JPH0379411B2 - - Google Patents
Info
- Publication number
- JPH0379411B2 JPH0379411B2 JP61038962A JP3896286A JPH0379411B2 JP H0379411 B2 JPH0379411 B2 JP H0379411B2 JP 61038962 A JP61038962 A JP 61038962A JP 3896286 A JP3896286 A JP 3896286A JP H0379411 B2 JPH0379411 B2 JP H0379411B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- substituted
- group
- benzene ring
- extractant
- 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
Links
- 239000000243 solution Substances 0.000 claims abstract description 42
- 229910052751 metal Inorganic materials 0.000 claims abstract description 32
- 239000002184 metal Substances 0.000 claims abstract description 32
- -1 pseudohalide anion Chemical class 0.000 claims abstract description 24
- 239000007864 aqueous solution Substances 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 24
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- ROGGGUFLPOUJJU-UHFFFAOYSA-N 16-methylheptadecyl 2-[1-(16-methylheptadecoxycarbonyl)benzimidazol-2-yl]benzimidazole-1-carboxylate Chemical group C1=CC=C2N(C(=O)OCCCCCCCCCCCCCCCC(C)C)C(C=3N(C4=CC=CC=C4N=3)C(=O)OCCCCCCCCCCCCCCCC(C)C)=NC2=C1 ROGGGUFLPOUJJU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 150000003138 primary alcohols Chemical class 0.000 claims description 3
- DTAZYILZXNGHDS-UHFFFAOYSA-N 8-methylnonyl 2-[1-(8-methylnonoxycarbonyl)benzimidazol-2-yl]benzimidazole-1-carboxylate Chemical group C1=CC=C2N(C(=O)OCCCCCCCC(C)C)C(C=3N(C4=CC=CC=C4N=3)C(=O)OCCCCCCCC(C)C)=NC2=C1 DTAZYILZXNGHDS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract description 65
- 229910052725 zinc Inorganic materials 0.000 abstract description 65
- 239000011701 zinc Substances 0.000 abstract description 65
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 36
- 229910052802 copper Inorganic materials 0.000 abstract description 36
- 239000010949 copper Substances 0.000 abstract description 36
- 238000000638 solvent extraction Methods 0.000 abstract description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 8
- VEZJRJGLFIXQHG-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)-1h-benzimidazole Chemical class C1=CC=C2NC(C=3NC4=CC=CC=C4N=3)=NC2=C1 VEZJRJGLFIXQHG-UHFFFAOYSA-N 0.000 abstract description 6
- HVEHTNLSYGZELD-UHFFFAOYSA-N 2,2'-biimidazole Chemical class N1=CC=NC1=C1N=CC=N1 HVEHTNLSYGZELD-UHFFFAOYSA-N 0.000 abstract description 4
- 150000004820 halides Chemical class 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 239000012074 organic phase Substances 0.000 description 14
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 13
- 238000002386 leaching Methods 0.000 description 12
- 238000000605 extraction Methods 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 description 10
- 239000011707 mineral Substances 0.000 description 10
- 235000010755 mineral Nutrition 0.000 description 10
- 238000011084 recovery Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- 238000005363 electrowinning Methods 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000011592 zinc chloride Substances 0.000 description 7
- 235000005074 zinc chloride Nutrition 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 6
- 238000013508 migration Methods 0.000 description 6
- 230000005012 migration Effects 0.000 description 6
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- RLDVFPKFKUYGHR-UHFFFAOYSA-N tridecyl carbonochloridate Chemical compound CCCCCCCCCCCCCOC(Cl)=O RLDVFPKFKUYGHR-UHFFFAOYSA-N 0.000 description 4
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001555 benzenes Chemical group 0.000 description 3
- 229960002713 calcium chloride Drugs 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 230000005588 protonation Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- KXNUGWMDNZBQGV-UHFFFAOYSA-N 16-methylheptadecyl carbonochloridate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(Cl)=O KXNUGWMDNZBQGV-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical class ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000005882 aldol condensation reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- LLSDKQJKOVVTOJ-UHFFFAOYSA-L calcium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ca+2] LLSDKQJKOVVTOJ-UHFFFAOYSA-L 0.000 description 2
- 229940052299 calcium chloride dihydrate Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- SEGLCEQVOFDUPX-UHFFFAOYSA-N di-(2-ethylhexyl)phosphoric acid Chemical compound CCCCC(CC)COP(O)(=O)OCC(CC)CCCC SEGLCEQVOFDUPX-UHFFFAOYSA-N 0.000 description 2
- 239000008151 electrolyte solution Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000012527 feed solution Substances 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 238000009854 hydrometallurgy Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000002577 pseudohalo group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- VRXFCUXLPCIOAE-UHFFFAOYSA-N 2,2,2-trichloro-n-methylacetamide Chemical compound CNC(=O)C(Cl)(Cl)Cl VRXFCUXLPCIOAE-UHFFFAOYSA-N 0.000 description 1
- FYEWLNDAMUOKTG-UHFFFAOYSA-N 2-(1H-imidazol-2-yl)-1H-benzimidazole Chemical class C1=CNC(C=2NC3=CC=CC=C3N=2)=N1 FYEWLNDAMUOKTG-UHFFFAOYSA-N 0.000 description 1
- XULHFMYCBKQGEE-UHFFFAOYSA-N 2-hexyl-1-Decanol Chemical compound CCCCCCCCC(CO)CCCCCC XULHFMYCBKQGEE-UHFFFAOYSA-N 0.000 description 1
- DKHJWGRSTKKDCD-UHFFFAOYSA-N 2-hexyldecyl carbonochloridate Chemical compound CCCCCCCCC(COC(Cl)=O)CCCCCC DKHJWGRSTKKDCD-UHFFFAOYSA-N 0.000 description 1
- AXNUJYHFQHQZBE-UHFFFAOYSA-N 3-methylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N)=C1N AXNUJYHFQHQZBE-UHFFFAOYSA-N 0.000 description 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- QODVMRUUPVKSRY-UHFFFAOYSA-N 8-methylnonyl carbonochloridate Chemical compound CC(C)CCCCCCCOC(Cl)=O QODVMRUUPVKSRY-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- MBMLMWLHJBBADN-UHFFFAOYSA-N Ferrous sulfide Chemical compound [Fe]=S MBMLMWLHJBBADN-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- DRUIESSIVFYOMK-UHFFFAOYSA-N Trichloroacetonitrile Chemical compound ClC(Cl)(Cl)C#N DRUIESSIVFYOMK-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- DVRDHUBQLOKMHZ-UHFFFAOYSA-N chalcopyrite Chemical compound [S-2].[S-2].[Fe+2].[Cu+2] DVRDHUBQLOKMHZ-UHFFFAOYSA-N 0.000 description 1
- 229910052951 chalcopyrite Inorganic materials 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940021013 electrolyte solution Drugs 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 229910001448 ferrous ion Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- OGBINJLTBZWRRB-UHFFFAOYSA-N methyl 2,2,2-trichloroethanimidate Chemical compound COC(=N)C(Cl)(Cl)Cl OGBINJLTBZWRRB-UHFFFAOYSA-N 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 150000002912 oxalic acid derivatives Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- CAYQCXWFSAHNAB-UHFFFAOYSA-N tridecyl 2-(1-tridecoxycarbonylimidazol-2-yl)imidazole-1-carboxylate Chemical compound CCCCCCCCCCCCCOC(=O)N1C=CN=C1C1=NC=CN1C(=O)OCCCCCCCCCCCCC CAYQCXWFSAHNAB-UHFFFAOYSA-N 0.000 description 1
- 150000005199 trimethylbenzenes Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G3/00—Compounds of copper
- C01G3/003—Preparation involving a liquid-liquid extraction, an adsorption or an ion-exchange
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G9/00—Compounds of zinc
- C01G9/003—Preparation involving a liquid-liquid extraction, an adsorption or an ion-exchange
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/20—Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B3/00—Extraction of metal compounds from ores or concentrates by wet processes
- C22B3/20—Treatment or purification of solutions, e.g. obtained by leaching
- C22B3/26—Treatment or purification of solutions, e.g. obtained by leaching by liquid-liquid extraction using organic compounds
- C22B3/36—Heterocyclic compounds
- C22B3/362—Heterocyclic compounds of a single type
-
