CN107188138B - A kind of preparation method of double fluorine sulfimide lithiums - Google Patents
A kind of preparation method of double fluorine sulfimide lithiums Download PDFInfo
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- CN107188138B CN107188138B CN201710299616.7A CN201710299616A CN107188138B CN 107188138 B CN107188138 B CN 107188138B CN 201710299616 A CN201710299616 A CN 201710299616A CN 107188138 B CN107188138 B CN 107188138B
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- double fluorine
- fluorine sulfimide
- added
- preparation
- lithium
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- QRMHDYCPNIVCBO-UHFFFAOYSA-N [SH2]=N.[F] Chemical compound [SH2]=N.[F] QRMHDYCPNIVCBO-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 16
- 239000011737 fluorine Substances 0.000 claims abstract description 16
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 15
- 239000007864 aqueous solution Substances 0.000 claims abstract description 14
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 13
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002798 polar solvent Substances 0.000 claims abstract description 12
- 239000011347 resin Substances 0.000 claims abstract description 11
- 229920005989 resin Polymers 0.000 claims abstract description 11
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 11
- 239000012043 crude product Substances 0.000 claims abstract description 10
- 239000000047 product Substances 0.000 claims abstract description 10
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 claims abstract description 10
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims abstract description 9
- 229910052808 lithium carbonate Inorganic materials 0.000 claims abstract description 9
- IDGCBXSROJHVOG-UHFFFAOYSA-N [Li].[SH2]=N.[F] Chemical compound [Li].[SH2]=N.[F] IDGCBXSROJHVOG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000002378 acidificating effect Effects 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZINYQDAIHBZODJ-UHFFFAOYSA-N N=[SH2].N.[F] Chemical class N=[SH2].N.[F] ZINYQDAIHBZODJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 239000003495 polar organic solvent Substances 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims abstract description 5
- 239000011230 binding agent Substances 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 11
- 239000003153 chemical reaction reagent Substances 0.000 claims description 9
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 9
- 238000003682 fluorination reaction Methods 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 8
- -1 fluorine sulfonamide Chemical class 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 claims description 7
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 4
- 239000011698 potassium fluoride Substances 0.000 claims description 4
- 229940090181 propyl acetate Drugs 0.000 claims description 4
- 235000013024 sodium fluoride Nutrition 0.000 claims description 4
- 239000011775 sodium fluoride Substances 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
- ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 claims description 3
- GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 235000003270 potassium fluoride Nutrition 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 2
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 claims description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 241000255964 Pieridae Species 0.000 claims 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- 239000012535 impurity Substances 0.000 abstract description 3
- 229910021645 metal ion Inorganic materials 0.000 abstract description 2
- 230000035484 reaction time Effects 0.000 abstract description 2
- 125000000129 anionic group Chemical group 0.000 abstract 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
- 229910005143 FSO2 Inorganic materials 0.000 description 12
- 238000000034 method Methods 0.000 description 8
- 230000003292 diminished effect Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000004293 19F NMR spectroscopy Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 3
- PWORGPNOUCYYCW-UHFFFAOYSA-N [SH2]=N.[Cl] Chemical class [SH2]=N.[Cl] PWORGPNOUCYYCW-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 229910001416 lithium ion Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229910006024 SO2Cl2 Inorganic materials 0.000 description 2
- VJFJSEPBCMNNGZ-UHFFFAOYSA-N [SH2]=N.[F].[F] Chemical class [SH2]=N.[F].[F] VJFJSEPBCMNNGZ-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- XPVRBHCXMWRJEY-UHFFFAOYSA-N difluoro(imino)-$l^{4}-sulfane Chemical compound FS(F)=N XPVRBHCXMWRJEY-UHFFFAOYSA-N 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- UUBPGZYXFMTMFR-UHFFFAOYSA-N N=[S+]F Chemical compound N=[S+]F UUBPGZYXFMTMFR-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- CQXADFVORZEARL-UHFFFAOYSA-N Rilmenidine Chemical compound C1CC1C(C1CC1)NC1=NCCO1 CQXADFVORZEARL-UHFFFAOYSA-N 0.000 description 1
- XGCDHPDIERKJPT-UHFFFAOYSA-N [F].[S] Chemical compound [F].[S] XGCDHPDIERKJPT-UHFFFAOYSA-N 0.000 description 1
- SHOBVAQMOOFCMB-UHFFFAOYSA-N [K].[SH2]=N.[F] Chemical compound [K].[SH2]=N.[F] SHOBVAQMOOFCMB-UHFFFAOYSA-N 0.000 description 1
- ZJPPTKRSFKBZMD-UHFFFAOYSA-N [Li].FS(=N)F Chemical compound [Li].FS(=N)F ZJPPTKRSFKBZMD-UHFFFAOYSA-N 0.000 description 1
- WFLRGOXPLOZUMC-UHFFFAOYSA-N [Li].O=C=O Chemical compound [Li].O=C=O WFLRGOXPLOZUMC-UHFFFAOYSA-N 0.000 description 1
- RPBVPOXEQVNFAH-UHFFFAOYSA-N [Li].[SH2]=N.[F].[F] Chemical compound [Li].[SH2]=N.[F].[F] RPBVPOXEQVNFAH-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- BRCWHGIUHLWZBK-UHFFFAOYSA-K bismuth;trifluoride Chemical compound F[Bi](F)F BRCWHGIUHLWZBK-UHFFFAOYSA-K 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- ATMIHASMQFJNLZ-UHFFFAOYSA-N dichloro(imino)-$l^{4}-sulfane Chemical compound ClS(Cl)=N ATMIHASMQFJNLZ-UHFFFAOYSA-N 0.000 description 1
- 150000005686 dimethyl carbonates Chemical class 0.000 description 1
- 238000012983 electrochemical energy storage Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 1
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- C01B21/086—Compounds containing nitrogen and non-metals and optionally metals containing one or more sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of preparation methods of double fluorine sulfimide lithiums, comprising the following steps: 1) prepares fluorine sulfonamide lithium；2) vikane is prepared, vikane is passed through in fluorine sulfonamide lithium solution, acid binding agent is added, double fluorine sulfimide ammonium salts are prepared；3) double fluorine sulfimide ammonium salts are dissolved into aqueous solution, exchange to obtain double fluorine sulfimide aqueous solutions by acidic resins；4) lithium carbonate is added, adjusts pH value and is in neutrality, be filtered to remove insoluble matter, most of water is removed under reduced pressure, weakly polar organic solvent is added, double fluorine sulfimide lithium crude products is precipitated, be further dried under reduced pressure；5) into double fluorine sulfimide lithium crude products, polar solvent is added, stirring and dissolving is filtered to remove insoluble matter, and intensive polar solvent is removed under reduced pressure, and weak polar solvent is added and is recrystallized, is dried under reduced pressure to obtain product after filtering.Preparation method of the invention is simple, and the reaction time is short, high income, and can be effectively controlled metal ion and anionic impurity, obtains the product of high-purity.
Description
Technical field
The present invention relates to technical field of compound preparation more particularly to a kind of preparation methods of double fluorine sulfimide lithiums.
Background technique
Fluoro sulfimide and related compound play the role of in materials chemistry and electrochemical energy storage field it is extremely important,
Especially lithium trifluoromethanesulp,onylimide and double fluorine sulfimide lithiums has important industrial application valence in lithium ion battery
Value.Double fluorine sulfimides are the important raw materials for preparing lithium salts and other alkali metal salts and derivative, double fluorine sulfimides one
As by double chlorine sulfimides be fluorinated prepare, the preparation process of double chlorine sulfimides specifically include that 1) phosphorus pentachloride, sulfamic acid and
Chlorosulfonic acid reaction prepares (K.Ruff et al, Inorg.Synth.1968,11,138)；2) sulfamic acid, thionyl chloride and chlorine
Sulfonic acid reaction prepares (M.Beran, Z.Anorg Allg Chem., 2005,631,55).Fluorination reagent mainly have arsenic trifluoride,
Antimony trifluoride, zinc fluoride, anhydrous hydrogen fluoride, bismuth fluoride etc..Double fluorine sulfimide lithium preparation methods have: 1) double fluorine sulfimides
Potassium and other lithium salts exchange systems standby (such as lithium perchlorate and LiBF4) (M.Beran, Polyhedron, 2006,25,
1292)；2) double fluorine sulfimides or ammonium salt and lithium carbonate (or lithium hydroxide) neutralization prepare (CN101980955A,
CN102405189A, CN102917979A, CN104925765A).But there are low yield, ionic impurities to contain for existing method
Measure the defects of high.
