CA1101444A - Traduction non-disponible - Google Patents

Traduction non-disponible

Info

Publication number: CA1101444A
Authority: CA; Canada
Prior art keywords: values; alkylphenyl; acids; hydroxyiminoacetic; aqueous solution
Prior art date: 1978-05-31
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

CA304,499A

Other languages

English (en)

Inventor

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.)

1978-05-31

Filing date

1978-05-31

Publication date

1981-05-19

1978-05-31 Application filed by Shell Canada Ltd filed Critical Shell Canada Ltd

1978-05-31 Priority to CA304,499A priority Critical patent/CA1101444A/fr

1981-05-19 Application granted granted Critical

1981-05-19 Publication of CA1101444A publication Critical patent/CA1101444A/fr

Status Expired legal-status Critical Current

Links

229910052751 metal Inorganic materials 0.000 title claims abstract description 26
239000002184 metal Substances 0.000 title claims abstract description 26
238000000622 liquid--liquid extraction Methods 0.000 title claims description 5
238000000638 solvent extraction Methods 0.000 title claims description 5
PBZUAIHRZUBBAJ-UHFFFAOYSA-N 2-hydroxyiminoacetic acid Chemical class ON=CC(O)=O PBZUAIHRZUBBAJ-UHFFFAOYSA-N 0.000 claims abstract description 15
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
125000001931 aliphatic group Chemical group 0.000 claims abstract description 11
150000001875 compounds Chemical class 0.000 claims abstract description 7
125000003118 aryl group Chemical group 0.000 claims abstract description 6
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 5
239000007864 aqueous solution Substances 0.000 claims description 25
-1 alkali metal salt Chemical class 0.000 claims description 18
238000000034 method Methods 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 13
239000000243 solution Substances 0.000 claims description 12
230000002378 acidificating effect Effects 0.000 claims description 11
239000010949 copper Substances 0.000 claims description 9
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
238000000926 separation method Methods 0.000 claims description 8
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
239000011575 calcium Substances 0.000 claims description 5
229910052791 calcium Inorganic materials 0.000 claims description 5
229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
239000011707 mineral Substances 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
ZXUQEPZWVQIOJE-UHFFFAOYSA-N methyl 2-chloro-2-oxoacetate Chemical compound COC(=O)C(Cl)=O ZXUQEPZWVQIOJE-UHFFFAOYSA-N 0.000 claims description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 3
VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
229910052749 magnesium Inorganic materials 0.000 claims description 3
238000006384 oligomerization reaction Methods 0.000 claims description 3
PBZUAIHRZUBBAJ-HNQUOIGGSA-N (2e)-2-hydroxyiminoacetic acid Chemical compound O\N=C\C(O)=O PBZUAIHRZUBBAJ-HNQUOIGGSA-N 0.000 claims description 2
CIPRIOUSROWZFM-UHFFFAOYSA-N 2-(4-dodecylphenyl)-2-hydroxyiminoacetic acid Chemical class CCCCCCCCCCCCC1=CC=C(C(=NO)C(O)=O)C=C1 CIPRIOUSROWZFM-UHFFFAOYSA-N 0.000 claims description 2
VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
150000004996 alkyl benzenes Chemical class 0.000 claims description 2
230000020477 pH reduction Effects 0.000 claims description 2
SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical class NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims 1
238000000605 extraction Methods 0.000 abstract description 29
239000003795 chemical substances by application Substances 0.000 abstract description 15
239000012071 phase Substances 0.000 abstract description 10
239000012074 organic phase Substances 0.000 abstract description 5
239000007788 liquid Substances 0.000 abstract 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
229910052802 copper Inorganic materials 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
239000001117 sulphuric acid Substances 0.000 description 7
235000011149 sulphuric acid Nutrition 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
238000009826 distribution Methods 0.000 description 6
150000002739 metals Chemical class 0.000 description 5
238000003756 stirring Methods 0.000 description 5
UYELYBQMASEWHA-UHFFFAOYSA-N 2-[2,4-di(propan-2-yl)phenyl]-2-hydroxyiminoacetic acid Chemical compound CC(C)C1=CC=C(C(=NO)C(O)=O)C(C(C)C)=C1 UYELYBQMASEWHA-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical class CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 4
229910052759 nickel Inorganic materials 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
239000010941 cobalt Substances 0.000 description 3
229910017052 cobalt Inorganic materials 0.000 description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 3
239000000284 extract Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 description 2
UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-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
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000001033 ether group Chemical group 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
239000003350 kerosene Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
125000000962 organic group Chemical group 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
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
VUMCUSHVMYIRMB-UHFFFAOYSA-N 1,3,5-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1 VUMCUSHVMYIRMB-UHFFFAOYSA-N 0.000 description 1
XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical class CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
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 1
JZEUFFFBEMAJHS-UHFFFAOYSA-N 2-methyldecan-1-ol Chemical compound CCCCCCCCC(C)CO JZEUFFFBEMAJHS-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
IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000518994 Conta Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
238000005868 electrolysis reaction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000000227 grinding Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910001510 metal chloride Inorganic materials 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
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 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
238000005829 trimerization reaction Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA304,499A 1978-05-31 1978-05-31 Traduction non-disponible Expired CA1101444A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA304,499A CA1101444A (fr)	1978-05-31	1978-05-31	Traduction non-disponible

