DD155295A1 - PROCESS FOR EXTRACTION OF COPPER FROM WAESSREN SOLUTIONS - Google Patents
PROCESS FOR EXTRACTION OF COPPER FROM WAESSREN SOLUTIONS Download PDFInfo
- Publication number
- DD155295A1 DD155295A1 DD22083280A DD22083280A DD155295A1 DD 155295 A1 DD155295 A1 DD 155295A1 DD 22083280 A DD22083280 A DD 22083280A DD 22083280 A DD22083280 A DD 22083280A DD 155295 A1 DD155295 A1 DD 155295A1
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- copper
- extraction
- hydrogen
- solutions
- introducing
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 6
- 238000000605 extraction Methods 0.000 title description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052802 copper Inorganic materials 0.000 claims abstract description 11
- 239000010949 copper Substances 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 238000000622 liquid--liquid extraction Methods 0.000 claims abstract 2
- 238000000638 solvent extraction Methods 0.000 claims abstract 2
- 239000000243 solution Substances 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 239000012266 salt solution Substances 0.000 claims description 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 abstract description 3
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 abstract description 3
- 150000003872 salicylic acid derivatives Chemical class 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- XWXMGTIHBYFTIE-UHFFFAOYSA-N chembl203360 Chemical class OC1=CC=CC=C1C1=NC2=CC=CC=C2N1 XWXMGTIHBYFTIE-UHFFFAOYSA-N 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 238000011084 recovery Methods 0.000 abstract 1
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229960000969 phenyl salicylate Drugs 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- KAHYDCBZFBPBCF-UHFFFAOYSA-N 2-n-dodecylbenzene-1,2-diamine Chemical compound CCCCCCCCCCCCNC1=CC=CC=C1N KAHYDCBZFBPBCF-UHFFFAOYSA-N 0.000 description 1
- RWQUYNOFCCFPNY-UHFFFAOYSA-N 2-n-octylbenzene-1,2-diamine Chemical compound CCCCCCCCNC1=CC=CC=C1N RWQUYNOFCCFPNY-UHFFFAOYSA-N 0.000 description 1
- ZWQBZEFLFSFEOS-UHFFFAOYSA-N 3,5-ditert-butyl-2-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=C(O)C(C(C)(C)C)=C1 ZWQBZEFLFSFEOS-UHFFFAOYSA-N 0.000 description 1
- DXBLGTHJSZTSSR-UHFFFAOYSA-N 4-nitro-2-(1-octylbenzimidazol-2-yl)phenol Chemical compound CCCCCCCCn1c(nc2ccccc12)-c1cc(ccc1O)[N+]([O-])=O DXBLGTHJSZTSSR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- UGHSPDKSELQUHP-UHFFFAOYSA-N OC1=CC=C([N+]([O-])=O)C=C1C1=NC2=CC=CC=C2N1 Chemical compound OC1=CC=C([N+]([O-])=O)C=C1C1=NC2=CC=CC=C2N1 UGHSPDKSELQUHP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000009854 hydrometallurgy Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- -1 phenylsulfonyl salicylate Chemical compound 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Die hydrometallurgische Kupfergewinnung unter Einsatz der Fluessig-Fluessig-Extraktion und Verwendung organischer Extragenzien besitzt bereits technische Bedeutung. Ein Entwicklungsziel stellt die Verbesserung der technischen Verfahren durch Einfuehrung billigerer Extragentien mit hoher Selektivitaet dar. In der vorliegenden Erfindung wird diesem Ziel durch Anwendung von kostenguenstig und technisch einfach herzustellenden 2-(o-Hydroxyphenyl)-benzimidazolen entsprochen. Dabei wird die Loeslichkeit in organischen Medien durch Einfuehrung laengerer Kohlenwasserstoff-Reste und die pH-Funktionalitaet durch Einfuehrung acidifizierender Nitrogruppen gesteuert. Die Synthese erfolgt aus Salicylsaeurederivaten und 1,2-Diaminobenzen bzw. dessen Derivaten.The hydrometallurgical copper recovery using the liquid-liquid extraction and the use of organic Extragenzien already has technical importance. A development goal is the improvement of the technical processes by introducing cheaper selectucts with high selectivity. In the present invention, this goal is met by applying cost-effectively and technically easy to prepare 2- (o-hydroxyphenyl) benzimidazoles. The solubility in organic media is controlled by the introduction of longer hydrocarbon residues and the pH functionality by introducing acidifying nitro groups. The synthesis is carried out from salicylic acid derivatives and 1,2-diaminobenzene or its derivatives.
Description
22083 222083 2
Verfahren zur Extraktion von Kupfer aus wäßrigen LösungenProcess for the extraction of copper from aqueous solutions
Anwendungsgebiet der ErfindungField of application of the invention
Die Erfindung bezieht sich auf das Gebiet der Hydrometallurgie und dient der Aufbereitung wäßriger Kupfersalzlösungen zur Metallgewinnung.The invention relates to the field of hydrometallurgy and serves the treatment of aqueous copper salt solutions for metal extraction.
Charakteristik der bekannten technischen LösungenCharacteristic of the known technical solutions
Für die Extraktion von Kupfer aus wäßrigen Metallsalzlösungen sind verschiedene Verfahren bekannt, die den Nachteil aufweisen, daß die Herstellung der eingesetzten Extraktionsmittel mit hohem ökonomischem Aufwand verbunden ist. Angewendet werden Extragenzien der LLX-Reihe (US-PS 3.655 34-7, US-PS 3 224 873) und der Kelex-Reihe (US-PS 3 637 711, US-PS 3 725 046). Einige andere Stoffe werden lediglich zur Anwendung vorgeschlagen (US-PS 3 637 476, US-PS 3 843 667, US-PS 4 123 4-35, DE-OS 2 703 593)* Bei der Synthese der LIX-Verbindungen sind insbesondere solche Reaktionsschritte wie die Umlagerung unter Einwirkung von Aluminiumchlorid und die vollständige Oximierung von Ketonen technisch schwer zu beherrschen Die Kelex-Ver-?· bindungen erfordern zu ihrer Herstellung zahlreiche, z»T· nicht einfach durchzuführende Syntheseschritte. Auch die Herstellung der weiteren vorgeschlagenen.Extragenzien ist technisch und ökonomisch aufwendig.For the extraction of copper from aqueous metal salt solutions, various processes are known which have the disadvantage that the preparation of the extraction agent used is associated with high economic outlay. Use is made of excipients of the LLX series (US Pat. No. 3,655,341, US Pat. No. 3,224,873) and the Kelex series (US Pat. No. 3,637,711, US Pat. No. 3,725,046). Some other substances are proposed for use only (US Pat. No. 3,637,476, US Pat. No. 3,843,667, US Pat. No. 4,123,435, DE-OS No. 2,703,593). Particular examples of the synthesis of the LIX compounds are those Reaction steps such as the rearrangement under the action of aluminum chloride and the complete oximation of ketones are technically difficult to control. The preparation of Kelex requires a number of synthetic steps, which are not easy to carry out. The production of the other proposed extras is technically and economically complicated.
Ziel der Erfindung Aim of the invention
Ziel der Erfindung ist ein Verfahren, in dem mit einfach herstellbaren und demzufolge billigen Extraktionsmitteln Kupfer aus wäßrigen sauren Lösungen selektiv extrahiert werden kann.The aim of the invention is a process in which copper can be selectively extracted from aqueous acidic solutions with easily prepared and therefore cheap extraction agents.
220832220832
Die Aufgabe wird entsprechend der Erfindung dadurch gelöst, daß eine Metallsalzlösung mit der Lösung eines substituierten 2-(o-Hydro2yphenyl)benzimidazols der allgemeinen FormelThe object is achieved according to the invention in that a metal salt solution with the solution of a substituted 2- (o-hydro 2-phenyl) benzimidazole of the general formula
in einem organischen Lösungsmittel kontaktiert wird. Die beiden Phasen werden danach in bekannter Weise getrennt, und die organische Phase wird einer Rückextraktion mit verdünnter Mineralsäure unterworfen·is contacted in an organic solvent. The two phases are then separated in a known manner and the organic phase is subjected to back-extraction with dilute mineral acid.
In der Formel bedeuten E Wasserstoff, Chlor, eine Nitro-In the formula, E is hydrogen, chlorine, a nitro
2 oder eine Alkylgruppe, R Wasserstoff oder eine Alkozygruppe, Br Wasserstoff, Chlor, eine Nitro- oder eine Alkylgruppe, R und/oder B? Wasserstoff oder eine Alkylgruppe. Die 2-(o-Hydroxyphenyl)benzimidazole sind leicht aus v industriell zugänglichen Salicylsäurederivaten sowie Derivaten des 1,2-Diaminobenzens darstellbar. Zur Verringerung der Löslichkeit der Reagenzien in Wasser verwendet man zweckmäßig kern- oder N-alkylierte 1,2-Diaminobenzene, bzw. auch kernalkylierte oder kernalkoxylierte Salicylsäuren und Salicylsäure derivate .2 or an alkyl group, R is hydrogen or an alkoxy group, Br is hydrogen, chlorine, a nitro or an alkyl group, R and / or B? Hydrogen or an alkyl group. The 2- (o-Hydroxyphenyl) benzimidazole can be displayed easily industrially accessible from v salicylic acid derivatives as well as derivatives of 1,2-Diaminobenzens. To reduce the solubility of the reagents in water it is expedient to use nuclear or N-alkylated 1,2-diaminobenzene, or else ring-alkylated or nuclear-alkoxylated salicylic acids and salicylic acid derivatives.
So sind zum Beispiel einsetzbar:For example:
Salicylsäurephenylester, ^-Isononyl-salicylsäurephenylester, 3,5-Di-tert-buty!salicylsäure, ^-Alkozsysalicylsäuremethylester, N-Dodecyl-1,2-diaminobenzen und 1,2~Diamino-4—alkylbenzen. Die Komponenten werden in einfacher Weise durch Er-Phenyl salicylate, phenylsulfonyl salicylate, 3,5-di-tert-butylsalicylic acid, methyl α-chlorosalicylate, N-dodecyl-1,2-diaminobenzene and 1,2-diamino-4-alkylbenzene. The components are easily
,-3- 220832, -3- 220832
hitzen miteinander umgesetzt. Für technische Anwendungen ist die Reinigung durch Kristallisation nicht unbedingt erforderlich.heat reacted with each other. For technical applications, purification by crystallization is not absolutely necessary.
1-0ctyl-2-(o-hydro3cyphenyl)benzimida2ol1-0ctyl-2- (o-hydro3cyphenyl) benzimida2ol
Äquimolare. Mengen von N-Octyl-1,2-diaminobenzen und Salicylsäurephenylester werden 4 Stunden auf 240 - 250 0C erhitzt. Das erhaltene Rohprodukt wird über das Hydrochlorid gereinigt.Equimolar. Amounts of N-octyl-1,2-diaminobenzene and phenyl salicylate are 240 4 hours - heated 250 0 C. The crude product obtained is purified via the hydrochloride.
Fp = 38 - 40 0C Mp = 38-40 0 C
1-Dodecyl-2~(2-hydroxy-5-3iitrophenyl)benzimidazolbenzimidazole 1-dodecyl-2 ~ (2-hydroxy-5-3iitrophenyl)
Äquimolare Mengen von N-Dodecyl~1,2-diaminobenzen und 5-Nitrosalicylsäurephenylester werden 4 Stunden auf I90 - 2000C erhitzt und das erhaltene Rohprodukt durch Umkristallisieren aus n-Heptan gereinigt. ~ 1,2-diaminobenzene equimolar amounts of N-dodecyl, and 5-Nitrosalicylsäurephenylester 4 hours I90 - heated 200 0 C and the crude product obtained was purified by recrystallization from n-heptane.
