CA2712365C - Use of magnetic, ionic liquids as an extraction agent - Google Patents
Use of magnetic, ionic liquids as an extraction agent Download PDFInfo
- Publication number
- CA2712365C CA2712365C CA2712365A CA2712365A CA2712365C CA 2712365 C CA2712365 C CA 2712365C CA 2712365 A CA2712365 A CA 2712365A CA 2712365 A CA2712365 A CA 2712365A CA 2712365 C CA2712365 C CA 2712365C
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- paramagnetic
- butyl
- ionic liquid
- pentyl
- 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 61
- 230000005291 magnetic effect Effects 0.000 title claims abstract description 27
- 238000000605 extraction Methods 0.000 title claims abstract description 17
- 239000003795 chemical substances by application Substances 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000007788 liquid Substances 0.000 claims abstract description 14
- 239000007787 solid Substances 0.000 claims abstract description 5
- 238000005192 partition Methods 0.000 claims abstract 2
- -1 transition metal cations Chemical class 0.000 claims description 331
- 125000003118 aryl group Chemical group 0.000 claims description 60
- 230000005298 paramagnetic effect Effects 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 125000001072 heteroaryl group Chemical group 0.000 claims description 39
- 125000005842 heteroatom Chemical group 0.000 claims description 33
- 229920006395 saturated elastomer Polymers 0.000 claims description 30
- 150000001450 anions Chemical class 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000000524 functional group Chemical group 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 14
- 238000002844 melting Methods 0.000 claims description 13
- 230000008018 melting Effects 0.000 claims description 13
- 229910052723 transition metal Inorganic materials 0.000 claims description 12
- 150000003624 transition metals Chemical group 0.000 claims description 10
- 239000003446 ligand Chemical group 0.000 claims description 7
- 150000003623 transition metal compounds Chemical class 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 230000003993 interaction Effects 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 2
- 229910017053 inorganic salt Inorganic materials 0.000 claims 3
- 150000003254 radicals Chemical class 0.000 description 67
- 229910052736 halogen Inorganic materials 0.000 description 35
- 150000002367 halogens Chemical class 0.000 description 31
- 125000004432 carbon atom Chemical group C* 0.000 description 27
- 150000002431 hydrogen Chemical class 0.000 description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 26
- 229910052799 carbon Inorganic materials 0.000 description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 24
- 125000002015 acyclic group Chemical group 0.000 description 24
- 125000001931 aliphatic group Chemical group 0.000 description 24
- 125000004122 cyclic group Chemical group 0.000 description 24
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 20
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 18
- 150000007942 carboxylates Chemical class 0.000 description 17
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 16
- 125000005843 halogen group Chemical group 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 150000001642 boronic acid derivatives Chemical class 0.000 description 12
- 150000003949 imides Chemical class 0.000 description 12
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 9
- 125000004918 2-methyl-2-pentyl group Chemical group CC(C)(CCC)* 0.000 description 9
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 9
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 9
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 9
- 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 9
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 9
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 9
- 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 9
- 125000003709 fluoroalkyl group Chemical group 0.000 description 9
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 9
- 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 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 9
- 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 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 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 9
- 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 9
- 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 9
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 9
- 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 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 229910019142 PO4 Inorganic materials 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 8
- 239000010452 phosphate Substances 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 125000004922 2-methyl-3-pentyl group Chemical group CC(C)C(CC)* 0.000 description 7
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 125000004921 3-methyl-3-pentyl group Chemical group CC(CC)(CC)* 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- DWYMPOCYEZONEA-UHFFFAOYSA-L fluoridophosphate Chemical compound [O-]P([O-])(F)=O DWYMPOCYEZONEA-UHFFFAOYSA-L 0.000 description 6
- 239000011737 fluorine Substances 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
- 150000004028 organic sulfates Chemical class 0.000 description 6
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 6
- 125000003944 tolyl group Chemical group 0.000 description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 6
- 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 5
- 125000004919 3-methyl-2-pentyl group Chemical group CC(C(C)*)CC 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 229910002651 NO3 Inorganic materials 0.000 description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 3
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- CZNJCCVKDVCRKF-UHFFFAOYSA-N Benzyl sulfate Chemical compound OS(=O)(=O)OCC1=CC=CC=C1 CZNJCCVKDVCRKF-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- ZTHQBROSBNNGPU-UHFFFAOYSA-N Butyl hydrogen sulfate Chemical compound CCCCOS(O)(=O)=O ZTHQBROSBNNGPU-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- 125000006539 C12 alkyl 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 3
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 3
- ZQVQTRVXPGGZAU-UHFFFAOYSA-N F[As](F)(F)=O Chemical compound F[As](F)(F)=O ZQVQTRVXPGGZAU-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 229910019567 Re Re Inorganic materials 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 3
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 125000005910 alkyl carbonate group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000001204 arachidyl 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])C([H])([H])[H] 0.000 description 3
- 125000002511 behenyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-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
- 125000003901 ceryl 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])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
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 3
- 229940089960 chloroacetate Drugs 0.000 description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 3
- CSMFSDCPJHNZRY-UHFFFAOYSA-M decyl sulfate Chemical compound CCCCCCCCCCOS([O-])(=O)=O CSMFSDCPJHNZRY-UHFFFAOYSA-M 0.000 description 3
- 229940120124 dichloroacetate Drugs 0.000 description 3
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 3
- PBWZKZYHONABLN-UHFFFAOYSA-M difluoroacetate Chemical compound [O-]C(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-M 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 3
- 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 3
- QEWYKACRFQMRMB-UHFFFAOYSA-M fluoroacetate Chemical compound [O-]C(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-M 0.000 description 3
- GYQYAJJFPNQOOW-UHFFFAOYSA-N gilteritinib Chemical compound N1=C(NC2CCOCC2)C(CC)=NC(C(N)=O)=C1NC(C=C1OC)=CC=C1N(CC1)CCC1N1CCN(C)CC1 GYQYAJJFPNQOOW-UHFFFAOYSA-N 0.000 description 3
- 125000000755 henicosyl 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])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002818 heptacosyl 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])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 3
- MIHVYISIUZTFER-UHFFFAOYSA-N heptyl hydrogen sulfate Chemical compound CCCCCCCOS(O)(=O)=O MIHVYISIUZTFER-UHFFFAOYSA-N 0.000 description 3
- IDUWTCGPAPTSFB-UHFFFAOYSA-N hexyl hydrogen sulfate Chemical compound CCCCCCOS(O)(=O)=O IDUWTCGPAPTSFB-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 3
- 125000002463 lignoceryl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 3
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 3
- 125000002960 margaryl 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])[H] 0.000 description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 3
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- IDYVIRRMXMJBIG-UHFFFAOYSA-N phenyl(2-phenylethyl)phosphane Chemical compound C=1C=CC=CC=1PCCC1=CC=CC=C1 IDYVIRRMXMJBIG-UHFFFAOYSA-N 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940043131 pyroglutamate Drugs 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000000956 solid--liquid extraction Methods 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VFKKSKGQZDULMV-UHFFFAOYSA-J tetrafluoroplatinum Chemical compound F[Pt](F)(F)F VFKKSKGQZDULMV-UHFFFAOYSA-J 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 229940113082 thymine Drugs 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- AUZMWGNTACEWDV-UHFFFAOYSA-L titanium(2+);dibromide Chemical compound Br[Ti]Br AUZMWGNTACEWDV-UHFFFAOYSA-L 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
- SWUFZSQHKFLQTM-UHFFFAOYSA-N tripyrazol-1-yl borate Chemical compound C1=CC=NN1OB(ON1N=CC=C1)ON1C=CC=N1 SWUFZSQHKFLQTM-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- UXVOMHPBSSIGNQ-UHFFFAOYSA-I tungsten(v) bromide Chemical compound Br[W](Br)(Br)(Br)Br UXVOMHPBSSIGNQ-UHFFFAOYSA-I 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01F—MAGNETS; INDUCTANCES; TRANSFORMERS; SELECTION OF MATERIALS FOR THEIR MAGNETIC PROPERTIES
- H01F1/00—Magnets or magnetic bodies characterised by the magnetic materials therefor; Selection of materials for their magnetic properties
- H01F1/44—Magnets or magnetic bodies characterised by the magnetic materials therefor; Selection of materials for their magnetic properties of magnetic liquids, e.g. ferrofluids
- H01F1/447—Magnets or magnetic bodies characterised by the magnetic materials therefor; Selection of materials for their magnetic properties of magnetic liquids, e.g. ferrofluids characterised by magnetoviscosity, e.g. magnetorheological, magnetothixotropic, magnetodilatant liquids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0419—Solvent extraction of solutions which are liquid in combination with an electric or magnetic field or with vibrations
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03C—MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03C1/00—Magnetic separation
- B03C1/005—Pretreatment specially adapted for magnetic separation
- B03C1/015—Pretreatment specially adapted for magnetic separation by chemical treatment imparting magnetic properties to the material to be separated, e.g. roasting, reduction, oxidation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03C—MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03C1/00—Magnetic separation
- B03C1/02—Magnetic separation acting directly on the substance being separated
- B03C1/025—High gradient magnetic separators
- B03C1/031—Component parts; Auxiliary operations
- B03C1/033—Component parts; Auxiliary operations characterised by the magnetic circuit
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/04—Solvent extraction of solutions which are liquid
- B01D11/0492—Applications, solvents used
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1546907P | 2007-12-20 | 2007-12-20 | |
| US61/015,469 | 2007-12-20 | ||
| PCT/EP2008/067731 WO2009080648A1 (de) | 2007-12-20 | 2008-12-17 | Anwendung magnetischer, ionischer flüssigkeiten als extraktionsmittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2712365A1 CA2712365A1 (en) | 2009-07-02 |
| CA2712365C true CA2712365C (en) | 2016-05-24 |
Family
ID=40409938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2712365A Expired - Fee Related CA2712365C (en) | 2007-12-20 | 2008-12-17 | Use of magnetic, ionic liquids as an extraction agent |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9005450B2 (enExample) |
| EP (1) | EP2235724B1 (enExample) |
| JP (1) | JP2011506088A (enExample) |
| CN (1) | CN101933104B (enExample) |
| AU (1) | AU2008340098B2 (enExample) |
| BR (1) | BRPI0821720A2 (enExample) |
| CA (1) | CA2712365C (enExample) |
| RU (1) | RU2558726C2 (enExample) |
| WO (1) | WO2009080648A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8888993B2 (en) | 2010-07-30 | 2014-11-18 | Chevron U.S.A. Inc. | Treatment of a hydrocarbon feed |
| CN102091670A (zh) * | 2010-12-29 | 2011-06-15 | 中国科学院过程工程研究所 | 一种磁性离子液体分离浓缩方法 |
| DE102011080230A1 (de) * | 2011-08-01 | 2013-02-07 | Helmholtz-Zentrum Dresden - Rossendorf E.V. | Extraktion von Edelmetall(ionen) mittels ionischer Flüssigkeiten |
| CN102500460B (zh) * | 2011-09-26 | 2014-04-30 | 中国科学院过程工程研究所 | 一种气助超顺磁性萃取方法 |
| DE102011055859A1 (de) | 2011-11-30 | 2013-06-06 | Universität Rostock | Schwefel-freie Übergangsmetall-Isocyanat-basierte ionische Flüssigkeiten |
| CN103130718B (zh) * | 2012-10-10 | 2016-05-25 | 江苏大学 | 一种磁性离子液体及其制备方法和用途 |
| CN105617711B (zh) * | 2014-10-16 | 2018-04-10 | 中国药科大学 | 一种磁性离子液体结合相关微萃取装置用于复杂样品中微量组分分离方法 |
| CN105624439B (zh) * | 2014-10-27 | 2017-11-10 | 有研稀土新材料股份有限公司 | 一种磁流体萃取剂分离低浓度稀土离子的方法 |
| US10322417B2 (en) * | 2015-07-01 | 2019-06-18 | Uchicago Argonne, Llc | Magnetically enhanced phase separation for solvent extraction |
| CN108642033A (zh) * | 2018-04-17 | 2018-10-12 | 天津科技大学 | 一种温和条件下制备弱磁性铁酶复合物的方法 |
| CN110252256B (zh) * | 2019-06-28 | 2021-11-05 | 河北科技大学 | 一种磁性离子液体、其应用和改性活性炭及其制备方法 |
| CN110385198B (zh) * | 2019-08-05 | 2020-07-17 | 潍坊奇为新材料科技有限公司 | 一种用于非金属矿的分选装置 |
| CN112427139B (zh) * | 2020-10-14 | 2021-09-07 | 清华大学 | 磁性液体分筛装置 |
| CN113620820B (zh) * | 2021-08-11 | 2023-12-29 | 辽宁大学 | 一种功能化磁性离子液体及其制备方法和应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8800394L (sv) * | 1988-02-08 | 1989-08-09 | Skf Nova Ab | Superparamagnetiska vaetskor |
| US5043070A (en) * | 1989-11-13 | 1991-08-27 | Board Of Control Of Michigan Technological University | Magnetic solvent extraction |
| JP3657535B2 (ja) * | 2001-05-29 | 2005-06-08 | 株式会社日本トリム | 水素ラジカルの検出方法及び定量分析方法 |
| 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 |
| JP2006528599A (ja) * | 2003-07-21 | 2006-12-21 | ビーエーエスエフ アクチェンゲゼルシャフト | イオン性液体を使用して不純物を抽出する方法 |
| JP4826156B2 (ja) * | 2004-07-28 | 2011-11-30 | 三菱マテリアル株式会社 | Ｃｏ２ガスの精製方法及びその装置並びにその精製に用いられるｃｏ２ガスの吸収液 |
| JP2006160969A (ja) * | 2004-12-10 | 2006-06-22 | Mitsubishi Materials Corp | 灯軽油留分の精製方法及び灯軽油留分を精製する抽出溶剤 |
| JPWO2006132252A1 (ja) * | 2005-06-07 | 2009-01-08 | 三洋化成工業株式会社 | 磁性流体 |
| AR058054A1 (es) * | 2005-09-22 | 2008-01-23 | Du Pont | Utilizacion de liquidos ionicos para la separacion de hidrofluorocarburos |
| JP2007131608A (ja) * | 2005-11-10 | 2007-05-31 | Univ Of Tokyo | 新規ジスプロシウム誘導体 |
| JP2007203205A (ja) * | 2006-02-02 | 2007-08-16 | Nippon Steel Chem Co Ltd | 分離方法及び装置 |
| WO2007094739A1 (en) * | 2006-02-13 | 2007-08-23 | Agency For Science, Technology And Research | Method of processing a biological and/or chemical sample |
-
2008
- 2008-12-17 EP EP08864792.0A patent/EP2235724B1/de not_active Not-in-force
- 2008-12-17 CN CN200880126048.XA patent/CN101933104B/zh not_active Expired - Fee Related
- 2008-12-17 CA CA2712365A patent/CA2712365C/en not_active Expired - Fee Related
- 2008-12-17 RU RU2010130257/07A patent/RU2558726C2/ru not_active IP Right Cessation
- 2008-12-17 BR BRPI0821720-3A patent/BRPI0821720A2/pt not_active Application Discontinuation
- 2008-12-17 US US12/809,234 patent/US9005450B2/en not_active Expired - Fee Related
- 2008-12-17 WO PCT/EP2008/067731 patent/WO2009080648A1/de not_active Ceased
- 2008-12-17 JP JP2010538701A patent/JP2011506088A/ja active Pending
- 2008-12-17 AU AU2008340098A patent/AU2008340098B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU2008340098A1 (en) | 2009-07-02 |
| RU2558726C2 (ru) | 2015-08-10 |
| AU2008340098B2 (en) | 2014-09-04 |
| CN101933104B (zh) | 2016-12-28 |
| EP2235724A1 (de) | 2010-10-06 |
| JP2011506088A (ja) | 2011-03-03 |
| RU2010130257A (ru) | 2012-01-27 |
| US20110020509A1 (en) | 2011-01-27 |
| WO2009080648A1 (de) | 2009-07-02 |
| BRPI0821720A2 (pt) | 2015-06-16 |
| CA2712365A1 (en) | 2009-07-02 |
| US9005450B2 (en) | 2015-04-14 |
| CN101933104A (zh) | 2010-12-29 |
| EP2235724B1 (de) | 2014-11-19 |
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