ES2305787T3 - Metodo para extraer impurezas utilizando liquidos ionicos. - Google Patents
Metodo para extraer impurezas utilizando liquidos ionicos. Download PDFInfo
- Publication number
- ES2305787T3 ES2305787T3 ES04740602T ES04740602T ES2305787T3 ES 2305787 T3 ES2305787 T3 ES 2305787T3 ES 04740602 T ES04740602 T ES 04740602T ES 04740602 T ES04740602 T ES 04740602T ES 2305787 T3 ES2305787 T3 ES 2305787T3
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- Spain
- Prior art keywords
- acids
- formula
- alkyl
- methyl
- process according
- 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.)
- Expired - Lifetime
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 21
- 239000012535 impurity Substances 0.000 title claims description 9
- -1 phoshines Chemical class 0.000 claims abstract description 262
- 239000002253 acid Substances 0.000 claims abstract description 25
- 150000001413 amino acids Chemical class 0.000 claims abstract description 9
- 150000002989 phenols Chemical class 0.000 claims abstract description 9
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 7
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 5
- 238000000605 extraction Methods 0.000 claims description 35
- 150000001450 anions Chemical class 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 229930195733 hydrocarbon Natural products 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims description 12
- 150000007942 carboxylates Chemical class 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical class OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 6
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical class OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical class OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 claims description 2
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 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
- 239000004576 sand Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 abstract description 19
- 150000003009 phosphonic acids Chemical class 0.000 abstract description 9
- 150000001298 alcohols Chemical class 0.000 abstract description 8
- 150000003460 sulfonic acids Chemical class 0.000 abstract description 8
- 150000001412 amines Chemical class 0.000 abstract description 7
- 150000002429 hydrazines Chemical class 0.000 abstract description 7
- 150000002443 hydroxylamines Chemical class 0.000 abstract description 7
- 150000002466 imines Chemical class 0.000 abstract description 7
- 150000002923 oximes Chemical class 0.000 abstract description 7
- 150000003455 sulfinic acids Chemical class 0.000 abstract description 6
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 235000011007 phosphoric acid Nutrition 0.000 abstract description 3
- 150000003016 phosphoric acids Chemical class 0.000 abstract description 3
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 abstract description 2
- RYIOLWQRQXDECZ-UHFFFAOYSA-N phosphinous acid Chemical class PO RYIOLWQRQXDECZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 description 26
- 150000003254 radicals Chemical class 0.000 description 17
- 150000003949 imides Chemical class 0.000 description 13
- 150000003003 phosphines Chemical class 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 125000005842 heteroatom Chemical group 0.000 description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 11
- 229910019142 PO4 Inorganic materials 0.000 description 10
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 10
- 235000021317 phosphate Nutrition 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 125000001072 heteroaryl 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 8
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
- 239000007983 Tris buffer Substances 0.000 description 6
- 125000002015 acyclic group Chemical group 0.000 description 6
- 235000013877 carbamide Nutrition 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
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 239000012071 phase Substances 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
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 6
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 6
- 150000003672 ureas Chemical class 0.000 description 6
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 5
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 5
- 150000005208 1,4-dihydroxybenzenes Chemical class 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
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 150000004705 aldimines Chemical class 0.000 description 5
- 150000003863 ammonium salts Chemical class 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 150000002432 hydroperoxides Chemical class 0.000 description 5
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 150000004658 ketimines Chemical class 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
- 239000002904 solvent Substances 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 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
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 108010000020 Platelet Factor 3 Proteins 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000004657 carbamic 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
- 150000002009 diols Chemical class 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
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 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
- 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
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 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
- 239000001301 oxygen Substances 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- 239000010452 phosphate 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
- 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 3
- 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
- 150000001409 amidines Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 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
- 150000001642 boronic acid derivatives Chemical class 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- DWYMPOCYEZONEA-UHFFFAOYSA-L fluoridophosphate Chemical compound [O-]P([O-])(F)=O DWYMPOCYEZONEA-UHFFFAOYSA-L 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
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- UZZYXUGECOQHPU-UHFFFAOYSA-M n-octyl sulfate Chemical compound CCCCCCCCOS([O-])(=O)=O UZZYXUGECOQHPU-UHFFFAOYSA-M 0.000 description 3
- 229940067739 octyl sulfate Drugs 0.000 description 3
- 150000004028 organic sulfates Chemical class 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
- 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 compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- 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
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-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
- LDVVBLGHGCHZBJ-UHFFFAOYSA-N 1-decyl-3-methylimidazolium Chemical compound CCCCCCCCCCN1C=C[N+](C)=C1 LDVVBLGHGCHZBJ-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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
Landscapes
- 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 | 2003-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2305787T3 true ES2305787T3 (es) | 2008-11-01 |
Family
ID=34201370
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04740602T Expired - Lifetime ES2305787T3 (es) | 2003-07-21 | 2004-07-03 | Metodo para extraer impurezas utilizando liquidos ionicos. |
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=) |
Families Citing this family (37)
| 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 |
| WO2006110450A1 (en) * | 2005-04-07 | 2006-10-19 | Matheson Tri-Gas | Fluid storage and purification method and system |
| 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 |
| CN101505844B (zh) * | 2006-08-18 | 2012-07-11 | 因温斯特技术公司 | 萃取方法 |
| WO2008043837A1 (en) | 2006-10-13 | 2008-04-17 | Basf Se | 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 |
| US9005450B2 (en) * | 2007-12-20 | 2015-04-14 | Proionic Production Of Ionic Substances Gmbh & Co Kg | Use of magnetic, ionic liquids as an extraction agent |
| US7956230B2 (en) * | 2007-12-21 | 2011-06-07 | Chevron U.S.A. Inc. | Reduction of organic halide contamination in hydrocarbon products |
| MX2010008667A (es) | 2008-02-11 | 2010-09-24 | Basf Se | Metodo para producir estructuras porosas de polimericos sinteticos. |
| BRPI0908350A2 (pt) * | 2008-02-11 | 2015-10-27 | Basf Se | processos para preparar poliamidas, para funcionalizar poliamidas por transmidação e para produzir fibras, folhas, filmes ou revestimentos a partir de poliamidas |
| KR100958876B1 (ko) * | 2008-04-02 | 2010-05-20 | 삼성엔지니어링 주식회사 | 다양한 극성/비극성 용매 혼화성 이온성 액체 및 그의제조방법 |
| US7812191B2 (en) * | 2008-05-07 | 2010-10-12 | Lyondell Chemical Technology, L.P. | Removing hydrocarbon impurities from acetic acid by ionic liquid extraction |
| CN102046599B (zh) * | 2008-05-26 | 2013-08-21 | 默克专利股份公司 | 具有四氰基硼酸根阴离子的离子液体作为溶剂用于从水溶液中萃取醇的应用 |
| 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 |
| EP2421625B1 (en) | 2009-04-23 | 2016-07-20 | proionic GmbH | Method of dehydrating an ionic liquid |
| DE102010028550A1 (de) | 2009-05-05 | 2010-11-11 | Basf Se | Verfahren zur Herstellung von Eisen-Nanopartikel enthaltenden thermoplastischen Polymerformmassen |
| EP2512614A1 (en) * | 2009-12-15 | 2012-10-24 | Cytec Technology Corp. | Methods and compositions for the removal of impurities from an impurity-loaded ionic liquid |
| EP2468812A1 (de) | 2010-12-21 | 2012-06-27 | Basf Se | Thermoplastische Formmasse |
| EP2468811A1 (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 |
| AU2013225757B2 (en) * | 2012-03-02 | 2018-03-01 | 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 |
| 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 |
| 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 |
| EP3720920B1 (en) | 2017-12-08 | 2024-01-24 | Baker Hughes Holdings 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 |
| CA2426770A1 (en) | 2000-10-26 | 2002-05-02 | Laura C. Boudreau | 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 |
| ATE297368T1 (de) * | 2002-04-18 | 2005-06-15 | Haldor Topsoe As | Kontinuierliches verfahren zur trennung von wasser von einer kohlenwasserstoffbeschickung |
-
2004
- 2004-07-03 KR KR1020067001406A patent/KR20060076269A/ko not_active Withdrawn
- 2004-07-03 US US10/565,187 patent/US7605297B2/en not_active Expired - Fee Related
- 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 WO PCT/EP2004/007254 patent/WO2005019137A1/de not_active Ceased
- 2004-07-03 JP JP2006520705A patent/JP2006528599A/ja not_active Withdrawn
- 2004-07-03 ES ES04740602T patent/ES2305787T3/es not_active Expired - Lifetime
- 2004-07-03 EP EP04740602A patent/EP1648845B1/de not_active Expired - Lifetime
- 2004-07-03 DE DE502004007160T patent/DE502004007160D1/de not_active Expired - Lifetime
- 2004-07-03 AT AT04740602T patent/ATE395316T1/de active
-
2005
- 2005-12-22 IL IL172780A patent/IL172780A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005019137A8 (de) | 2005-06-16 |
| JP2006528599A (ja) | 2006-12-21 |
| CN100381406C (zh) | 2008-04-16 |
| KR20060076269A (ko) | 2006-07-04 |
| US7605297B2 (en) | 2009-10-20 |
| CN1826302A (zh) | 2006-08-30 |
| DK1648845T3 (da) | 2008-09-01 |
| EP1648845B1 (de) | 2008-05-14 |
| ATE395316T1 (de) | 2008-05-15 |
| WO2005019137A1 (de) | 2005-03-03 |
| DE502004007160D1 (de) | 2008-06-26 |
| IL172780A0 (en) | 2006-04-10 |
| US20070193952A1 (en) | 2007-08-23 |
| EP1648845A1 (de) | 2006-04-26 |
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