IL132129A - Method for removing heavy metal ions from aqueous solutions of organic compounds - Google Patents
Method for removing heavy metal ions from aqueous solutions of organic compoundsInfo
- Publication number
- IL132129A IL132129A IL13212998A IL13212998A IL132129A IL 132129 A IL132129 A IL 132129A IL 13212998 A IL13212998 A IL 13212998A IL 13212998 A IL13212998 A IL 13212998A IL 132129 A IL132129 A IL 132129A
- Authority
- IL
- Israel
- Prior art keywords
- sulfide
- water
- palladium
- aqueous
- solutions
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- 229910001385 heavy metal Inorganic materials 0.000 title claims abstract description 23
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 15
- 150000002500 ions Chemical class 0.000 title claims abstract description 5
- 239000007864 aqueous solution Substances 0.000 title claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 62
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 31
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 16
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000011135 tin Substances 0.000 claims abstract description 7
- 229910052718 tin Inorganic materials 0.000 claims abstract description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000001556 precipitation Methods 0.000 claims abstract description 6
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 150000004763 sulfides Chemical class 0.000 claims description 5
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 150000001298 alcohols Chemical class 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- -1 alkaline-earth metal sulfide Chemical class 0.000 claims 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 claims 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical group [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229940079101 sodium sulfide Drugs 0.000 description 3
- ZGHLCBJZQLNUAZ-UHFFFAOYSA-N sodium sulfide nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[Na+].[S-2] ZGHLCBJZQLNUAZ-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000006880 cross-coupling reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000007172 homogeneous catalysis Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 229940048181 sodium sulfide nonahydrate Drugs 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- WMDLZMCDBSJMTM-UHFFFAOYSA-M sodium;sulfanide;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[SH-] WMDLZMCDBSJMTM-UHFFFAOYSA-M 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- KPTRWOZEZUKTLT-UHFFFAOYSA-M N.[OH-].O.O.O.O.O.O.O.O.O.[Na+].S Chemical compound N.[OH-].O.O.O.O.O.O.O.O.O.[Na+].S KPTRWOZEZUKTLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- SJESFSGYKOQFCN-IDMXKUIJSA-N methyl (2s)-2-amino-3-[4-(1,3-thiazol-2-yl)phenyl]propanoate;dihydrochloride Chemical compound Cl.Cl.C1=CC(C[C@H](N)C(=O)OC)=CC=C1C1=NC=CS1 SJESFSGYKOQFCN-IDMXKUIJSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002993 phenylalanine derivatives Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- NRUVOKMCGYWODZ-UHFFFAOYSA-N sulfanylidenepalladium Chemical compound [Pd]=S NRUVOKMCGYWODZ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical compound [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 description 1
- 239000012989 trithiocarbonate Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
- C07B63/02—Purification; Separation; Stabilisation; Use of additives by treatment giving rise to a chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Removal Of Specific Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT97MI001107A IT1291355B1 (it) | 1997-05-13 | 1997-05-13 | Metodo per la rimozione dei metalli pesanti da composti organici |
| PCT/EP1998/002629 WO1998051647A1 (en) | 1997-05-13 | 1998-05-04 | Method for removing heavy metals from organic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL132129A0 IL132129A0 (en) | 2001-03-19 |
| IL132129A true IL132129A (en) | 2004-06-20 |
Family
ID=11377118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL13212998A IL132129A (en) | 1997-05-13 | 1998-05-04 | Method for removing heavy metal ions from aqueous solutions of organic compounds |
Country Status (9)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19929258A1 (de) * | 1999-06-25 | 2000-12-28 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| CN100427549C (zh) * | 2004-11-15 | 2008-10-22 | 东南大学 | 配合法去除染料中重金属的方法 |
| US9499420B2 (en) | 2012-11-06 | 2016-11-22 | Thatcher Company, Inc. | Formulations and methods for removing heavy metals from waste solutions containing chelating agents |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4629570A (en) * | 1981-11-09 | 1986-12-16 | Dowell Schlumberger Incorporated | Removal of iron from chelant solutions |
| US4678584A (en) * | 1985-06-20 | 1987-07-07 | Cx/Oxytech, Inc. | Method of removing heavy metal from wastewater streams |
| US4971775A (en) * | 1987-06-30 | 1990-11-20 | Dowell Schlumberger | Process for removal of nickel from effluent containing EDTA |
| IN170303B (US06559137-20030506-C00021.png) | 1987-09-02 | 1992-03-14 | Hoechst Ag | |
| JP3034650B2 (ja) * | 1991-06-19 | 2000-04-17 | 株式会社ジーシー | 歯質用接着剤 |
| US5160631A (en) | 1991-08-05 | 1992-11-03 | Halliburton Company | Method for treating chelant solutions to remove metals in solution |
-
1997
- 1997-05-13 IT IT97MI001107A patent/IT1291355B1/it active IP Right Grant
-
1998
- 1998-05-04 IL IL13212998A patent/IL132129A/en not_active IP Right Cessation
- 1998-05-04 EP EP98928226A patent/EP0983217B1/en not_active Expired - Lifetime
- 1998-05-04 WO PCT/EP1998/002629 patent/WO1998051647A1/en active IP Right Grant
- 1998-05-04 US US09/381,638 patent/US6177571B1/en not_active Expired - Fee Related
- 1998-05-04 AT AT98928226T patent/ATE275119T1/de not_active IP Right Cessation
- 1998-05-04 ES ES98928226T patent/ES2229505T3/es not_active Expired - Lifetime
- 1998-05-04 DE DE69825988T patent/DE69825988T2/de not_active Expired - Fee Related
- 1998-05-04 CA CA002287553A patent/CA2287553A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| IT1291355B1 (it) | 1999-01-07 |
| CA2287553A1 (en) | 1998-11-19 |
| ITMI971107A0 (US06559137-20030506-C00021.png) | 1997-05-13 |
| EP0983217A1 (en) | 2000-03-08 |
| US6177571B1 (en) | 2001-01-23 |
| ES2229505T3 (es) | 2005-04-16 |
| EP0983217B1 (en) | 2004-09-01 |
| DE69825988D1 (de) | 2004-10-07 |
| IL132129A0 (en) | 2001-03-19 |
| ITMI971107A1 (it) | 1998-11-13 |
| WO1998051647A1 (en) | 1998-11-19 |
| ATE275119T1 (de) | 2004-09-15 |
| DE69825988T2 (de) | 2005-09-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0687830A (ja) | ２，２，６，６−テトラメチルピペリジンのｎ−オキシル誘導体およびその製法 | |
| EP0983217B1 (en) | Method for removing heavy metals from organic compounds | |
| AU2006242782B2 (en) | New process for synthesis of proton pump inhibitors | |
| US7220855B2 (en) | Process for producing methylcobalamin | |
| US5712400A (en) | Process for preparation of 5-hydroxymethylthiazole | |
| US6211380B1 (en) | Process for the preparation of heteroaryl-zinc halides | |
| US5336775A (en) | Method of producing tertiary amine-sulphur-trioxide-complexes | |
| US6239301B1 (en) | Process for the removal of heavy metals | |
| EP0962552B1 (en) | A process for the preparation of 4-(des-dimethylamino)-tetracyclines | |
| IE76463B1 (en) | A method of reducing a carbonyl containing acridine | |
| US5602255A (en) | Process for producing tetrahydroisoquinoline-3-carboxylic acid compounds | |
| SK154294A3 (en) | Method of production of 2,4,5-tribrompyrole-3-carbonitrile | |
| CA2457576C (en) | Hydrates of optionally substituted 2-(2-pyridinyl)methylthio-1h-benzimidazoles and process for the production thereof | |
| WO2001017974A1 (en) | Process for preparing a 1-substituted 5-hydroxymethyl imidazole | |
| CN112694453B (zh) | 一种n-甲基化含氮芳香杂环化合物的制备方法 | |
| EP0636612A1 (en) | Process for producing tetrahydroisoquinoline-3-carboxylic acid derivative | |
| US5840972A (en) | Process for preparing NG -monoalkyl-L-arginine and related compounds | |
| CN1264358A (zh) | 制备3－羟基－2－甲基苯甲酸的方法 | |
| Koskinen et al. | Diazo transfer reactions under mildly basic conditions | |
| AU764168B2 (en) | Method for preparing 5-(1-methylethyl)-6-(phenylmethyl) pyrimidine-2,4(1H,3H)-dione | |
| KR0148125B1 (ko) | 1,4-디하이드로피리딘 카복실산 유도체 및 그의 제조방법 | |
| KR100238645B1 (ko) | 세팔로스포린 유도체의 새로운 에스테르화 방법 | |
| CS226741B2 (en) | Method of preparing 5-alkyl-2-pyrazinecarboxylic acid | |
| MXPA99006648A (es) | Proceso para la preparacion de haluros de heteroaril-cinc | |
| MXPA99010410A (en) | Process for the removal of heavy metals |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |