CA1093537A - Oximes et procede d'extraction de composes de cuivre en solution aqueuse - Google Patents

Oximes et procede d'extraction de composes de cuivre en solution aqueuse

Info

Publication number: CA1093537A
Authority: CA; Canada
Prior art keywords: mixture; alkyl; dioxime; group; groups
Prior art date: 1976-12-09
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

Application number

CA289,434A

Other languages

English (en)

Inventor

Peter Koenders

Riekert Kok

Abraham J. Van Der Zeeuw

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell Canada Ltd

Original Assignee

Shell Canada Ltd

Priority date (The priority date 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 date listed.)

1976-12-09

Filing date

1977-10-25

Publication date

1981-01-13

1977-10-25 Application filed by Shell Canada Ltd filed Critical Shell Canada Ltd

1981-01-13 Application granted granted Critical

1981-01-13 Publication of CA1093537A publication Critical patent/CA1093537A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 33
239000010949 copper Substances 0.000 title claims abstract description 27
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims abstract description 24
229910052802 copper Inorganic materials 0.000 title claims abstract description 24
239000007864 aqueous solution Substances 0.000 title claims abstract description 20
238000000926 separation method Methods 0.000 title claims abstract description 7
150000002923 oximes Chemical class 0.000 title claims description 15
239000000203 mixture Substances 0.000 claims abstract description 95
230000002378 acidificating effect Effects 0.000 claims abstract description 13
239000003960 organic solvent Substances 0.000 claims abstract description 10
238000000638 solvent extraction Methods 0.000 claims abstract description 5
238000000622 liquid--liquid extraction Methods 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 49
125000004432 carbon atom Chemical group C* 0.000 claims description 39
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
125000003118 aryl group Chemical group 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 15
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 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
230000029936 alkylation Effects 0.000 claims description 10
238000005804 alkylation reaction Methods 0.000 claims description 10
125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
239000012169 petroleum derived wax Substances 0.000 claims description 4
235000019381 petroleum wax Nutrition 0.000 claims description 4
238000004227 thermal cracking Methods 0.000 claims description 4
HRGVKYYMAZJEGB-UHFFFAOYSA-N N-(9-hydroxyiminohexadecan-8-ylidene)hydroxylamine Chemical group CCCCCCCC(C(CCCCCCC)=NO)=NO HRGVKYYMAZJEGB-UHFFFAOYSA-N 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
229910052742 iron Inorganic materials 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000000962 organic group Chemical group 0.000 claims description 2
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
229960003742 phenol Drugs 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
238000000605 extraction Methods 0.000 description 19
150000001875 compounds Chemical class 0.000 description 17
238000002474 experimental method Methods 0.000 description 17
239000000243 solution Substances 0.000 description 17
-1 aliphatic oximes Chemical class 0.000 description 11
238000003756 stirring Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
150000001721 carbon Chemical group 0.000 description 7
230000000052 comparative effect Effects 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000010410 layer Substances 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
125000004429 atom Chemical group 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
WXJZPOXTTCENPW-UHFFFAOYSA-N 1-(4-dodecylnaphthalen-1-yl)propan-1-one Chemical compound C1=CC=C2C(CCCCCCCCCCCC)=CC=C(C(=O)CC)C2=C1 WXJZPOXTTCENPW-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
125000005418 aryl aryl group Chemical group 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
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 3
239000003350 kerosene Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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 3
VVKQBWYLJBJNST-UHFFFAOYSA-N 1-(4-dodecylnaphthalen-1-yl)-2-hydroxyiminopropan-1-one Chemical compound C1=CC=C2C(CCCCCCCCCCCC)=CC=C(C(=O)C(C)=NO)C2=C1 VVKQBWYLJBJNST-UHFFFAOYSA-N 0.000 description 2
YCBRZJYZKWMUBG-UHFFFAOYSA-N 2-(C-benzyl-N-hydroxycarbonimidoyl)-4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C(C(CC=2C=CC=CC=2)=NO)=C1 YCBRZJYZKWMUBG-UHFFFAOYSA-N 0.000 description 2
CROPCLKVTSNPEY-UHFFFAOYSA-N 2-(N-hydroxy-C-phenylcarbonimidoyl)-4-nonylphenol Chemical class CCCCCCCCCC1=CC=C(O)C(C(=NO)C=2C=CC=CC=2)=C1 CROPCLKVTSNPEY-UHFFFAOYSA-N 0.000 description 2
HZXQKZWVTDAZAE-UHFFFAOYSA-N 2-(N-hydroxy-C-phenylcarbonimidoyl)phenol Chemical class C=1C=CC=C(O)C=1C(=NO)C1=CC=CC=C1 HZXQKZWVTDAZAE-UHFFFAOYSA-N 0.000 description 2
PRRPUEWAMYRKPC-UHFFFAOYSA-N 2-hydroxyiminoacetaldehyde Chemical class ON=CC=O PRRPUEWAMYRKPC-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
OJLHELDDZKBRFL-UHFFFAOYSA-N N-[1-(4-dodecylnaphthalen-1-yl)-1-hydroxyiminopropan-2-ylidene]hydroxylamine Chemical compound C(CCCCCCCCCCC)C1=CC=C(C2=CC=CC=C12)C(C(C)=NO)=NO OJLHELDDZKBRFL-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
230000002152 alkylating effect Effects 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
125000004104 aryloxy group Chemical group 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
125000001421 myristyl 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])[H] 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
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 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
239000002243 precursor Substances 0.000 description 2
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 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
229920006395 saturated elastomer Polymers 0.000 description 2
239000011343 solid material Substances 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
239000001117 sulphuric acid Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
238000005406 washing Methods 0.000 description 2
VTWKXBJHBHYJBI-SOFGYWHQSA-N (ne)-n-benzylidenehydroxylamine Chemical compound O\N=C\C1=CC=CC=C1 VTWKXBJHBHYJBI-SOFGYWHQSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
NPSQMCNZRDJFEM-UHFFFAOYSA-N 2-(hydroxyiminomethyl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C=NO)=C(O)C(C(C)(C)CC)=C1 NPSQMCNZRDJFEM-UHFFFAOYSA-N 0.000 description 1
ORIHZIZPTZTNCU-VMPITWQZSA-N 2-[(E)-hydroxyiminomethyl]phenol Chemical compound O\N=C\C1=CC=CC=C1O ORIHZIZPTZTNCU-VMPITWQZSA-N 0.000 description 1
MIZWKBYZJRWHIC-UHFFFAOYSA-N 2-hydroxyimino-4-propyldodecan-3-one Chemical compound CCCC(CCCCCCCC)C(C(C)=NO)=O MIZWKBYZJRWHIC-UHFFFAOYSA-N 0.000 description 1
NXZLTPQEYLXQCH-UHFFFAOYSA-N 2-hydroxyiminoacetamide Chemical class NC(=O)C=NO NXZLTPQEYLXQCH-UHFFFAOYSA-N 0.000 description 1
PDQYOPNIPOWAFS-UHFFFAOYSA-N 2-hydroxyiminopropanal Chemical class O=CC(C)=NO PDQYOPNIPOWAFS-UHFFFAOYSA-N 0.000 description 1
SESFQRDUAZRWAW-UHFFFAOYSA-N 2-hydroxyiminopropane-1,3-diol Chemical class OCC(CO)=NO SESFQRDUAZRWAW-UHFFFAOYSA-N 0.000 description 1
UWGTVLYQSJNUFP-CAPFRKAQSA-N 4-dodecyl-2-[(E)-hydroxyiminomethyl]phenol Chemical compound [H]\C(=N/O)C1=CC(CCCCCCCCCCCC)=CC=C1O UWGTVLYQSJNUFP-CAPFRKAQSA-N 0.000 description 1
JPVAJIHITBSSAM-UHFFFAOYSA-N 4-tert-butyl-2-(hydroxyiminomethyl)phenol Chemical compound CC(C)(C)C1=CC=C(O)C(C=NO)=C1 JPVAJIHITBSSAM-UHFFFAOYSA-N 0.000 description 1
SLCANKHLTWZHRV-UHFFFAOYSA-N 5,8-diethyl-7-hydroxyiminododecan-6-ol Chemical compound CCCCC(CC)C(O)C(=NO)C(CC)CCCC SLCANKHLTWZHRV-UHFFFAOYSA-N 0.000 description 1
ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
DHCPJFGMGUUQSF-UHFFFAOYSA-N N-(2-hydroxyimino-4-nonylcyclohexylidene)hydroxylamine Chemical class C(CCCCCCCC)C1CC(C(CC1)=NO)=NO DHCPJFGMGUUQSF-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
150000008062 acetophenones Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
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 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
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 1
238000009835 boiling Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
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 1
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 1
238000005868 electrolysis reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
LJHFIVQEAFAURQ-UHFFFAOYSA-N glyoxime Chemical class ON=CC=NO LJHFIVQEAFAURQ-UHFFFAOYSA-N 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
NXPHCVPFHOVZBC-UHFFFAOYSA-N hydroxylamine;sulfuric acid Chemical compound ON.OS(O)(=O)=O NXPHCVPFHOVZBC-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
SKRDXYBATCVEMS-UHFFFAOYSA-N isopropyl nitrite Chemical compound CC(C)ON=O SKRDXYBATCVEMS-UHFFFAOYSA-N 0.000 description 1
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 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
238000006146 oximation reaction Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- 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
- C22B3/30—Oximes
- 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)
Materials Engineering (AREA)
Geology (AREA)
Geochemistry & Mineralogy (AREA)
Manufacturing & Machinery (AREA)
General Life Sciences & Earth Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Mechanical Engineering (AREA)
Metallurgy (AREA)
Environmental & Geological Engineering (AREA)
Inorganic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Extraction Or Liquid Replacement (AREA)
Manufacture And Refinement Of Metals (AREA)

CA289,434A 1976-12-09 1977-10-25 Oximes et procede d'extraction de composes de cuivre en solution aqueuse Expired CA1093537A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB51470/76A GB1580799A (en)	1976-12-09	1976-12-09	Process for the preparation of copper values from aqueous solutions
GB51470/76		1976-12-09

Publications (1)

Publication Number	Publication Date
CA1093537A true CA1093537A (fr)	1981-01-13

Family

ID=10460150

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA289,434A Expired CA1093537A (fr)	1976-12-09	1977-10-25	Oximes et procede d'extraction de composes de cuivre en solution aqueuse

Country Status (12)

Country	Link
JP (1)	JPS5371695A (fr)
AU (1)	AU516884B2 (fr)
BE (1)	BE861592A (fr)
CA (1)	CA1093537A (fr)
DE (1)	DE2754539A1 (fr)
ES (1)	ES464827A1 (fr)
GB (1)	GB1580799A (fr)
PL (1)	PL108918B1 (fr)
SU (1)	SU731906A3 (fr)
YU (1)	YU40315B (fr)
ZA (1)	ZA777301B (fr)
ZM (1)	ZM8477A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4339348A (en)	1979-02-09	1982-07-13	Kennecott Corporation	Dioxime ion exchangers
US4301124A (en)	1979-02-09	1981-11-17	Kennecott Corporation	Cobalt solvent extraction with dioxime ion exchangers
US4248837A (en) *	1979-02-09	1981-02-03	Kennecott Copper Corporation	Solvent extraction of copper, nickel with methyl hexyl dioxime
US4855114A (en) *	1988-09-30	1989-08-08	Sherex Chemical Company, Inc.	Dioxime kinetic enhancer for solvent extraction of gallium from basic aqueous solutions thereof
RU2155818C1 (ru) *	1999-10-06	2000-09-10	Воропанова Лидия Алексеевна	Способ экстракции меди из водных растворов
ES2291105B1 (es) *	2004-04-08	2009-02-16	Cognis Corporation	Configuracion en paralelo de series entrelazadas para plantas de extraccion de metales con disolventes.

