KR20060076269A - 이온성 액체를 사용하는 불순물 추출 방법 - Google Patents
이온성 액체를 사용하는 불순물 추출 방법 Download PDFInfo
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- KR20060076269A KR20060076269A KR1020067001406A KR20067001406A KR20060076269A KR 20060076269 A KR20060076269 A KR 20060076269A KR 1020067001406 A KR1020067001406 A KR 1020067001406A KR 20067001406 A KR20067001406 A KR 20067001406A KR 20060076269 A KR20060076269 A KR 20060076269A
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 43
- 238000000605 extraction Methods 0.000 title claims description 34
- 239000012535 impurity Substances 0.000 title claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 112
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 16
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims abstract description 15
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims abstract description 13
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 9
- 150000001413 amino acids Chemical class 0.000 claims abstract description 9
- 150000002923 oximes Chemical class 0.000 claims abstract description 9
- 150000001412 amines Chemical class 0.000 claims abstract description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 7
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 7
- 150000002466 imines Chemical class 0.000 claims abstract description 6
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 3
- -1 quinolinium cation Chemical class 0.000 claims description 237
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 33
- 150000001450 anions Chemical class 0.000 claims description 23
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 15
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 14
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 12
- 150000007942 carboxylates Chemical class 0.000 claims description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims description 12
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 11
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 2
- 150000004693 imidazolium salts Chemical class 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical group [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 abstract description 8
- 150000002989 phenols Chemical class 0.000 abstract description 7
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 abstract description 5
- 150000002429 hydrazines Chemical class 0.000 abstract description 2
- 150000002443 hydroxylamines Chemical class 0.000 abstract description 2
- 150000003003 phosphines Chemical class 0.000 abstract description 2
- 150000003455 sulfinic acids Chemical class 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 42
- 239000012071 phase Substances 0.000 description 32
- 125000003118 aryl group Chemical group 0.000 description 23
- 150000003254 radicals Chemical class 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 14
- 230000002051 biphasic effect Effects 0.000 description 14
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 14
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 125000000524 functional group Chemical group 0.000 description 12
- 125000005842 heteroatom Chemical group 0.000 description 12
- 150000003949 imides Chemical class 0.000 description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 229910019142 PO4 Inorganic materials 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 9
- 235000021317 phosphate Nutrition 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002015 acyclic group Chemical group 0.000 description 6
- 235000013877 carbamide Nutrition 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 6
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 6
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 5
- DVWQNBIUTWDZMW-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalen-2-ol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=CC=CC2=C1 DVWQNBIUTWDZMW-UHFFFAOYSA-N 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 5
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 150000004705 aldimines Chemical class 0.000 description 5
- 150000003863 ammonium salts Chemical class 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 5
- 150000002432 hydroperoxides Chemical class 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 5
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 4
- 125000004918 2-methyl-2-pentyl group Chemical group CC(C)(CCC)* 0.000 description 4
- 125000004922 2-methyl-3-pentyl group Chemical group CC(C)C(CC)* 0.000 description 4
- 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 4
- 125000004919 3-methyl-2-pentyl group Chemical group CC(C(C)*)CC 0.000 description 4
- 125000004921 3-methyl-3-pentyl group Chemical group CC(CC)(CC)* 0.000 description 4
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000001642 boronic acid derivatives Chemical class 0.000 description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- 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 4
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
- 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 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 4
- 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 4
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 4
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002262 Schiff base Substances 0.000 description 3
- 150000004753 Schiff bases Chemical class 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 150000001896 cresols Chemical class 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 150000007857 hydrazones Chemical class 0.000 description 3
- 150000007975 iminium salts Chemical class 0.000 description 3
- 150000004658 ketimines Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 150000003871 sulfonates Chemical class 0.000 description 3
- UZZYXUGECOQHPU-UHFFFAOYSA-N sulfuric acid monooctyl ester Natural products CCCCCCCCOS(O)(=O)=O UZZYXUGECOQHPU-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 2
- DOYSIZKQWJYULQ-UHFFFAOYSA-N 1,1,2,2,2-pentafluoro-n-(1,1,2,2,2-pentafluoroethylsulfonyl)ethanesulfonamide Chemical compound FC(F)(F)C(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)C(F)(F)F DOYSIZKQWJYULQ-UHFFFAOYSA-N 0.000 description 2
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 2
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 2
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- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 125000000842 isoxazolyl group Chemical group 0.000 description 1
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- 125000001196 nonadecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([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 1
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 150000004028 organic sulfates Chemical class 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000000913 palmityl 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])C([H])([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 1
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- 125000002958 pentadecyl 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])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 1
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- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
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- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
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- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
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- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
- C07B63/04—Use of additives
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10333258 | 2003-07-21 | ||
| DE10333258.8 | 2003-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20060076269A true KR20060076269A (ko) | 2006-07-04 |
Family
ID=34201370
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020067001406A Withdrawn KR20060076269A (ko) | 2003-07-21 | 2004-07-03 | 이온성 액체를 사용하는 불순물 추출 방법 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7605297B2 (https=) |
| EP (1) | EP1648845B1 (https=) |
| JP (1) | JP2006528599A (https=) |
| KR (1) | KR20060076269A (https=) |
| CN (1) | CN100381406C (https=) |
| AT (1) | ATE395316T1 (https=) |
| DE (1) | DE502004007160D1 (https=) |
| DK (1) | DK1648845T3 (https=) |
| ES (1) | ES2305787T3 (https=) |
| IL (1) | IL172780A0 (https=) |
| WO (1) | WO2005019137A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100958876B1 (ko) * | 2008-04-02 | 2010-05-20 | 삼성엔지니어링 주식회사 | 다양한 극성/비극성 용매 혼화성 이온성 액체 및 그의제조방법 |
| CN104198640A (zh) * | 2014-09-10 | 2014-12-10 | 宁波检验检疫科学技术研究院 | 食品接触材料中酚类物质迁移至油性模拟物的测定方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2875235B1 (fr) * | 2004-09-10 | 2006-11-24 | Inst Francais Du Petrole | Procede de separation des composes oxygenes contenus dans une charge hydrocarbonee, mettant en oeuvre un liquide ionique |
| KR20080009708A (ko) * | 2005-04-07 | 2008-01-29 | 매티슨 트라이-개스 | 유체 저장 및 정제 방법 및 시스템 |
| DE102006005103A1 (de) * | 2006-02-04 | 2007-08-09 | Merck Patent Gmbh | Oxonium- und Sulfoniumsalze |
| US7645438B2 (en) * | 2006-06-27 | 2010-01-12 | Akzo Nobel N.V. | Process for the production of hydrogen peroxide |
| JP5350244B2 (ja) * | 2006-08-18 | 2013-11-27 | インヴィスタ テクノロジーズ エスアエルエル | イオン性液体を用いた抽出方法 |
| US8044120B2 (en) | 2006-10-13 | 2011-10-25 | Basf Aktiengesellschaft | Ionic liquids for solubilizing polymers |
| FR2909667B1 (fr) | 2006-12-12 | 2009-02-20 | Inst Francais Du Petrole | Elimination de l'acetonitrile dans la charge olefinique des procedes de production d'ethers par mise en oeuvre de liquides ioniques. |
| US8075777B2 (en) * | 2007-05-16 | 2011-12-13 | E. I. Du Pont De Nemours And Company | Process for the separation of diastereomers |
| US20100311998A1 (en) * | 2007-08-02 | 2010-12-09 | Akzo Nobel N.V. | Chelating agent based ionic liquids, a process to prepare them, and their use |
| CN101933104B (zh) * | 2007-12-20 | 2016-12-28 | 普罗奥尼克离子物质产品有限公司 | 磁性离子液体作为萃取剂的用途 |
| US7956230B2 (en) * | 2007-12-21 | 2011-06-07 | Chevron U.S.A. Inc. | Reduction of organic halide contamination in hydrocarbon products |
| WO2009101032A1 (de) * | 2008-02-11 | 2009-08-20 | Basf Se | Verfahren zur herstellung von polyamiden |
| CN101970555B (zh) * | 2008-02-11 | 2014-05-28 | 巴斯夫欧洲公司 | 由合成聚合物制备多孔结构的方法 |
| US7812191B2 (en) * | 2008-05-07 | 2010-10-12 | Lyondell Chemical Technology, L.P. | Removing hydrocarbon impurities from acetic acid by ionic liquid extraction |
| US8455703B2 (en) * | 2008-05-26 | 2013-06-04 | Merck Patent Gmbh | Use of ionic liquids with tetracyanoborate anions as a solvents for extraction of alcohols from aqueous solutions |
| ES2338976B1 (es) * | 2008-11-12 | 2011-09-29 | Universidad De Vigo | Proceso para la purificacion de alcanos a partir de su mezcla azeotropica con etanol utilizando como disolvente un liquido ionico. |
| EP2243530A1 (de) * | 2009-04-21 | 2010-10-27 | LANXESS Deutschland GmbH | Verfahren zur Trennung aromatischer Verbindungen |
| JP5813625B2 (ja) | 2009-04-23 | 2015-11-17 | ヴイティーユー ホールディング ゲーエムベーハーＶｔｕ Ｈｏｌｄｉｎｇ Ｇｍｂｈ | イオン性液体を脱水する方法 |
| DE102010028550A1 (de) | 2009-05-05 | 2010-11-11 | Basf Se | Verfahren zur Herstellung von Eisen-Nanopartikel enthaltenden thermoplastischen Polymerformmassen |
| WO2011081764A1 (en) * | 2009-12-15 | 2011-07-07 | Cytec Technology Corp. | Methods and compositions for the removal of impurities from an impurity-loaded ionic liquid |
| EP2468811A1 (de) | 2010-12-21 | 2012-06-27 | Basf Se | Thermoplastische Formmasse |
| EP2468812A1 (de) | 2010-12-21 | 2012-06-27 | Basf Se | Thermoplastische Formmasse |
| AU2012271273B2 (en) | 2011-06-17 | 2017-06-08 | Fluidic, Inc. | Metal-air cell with ion exchange material |
| JP5888993B2 (ja) * | 2012-01-12 | 2016-03-22 | ランクセス・ドイチュランド・ゲーエムベーハー | メントール化合物異性体の分離 |
| WO2013130997A1 (en) * | 2012-03-02 | 2013-09-06 | Research Triangle Institute | Regenerable solvent mixtures for acid-gas separation |
| KR101402386B1 (ko) | 2012-09-27 | 2014-06-27 | 롯데케미칼 주식회사 | 이온성 액체를 사용한 나프타 내 방향족 화합물의 분리방법 |
| US9287597B2 (en) | 2012-11-14 | 2016-03-15 | Fluidic, Inc. | Ionic liquid containing hydroxamate and N-alkyl sulfamate ions |
| EP3000801A4 (en) * | 2013-05-20 | 2017-01-25 | Lotte Chemical Corporation | Method for separating aromatic compounds contained in naphtha |
| CN103467245B (zh) * | 2013-09-23 | 2015-07-01 | 河北科技大学 | 一种利用低共熔溶剂络合脱除乙醇水混合溶液中水分的方法 |
| CN103539742B (zh) * | 2013-10-15 | 2015-08-05 | 河北工业大学 | 一种离子液体型羟胺盐的制备方法 |
| CN103570582B (zh) * | 2013-10-28 | 2015-01-14 | 中建安装工程有限公司 | 利用离子液体[BMIM]NTf2萃取硫酸铵溶液中丁酮肟的方法 |
| CN104326949B (zh) * | 2014-09-19 | 2016-07-27 | 浙江工商大学 | 一种可选择性分离氨基酸的功能化离子液体、制备方法及其应用 |
| WO2019113513A1 (en) | 2017-12-08 | 2019-06-13 | Baker Hughes, A Ge Company, Llc | Ionic liquid based well asphaltene inhibitors and methods of using the same |
| EA202091413A1 (ru) | 2018-07-11 | 2020-09-24 | Бейкер Хьюз Холдингз Ллк | Скважинные ингибиторы асфальтенов на основе ионной жидкости и способы их применения |
| TW202104480A (zh) * | 2019-04-03 | 2021-02-01 | 紐西蘭商艾克福特士技術有限公司 | 溶劑乾燥組成物及其製法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001040150A1 (en) | 1999-12-01 | 2001-06-07 | Akzo Nobel N.V. | Process for the extraction of an aromatic compoung from an aliphatic phase using a non-neutral ionic liavin |
| EP1337605A1 (en) | 2000-10-26 | 2003-08-27 | Chevron U.S.A. Inc. | Removal of mercaptans from hydrocarbon streams using ionic liquids |
| DE10155281A1 (de) * | 2001-11-08 | 2003-06-05 | Solvent Innovation Gmbh | Verfahren zur Entfernung polarisierbarer Verunreinigungen aus Kohlenwasserstoffen und Kohlenwasserstoffgemischen durch Extraktion mit ionischen Flüssigkeiten |
| EP1310543A1 (en) * | 2001-11-07 | 2003-05-14 | Haldor Topsoe A/S | Process for the drying of a hydrocarbon stream |
| EP1354863B1 (en) | 2002-04-18 | 2005-06-08 | Haldor Topsoe A/S | Continuous process for the removal of water from a hydrocarbon stream |
-
2004
- 2004-07-03 KR KR1020067001406A patent/KR20060076269A/ko not_active Withdrawn
- 2004-07-03 AT AT04740602T patent/ATE395316T1/de active
- 2004-07-03 JP JP2006520705A patent/JP2006528599A/ja not_active Withdrawn
- 2004-07-03 EP EP04740602A patent/EP1648845B1/de not_active Expired - Lifetime
- 2004-07-03 ES ES04740602T patent/ES2305787T3/es not_active Expired - Lifetime
- 2004-07-03 DE DE502004007160T patent/DE502004007160D1/de not_active Expired - Lifetime
- 2004-07-03 DK DK04740602T patent/DK1648845T3/da active
- 2004-07-03 CN CNB2004800211651A patent/CN100381406C/zh not_active Expired - Fee Related
- 2004-07-03 US US10/565,187 patent/US7605297B2/en not_active Expired - Fee Related
- 2004-07-03 WO PCT/EP2004/007254 patent/WO2005019137A1/de not_active Ceased
-
2005
- 2005-12-22 IL IL172780A patent/IL172780A0/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100958876B1 (ko) * | 2008-04-02 | 2010-05-20 | 삼성엔지니어링 주식회사 | 다양한 극성/비극성 용매 혼화성 이온성 액체 및 그의제조방법 |
| CN104198640A (zh) * | 2014-09-10 | 2014-12-10 | 宁波检验检疫科学技术研究院 | 食品接触材料中酚类物质迁移至油性模拟物的测定方法 |
| CN104198640B (zh) * | 2014-09-10 | 2016-06-08 | 宁波检验检疫科学技术研究院 | 食品接触材料中酚类物质迁移至油性模拟物的测定方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE502004007160D1 (de) | 2008-06-26 |
| JP2006528599A (ja) | 2006-12-21 |
| US7605297B2 (en) | 2009-10-20 |
| CN100381406C (zh) | 2008-04-16 |
| ATE395316T1 (de) | 2008-05-15 |
| US20070193952A1 (en) | 2007-08-23 |
| EP1648845A1 (de) | 2006-04-26 |
| WO2005019137A8 (de) | 2005-06-16 |
| EP1648845B1 (de) | 2008-05-14 |
| ES2305787T3 (es) | 2008-11-01 |
| WO2005019137A1 (de) | 2005-03-03 |
| IL172780A0 (en) | 2006-04-10 |
| DK1648845T3 (da) | 2008-09-01 |
| CN1826302A (zh) | 2006-08-30 |
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