Summary of the invention
The purpose of the present invention is to provide a kind of preparation sides of the double fluorine sulfimide lithiums of high-purity needed for lithium ion battery
Method.
In order to solve the above technical problems, the present invention adopts the following technical scheme: a kind of preparation side of double fluorine sulfimide lithiums
Method, specifically includes the following steps:
1) fluorine sulfonamide prepares fluorine sulfonamide lithium in aqueous solution or organic solvent with lithium carbonate effect；
2) chlorosulfuric acid and fluorination reagent reaction prepare vikane, and prepared vikane is passed directly into fluorine sulfonamide lithium solution
In, tertiary amine is added as acid binding agent, double fluorine sulfimide ammonium salts are prepared；
3) double fluorine sulfimide ammonium salt described in step 2) is dissolved into aqueous solution, exchanges to obtain by acidic resins double
Fluorine sulfimide aqueous solution；
4) lithium carbonate is added into double fluorine sulfimide aqueous solutions, adjusts aqueous ph value and is in neutrality, be filtered to remove insoluble
Most of water is removed under reduced pressure in object, weakly polar organic solvent is added, double fluorine sulfimide lithium crude products are precipitated, further decompression is dry
It is dry；
5) in the double fluorine sulfimide lithium crude products of the drying that step 4) is prepared, dry polar solvent is added, stirs
Dissolution, is filtered to remove insoluble matter, and most of intensive polar solvent is removed under reduced pressure, and weak polar solvent is added and carries out recrystallization operation, mistake
It is dried under reduced pressure to obtain product after filter.
Preferably, organic solvent described in step 1) includes acetonitrile, acetone, dimethyl carbonate, diethyl carbonate, carbonic acid first
At least one of ethyl ester, ethyl acetate, propyl acetate, butyl acetate, ether and methyl tertiary butyl ether(MTBE).
Preferably, fluorination reagent described in step 2) include sodium fluoride, potassium fluoride, zinc fluoride, in antimony trifluoride at least
The nonstoichiometric molar ratio of one kind, chlorosulfuric acid and fluorination reagent is 1:2~1:5.
Preferably, the nonstoichiometric molar ratio of the chlorosulfuric acid and fluorination reagent is 1:2.2~1:4, reaction temperature 25
~80 DEG C.
Preferably, tertiary amine described in step 2) include triethylamine, tripropyl amine (TPA), tri-n-butylamine, diisopropyl ethyl amine, pyridine,
At least one of picoline, imidazoles.
Preferably, acidic resins described in step 3) are the highly acidic resin of sulfonic acid type or the weakly acidic resin of carboxylic acid type.
Preferably, weakly polar organic solvent described in step 4) be methylene chloride, chloroform, n-hexane, hexamethylene,
Toluene, dimethylbenzene, chlorobenzene, fluorobenzene.
Preferably, the temperature being dried under reduced pressure described in step 4) is 60~120 DEG C.
Preferably, polar solvent described in step 5) is dimethyl carbonate, diethyl carbonate, methyl ethyl carbonate, acetic acid
Ethyl ester, propyl acetate, butyl acetate, propyl propionate, acetonitrile, propionitrile, acetone, tetrahydrofuran, ether, methyl tertiary butyl ether(MTBE), third
Ether, butyl ether, glycol dimethyl ether.
Preferably, weak polar solvent described in step 5) is methylene chloride, chloroform, n-hexane, hexamethylene, first
Benzene, dimethylbenzene, chlorobenzene, fluorobenzene.
Preparation process provided by the invention is simple, and the reaction time is short, high income, and can be effectively controlled metal ion and yin from
Double fluorine sulfimide lithium target products of high-purity can be prepared in sub- impurity.
Specific embodiment
Illustrate embodiments of the present invention below by way of specific specific example, those skilled in the art can be by this specification
Other advantages and efficacy of the present invention can be easily understood for disclosed content.One or more method and step mentioned in the present invention
Do not repel and is gone back before and after the combination step there may also be other methods step or between these explicitly mentioned steps
Other methods step can be inserted, unless otherwise indicated.
Embodiment 1:
FSO2NH2+Li2CO3→FSO2NHLi
SO2Cl2+KF→SO2F2
FSO2NHLi+SO2F2+Py→FSO2NHSO2F·Py
FSO2NHSO2F+Li2CO3→FSO2NLiSO2F
49.5g (0.5mol) fluorine sulfonamide is added in the reaction flask of 500mL, acetonitrile is added under ice-water bath as solvent, adds
Enter 20.4g (0.275mol) Carbon Dioxide lithium, stirs to neutrality, be filtered under diminished pressure, be dried under reduced pressure after obtaining clear filtrate, obtain fluorine
Sulfonamide lithium crude product.
The reaction flask of 500mL walks prepared fluorine sulfonamide lithium in addition, and the dry acetonitrile of 200mL and 39.5g is added
(0.5mol) pyridine, ice-water bath separately take the reaction flask of a 500mL that 135g (1mol) chlorosulfuric acid, 200mL carbonic acid diethyl is added
Ester, 69.6g (1.2mol) anhydrous potassium fluoride, magnetic agitation, 80 degree of temperature control, reaction flask connects the reflux condensing tube of -20 degree, condensation
The pipe other end is passed through in fluorine sulfonamide lithium/acetonitrile solution, is stopped after reacting 8 hours.It is filtered under diminished pressure to obtain clear filtrate, depressurize
Acetonitrile is removed, double fluorine sulfimide pyridiniujms are obtained.
Double fluorine sulfimide pyridiniujms are dissolved into water, are exchanged by sulfonic acid type acid resin, double fluorine sulfimides are obtained
Lithium carbonate is added in aqueous solution, adjusts pH value as neutrality, is filtered to remove solid, aqueous solution is concentrated under reduced pressure, toluene is added, crystalline substance is precipitated
Body is dried under reduced pressure after filtering.Dry dimethyl carbonate solvent is added, is filtered to remove insoluble matter after dissolution, is removed under reduced pressure big
Dimethyl carbonate is measured, toluene is added and carries out recrystallization operation, obtained solid obtains 65 grams of products after being dried under reduced pressure.(19F-NMR,
51.4；Cl-ND；SO4 2-ND；K<1ppm；Na<5ppm；Mg<1ppm；Ca<1ppm；Fe ND；Hg ND；Cr ND).
Embodiment 2:
FSO2NH2+LiOH→FSO2NHLi
SO2Cl2+NaF→SO2F2
FSO2NHLi+SO2F2+(C2H5)3N→FSO2NHSO2F·Py
FSO2NHSO2F+LiOH→FSO2NLiSO2F
49.5g (0.5mol) fluorine sulfonamide is added in the reaction flask of 500mL, acetonitrile is added under ice-water bath as solvent, adds
Enter 6.6g (0.275mol) lithium hydroxide, stirs to neutrality, be filtered under diminished pressure, be dried under reduced pressure after obtaining clear filtrate, obtain fluorine sulphur
Amide lithium crude product.
The reaction flask of 500mL walks prepared fluorine sulfonamide lithium in addition, and the dry acetonitrile of 200mL and 50.5g is added
(0.5mol) triethylamine, ice-water bath separately take the reaction flask of a 500mL that 135g (1mol) chlorosulfuric acid, 200mL carbonic acid diethyl is added
Ester, 50.4g (1.2mol) anhydrous sodium fluoride, magnetic agitation, 80 degree of temperature control, reaction flask connects the reflux condensing tube of -20 degree, condensation
The pipe other end is passed through in fluorine sulfonamide lithium/acetonitrile solution, is stopped after reacting 8 hours.It is filtered under diminished pressure to obtain clear filtrate, depressurize
Acetonitrile is removed, difluoro sulfimide triethylamine salt is obtained.
Difluoro sulfimide triethylamine salt is dissolved into water, is exchanged by sulfonic acid type acid resin, it is sub- to obtain difluoro sulphonyl
Lithium hydroxide is added in amine aqueous solution, and adjusting pH value is neutrality, is filtered to remove solid, and aqueous solution is concentrated under reduced pressure, and toluene is added and is precipitated
Crystal is dried under reduced pressure after filtering.Dry dimethyl carbonate solvent is added, insoluble matter is filtered to remove after dissolution, is removed under reduced pressure
A large amount of dimethyl carbonates are added toluene and carry out recrystallization operation, and obtained solid obtains 63 grams of products after being dried under reduced pressure.(19F-NMR,
51.6；Cl-ND；SO4 2-ND；K<1ppm；Na<5ppm；Mg<1ppm；Ca<1ppm；Fe ND；Hg ND；Cr ND).
Comparative example 1:
21.9g (0.1mol) double fluorine sulfimide potassium are added in the reaction flask of 500mL, 100mL carbonic acid two is added at room temperature
Methyl esters is added 9.4g (0.1mol) LiBF4, stirs 3 hours, be filtered under diminished pressure, subtract after obtaining clear filtrate as solvent
It press dry dry, obtains the bis- fluorine sulfimide lithium products of 18.2g.(19F-NMR,51.4；Cl-10ppm；SO4 2-20ppm；K 1800ppm；
Na 5ppm；Mg<1ppm；Ca<1ppm；Fe ND；Hg ND；Cr ND).
Comparative example 2:
42.8g (0.2mol) double chlorine sulfimides are added in the reaction flask of 500mL, 24.7g (0.24mol) is added at room temperature
Anhydrous zinc fluoride, after stirring 5 hours, water pump is evaporated under reduced pressure to obtain double fluorine sulfimide crude products, distills and obtains three times repeatedly
The bis- fluorine sulfimides of 27.2g.
The bis- fluorine sulfimides of 27.2g are dissolved into 100mL DMC, be added 15.2g (0.15mol) triethylamine, then plus
Enter 50mL water and 12.6g lithium hydroxide, separate organic phase after stirring 2 hours, double fluorine sulfimide lithiums are obtained after being dried under reduced pressure
Crude product, dimethyl carbonate/toluene Mixed Solvent recrystallization, filtering are dried under reduced pressure to obtain 16.8 grams of double fluorine sulfimide lithiums.19F-NMR,51.5；Cl-12ppm；SO4 2-15ppm；K<2ppm；Na<5ppm；Mg<1ppm；Ca<1ppm；Fe ND；Hg ND；Cr
ND)。
Due to dichloro sulfimide and difluoro sulfimide boiling point it can be seen from embodiment 1,2 and comparative example 1,2 results
Difference is not too greatly, to cause difluoro sulfimide inevitably to mix the chloride ion of more amount, therefore product chlorinity is higher.Comparative example
1 prepares difluoro sulfimide lithium using ion-exchange, since by-product sylvite is difficult sufficiently to go by the method for precipitation/filtration
It removes, causes product potassium content very high, far beyond the specification of lithium-ion battery electrolytes.
The above is a preferred embodiment of the present invention, it is noted that for those skilled in the art
For, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications are also considered as
Protection scope of the present invention.
Claims (10)
1. a kind of preparation method of double fluorine sulfimide lithiums, which comprises the following steps:
1) fluorine sulfonamide prepares fluorine sulfonamide lithium in aqueous solution or organic solvent with lithium carbonate effect；
2) chlorosulfuric acid and fluorination reagent reaction prepare vikane, and prepared vikane is passed directly into fluorine sulfonamide lithium solution,
Tertiary amine is added as acid binding agent, double fluorine sulfimide ammonium salts are prepared；
3) double fluorine sulfimide ammonium salt described in step 2) is dissolved into aqueous solution, exchanges to obtain double fluorine sulphurs by acidic resins
Acid imide aqueous solution；
4) lithium carbonate is added into double fluorine sulfimide aqueous solutions, adjusts aqueous ph value and is in neutrality, be filtered to remove insoluble matter, subtract
Pressure removes most of water, weakly polar organic solvent is added, double fluorine sulfimide lithium crude products are precipitated, be further dried under reduced pressure；
5) in the double fluorine sulfimide lithium crude products of the drying that step 4) is prepared, it is added dry polar solvent, stirring and dissolving,
It is filtered to remove insoluble matter, most of intensive polar solvent is removed under reduced pressure, weak polar solvent is added and carries out recrystallization operation, subtracts after filtering
Pressure is dried to obtain product.
2. the preparation method of double fluorine sulfimide lithiums according to claim 1, it is characterised in that: organic described in step 1)
Solvent includes acetonitrile, acetone, dimethyl carbonate, diethyl carbonate, methyl ethyl carbonate, ethyl acetate, propyl acetate, acetic acid fourth
At least one of ester, ether and methyl tertiary butyl ether(MTBE).
3. the preparation method of double fluorine sulfimide lithiums according to claim 1, it is characterised in that: fluorination described in step 2)
Reagent includes at least one of sodium fluoride, potassium fluoride, zinc fluoride, antimony trifluoride, the stoichiometry of chlorosulfuric acid and fluorination reagent
Molar ratio is 1:2~1:5.
4. the preparation method of double fluorine sulfimide lithiums according to claim 3, it is characterised in that: the chlorosulfuric acid and fluorination
The nonstoichiometric molar ratio of reagent is 1:2.2~1:4, and reaction temperature is 25~80 DEG C.
5. the preparation method of double fluorine sulfimide lithiums according to claim 4, it is characterised in that: tertiary amine described in step 2)
Including at least one of triethylamine, tripropyl amine (TPA), tri-n-butylamine, diisopropyl ethyl amine, pyridine, picoline, imidazoles.
6. the preparation method of double fluorine sulfimide lithiums according to claim 1, it is characterised in that: acidity described in step 3)
Resin is the highly acidic resin of sulfonic acid type or the weakly acidic resin of carboxylic acid type.
7. the preparation method of double fluorine sulfimide lithiums according to claim 1, it is characterised in that: weak described in step 4)
Polar organic solvent is methylene chloride, chloroform, n-hexane, hexamethylene, toluene, dimethylbenzene, chlorobenzene, fluorobenzene.
8. the preparation method of double fluorine sulfimide lithiums according to claim 7, it is characterised in that: depressurized described in step 4)
Dry temperature is 60~120 DEG C.
9. the preparation method of double fluorine sulfimide lithiums according to claim 1, it is characterised in that: pole described in step 5)
Property solvent be dimethyl carbonate, diethyl carbonate, methyl ethyl carbonate, ethyl acetate, propyl acetate, butyl acetate, propyl propionate,
Acetonitrile, propionitrile, acetone, tetrahydrofuran, ether, methyl tertiary butyl ether(MTBE), propyl ether, butyl ether, glycol dimethyl ether.
10. the preparation method of double fluorine sulfimide lithiums according to claim 8, it is characterised in that: described in step 5)
Weak polar solvent is methylene chloride, chloroform, n-hexane, hexamethylene, toluene, dimethylbenzene, chlorobenzene, fluorobenzene.
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| CN107188138B (en) * | 2017-05-02 | 2019-05-14 | 惠州市大道新材料科技有限公司 | A kind of preparation method of double fluorine sulfimide lithiums |
| CN107651654A (en) * | 2017-10-27 | 2018-02-02 | 江苏理文化工有限公司 | A kind of preparation method of double fluorine sulfimide lithiums using villiaumite as fluorization agent |
| EP3761435B1 (en) * | 2018-03-27 | 2022-09-28 | Daikin Industries, Ltd. | Electrolyte solution, electrochemical device, lithium-ion secondary battery, module and compound |
| CN108503670A (en) * | 2018-04-11 | 2018-09-07 | 惠州市大道新材料科技有限公司 | A kind of preparation method of fluorine phosphorimide and its alkali metal salt |
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| CN108946686A (en) * | 2018-07-31 | 2018-12-07 | 九江天赐高新材料有限公司 | A kind of preparation method of double fluorine sulfimide lithiums |
| CN108975292A (en) * | 2018-09-17 | 2018-12-11 | 九江天赐高新材料有限公司 | A kind of preparation method of double fluorine sulfonyl imide compounds |
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| CN115611244B (en) * | 2021-07-14 | 2024-02-02 | 湖南福邦新材料有限公司 | Preparation method of alkali metal salt of dichloro-sulfonyl imide and alkali metal salt of difluoro-sulfonyl imide |
| CN114348978A (en) * | 2022-01-29 | 2022-04-15 | 宁德时代新能源科技股份有限公司 | Lithium bis (fluorosulfonyl) imide, preparation method thereof, electrolyte and secondary battery |
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| CN115448267B (en) * | 2022-09-19 | 2023-04-07 | 安徽新宸新材料有限公司 | Method for preparing lithium bis (fluorosulfonyl) imide |
| CN116283601A (en) * | 2023-03-16 | 2023-06-23 | 浙江中欣氟材股份有限公司 | Preparation method of difluoro sulfonimide organic ammonium salt |
| CN116409761B (en) * | 2023-06-09 | 2023-08-18 | 山东海化集团有限公司 | Preparation method of sodium bis (fluorosulfonyl) imide |
| CN116812876B (en) * | 2023-07-14 | 2024-08-09 | 河南省氟基新材料科技有限公司 | Preparation method of sulfuryl fluoride |
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