JP4077103B2 - Method for producing tris (perfluoroalkylsulfonyl) methide salt - Google Patents
Method for producing tris (perfluoroalkylsulfonyl) methide salt Download PDFInfo
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- JP4077103B2 JP4077103B2 JP02628699A JP2628699A JP4077103B2 JP 4077103 B2 JP4077103 B2 JP 4077103B2 JP 02628699 A JP02628699 A JP 02628699A JP 2628699 A JP2628699 A JP 2628699A JP 4077103 B2 JP4077103 B2 JP 4077103B2
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- perfluoroalkylsulfonyl
- tris
- methide
- methide salt
- alkali metal
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- 239000007983 Tris buffer Substances 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 125000005525 methide group Chemical class 0.000 title claims 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 15
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- -1 alkali metal cation Chemical class 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical class [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QVXQYMZVJNYDNG-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane Chemical compound [Li+].FC(F)(F)S(=O)(=O)[C-](S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F QVXQYMZVJNYDNG-UHFFFAOYSA-N 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 239000010416 ion conductor Substances 0.000 description 2
- 239000011968 lewis acid catalyst Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- SLVAEVYIJHDKRO-UHFFFAOYSA-N trifluoromethanesulfonyl fluoride Chemical compound FC(F)(F)S(F)(=O)=O SLVAEVYIJHDKRO-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【０００１】
【発明の属する技術分野】
本発明は、ルイス酸触媒および有機イオン電導体として有用な物質である一般式（Ｉ）で示されるトリス（パーフルオロアルキルスルホニル）メチド塩の製造法に関するものである。
【０００２】
【従来の技術】
トリス（パーフルオロアルキルスルホニル）メチド塩は、ルイス酸触媒や有機イオン電導体として有機合成および電気材料分野において有用な物質である。
これまでに提案されているトリス（パーフルオロアルキルスルホニル）メチド塩の製法としては、例えば、
▲１▼下記の如く、メチルマグネシウムハライド（グリニャー試薬）とパーフルオロアルキルスルホニルハライドとの反応によりビス（パーフルオロアルキルスルホニル）メタンを一旦合成した後、再び前記グリニャー試薬およびパーフルオロアルキルスルホニルハライドと反応させてトリス（パーフルオロアルキルスルホニル）メタンを合成し、更にアルカリ金属化合物と反応させる方法（ＷＯ92／02966,Inorg.Chem., 1988,27,2135.,J.Chem.Soc.Faraday Trans.,1993,89,355 等）
3CH3MgX + 2RfSO2X + HX → (RfSO2)2CH2 + 2CH4 + 3MgX2
(RfSO2)2CH2 + 2CH3MgX + RfSO2X + HX
→ (RfSO2)3CH + 2CH4 + 2MgX2
(RfSO2)3CH + MOR → (RfSO2)3CM + ROH
［式中、X はハロゲン、 Rf はパーフルオロアルキル基、M はアルカリ金属陽イオン、R は水素またはメチル基を表す。］
▲２▼上記ビス（パーフルオロアルキルスルホニル）メタンをアルカリ金属塩に変換した後、塩基存在下でフルオロアルキルスルホニルハライドと反応してトリス（パーフルオロアルキルスルホニル）メタン化合物を合成し、さらにアルカリ金属化合物と反応させる方法（ＵＳＰ5446134 等）
(RfSO2)2CH2 + MOR → (RfSO2)2CHM + ROH
(RfSO2)2CHM + RfSO2X + Et3N → (RfSO2)3CHNEt3 + MX
(RfSO2)3CHNEt3 + M2PO4 → (RfSO2)3CM + M(Et3NH)PO4
［式中、 Rf, M, R, X は前記定義の通りである。］
等が知られている。
しかしながら、上記▲１▼および▲２▼の方法は、いずれも非常に多くの工程を必要とする上に高価なグリニャー試薬を多量に使用することから、工業的な製法ではない。
以上のように、トリス（パーフルオロアルキルスルホニル）メチド塩の実用的な合成法については、満足のいく方法が見当たらないのが実情である。
【０００３】
【発明が解決しようとする課題】
従って本発明の目的は、上記▲１▼および▲２▼の方法による問題点を解決し、トリス（パーフルオロアルキルスルホニル）メチド塩の簡便な工業的製法を提供するものである。
【０００４】
【課題を解決するための手段】
本発明者らは、上記目的を達成するため鋭意検討した結果、メチド化剤としてアルカリ金属メタンを用いることによりトリス（パーフルオロアルキルスルホニル）メチド塩の簡便な製造法を見い出した。
本発明によれば、パーフルオロアルキルスルホニルハライドとアルカリ金属メタンからなる混合物を有機溶媒中で反応させることにより、一工程でトリス（パーフルオロアルキルスルホニル）メチド塩を製造することができる。
即ち、本発明は、
一般式（II）：
RfSO2X …（II）
〔式中、X はハロゲンを表す。 Rf は炭素数１から６までの直鎖または分岐状のパーフルオロアルキル基を表す。〕
で示されるパーフルオロアルキルスルホニルハライドと、
一般式（III）：
MCH3 …（III）
〔式中、M はアルカリ金属陽イオンを表す。〕
で示されるアルカリ金属メタンからなる混合物を有機溶媒中で反応させることにより、
一般式（Ｉ）：
(RfSO2)3CM …（Ｉ）
〔式中、 Rf およびM は前記定義の通りである。〕
で表されるトリス（パーフルオロアルキルスルホニル）メチド塩を製造する方法である。
【０００５】
【発明の実施の形態】
以下、本発明を詳細に説明する。
本発明において化合物（Ｉ）の製造に用いられる有機溶媒としては、（II）および（III）が可溶で、反応工程中で原料及び生成物と反応しない不活性溶媒が好ましく、例えば、ジエチルエーテル、テトラヒドロフラン、ジオキサン等のエーテル類が好適なものとして挙げられるが、これらに限定されるものではない。上記反応は−70℃から 150℃の温度範囲で行うことが可能であり、最適には、30℃から 100℃の温度範囲が好ましい。
【０００６】
本発明の反応式は、次のように示される。
3RfSO2X + 4MCH3 → (RfSO2)3CM + 3LiX + 3CH3
［式中、 Rf は炭素数１から６までの直鎖または分岐状のパーフルオロアルキル基であり、好ましくはCF3 、C2F5、C3F7、C4F9である。X はハロゲン、M はアルカリ金属陽イオンであり、好ましくはLi+ 、Na+ 、K + である。］
上記 Rf としてはCF3 、C2F5、C3F7、C4F9が好ましく、またM としてはLi+ 、Na+ 、K + が好ましい。
【０００７】
【実施例】
以下に実施例により本発明を更に詳細に説明するが、本発明はこれらの実施例に限定されるものではない。
実施例１［リチウムトリス（トリフルオロメタンスルホニル）メチドの製造］
コンデンサーを付した500mL 三口フラスコを窒素置換した後、1.4Mメチルリチウム／エーテル溶液300mL を仕込み、ドライアイス／エタノール浴上−55℃に冷却した。激しく攪拌しながら、トリフルオロメタンスルホニルクロライド53ｇを滴下した。その後、徐々に昇温し、沸騰還流下で７時間反応を行なった。
室温まで放冷した後、冷却しながら５％塩酸を加え十分攪拌を行なった。晶析した塩化リチウムおよび水酸化リチウムを濾別した。
濾液は、エーテルで抽出した後、飽和食塩水で洗浄した。有機層は、無水硫酸マグネシウムを加え１時間乾燥した後、孔径 0.2μm のメンブランフィルター（日本ミリポール社製）により減圧濾過した。濾液は、減圧下溶媒を留去した後、トルエンを加えて共沸脱水を行った。得られた結晶を 150℃で72時間乾燥を行った結果、リチウムトリス（トリフルオロメタンスルホニル）メチド：(CF3SO2)3CLi 13.5g（収率31％）を得た。
得られた物質の物性値は以下の通りであった。
融点： 268℃
13Ｃ−ＮＭＲ（CD3CN ，δ）：123.3, 119.1
19Ｆ−ＮＭＲ（CD3CN ，δ）：−77.5(S)
ＩＲ（ｋＢｒ，cm-1）：3500, 1645, 1377, 1202, 1124, 983, 769, 668, 625, , 576, 506, 445, 417, 406
実施例２
200mL ステンレス製オートクレーブを窒素置換した後、1.4Mメチルリチウム／エーテル溶液 100mLを仕込み、ドライアイス／エタノール浴上−75℃に冷却した。これにトリフルオロメタンスルホニルクロライド20ｇを添加した。その後徐々に昇温し、90℃、8.5 kg／cm2 で24時間反応を行なった。
実施例１と同様の処理を行なった結果、リチウムトリス（トリフルオロメタンスルホニル）メチド 8.1ｇ（収率56％）を得た。
実施例３
トリフルオロメタンスルホニルフルオライドを使用し、実施例２と同様の条件で反応を行なった結果、リチウムトリス（トリフルオロメタンスルホニル）メチドを得た。収率は、42％であった。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a method for producing a tris (perfluoroalkylsulfonyl) methide salt represented by the general formula (I) which is a substance useful as a Lewis acid catalyst and an organic ion conductor.
[0002]
[Prior art]
Tris (perfluoroalkylsulfonyl) methide salt is a useful substance in the field of organic synthesis and electrical materials as a Lewis acid catalyst and an organic ion conductor.
As a method for producing a tris (perfluoroalkylsulfonyl) methide salt proposed so far, for example,
(1) As described below, bis (perfluoroalkylsulfonyl) methane is once synthesized by reaction of methylmagnesium halide (Grigner reagent) and perfluoroalkylsulfonyl halide, and then reacted again with the Grignard reagent and perfluoroalkylsulfonyl halide. And tris (perfluoroalkylsulfonyl) methane to be synthesized and further reacted with an alkali metal compound (WO92 / 02966, Inorg. Chem., 1988, 27, 2135., J. Chem. Soc. Faraday Trans., 1993) , 89,355 etc.)
3CH 3 MgX + 2R f SO 2 X + HX → (R f SO 2 ) 2 CH 2 + 2CH 4 + 3MgX 2
(R f SO 2 ) 2 CH 2 + 2CH 3 MgX + R f SO 2 X + HX
→ (R f SO 2 ) 3 CH + 2CH 4 + 2MgX 2
(R f SO 2 ) 3 CH + MOR → (R f SO 2 ) 3 CM + ROH
[Wherein, X represents halogen, R f represents a perfluoroalkyl group, M represents an alkali metal cation, and R represents hydrogen or a methyl group. ]
(2) The above bis (perfluoroalkylsulfonyl) methane is converted to an alkali metal salt and then reacted with a fluoroalkylsulfonyl halide in the presence of a base to synthesize a tris (perfluoroalkylsulfonyl) methane compound. (USP 5446134 etc.)
(R f SO 2 ) 2 CH 2 + MOR → (R f SO 2 ) 2 CHM + ROH
(R f SO 2 ) 2 CHM + R f SO 2 X + Et 3 N → (R f SO 2 ) 3 CHNEt 3 + MX
(R f SO 2 ) 3 CHNEt 3 + M 2 PO 4 → (R f SO 2 ) 3 CM + M (Et 3 NH) PO 4
[Wherein R f , M, R and X are as defined above. ]
Etc. are known.
However, the methods {circle around (1)} and {circle around (2)} are not industrial production methods because they require a large number of steps and a large amount of expensive Grignard reagent is used.
As described above, there is no satisfactory method for practical synthesis of tris (perfluoroalkylsulfonyl) methide salt.
[0003]
[Problems to be solved by the invention]
Accordingly, an object of the present invention is to solve the problems caused by the methods (1) and (2) and to provide a simple industrial process for producing a tris (perfluoroalkylsulfonyl) methide salt.
[0004]
[Means for Solving the Problems]
As a result of intensive studies to achieve the above object, the present inventors have found a simple method for producing a tris (perfluoroalkylsulfonyl) methide salt by using alkali metal methane as a methidizing agent.
According to the present invention, a tris (perfluoroalkylsulfonyl) methide salt can be produced in one step by reacting a mixture of perfluoroalkylsulfonyl halide and alkali metal methane in an organic solvent.
That is, the present invention
General formula (II):
R f SO 2 X (II)
[Wherein X represents halogen. R f represents a linear or branched perfluoroalkyl group having 1 to 6 carbon atoms. ]
A perfluoroalkylsulfonyl halide represented by
General formula (III):
MCH 3 (III)
[Wherein M represents an alkali metal cation. ]
By reacting a mixture of alkali metal methane represented by
Formula (I):
(R f SO 2 ) 3 CM (I)
[Wherein R f and M are as defined above. ]
A tris (perfluoroalkylsulfonyl) methide salt represented by the formula:
[0005]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the present invention will be described in detail.
As the organic solvent used in the production of the compound (I) in the present invention, an inert solvent in which (II) and (III) are soluble and does not react with the raw materials and products in the reaction step is preferable. For example, diethyl ether Ethers such as tetrahydrofuran, dioxane and the like are preferable, but not limited thereto. The above reaction can be carried out in a temperature range of −70 ° C. to 150 ° C., and most preferably, a temperature range of 30 ° C. to 100 ° C. is preferable.
[0006]
The reaction formula of the present invention is shown as follows.
3R f SO 2 X + 4MCH 3 → (R f SO 2 ) 3 CM + 3LiX + 3CH 3
[Wherein, R f is a linear or branched perfluoroalkyl group having 1 to 6 carbon atoms, preferably CF 3 , C 2 F 5 , C 3 F 7 , C 4 F 9] . X is a halogen, M is an alkali metal cation, and preferably Li + , Na + , K + . ]
The preferred CF 3, C 2 F 5, C 3 F 7, C 4 F 9 as R f, and as the M Li +, Na +, K + is preferred.
[0007]
【Example】
EXAMPLES The present invention will be described in more detail with reference to examples below, but the present invention is not limited to these examples.
Example 1 [Production of lithium tris (trifluoromethanesulfonyl) methide]
A 500 mL three-necked flask equipped with a condenser was purged with nitrogen, and then charged with 300 mL of a 1.4 M methyllithium / ether solution, and cooled to −55 ° C. on a dry ice / ethanol bath. With vigorous stirring, 53 g of trifluoromethanesulfonyl chloride was added dropwise. Thereafter, the temperature was gradually raised, and the reaction was carried out under boiling reflux for 7 hours.
After allowing to cool to room temperature, 5% hydrochloric acid was added while cooling and the mixture was sufficiently stirred. Crystallized lithium chloride and lithium hydroxide were filtered off.
The filtrate was extracted with ether and washed with saturated brine. The organic layer was dried over 1 hour by adding anhydrous magnesium sulfate, and then filtered under reduced pressure through a membrane filter (manufactured by Nihon Millipole) having a pore size of 0.2 μm. After the solvent was distilled off under reduced pressure, the filtrate was subjected to azeotropic dehydration by adding toluene. The obtained crystals were dried at 150 ° C. for 72 hours. As a result, 13.5 g (yield 31%) of lithium tris (trifluoromethanesulfonyl) methide: (CF 3 SO 2 ) 3 CLi was obtained.
The physical properties of the obtained substance were as follows.
Melting point: 268 ° C
13 C-NMR (CD 3 CN, δ): 123.3, 119.1
19 F-NMR (CD 3 CN, δ): −77.5 (S)
IR (kBr, cm −1 ): 3500, 1645, 1377, 1202, 1124, 983, 769, 668, 625,, 576, 506, 445, 417, 406
Example 2
A 200 mL stainless steel autoclave was purged with nitrogen, and then 100 mL of a 1.4 M methyllithium / ether solution was charged and cooled to −75 ° C. on a dry ice / ethanol bath. To this was added 20 g of trifluoromethanesulfonyl chloride. Thereafter, the temperature was gradually raised, and the reaction was carried out at 90 ° C. and 8.5 kg / cm 2 for 24 hours.
As a result of carrying out the same treatment as in Example 1, 8.1 g (yield 56%) of lithium tris (trifluoromethanesulfonyl) methide was obtained.
Example 3
As a result of carrying out the reaction under the same conditions as in Example 2 using trifluoromethanesulfonyl fluoride, lithium tris (trifluoromethanesulfonyl) methide was obtained. The yield was 42%.
Claims (1)
(RfSO2)3CM …（Ｉ）
〔式中、 Rf は炭素数１から６までの直鎖または分岐状のパーフルオロアルキル基、M はアルカリ金属陽イオンを表す。〕
で表されるトリス（パーフルオロアルキルスルホニル）メチド塩の製造法であって、
一般式（II）：
RfSO2X …（II）
〔式中、X はハロゲンを表す。 Rf は前記定義の通りである。〕
で示されるパーフルオロアルキルスルホニルハライドと、
一般式（III）：
MCH3 …（III）
〔式中、M は前記定義の通りである。〕
で示されるアルカリ金属メタンからなる混合物を有機溶媒中で反応させることを特徴とするトリス（パーフルオロアルキルスルホニル）メチド塩の製造方法。Formula (I):
(R f SO 2 ) 3 CM (I)
[Wherein, R f represents a linear or branched perfluoroalkyl group having 1 to 6 carbon atoms, and M represents an alkali metal cation. ]
A process for producing a tris (perfluoroalkylsulfonyl) methide salt represented by:
General formula (II):
R f SO 2 X (II)
[Wherein X represents halogen. R f is as defined above. ]
A perfluoroalkylsulfonyl halide represented by
General formula (III):
MCH 3 (III)
[Wherein M is as defined above. ]
A method for producing a tris (perfluoroalkylsulfonyl) methide salt, which comprises reacting a mixture of alkali metal methane represented by formula (1) in an organic solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP02628699A JP4077103B2 (en) | 1999-02-03 | 1999-02-03 | Method for producing tris (perfluoroalkylsulfonyl) methide salt |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP02628699A JP4077103B2 (en) | 1999-02-03 | 1999-02-03 | Method for producing tris (perfluoroalkylsulfonyl) methide salt |
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| Publication Number | Publication Date |
|---|---|
| JP2000226392A JP2000226392A (en) | 2000-08-15 |
| JP4077103B2 true JP4077103B2 (en) | 2008-04-16 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP02628699A Expired - Lifetime JP4077103B2 (en) | 1999-02-03 | 1999-02-03 | Method for producing tris (perfluoroalkylsulfonyl) methide salt |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5186910B2 (en) | 2006-12-20 | 2013-04-24 | セントラル硝子株式会社 | Method for producing tris (perfluoroalkanesulfonyl) methidoate |
| CN115557862A (en) * | 2022-10-25 | 2023-01-03 | 广州天赐高新材料股份有限公司 | Preparation method of tris (perfluoroalkyl sulfonyl) methane and lithium salt thereof |
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