US3481904A - Complex-forming poly-schiff's bases - Google Patents
Complex-forming poly-schiff's bases Download PDFInfo
- Publication number
- US3481904A US3481904A US575239A US3481904DA US3481904A US 3481904 A US3481904 A US 3481904A US 575239 A US575239 A US 575239A US 3481904D A US3481904D A US 3481904DA US 3481904 A US3481904 A US 3481904A
- Authority
- US
- United States
- Prior art keywords
- gold
- complex
- poly
- bases
- schiff
- 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.)
- Expired - Lifetime
Links
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 19
- 229910052737 gold Inorganic materials 0.000 description 19
- 239000010931 gold Substances 0.000 description 19
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229940015043 glyoxal Drugs 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 229920002521 macromolecule Polymers 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 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
- CBMIPXHVOVTTTL-UHFFFAOYSA-N gold(3+) Chemical compound [Au+3] CBMIPXHVOVTTTL-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- SONQUBLFXUMJKL-UHFFFAOYSA-N 2,3-diaminobenzenethiol Chemical compound NC1=CC=CC(S)=C1N SONQUBLFXUMJKL-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- XSPZOQBODSPAAP-UHFFFAOYSA-N Cl.Cl.SC1=CC=C(C=C1)S Chemical compound Cl.Cl.SC1=CC=C(C=C1)S XSPZOQBODSPAAP-UHFFFAOYSA-N 0.000 description 1
- CQVDKGFMVXRRAI-UHFFFAOYSA-J Cl[Au](Cl)(Cl)Cl Chemical compound Cl[Au](Cl)(Cl)Cl CQVDKGFMVXRRAI-UHFFFAOYSA-J 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 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
- 206010073261 Ovarian theca cell tumour Diseases 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- WYLQRHZSKIDFEP-UHFFFAOYSA-N benzene-1,4-dithiol Chemical compound SC1=CC=C(S)C=C1 WYLQRHZSKIDFEP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- LHQLJMJLROMYRN-UHFFFAOYSA-L cadmium acetate Chemical compound [Cd+2].CC([O-])=O.CC([O-])=O LHQLJMJLROMYRN-UHFFFAOYSA-L 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000001644 thecoma Diseases 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 235000009529 zinc sulphate Nutrition 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G7/00—Compounds of gold
- C01G7/003—Preparation involving a liquid-liquid extraction, an adsorption or an ion-exchange
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/06—Amines
- C08G12/08—Amines aromatic
-
- 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
- C22B3/42—Treatment or purification of solutions, e.g. obtained by leaching by ion-exchange extraction
-
- 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
- This invention relates to a poly-Schififs base which l d t t ti f up t 12 hours. can be used as speclfic complex form Of 1011 exchanger Any metal residues still adhering to the complex-former for gold. after such a treatment can be removed by treatment with It is known Bayef f Aflgewandte Chemie sodium or potassium cyanide. The material may then be 76 76 (1964)] that it is possible, by polycondensing 2,5- d again to ab orb gold,
- the charged N N complex-forming poly-Schiffs base is heated to a temperature above about 250 and up to 600 C.
- the organic CHCH n material is destroyed in this heating process and the gold This material is able to form complexes with metal is recovered in metallic form.
- the poly-Schiflfs base ions particularly those of the first and second subsidiary has a very high capacity of absorbing gold, the amounts groups of the periodic system, and to release them again. of this polymer used are rather small. Therefore, destroy- It has now been found that improved polycondensates ing these absorbing agents may be more economical then can be obtained by polycondensing l,4-diamino-2,5-dias expensive recovering process.
- the polycondensate is insoluble in the conventional peratures in the range from 40 to 90 C.
- the following organic solvents for example, alcohols, ethers, dimethyl general formula may be attributed to these polyconr formamide, acetone, chloroform, benzene and hydrocardensates. bons, and also in water. It is resistant to weak acids and weak alkaline liquors.
- n is a number greater than Y10 and may 2,5-dimercaptobenzene dihydrochloride were dissolved be as high as 2,000, preferably in the range of about 20 with continuous stirring in 70 ml. of distilled water to about 200. through which nitrogen was bubbled.
- the glyoxal is preferfree diamine, 14 ml. of a 12% by weight soda solution ably used in an amount equivalent to that of the 1,4- were added dropwise to the solution in a stream of diamino-Z,S-dimercaptobenzene or in an excess of up to nitrogen S0 that the P 0f e l e s o t 10 times the stoichiometrically necessary quantity. 7. Following complete neutralisation, the brownish-green The polycondensate according to the invention isa comsolution was heated to 60 C. in a paratfin bath, after plex-forrner which is practically specific for gold (III) which 8.8 g.
- the poly-SchifiYs base was stirred for 20 hours at room temperature in 0.1 N hydrochloric acid.
- the product was then suctionfiltered and successively washed three times with ml. of distilled water, 10 ml. of methanol and 10 ml. of ether and then dried over diphosphorus pentoxide at C./ 14 mm. Hg until its weight was constant.
- EXAMPLE 2 1 m1. of a 0.01 molar solution of zinc sulphate, 1 m1. of cadmium acetate, 1 ml. of mercury (II) acetate, 1 ml. of copper acetate and 1 ml. of tetrachloro-gold (III)- acid, were mixed together and made up to 1 litre with distilled water. 1 g. of poly-Schilts base, obtained as in Example 1, was added to this solution which was then shaken for 12 hours at room temperature. The macromolecule was then filtered off, after which the metal contents both of the filtrate and of the macromolecule are determined.
- the gold quantitatively combined with the macromolecule
- the copper (II)-, cadmium and zinc ions remained quantitatively in the solution. Only about one tenth of the mercury originally introduced also combined.
- the macromolecule was found to have combined with 1.92 mg. of gold (98%), 0.22 mg. of mercury (11%) and less than 0.002 mg. each of copper, cadmium and zinc.
- the product was shaken for 3 hours with 100 ml. of a 0.01 N sodium cyanide solution.
- Poly-Schilfs base consisting essentially of recurring units of the formula II N l-SH 118- I HS Ifil N SH Villa...
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- Geology (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Geochemistry & Mineralogy (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Inorganic Chemistry (AREA)
- Manufacture And Refinement Of Metals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0084286 | 1965-10-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3481904A true US3481904A (en) | 1969-12-02 |
Family
ID=6982364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US575239A Expired - Lifetime US3481904A (en) | 1965-10-28 | 1966-08-26 | Complex-forming poly-schiff's bases |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3481904A (enExample) |
| DE (1) | DE1570310A1 (enExample) |
| GB (1) | GB1089148A (enExample) |
| NL (1) | NL6614960A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5886224A (en) * | 1995-01-24 | 1999-03-23 | E. I. Du Pont De Nemours And Company | α-diimines for polymerization catalysts |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4066504A (en) | 1974-01-29 | 1978-01-03 | Givaudan Corporation | Aliphatic dialdehyde-aromatic polyamine condensation products bound to proteins and enzymes |
| DE3909302A1 (de) * | 1988-03-23 | 1989-10-12 | Yazaki Corp | Schmelzsicherung und verfahren zur herstellung derselben |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2412855A (en) * | 1943-11-22 | 1946-12-17 | Resinous Prod & Chemical Co | Process of sorbing ions |
| US2653089A (en) * | 1949-11-07 | 1953-09-22 | Phillips Petroleum Co | Recovery of heavy metals |
-
1965
- 1965-10-28 DE DE19651570310 patent/DE1570310A1/de active Pending
-
1966
- 1966-08-26 US US575239A patent/US3481904A/en not_active Expired - Lifetime
- 1966-10-04 GB GB44247/66A patent/GB1089148A/en not_active Expired
- 1966-10-21 NL NL6614960A patent/NL6614960A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2412855A (en) * | 1943-11-22 | 1946-12-17 | Resinous Prod & Chemical Co | Process of sorbing ions |
| US2653089A (en) * | 1949-11-07 | 1953-09-22 | Phillips Petroleum Co | Recovery of heavy metals |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5886224A (en) * | 1995-01-24 | 1999-03-23 | E. I. Du Pont De Nemours And Company | α-diimines for polymerization catalysts |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6614960A (enExample) | 1967-05-02 |
| DE1570310A1 (de) | 1970-03-05 |
| GB1089148A (en) | 1967-11-01 |
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