220832220832
Eine Salpetersaure Lösung, die 10 g/l Nitrat und 0,1 g/l Kupfer enthält, wird mit einer Lösung von 1-5 g/l 2(o-Eydroxyphenyl)benzimidazol in Amylalkohol im Phasenverhältnis "V^A0 = 1/1 in innigen Kontakt gebracht. Dabei wird das Kupfer in einem pH-Bereich von 3i5 - 4,5 quantitativ extrahiert·A nitric acid solution containing 10 g / l nitrate and 0.1 g / l copper is treated with a solution of 1-5 g / l 2 (o-Eydroxyphenyl) benzimidazole in amyl alcohol in the phase ratio "V ^ A 0 = 1 / 1 in which the copper is extracted quantitatively in a pH range of 3i5-4.5.
Eine salpetersaure Lösung, die 10 g/l Nitrat und 0,1 g/l Kupfer enthält, wird mit einer Lösung von 3-5 g/l 1-0ctyl-2(2-hydro2y-5-nitrophenyl)benzimidazol in Toluen im Phasenverhältnis VL1ZV". = 1/1 extrahiert. Dabei wirdA nitric acid solution containing 10 g / l of nitrate and 0.1 g / l of copper is phase-polarized with a solution of 3-5 g / l of 1-0ctyl-2 (2-hydroxy-5-nitrophenyl) benzimidazole in toluene VL 1 ZV ". = 1/1 extracted
w O 'Where '
das Kupfer in einem pH-Bereich von 3i5 - 4,5 quantitativ in die organische Phase überführt.the copper in a pH range of 3i5 - 4.5 transferred quantitatively into the organic phase.
Eine salpetersaure Lösung, die 10 g/l Nitrat und 0,1 g/l Kupfer enthält, wird mit einer Lösung von 3-5 g/l 1-Octyl-2(2-hydroxy-5-nitrophenyl)benzimidazol in Chloroform im Phasenverhältnis V^/V =1/1 extrahiert· Dabei wird das Kupfer in einem pH-Bereich von 3-4 quantitativ in die organische Phase überführt.A nitric acid solution containing 10 g / l of nitrate and 0.1 g / l of copper is phase-chromatized with a solution of 3-5 g / l of 1-octyl-2 (2-hydroxy-5-nitrophenyl) benzimidazole in chloroform V ^ / V = 1/1 extracted · The copper in a pH range of 3-4 is transferred quantitatively into the organic phase.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD22083280A DD155295A1 (en) | 1980-05-02 | 1980-05-02 | PROCESS FOR EXTRACTION OF COPPER FROM WAESSREN SOLUTIONS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD22083280A DD155295A1 (en) | 1980-05-02 | 1980-05-02 | PROCESS FOR EXTRACTION OF COPPER FROM WAESSREN SOLUTIONS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD155295A1 true DD155295A1 (en) | 1982-06-02 |
Family
ID=5523992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD22083280A DD155295A1 (en) | 1980-05-02 | 1980-05-02 | PROCESS FOR EXTRACTION OF COPPER FROM WAESSREN SOLUTIONS |
Country Status (1)
| Country | Link |
|---|---|
| DD (1) | DD155295A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2613246A1 (en) * | 1987-04-01 | 1988-10-07 | Ici Plc | PROCESS FOR SEPARATING METALS CAPABLE OF FORMING OXY-IONS IN AQUEOUS SOLUTION |
| AU2002316765B2 (en) * | 2001-06-13 | 2007-04-05 | Bhp Billiton Sa Limited | Solvent extraction mixture comprising substituted imidazole or benzimidazole for the separation of groups of base metals |
-
1980
- 1980-05-02 DD DD22083280A patent/DD155295A1/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2613246A1 (en) * | 1987-04-01 | 1988-10-07 | Ici Plc | PROCESS FOR SEPARATING METALS CAPABLE OF FORMING OXY-IONS IN AQUEOUS SOLUTION |
| AU2002316765B2 (en) * | 2001-06-13 | 2007-04-05 | Bhp Billiton Sa Limited | Solvent extraction mixture comprising substituted imidazole or benzimidazole for the separation of groups of base metals |
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