JP4198992B2 - ハロスルホニル基、又はジハロホスホニル基を含む化合物をフッ素化するための方法 - Google Patents
ハロスルホニル基、又はジハロホスホニル基を含む化合物をフッ素化するための方法 Download PDFInfo
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- JP4198992B2 JP4198992B2 JP2002554620A JP2002554620A JP4198992B2 JP 4198992 B2 JP4198992 B2 JP 4198992B2 JP 2002554620 A JP2002554620 A JP 2002554620A JP 2002554620 A JP2002554620 A JP 2002554620A JP 4198992 B2 JP4198992 B2 JP 4198992B2
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- 238000000034 method Methods 0.000 title claims abstract description 42
- 150000001875 compounds Chemical class 0.000 title claims abstract description 30
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims abstract description 21
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 16
- 239000011737 fluorine Substances 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical group 0.000 claims abstract description 12
- 150000001768 cations Chemical class 0.000 claims abstract description 11
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 7
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 7
- 125000005496 phosphonium group Chemical group 0.000 claims abstract description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 3
- -1 fluoride cation Chemical class 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 150000003254 radicals Chemical class 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 150000001408 amides Chemical class 0.000 claims description 6
- 239000003444 phase transfer catalyst Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 150000001723 carbon free-radicals Chemical class 0.000 claims description 4
- 239000012025 fluorinating agent Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- LYGJENNIWJXYER-BJUDXGSMSA-N nitromethane Chemical group [11CH3][N+]([O-])=O LYGJENNIWJXYER-BJUDXGSMSA-N 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 abstract description 8
- 239000003792 electrolyte Substances 0.000 abstract description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract description 5
- 238000003682 fluorination reaction Methods 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 3
- 150000003949 imides Chemical class 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- XJHCXCQVJFPJIK-UHFFFAOYSA-M cesium fluoride Substances [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- PVMUVDSEICYOMA-UHFFFAOYSA-N n-chlorosulfonylsulfamoyl chloride Chemical compound ClS(=O)(=O)NS(Cl)(=O)=O PVMUVDSEICYOMA-UHFFFAOYSA-N 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 229910013870 LiPF 6 Inorganic materials 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 150000002222 fluorine compounds Chemical class 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910001416 lithium ion Inorganic materials 0.000 description 3
- 229910003002 lithium salt Inorganic materials 0.000 description 3
- 159000000002 lithium salts Chemical class 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000004062 sedimentation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- 229910000733 Li alloy Inorganic materials 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000003983 crown ethers Chemical class 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000001989 lithium alloy Substances 0.000 description 2
- JMIHYOKWULLMQX-UHFFFAOYSA-N n-(trifluoromethylsulfonyl)sulfamoyl chloride Chemical compound FC(F)(F)S(=O)(=O)NS(Cl)(=O)=O JMIHYOKWULLMQX-UHFFFAOYSA-N 0.000 description 2
- KTQDYGVEEFGIIL-UHFFFAOYSA-N n-fluorosulfonylsulfamoyl fluoride Chemical compound FS(=O)(=O)NS(F)(=O)=O KTQDYGVEEFGIIL-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 150000004714 phosphonium salts Chemical group 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 1
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 description 1
- 238000006677 Appel reaction Methods 0.000 description 1
- 241001517013 Calidris pugnax Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001265 acyl fluorides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000011244 liquid electrolyte Substances 0.000 description 1
- VDVLPSWVDYJFRW-UHFFFAOYSA-N lithium;bis(fluorosulfonyl)azanide Chemical compound [Li+].FS(=O)(=O)[N-]S(F)(=O)=O VDVLPSWVDYJFRW-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical class [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920006112 polar polymer Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- MHEBVKPOSBNNAC-UHFFFAOYSA-N potassium;bis(fluorosulfonyl)azanide Chemical compound [K+].FS(=O)(=O)[N-]S(F)(=O)=O MHEBVKPOSBNNAC-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical class FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/087—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms
- C01B21/093—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms containing also one or more sulfur atoms
- C01B21/0935—Imidodisulfonic acid; Nitrilotrisulfonic acid; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/097—Compounds containing nitrogen and non-metals and optionally metals containing phosphorus atoms
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0568—Liquid materials characterised by the solutes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Secondary Cells (AREA)
Description
式中、
・MはH、アルカリ金属、4級ホスホニウム基又は4級アンモニウム基を表す;
・ZはNを表す;
・YがSO2を表してmが1であるか、又はYがPOであってmが2であるかのいずれかを表す;
・R1はハメットσpパラメーターが0.4より大きい電子吸引性基を表す;
・Xはフッ素以外のハロゲンを表す。
・X’SO2−ラジカル及び(X’)2PO−ラジカルで、ここで基X’又は2つの基X’が互いに独立して以下のものを表す:
・ハロゲン、
・R7CF2−ラジカルで、ここでR7は、F以外のハロゲン又は、好ましくは最大で 15の炭素原子を有する炭素ラジカル;
・炭素原子数15以下を有していると好ましい、ペルハロゲン化ラジカルRFで、式R8 (CX”2)p−に相当するものであり、ここで:
*X”基のそれぞれが、互いに独立して、F、Cl又は炭素原子1〜5(好ましくは 炭素原子2)を有するペルフルオロアルキルラジカルであって、X”基の内の少なく とも1つがFであり、好ましくは硫黄又はリンに結合した炭素上に担持されている。 pは1又は2である;
*R8は電子吸引性原子又はラジカルで、そのσpが0より大きく(好ましくは、0. 1より大きく、より好ましくは0.2より大きい)、それに官能基がある場合には、 反応条件下では不活性な、例えば、F又は最大で8の炭素原子を有するペルフルオロ アルキルである;
・σpが0.4より大きい各種ラジカルで、特にゲリー・マーチ(Gerry March)による『高等有機化学(Advanced Organic Chemistry)第3版』、p.244に記載されているような、例えば、COOR’、COR’、SO2R’、PO(R’)2又はPO(OR’)2で、ここでR’は1〜15の炭素原子を有するアルキルラジカル又は6〜20の炭素原子を有するアリールラジカルであるのが好ましい。
フッ素化反応剤として使用可能な溶解性の高いイオン性フルオリドを、溶解性の低いフルオリド反応剤と組み合わせて、相間移動触媒として使用することができる。その例として、オニウムフルオリド及びセシウムフルオリドがある。
Claims (22)
- 少なくとも1つのハロスルホニル基、又はジハロホスホリル基(ただしここで、ハロゲンはフッ素以外のもの)及び少なくとも1つの強い電子吸引性基を含む化合物(I)をフッ素化するための方法であって、適宜溶媒中で、フッ素化剤を前記化合物と反応させることから成り、ここで、前記フッ素化剤とは1価カチオンのイオン性フルオリドであって、化合物(I)は次式に相当するものである方法:
・MはH、アルカリ金属、4級ホスホニウム基又は4級アンモニウム基を表す;
・ZはNを表す;
・YはSO2を表してmが1であるか、又はYがPOであってmが2であるかのいずれかを表す;
・R1はハメットσpパラメーターが0.4より大きい電子吸引性基を表す;
・Xはフッ素以外のハロゲンを表す。 - 大気圧で実施する、請求項1に記載の方法。
- 温度180℃未満で実施する、請求項1に記載の方法。
- 前記1価イオン性フルオリドがKF又はCsFである、請求項1に記載の方法。
- 前記1価イオン性フルオリドが、テトラアルキルアンモニウム、テトラアルキルホスホニウム又はジアルキルスルホニウムフルオリドである、請求項1に記載の方法。
- 前記1価フルオリドカチオンのアルキル基が炭素原子1〜12を有する、請求項5に記載の方法。
- 前記フルオリドのモル数の、化合物(I)中で交換されるハロゲン原子数に対する比が1よりも大きい、請求項1に記載の方法。
- 前記フルオリドのモル数の、化合物(I)中で交換されるハロゲンの原子数に対する比が、1.1〜2である、請求項7に記載の方法。
- 前記フルオリドのモル数の、化合物(I)中で交換されるハロゲンの原子数に対する比が、MがHの場合には、2よりも大きい、請求項7に記載の方法。
- MがH、アルカリ金属、4級アンモニウムであるN(R3R4R5R6)、又は4級ホスホニウムであるP(R3R4R5R6)を表し、ここで各種置換基Riがそれぞれ互いに独立して、1〜12の炭素原子を有するアルキルラジカルから選択される、請求項1に記載の方法。
- 前記カチオンMが1価フルオリドカチオンである、請求項1に記載の方法。
- R1が、ハメットσpパラメーターが0.7より大きい電子吸引性基である、請求項1に記載の方法。
- R 1 がX’SO2−又は(X’)2PO−ラジカルである請求項1に記載の方法。ここでX’は以下のもので表される:
・ハロゲン、
・R7CF2−ラジカル(ここでR7は、F以外のハロゲン又は炭素ラジカル);
・ペルハロゲン化ラジカルRFで、R8(CX”2)p−に相当するが、ここで:
*X”基のそれぞれが、互いに独立して、F、Cl又は1〜5の炭素原子を有するペルフルオロアルキルラジカルであって、X”基の内の少なくとも1つがFであり、pが1又は2を表す;
*R8は電子吸引性原子又はラジカルで、そのσpは0より大きく、それに官能基がある場合には、その官能基は反応条件下で不活性である。 - R7が、最大で15の炭素原子を有する炭素ラジカルである、請求項13に記載の方法。
- 少なくとも1つのX”基が、1〜5の炭素原子を有するペルフルオロアルキルラジカルを表す、請求項13に記載の方法。
- 少なくとも1つのX”基が、硫黄又はリンに結合した炭素によって担持されたF原子である、請求項13に記載の方法。
- R8がF又は、最大で8の炭素原子を有するペルフルオロアルキルラジカルである、請求項13に記載の方法。
- R1が、COOR’、COR’、SO2R’、PO(R’)2又はPR(OR’)2ラジカルを表し、ここでR’が1〜15の炭素原子を有するアルキルラジカル、又は6〜20の炭素原子を有するアリールラジカルである、請求項1に記載の方法。
- 非プロトン性溶媒中で実施される、請求項1に記載の方法。
- 前記溶媒がニトロメタンである、請求項1に記載の方法。
- 置換又は非置換アミド、及び対称又は非対称そして環状又は非環状のエーテルから選択される溶媒中で実施される、請求項1に記載の方法。
- 相間移動触媒が添加される、請求項1に記載の方法。
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FR0017307A FR2818972B1 (fr) | 2000-12-29 | 2000-12-29 | Procede de fluoration d'un compose halogene |
PCT/FR2001/004164 WO2002053494A1 (fr) | 2000-12-29 | 2001-12-21 | Procede de fluoration d'un compose comprenant un groupe halosulfonyle ou dihalophosphonyle |
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JP4198992B2 true JP4198992B2 (ja) | 2008-12-17 |
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US (1) | US7253317B2 (ja) |
EP (1) | EP1347938B1 (ja) |
JP (1) | JP4198992B2 (ja) |
AT (1) | ATE548326T1 (ja) |
CA (1) | CA2432053C (ja) |
ES (1) | ES2382147T3 (ja) |
FR (1) | FR2818972B1 (ja) |
PT (1) | PT1347938E (ja) |
WO (1) | WO2002053494A1 (ja) |
Cited By (1)
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WO2018190304A1 (ja) | 2017-04-10 | 2018-10-18 | セントラル硝子株式会社 | ホスホリルイミド塩の製造方法、該塩を含む非水電解液の製造方法及び非水二次電池の製造方法 |
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Cited By (4)
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WO2018190304A1 (ja) | 2017-04-10 | 2018-10-18 | セントラル硝子株式会社 | ホスホリルイミド塩の製造方法、該塩を含む非水電解液の製造方法及び非水二次電池の製造方法 |
KR20190132509A (ko) | 2017-04-10 | 2019-11-27 | 샌트랄 글래스 컴퍼니 리미티드 | 포스포릴이미드염의 제조방법, 당해 염을 포함하는 비수전해액의 제조방법 및 비수 이차 전지의 제조방법 |
US10851124B2 (en) | 2017-04-10 | 2020-12-01 | Central Glass Co., Ltd. | Method for producing phosphoryl imide salt, method for producing nonaqueous electrolyte solution containing said salt, and method for producing nonaqueous secondary battery |
US11230564B2 (en) | 2017-04-10 | 2022-01-25 | Central Glass Co., Ltd. | Method for producing phosphoryl imide salt, method for producing nonaqueous electrolyte solution containing said salt, and method for producing nonaqueous secondary battery |
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Publication number | Publication date |
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CA2432053C (fr) | 2010-06-15 |
US7253317B2 (en) | 2007-08-07 |
FR2818972B1 (fr) | 2003-03-21 |
ATE548326T1 (de) | 2012-03-15 |
FR2818972A1 (fr) | 2002-07-05 |
EP1347938B1 (fr) | 2012-03-07 |
EP1347938A1 (fr) | 2003-10-01 |
ES2382147T3 (es) | 2012-06-05 |
PT1347938E (pt) | 2012-05-22 |
US20040097757A1 (en) | 2004-05-20 |
JP2004522681A (ja) | 2004-07-29 |
WO2002053494A1 (fr) | 2002-07-11 |
CA2432053A1 (fr) | 2002-07-11 |
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