CA1090145A - Extraction recovery of certain metal values - Google Patents
Extraction recovery of certain metal valuesInfo
- Publication number
- CA1090145A CA1090145A CA269,392A CA269392A CA1090145A CA 1090145 A CA1090145 A CA 1090145A CA 269392 A CA269392 A CA 269392A CA 1090145 A CA1090145 A CA 1090145A
- Authority
- CA
- Canada
- Prior art keywords
- quinoline
- radical
- sulfonamido
- aqueous
- organic
- 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
Links
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 129
- 239000002184 metal Substances 0.000 title claims abstract description 129
- 238000000605 extraction Methods 0.000 title abstract description 35
- 238000011084 recovery Methods 0.000 title abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 261
- 230000008569 process Effects 0.000 claims abstract description 170
- 239000000243 solution Substances 0.000 claims abstract description 169
- 239000012074 organic phase Substances 0.000 claims abstract description 38
- 239000007864 aqueous solution Substances 0.000 claims abstract description 37
- 239000003960 organic solvent Substances 0.000 claims abstract description 28
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 64
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 57
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 37
- -1 8-sulfonamidoquinoline compound Chemical class 0.000 claims description 32
- 239000008346 aqueous phase Substances 0.000 claims description 29
- 239000012071 phase Substances 0.000 claims description 29
- ZTYZEUXZHGOXRT-UHFFFAOYSA-N quinoline-8-sulfonamide Chemical compound C1=CN=C2C(S(=O)(=O)N)=CC=CC2=C1 ZTYZEUXZHGOXRT-UHFFFAOYSA-N 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000001931 aliphatic group Chemical group 0.000 claims description 16
- 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 claims description 13
- 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 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- RKWWUDKRZZVTCL-UHFFFAOYSA-N 2-dodecyl-n-quinolin-8-ylbenzenesulfonamide Chemical group CCCCCCCCCCCCC1=CC=CC=C1S(=O)(=O)NC1=CC=CC2=CC=CN=C12 RKWWUDKRZZVTCL-UHFFFAOYSA-N 0.000 claims description 8
- PRFAIMQIYQPUJX-UHFFFAOYSA-N n-decyl-4-methyl-n-quinolin-8-ylbenzenesulfonamide Chemical group C=1C=CC2=CC=CN=C2C=1N(CCCCCCCCCC)S(=O)(=O)C1=CC=C(C)C=C1 PRFAIMQIYQPUJX-UHFFFAOYSA-N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 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 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 150000003248 quinolines Chemical class 0.000 claims description 5
- ANWFGDZYSQXUMF-UHFFFAOYSA-N 2-dodecyl-n-(2-methylquinolin-8-yl)benzenesulfonamide Chemical group CCCCCCCCCCCCC1=CC=CC=C1S(=O)(=O)NC1=CC=CC2=CC=C(C)N=C12 ANWFGDZYSQXUMF-UHFFFAOYSA-N 0.000 claims description 4
- CXWCOIRQYGVCTG-UHFFFAOYSA-N 3-decyl-2-methyl-n-(2-methylquinolin-8-yl)benzenesulfonamide Chemical group CCCCCCCCCCC1=CC=CC(S(=O)(=O)NC=2C3=NC(C)=CC=C3C=CC=2)=C1C CXWCOIRQYGVCTG-UHFFFAOYSA-N 0.000 claims description 4
- FOSFSMIAZOSABN-UHFFFAOYSA-N 3-decyl-2-methyl-n-(5-nitroquinolin-8-yl)benzenesulfonamide Chemical group CCCCCCCCCCC1=CC=CC(S(=O)(=O)NC=2C3=NC=CC=C3C([N+]([O-])=O)=CC=2)=C1C FOSFSMIAZOSABN-UHFFFAOYSA-N 0.000 claims description 4
- WVKGCLFHZAXTFI-UHFFFAOYSA-N 8-methyl-n-quinolin-8-ylnonane-1-sulfonamide Chemical group C1=CN=C2C(NS(=O)(=O)CCCCCCCC(C)C)=CC=CC2=C1 WVKGCLFHZAXTFI-UHFFFAOYSA-N 0.000 claims description 4
- 150000004696 coordination complex Chemical class 0.000 claims description 4
- DMQGXBPLNNMXNC-UHFFFAOYSA-N n-quinolin-8-ylhexadecane-1-sulfonamide Chemical group C1=CN=C2C(NS(=O)(=O)CCCCCCCCCCCCCCCC)=CC=CC2=C1 DMQGXBPLNNMXNC-UHFFFAOYSA-N 0.000 claims 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 claims description 4
- WYBMEDFVNAKVBK-UHFFFAOYSA-N 2,3-di(nonyl)-n-quinolin-8-ylnaphthalene-1-sulfonamide Chemical group C1=CN=C2C(NS(=O)(=O)C=3C4=CC=CC=C4C=C(C=3CCCCCCCCC)CCCCCCCCC)=CC=CC2=C1 WYBMEDFVNAKVBK-UHFFFAOYSA-N 0.000 claims description 3
- XXNXDMVQKXYUSP-UHFFFAOYSA-N 2,3-dipentyl-n-quinolin-8-ylbenzenesulfonamide Chemical group CCCCCC1=CC=CC(S(=O)(=O)NC=2C3=NC=CC=C3C=CC=2)=C1CCCCC XXNXDMVQKXYUSP-UHFFFAOYSA-N 0.000 claims description 3
- GWPKDHFUKZZDQS-UHFFFAOYSA-N 2-ethyl-n-quinolin-8-ylhexane-1-sulfonamide Chemical group C1=CN=C2C(NS(=O)(=O)CC(CC)CCCC)=CC=CC2=C1 GWPKDHFUKZZDQS-UHFFFAOYSA-N 0.000 claims description 3
- JFORKWRJJAUWHL-UHFFFAOYSA-N 2-heptyl-n-quinolin-8-ylbenzenesulfonamide Chemical group CCCCCCCC1=CC=CC=C1S(=O)(=O)NC1=CC=CC2=CC=CN=C12 JFORKWRJJAUWHL-UHFFFAOYSA-N 0.000 claims description 3
- WEKUBFYVXQDSKC-UHFFFAOYSA-N 2-methyl-3-nonyl-n-quinolin-8-ylbenzenesulfonamide Chemical group CCCCCCCCCC1=CC=CC(S(=O)(=O)NC=2C3=NC=CC=C3C=CC=2)=C1C WEKUBFYVXQDSKC-UHFFFAOYSA-N 0.000 claims description 3
- CRANWSRVQBOUKQ-UHFFFAOYSA-N 3-decyl-2-methyl-n-(6-methylquinolin-8-yl)benzenesulfonamide Chemical group CCCCCCCCCCC1=CC=CC(S(=O)(=O)NC=2C3=NC=CC=C3C=C(C)C=2)=C1C CRANWSRVQBOUKQ-UHFFFAOYSA-N 0.000 claims description 3
- XLNZSJLXNSKFTA-UHFFFAOYSA-N 3-decyl-2-propan-2-yl-n-quinolin-8-ylbenzenesulfonamide Chemical group CCCCCCCCCCC1=CC=CC(S(=O)(=O)NC=2C3=NC=CC=C3C=CC=2)=C1C(C)C XLNZSJLXNSKFTA-UHFFFAOYSA-N 0.000 claims description 3
- NSRGRPJQPVOXBH-UHFFFAOYSA-N 3-decyl-n-(5,7-dichloroquinolin-8-yl)-2-methylbenzenesulfonamide Chemical group CCCCCCCCCCC1=CC=CC(S(=O)(=O)NC=2C3=NC=CC=C3C(Cl)=CC=2Cl)=C1C NSRGRPJQPVOXBH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- IXCLMEVDFRMWTE-UHFFFAOYSA-N 1-phenyl-n-quinolin-8-yltridecane-1-sulfonamide Chemical group C=1C=CC2=CC=CN=C2C=1NS(=O)(=O)C(CCCCCCCCCCCC)C1=CC=CC=C1 IXCLMEVDFRMWTE-UHFFFAOYSA-N 0.000 claims description 2
- FTVVWDGOAFUJEM-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)-n-quinolin-8-ylbenzenesulfonamide Chemical group CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1S(=O)(=O)NC1=CC=CC2=CC=CN=C12 FTVVWDGOAFUJEM-UHFFFAOYSA-N 0.000 claims description 2
- VHBQECOYMQAYPZ-UHFFFAOYSA-N 2-hexadecyl-n-quinolin-8-ylbenzenesulfonamide Chemical group CCCCCCCCCCCCCCCCC1=CC=CC=C1S(=O)(=O)NC1=CC=CC2=CC=CN=C12 VHBQECOYMQAYPZ-UHFFFAOYSA-N 0.000 claims description 2
- IYYLWNNPXNDJNY-UHFFFAOYSA-N 2-methyl-3-octyl-n-quinolin-8-ylbenzenesulfonamide Chemical group CCCCCCCCC1=CC=CC(S(=O)(=O)NC=2C3=NC=CC=C3C=CC=2)=C1C IYYLWNNPXNDJNY-UHFFFAOYSA-N 0.000 claims description 2
- CJENOIFWNSBSCE-UHFFFAOYSA-N 3-decyl-2-ethyl-n-quinolin-8-ylbenzenesulfonamide Chemical group CCCCCCCCCCC1=CC=CC(S(=O)(=O)NC=2C3=NC=CC=C3C=CC=2)=C1CC CJENOIFWNSBSCE-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- WGNVQAFGEJYTTB-UHFFFAOYSA-N n-quinolin-8-yloctane-1-sulfonamide Chemical group C1=CN=C2C(NS(=O)(=O)CCCCCCCC)=CC=CC2=C1 WGNVQAFGEJYTTB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- ASUCESVASRQIOW-UHFFFAOYSA-N 3-decyl-n-(6-methoxyquinolin-8-yl)-2-methylbenzenesulfonamide Chemical group CCCCCCCCCCC1=CC=CC(S(=O)(=O)NC=2C3=NC=CC=C3C=C(OC)C=2)=C1C ASUCESVASRQIOW-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 102
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
- 229910001868 water Inorganic materials 0.000 description 60
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 54
- 125000003118 aryl group Chemical group 0.000 description 48
- 239000011541 reaction mixture Substances 0.000 description 44
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 42
- 235000011149 sulphuric acid Nutrition 0.000 description 41
- 238000003756 stirring Methods 0.000 description 31
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 28
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 27
- WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-UHFFFAOYSA-N 0.000 description 24
- 239000003153 chemical reaction reagent Substances 0.000 description 24
- 239000002244 precipitate Substances 0.000 description 23
- 239000003350 kerosene Substances 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 20
- 229940076134 benzene Drugs 0.000 description 19
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 229910052938 sodium sulfate Inorganic materials 0.000 description 17
- 235000011152 sodium sulphate Nutrition 0.000 description 17
- 239000010949 copper Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- 239000011701 zinc Substances 0.000 description 14
- 125000003342 alkenyl group Chemical group 0.000 description 13
- 239000012267 brine Substances 0.000 description 13
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 12
- 238000001556 precipitation Methods 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 150000004996 alkyl benzenes Chemical class 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- 239000007832 Na2SO4 Substances 0.000 description 10
- 150000002739 metals Chemical class 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 125000002877 alkyl aryl group Chemical group 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 238000005342 ion exchange Methods 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000011068 loading method Methods 0.000 description 7
- 229960003010 sodium sulfate Drugs 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 125000005024 alkenyl aryl group Chemical group 0.000 description 6
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 6
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 6
- 235000011130 ammonium sulphate Nutrition 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 229910021645 metal ion Inorganic materials 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- UZSLUYRGXXHEIZ-UHFFFAOYSA-N 3-(3-methyldecyl)benzenesulfonyl chloride Chemical compound CCCCCCCC(C)CCC1=CC=CC(S(Cl)(=O)=O)=C1 UZSLUYRGXXHEIZ-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 5
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000010936 aqueous wash Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000000199 molecular distillation Methods 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- FQYVVSNFPLKMNU-UHFFFAOYSA-N 1,2-dipentylbenzene Chemical compound CCCCCC1=CC=CC=C1CCCCC FQYVVSNFPLKMNU-UHFFFAOYSA-N 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- NVOKZLKGFWNMCD-UHFFFAOYSA-N 1-bromo-8-methylnonane Chemical compound CC(C)CCCCCCCBr NVOKZLKGFWNMCD-UHFFFAOYSA-N 0.000 description 3
- NBINSWOYIKLKGL-UHFFFAOYSA-N 2-dodecylbenzenesulfonyl chloride Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(Cl)(=O)=O NBINSWOYIKLKGL-UHFFFAOYSA-N 0.000 description 3
- JHIAOWGCGNMQKA-UHFFFAOYSA-N 2-methyl-8-quinolinamine Chemical compound C1=CC=C(N)C2=NC(C)=CC=C21 JHIAOWGCGNMQKA-UHFFFAOYSA-N 0.000 description 3
- JWYRVNFQSPOLHQ-UHFFFAOYSA-N 5-nitroquinolin-8-amine Chemical compound C1=CN=C2C(N)=CC=C([N+]([O-])=O)C2=C1 JWYRVNFQSPOLHQ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
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- 230000003000 nontoxic effect Effects 0.000 description 1
- WIVNTNLDTMNDNO-UHFFFAOYSA-N octane-1-sulfonyl chloride Chemical compound CCCCCCCCS(Cl)(=O)=O WIVNTNLDTMNDNO-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229940061319 ovide Drugs 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- LTHAIAJHDPJXLG-UHFFFAOYSA-N pentan-2-ylbenzene Chemical compound CCCC(C)C1=CC=CC=C1 LTHAIAJHDPJXLG-UHFFFAOYSA-N 0.000 description 1
- PWQOZRPSDQKNPW-UHFFFAOYSA-N pentane-1-sulfonyl chloride Chemical compound CCCCCS(Cl)(=O)=O PWQOZRPSDQKNPW-UHFFFAOYSA-N 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- MHTSJSRDFXZFHQ-UHFFFAOYSA-N quinoline-8-thiol Chemical compound C1=CN=C2C(S)=CC=CC2=C1 MHTSJSRDFXZFHQ-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- DHQIJSYTNIUZRY-UHFFFAOYSA-M sodium;2,3-di(nonyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCCCCCCC)C(CCCCCCCCC)=CC2=C1 DHQIJSYTNIUZRY-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
-
- 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
- C22B3/34—Treatment or purification of solutions, e.g. obtained by leaching by liquid-liquid extraction using organic compounds containing sulfur, e.g. sulfonium
-
- 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
- C22B3/364—Quinoline
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Mechanical Engineering (AREA)
- Geochemistry & Mineralogy (AREA)
- Geology (AREA)
- Environmental & Geological Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Metallurgy (AREA)
- Extraction Or Liquid Replacement (AREA)
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Manufacture And Refinement Of Metals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65200476A | 1976-01-26 | 1976-01-26 | |
| US652,004 | 1976-01-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1090145A true CA1090145A (en) | 1980-11-25 |
Family
ID=24615134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA269,392A Expired CA1090145A (en) | 1976-01-26 | 1977-01-10 | Extraction recovery of certain metal values |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5291707A (enExample) |
| BE (1) | BE850716A (enExample) |
| CA (1) | CA1090145A (enExample) |
| ES (1) | ES455326A1 (enExample) |
| FI (1) | FI770233A7 (enExample) |
| FR (1) | FR2357651A1 (enExample) |
| MX (1) | MX148454A (enExample) |
| SU (1) | SU692542A3 (enExample) |
| ZA (1) | ZA77423B (enExample) |
-
1977
- 1977-01-10 CA CA269,392A patent/CA1090145A/en not_active Expired
- 1977-01-25 ZA ZA77423A patent/ZA77423B/xx unknown
- 1977-01-25 FI FI770233A patent/FI770233A7/fi not_active Application Discontinuation
- 1977-01-25 ES ES455326A patent/ES455326A1/es not_active Expired
- 1977-01-25 SU SU772448753A patent/SU692542A3/ru active
- 1977-01-25 FR FR7702003A patent/FR2357651A1/fr active Granted
- 1977-01-25 BE BE174349A patent/BE850716A/xx not_active IP Right Cessation
- 1977-01-26 JP JP690177A patent/JPS5291707A/ja active Pending
- 1977-01-26 MX MX167837A patent/MX148454A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2357651A1 (fr) | 1978-02-03 |
| JPS5291707A (en) | 1977-08-02 |
| SU692542A3 (ru) | 1979-10-15 |
| MX148454A (es) | 1983-04-25 |
| BE850716A (fr) | 1977-07-25 |
| FI770233A7 (enExample) | 1977-07-27 |
| ZA77423B (en) | 1977-11-30 |
| ES455326A1 (es) | 1978-01-16 |
| FR2357651B1 (enExample) | 1980-12-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |