CA2177064A1 - 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: CA2177064A1
Authority: CA; Canada
Prior art keywords: optionally substituted; group; alkylphenoxy; compound; tert
Prior art date: 1993-12-02
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.): Abandoned

Application number

CA002177064A

Other languages

English (en)

French (fr)

Inventor

John Campbell

Peter Michael Quan

Domenico Carlo Cupertino

Raymond Frederick Dalton

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.)

Syngenta Ltd

Original Assignee

Individual

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.)

1993-12-02

Filing date

1994-11-11

Publication date

1995-06-08

1994-11-11 Application filed by Individual filed Critical Individual

1995-06-08 Publication of CA2177064A1 publication Critical patent/CA2177064A1/en

Status Abandoned legal-status Critical Current

Links

229910052751 metal Inorganic materials 0.000 title claims abstract description 74
239000002184 metal Substances 0.000 title claims abstract description 74
150000002739 metals Chemical class 0.000 title abstract description 18
238000000605 extraction Methods 0.000 title description 23
229910052698 phosphorus Inorganic materials 0.000 title description 15
239000002253 acid Substances 0.000 title description 11
150000001408 amides Chemical class 0.000 title description 6
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title description 4
150000007513 acids Chemical class 0.000 title description 4
239000011574 phosphorus Substances 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 164
229910052725 zinc Inorganic materials 0.000 claims abstract description 74
239000011701 zinc Substances 0.000 claims abstract description 74
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 73
-1 2,4-dimethylphenoxy Chemical group 0.000 claims abstract description 72
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 45
239000007864 aqueous solution Substances 0.000 claims abstract description 27
125000005415 substituted alkoxy group Chemical group 0.000 claims abstract description 15
125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 10
239000000243 solution Substances 0.000 claims description 116
238000000034 method Methods 0.000 claims description 65
239000002904 solvent Substances 0.000 claims description 25
230000008569 process Effects 0.000 claims description 21
239000012071 phase Substances 0.000 claims description 19
239000012074 organic phase Substances 0.000 claims description 18
239000008346 aqueous phase Substances 0.000 claims description 15
150000004696 coordination complex Chemical class 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 7
229910021645 metal ion Inorganic materials 0.000 claims description 5
238000012546 transfer Methods 0.000 claims description 3
238000000638 solvent extraction Methods 0.000 abstract description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 88
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
238000006243 chemical reaction Methods 0.000 description 37
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
239000000203 mixture Substances 0.000 description 29
239000000047 product Substances 0.000 description 29
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 27
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
238000012360 testing method Methods 0.000 description 22
238000002360 preparation method Methods 0.000 description 21
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 20
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 19
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 19
239000012312 sodium hydride Substances 0.000 description 19
229910000104 sodium hydride Inorganic materials 0.000 description 19
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
125000001309 chloro group Chemical group Cl* 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
125000000217 alkyl group Chemical group 0.000 description 15
229910052760 oxygen Inorganic materials 0.000 description 14
239000003607 modifier Substances 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
150000001298 alcohols Chemical class 0.000 description 12
125000004432 carbon atom Chemical group C* 0.000 description 12
238000001704 evaporation Methods 0.000 description 12
230000008020 evaporation Effects 0.000 description 12
WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 description 12
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
235000019341 magnesium sulphate Nutrition 0.000 description 11
125000004437 phosphorous atom Chemical group 0.000 description 11
150000002148 esters Chemical class 0.000 description 10
229910052742 iron Inorganic materials 0.000 description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
