CN108503670A - 一种氟磷酰亚胺及其碱金属盐的制备方法 - Google Patents
一种氟磷酰亚胺及其碱金属盐的制备方法 Download PDFInfo
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- CN108503670A CN108503670A CN201810320751.XA CN201810320751A CN108503670A CN 108503670 A CN108503670 A CN 108503670A CN 201810320751 A CN201810320751 A CN 201810320751A CN 108503670 A CN108503670 A CN 108503670A
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- phosphorimide
- fluorine
- added
- alkali metal
- metal salt
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- -1 alkali metal salt Chemical class 0.000 title claims abstract description 80
- 229910052783 alkali metal Inorganic materials 0.000 title claims abstract description 32
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 31
- 239000011737 fluorine Substances 0.000 title claims abstract description 30
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 239000003960 organic solvent Substances 0.000 claims abstract description 17
- 238000001914 filtration Methods 0.000 claims abstract description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000706 filtrate Substances 0.000 claims abstract description 13
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 13
- ZSTLPJLUQNQBDQ-UHFFFAOYSA-N azanylidyne(dihydroxy)-$l^{5}-phosphane Chemical class OP(O)#N ZSTLPJLUQNQBDQ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000007787 solid Substances 0.000 claims abstract description 8
- 238000005292 vacuum distillation Methods 0.000 claims abstract description 8
- AFCIMSXHQSIHQW-UHFFFAOYSA-N [O].[P] Chemical compound [O].[P] AFCIMSXHQSIHQW-UHFFFAOYSA-N 0.000 claims abstract description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 6
- 239000006227 byproduct Substances 0.000 claims abstract description 5
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 4
- 239000000047 product Substances 0.000 claims abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 3
- 239000003495 polar organic solvent Substances 0.000 claims abstract description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 19
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 16
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 12
- 229910052744 lithium Inorganic materials 0.000 claims description 12
- 239000011734 sodium Substances 0.000 claims description 12
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 8
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 claims description 8
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 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 6
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 6
- 229910052808 lithium carbonate Inorganic materials 0.000 claims description 6
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-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
- 229940090181 propyl acetate Drugs 0.000 claims description 4
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- 150000003851 azoles Chemical class 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- GNHQSAUHXKRQMC-UHFFFAOYSA-N benzene;chlorine Chemical compound [Cl].C1=CC=CC=C1 GNHQSAUHXKRQMC-UHFFFAOYSA-N 0.000 claims 1
- 239000012535 impurity Substances 0.000 abstract description 2
- 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
- 229910019188 POF2 Inorganic materials 0.000 description 13
- 239000005457 ice water Substances 0.000 description 10
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 150000002466 imines Chemical class 0.000 description 8
- 239000012265 solid product Substances 0.000 description 8
- 239000012046 mixed solvent Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000003292 diminished effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- QNLVXLJTOLHAMA-UHFFFAOYSA-N N=NC=NN.N=NC=NN.C(O)(O)=O Chemical compound N=NC=NN.N=NC=NN.C(O)(O)=O QNLVXLJTOLHAMA-UHFFFAOYSA-N 0.000 description 2
- 229910019256 POF3 Inorganic materials 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- DGTVXEHQMSJRPE-UHFFFAOYSA-M difluorophosphinate Chemical compound [O-]P(F)(F)=O DGTVXEHQMSJRPE-UHFFFAOYSA-M 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- FFUQCRZBKUBHQT-UHFFFAOYSA-N phosphoryl fluoride Chemical compound FP(F)(F)=O FFUQCRZBKUBHQT-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- COLOHWPRNRVWPI-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound [CH2]C(F)(F)F COLOHWPRNRVWPI-UHFFFAOYSA-N 0.000 description 1
- JUZCVRZJGRPWJZ-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)S(F)(=O)=O JUZCVRZJGRPWJZ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 101000928408 Homo sapiens Protein diaphanous homolog 2 Proteins 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- 102100036469 Protein diaphanous homolog 2 Human genes 0.000 description 1
- WNEYAIJFUGWKBT-UHFFFAOYSA-M S(=O)(=O)=[Cl+].[F-] Chemical compound S(=O)(=O)=[Cl+].[F-] WNEYAIJFUGWKBT-UHFFFAOYSA-M 0.000 description 1
- 239000005935 Sulfuryl fluoride Substances 0.000 description 1
- LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical compound [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000012983 electrochemical energy storage Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/26—Amides of acids of phosphorus containing P-halide groups
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/097—Compounds containing nitrogen and non-metals and optionally metals containing phosphorus atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/18—Salts thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
- C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0567—Liquid materials characterised by the additives
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
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Abstract
本发明公开了一种氟磷酰亚胺及其碱金属盐的制备方法,具体包括以下步骤:1)三氟氧磷和氨气共同通入到有机溶剂中进行反应,过滤后减压蒸馏制备二氟磷酰胺;2)二氟磷酰胺溶解到有机溶剂中,加入叔胺,控制反应温度,加入磷(磺)酰卤或者卤代磷腈;3)过滤除去副产物固体,滤液加入碱金属盐中和反应(或者滤液除去有机溶剂后加入浓硫酸或者浓磷酸,减压蒸馏得到氟磷酰亚胺);4)中和反应后过滤除去固体,减压浓缩反应液,加入弱极性有机溶剂进行重结晶;5)过滤,减压干燥后得到产品。本发明提供的制备工艺简单,反应时间短,收率高,且能有效控制金属离子和阴离子杂质,能够制备得到高纯度的氟磷酸亚胺及其碱金属盐。
Description
技术领域
本发明涉及化合物制备技术领域,尤其涉及氟磷酰胺及其碱金属盐的制备方法。
背景技术
二氟磷酰官能团化合物作为一种新型的锂离子电池电解液添加剂,通过形成稳定的钝化膜,改善负极界面膜的结构成分,有利于降低电池内阻以及提高电池的使用寿命。二氟磷酸锂是这类添加剂最常见的化合物,但是二氟磷酸锂在碳酸酯电解液中溶解度极差,尤其是极性和给体数相对较低的链状碳酸酯,二氟磷酸锂的溶解度一般小于0.1%,极大程度上限值了它的应用。亚胺碱金属盐具有优越的化学稳定性和电化学性能。亚胺碱金属盐单独或者与其它导电盐复合使用,可以显著提升电池的使用寿命,提高功率密度和安全性能等,是电化学储能行业备受关注的新一代导电盐。
发明内容
本发明的目的在于提供一种氟磷酰亚胺及锂(钠)离子电池所需的高纯度氟磷酰亚胺碱金属盐的制备方法。
氟磷酰亚胺及其碱金属盐的结构通式为式(Ⅰ)、(Ⅱ)、(Ⅲ)、(Ⅳ)所示:
其中:
式(Ⅰ)为二氟磷酰苯磺酰亚胺及其碱金属盐;式(Ⅱ)为二氟磷酰亚胺及其碱金属盐;式(Ⅲ)为二氟磷酰五氟磷腈亚胺及其碱金属盐;式(Ⅳ)为二氟磷酰氟烷基磺酰亚胺及其碱金属盐;
R1、R2、R3、R4、R5=H、CxHy、CN、F、CxFyHz,x=1-6,y=1-15,z=1-15;
M=H、Li、Na、K、Rb、Cs;
R6为碳原子数为1-8的含氟烷基,优选结构为CF3、CF3CH2、CF2HCH2、CF3CF2、CF2HCF2CH2、CF3CFHCF2、CF3CF2CH2、CF3CF2CF2、HCF2CF2CF2CH2、CF2HCF2CF2CF2、(CH2F)2CH、(CF3)3C、CF3CF2CF2CF2、CF3(CF2CF2)2CF2、HCF2CF2OCH2CH2CH2、CF3(CF2CF2)3CF2。
为解决以上技术问题,本发明采用如下技术方案:一种氟磷酰亚胺的制备方法,包括以下步骤:
1)三氟氧磷和氨气共同通入到有机溶剂中进行反应,过滤后减压蒸馏制备二氟磷酰胺;
2)二氟磷酰胺溶解到有机溶剂中,加入叔胺,控制反应温度,加入磷(磺)酰卤或者卤代磷腈;
3)过滤除去副产物固体,减压除去有机溶剂,得到氟磷酰亚胺叔铵盐,加入浓硫酸或者浓磷酸,减压蒸馏得到氟磷酰亚胺。
优选的,上述步骤1)和步骤2)中所述有机溶剂包括乙腈、丙酮、碳酸二甲酯、碳酸二乙酯、碳酸甲乙酯、乙酸乙酯、乙酸丙酯、乙酸丁酯、乙醚、甲基叔丁基醚、二氯甲烷、三氯甲烷、正己烷、环己烷、甲苯、二甲苯、氯苯、氟苯中的至少一种。
优选的,上述步骤2)中所述叔胺包括三乙胺、三丙胺、三丁胺、二异丙基乙基胺、吡啶、甲基吡啶、咪唑中的至少一种,磷酰胺和叔胺的化学计量摩尔比为1:2~1:6。所述的磷酰胺和磷(磺)酰卤或者卤代磷腈的化学计量摩尔比为1:1~1:3。所述的反应温度为-20~50℃。
本发明还提供了一种氟磷酰亚胺碱金属盐的制备方法,包括以下步骤:
1)三氟氧磷和氨气共同通入到有机溶剂中进行反应,过滤后减压蒸馏制备二氟磷酰胺;
2)二氟磷酰胺溶解到有机溶剂中,加入叔胺,控制反应温度,加入磷(磺)酰卤或者卤代磷腈;
3)过滤除去副产物固体,滤液加入碱金属盐中和反应;
4)过滤除去固体,减压浓缩反应液,加入弱极性有机溶剂进行重结晶;
5)过滤,减压干燥后得到产品。
优选的,步骤1)和步骤2)中所述有机溶剂包括乙腈、丙酮、碳酸二甲酯、碳酸二乙酯、碳酸甲乙酯、乙酸乙酯、乙酸丙酯、乙酸丁酯、乙醚、甲基叔丁基醚、二氯甲烷、三氯甲烷、正己烷、环己烷、甲苯、二甲苯、氯苯、氟苯中的至少一种。
优选的,步骤2)中所述叔胺包括三乙胺、三丙胺、三丁胺、二异丙基乙基胺、吡啶、甲基吡啶、咪唑中的至少一种,磷酰胺和叔胺的化学计量摩尔比为1:2~1:6。所述的磷酰胺和磷(磺)酰卤或者卤代磷腈的化学计量摩尔比为1:1~1:3。所述的反应温度为-20~50℃。
优选的,步骤3)所述的碱金属盐包括碳酸锂、氢氧化锂、烷氧基锂、烷基锂、碳酸钠、氢氧化钠、烷氧基钠中的至少一种。
优选的,步骤4)中所述的弱极性溶剂为二氯甲烷、三氯甲烷、正己烷、环己烷、甲苯、二甲苯、氯苯、氟苯。
优选的,步骤5)中所述减压干燥的温度为60~120℃。
一种氟磷酰亚胺碱金属盐,如上述的的制备方法所制得。
本发明提供的制备工艺简单,反应时间短,收率高,且能有效控制金属离子和阴离子杂质,能够制备得到高纯度的氟磷酸亚胺及其碱金属盐。
氟磷酰亚胺碱金属盐属于亚胺碱金属盐的类似结构,且由于磷酰基(磺酰基)强烈的吸电子效应以及电荷屏蔽效应,使得亚胺阴离子的负电荷密度大幅度降低,体现出较弱的配位能力,使得亚胺碱金属盐具有良好的溶解性和离子解离度,即采用本发明的氟磷酰亚胺碱金属盐在锂(钠)离子电池中溶解性大。
具体实施方式
以下通过特定的具体实例说明本发明的实施方式,本领域技术人员可由本说明书所揭露的内容轻易地了解本发明的其他优点与功效。本发明中提到的一个或多个方法步骤并不排斥在所述组合步骤前后还可以存在其他方法步骤或在这些明确提到的步骤之间还可以插入其他方法步骤,除非另有说明。
实施例1:
POF3+NH3→POF2NH2+NH4F
500mL的反应瓶中加入200mL二氯甲烷,冰水浴,同时通入52g(0.5mol)三氟氧磷和8.5g(0.5mol)氨气,搅拌反应5小时后,减压过滤,得到澄清滤液后减压蒸馏,得到二氟磷酰胺。
500mL的反应瓶,加入50.5g(0.5mol)上步所制备的二氟磷酰胺,加入200mL干燥乙腈以及79g(1mol)吡啶,冰水浴,滴加88.5g(0.5mol)苯磺酰氯,反应8个小时后停止。减压过滤得到澄清滤液,减压除去乙腈,加入浓硫酸,室温下搅拌半个小时后减压蒸馏,得到103.6g产品,产率86%。
500mL的反应瓶,加入50.5g(0.5mol)二氟磷酰胺,加入200mL干燥乙腈以及79g(1mol)吡啶,冰水浴,滴加88.5g(0.5mol)苯磺酰氯,反应8个小时后停止。加入18.5g(0.25mol)碳酸锂,搅拌反应5个小时,减压除去乙腈和吡啶,得到(二氟磷酰)(苯磺酰)亚胺锂粗产品,乙腈/二氯甲烷混合溶剂重结晶,过滤后干燥得到112g白色固体产品,产率90%。(Na<5ppm;K<5ppm;Ca<1ppm;Fe<1ppm;Cl-<5ppm;SO4 2-<5ppm)。
实施例2:
POF2NH2+POF3+Py→(POF2)2NH·Py
(POF2)2NH·Py+Li2CO3→(POF2)2NLi
二氟磷酰胺如实施例1制备。
500mL的反应瓶,加入50.5g(0.5mol)二氟磷酰胺,加入200mL干燥碳酸二甲酯以及86.9g(1.1mol)吡啶,冰水浴,通入31.2g(0.6mol)三氟氧磷,反应8个小时后停止。减压过滤得到澄清滤液,加入18.5g(0.25mol)碳酸锂,搅拌反应5个小时,减压除去碳酸二甲酯和吡啶,得到(二氟磷酰)亚胺锂粗产品,四氢呋喃/二氯乙烷混合溶剂重结晶,过滤后干燥得到142.8g白色固体产品,产率85%。(Na<5ppm;K<5ppm;Ca<1ppm;Fe<1ppm;Cl-<5ppm;SO4 2-<5ppm)。
实施例3:
二氟磷酰胺如实施例1制备。
500mL的反应瓶,加入50.5g(0.5mol)二氟磷酰胺,加入200mL干燥四氢呋喃以及86.9g(1.1mol)吡啶,冰水浴,滴加149.4g(0.6mol)六氟磷腈,反应8个小时后停止。减压过滤得到澄清滤液,加入18.5g(0.25mol)碳酸锂,搅拌反应5个小时,减压除去四氢呋喃和吡啶,得到(二氟磷酰)(五氟磷腈)亚胺锂粗产品,碳酸二甲酯/甲苯混合溶剂重结晶,过滤后干燥得到134.4g白色固体产品,产率80%。(Na<5ppm;K<5ppm;Ca<1ppm;Fe<1ppm;Cl-<5ppm;SO4 2-<5ppm)。
实施例4:
POF2NH2+CF3SO2Cl+Py→(POF2)(CF3SO2)NH·Py
(POF2)(CF3SO2)NH·Py+LiOH→(POF2)(CF3SO2)NLi
二氟磷酰胺如实施例1制备。
500mL的反应瓶,加入50.5g(0.5mol)二氟磷酰胺,加入200mL干燥碳酸二乙酯以及79g(1mol)吡啶,冰水浴,滴加101.4g(0.6mol)三氟甲基磺酰氯,反应10个小时后停止。减压过滤得到澄清滤液,加入12g(0.5mol)氢氧化锂,搅拌反应5个小时,减压除去碳酸二乙酯和吡啶,得到(二氟磷酰)(三氟甲磺酰)亚胺锂粗产品,碳酸二甲酯/甲苯混合溶剂重结晶,过滤后干燥得到100.4g白色固体产品,产率84%。(Na<5ppm;K<5ppm;Ca<1ppm;Fe<1ppm;Cl-<5ppm;SO4 2-<5ppm)。
实施例5:
二氟磷酰胺如实施例1制备。
500mL的反应瓶,加入50.5g(0.5mol)二氟磷酰胺,加入200mL干燥碳酸二甲酯以及101g(1mol)三乙胺,冰水浴,滴加133.5g(0.5mol)五氟苯磺酰氯,反应12个小时后停止。减压过滤得到澄清滤液,加入12g(0.5mol)氢氧化锂,搅拌反应8个小时,减压除去碳酸二甲酯和三乙胺,得到(二氟磷酰)(五氟苯磺酰)亚胺锂粗产品,碳酸二甲酯/正己烷混合溶剂重结晶,过滤后干燥得到131.4g白色固体产品,产率78%。(Na<5ppm;K<5ppm;Ca<1ppm;Fe<1ppm;Cl-<5ppm;SO4 2-<5ppm)。
实施例6:
POF2NH2+C2F5SO2F+(C3H7)3N→(POF2)(C2F5SO2)NH·(C3H7)3N
(POF2)(C2F5SO2)NH·(C3H7)3N+LiOH→(POF2)(C2F5SO2)NLi
二氟磷酰胺如实施例1制备。
500mL的反应瓶,加入50.5g(0.5mol)二氟磷酰胺,加入200mL干燥碳酸二甲酯以及143g(1mol)三丙胺,冰水浴,滴加121.2g(0.6mol)五氟乙基磺酰氟,反应10个小时后停止。减压过滤得到澄清滤液,加入12g(0.5mol)氢氧化锂,搅拌反应8个小时,减压除去碳酸二甲酯和三丙胺,得到(二氟磷酰)(五氟乙基磺酰)亚胺锂粗产品,碳酸二甲酯/二氯甲烷混合溶剂重结晶,过滤后干燥得到118.5g白色固体产品,产率82%。(Na<5ppm;K<5ppm;Ca<1ppm;Fe<1ppm;Cl-<5ppm;SO4 2-<5ppm)。
