CN100471843C - 超高纯度离子液体 - Google Patents
超高纯度离子液体 Download PDFInfo
- Publication number
- CN100471843C CN100471843C CNB2006100916371A CN200610091637A CN100471843C CN 100471843 C CN100471843 C CN 100471843C CN B2006100916371 A CNB2006100916371 A CN B2006100916371A CN 200610091637 A CN200610091637 A CN 200610091637A CN 100471843 C CN100471843 C CN 100471843C
- Authority
- CN
- China
- Prior art keywords
- ethyl
- hexyl
- methyl
- piperidines
- propyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 23
- -1 halogen ions Chemical class 0.000 claims abstract description 74
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 12
- 150000003839 salts Chemical group 0.000 claims abstract description 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 150000002148 esters Chemical class 0.000 claims abstract description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 7
- 239000012535 impurity Substances 0.000 claims abstract description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 6
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 5
- 150000002500 ions Chemical class 0.000 claims description 35
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- XTKVXHLYQAWREQ-UHFFFAOYSA-N C(CCCCC)N1CCCCC1.CC1(C(=O)O)CC(C(=O)O)=CC=C1 Chemical class C(CCCCC)N1CCCCC1.CC1(C(=O)O)CC(C(=O)O)=CC=C1 XTKVXHLYQAWREQ-UHFFFAOYSA-N 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 2
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical class C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 150000001450 anions Chemical class 0.000 abstract description 2
- 125000005842 heteroatom Chemical group 0.000 abstract description 2
- 150000001768 cations Chemical class 0.000 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 150000002466 imines Chemical class 0.000 description 32
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 19
- 239000007788 liquid Substances 0.000 description 18
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 17
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 17
- 229910052740 iodine Inorganic materials 0.000 description 17
- 239000011630 iodine Substances 0.000 description 17
- 238000005406 washing Methods 0.000 description 17
- IBZJNLWLRUHZIX-UHFFFAOYSA-N 1-ethyl-3-methyl-2h-imidazole Chemical compound CCN1CN(C)C=C1 IBZJNLWLRUHZIX-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- 239000006227 byproduct Substances 0.000 description 14
- 238000001035 drying Methods 0.000 description 14
- 238000009835 boiling Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 238000001291 vacuum drying Methods 0.000 description 13
- 229910052728 basic metal Inorganic materials 0.000 description 12
- 150000003818 basic metals Chemical class 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 10
- 229910052744 lithium Inorganic materials 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 6
- JFYZBXKLRPWSGV-UHFFFAOYSA-N 1-methyl-3-propyl-2h-imidazole Chemical group CCCN1CN(C)C=C1 JFYZBXKLRPWSGV-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000002091 cationic group Chemical group 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- WGVGZVWOOMIJRK-UHFFFAOYSA-N 1-hexyl-3-methyl-2h-imidazole Chemical group CCCCCCN1CN(C)C=C1 WGVGZVWOOMIJRK-UHFFFAOYSA-N 0.000 description 4
- 241000370738 Chlorion Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 description 4
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 150000003233 pyrroles Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- GPJMFSUXLZGWOB-UHFFFAOYSA-N methanesulfonate;1-methyl-3-propyl-1,2-dihydroimidazol-1-ium Chemical class CS([O-])(=O)=O.CCCN1C[NH+](C)C=C1 GPJMFSUXLZGWOB-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- UHACCAYBQFRCLA-UHFFFAOYSA-N COP([O-])([O-])=O.C(C)[NH+](CCCCCC)CC.C(C)[NH+](CC)CCCCCC Chemical compound COP([O-])([O-])=O.C(C)[NH+](CCCCCC)CC.C(C)[NH+](CC)CCCCCC UHACCAYBQFRCLA-UHFFFAOYSA-N 0.000 description 2
- FPRGCLYNTRPPKK-UHFFFAOYSA-M COS(=O)(=O)[O-].P.C(CCC)[P+](C)(CCCC)CCCC Chemical compound COS(=O)(=O)[O-].P.C(CCC)[P+](C)(CCCC)CCCC FPRGCLYNTRPPKK-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- STJJPRRQKJUYMP-UHFFFAOYSA-N P.C(CCC)[P+](C)(CCCC)CCCC Chemical compound P.C(CCC)[P+](C)(CCCC)CCCC STJJPRRQKJUYMP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229950000081 metilsulfate Drugs 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- KSTMTOKQIFRQFU-UHFFFAOYSA-N 1,3-diethyl-2,4-dihydropyrimidine Chemical compound CCN1CC=CN(CC)C1 KSTMTOKQIFRQFU-UHFFFAOYSA-N 0.000 description 1
- RYNROCNODWBDCM-UHFFFAOYSA-N 1,3-diethyl-2h-imidazole Chemical group CCN1CN(CC)C=C1 RYNROCNODWBDCM-UHFFFAOYSA-N 0.000 description 1
- LYICDNKASUOOKJ-UHFFFAOYSA-N 1,3-dihexyl-2,4-dihydropyrimidine Chemical compound C(CCCCC)N1CN(CC=C1)CCCCCC LYICDNKASUOOKJ-UHFFFAOYSA-N 0.000 description 1
- YUCALBGNKZWBAS-UHFFFAOYSA-N 1,3-dioctyl-2,4-dihydropyrimidine Chemical compound C(CCCCCCC)N1CN(CC=C1)CCCCCCCC YUCALBGNKZWBAS-UHFFFAOYSA-N 0.000 description 1
- QKIFHHOMAJKPMR-UHFFFAOYSA-N 1,3-dipropyl-2,4-dihydropyrimidine Chemical compound C(CC)N1CN(CC=C1)CCC QKIFHHOMAJKPMR-UHFFFAOYSA-N 0.000 description 1
