EP0731805A1 - Amides of acids of phosphorus for the extraction of metals - Google Patents

Amides of acids of phosphorus for the extraction of metals

Info

Publication number
EP0731805A1
EP0731805A1 EP95900829A EP95900829A EP0731805A1 EP 0731805 A1 EP0731805 A1 EP 0731805A1 EP 95900829 A EP95900829 A EP 95900829A EP 95900829 A EP95900829 A EP 95900829A EP 0731805 A1 EP0731805 A1 EP 0731805A1
Authority
EP
European Patent Office
Prior art keywords
optionally substituted
group
alkylphenoxy
compound
tert
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.)
Ceased
Application number
EP95900829A
Other languages
German (de)
English (en)
French (fr)
Inventor
John Campbell
Domenico Carlo Cupertino
Raymond Frederick Dalton
Peter Michael Quan
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.)
Avecia Ltd
Original Assignee
Zeneca 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.)
Filing date
Publication date
Application filed by Zeneca Ltd filed Critical Zeneca Ltd
Publication of EP0731805A1 publication Critical patent/EP0731805A1/en
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/2479—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1)
    • C07F9/2495—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1) containing the structure P(=X)n-N-P (X = O, S, Se; n = 0, 1)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/36—Amides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/44—Amides thereof
    • C07F9/4461—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4484—Compounds containing the structure C-P(=X)(N-acyl)-X, C-P(=X)(N-heteroatom)-X or C-P(=X)(N-CN)-X (X = O, S, Se)
    • 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
    • C22B3/38—Treatment or purification of solutions, e.g. obtained by leaching by liquid-liquid extraction using organic compounds containing phosphorus
    • C22B3/386—Polyphosphoric oxyacids, or derivatives thereof
    • 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

Definitions

  • the technique involves contacting an aqueous solution of metal salt, obtained for example by treating the crushed ore with acid, with a solution in a water-immiscible organic solvent of an organic extractant which complexes with the metal and extracts it into the non-aqueous phase.
  • the metal may then be recovered by a further extraction step in which the organic solution containing the metal complex is contacted with another aqueous phase containing an agent, usually a strong acid, capable of decomposing the complex so that the metal is extracted into the aqueous phase from which it can be recovered by suitable procedures such as electrowinning.
  • the organic solution is contacted with 5 to 6 molar hydrochloric acid to give ferric chloride in hydrochloric acid.
  • Free hydrochloric acid is recovered by a further step in which the ferric chloride in hydrochloric acid is contacted with an organic solution containing tributyl phosphate from which the ferric chloride is stripped using water.
  • R 1 -R 4 are as already defined. Whilst the invention is described herein with reference to compounds of Formula I, it is to be understood that it relates to said compounds in any of their possible tautomeric forms .
  • 2-alkylphenoxy groups which may be present in the compounds of Formula I, there may be mentioned phenoxy groups wherein the alkyl substituent in the 2- position relative to the oxygen atom contains from 1 to 20, for example from 1 to 10, carbon atoms.
  • Such alkyl groups may be primary alkyl groups having one or more carbon atoms, secondary alkyl groups having three or more carbon atoms or tertiary alkyl groups having four or more carbon atoms.
  • the phenoxy residue may optionally carry one or more additional alkyl substituents, for example an alkyl substituent in the 4-position.
  • Optionally substituted phenyl groups which may be represented by R 2 and/or R 3 and/or R 4 in the compounds of Formula I include alkyl substituted phenyl groups, for example o-tolyl, -tolyl, p-tolyl and xylyl groups and mixtures of such groups.
  • the preferred optionally substituted phenyl group is the unsubstituted phenyl group.
  • substituents which may be present in substituted alkyl or substituted alkoxy groups, there may be mentioned halogen, nitro, cyano, hydrocarbyloxy, hydrocarbyloxycarbonyl, acyl and acyloxy groups. More than one substituent may be present in which case the substituents may be the same or different.
  • R 1 is an optionally substituted 2-alkylphenoxy group
  • each of R 2 , R 3 and R 4 is either an optionally substituted 2-alkylphenoxy group or an optionally substituted phenyl group and at least one optionally substituted 2- alkylphenoxy group has a tertiary alkyl substituent except the compound wherein each of R 1 and R 2 is 2-isopropyl-4-tert- onylphenoxy and each of R 3 and R 4 is phenyl and the compound wherein R 1 is 2- methyl-4-.tert-nonylphenoxy, R 2 is 2,4-dimethylphenoxy and each of R 3 and R 4 is phenyl.
  • R 1 in this class of compounds is an optionally substituted 2-alkylphenoxy group, R 2 , R 3 and R 4 being phenyl groups, it is preferred that the phenoxy group is heavily substituted with aliphatic groups as in, for example, the 2-tert-butyl-4-tert- nonylphenoxy group to provide the extractant compound with good solubility in hydrocarbon solvents.
  • R 1 and R 2 are optionally substituted 2-alkylphenoxy groups, R 3 and R 4 being optionally substituted phenyl are strong metal extractants.
  • each of R 1 and R 2 is 2-methyl-4-tert-nonylphenoxy and each of R 3 and R 4 is phenyl.
  • R 1 is an optionally substituted 2- tert-alkylphenoxy group
  • R 2 is an optionally substituted alkoxy group
  • each of R 3 and R 4 is an optionally substituted 2- alkylphenoxy group or an optionally substituted alkoxy group.
  • at least one of R 3 and R 4 is a 2-tert-alkylphenoxy group.
  • a Grignard reagent may be reacted with a dialkyl phosphite to give a dialkyl phosphine oxide which is converted into the acid chloride by reaction with phosphorus trichloride as described by Robert H Williams and Lyle A Hamilton,
  • the extraction process may be applied to the extraction from aqueous solution of any metal capable of forming a stable complex with a compound of the invention in the organic phase.
  • the process is especially suitable for the solvent extraction of zinc from aqueous solutions of zinc salts, especially solutions obtained by the acid leaching of zinc ores. Examples, however, of other metals which can be extracted from acidic solutions having pH values of pH 2 and below are bismuth, cadmium, silver, mercury and copper but many other metals may also be extracted at higher pH values.
  • the amount of extractant compound to be used will depend upon the concentration of metal salt in the aqueous solution and also on the plant design.
  • Especially useful alcohols may be synthesised from highly branched precursors leading to very highly branched Guerbet alcohols containing a large number of terminal methyl groups.
  • particularly efficient alcohol modifiers include highly branched isohexadecyl alcohol and iso-octadecyl alcohol, the latter being 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanol.
  • Esters which may be used as modifiers in conjunction with the extractant compounds of the invention include saturated and unsaturated aliphatic and aromatic-aliphatic esters containing from 10 to 30 carbon atoms.
  • the esters may be mono-esters or polyesters, especially di-esters.
  • the esters are preferably highly branched.
  • the esters may contain other functional groups, particularly a hydroxyl group.
  • Especially useful esters include
  • Useful rate increasing additives include compounds which are known to be extractants for zinc and are soluble in the organic phase but with fast rates of extraction.
  • Compounds found to be effective in this aspect are other known zinc extractants such as esters of phosphoric acid, (eg D2EHPA) , and particularly surface active agents capable of transferring metal ions such as alkyl and aryl sulphonic acids having solubility in the organic phase.
  • Stages (1) and (2) of the aforementioned process may conveniently be carried out using well known conventional solvent extraction techniques.
  • the aqueous solution containing metal values is intimately contacted, in a single stage or in multiple stages but preferably continuously, with the organic phase (for example by agitating the two phases together in a suitable vessel) for a time sufficient to allow substantial extraction of the metal values from the aqueous solution, the two phases then being separated in any conventional manner.