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA304,499A CA1101444A (fr)	1978-05-31	1978-05-31	Traduction non-disponible

Publications (1)

Publication Number	Publication Date
CA1101444A true CA1101444A (fr)	1981-05-19

Family

ID=4111588

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA304,499A Expired CA1101444A (fr)	1978-05-31	1978-05-31	Traduction non-disponible

Country Status (1)

Country	Link
CA (1)	CA1101444A (fr)

1978
- 1978-05-31 CA CA304,499A patent/CA1101444A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-05-19	MKEX	Expiry

Publication	Publication Date	Title
US3428449A (en)	1969-02-18	Extraction of copper from acidic liquors with a phenolic oxime
US3971843A (en)	1976-07-27	Process for liquid/liquid extraction of gallium
US4701311A (en)	1987-10-20	Process for separating arsenic from acid solutions containing it
EP0202833B1 (fr)	1991-01-23	Composition et son utilisation pour l'extraction de métaux hors de solutions aqueuses
CA1056855A (fr)	1979-06-19	5-heptyl-2-hydroxybenzaldoximes
CA1137457A (fr)	1982-12-14	Composition et methode d'extraction metallurgique
US6277300B1 (en)	2001-08-21	Composition and use of composition for the extraction of metal values
US4724129A (en)	1988-02-09	Method of recovering gallium from very basic solutions by liquid/liquid extraction
US5024821A (en)	1991-06-18	Solvent extraction process
US3592775A (en)	1971-07-13	Compositions containing phenolic oximes and certain alpha-hydroxy aliphatic oximes
US3655347A (en)	1972-04-11	Process of extracting copper with certain substituted 2-hydroxybenzophenoximes
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
US4061564A (en)	1977-12-06	Treatment of solutions containing impure metals
US3579576A (en)	1971-05-18	Organophosphorus compounds and a process for the making thereof
US4018865A (en)	1977-04-19	Solvent-extraction process for recovery and separation of metal values
US3925472A (en)	1975-12-09	Phenolic oximes
CA1187706A (fr)	1985-05-28	Methode pour separer le germanium d'une solution aqueuse
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
US3981929A (en)	1976-09-21	Method of separating methylolphenols from solutions
EP0271468A2 (fr)	1988-06-15	Complexes de gallium et procédé de récupération du gallium par extraction par solvant
EP0106456B1 (fr)	1986-06-25	Procédé de récupération de tungstène
US4166837A (en)	1979-09-04	Solvent-extraction process for recovery and separation of metal values
US4781905A (en)	1988-11-01	Process for producing phosphoric acid and/or phosphates from wet-process phosphoric acid and an extractant therein
JPH0445444B2 (fr)	1992-07-24
CA1101444A (fr)	1981-05-19	Traduction non-disponible