CN107188138A - A kind of preparation method of pair of fluorine sulfimide lithium - Google Patents
A kind of preparation method of pair of fluorine sulfimide lithium Download PDFInfo
- Publication number
- CN107188138A CN107188138A CN201710299616.7A CN201710299616A CN107188138A CN 107188138 A CN107188138 A CN 107188138A CN 201710299616 A CN201710299616 A CN 201710299616A CN 107188138 A CN107188138 A CN 107188138A
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- CN
- China
- Prior art keywords
- lithium
- fluorine sulfimide
- preparation
- fluorine
- pair
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- IDGCBXSROJHVOG-UHFFFAOYSA-N [Li].[SH2]=N.[F] Chemical compound [Li].[SH2]=N.[F] IDGCBXSROJHVOG-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- QRMHDYCPNIVCBO-UHFFFAOYSA-N [SH2]=N.[F] Chemical compound [SH2]=N.[F] QRMHDYCPNIVCBO-UHFFFAOYSA-N 0.000 claims abstract description 18
- 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
- 239000002798 polar solvent 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
- 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
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 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
- 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
- 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
- 239000000243 solution Substances 0.000 claims abstract description 5
- 239000011230 binding agent Substances 0.000 claims abstract description 3
- 239000003495 polar organic solvent 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 21
- 238000006243 chemical reaction Methods 0.000 claims description 18
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 17
- 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
- -1 fluorine sulfonamide Chemical class 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
- 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
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 claims description 7
- 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
- 239000002904 solvent Substances 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
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 4
- 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
- 230000000694 effects Effects 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
- 239000003960 organic solvent Substances 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
- 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
- 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
- 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
- 150000002148 esters Chemical class 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 14
- 229910005143 FSO2 Inorganic materials 0.000 description 12
- 238000000034 method Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 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
- 239000007787 solid Substances 0.000 description 4
- 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
- 238000005516 engineering process Methods 0.000 description 3
- 229910001416 lithium ion Inorganic materials 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
- 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
- 239000000463 material Substances 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
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000370738 Chlorion Species 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 241000165940 Houjia Species 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
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001408 amides 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
- 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
- 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
- 230000001846 repelling effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 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 the preparation method of a kind of pair of fluorine sulfimide lithium, comprise the following steps：1) fluorine sulfonamide lithium is prepared；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 the aqueous solution, are exchanged by acidic resins and obtain double fluorine sulfimide aqueous solution；4) lithium carbonate is added, regulation pH value is filtered to remove insoluble matter in neutrality, and most of water is removed under reduced pressure, adds weakly polar organic solvent and separate out double fluorine sulfimide lithium crude products, 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, intensive polar solvent is removed under reduced pressure, added weak polar solvent and recrystallized, be dried under reduced pressure after filtering and obtain product.The preparation method of the present invention is simple, and the reaction time is short, high income, and can effectively control metal ion and anionic impurity, obtains the product of high-purity.
Description
Technical field
The present invention relates to the preparation method of technical field of compound preparation, more particularly to a kind of pair of fluorine sulfimide lithium.
Background technology
Fluoro sulfimide and related compound play extremely important effect in materials chemistry and electrochemical energy storage field,
Especially lithium trifluoromethanesulp,onylimide and double fluorine sulfimide lithiums has important commercial application valency in lithium ion battery
Value.Double fluorine sulfimides are the important raw and processed materials for preparing lithium salts and other alkali metal salts and derivative, double fluorine sulfimides one
As be fluorinated and prepare by double chlorine sulfimides, the preparation technology of double chlorine sulfimides mainly includes：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 sulfimide or ammonium salt and lithium carbonate (or lithium hydroxide) neutralizations prepare (CN101980955A,
CN102405189A, CN102917979A, CN104925765A).But, there is low yield, ionic impurity and contain in existing method
Measure high defect.
The content of the invention
It is an object of the invention to provide a kind of preparation side of the double fluorine sulfimide lithiums of the high-purity needed for lithium ion battery
Method.
To solve above technical problem, the present invention is adopted the following technical scheme that：A kind of preparation side of pair of fluorine sulfimide lithium
Method, specifically includes following steps：
1) fluorine sulfonamide prepares fluorine sulfonamide lithium in the 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, prepares double fluorine sulfimide ammonium salts；
3) by step 2) described in double fluorine sulfimide ammonium salts be dissolved into the aqueous solution, exchanged by acidic resins and obtain double
The fluorine sulfimide aqueous solution；
4) lithium carbonate is added into double fluorine sulfimide aqueous solution, regulation aqueous ph value is filtered to remove insoluble in neutrality
Thing, is removed under reduced pressure most of water, adds weakly polar organic solvent and separates out double fluorine sulfimide lithium crude products, further decompression is dry
It is dry；
5) step 4) in the double fluorine sulfimide lithium crude products of the drying for preparing, add dry polar solvent, stirring
Dissolving, is filtered to remove insoluble matter, and most of intensive polar solvent is removed under reduced pressure, and adds weak polar solvent and carries out recrystallization operation, mistake
It is dried under reduced pressure after filter and obtains product.
It is preferred that, step 1) described in organic solvent include 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).
It is preferred that, step 2) described in fluorination reagent include sodium fluoride, potassium fluoride, zinc fluoride, antimony trifluoride at least
The nonstoichiometric molar ratio of one kind, chlorosulfuric acid and fluorination reagent is 1：2~1：5.
It is preferred that, the nonstoichiometric molar ratio of the chlorosulfuric acid and fluorination reagent is 1：2.2~1：4, reaction temperature is 25
~80 DEG C.
It is preferred that, step 2) described in tertiary amine include triethylamine, tripropyl amine (TPA), tri-n-butylamine, diisopropyl ethyl amine, pyridine,
At least one of picoline, imidazoles.
It is preferred that, step 3) described in acidic resins for sulfonic acid type highly acidic resin or carboxylic acid type weakly acidic resin.
It is preferred that, step 4) described in weak polar solvent be dichloromethane, chloroform, n-hexane, hexamethylene, first
Benzene, dimethylbenzene, chlorobenzene, fluorobenzene.
It is preferred that, step 4) described in the temperature that is dried under reduced pressure be 60~120 DEG C.
It is preferred that, step 5) described in polar solvent be 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.
It is preferred that, step 5) described in weak polar solvent be dichloromethane, chloroform, n-hexane, hexamethylene, first
Benzene, dimethylbenzene, chlorobenzene, fluorobenzene.
Preparation technology that the present invention is provided is simple, and the reaction time is short, high income, and can effectively control metal ion and it is cloudy from
Sub- impurity, can prepare double fluorine sulfimide lithium target products of high-purity.
Embodiment
Illustrate embodiments of the present invention below by way of specific instantiation, those skilled in the art can be by this specification
Disclosed content understands other advantages and effect of the present invention easily.The one or more method and steps mentioned in the present invention
Other method step can also be present or be gone back between the step of these are specifically mentioned by not repelling before and after the combination step
Other method step is may be inserted into, unless otherwise indicated.
Embodiment 1：
FSO2NH2+Li2CO3→FSO2NHLi
SO2Cl2+KF→SO2F2
FSO2NHLi+SO2F2+Py→FSO2NHSO2F·Py
FSO2NHSO2F+Li2CO3→FSO2NLiSO2F
Added in 500mL reaction bulb and acetonitrile is added under 49.5g (0.5mol) fluorine sulfonamide, ice-water bath as solvent, plus
Enter 20.4g (0.275mol) Carbon Dioxide lithium, stir to neutrality, be filtered under diminished pressure, obtain being dried under reduced pressure after clear filtrate, obtain fluorine
Sulfonamide lithium crude product.
Prepared fluorine sulfonamide lithium is walked in 500mL reaction bulb, addition, 200mL is added and dries acetonitrile and 39.5g
(0.5mol) pyridine, ice-water bath separately takes 500mL reaction bulb to add 135g (1mol) chlorosulfuric acid, 200mL carbonic acid diethyls
Ester, 69.6g (1.2mol) anhydrous potassium fluoride, magnetic agitation, 80 degree of temperature control, reaction bulb 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 8 hours of reaction.It is filtered under diminished pressure and obtains clear filtrate, depressurizes
Acetonitrile is removed, double fluorine sulfimide pyridiniujms are obtained.
Double fluorine sulfimide pyridiniujms are dissolved into water, exchanged by sulfonic acid type acid resin, double fluorine sulfimides are obtained
The aqueous solution, adds lithium carbonate, and regulation pH value is neutrality, is filtered to remove solid, be concentrated under reduced pressure the aqueous solution, and addition toluene separates out brilliant
It is dried under reduced pressure after body, filtering.Insoluble matter is filtered to remove after adding dry dimethyl carbonate solvent, dissolving, is removed under reduced pressure big
Dimethyl carbonate is measured, toluene is added and carries out recrystallization operation, gained 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
Added in 500mL reaction bulb and acetonitrile is added under 49.5g (0.5mol) fluorine sulfonamide, ice-water bath as solvent, plus
Enter 6.6g (0.275mol) lithium hydroxide, stir to neutrality, be filtered under diminished pressure, obtain being dried under reduced pressure after clear filtrate, obtain fluorine sulphur
Acid amides lithium crude product.
Prepared fluorine sulfonamide lithium is walked in 500mL reaction bulb, addition, 200mL is added and dries acetonitrile and 50.5g
(0.5mol) triethylamine, ice-water bath separately takes 500mL reaction bulb to add 135g (1mol) chlorosulfuric acid, 200mL carbonic acid diethyls
Ester, 50.4g (1.2mol) anhydrous sodium fluoride, magnetic agitation, 80 degree of temperature control, reaction bulb 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 8 hours of reaction.It is filtered under diminished pressure and obtains clear filtrate, depressurizes
Acetonitrile is removed, difluoro sulfimide triethylamine salt is obtained.
Difluoro sulfimide triethylamine salt is dissolved into water, exchanged by sulfonic acid type acid resin, difluoro sulphonyl is obtained sub-
Amine aqueous solution, adds lithium hydroxide, and regulation pH value is neutrality, is filtered to remove solid, be concentrated under reduced pressure the aqueous solution, adds toluene and separates out
It is dried under reduced pressure after crystal, filtering.Insoluble matter is filtered to remove after adding dry dimethyl carbonate solvent, dissolving, is removed under reduced pressure
A large amount of dimethyl carbonates, add toluene and carry out recrystallization operation, gained 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 500mL reaction bulb, 100mL carbonic acid two is added at room temperature
Methyl esters adds 9.4g (0.1mol) LiBF4 as solvent, stirs 3 hours, is filtered under diminished pressure, obtains subtracting after clear filtrate
Press dry dry, obtain the double 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 500mL reaction bulb, 24.7g (0.24mol) is added at room temperature
Anhydrous zinc fluoride, after 5 hours of stirring, water pump vacuum distillation obtains double fluorine sulfimide crude products, distills three times and obtains repeatedly
The double fluorine sulfimides of 27.2g.
The double fluorine sulfimides of 27.2g are dissolved into 100mL DMC, 15.2g (0.15mol) triethylamine, Ran Houjia is added
Enter 50mL water and 12.6g lithium hydroxides, organic phase is separated after 2 hours of stirring, double fluorine sulfimide lithiums are obtained after being dried under reduced pressure
Crude product, dimethyl carbonate/toluene Mixed Solvent recrystallization, filtering is dried under reduced pressure and obtains 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 big, causes difluoro sulfimide to mix the chlorion of more amount unavoidably, therefore product chlorinity is higher.Comparative example
1 prepares difluoro sulfimide lithium using ion-exchange, because accessory substance sylvite is difficult fully to be gone by the method for precipitation/filtration
Remove, cause product potassium content very high, far beyond the specification of lithium-ion battery electrolytes.
Described above is the preferred embodiment of the present invention, it is noted that for those skilled in the art
For, under the premise without departing from the principles of the invention, some improvements and modifications can also be made, these improvements and modifications are also considered as
Protection scope of the present invention.
Claims (10)
1. the preparation method of a kind of pair of fluorine sulfimide lithium, it is characterised in that comprise the following steps：
1) fluorine sulfonamide prepares fluorine sulfonamide lithium in the 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) by step 2) described in double fluorine sulfimide ammonium salts be dissolved into the aqueous solution, exchanged by acidic resins and obtain double fluorine sulphurs
The acid imide aqueous solution；
4) lithium carbonate is added into double fluorine sulfimide aqueous solution, regulation aqueous ph value is filtered to remove insoluble matter, subtracted in neutrality
Pressure removes most of water, adds weakly polar organic solvent and separates out double fluorine sulfimide lithium crude products, is further dried under reduced pressure；
5) step 4) in the double fluorine sulfimide lithium crude products of the drying for preparing, add dry polar solvent, stirring and dissolving,
Insoluble matter is filtered to remove, most of intensive polar solvent is removed under reduced pressure, weak polar solvent is added and carries out recrystallization operation, subtract after filtering
Pressure is dried to obtain product.
2. the preparation method of according to claim 1 pair of fluorine sulfimide lithium, it is characterised in that：Step 1) described in it is organic
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 according to claim 1 pair of fluorine sulfimide lithium, it is characterised in that：Step 2) described in fluorination
Reagent includes at least one of sodium fluoride, potassium fluoride, zinc fluoride, antimony trifluoride, the stoichiometry of chlorosulfuric acid and fluorination reagent
Mol ratio is 1：2~1：5.
4. the preparation method of according to claim 3 pair of fluorine sulfimide lithium, it is characterised in that：The chlorosulfuric acid and fluorination
The nonstoichiometric molar ratio of reagent is 1：2.2~1：4, reaction temperature is 25~80 DEG C.
5. the preparation method of according to claim 4 pair of fluorine sulfimide lithium, it is characterised in that：Step 2) described in tertiary amine
Including at least one of triethylamine, tripropyl amine (TPA), tri-n-butylamine, diisopropyl ethyl amine, pyridine, picoline, imidazoles.
6. the preparation method of according to claim 1 pair of fluorine sulfimide lithium, it is characterised in that：Step 3) described in acidity
Resin is the highly acidic resin of sulfonic acid type or the weakly acidic resin of carboxylic acid type.
7. the preparation method of according to claim 1 pair of fluorine sulfimide lithium, it is characterised in that：Step 4) described in it is weak
Polar solvent is dichloromethane, chloroform, n-hexane, hexamethylene, toluene, dimethylbenzene, chlorobenzene, fluorobenzene.
8. the preparation method of according to claim 7 pair of fluorine sulfimide lithium, it is characterised in that：Step 4) described in depressurize
Dry temperature is 60~120 DEG C.
9. the preparation method of according to claim 1 pair of fluorine sulfimide lithium, it is characterised in that：Step 5) described in pole
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 according to claim 8 pair of fluorine sulfimide lithium, it is characterised in that：Step 5) described in
Weak polar solvent is dichloromethane, chloroform, n-hexane, hexamethylene, toluene, dimethylbenzene, chlorobenzene, fluorobenzene.
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