- 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
- Y02P10/00—Technologies related to metal processing
- Y02P10/20—Recycling
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S423/00—Chemistry of inorganic compounds
- Y10S423/09—Reaction techniques
- Y10S423/14—Ion exchange; chelation or liquid/liquid ion extraction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Geology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- Manufacture And Refinement Of Metals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
- Analysing Materials By The Use Of Radiation (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Exhaust Gas After Treatment (AREA)
- Pressure Welding/Diffusion-Bonding (AREA)
- Measuring Fluid Pressure (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Fire-Detection Mechanisms (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858504819A GB8504819D0 (en) | 1985-02-25 | 1985-02-25 | Extraction of metal values |
| GB8504819 | 1985-02-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61195933A JPS61195933A (ja) | 1986-08-30 |
| JPH0379411B2 true JPH0379411B2 (en, 2012) | 1991-12-18 |
Family
ID=10575040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61038962A Granted JPS61195933A (ja) | 1985-02-25 | 1986-02-24 | 金属有価物抽出方法 |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US4696801A (en, 2012) |
| EP (1) | EP0196153B1 (en, 2012) |
| JP (1) | JPS61195933A (en, 2012) |
| AT (1) | ATE44982T1 (en, 2012) |
| AU (1) | AU587420B2 (en, 2012) |
| BR (1) | BR8600767A (en, 2012) |
| CA (1) | CA1335376C (en, 2012) |
| DE (1) | DE3664643D1 (en, 2012) |
| ES (1) | ES8800669A1 (en, 2012) |
| FI (1) | FI81123C (en, 2012) |
| GB (2) | GB8504819D0 (en, 2012) |
| IE (1) | IE58979B1 (en, 2012) |
| MX (1) | MX170592B (en, 2012) |
| NO (1) | NO167046C (en, 2012) |
| NZ (1) | NZ215082A (en, 2012) |
| PH (1) | PH22685A (en, 2012) |
| PL (1) | PL144949B1 (en, 2012) |
| PT (1) | PT82075B (en, 2012) |
| ZA (1) | ZA861005B (en, 2012) |
| ZM (1) | ZM2586A1 (en, 2012) |
| ZW (1) | ZW3786A1 (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8707798D0 (en) * | 1987-04-01 | 1987-05-07 | Ici Plc | Recovery of metals |
| US5478539A (en) * | 1981-07-22 | 1995-12-26 | Zeneca Limited | Process for the recovery of metals |
| GB8504819D0 (en) * | 1985-02-25 | 1985-03-27 | Ici Plc | Extraction of metal values |
| FR2607021B1 (fr) * | 1986-11-21 | 1990-11-16 | Commissariat Energie Atomique | Procede d'extraction selective de metaux de transition a partir de solutions acides par des systemes de ligands azotes polydentes et d'echangeurs cationiques |
| CA1303815C (en) * | 1987-06-30 | 1992-06-23 | Solex Research Corporation Of Japan | Method for neutralization treatment of sulfuric acid containing iron ions |
| US5089592A (en) * | 1988-06-09 | 1992-02-18 | The Dow Chemical Company | Biscyclobutarene monomer comprising two cyclobutarene moieties bridged by a divalent radical comprising at least one benzothiazole or benzimidazole linkage |
| US5196095A (en) * | 1990-04-03 | 1993-03-23 | Henkel Corporation | Process for recovering a metal from an aqueous solution comprising a mixture of metal chlorides |
| GB9104395D0 (en) * | 1991-03-01 | 1991-04-17 | Ici Plc | Compound,preparation and use for metal extraction |
| US5110354A (en) * | 1991-04-19 | 1992-05-05 | Hull Harold L | Closed loop copper cell extraction process |
| US5484470A (en) * | 1994-07-28 | 1996-01-16 | E. I. Du Pont De Nemours And Company | Enhancement of gold lixiviation using nitrogen and sulfur heterocyclic aromatic compounds |
| ES2162718A1 (es) | 1998-07-29 | 2002-01-01 | Const Aeronauticas Sa | Un sistema de proteccion contra descargas electricas, especialmente rayos, de componentes estructurales de aviones. |
| ES2163951B1 (es) | 1998-07-29 | 2003-05-16 | Airbus Espana Sl | Un sistema de proteccion contra descargas electricas, especialmente rayos, de componentes estructurales de aviones. |
| CA2539575C (en) * | 2003-11-20 | 2015-01-20 | Boehringer Ingelheim International Gmbh | Method of removing transition metals, especially from metathesis reaction products |
| JP7220904B2 (ja) * | 2018-03-07 | 2023-02-13 | 国立研究開発法人量子科学技術研究開発機構 | グルカミン誘導体、グルカミン誘導体からなる金属吸着剤、グルカミン誘導体からなる金属吸着剤を備える金属抽出装置、金属抽出キット |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA716684B (en) * | 1970-10-08 | 1973-05-30 | Erba Carlo Spa | Substituted 2,2'-biimidazoles and process for their preparation |
| US3843667A (en) * | 1973-09-12 | 1974-10-22 | M Cupery | N-imidazole compounds and their complex metal derivatives |
| GB1504894A (en) * | 1975-06-09 | 1978-03-22 | Ici Ltd | Process for the extraction of metal values from aqueous solutions of metal salts |
| ZA775398B (en) * | 1977-09-07 | 1979-04-25 | Nat Inst Metallurg | Selective ion exchange media |
| US4581220A (en) * | 1982-11-04 | 1986-04-08 | Imperial Chemical Industries, Plc | Process for the extraction of metal values and novel metal extractants |
| GB8318412D0 (en) * | 1983-07-07 | 1983-08-10 | Ici Plc | Extraction of metal values |
| GB8504819D0 (en) * | 1985-02-25 | 1985-03-27 | Ici Plc | Extraction of metal values |
-
1985
- 1985-02-25 GB GB858504819A patent/GB8504819D0/en active Pending
-
1986
- 1986-02-05 EP EP86300763A patent/EP0196153B1/en not_active Expired
- 1986-02-05 GB GB868602800A patent/GB8602800D0/en active Pending
- 1986-02-05 DE DE8686300763T patent/DE3664643D1/de not_active Expired
- 1986-02-05 AT AT86300763T patent/ATE44982T1/de not_active IP Right Cessation
- 1986-02-10 NZ NZ215082A patent/NZ215082A/en unknown
- 1986-02-11 IE IE38386A patent/IE58979B1/en not_active IP Right Cessation
- 1986-02-11 ZA ZA861005A patent/ZA861005B/xx unknown
- 1986-02-12 US US06/828,748 patent/US4696801A/en not_active Expired - Lifetime
- 1986-02-12 AU AU53409/86A patent/AU587420B2/en not_active Ceased
- 1986-02-14 CA CA000501959A patent/CA1335376C/en not_active Expired - Fee Related
- 1986-02-17 ZW ZW37/86A patent/ZW3786A1/xx unknown
- 1986-02-17 ZM ZM25/86A patent/ZM2586A1/xx unknown
- 1986-02-19 PH PH33435A patent/PH22685A/en unknown
- 1986-02-20 MX MX001608A patent/MX170592B/es unknown
- 1986-02-20 PL PL1986258039A patent/PL144949B1/pl unknown
- 1986-02-24 PT PT82075A patent/PT82075B/pt unknown
- 1986-02-24 NO NO860675A patent/NO167046C/no unknown
- 1986-02-24 BR BR8600767A patent/BR8600767A/pt not_active IP Right Cessation
- 1986-02-24 JP JP61038962A patent/JPS61195933A/ja active Granted
- 1986-02-25 FI FI860810A patent/FI81123C/fi not_active IP Right Cessation
- 1986-02-25 ES ES552394A patent/ES8800669A1/es not_active Expired
-
1987
- 1987-07-20 US US07/075,846 patent/US4822880A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61195933A (ja) | 1986-08-30 |
| ZM2586A1 (en) | 1986-07-28 |
| PL144949B1 (en) | 1988-07-30 |
| FI81123C (fi) | 1990-09-10 |
| IE58979B1 (en) | 1993-12-15 |
| MX170592B (es) | 1993-09-01 |
| ES8800669A1 (es) | 1987-11-16 |
| FI81123B (fi) | 1990-05-31 |
| US4822880A (en) | 1989-04-18 |
| FI860810A0 (fi) | 1986-02-25 |
| NO167046C (no) | 1991-09-25 |
| ES552394A0 (es) | 1987-11-16 |
| ZA861005B (en) | 1986-10-29 |
| EP0196153A2 (en) | 1986-10-01 |
| GB8504819D0 (en) | 1985-03-27 |
| PL258039A1 (en) | 1987-04-21 |
| NZ215082A (en) | 1988-08-30 |
| ATE44982T1 (de) | 1989-08-15 |
| AU5340986A (en) | 1986-08-28 |
| GB8602800D0 (en) | 1986-03-12 |
| PH22685A (en) | 1988-11-14 |
| EP0196153A3 (en) | 1986-12-30 |
| NO167046B (no) | 1991-06-17 |
| IE860383L (en) | 1986-08-25 |
| FI860810L (fi) | 1986-08-26 |
| AU587420B2 (en) | 1989-08-17 |
| PT82075A (en) | 1986-03-01 |
| NO860675L (no) | 1986-08-26 |
| DE3664643D1 (en) | 1989-08-31 |
| EP0196153B1 (en) | 1989-07-26 |
| CA1335376C (en) | 1995-04-25 |
| US4696801A (en) | 1987-09-29 |
| BR8600767A (pt) | 1986-11-04 |
| PT82075B (pt) | 1988-07-01 |
| ZW3786A1 (en) | 1987-09-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |