CN104230722A - Preparation method of bifluorosulfonyl imide onium salt - Google Patents
Preparation method of bifluorosulfonyl imide onium salt Download PDFInfo
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- CN104230722A CN104230722A CN201410126808.4A CN201410126808A CN104230722A CN 104230722 A CN104230722 A CN 104230722A CN 201410126808 A CN201410126808 A CN 201410126808A CN 104230722 A CN104230722 A CN 104230722A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/037—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements with quaternary ring nitrogen atoms
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
Abstract
The invention relates to a preparation method of bifluorosulfonyl imide onium salt. The preparation method comprises the following step: by adopting hydrogen fluoride as a fluorination reagent and a reaction solvent, reacting with dichlorosulfonyl imide and an onium ion halide to obtain bifluorosulfonyl imide onium salt. Therefore, by adopting the preparation method disclosed by the invention, the raw material cost can be reduced, the material consumption and waste generation can be reduced, the raw material utilization rate and the product yield and purity can be improved, products can be more easily purified, a preparation technological process can be simpler and more efficient, and a good technological base for preparing bifluorosulfonyl imide onium salt massively and industrially can be provided.
Description
Technical field
The present invention relates to a kind of preparation method of fluorochemicals, be specifically related to the preparation method of two fluorine sulfimide salt.
Background technology
Two fluorine sulfimide salt is the important ionic compound of a class, and it is as high-performance electrolyte, plays critical effect in the electrochemistry such as lithium ion battery, ultracapacitor new energy devices, therefore has very high commercial application and is worth.
Tso Tat Co., Ltd., Japan patent CN103391896A, first two chlorine sulfimide is obtained by reacting by Sulfuryl chloride isocyanate and chlorsulfonic acid, then cross after reacting with Neutral ammonium fluoride in acetonitrile and filter solvent and obtain two fluorine sulfimide ammonium salt, finally obtain pair fluorine sulfimide salt with compound generation cationic exchange.The method of this patent report there is reaction and purifying process flow process oversize, impurity not easily with product separation, product yield is too low, raw material consumption too much, the problems such as manufacturing cost is too high.
Nippon Shokubai Co., Ltd patent CN102917979A, first react (or Sulfuryl chloride isocyanate and chlorsulfonic acid react) by sulphonamide and thionyl chloride, chlorsulfonic acid and obtain two chlorine sulfimide, then be obtained by reacting two fluorine sulfimide metal-salt in organic solvent with metal fluoride, last and compound generation cationic exchange obtains two fluorine sulfimide salt.
Above-mentioned known patent all adopts disclosed method to synthesize two chlorine sulfimide (R.Appel et al, Chem.Ber.1962,95,625; M.Goehring et al, Inorg.Synth.1966,8,105; J.Ruff, Inorg.Chem.1967,6,2108; M.Berran et al, Z.Anorg.Allg.Chem.2005,631,55), then prepare and two fluorine sulfonyl imide compounds of purifying, last and compound carries out cationic exchange preparation and purifies obtaining two fluorine sulfimide salt.There is following shortcoming in this method: preparation and purification technical process is oversize, and cause supplies consumption too many, production cost is too high; Foreign ion in cation exchange reaction and ion are difficult to be separated, and cause product yield and purity too low.If above problem is unresolved, will the large-scale application of two fluorine sulfimide salt be hindered, especially hinder it to become main flow electrolyte in the new energy devices such as lithium ion battery, ultracapacitor.
Summary of the invention
In order to overcome the defect of above-mentioned prior art, the object of the present invention is to provide a kind of raw materials cost low and utilization ratio is high, the preparation method of two fluorine sulfimide salt of easy purification of products.
For achieving the above object, the present inventor is by further investigation repeatedly, found that and use hydrogen fluoride as reaction solvent and fluorination reagent, can prepare two fluorine sulfimide salt by two chlorine sulfimide and ionic halide, straight run distillation removing hydrogen fluoride just obtains the very high product of purity.The method shortens existing technical process, decreases supplies consumption and waste discharge, reduces cost of goods manifactured; Because do not have in preparation process introduce be difficult to remove positively charged ion, the therefore easy purifying of product, purity and yield high.The present invention is based on these opinions and complete, the preparation method of a kind of pair of fluorine sulfimide salt provided, comprises the step ionic halide shown in the two chlorine sulfimides shown in structural formula (A), structural formula (B) and hydrogen fluoride reaction being obtained two fluorine sulfimide salt;
Wherein, M
+represent positively charged ion, X
-represent halide-ions.
From technique scheme, the preparation method of of the present invention pair of fluorine sulfimide salt, has the following advantages:
1, using hydrogen fluoride as fluorination reagent and reaction solvent, hydrogen fluoride phase commute obtains and raw materials cost is lower, thus greatly reduces the production cost of product;
2, directly prepare two fluorine sulfimide salt by two chlorine sulfimide, hydrogen fluoride and ionic halide, significantly simplify preparation technology's flow process of product, enhance productivity;
3, reaction product is two fluorine sulfimide salt and hydrogen halide, there is not the byproduct of reaction of other complexity, thus decreases supplies consumption and waste generation, improves the utilization ratio of raw material, product yield and purity;
4, in reaction process, reaction product hydrogen halide with the form Natural excrement of gas, thus can further increase the purity of product; There is no to introduce the positively charged ion being difficult to remove in reaction process, and the hydrogen fluoride unnecessary on a small quantity that may be mingled with in product, also can be removed by conventional technique means such as distillations or be reclaimed, thus make product be easy to purifying, without the need to highly purified practical application standard can be reached by complicated purifying technique, simplify preparation technology's flow process of product, for large-scale industrial production has laid good technical foundation.
Embodiment
By describing technology contents of the present invention, structural attitude in detail, being realized object and effect, be explained in detail below in conjunction with embodiment.
The key distinction point of the present invention and prior art is: adopt hydrogen fluoride react obtained pair fluorine sulfimide salt as fluorination reagent and reaction solvent and two chlorine sulfimide, ionic halide, thus reach reduction raw materials cost, reduce supplies consumption and waste generation, improve raw material availability, product yield and purity, and make the purifying of product easier, preparation technology's flow process is more succinct efficient, for the two fluorine sulfimide salt of extensive industrialization preparation lays good technical foundation.
Concrete, the preparation method of provided by the invention pair of fluorine sulfimide salt, comprises the step ionic halide shown in the two chlorine sulfimides shown in structural formula (A), structural formula (B) and hydrogen fluoride reaction being obtained two fluorine sulfimide salt.
Wherein, M
+represent positively charged ion, X
-represent halide-ions.
In above-mentioned preparation method, described pair of chlorine sulfimide can be commercially available prod, method (R.Appel et al, Chem.Ber.1962,95,625 that also can be recorded by document; M.Goehring et al, Inorg.Synth.1966,8,105; J.Ruff, Inorg.Chem.1967,6,2108; M.Berran et al, Z.Anorg.Allg.Chem.2005,631,55) synthesis obtains.Preferably, described pair of chlorine sulfimide is obtained by sulphonamide, thionyl chloride and chlorsulfonic acid hybrid reaction, and reaction equation is as follows:
Wherein, temperature of reaction controls at 120 ~ 140 DEG C, and the reaction times is 20 ~ 30 hours.Sour gas (the SO produced in reaction process
2, HCl) can lead in alkali lye and absorb, the two chlorine sulfimides obtained after reaction are purified further by underpressure distillation, and the cut temperature of two chlorine sulfimide is 110 ~ 114 DEG C/2mmHg.
Preferably, the mol ratio of described sulphonamide, thionyl chloride and chlorsulfonic acid is acid amides: thionyl chloride: chlorsulfonic acid=1: 2: 1 ~ 1: 4: 1.
In above-mentioned preparation method, described hydrogen fluoride can be commercially available prod, also can be obtained by fluorite Calcium Fluoride (Fluorspan) and strong sulfuric acid response.
In above-mentioned preparation method, described ionic halide can be commercially available prod, also can pass through the method synthesis that document (Electrochim.Acta.2006,51,5567) etc. and the document quoted thereof record and obtain.Wherein, positively charged ion can enumerate ammonium radical ion (NH
4 +), imidazol ion (a), pyridinium ion (b), pyrrolidinium ions (c), piperidines ion (d), morpholinium ion (e), quaternary ammonium ion (f) etc.; Halide-ions comprises fluorion (F
-), chlorion (Cl
-), bromide anion (Br
-) and iodide ion (I
-).Preferably, described positively charged ion is the positively charged ion containing organic radicals R.As organic group, can enumerate saturated or unsaturated alkyl etc., the atom forming it is preferably carbon atom, hydrogen atom, fluorine atom, Sauerstoffatom, nitrogen-atoms or sulphur atom.Saturated or unsaturated alkyl can be the alkyl of straight chain, straight chain or ring-type, and the carbonatoms forming it is preferably 0-18.If positively charged ion keyed jointing R1 and R2 two organic groups, R1 group can be identical with R2 group, also can be different, and also can unite two into one the R group become containing two bonding sites, as follows:
As the positively charged ion containing organic group, can 1 be enumerated, the glyoxaline cations such as 3-dimethyl imidazolium cations, 1-ethyl-3-methylimidazole positively charged ion, 1-propyl group-3-methyl imidazolium cation, 1-butyl-3-methyl imidazolium cation, 1-hexyl-3-methyl imidazolium cation, 1-hexadecyl-3-methyl imidazolium cation, 1-allyl group-3-ethylimidazolium cation, 1,3-diallyl glyoxaline cation; The pyridyliums such as 1-methylpyridinium cations, 1-ethylpyridinium cations, 1-pentyl pyridine positively charged ion, 1-allyl pyridine positively charged ion; The tetramethyleneimine positively charged ion such as 1,1-dimethyl pyrrolidine positively charged ion, 1-methyl isophthalic acid-propyl pyrrole alkane positively charged ion, 1-methyl isophthalic acid-butyl pyrrolidine positively charged ion, 1,1-diethyl tetramethyleneimine positively charged ion, spiral shell two tetramethyleneimine positively charged ion; The tetramethyleneimine positively charged ions such as 1,1-dimethyl piperidinium cations, 1-methyl isophthalic acid-propylpiperdine positively charged ion, spiral shell two pyrrole piperidines positively charged ion; The morpholine positively charged ions such as 4,4-thebaine positively charged ion, 4-methyl-4-propylmorpholin positively charged ion; The quaternary ammonium cations such as tetramethylammonium cation, tetraethylammonium cation, tetrabutyl ammonium cation, triethyl methyl ammonium cation, cyclohexyl-ethyl ammonium cation, diallyl dimethyl ammonium positively charged ion, four (pentafluoroethyl group) ammonium cation.
In above-mentioned preparation method, described pair of chlorine sulfimide, ionic halide and hydrofluoric mol ratio are preferably two chlorine sulfimide: ionic halide: hydrogen fluoride=1: 1: 10 ~ 1: 1: 100.Described hydrogen fluoride exists in liquid form, and described pair of chlorine sulfimide joins (hydrogen fluoride can be contained in dry reaction vessel) in excessive hydrogen fluoride in the mode dripped, and temperature of reaction controls below 20 DEG C, is preferably-15 ~ 15 DEG C.Two chlorine sulfimide can elder generation and hydrogen fluoride reaction, then adds ionic halide reaction, and add two chlorine sulfimide after also hydrogen fluoride and ionic halide first can being mixed again and react, the sour gas that reaction generates can lead in alkali lye and absorb.Reaction times, because of reaction scale difference, is preferably 1 ~ 12 hour.
Further, above-mentioned preparation method also comprises the hydrofluoric step of two fluorine sulfimide salt distillation removal obtained for reaction, and the temperature of distillation is preferably 30 DEG C ~ 60 DEG C.The hydrogen fluoride distilled out can recycle.
Below enumerate embodiment to be described further.
Embodiment 1: the preparation of two fluorine sulfimide
Under stirring, in the 5L reaction vessel of drying, add 679 grams of sulphonamide (7mol) successively, 1785 grams of thionyl chlorides (15mol), and 815.5 grams of chlorsulfonic acids (7mol) obtain mixed solution.Heating mixed solution to 140 DEG C reacts, and the sulfurous gas of generation and hydrochloric acid gas are by alkali liquor absorption.React the brown color liquid crude product obtained after 20 hours and carry out reduced vacuum distillation, collect the cut of 110 ~ 114 DEG C/2mmHg, obtain 1438 grams of two chlorine sulfimide colourless liquids, yield 96%, purity 99%.
Embodiment 1: the preparation of two fluorine sulfimide ammonium salt
Under 5 DEG C of constant temperature stir, add 1600 grams of hydrogen fluoride (80mol) in 3L dry reaction container, slowly add 1284 grams of two chlorine sulfimides (6mol) and carry out chemical reaction, the hydrochloric acid gas of generation is by alkali liquor absorption.Keep 5 DEG C of constant temperature to continue reaction 3 hours after dripping two chlorine sulfimide, obtain the hydrogen fluoride solution of two fluorine sulfimide.In this solution, add 222 grams of Neutral ammonium fluorides (6mol), 5 DEG C of constant temperature stir 2 hours, and ion exchange reaction occurs, and obtain two fluorine sulfimide ammonium salt.After heating Distillation recovery 1300 grams of hydrogen fluoride at 40 DEG C, continue vacuum and heating drying and obtain 1164 grams of two fluorine sulfimide ammonium salts, yield 98%, purity 99%.
Embodiment 2: the preparation of two fluorine sulfimide tetraethyl-ammonium salt
Under 8 DEG C of constant temperature stir, 500 grams of hydrogen fluoride (25mol) are added in 1L dry reaction container, slowly add the two chlorine sulfimides (1mol) of 165.5 grams of etamon chlorides (1mol) and 214 grams and carry out chemical reaction, the hydrochloric acid gas of generation is by alkali liquor absorption.Keep 8 DEG C of constant temperature to continue reaction 5 hours, be then heated to 50 DEG C of Distillation recoveries, 450 grams of hydrogen fluoride, continue vacuum and heating drying and obtain 307 grams of two fluorine sulfimide tetraethyl-ammonium salts, yield 99%, purity 99%.
Embodiment 3: the preparation of two fluorine sulfimide-1,1-dimethyl pyrrolidine salt
Under 10 DEG C of constant temperature stir, 500 grams of hydrogen fluoride (25mol) are added in 1L dry reaction container, slowly add 135.5 grams of chlorinations-1,1-dimethyl pyrrolidine salt (1mol) and 214 grams of two chlorine sulfimides (1mol) carry out chemical reaction, and the hydrochloric acid gas of generation is by alkali liquor absorption.Keep 10 DEG C of constant temperature to continue reaction 3 hours, be then heated to 50 DEG C of Distillation recoveries, 452 grams of hydrogen fluoride, continue vacuum and heating drying and obtain 277 grams of two fluorine sulfimide-1,1-dimethyl pyrrolidine salt, yield 99%, purity 99%.
Embodiment 4: the preparation of two fluorine sulfimide-1-methyl isophthalic acid-propyl-pyrrolidin salt
Under 0 DEG C of constant temperature stirs, 600 grams of hydrogen fluoride (30mol) are added in 1L dry reaction container, slowly add the two chlorine sulfimides (1mol) of 163.5 grams of chlorination-1-methyl isophthalic acids-propyl-pyrrolidin salt (1mol) and 214 grams and carry out chemical reaction, the hydrochloric acid gas of generation is by alkali liquor absorption.Keep 0 DEG C of constant temperature to continue reaction 6 hours, be then heated to 50 DEG C of Distillation recoveries, 550 grams of hydrogen fluoride, continue vacuum and heating drying and obtain 305 grams of two fluorine sulfimide-1-methyl isophthalic acid-propyl-pyrrolidin salt, yield 99%, purity 99%.
Embodiment 5: the preparation of two fluorine sulfimide spiral shell two pyrrolidinium
Under 5 DEG C of constant temperature stir, 600 grams of hydrogen fluoride (30mol) are added in 1L dry reaction container, slowly add the two chlorine sulfimides (1mol) of 161.5 grams of chlorination-1-methyl isophthalic acids-propyl-pyrrolidin salt (1mol) and 214 grams and carry out chemical reaction, the hydrochloric acid gas of generation is by alkali liquor absorption.Keep 5 DEG C of constant temperature to continue reaction 4 hours, be then heated to 50 DEG C of Distillation recoveries, 554 grams of hydrogen fluoride, continue vacuum and heating drying and obtain 303 grams of two fluorine sulfimide spiral shell two pyrrolidiniums, yield 99%, purity 99%.
The foregoing is only embodiments of the invention; not thereby the scope of the claims of the present invention is limited; every utilize description of the present invention to do equivalent structure or equivalent flow process conversion; or be directly or indirectly used in other relevant technical fields, be all in like manner included in scope of patent protection of the present invention.
Claims (9)
1. a preparation method for two fluorine sulfimide salt, is characterized in that: comprise the step ionic halide shown in the two chlorine sulfimides shown in structural formula (A), structural formula (B) and hydrogen fluoride reaction being obtained two fluorine sulfimide salt;
M
+X
- (B)
Wherein, M
+represent positively charged ion, X
-represent halide-ions.
2. the preparation method of according to claim 1 pair of fluorine sulfimide salt, is characterized in that: described positively charged ion is the positively charged ion containing organic group.
3. the preparation method of according to claim 2 pair of fluorine sulfimide salt, is characterized in that: described organic group is the saturated or unsaturated alkyl of straight chain or ring-type, and carbonatoms is 0 ~ 18.
4. the preparation method of according to claim 2 pair of fluorine sulfimide salt, is characterized in that: described positively charged ion is pyridylium, tetramethyleneimine positively charged ion, morpholine positively charged ion or quaternary ammonium cation.
5. the preparation method of the two fluorine sulfimide salt according to Claims 1-4 any one, is characterized in that: described pair of chlorine sulfimide, ionic halide and hydrofluoric mol ratio are two chlorine sulfimide: ionic halide: hydrogen fluoride=1: 1: 10 ~ 1: 1: 100.
6. the preparation method of according to claim 1 pair of fluorine sulfimide salt, is characterized in that: described hydrogen fluoride exists in liquid form, and described pair of chlorine sulfimide joins in excessive hydrogen fluoride in the mode dripped, and temperature of reaction controls below 20 DEG C.
7. the preparation method of according to claim 6 pair of fluorine sulfimide salt, is characterized in that: temperature of reaction is-15 ~ 15 DEG C, and the reaction times is 1 ~ 12 hour.
8. the preparation method of according to claim 1 pair of fluorine sulfimide salt, is characterized in that: also comprise and hydrofluoric step is removed in two fluorine sulfimide salt distillations obtained for reaction.
9. the preparation method of according to claim 8 pair of fluorine sulfimide salt, is characterized in that: described in add thermal distillation temperature be 30 DEG C ~ 60 DEG C.
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| CN201410126808.4A CN104230722A (en) | 2014-03-31 | 2014-03-31 | Preparation method of bifluorosulfonyl imide onium salt |
| PCT/CN2014/089126 WO2015149502A1 (en) | 2014-03-31 | 2014-10-22 | Method for preparing bis(fluorosulfonyl)imide onium salt |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105131000A (en) * | 2015-08-25 | 2015-12-09 | 江苏华盛精化工有限责任公司 | Preparation method of bis(fluoro-sulfonylimines) helical dipyrrolidinium |
| CN105985267A (en) * | 2015-02-05 | 2016-10-05 | 江苏国泰超威新材料有限公司 | Preparation method for ionic liquid applied in electronic industry |
| CN109941978A (en) * | 2019-04-25 | 2019-06-28 | 浙江科峰锂电材料科技有限公司 | The method for preparing double fluorine sulfimide ammoniums and double fluorine sulfimide alkali metal salts |
| CN111630128A (en) * | 2017-11-21 | 2020-09-04 | 日东电工株式会社 | Imidazolium fluorosulfonylimide ionic binder compositions and selective debonding thereof |
Families Citing this family (1)
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| JP6709416B2 (en) * | 2015-11-10 | 2020-06-17 | 日産自動車株式会社 | Ionic conductive solid electrolyte and electrochemical device using the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102046523A (en) * | 2008-07-23 | 2011-05-04 | 第一工业制药株式会社 | Process for producing bis(fluorosulfonyl)imide anion compound, and ion-pair compound |
| CN103391896A (en) * | 2011-03-03 | 2013-11-13 | 日本曹达株式会社 | Manufacturing method for fluorosulfonylimide ammonium salt |
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| CN101980955B (en) * | 2008-03-31 | 2013-07-03 | 株式会社日本触媒 | Sulfonylimide salt and method for producing the same |
| JP5401336B2 (en) * | 2010-01-15 | 2014-01-29 | 株式会社日本触媒 | Method for producing fluorosulfonylimide salt |
| KR101744373B1 (en) * | 2011-02-10 | 2017-06-07 | 닛뽕소다 가부시키가이샤 | Process for production of fluorosulfonylimide ammonium salt |
| JP6147523B2 (en) * | 2013-02-25 | 2017-06-14 | 株式会社日本触媒 | Method for producing fluorosulfonylimide salt |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102046523A (en) * | 2008-07-23 | 2011-05-04 | 第一工业制药株式会社 | Process for producing bis(fluorosulfonyl)imide anion compound, and ion-pair compound |
| CN103391896A (en) * | 2011-03-03 | 2013-11-13 | 日本曹达株式会社 | Manufacturing method for fluorosulfonylimide ammonium salt |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105985267A (en) * | 2015-02-05 | 2016-10-05 | 江苏国泰超威新材料有限公司 | Preparation method for ionic liquid applied in electronic industry |
| CN105131000A (en) * | 2015-08-25 | 2015-12-09 | 江苏华盛精化工有限责任公司 | Preparation method of bis(fluoro-sulfonylimines) helical dipyrrolidinium |
| CN111630128A (en) * | 2017-11-21 | 2020-09-04 | 日东电工株式会社 | Imidazolium fluorosulfonylimide ionic binder compositions and selective debonding thereof |
| CN109941978A (en) * | 2019-04-25 | 2019-06-28 | 浙江科峰锂电材料科技有限公司 | The method for preparing double fluorine sulfimide ammoniums and double fluorine sulfimide alkali metal salts |
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Application publication date: 20141224 |
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| RJ01 | Rejection of invention patent application after publication |