- MHNZOAWYQMOKBW-UHFFFAOYSA-N 1,3-dipropyl-2h-imidazole Chemical group CCCN1CN(CCC)C=C1 MHNZOAWYQMOKBW-UHFFFAOYSA-N 0.000 description 1
- XSOAAEPYSZTVQH-UHFFFAOYSA-N 1,4-dihexylpyrazine Chemical compound CCCCCCN1C=CN(CCCCCC)C=C1 XSOAAEPYSZTVQH-UHFFFAOYSA-N 0.000 description 1
- WHFWPHHVDPDHPA-UHFFFAOYSA-N 1,4-dioctylpyrazine Chemical compound CCCCCCCCN1C=CN(CCCCCCCC)C=C1 WHFWPHHVDPDHPA-UHFFFAOYSA-N 0.000 description 1
- MVLNEVZQYNOBKG-UHFFFAOYSA-N 1,4-dipropylpyrazine Chemical compound CCCN1C=CN(CCC)C=C1 MVLNEVZQYNOBKG-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- UCRIXEWTILHNCG-UHFFFAOYSA-N 1-ethyl-2h-pyridine Chemical compound CCN1CC=CC=C1 UCRIXEWTILHNCG-UHFFFAOYSA-N 0.000 description 1
- GPIWNNXNJMDRFZ-UHFFFAOYSA-N 1-ethyl-3-hexyl-2,4-dihydropyrimidine Chemical compound C(C)N1CN(CC=C1)CCCCCC GPIWNNXNJMDRFZ-UHFFFAOYSA-N 0.000 description 1
- DBEOJSGWSSYQNG-UHFFFAOYSA-N 1-ethyl-3-hexyl-2h-imidazole Chemical group CCCCCCN1CN(CC)C=C1 DBEOJSGWSSYQNG-UHFFFAOYSA-N 0.000 description 1
- RPTKQDAWXYANBY-UHFFFAOYSA-N 1-ethyl-3-methyl-2,4-dihydropyrimidine Chemical compound CCN1CN(C)CC=C1 RPTKQDAWXYANBY-UHFFFAOYSA-N 0.000 description 1
- AKSDACRPILJMDX-UHFFFAOYSA-N 1-ethyl-3-propyl-2h-imidazole Chemical group CCCN1CN(CC)C=C1 AKSDACRPILJMDX-UHFFFAOYSA-N 0.000 description 1
- SZRFIMOYLZSESW-UHFFFAOYSA-N 1-ethyl-4-hexylpyrazine Chemical compound CCCCCCN1C=CN(CC)C=C1 SZRFIMOYLZSESW-UHFFFAOYSA-N 0.000 description 1
- DRBAPEMZHMMLCT-UHFFFAOYSA-N 1-ethyl-4-methylpyrazine Chemical compound CCN1C=CN(C)C=C1 DRBAPEMZHMMLCT-UHFFFAOYSA-N 0.000 description 1
- FROQVHAYMSVXTG-UHFFFAOYSA-N 1-hexyl-2h-pyridine Chemical compound CCCCCCN1CC=CC=C1 FROQVHAYMSVXTG-UHFFFAOYSA-N 0.000 description 1
- DWWPXUNOHOFXIZ-UHFFFAOYSA-N 1-hexyl-3-propyl-2h-imidazole Chemical group CCCCCCN1CN(CCC)C=C1 DWWPXUNOHOFXIZ-UHFFFAOYSA-N 0.000 description 1
- PJGHPXPFOAYUCW-UHFFFAOYSA-N 1-hexyl-4-methylpyrazine Chemical compound CCCCCCN1C=CN(C)C=C1 PJGHPXPFOAYUCW-UHFFFAOYSA-N 0.000 description 1
- VIHZQSOIAPTCGJ-UHFFFAOYSA-N 1-pentyl-2h-pyridine Chemical compound CCCCCN1CC=CC=C1 VIHZQSOIAPTCGJ-UHFFFAOYSA-N 0.000 description 1
- XLXCHZCQTCBUOX-UHFFFAOYSA-N 1-prop-2-enylimidazole Chemical compound C=CCN1C=CN=C1 XLXCHZCQTCBUOX-UHFFFAOYSA-N 0.000 description 1
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2MP Natural products CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 1
- VWLSFXXNCDWLLM-UHFFFAOYSA-N 3-ethyl-n,n-dimethylpentan-3-amine Chemical compound CCC(CC)(CC)N(C)C VWLSFXXNCDWLLM-UHFFFAOYSA-N 0.000 description 1
- DRJSZMDEYSEWKB-UHFFFAOYSA-N 3-hexyl-1-methyl-2,4-dihydropyrimidine Chemical compound CN1CN(CC=C1)CCCCCC DRJSZMDEYSEWKB-UHFFFAOYSA-N 0.000 description 1
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- ZSQNVDXIAIHROP-UHFFFAOYSA-N C(CC)C=1NC=CC1.CC1(C(=O)O)CC(C(=O)O)=CC=C1 Chemical compound C(CC)C=1NC=CC1.CC1(C(=O)O)CC(C(=O)O)=CC=C1 ZSQNVDXIAIHROP-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- ATQAGVROBHFKKD-UHFFFAOYSA-N N1=CC=CC2=CC=CC=C12.CN1C=C(C=C1)CCC Chemical compound N1=CC=CC2=CC=CC=C12.CN1C=C(C=C1)CCC ATQAGVROBHFKKD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- KSRKBDUROZKZBR-UHFFFAOYSA-N diethyl-methyl-propylazanium Chemical compound CCC[N+](C)(CC)CC KSRKBDUROZKZBR-UHFFFAOYSA-N 0.000 description 1
- JYZMHBGJHAWIME-UHFFFAOYSA-N dihydrogen phosphate;trimethylazanium Chemical compound CN(C)C.OP(O)(O)=O JYZMHBGJHAWIME-UHFFFAOYSA-N 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RYPKRALMXUUNKS-UHFFFAOYSA-N hex-2-ene Chemical compound CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 1
- XTPRURKTXNFVQT-UHFFFAOYSA-N hexyl(trimethyl)azanium Chemical compound CCCCCC[N+](C)(C)C XTPRURKTXNFVQT-UHFFFAOYSA-N 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical class COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TYRGSDXYMNTMML-UHFFFAOYSA-N propyl hydrogen sulfate Chemical compound CCCOS(O)(=O)=O TYRGSDXYMNTMML-UHFFFAOYSA-N 0.000 description 1
- DKORSYDQYFVQNS-UHFFFAOYSA-N propyl methanesulfonate Chemical compound CCCOS(C)(=O)=O DKORSYDQYFVQNS-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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Abstract
本发明提供一种卤离子等杂质含量极低的离子液体,该离子液体较为价廉易得。包括一对阳离子K+和阴离子A-的通式(1):K+A-所表示的离子液体,其中作为杂质的碱金属的含量小于等于5ppm,并且卤离子的含量小于等于1ppm。阳离子可以通过使用下面通式(3)所表示的酸酯将叔胺化物或叔膦化物季盐化后,再进行盐交换得到,优选选自下述通式(2)所表示的组。通式(2):【化1】通式(3):ROY【化2】其中,式(2)中,R1~R4分别为碳原子数为1~8的直链或支链烷基,X是杂原子。在式(3)中,R是碳原子数为1~8的直链或支链烷基。
Description
技术领域
本发明涉及有效应用于电化学装置中的无卤高纯度离子液体。
背景技术
离子液体由于难挥发性而不能通过蒸馏来精制。所以,使其高纯度一直认为是重要的课题之一。
以往的离子液体是通过用烷基卤化物来季盐化来合成阳离子鎓盐,再用作为阴离子的酸(HA)或盐(MA)将其盐交换来合成的。
通过这种方法合成的离子液体,经过具有卤离子作为抗衡离子的阳离子鎓盐,转化成目标的离子液体后,也存在卤离子残留的问题。特别是对于卤离子的混入给装置材料的使用带来很大影响的情况,需要完全没有卤离子的离子液体。
作为除去卤离子的方法,一般是使用酸(HA)来形成卤化氢以使其挥发的方法,但是这种方法会产生腐蚀性有害气体。另外,使用阴离子的碱金属盐(MA)使卤离子形成碱金属盐(MX),再经水洗除去的方法也被广泛使用,但是这种方法难以除去原料和由此带来的有机卤化物(非专利文献1)。作为其它的卤素除去方法,在1992年的Journal of Chem.Soc.Chem.Comm.P965中报道有使用乙酸银等使卤离子形成不溶性卤化银以除去的方法,另外,在特表平09-509888号公报中使用铅盐形成不溶性卤化铅以除去卤离子的方法,这些方法中所使用的金属盐价格昂贵、生成含有有害金属的废弃物,因此难以称得上是价廉简单的合成法。
【专利文献1】特表平09-509888号公报
【非专利文献1】绿色化学系列(green chemistry series)vol.2(离子液体的性能创立和应用)NTS出版,2004年2月1日,P.31-32
【非专利文献2】Journal of Chem.Soc.Chem.Comm.P965
发明内容
如上所述,在以往的季盐化剂使用烷基卤化物来制备离子液体时,经过卤离子作为抗衡离子的阳离子鎓盐,卤离子会形成有害气体而挥发,因而需要使用昂贵的试剂以除去,并且难以达到完全无卤。因此,如果在电池或电容器等电化学装置中使用那样的离子液体,就会存在由于卤离子而导致电极腐蚀等的问题。
鉴于这些问题,本发明的目的在于提供一种卤离子等杂质的含量极低的离子液体,该离子液体较为价廉易得并适用于各种电化学装置。
权利要求1的离子液体是下述通式(1)所表示的包括一对阳离子K+和阴离子A-的离子液体,其中作为杂质的碱金属的含量小于等于5ppm,并且卤离子的含量小于等于1ppm。
通式(1):K+A-
权利要求2的上述阳离子优选1种或至少2种选自下述通式(2)所示阳离子。
通式(2)
[化1]
其中,在式(2)中,R1~R4分别为碳原子数为1~8的直链或支链烷基,也可以包括至少一组相同的基团。X是氧、硫等杂原子。
上述的阳离子可以是用下述通式(3)所表示的酸酯将叔胺化物或叔膦化物季盐化后通过盐交换得到。(权利要求3)
通式(3):ROY
【化2】
其中,通式(3)中,R是碳原子数为1~8的直链或支链烷基,在一个化合物中所含的两个R可以相同也可以不同。
根据本发明,以卤离子为代表的杂质的含量极低,因此可以提供一种适用于电化学装置的高纯度离子性液体。
本发明的无卤高纯度离子液体可以通过使用价廉的适合于工业中使用的酸酯将各种叔胺化物或叔膦化物季盐化,再与目标阴离子进行盐交换,可以容易地、价廉地获得。
适用于本发明的上述通式(1)所示化合物的阳离子K+没有特别的限定,例如,可以列举咪唑鎓阳离子、吡咯鎓阳离子、吡啶鎓阳离子、嘧啶鎓阳离子、吡嗪鎓阳离子、铵阳离子、吡咯烷鎓阳离子、哌啶鎓阳离子、磷阳离子、鏻阳离子、膦阳离子等,也可以列举如吗啉或硫代吗啉等含有氧或硫等杂原子的物质。
更加具体地,可以列举1,3-二甲基咪唑鎓、1-甲基-3-乙基咪唑鎓、1-甲基-3-丙基咪唑鎓、1-甲基-3-己基咪唑鎓、1-甲基-3-辛基咪唑鎓、1,3-二乙基咪唑鎓、1-乙基-3-丙基咪唑鎓、1-乙基-3-己基咪唑鎓、1-乙基-3-辛基咪唑鎓、1,3-二丙基咪唑鎓、1-己基-3-丙基咪唑鎓、1-丙基-3-辛基咪唑鎓、1,1-二甲基吡咯鎓、1-乙基-1-甲基吡咯鎓、1-甲基-1-丙基吡咯鎓、1-己基-1-甲基吡咯鎓、1-甲基-1-辛基吡咯鎓、1,1-二乙基吡咯鎓、1-乙基-1-丙基吡咯鎓、1-乙基-1-己基吡咯鎓、1-乙基-1-辛基吡咯鎓、1,1-二丙基吡咯鎓、1-丙基-1-己基吡咯鎓、1-辛基-1-丙基吡咯鎓、1-甲基-1-戊基吡咯鎓、1-乙基-1-戊基吡咯鎓、1,1-二戊基吡咯鎓、1,1-二己基吡咯鎓、1-己基-1-辛基吡咯鎓、1-甲基吡啶鎓、1-乙基吡啶鎓、1-丙基吡啶鎓、1-戊基吡啶鎓、1-己基吡啶鎓、1-辛基吡啶鎓、1,3-二甲基嘧啶鎓、1-乙基-3-甲基嘧啶鎓、1-甲基-3-丙基嘧啶鎓、1-甲基-3-己基嘧啶鎓、1-甲基-3-辛基嘧啶鎓、1,3-二乙基嘧啶鎓、1-乙基-3-丙基嘧啶鎓、1-乙基-3-己基嘧啶鎓、1-乙基-3-辛基嘧啶鎓、1,3-二丙基嘧啶鎓、1-己基-3-丙基嘧啶、1-辛基-3-丙基嘧啶鎓、1,3-二己基嘧啶鎓、1-己基-3-辛基嘧啶鎓、1,3-二辛基嘧啶鎓、1,4-二甲基吡嗪鎓、1-乙基-4-甲基吡嗪鎓、1-甲基-4-丙基吡嗪鎓、1-甲基-4-己基吡嗪鎓、1-甲基-4-辛基吡嗪鎓、1,4-二乙基吡嗪鎓、1-乙基-4-丙基吡嗪鎓、1-乙基-4-己基吡嗪鎓、1-乙基-4-辛基吡嗪鎓、1,4-二丙基吡嗪鎓、1-己基-4-丙基吡嗪鎓、1-辛基-4-丙基吡嗪鎓、1,4-二己基吡嗪鎓、1-己基-4-辛基吡嗪鎓、1,4-二辛基吡嗪鎓、己基三甲基铵、二乙基二甲基丙基铵、二乙基甲基丙基铵、辛基二乙基甲基铵、1,1-二甲基吡咯烷鎓、1-乙基-1-甲基吡咯烷鎓、1,1-二乙基吡咯烷鎓、1-甲基-1-丙基吡咯烷鎓、1-甲基-1-己基吡咯烷鎓、1-甲基-1-辛基吡咯烷鎓、1-乙基-1-丙基吡咯烷鎓、1,1-二丙基吡咯烷鎓、1-乙基-1-己基吡咯烷鎓、1-乙基-1-辛基吡咯烷鎓、1-己基-1-丙基吡咯烷鎓、1-辛基-1-丙基吡咯烷鎓、1,1-二己基吡咯烷鎓、1-己基-1-辛基吡咯烷鎓、1,1-二辛基吡咯烷鎓、1,1-二甲基哌啶鎓、1-乙基-1-甲基哌啶鎓、1,1-二乙基哌啶鎓、1-甲基-1-丙基哌啶鎓、1-甲基-1-己基哌啶鎓、1-甲基-1-辛基哌啶鎓、1-乙基-1-丙基哌啶鎓、1,1-二丙基哌啶鎓、1-乙基-1-己基哌啶鎓、1-乙基-1-辛基哌啶鎓、1-己基-1-丙基哌啶鎓、1-辛基-1-丙基哌啶鎓、1,1-二己基哌啶鎓、1-己基-1-辛基哌啶鎓、1,1-二辛基哌啶鎓、己基三甲基鏻鎓、辛基三甲基鏻鎓、己基二乙基甲基鏻鎓、辛基二乙基甲基鏻鎓、二乙基二甲基丙基鏻鎓、4-甲基-4-乙基吗啉、4-甲基-4-丙基吗啉、4-乙基-4-己基吗啉、4-甲基-4-乙基硫代吗啉、4-甲基-4-丙基硫代吗啉和4-乙基-4-己基硫代吗啉等。
适用于本发明上述通式(1)所示化合物的阴离子A-也没有特别的限定,例如,可以列举四氟硼酸盐、六氟磷酸盐等无机氟类阴离子、RSO3 -(式中的R表示烷基或氟代烷基)表示的链烷磺酸盐阴离子、(RSO2)2N-(式中的R表示烷基或氟代烷基)表示的链烷磺酰亚胺阴离子、(XSO2)2N-(式中的X表示卤素)表示的卤化磺酰亚胺阴离子、(RSO2)3C-(式中的R表示烷基或氟代烷基)表示的链烷磺酰碳阴离子和RCOO-(式中的R表示烷基或氟代烷基)表示的有机羧酸等。
在本发明中,通式(2)所表示的阳离子通过用如上所述的酸酯来合成。酸酯是上述通式(3)所表示的化合物,具体地,可以列举硫酸、亚硫酸、磷酸、亚磷酸、碳酸等无机酸酯或磺酸、膦酸和羧酸等有机酸酯。