实施例7:
二氟磷酰胺如实施例1制备。
500mL的反应瓶,加入50.5g(0.5mol)二氟磷酰胺,加入200mL干燥碳酸二甲酯以及101g(1mol)三乙胺,冰水浴,滴加133.5g(0.5mol)五氟苯磺酰氯,反应12个小时后停止。减压过滤得到澄清滤液,加入26.5g(0.25mol)碳酸钠,搅拌反应10个小时,减压除去碳酸二甲酯和三乙胺,得到(二氟磷酰)(五氟苯磺酰)亚胺钠粗产品,碳酸二甲酯/正己烷混合溶剂重结晶,过滤后干燥得到155.3g白色固体产品,产率88%。(K<5ppm;Ca<1ppm;Fe<1ppm;Cl-<5ppm;SO4 2-<5ppm)。
实施例8:
二氟磷酰胺如实施例1制备。
500mL的反应瓶,加入50.5g(0.5mol)二氟磷酰胺,加入200mL干燥四氢呋喃以及86.9g(1.1mol)吡啶,冰水浴,滴加149.4g(0.6mol)六氟磷腈,反应8个小时后停止。减压过滤得到澄清滤液,加入26.5g(0.25mol)碳酸钠,搅拌反应5个小时,减压除去四氢呋喃和吡啶,得到(二氟磷酰)(五氟磷腈)亚胺钠粗产品,碳酸二甲酯/甲苯混合溶剂重结晶,过滤后干燥得到147.8g白色固体产品,产率84%。(K<5ppm;Ca<1ppm;Fe<1ppm;Cl-<5ppm;SO4 2-<5ppm)。
以上所述是本发明的优选实施方式,应当指出,对于本技术领域的普通技术人员来说,在不脱离本发明原理的前提下,还可以做出若干改进和润饰,这些改进和润饰也视为本发明的保护范围。
Claims (10)
1.一种氟磷酰亚胺的制备方法,其特征在于,包括以下步骤:
1)三氟氧磷和氨气共同通入到有机溶剂中进行反应,过滤后减压蒸馏制备二氟磷酰胺;
2)二氟磷酰胺溶解到有机溶剂中,加入叔胺,控制反应温度,加入磷(磺)酰卤或者卤代磷腈;
3)过滤除去副产物固体,减压除去有机溶剂,得到氟磷酰亚胺叔铵盐,加入浓硫酸或者浓磷酸,减压蒸馏得到氟磷酰亚胺。
2.如权利要求1所述的一种氟磷酰亚胺的制备方法,其特征在于:
步骤1)和步骤2)中所述有机溶剂包括乙腈、丙酮、碳酸二甲酯、碳酸二乙酯、碳酸甲乙酯、乙酸乙酯、乙酸丙酯、乙酸丁酯、乙醚、甲基叔丁基醚、二氯甲烷、三氯甲烷、正己烷、环己烷、甲苯、二甲苯、氯苯、氟苯中的至少一种。
3.如权利要求2所述的一种氟磷酰亚胺的制备方法,其特征在于:
步骤2)中所述叔胺包括三乙胺、三丙胺、三丁胺、二异丙基乙基胺、吡啶、甲基吡啶、咪唑中的至少一种,磷酰胺和叔胺的化学计量摩尔比为1:2~1:6。所述的磷酰胺和磷(磺)酰卤或者卤代磷腈的化学计量摩尔比为1:1~1:3。所述的反应温度为-20~50℃。
4.一种氟磷酰亚胺碱金属盐的制备方法,其特征在于,包括以下步骤:
1)三氟氧磷和氨气共同通入到有机溶剂中进行反应,过滤后减压蒸馏制备二氟磷酰胺;
2)二氟磷酰胺溶解到有机溶剂中,加入叔胺,控制反应温度,加入磷(磺)酰卤或者卤代磷腈;
3)过滤除去副产物固体,滤液加入碱金属盐中和反应;
4)过滤除去固体,减压浓缩反应液,加入弱极性有机溶剂进行重结晶;
5)过滤,减压干燥后得到产品。
5.如权利要求4所述的一种氟磷酰亚胺碱金属盐的制备方法,其特征在于:
步骤1)和步骤2)中所述有机溶剂包括乙腈、丙酮、碳酸二甲酯、碳酸二乙酯、碳酸甲乙酯、乙酸乙酯、乙酸丙酯、乙酸丁酯、乙醚、甲基叔丁基醚、二氯甲烷、三氯甲烷、正己烷、环己烷、甲苯、二甲苯、氯苯、氟苯中的至少一种。
6.如权利要求5所述的一种氟磷酰亚胺碱金属盐的制备方法,其特征在于:
步骤2)中所述叔胺包括三乙胺、三丙胺、三丁胺、二异丙基乙基胺、吡啶、甲基吡啶、咪唑中的至少一种,磷酰胺和叔胺的化学计量摩尔比为1:2~1:6。所述的磷酰胺和磷(磺)酰卤或者卤代磷腈的化学计量摩尔比为1:1~1:3。所述的反应温度为-20~50℃。
7.如权利要求6所述的一种氟磷酰亚胺碱金属盐的制备方法,其特征在于:
步骤3)所述的碱金属盐包括碳酸锂、氢氧化锂、烷氧基锂、烷基锂、碳酸钠、氢氧化钠、烷氧基钠中的至少一种。
8.如权利要求7所述的一种氟磷酰亚胺碱金属盐的制备方法,其特征在于:
步骤4)中所述的弱极性溶剂为二氯甲烷、三氯甲烷、正己烷、环己烷、甲苯、二甲苯、氯苯、氟苯。
9.如权利要求8所述的一种氟磷酰亚胺碱金属盐的制备方法,其特征在于:
步骤5)中所述减压干燥的温度为60~120℃。
10.一种氟磷酰亚胺碱金属盐,其特征在于:如权利要求5-10任一项所述的制备方法制得。
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