238000004448 titration Methods 0.000 description 10
229910000147 aluminium phosphate Inorganic materials 0.000 description 9
238000004458 analytical method Methods 0.000 description 9
239000012527 feed solution Substances 0.000 description 9
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 9
239000000460 chlorine Substances 0.000 description 8
SEGLCEQVOFDUPX-UHFFFAOYSA-N di-(2-ethylhexyl)phosphoric acid Chemical compound CCCCC(CC)COP(O)(=O)OCC(CC)CCCC SEGLCEQVOFDUPX-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 7
150000002430 hydrocarbons Chemical class 0.000 description 7
239000004215 Carbon black (E152) Substances 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 6
229930195733 hydrocarbon Natural products 0.000 description 6
238000010992 reflux Methods 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
JLYVRXJEQTZZBE-UHFFFAOYSA-N ctk1c6083 Chemical compound NP(N)(N)=S JLYVRXJEQTZZBE-UHFFFAOYSA-N 0.000 description 5
NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 5
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
229910052753 mercury Inorganic materials 0.000 description 5
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 5
238000011084 recovery Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
LDXAOOOQBGRLFY-UHFFFAOYSA-N C1(=CC=CC=C1)N(P(O)=S)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)N(P(O)=S)C1=CC=CC=C1 LDXAOOOQBGRLFY-UHFFFAOYSA-N 0.000 description 4
VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
238000005363 electrowinning Methods 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
125000001863 phosphorothioyl group Chemical group *P(*)(*)=S 0.000 description 4
239000007858 starting material Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
239000001117 sulphuric acid Substances 0.000 description 4
235000011149 sulphuric acid Nutrition 0.000 description 4
MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 4
JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 3
IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
125000004104 aryloxy group Chemical group 0.000 description 3
239000012267 brine Substances 0.000 description 3
KYDJVKJYIMQCOP-UHFFFAOYSA-N chloro-di(pentan-2-yloxy)-sulfanylidene-$l^{5}-phosphane Chemical compound CCCC(C)OP(Cl)(=S)OC(C)CCC KYDJVKJYIMQCOP-UHFFFAOYSA-N 0.000 description 3
DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 description 3
SXIWNIQDOJKDGB-UHFFFAOYSA-N dichloro-phenyl-sulfanylidene-$l^{5}-phosphane Chemical compound ClP(Cl)(=S)C1=CC=CC=C1 SXIWNIQDOJKDGB-UHFFFAOYSA-N 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000007429 general method Methods 0.000 description 3
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
239000000463 material Substances 0.000 description 3
150000002989 phenols Chemical class 0.000 description 3
238000000746 purification Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000007787 solid Substances 0.000 description 3
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
239000000725 suspension Substances 0.000 description 3
XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 2
WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
OMVSWZDEEGIJJI-UHFFFAOYSA-N 2,2,4-Trimethyl-1,3-pentadienol diisobutyrate Chemical compound CC(C)C(=O)OC(C(C)C)C(C)(C)COC(=O)C(C)C OMVSWZDEEGIJJI-UHFFFAOYSA-N 0.000 description 2
KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 2
NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 2
IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 2
XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
PTFIPECGHSYQNR-UHFFFAOYSA-N 3-Pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 2
MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
241000283986 Lepus Species 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 2
VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 2
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
BATHVJUJMWQPMV-UHFFFAOYSA-M [Br-].CCCC(C)[Mg+] Chemical compound [Br-].CCCC(C)[Mg+] BATHVJUJMWQPMV-UHFFFAOYSA-M 0.000 description 2
239000003513 alkali Substances 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
LULLIKNODDLMDQ-UHFFFAOYSA-N arsenic(3+) Chemical compound [As+3] LULLIKNODDLMDQ-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
229910052797 bismuth Inorganic materials 0.000 description 2
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
JDIBGQFKXXXXPN-UHFFFAOYSA-N bismuth(3+) Chemical compound [Bi+3] JDIBGQFKXXXXPN-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052793 cadmium Inorganic materials 0.000 description 2
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
WLZRMCYVCSSEQC-UHFFFAOYSA-N cadmium(2+) Chemical compound [Cd+2] WLZRMCYVCSSEQC-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
CYXFIEPNEXBRTG-UHFFFAOYSA-N chloro-di(pentan-2-yl)phosphane Chemical compound CCCC(C)P(Cl)C(C)CCC CYXFIEPNEXBRTG-UHFFFAOYSA-N 0.000 description 2
BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
150000004795 grignard reagents Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000010410 layer Substances 0.000 description 2
BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229910052709 silver Inorganic materials 0.000 description 2
239000004332 silver Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
235000017550 sodium carbonate Nutrition 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
238000007738 vacuum evaporation Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
150000003751 zinc Chemical class 0.000 description 2
SZBYVOSSTHEBFR-UHFFFAOYSA-N 2-(2-methyloctan-2-yl)phenol Chemical compound CCCCCCC(C)(C)C1=CC=CC=C1O SZBYVOSSTHEBFR-UHFFFAOYSA-N 0.000 description 1
XVTOMLAMPUXGPS-UHFFFAOYSA-N 2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctan-1-ol Chemical compound CC(C)(C)CC(C)CCC(CO)C(C)CC(C)(C)C XVTOMLAMPUXGPS-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
LGAJYTCRJPCZRJ-UHFFFAOYSA-N 2-bromopentane Chemical compound CCCC(C)Br LGAJYTCRJPCZRJ-UHFFFAOYSA-N 0.000 description 1
HJBUWTLHZIRBIM-UHFFFAOYSA-N 2-chloro-4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C(Cl)=C1 HJBUWTLHZIRBIM-UHFFFAOYSA-N 0.000 description 1
XLBCWXYKVPIVHH-UHFFFAOYSA-N 2-hydroxy-5-nonylbenzonitrile Chemical compound CCCCCCCCCC1=CC=C(O)C(C#N)=C1 XLBCWXYKVPIVHH-UHFFFAOYSA-N 0.000 description 1
VPJOGDPLXNTKAZ-UHFFFAOYSA-N 2-methylpropanoic acid;2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)=O.CC(C)C(O)C(C)(C)CO VPJOGDPLXNTKAZ-UHFFFAOYSA-N 0.000 description 1
WTSHXGXZNWHRQM-UHFFFAOYSA-N 3-methyl-4-pentylphenol Chemical compound CCCCCC1=CC=C(O)C=C1C WTSHXGXZNWHRQM-UHFFFAOYSA-N 0.000 description 1
KJWMCPYEODZESQ-UHFFFAOYSA-N 4-Dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=C(O)C=C1 KJWMCPYEODZESQ-UHFFFAOYSA-N 0.000 description 1
KNDDEFBFJLKPFE-UHFFFAOYSA-N 4-n-Heptylphenol Chemical compound CCCCCCCC1=CC=C(O)C=C1 KNDDEFBFJLKPFE-UHFFFAOYSA-N 0.000 description 1
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
FIYXJPQDNPKZJJ-UHFFFAOYSA-N C1(=CC=CC=C1)[ClH]P(=S)[ClH]C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)[ClH]P(=S)[ClH]C1=CC=CC=C1 FIYXJPQDNPKZJJ-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
DTDWTFYDXWCOKB-UHFFFAOYSA-N [bis(2-tert-butylphenoxy)-lambda4-sulfanylidene]-chloro-dihydroxy-lambda5-phosphane Chemical compound CC(C)(C)C1=CC=CC=C1OS(=P(O)(O)Cl)OC2=CC=CC=C2C(C)(C)C DTDWTFYDXWCOKB-UHFFFAOYSA-N 0.000 description 1
159000000021 acetate salts Chemical class 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007806 chemical reaction intermediate Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 description 1
XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 1
XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
238000010668 complexation reaction Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
238000013461 design Methods 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
238000005868 electrolysis reaction Methods 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
239000008151 electrolyte solution Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
229910000286 fullers earth Inorganic materials 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
239000002035 hexane extract Substances 0.000 description 1
238000009854 hydrometallurgy Methods 0.000 description 1
KUYLHALFMPOMKK-UHFFFAOYSA-N hydroxy-sulfanylidene-bis(2,4,4-trimethylpentyl)-$l^{5}-phosphane Chemical compound CC(C)(C)CC(C)CP(O)(=S)CC(C)CC(C)(C)C KUYLHALFMPOMKK-UHFFFAOYSA-N 0.000 description 1
230000006872 improvement Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
CFSSWEQYBLCBLH-UHFFFAOYSA-N iso-hexadecyl alcohol Natural products CC(C)CCCCCCCCCCCCCO CFSSWEQYBLCBLH-UHFFFAOYSA-N 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
238000002386 leaching Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000011068 loading method Methods 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910052752 metalloid Inorganic materials 0.000 description 1
150000002738 metalloids Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
238000003918 potentiometric titration Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
239000012264 purified product Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
150000005199 trimethylbenzenes Chemical class 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1
125000005023 xylyl group Chemical group 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
239000011686 zinc sulphate Substances 0.000 description 1
235000009529 zinc sulphate Nutrition 0.000 description 1

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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Molecular Biology (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Health & Medical Sciences (AREA)
Crystallography & Structural Chemistry (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)

CA002177064A 1993-12-02 1994-11-11 Amides of acids of phosphorus for the extraction of metals Abandoned CA2177064A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB939324757A GB9324757D0 (en)	1993-12-02	1993-12-02	Chemical compounds
GB9324757.5		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
CA2177064A1 true CA2177064A1 (en)	1995-06-08

Family

ID=10746035

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002177064A Abandoned CA2177064A1 (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 (no)
JP (1)	JPH09506349A (no)
BR (1)	BR9408208A (no)
CA (1)	CA2177064A1 (no)
FI (1)	FI962306A0 (no)
GB (1)	GB9324757D0 (no)
NO (1)	NO962264L (no)
PE (1)	PE1096A1 (no)
PL (1)	PL314792A1 (no)
WO (1)	WO1995015329A1 (no)
ZA (1)	ZA949069B (no)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1997030181A1 (en) *	1996-02-17	1997-08-21	Zeneca Limited	Extraction of cobalt and/or nickel from an aqueous feed solution
WO2015153485A1 (en)	2014-04-01	2015-10-08	The Research Foundation For The State University Of New York	Electrode materials for group ii cation-based batteries
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

1993
- 1993-12-02 GB GB939324757A patent/GB9324757D0/en active Pending
1994
- 1994-11-11 CA CA002177064A patent/CA2177064A1/en not_active Abandoned
- 1994-11-11 PL PL94314792A patent/PL314792A1/xx unknown
- 1994-11-11 EP EP95900829A patent/EP0731805A1/en not_active Ceased
- 1994-11-11 BR BR9408208A patent/BR9408208A/pt not_active Application Discontinuation
- 1994-11-11 JP JP7515460A patent/JPH09506349A/ja active Pending
- 1994-11-11 WO PCT/GB1994/002485 patent/WO1995015329A1/en not_active Application Discontinuation
- 1994-11-15 ZA ZA949069A patent/ZA949069B/xx unknown
- 1994-12-01 PE PE1994256237A patent/PE1096A1/es not_active Application Discontinuation
1996
- 1996-05-31 FI FI962306A patent/FI962306A0/fi unknown
- 1996-05-31 NO NO962264A patent/NO962264L/no unknown

Also Published As

Publication number	Publication date
FI962306L (fi)	1996-05-31
NO962264D0 (no)	1996-05-31
WO1995015329A1 (en)	1995-06-08
PL314792A1 (en)	1996-09-30
NO962264L (no)	1996-07-30
JPH09506349A (ja)	1997-06-24
AU8149094A (en)	1995-06-19
ZA949069B (en)	1995-08-28
GB9324757D0 (en)	1994-01-19
PE1096A1 (es)	1996-02-28
AU685192B2 (en)	1998-01-15
FI962306A0 (fi)	1996-05-31
EP0731805A1 (en)	1996-09-18
BR9408208A (pt)	1997-08-26

Publication	Publication Date	Title
US5557003A (en)	1996-09-17	Alkylphenoxy substituted bis (thio phosphoryl) amines
JPS5817882A (ja)	1983-02-02	酸性水溶液からの重金属イオンの液体／液体−抽出法
US5393431A (en)	1995-02-28	Process for extracting metals
CA1177255A (en)	1984-11-06	Extraction process for the selective removal of cobalt (ii) from aqueous solutions
AU711913B2 (en)	1999-10-21	Ferric fluoborate/organic extractant hydrometallurgical process for recovering metals
CA2177064A1 (en)	1995-06-08	Amides of acids of phosphorus for the extraction of metals
EP0023428B1 (en)	1985-11-21	Liquid-liquid process for extracting metals using organo-phosphorous compounds
US4915919A (en)	1990-04-10	Recovery of germanium from aqueous solutions by solvent extraction
US3464784A (en)	1969-09-02	Extraction of tetravalent vanadium values from their aqueous solutions using hydroxamic acids
AU685192C (en)	1999-03-25	Amides of acids of phosphorus for the extraction of metals
US4666513A (en)	1987-05-19	Process for the selective extraction of copper using 4-acyl-(3H)-pyrazol-3-ones
EP0112617A1 (en)	1984-07-04	Process for the extraction of metal values and novel metal extractants
WO1997001649A1 (en)	1997-01-16	Method for selective separation of cadmium from an acidic aqueous solution
US4836956A (en)	1989-06-06	Extraction of polyvalent metals with organodiphosphonic acids
WO1997030181A1 (en)	1997-08-21	Extraction of cobalt and/or nickel from an aqueous feed solution
US4150242A (en)	1979-04-17	Process for the preparation of bis-(β-carboxyethyl) alkyl phosphine oxides from bis-(β-cyanoethyl) alkyl phosphine
US4149014A (en)	1979-04-10	Process for the preparation of bis-(β-carboxyethyl)alkyl phosphine oxides from tris-cyanoethyl phosphine
GB2607991A (en)	2022-12-21	A recycling method for battery and catalyst materials
CA1312207C (en)	1993-01-05	Recovery of germanium from aqueous solutions by solvent extraction
US4071549A (en)	1978-01-31	Process for the preparation of bis-(beta-cyanoethyl) alkyl phosphine from tris-cyanoethyl phosphine
JPS6314054B2 (no)	1988-03-29
WO2004054954A1 (en)	2004-07-01	Process for the purification of hydroxyaryl-aldhydes and ketones and their use in the production of hydroxyaryl oxime derivatives
CA2168036A1 (en)	1995-02-16	A process for recovering metals
GB2286589A (en)	1995-08-23	Sulphonamides for solvent extraction

Legal Events

Date	Code	Title	Description
2001-11-13	FZDE	Discontinued