在上述通式(3)中,R表示碳原子数为1~8的直链或支链烷基。作为R所示的烷基的例子,可以列举甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、戊基、己基、庚基和辛基等碳原子数为1~8的直链或支链烷基,作为优选的例子,可以列举甲基、乙基、丙基和丁基等碳原子数为1~4的或或支链烷基。
在本发明所用的阳离子的合成方法中,相对每摩尔的季胺或季膦化合物,可以使用1~10当量、优选1~3当量的酸酯。在加入酸酯时,由于伴有剧烈放热,因此优选缓慢滴加大于等于1小时。反应温度通常是0℃~200℃,优选20℃~120℃,通过反应1~100小时可以以高收率获得产物。
不使用反应溶剂也可以,但优选使用。作为反应溶剂可以列举甲醇、乙醇、丙醇和乙二醇等醇溶剂;乙酸甲酯、乙酸乙酯、乙酸丙酯、γ-丁内酯和丙酸碳酸酯等酯溶剂;乙腈和丙腈等腈溶剂;苯、甲苯和二甲苯等芳香族溶剂;N,N-二甲基甲酰胺、二甲基亚砜等,可以单独或任意至少两种混合使用。
这样得到的阳离子鎓盐通过与等摩尔量的阴离子碱金属盐,在水或溶剂中混合,在室温下可以容易地进行盐交换。这时使用的溶剂没有特别的限定,优选水、乙腈等腈溶剂,甲醇或乙醇等醇溶剂,可以单独或任意至少两种混合使用。当目标离子液体为疏水性时,最优选水作溶剂,取出反应后分层的离子液体层,加入大于等于30wt%的离子交换水,通过至少1次、优选至少5次的反复水洗和分液,可以得到碱金属含量小于等于5ppm、卤离子含量小于等于1ppm的离子液体。另外,在使用有机溶剂作为反应溶剂的情况下,由于会有副产物盐的析出,因而把析出的盐过滤、将滤液浓缩后再加入大于等于30wt%的离子交换水,通过至少1次、优选至少5次的反复水洗和分液,另外,根据情况,在疏水性的有机溶剂中萃取后,同样地向其中加入为大于等于30wt%的离子交换水,进行大于等于1次,优选大于等于5次的水洗和分液,可以得到碱金属含量小于等于5ppm、卤离子含量小于等于1ppm的离子液体。
本发明的离子液体适用于电化学装置用的电解质盐或电化学装置用的电解液中。在此情况下,根据需要,也可以并用有机溶剂。
实施例
以下表示本发明的实施例,但本发明并不由此被限定。
(1)1-乙基-3-甲基咪唑鎓·二(三氟甲烷磺酰基)亚胺(下式所示化合物)的合成
【化3】
实施例1
在带有搅拌器、滴液漏斗、冷却管和温度计的200ml四口烧瓶中加入1-甲基咪唑32.84g(0.4mol)和甲苯40ml,在40℃下加热。用1小时的时间缓慢向其中滴加硫酸二乙酯67.84g(0.44mol)。另外,此时温度从40℃上升到55℃。滴加完后,在40℃下再反应2小时,然后,通过利用甲苯作为溶剂洗涤除去未反应的硫酸二乙酯。通过减压干燥得到1-乙基-3-甲基咪唑鎓·乙基硫酸盐94.3g。
接着,将得到的1-乙基-3-甲基咪唑鎓·乙基硫酸盐23.63g溶解于10ml水中,然后在室温下向其中加入28.71g(双三氟甲烷磺酰基)亚胺锂溶于10ml水中所形成的溶液,搅拌。将分成两层的下层液体分离,通过加入40wt%的纯水水洗5次除去副产物,真空干燥得到1-乙基-3-甲基咪唑鎓·(双三氟甲烷磺酰基)亚胺34.37g。通过ICP发射光谱分析(以下简称为“ICP分析”)对碱金属离子以及卤离子的含量进行检测,结果其中所含的总的碱金属小于等于1.3ppm,氯离子为0.2ppm,碘和溴分别小于等于0.1ppm(低于ICP检测界限)。
比较例1
在带有搅拌器、滴液漏斗、冷却管和温度计的200ml四口烧瓶中,加入1-甲基咪唑32.84g(0.4mol)和甲苯40ml,在50℃下加热。用1小时的时间缓慢向其中滴加入碘乙烷68.63g(0.44mol)。滴加完后在50℃下再反应4小时,将析出的固体过滤、溶剂洗涤,之后通过减压干燥得到1-乙基-3-甲基咪唑鎓碘盐90.47g。
接着,将得到的1-乙基-3-甲基咪唑鎓碘盐90.47g溶于10ml水中,在室温下向其中加入28.71g(双三氟甲烷磺酰基)亚胺锂溶液溶于10ml水中所形成的溶液,搅拌。将分成两层的下层液体分离,通过加入40wt%的纯水水洗5次除去副产物,真空干燥得到1-乙基-3-甲基咪唑鎓·二(三氟甲烷磺酰基)亚胺33.57g。ICP分析的结果是含有总的碱金属离子为2.8ppm,氯为3.2ppm,碘为4.8ppm。
(2)1-甲基-3-丙基咪唑鎓二(三氟甲烷磺酰基)亚胺(下式所示化合物)的合成
【化4】
实施例2
在带有搅拌器、滴液漏斗、冷却管和温度计的50ml四口烧瓶中加入1-甲基咪唑41.05g(0.5mol)和甲苯50ml,在80℃下加热,然后用大于等于1小时的时间缓慢滴加入甲烷磺酸丙酯76.00g(0.55mol)。在回流温度下搅拌40小时。冷却后,通过甲苯进行溶剂洗涤,通过减压干燥得到1-甲基-3-丙基咪唑鎓甲烷磺酸盐99.13g。接着,将得到的1-甲基-3-丙基咪唑鎓甲烷磺酸盐99.13g溶于80ml水中,并且在室温下使二(三氟甲烷磺酰基)亚胺锂139.24g溶解在80ml水中并搅拌。分成两层后将下层液体取出,通过加入40wt%的纯水水洗5次以除去副产物,真空干燥得到1-甲基-3-丙基咪唑鎓二(三氟甲烷磺酰基)亚胺178.75g。ICP分析的结果是含有总的碱金属小于等于2.1ppm,氯离子为0.6ppm,碘和溴分别小于等于0.1ppm(低于ICP检测界限)。
比较例2
在带有搅拌器、滴液漏斗、冷却管和温度计的50ml四口烧瓶中加入1-甲基咪唑41.05g(0.5mol)和甲苯50ml,在50℃下加热,然后用大于等于1小时的时间缓慢滴加入碘丙烷93.49g(0.55mol)。在50℃下加热搅拌4小时后,过滤析出物,通过用甲苯洗涤减压干燥,得到1-甲基-3-丙基咪唑鎓碘盐122.26g。接着,将得到的1-甲基-3-丙基咪唑鎓甲烷磺酸盐122.26g溶于80ml水中,然后在室温下使二(三氟甲烷磺酰基)亚胺锂139.24g溶解在80ml水中并搅拌。分成两层后将下层液体取出,通过加入40wt%的纯水水洗5次除去副产物,经真空干燥得到1-甲基-3-丙基咪唑鎓二(三氟甲烷磺酰基)亚胺175.39g。ICP分析的结果是含有总的碱金属为2.4ppm,氯为2.9ppm,碘为6.5ppm。
(3)1-甲基-3-己基咪唑鎓二(三氟甲烷磺酰基)亚胺(下式所示化合物)的合成
【化5】
实施例3
在带有搅拌器、滴液漏斗、冷却管和温度计的50ml四口烧瓶中加入1-甲基咪唑41.05g(0.5mol)和甲苯50ml,在80℃下加热,然后用大于等于1小时的时间缓慢滴加入硫酸二己酯146.52g(0.55mol)。在回流温度下搅拌25小时。冷却后,使用甲苯进行溶剂洗涤,通过减压干燥得到1-甲基-3-己基咪唑鎓己基硫酸盐156.83g。接着,将得到的1-甲基-3-己基咪唑鎓己基硫酸盐99.13g溶于80ml水中,在室温下使139.24g二(三氟甲烷磺酰基)亚胺锂溶解在80ml水中并搅拌。分成两层后将下层液体取出,通过加入40wt%的纯水水洗5次以除去副产物,真空干燥得到1-甲基-3-己基咪唑鎓二(三氟甲烷磺酰基)亚胺197.31g。ICP分析的结果是含有总的碱金属2.7ppm,氯离子为0.7ppm,碘和溴分别小于等于0.1ppm(低于ICP检测界限)。
比较例3
在带有搅拌器、滴液漏斗、冷却管和温度计的50ml四口烧瓶中加入1-甲基咪唑41.05g(0.5mol)和甲苯50ml,在50℃下加热,然后用大于等于1小时的时间缓慢滴加入溴代己烷90.24g(0.55mol)。在回流温度下搅拌5小时。冷却后,过滤析出物,通过溶剂洗涤,减压干燥得到1-甲基-3-己基咪唑鎓溴盐119.88g。接着,将得到的1-甲基-3-己基咪唑鎓溴盐119.88g溶于80ml水中,在室温下使139.24g二(三氟甲烷磺酰基)亚胺锂溶解在80ml水中并搅拌。分成两层后将下层液体取出,通过加入40wt%的纯水水洗5次以除去副产物,经真空干燥得到1-甲基-3-己基咪唑鎓二(三氟甲烷磺酰基)亚胺197.31g。ICP分析的结果是含有总的碱金属为3.7ppm,氯为3.3ppm,溴为24ppm。
(4)1-乙基-3-甲基咪唑鎓二(氟代磺酰基)亚胺的合成
【化6】
实施例4
在带有搅拌器、滴液漏斗、冷却管和温度计的200ml四口烧瓶中加入1-甲基咪唑32.84g(0.4mol)和甲苯40ml,在30℃下加热。用1小时的时间向其中缓慢滴加入硫酸二乙酯67.84g(0.44mol)。此时的温度从30℃上升到47℃。滴加完后,在30℃下再反应3小时,之后使用甲苯通过溶剂洗涤除去未反应的硫酸二乙酯。然后,通过减压干燥得到1-乙基-3-甲基咪唑鎓·乙基硫酸盐93.8g。
接着,将得到的1-乙基-3-甲基咪唑鎓·乙基硫酸盐93.8g溶于20ml水中,并且在室温下加入86.82g二(氟代磺酰基)亚胺钾溶于20ml水中所形成的溶液,搅拌。分成两层后将下层液体分离,通过加入40wt%的纯水水洗5次除去副产物,真空干燥得到1-乙基-3-甲基咪唑鎓·二(氟代磺酰基)亚胺107.20g。ICP分析的结果是含有总的碱金属为3.1ppm,氯离子为0.3ppm,碘和溴分别小于等于0.1ppm(低于ICP检测界限)。
比较例4
在带有搅拌器、滴液漏斗、冷却管和温度计的200ml四口烧瓶中加入1-甲基咪唑32.84g(0.4mol)和甲苯40ml,在50℃下加热。用1小时的时间向其中缓慢滴加入碘代乙烷68.63g(0.44mol)。滴加完后,在50℃下再反应4小时,将析出的固体过滤,溶剂洗涤后,经减压干燥得到1-乙基-3-甲基咪唑鎓碘盐90.47g。
接着,将得到的1-乙基-3-甲基咪唑鎓碘盐90.47g溶于20ml水中,并且在室温下加入86.82g二(氟代磺酰基)亚胺钾溶于20ml水中形成的溶液,搅拌。分成两层后将下层液体分离,通过加入40wt%的纯水水洗5次除去副产物,真空干燥得到1-乙基-3-甲基咪唑鎓·二(氟代磺酰基)亚胺95.2g。ICP分析的结果是含有总的碱金属为3.3ppm,氯为3.1ppm,碘为5.1ppm。
(5)二乙基己基甲基铵二(五氟乙烷磺酰基)亚胺(下式所示化合物)的合成
【化7】
实施例5
在带有搅拌器、滴液漏斗、冷却管和温度计的200ml四口烧瓶中加入二乙基己基胺78.65g(0.5mol)和甲醇50ml,加热。用大于等于1小时的时间向其中缓慢滴加入三甲基磷酸70.04g(0.50mol),回流15小时。反应后冷却至室温,通过减压干燥得到二乙基己基甲基铵磷酸盐136.80g。接着,将得到的经减压干燥的二乙基己基甲基铵磷酸盐136.80g溶于50ml水中,并且在室温下加入189.66g二(五氟乙烷磺酰基)亚胺锂溶于50ml水中形成的溶液,搅拌。分成两层后将下层液体分离,通过加入40wt%的纯水水洗5次除去副产物,真空干燥得到二乙基己基甲基铵二(三氟甲烷磺酰基)亚胺262.43g。ICP分析的结果是含有总的碱金属为2.4ppm,氯为0.6ppm,碘和溴分别小于等于0.1ppm(低于ICP检测界限)。
(6)1-乙基-3-甲基咪唑鎓二(五氟乙基磺酰基)亚胺(下式所示化合物)的合成
【化8】
实施例6
在带有搅拌器、滴液漏斗、冷却管和温度计的200ml四口烧瓶中加入1-乙基咪唑48.07g(0.5mol)和甲苯50ml,在100℃下加热。用大于等于1小时的时间向其中缓慢滴加入甲烷磺酸甲酯55.07g(0.50mol),反应25小时。反应后冷却至室温,通过减压干燥得到1-乙基-3-甲基咪唑鎓甲基磺酸盐101.07g。接着,将得到的1-乙基-3-甲基咪唑鎓甲基磺酸盐101.07g溶于50ml水中,并且在室温下加入189.68g二(五氟乙基磺酰基)亚胺锂溶于50ml水中形成的溶液,搅拌。分成两层后将下层液体取出,通过加入40wt%的纯水水洗5次除去副产物,经真空干燥得到1-乙基-3-甲基咪唑鎓二(五氟乙基磺酰基)亚胺228.71g。ICP分析的结果是含有总的碱金属为1.7ppm,氯为0.6ppm,碘和溴分别小于等于0.1ppm(低于ICP检测界限)。
(7)1-烯丙基-1-甲基吡咯烷鎓六氟磷酸盐(下式所示化合物)的合成
【化9】
实施例7
在带有搅拌器、滴液漏斗、冷却管和温度计的200ml四口烧瓶中加入1-烯丙基咪唑54.07g(0.5mol)和甲苯50ml,用大于等于1小时的时间向其中缓慢滴加入硫酸二甲酯63.01g(0.50mol),反应5小时。反应后,通过减压干燥得到1-烯丙基-3-甲基咪唑鎓甲基硫酸盐114.79g。接着,将得到的1-烯丙基-3-甲基咪唑鎓甲基硫酸盐114.79g溶于80ml水中,并且在室温下将74.44g六氟磷酸锂溶于80ml水中,搅拌。分成两层后将下层液体取出,通过加入40wt%的纯水水洗5次除去副产物,经真空干燥得到1-烯丙基-3-甲基咪唑鎓六氟磷酸盐127.37g。ICP分析的结果是含有总的碱金属为2.1ppm,氯为0.4ppm,碘和溴分别小于等于0.1ppm(低于ICP检测界限)。
(8)1-甲基-1-丙基哌啶鎓二(氟代磺酰基)亚胺(下式所示化合物)的合成
【化10】
实施例8
在带有搅拌器、滴液漏斗、冷却管和温度计的50ml四口烧瓶中加入1-甲基哌啶4.96g(0.05mol)和甲苯5ml,在50℃下加热后,用大于等于1小时的时间向其中缓慢滴加入硫酸二丙酯10.02g(0.055mol)。反应10小时后,通过减压干燥得到1-甲基-3-丙基哌啶鎓丙基硫酸盐13.37g。接着,将得到的1-甲基-3-丙基哌啶鎓丙基硫酸盐13.37g溶于8ml水中,并且在室温下使10.5g二(氟代磺酰基)亚胺钾溶于8ml水中,搅拌。分成两层后将下层液体取出,通过加入40wt%的纯水水洗5次以除去副产物,真空干燥得到1-甲基-3-丙基吡咯啉二(氟代磺酰基)亚胺15.31g。ICP分析的结果是含有总的碱金属为1.8ppm,氯为0.5ppm,碘和溴分别小于等于0.1ppm(低于ICP检测界限)。
(9)三丁基甲基膦鎓二(三氟甲烷磺酰基)亚胺(下式所示化合物)的合成
【化11】
实施例9
在带有搅拌器、滴液漏斗、冷却管和温度计的50ml四口烧瓶中加入三丁基膦101.16g(0.5mol)和甲苯50ml,用大于等于1小时的时间向其中缓慢滴加入硫酸二甲酯63.07g(0.05mol)。反应后,通过甲苯进行溶剂洗涤,通过减压干燥得到三丁基甲基膦鎓甲基硫酸盐159.30g。接着,将得到的三丁基甲基膦鎓甲基硫酸盐159.30g溶于80ml水中,并且在室温下使139.24g二(三氟甲烷磺酰基)亚胺锂溶于80ml水中,搅拌。分成两层后将下层液体取出,通过加入40wt%的纯水水洗5次以除去副产物,真空干燥得到三丁基甲基膦鎓二(三氟甲烷磺酰基)亚胺422.88g。ICP分析的结果是含有总的碱金属为1.6ppm,氯为0.5ppm,碘和溴分别小于等于0.1ppm(低于ICP检测界限)。
本发明的离子液体适用作电池或电容器等电化学装置使用的电解质或反应溶剂。
Claims (2)
1、一种离子液体,包括一对阳离子K+和阴离子A-的如下通式(1)所表示的离子液体,阳离子为1种或至少2种选自下述通式(2)以及1,1-二甲基吡咯烷鎓、1-乙基-1-甲基吡咯烷鎓、1,1-二乙基吡咯烷鎓、1-甲基-1-丙基吡咯烷鎓、1-甲基-1-己基吡咯烷鎓、1-甲基-1-辛基吡咯烷鎓、1-乙基-1-丙基吡咯烷鎓、1,1-二丙基吡咯烷鎓、1-乙基-1-己基吡咯烷鎓、1-乙基-1-辛基吡咯烷鎓、1-己基-1-丙基吡咯烷鎓、1-辛基-1-丙基吡咯烷鎓、1,1-二己基吡咯烷鎓、1-己基-1-辛基吡咯烷鎓、1,1-二辛基吡咯烷鎓、1,1-二甲基哌啶鎓、1-乙基-1-甲基哌啶鎓、1,1-二乙基哌啶鎓、1-甲基-1-丙基哌啶鎓、1-甲基-1-己基哌啶鎓、1-甲基-1-幸基哌啶鎓、1-乙基-1-丙基哌啶鎓、1,1-二丙基哌啶鎓、1-乙基-1-己基哌啶鎓、1-乙基-1-辛基哌啶鎓、1-己基-1-丙基哌啶鎓、1-辛基-1-丙基哌啶鎓、1,1-二己基哌啶鎓、1-己基-1-辛基哌啶鎓、1,1-二辛基哌哌啶鎓、4-甲基-4-乙基吗啉、4-甲基-4-丙基吗啉、4-乙基-4-己基吗啉、4-甲基-4-乙基硫代吗啉、4-甲基-4-丙基硫代吗啉和4-乙基-4-乙基硫代吗啉的阳离子,阴离子为(XSO2)2N-表示的卤化磺酰亚胺阴离子,式中的X表示卤素,作为杂质的碱金属的含量小于等于5ppm,并且卤离子的含量小于等于1ppm,
通式(1):K+A-,
通式(2):
其中,在式(2)中,R1~R4分别为碳原子数为1~8的直链或支链烷基。
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US9796791B2 (en) | 2011-04-13 | 2017-10-24 | Eastman Chemical Company | Cellulose ester optical films |
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US7605271B2 (en) | 2009-10-20 |
TWI306856B (en) | 2009-03-01 |
EP1707265A1 (en) | 2006-10-04 |
CA2537587C (en) | 2012-01-17 |
JP4499594B2 (ja) | 2010-07-07 |
JP2006278167A (ja) | 2006-10-12 |
CA2537587A1 (en) | 2006-09-29 |
KR100770925B1 (ko) | 2007-10-26 |
TW200639152A (en) | 2006-11-16 |
CN1854129A (zh) | 2006-11-01 |
KR20060105452A (ko) | 2006-10-11 |
US20060223995A1 (en) | 2006-10-05 |
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