  • the extraction is usually carried out at ambient temperature although somewhat higher temperatures, for example up to 100°C but preferably not more than 50°C, may be used if operationally convenient.
  • the chloro compound was isolated by diluting the mixture with diethyl ether (300cm 3 ) ,* the ether solution was extracted with water (three 100 cm 3 portions)and the organic layer was separated, dried with magnesium sulphate, filtered and concentrated by evaporation of the ether under reduced pressure yielding 0,0' -bis(2- isopropyl-5-methylphenyl) chlorothiophosphate which was an oil (73,lg) : 31 P NMR in CDC1 3 , singlet 56.7 ppm downfield of phosphoric acid.
  • a 0.20 molar solution of the compound to be tested in ESCAID 100 is shaken with an equal volume of a 0.1 molar aqueous solution of zinc sulphate containing sufficient sulphuric acid to give an initial pH value of 2.0.
  • Samples of the dispersion are withdrawn periodically and the aqueous layer is separated and analysed for zinc by titration with EDTA according to the usual procedure, until successive samples give the same zinc value denoting that equilibrium has been reached.
  • the amount of zinc which has passed into the or-ganic solution expressed as a concentration in parts of zinc by weight per million parts of solution by volume (ppm) is calculated.
  • the chloro compounds and amino compounds listed in Table 1 were prepared by the methods of Example 1, using as appropriate 2-sec- butylphenol, 2,4-dimethylphenol, 2-isopropyl-5-methylphenol or 2,6- dimethylphenol as starting materials. The chloro and amino compounds were then reacted together, also by the method of Example 1 to give the compounds of Formula 1 having the groups R 1 -R 4 listed. The strengths of these compounds as zinc extractants were examined by Test 1 with the results listed. The results show that the compounds of these Examples have strengths similar to the compound of Example 1.
  • phenylphosphonothioic dichloride Ph.PS.Cl 2 , obtainable from Jansen Chemical Company
  • An organic solution was prepared containing 0.5 moles per litre of the extractant of Example 24 in the hydrocarbon solvent Escaid 100.
  • a simulated high concentration zinc feed solution was prepared that contained 20.1 g/1 zinc, 12.5 g/1 ferric iron, 0.47 g/1 calcium, and 2.6 g/1 magnesium in an aqueous sulphate medium at pH 1.8.
  • the temperature of the reaction mixture was maintained at 38-40°C by external cooling.
  • the diethyl ether solution of 2-pentylmagnesium bromide was then added to a solution of phosphorus trichloride (946g, 6.88M) in diethyl ether (946 cm 3 ) during 3 hours.
  • the temperature of the reaction mixture was maintained at -20°C or lower by external cooling.
  • the reaction mixture was stirred at 0°C for 2 hours, over which time, a greyish solid resulted. Water (3000cm 3 ) was added to the reaction mixture over a period of 2 hours and the temperature was allowed to rise freely to 20°C.
  • the diethyl ether solution was separated and washed with brine (1 x 2000cm 3 ) , then with brine/Na 2 Co 3 (15% wt Vol NaCl, 2% wt.vol. Na 2 C0 3 ; 5 x 3000cm 3 ) and again with brine (1 x 2000cm 3 ) .
  • the diethyl ether solution was then concentrated by evaporation under reduced pressure. Low boiling impurities were removed by heating the residue under reduced pressure (25 mmHg) at a temperature of 80°C for 30 minutes.
  • the compound of Formula 1 was prepared by reacting bis (2- pentyl) chlorothiophosphate and 0,0' -bis (2-tert- butylphenoxy)thiophosphoramide by the method of Example 1.
  • the compound isolated was a brown oil (44.04g) .
  • the purity of the compound was estimated by titration as 89% of theoretical for M.W. of 580.6. 31 P n.m.r. in CDC1 3 , having two sets of multiplets centred at 41-.80 ppm and 90.85 ppm.
  • reaction mixture was allowed to warm up to ambient temperature to complete the reaction, and after 30 minutes, was cooled to -30°C. To this solution was then added a solution of sodium isopropoxide prepared by adding a suspension of sodium hydride (1.0M, 24g) in tetrahydrofuran (150cm 3 ) to a solution of commercial isopropanol (60g) in tetrahydrofuran (250cm 3 ) . The addition lasted 2 hours and the temperature was maintained below -30°C. The reaction mixture was allowed to warm to ambient temperature after which analysis by GC indicated that reaction was complete. The tetrahydrofuran was removed by vacuum evaporation and the residue was diluted with diethyl ether (1000cm 3 ) .
  • diethyl ether 1000cm 3
  • the amide (0.1M, 28.7g) was reacted with the chloro compound (0.1M, 30.65g) and sodium hydride (0.23M, 5.52g) in tetrahydrofuran (150cm 3 ) .
  • the reaction mixture was heated under reflux for 12 hours until analysis by HPLC indicated that the reaction was complete.
  • the product was purified and isolated as described in Example 1.
  • the reaction product obtained (30.7g) was found by titration to have a purity of 70% for a M.W. of 557.
  • the product was further purified by dissolving it in hexane (250cm 3 ) and washing the solution with a mixture of 90% vol MeOH and 10% vol H 2 0 (4-5 x 100cm 3 portions) .
  • the chloro compound listed in Table 6 was prepared by the method of Example 39.
  • the amino compound listed in Table 6 was prepared by the method of Example 34.
  • the chloro and amino compounds were reacted together by the methods of Example l to give the compound of Formula I having the groups R 1 - R 4 listed.
  • the purity of the compound was estimated by titration as 86% for MW of 557.
  • Example 42 This Example demonstrated the preparation of a compound of
  • the chloro compound listed in Table 6 was prepared by the methods of Example 39.
  • the amino compound listed in Table 6 was prepared by the methods of Example 10.
  • the chloro and amino compounds were reacted together by the methods of Example 1.
  • the purity of the compound having R 1 - R 4 listed in Table 6 was 76% for a compound of MW 647.
  • the behaviour of this compound in Test 1, is enumerated in Table 6.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Geology (AREA)
  • Geochemistry & Mineralogy (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Environmental & Geological Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Extraction Or Liquid Replacement (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP95900829A 1993-12-02 1994-11-11 Amides of acids of phosphorus for the extraction of metals Ceased EP0731805A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB939324757A GB9324757D0 (en) 1993-12-02 1993-12-02 Chemical compounds
GB9324757 1993-12-02
PCT/GB1994/002485 WO1995015329A1 (en) 1993-12-02 1994-11-11 Amides of acids of phosphorus for the extraction of metals

Publications (1)

Publication Number Publication Date
EP0731805A1 true EP0731805A1 (en) 1996-09-18

Family

ID=10746035

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95900829A Ceased EP0731805A1 (en) 1993-12-02 1994-11-11 Amides of acids of phosphorus for the extraction of metals

Country Status (11)

Country Link
EP (1) EP0731805A1 (fi)
JP (1) JPH09506349A (fi)
BR (1) BR9408208A (fi)
CA (1) CA2177064A1 (fi)
FI (1) FI962306A0 (fi)
GB (1) GB9324757D0 (fi)
NO (1) NO962264L (fi)
PE (1) PE1096A1 (fi)
PL (1) PL314792A1 (fi)
WO (1) WO1995015329A1 (fi)
ZA (1) ZA949069B (fi)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11532806B2 (en) 2014-04-01 2022-12-20 The Research Foundation For The State University Of New York Electrode materials that include an active composition of the formula MgzMxOy for group II cation-based batteries

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU1392497A (en) * 1996-02-17 1997-09-02 Zeneca Limited Extraction of cobalt and/or nickel from an aqueous feed solution
CN106140304A (zh) * 2015-04-17 2016-11-23 中国石油化工股份有限公司 一种乙烯三聚和四聚催化剂组合物及其制备和使用方法
CN115058597B (zh) * 2022-06-30 2024-06-04 盛隆资源再生（无锡）有限公司 一种含钙、铁、钴、镍的电镀污泥的回收处理方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4721605A (en) * 1985-07-24 1988-01-26 American Cyanamid Company Selective removal of metals from aqueous solutions with dithiophosphinic acids
US5028403A (en) * 1989-05-31 1991-07-02 American Cyanamid Company Metal recovery with monothiophosphinic acids
DE69327486D1 (de) * 1992-06-05 2000-02-10 Avecia Ltd Verfahren zum Extrahieren von Metallen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9515329A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11532806B2 (en) 2014-04-01 2022-12-20 The Research Foundation For The State University Of New York Electrode materials that include an active composition of the formula MgzMxOy for group II cation-based batteries

Also Published As

Publication number Publication date
CA2177064A1 (en) 1995-06-08
PL314792A1 (en) 1996-09-30
PE1096A1 (es) 1996-02-28
WO1995015329A1 (en) 1995-06-08
AU8149094A (en) 1995-06-19
BR9408208A (pt) 1997-08-26
GB9324757D0 (en) 1994-01-19
FI962306A (fi) 1996-05-31
JPH09506349A (ja) 1997-06-24
ZA949069B (en) 1995-08-28
AU685192B2 (en) 1998-01-15
NO962264L (no) 1996-07-30
NO962264D0 (no) 1996-05-31
FI962306A0 (fi) 1996-05-31

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