluorinating agent at a pressure ranging from 1.5 to 16 bar to form a composition comprising a compound of formula (II) R2-(SO2)-NH-(SO2)-F in which R2 represents one of the following radicals: F, CF3, CHF2, CH2F, C2HF4, C2H2F3, C2H3F2, C2F5, C3F7, C3H4F3, C3HF6, C4F9, C4H2F7, C4H4F5, C5F11, C6F13, C7F15, C8F17 or C9F19; a step (c) of distilling the composition comprising the compound of formula (II) to form: a recoverable first stream F' 1 comprising HF, optionally the organic solvent OS1 and/or optionally HCl, said stream F' 1 being gaseous or liquid, a recoverable second steam F'2 comprising the compound of formula (II), and a recoverable third stream F'3 comprising heavy compounds and the compound of formula (II), said stream F'3 containing less than 10% by weight of the compound of formula (II) contained in the composition obtained in step b); and a step (e) of placing the composition comprising the stream F’2 comprising the compound of formula (II) in contact with a composition comprising at least one alkali metal or alkaline-earth metal salt, to give a compound of formula (Ill) in view of the teachings of Schmidt and Poshusta.
Claims 4-6, 10-11, 13 and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Schmidt (Schmidt, G. et al. Patent application publication number US2017/0047607A1; cited in IDS 04/20/2021) in view of Poshusta (Poshusta, J. C. Patent application publication number US20150126778A1; cited in Office Action 02/06/2024) as applied to claims 1-3, 7-9, 12 and 14 above, and further in view of Han (Han, H-B. et al. “Efficient Preparation of Fluorosulfonyl)(pentafluoroethanesulfonyl)imide and Its Alkali Salts” Chem. Lett. 2010, 39, 472474 and supporting information (SI) pages 1-6; cited in Office Action 02/06/2024).
The teachings of Schmidt and Poshusta have been set forth above. However, the references fail to teach the limitations of claims 4-6, 10-11, 13 and 15.
However, these are cured by Han.
Regarding, 4-5 and 13, Han teaches (page 4 of SI) obtaining potassium (fluorosulfonyl)(pentafluoroethanesulfonyl)imide (K[(FSO2)(C2F5SO2)N], specie of formula (III)) by reacting K2CO3 powder with (FSO2)(C2F5SO2)NH (specie of formula (II)). Han teaches dissolving (FSO2)(C2F5SO2)NH in dipolar aprotic solvent prior to conversion to K[(FSO2)(C2F5SO2)N] (page 4 of SI).
Regarding claim 6, Han teaches a process of conducting cation exchange of K[(FSO2)(C2F5SO2)N] to obtain Rb[(FSO2)(C2F5SO2)N], Cs[(FSO2)(C2F5SO2)N], Na[(FSO2)(C2F5SO2)N] and Li[(FSO2)(C2F5SO2)N] (pages 4-5 of SI).
Regarding claims 10-11, while Schmidt teaches that that the crude product after fluorination is distilled at a reduced pressure to afford CF3SO2NHSO2F in good yield ([0051]), it fails to teach the exact distillation pressure of claim 10 and distillation temperature and/or pressure of claim 11. However, Han also teaches a process for producing (fluorosulfonyl)(pentafluoroethanesulfonyl)imide ((FSO2)(C2F5SO2)NH, specie of claimed formula (II)), by fluorinating (chlorosulfonyl)(pentafluoroethanesulfonyl)imide ((ClSO2)(C2F5SO2)NH, specie of claimed formula (I)) followed by distilling the resultant mixture at a reduced pressure to obtain crude (FSO2)(C2F5SO2)NH as a colorless liquid and further repeated distillation steps to obtain a high pure FSO2)(C2F5SO2)NH (pages 3-4 of SI). Han teaches that the distillation step is conducted a temperature of 110 °C and at a reduced pressure of 35 mmHg (about 0.047 bar) (page 3 of SI). The temperature, 100 °C, and pressure, 0.03 bar, of claim 11 are merely close to those of Han and MPEP § 2144.05 states that a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. Accordingly, the claimed distillation temperature and pressure are obvious over those of Han absent any showing of unexpected results or criticality.
Regarding claim 15, Han teaches conducting purification step of K[(FSO2)(C2F5SO2)N].
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct the process of claims 4-6, 10-11, 13 and 15 in view of the combination of Schmidt, Poshusta and Han.
Response to Arguments
Applicant’s arguments that Poshusta fails to teach F’3 as containing less than 10% by weight of the compound of formula (II) contained in the composition obtained in step b) and that Figure 1 of the reference fails to include any relevant amounts of specific components contained within the diagramed streams.
The arguments have been considered but are not persuasive in view of the modified (underlined) rationale set forth in the rejections that address the amount of the compound of formula (II) contained in the third stream F’3.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1, 3-6 and 10-15 are rejected in a modified form (see underlined) on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of U.S. Patent No. 10,128,525 (‘525) in view of Poshusta (Poshusta, J. C. et al. patent application publication number US2015/0126778A1; cited in Office Action 02/06/2024) and Han (Han, H-B. et al. “Efficient Preparation of Fluorosulfonyl)(pentafluoroethanesulfonyl)imide and Its Alkali Salts” Chem. Lett. 2010, 39, 472474 and supporting information (SI) pages 1-6; cited in Office Action 02/06/2024).
Both instant claims and the claims of ‘525 are drawn to a fluorination method of sulfonyl imide where a chloro group is replaced by fluoro group to produce a composition comprising fluorinated sulfonyl imide, i.e. instant compound of formula (II) and ‘525’s compound of formula (III).
Regarding claim 1 step (b), claim 1 of ‘525 fails to recite that the fluorinating reaction is conducted at a pressure ranging from 1.5 to 16 bar, however, claim 10 of ‘525 recites that the fluorination step is performed at a pressure of between 0 and 16 bar absolute. Hence a skilled artisan would arrive at instantly claimed step (b) by combining the process of claims 1 and 10 of ‘525.
Regarding claim 1, the claims of ‘525 fail to recite the instantly claimed step c) of distilling the composition obtained from the fluorination step. However, the deficiency is cured by Poshusta.
Poshusta teaches a process for producing fluorotrifluoromethylsulfonyl imide (FTFSI) from a non-fluoro halogenated trihalomethylsulfonyl imide (i.e., halotrihalomethylsulfonyl imide or XTXSI) compound of the formula:X1—SO2—NR1—SO2—C(X2)3 I
wherein X1 is non-fluoro halide; each of X2 is independently halide; and
R1 is hydrogen, alkyl, or a nitrogen protecting group by reacting XTXSI with hydrogen fluoride under conditions sufficient to produce FTFSI ([0005]).
Poshusta further exemplifies the following reaction ([0050]) wherein a specie of formula (I) is fluorinated with HF to give a specie of formula (II):
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Poshusta teaches in Fig. 1 and [0048] that the first distillation step (as in claimed step c)) forms a first top stream comprising HF (first stream F’1) and a first bottom stream comprising FTFSI and non-fluorohalogenated trihalomethylsulfonyl imide (XTXSI) (heavy compound) and that the second distillation of the first bottom stream forms a second top stream comprising pure FTFSI (second stream F’2) and a second bottom stream comprising unreacted non-fluorohalogenated trihalomethylsulfonyl imide (XTXSI) (heavy compound) (third stream F’3).
Poshusta is silent about the third stream containing less than 10% by weight of the compound of formula (II) contained in the composition obtained in step b). However, since the reference teaches every limitation of the clamed steps b) to c), there is a prima facie case of anticipation for the third stream in Poshusta to contain less than 10% by weight of the compound of formula (II). See MPEP § 2112.01.
Accordingly, using the distillation step of Poshusta in the process of claim 1 of ‘525, a skilled artisan would have a reasonable expectation of success in arriving at the instantly claimed process steps c).
Regarding claim 1 step (e), while claim 1 of ‘525 recites the formation of formula (III), the claim fails to recite that the compound is obtained by placing the composition comprising the compound of formula (II) in contact with a composition comprising at least one alkali metal or alkaline-earth metal salt. However, claims 15-16 of ‘525 recite that the compound of formula R2—(SO2)—NM-(SO2)—F is obtained by neutralization of R2—(SO2)—NH—(SO2)—F, wherein M is a monovalent cation but fail to recite the method of instant step (e). The deficiency is cured by Han by teaching the method for obtaining potassium (fluorosulfonyl)(pentafluoroethanesulfonyl)imide (K[(FSO2)(C2F5SO2)N], specie of formula (III)) by reacting K2CO3 powder with (FSO2)(C2F5SO2)NH (specie of formula (II)). Accordingly, a skilled artisan would arrive at the instant claim 1 step (e) by combining claims 1 and 14-15 and the teachings of Han.
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 comprising a step (b) of fluorinating a compound of formula (I) R1-(SO2)-NH-(SO2)-CI in which R1 represents one of the following radicals: Cl, F, CF3, CHF2, CH2F, C2HF4, C2H2F3, C2H3F2, C2F5, C3F7, C3H4F3, C3HF6, C4F9, C4H2F7, C4H4F5, C5F11, C6F13, C7F15, C8F17 or C9F19--R4; with at least one fluorinating agent at a pressure ranging from 1.5 to 16 bar to form a composition comprising a compound of formula (II) R2-(SO2)-NH-(SO2)-F in which R2 represents one of the following radicals: F, CF3, CHF2, CH2F, C2HF4, C2H2F3, C2H3F2, C2F5, C3F7, C3H4F3, C3HF6, C4F9, C4H2F7, C4H4F5, C5F11, C6F13, C7F15, C8F17 or C9F19; a step (c) of distilling the composition comprising the compound of formula (II) to form: a recoverable first stream F' 1 comprising HF, optionally the organic solvent OS1 and/or optionally HCl, said stream F' 1 being gaseous or liquid, a recoverable second steam F'2 comprising the compound of formula (II), and a recoverable third stream F'3 comprising heavy compounds and the compound of formula (II), said stream F'3 containing less than 10% by weight of the compound of formula (II) contained in the composition obtained in step b); and a step (e) of placing the composition comprising the stream F’2 comprising the compound of formula (II) in contact with a composition comprising at least one alkali metal or alkaline-earth metal salt, to give a compound of formula (Ill) in view of claims of ‘525 and the teachings of Poshusta and Han.
Claims 1, 3-6 and 10-15 are rejected in a modified form (see underlined) on the ground of nonstatutory double patenting as being unpatentable over claims 1-16 of U.S. Patent No. 12,024,425B2 (‘425) in view of Poshusta (Poshusta, J. C. et al. patent application publication number US2015/0126778A1; cited in Office Action 02/06/2024).
Both instant claims and the claims of ‘425 are drawn to a fluorination method of sulfonyl imide where a chloro group is replaced by fluoro group to produce a composition comprising fluorinated sulfonyl imide, i.e. instant compound of formula (II) and ‘425’s compound of formula (I).
Regarding claim 1, the claims of ‘425 fail to recite that the fluorinating reaction is conducted at a pressure ranging from 1.5 to 16 bar and the instantly claimed step c) of distilling the composition obtained from the fluorination step. However, the deficiencies are cured by Poshusta.
Poshusta further exemplifies the following reaction ([0050]) wherein a specie of formula (I) is fluorinated with HF to give a specie of formula (II):
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The reference teaches in [0009] that the fluorination does not require a high pressure reaction system but that the scope of the invention includes using a high pressure, high temperature or both. Accordingly, conducting the fluorination reaction at either ambient pressure or at a higher pressure, including the claimed 1.5 to 16 bar, a skilled artisan would still have a reasonable expectation in obtaining the fluorinated product as instantly claimed compound of formula (II).
Furthermore, Poshusta teaches in Fig. 1 and [0048] that the first distillation step (as in claimed step c)) forms a first top stream comprising HF (first stream F’1) and a first bottom stream comprising FTFSI and non-fluorohalogenated trihalomethylsulfonyl imide (XTXSI) (heavy compound) and that the second distillation of the first bottom stream forms a second top stream comprising pure FTFSI (second stream F’2) and a second bottom stream comprising unreacted non-fluorohalogenated trihalomethylsulfonyl imide (XTXSI) (heavy compound) (third stream F’3).
Poshusta is silent about the third stream containing less than 10% by weight of the compound of formula (II) contained in the composition obtained in step b). However, since the reference teaches every limitation of the clamed steps b) to c), there is a prima facie case of anticipation for the third stream in Poshusta to contain less than 10% by weight of the compound of formula (II). See MPEP § 2112.01.
Accordingly, using the distillation step of Poshusta in the process of claim 1 of ‘425, a skilled artisan would have a reasonable expectation of success in arriving at the instantly claimed process steps c).
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 comprising a step (b) of fluorinating a compound of formula (I) R1-(SO2)-NH-(SO2)-CI in which R1 represents one of the following radicals: Cl, F, CF3, CHF2, CH2F, C2HF4, C2H2F3, C2H3F2, C2F5, C3F7, C3H4F3, C3HF6, C4F9, C4H2F7, C4H4F5, C5F11, C6F13, C7F15, C8F17 or C9F19--R4; with at least one fluorinating agent at a pressure ranging from 1.5 to 16 bar to form a composition comprising a compound of formula (II) R2-(SO2)-NH-(SO2)-F in which R2 represents one of the following radicals: F, CF3, CHF2, CH2F, C2HF4, C2H2F3, C2H3F2, C2F5, C3F7, C3H4F3, C3HF6, C4F9, C4H2F7, C4H4F5, C5F11, C6F13, C7F15, C8F17 or C9F19; a step (c) of distilling the composition comprising the compound of formula (II) to form: a recoverable first stream F' 1 comprising HF, optionally the organic solvent OS1 and/or optionally HCl, said stream F' 1 being gaseous or liquid, a recoverable second steam F'2 comprising the compound of formula (II), and a recoverable third stream F'3 comprising heavy compounds and the compound of formula (II), said stream F'3 containing less than 10% by weight of the compound of formula (II) contained in the composition obtained in step b); and a step (e) of placing the composition comprising the stream F’2 comprising the compound of formula (II) in contact with a composition comprising at least one alkali metal or alkaline-earth metal salt, to give a compound of formula (Ill) in view of claims of ‘425 and the teachings of Poshusta.
Conclusion
Claims 1, 3-6 and 10-15 are rejected and no claims are allowed.
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/MEDHANIT W BAHTA/Primary Examiner, Art Unit 1692