CS270844B1 - Method of metallic iones cu(ii),pb(ii),hg(ii),cd(ii),ni(ii),zn(ii),sr(ii),la(iii),uo2 2+, th(iv) removal from aqueous solutions - Google Patents
Method of metallic iones cu(ii),pb(ii),hg(ii),cd(ii),ni(ii),zn(ii),sr(ii),la(iii),uo2 2+, th(iv) removal from aqueous solutions Download PDFInfo
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- CS270844B1 CS270844B1 CS885769A CS576988A CS270844B1 CS 270844 B1 CS270844 B1 CS 270844B1 CS 885769 A CS885769 A CS 885769A CS 576988 A CS576988 A CS 576988A CS 270844 B1 CS270844 B1 CS 270844B1
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- Prior art keywords
- precipitate
- metal
- tenside
- surfactant
- acid
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- 238000000034 method Methods 0.000 title claims abstract description 19
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 10
- 241000575946 Ione Species 0.000 title 1
- 239000004094 surface-active agent Substances 0.000 claims abstract description 26
- 239000002244 precipitate Substances 0.000 claims abstract description 24
- 229910052751 metal Inorganic materials 0.000 claims abstract description 18
- 239000002184 metal Substances 0.000 claims abstract description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 6
- 239000011707 mineral Substances 0.000 claims abstract description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 5
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000007513 acids Chemical class 0.000 claims abstract description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 229910017053 inorganic salt Inorganic materials 0.000 claims abstract description 3
- 150000004696 coordination complex Chemical class 0.000 claims abstract 2
- 229910021645 metal ion Inorganic materials 0.000 claims description 11
- 238000011084 recovery Methods 0.000 claims 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 abstract description 4
- 150000002739 metals Chemical class 0.000 abstract description 4
- 238000001556 precipitation Methods 0.000 abstract description 4
- 230000008929 regeneration Effects 0.000 abstract description 4
- 238000011069 regeneration method Methods 0.000 abstract description 4
- 150000001455 metallic ions Chemical class 0.000 abstract 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 230000003252 repetitive effect Effects 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000000605 extraction Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000004062 sedimentation Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 2
- 102100032843 Beta-2-syntrophin Human genes 0.000 description 1
- 108050004003 Beta-2-syntrophin Proteins 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000005202 decontamination Methods 0.000 description 1
- 230000003588 decontaminative effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- -1 ethylenediaminetetraacetic acid sodium dodecylamide Chemical compound 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009854 hydrometallurgy Methods 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000004094 preconcentration Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KAEULCNPLNQDNI-UHFFFAOYSA-N sodium;dodecylazanide Chemical compound [Na+].CCCCCCCCCCCC[NH-] KAEULCNPLNQDNI-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- Removal Of Specific Substances (AREA)
Abstract
Description
Vynález sa týká spósobu odstraňovania kovových iónov ako sú Cu(II), Pb(II), Hg(II), Cd(II), Ni(II), Zn(II), Sr(II), La(III), U02 2+, Th(IV) z vodných roztokov.The invention relates to a method for removing metal ions such as Cu (II), Pb (II), Hg (II), Cd (II), Ni (II), Zn (II), Sr (II), La (III), U0. 2 2+ , Th (IV) from aqueous solutions.
V súčasnosti sa к odstračovaniu kovových iónov z vodných roztokov používajú viaceré spósoby: metody extrakčné - Morrison G.H., Freiser H.: Extrakčné metody v analytické chemii, SNTL, Praha (1962); Calligaro L., Mantovani A., Belluco U., Acampora M.: Polyhedron 2, 1189 (1903); Malát M.: Fresenius Z. Anal. Chem. 297, 497 (1979); Pakalns P.: Water Res. 15, 7 (1981); Chakravotty V., Dash K.G., Mohanty S.R.: Radiochem. Acta 40, 89 (1986); Grimm R., Kolařík Z.: Inorg. Nucl. Chem. 36, 189 (1974); Schepper A.: Hydrometallurgy 4, 285 (1979). V klasickej extrakcii přítomnost' tenzidov ovplyvňuje vlastnosti medzifázového povrchu, čím sa može negativné ovplyvniť rýchlosť extrakcie a extrakčná účinnost’ Huttinger K.J., Schegk J.R.: Chem. Ing.Těch. 53, 574 ( 1981 ); Ossec - Asare K.: Proč. Int. Solv. Extr. Conf. ISEC '83,Denver 278 (1983). Při použití tenzidu ako súčasti vodnej fázy v extrakcii pozoruje sa interferencia tenzidu s obomi fázami za vzniku emulzií, čo celý proces negativné ovplyvčuje - Pakalns P.: Water Res. 15, 7 (1981). lónový flotačný proces zahrňuje prídavok iónogenného tenzidu к roztokom iónov opačného náboja. Prebublávaním systému vzduchom alebo dusíkom sa tenzid adsorbuje spolu so separovanou zložkou na povrchu bublin a takto sa z roztoku oddel’uje - Berg E.W., Downey D.M.: Anal. Chim. Acta 120, 237 (1980); 121, 239 (1980); 123, 1 (1981); Lieam- Fang-Wu, Rui-Chim-Kuo, Shang-0a Huang: J. Chines. Chem. Soc. 27, 165 (1980). К izolácii rady kovov boli použité chelatačné sobenty: Kálalová E., Radová Z., Ulbert K., Kálal J., Švec F.: Europ. Polym. 0. 13, 299 (1977); Radová Z., Kálalová E., Kálal J., Kukuškin 3u.N., Simanová S.A., Konovalov L.V., Pak V.H.: Angew. Makromol. Chem. 81, 55 (1979); Kálalová E.: Chem. Prům. 31, 70 (1981). Ekonomickému využitiu týchto metod v mnohých prípadoch bráni nevratnost^ sorpčného procesu, použitie elučných kyselin o vysokej koncentrácii alebo vyhrievanie kolórt pře zvýšenie efektu desorpcie kovov:Currently, several methods are used to remove metal ions from aqueous solutions: extraction methods - Morrison G.H., Freiser H .: Extraction Methods in Analytical Chemistry, SNTL, Prague (1962); Calligaro L., Mantovani A., Belluco U., Acampora M., Polyhedron 2, 1189 (1903); Malát M .: Fresenius Z. Anal. Chem. 297, 497 (1979); Pakalns P .: Water Res. 15, 7 (1981); Chakravotty V., Dash K. G., Mohanty S. R., Radiochem. Acta, 40, 89 (1986); Grimm R., Kolarik Z .: Inorg. Nucl. Chem. 36, 189 (1974); Schepper A .: Hydrometallurgy 4, 285 (1979). In classical extraction, the presence of surfactants affects the properties of the interfacial surface, thereby negatively affecting the extraction rate and extraction efficiency. Huttinger K.J., Schegk J.R .: Chem. Ing.Těch. 53, 574 (1981); Ossec - Asare K .: Why. Int. Solv. Extr. Conf. ISEC '83, Denver 278 (1983). When using a surfactant as part of the aqueous phase in extraction, the surfactant interferes with both phases to form emulsions, which negatively affects the whole process - Pakalns P .: Water Res. 15, 7 (1981). the ion flotation process involves the addition of an ionic surfactant to the counterion ions solutions. By bubbling the system through air or nitrogen, the surfactant is adsorbed along with the separated component on the surface of the bubbles and is thus separated from the solution - Berg E.W., Downey D.M .: Anal. Chim. Acta 120,237 (1980); 121, 239 (1980); 123, 1 (1981); Lieam-Fang-Wu, Rui-Chim-Kuo, Shang-0, and Huang: J. Chines. Chem. Soc. 27, 165 (1980). Chelating agents were used to isolate many metals: Kálalová E., Radová Z., Ulbert K., Kálal J., Švec F .: Europ. Polym. 13, 299 (1977); Radová Z., Kálalová E., Kálal J., Kukuškin 3u.N., Simanová S.A., Konovalov L.V., Then V.H .: Angew. Dep. Chem. 81, 55 (1979); Kálalová E .: Chem. Avg. 31, 70 (1981). In many cases, the irreversibility of the sorption process, the use of high-concentration eluting acids or the heating of the colonies to increase the metal desorption effect prevent the economic use of these methods:
II
Kanert G.A., Chow A.: Anal. Chim. Acta 78, 375 (1975). Pře získavanie kovov využívá sa aj technika iónomeničov: Brajter K., Slonawska K.: Talanta 27, 745 (1980); Korkisch J.: Analytical techniques in environmenta chemistry, Pergamon Press, 449 (1981). Při viacstupňovej separácii je iónovýmenný proces kombinovaný s inými prekoncentračnými technikami ako je odparovanie alebo extrakcia.Kanert, G. A., Chow A., Anal. Chim. Acta 78: 375 (1975). Ion exchange techniques are also used to obtain metals: Brajter K., Slonawska K .: Talanta 27, 745 (1980); Korkisch J .: Analytical techniques in environmental chemistry, Pergamon Press, 449 (1981). In multi-stage separation, the ion exchange process is combined with other preconcentration techniques such as evaporation or extraction.
Vyššie uvedené nedostatky sú odstránené spůsobom odstraňovaní a kovových iónov ako sú Cu(II), Pb(II), Hg(II), Cd(II), Ni(II), Zn(II), Sr(II), La(III), U02 2+, Th(IV) z vodných roztokov s následnou regeneráciou použitého tenzidu, ktorého podstatou je, že na vodný roztok s obsahom kovových iónov sa působí tenzidom typu C-alkylamidov kyseliny etyléndiamíntetraoctovej s alkylom C^ až C2q v molárnom pomere tenzid : kov = 1:1 až 3 v rozsahu pH 1 až 7 za vzniku separovatel’nej zrazeniny komplexu kovu s tenzidom, ku ktorej sa přidá až 5 mol.dm minerálnej kyseliny ako kyselina sírová, kyselina dusičná, kyselina chlorovodíková, pričom kovový ión sa izoluje vo formě rozpustnej anorganickej soli a tenzid sa oddělí vo formě zrazeniny. Prídavkom minerálnej kyseliny ako je kyselina sírová, dusičná nebo chlorovodíková se může upravit’ pH vodného roztoku kovov.The above deficiencies are eliminated by the removal of metal ions such as Cu (II), Pb (II), Hg (II), Cd (II), Ni (II), Zn (II), Sr (II), La (III). ), U0 2 + 2, Th (IV) from an aqueous solution, followed by regeneration of the used surfactant, which is characterized in that the aqueous solution containing metal ions is treated with the surfactants of C-alkylamides of ethylenediaminetetraacetic acid with C ^ alkyl and C 2 q in a molar a surfactant-to-metal ratio of 1: 1 to 3 in the pH range of 1 to 7 to form a separable precipitate of the metal-surfactant complex to which up to 5 mol.dm of mineral acid such as sulfuric acid, nitric acid, hydrochloric acid is added; The ion is isolated as a soluble inorganic salt and the surfactant is collected as a precipitate. The pH of the aqueous metal solution can be adjusted by the addition of a mineral acid such as sulfuric, nitric or hydrochloric acid.
Postup podl’a vynálezu je demonstrovaný na príkladoch.The process according to the invention is demonstrated by examples.
Příklad 1Example 1
К vodě obsahujúcej 3,75.10'^ mol.dm”^ Cu(II) sa přidá 2,5.10^ mol.dm^ sodnej soli tenzidu oktadecylamid kyseliny etylén-diamíntetraoctovej. V takto pripravenom roztoku o pH 6,4 vytvára sa priamo zrazenina komplexu kovu s tenzidom, ktorá sa separuje v sedimentačněj nádrži. Ooba sedimentácie je 5 až 30 minut. Po oddělení zrazeniny sa obsah Cu(II) vo vodě zníži o 98 4 hmot.. Z izolovanej zrazeniny možno prídavkom kyseliny sírovej c/'H2S04/ = mol.dm regenerovat’ 99 hmot, povodného tenzidu, ktorý sa oddělí ako zrazenina od sú- časne získanej soli kovu a može sa opakované využit’ к ďalšiemu procesu zrážania kovových ionov. ,To water containing 3.75 * 10 mol / cm @ 2 Cu (II), 2.5 * 10 mol / cm @ 2 of the sodium salt of the surfactant ethylenediaminetetraacetic acid are added. In the thus prepared solution at pH 6.4, a precipitate of the metal-surfactant complex is formed directly, which is separated in a sedimentation tank. The period of sedimentation is 5 to 30 minutes. After separation of the precipitate, the Cu (II) in water is reduced to 98 wt .. 4 from the precipitate can be isolated by addition of sulfuric acid c / H 2 S0 4 / = mol.dm regenerated by 99 weight, of the original surfactant to be collected as a precipitate from the metal salt obtained simultaneously and can be reused for further metal ion precipitation process. .
CS 270844 8181 270844 81
Příklad 2Example 2
К vodě kontaminovanéj s 2,5 . 10 5 mol.dm 5 Cd(II) sa přidá ekvivalentně množstvo sodnej soli tenzidu dodecylamid kyseliny etyléndiamíntetřaoctovej. Po okyselení s HNO^ na pH 2,7 sa vytvářa filtrovatelná zrazenina komplexu kovu s tenzidom. Doba sedimentácie zrazeniny je 5 až 15 minút. Po oddělení zrazeniny (filtřáciou, resp. odstředěním) obsah kovu vo ·· vodě sa zníži o 80 až 91 % hmot.. Získanú zrazeninu možno okyselit prídavkom HC1 v koncentrácii 5 mol.dm”5, pričom tenzid sa zregeneruje na 90 až 98 % hmot, a oddělí se od roztoku súčasne získanej anorganickej soli kovu vo formě zrazeniny. Oddělená zrazenina tenzidu sa mÓže využit opakované к ďalšiemu procesu zrážania kovového iónu.Water contaminated with 2.5. An equivalent amount of ethylenediaminetetraacetic acid sodium dodecylamide surfactant is added equivalently to 5 mol.dm 5 of Cd (II). Upon acidification with HNO 2 to pH 2.7, a filterable precipitate of a metal-surfactant complex is formed. The sedimentation time of the precipitate is 5 to 15 minutes. After separation of the precipitate (filtration, respectively. Centrifugation) metal content of the water-·· is reduced by 80-91% by weight .. The obtained precipitate can be acidified by the addition of HC1 at 5 mol.dm "5, wherein the surfactant is to regenerate 90-98% %, and separated from the solution of the co-obtained inorganic metal salt in the form of a precipitate. The separated surfactant precipitate can be used repeatedly to further the metal ion precipitation process.
Příklad 3Example 3
К vodě obsahujúcej 5 . 10”4 mol.dm”5 Th(IV) sa přidá 2,0 . 10”4 mol.drn5 sodnej soli dodecylamidu kyseliny etyléndiamíntetraoctovej. Při pH 2,9 vytvářa sa po okyselení s HNO-j filtrovatelná zrazenina kovu s tenzidom, ktorá sedimentuje v priebehu 5 až 15 minút. Po oddělení zrazeniny obsah kovu vo vodě sa zn.íži o 80 až 85 % hmot.. Z izolovanej zrazeniny možno prídavkom kyseliny sírovej c/H2S0^/ = 3 mol.dm”5 regenerovat 90 až 98 % hmot, póvodného tenzidu, ktorý sa oddělí ako zrazenina od súčasne získanej soli kovu a móže sa opakované využit к dalšiemu procesu zrážania kovových iónov.Water containing 5. 10 4 4 mol.dm 5 5 Th (IV) is added 2.0. 10 "4 5 mol.drn dodecylamide sodium EDTA. At pH 2.9 a filterable metal precipitate with a surfactant is formed upon acidification with HNO 3, which settles over 5 to 15 minutes. After separation of the precipitate, the metal content in the water is reduced by 80 to 85% by weight. From the isolated precipitate, 90 to 98% by weight of the original surfactant can be recovered by the addition of sulfuric acid c / H 2 SO 4 = 3 mol.dm 5 . which is separated as a precipitate from the presently obtained metal salt and can be reused for another metal ion precipitation process.
Příklad 4Example 4
К vodě obsahujúcej 5 . 10’4 mol.dm”5 Hg(II) sa přidá tolko sodnej soli dodecylamidu kyseliny etyléndiamíntetraoctovej, aby poměr tenzidu.a kovu bol 1:1 až 2. Po úpravě pH roztoku s HNOj na pH 1 až 6 vytvářa sa zrazenina kovu s tenzidom. Po oddělení zrazeniny filtřáciou zníži sa obsah Hg(II) v roztoku maximálně o 91 % hmot.Water containing 5. 10 < 4 > mol.m < 5 > Hg (II) is added enough sodium salt of ethylenediaminetetraacetic acid dodecylamide to a surfactant to metal ratio of 1: 1 to 2. After adjusting the pH of the solution with surfactant. After separation of the precipitate by filtration, the Hg (II) content of the solution is reduced by a maximum of 91% by weight.
Příklad 5Example 5
К vodě obsahujúcej 3 . 10”5 mol.dm”5 Pb(II) sa přidá ekvivalentně množstvo sodnej soli dodecylamidu kyseliny etyléndiamíntetraoctovej. Po okyselení s HNO^ vytvářa sa pri pH 1,9 zrazenina Pb(II) s tenzidom. Po oddělení zrazeniny filtřáciou zníži sa obsah Pb(II) v roztoku o 90 % hmot.Water containing 3. 10 "5 mol.dm" 5 Pb (II) was added equivalent amount of a sodium salt of ethylenediaminetetraacetic acid dodecylamide. Upon acidification with HNO 2, a precipitate of Pb (II) with a surfactant is formed at pH 1.9. After separation of the precipitate by filtration, the Pb (II) content of the solution is reduced by 90% by weight.
Separácia kovových iónov s použitím chelátových tenzidov typu C-alkylamidov kyseliny etyléndiamíntetraoctovej při jednoduchej izolovatelnosti chelátov kovu, vysokej výtažnosti procesu v přepojení s možnostou vysokého stupňa regenerácie póvodných zložiek možno využit ako jednoduchú a ekonomicky výhodnú metodu v oblasti dekontaminácie odpadových vůd a kontaminovaných povrchov, vo vztahu к ochraně životného prostredia i ako metodu získavania kovov z priemyselných odpadov.Separation of metal ions using C-alkyl chelates of ethylenediaminetetraacetic acid C-alkylamides with simple metal chelate isolation, high interconnection process yield with the possibility of a high degree of regeneration of the original components can be used as a simple and economically advantageous method in decontamination of waste conduits and contaminated surfaces to protect the environment and as a method of recovering metals from industrial waste.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS885769A CS270844B1 (en) | 1988-08-25 | 1988-08-25 | Method of metallic iones cu(ii),pb(ii),hg(ii),cd(ii),ni(ii),zn(ii),sr(ii),la(iii),uo2 2+, th(iv) removal from aqueous solutions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS885769A CS270844B1 (en) | 1988-08-25 | 1988-08-25 | Method of metallic iones cu(ii),pb(ii),hg(ii),cd(ii),ni(ii),zn(ii),sr(ii),la(iii),uo2 2+, th(iv) removal from aqueous solutions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS576988A1 CS576988A1 (en) | 1989-12-13 |
| CS270844B1 true CS270844B1 (en) | 1990-08-14 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS885769A CS270844B1 (en) | 1988-08-25 | 1988-08-25 | Method of metallic iones cu(ii),pb(ii),hg(ii),cd(ii),ni(ii),zn(ii),sr(ii),la(iii),uo2 2+, th(iv) removal from aqueous solutions |
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| Country | Link |
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| CS (1) | CS270844B1 (en) |
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1988
- 1988-08-25 CS CS885769A patent/CS270844B1/en unknown
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| CS576988A1 (en) | 1989-12-13 |
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