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1793468C3 (de) *	1968-09-21	1980-01-10	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von a -Oxlminoalkylketonen
GB1537828A (en) *	1975-03-26	1979-01-04	Shell Int Research	Extraction of copper values from aqueous solutions with hydroxy-oximes

1976
- 1976-12-09 GB GB51470/76A patent/GB1580799A/en not_active Expired
1977
- 1977-10-25 CA CA289,434A patent/CA1093537A/fr not_active Expired
- 1977-11-21 ZM ZM8477A patent/ZM8477A1/xx unknown
- 1977-12-06 YU YU2869/77A patent/YU40315B/xx unknown
- 1977-12-07 AU AU31296/77A patent/AU516884B2/en not_active Expired
- 1977-12-07 PL PL1977202702A patent/PL108918B1/pl unknown
- 1977-12-07 JP JP14621277A patent/JPS5371695A/ja active Pending
- 1977-12-07 ES ES464827A patent/ES464827A1/es not_active Expired
- 1977-12-07 ZA ZA00777301A patent/ZA777301B/xx unknown
- 1977-12-07 SU SU772553702A patent/SU731906A3/ru active
- 1977-12-07 DE DE19772754539 patent/DE2754539A1/de not_active Withdrawn
- 1977-12-07 BE BE183242A patent/BE861592A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
ZA777301B (en)	1978-10-25
ES464827A1 (es)	1978-07-16
YU40315B (en)	1985-12-31
BE861592A (fr)	1978-06-07
AU3129677A (en)	1979-06-14
JPS5371695A (en)	1978-06-26
AU516884B2 (en)	1981-06-25
ZM8477A1 (en)	1978-07-21
PL108918B1 (en)	1980-05-31
DE2754539A1 (de)	1978-06-15
GB1580799A (en)	1980-12-03
SU731906A3 (ru)	1980-04-30
PL202702A1 (pl)	1978-06-19
YU286977A (en)	1983-01-21

Legal Events

Date	Code	Title	Description
1998-01-20	MKEX	Expiry

Publication	Publication Date	Title
US4173616A (en)	1979-11-06	Extraction of copper values from aqueous solution
US4563256A (en)	1986-01-07	Solvent extraction process for recovery of zinc
EP1115891A1 (fr)	2001-07-18	Procede relatif a l'extraction et a la recuperation de cuivre
JPH0759728B2 (ja)	1995-06-28	金属有価物抽出用組成物
US4015980A (en)	1977-04-05	Use of fluorinated β-diketones in the solvent extraction of zinc
US4051223A (en)	1977-09-27	Process for the recovery of magnesium
US4153809A (en)	1979-05-08	Extractive separation of glycolic acid from diglycolic acid
US4822880A (en)	1989-04-18	Process for the extraction of metal values and novel metal extractants
CA1173040A (fr)	1984-08-21	Recuperation de methylnaphtalenes et d'autres bases de goudron, comme l'indole
US4234546A (en)	1980-11-18	Liquid/liquid extraction of nickel values
JPS6344539A (ja)	1988-02-25	カルボン酸、アルデヒド、ケトン、アルコ−ルおよびフエノ−ル希薄水溶液から抽出する連続的方法
US4675172A (en)	1987-06-23	Triazolopyrimidine extractants
GB1580799A (en)	1980-12-03	Process for the preparation of copper values from aqueous solutions
US3725046A (en)	1973-04-03	Solvent extraction process for the recovery of copper values
EP0112617B1 (fr)	1986-12-30	Procédé d'extraction de valeurs métalliques et extractants métalliques
US4108958A (en)	1978-08-22	Extraction of Cu(II), Fe(III), Ni(II), Co(II), Cd(II), Zn(II), Ca(II) and Mg(II) metal values using 2-hydroxy iminoacetic acids
CA1138474A (fr)	1982-12-28	Procede d'obtention d'une 1,2-dioxime
US5993757A (en)	1999-11-30	Reoximation of metal extraction circuit organics
US4239699A (en)	1980-12-16	Sulfonamidophenols, metal complexes thereof, and solutions containing such compounds for use in extraction of metal values
US3786096A (en)	1974-01-15	Recovery of adipic acid
US2324240A (en)	1943-07-13	Process for dehydration
AU742908B2 (en)	2002-01-17	Improved beta-diketones for the extraction of copper from aqueous ammoniacal solutions
CA2004692A1 (fr)	1990-06-10	Methode pour separer le cuivre des solutions basiques aqueuses
GB2024185A (en)	1980-01-09	Metal extraction process
US5068358A (en)	1991-11-26	Process for extracting n-methyl-2-pyrrolidone