NO312890B1 - Gjenvinning av gadolinium og dets kompleksdannende midler fra vandige opplösninger inneholdende deres komplekser - Google Patents
Gjenvinning av gadolinium og dets kompleksdannende midler fra vandige opplösninger inneholdende deres komplekser Download PDFInfo
- Publication number
- NO312890B1 NO312890B1 NO19962041A NO962041A NO312890B1 NO 312890 B1 NO312890 B1 NO 312890B1 NO 19962041 A NO19962041 A NO 19962041A NO 962041 A NO962041 A NO 962041A NO 312890 B1 NO312890 B1 NO 312890B1
- Authority
- NO
- Norway
- Prior art keywords
- gadolinium
- acid
- complex
- oxalate
- complexing agent
- Prior art date
Links
- 229910052688 Gadolinium Inorganic materials 0.000 title claims abstract description 46
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 239000008139 complexing agent Substances 0.000 title claims abstract description 23
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 21
- 238000011084 recovery Methods 0.000 title claims description 14
- 238000000034 method Methods 0.000 claims abstract description 27
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000001556 precipitation Methods 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 239000002738 chelating agent Substances 0.000 claims description 21
- SQORATIMOBOFKR-UHFFFAOYSA-H gadolinium(3+);oxalate Chemical compound [Gd+3].[Gd+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O SQORATIMOBOFKR-UHFFFAOYSA-H 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 13
- -1 alkali metal oxalate Chemical class 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- 239000012452 mother liquor Substances 0.000 claims description 9
- WDLRUFUQRNWCPK-UHFFFAOYSA-N Tetraxetan Chemical compound OC(=O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 WDLRUFUQRNWCPK-UHFFFAOYSA-N 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- ROVQPMUIXHLBSK-UHFFFAOYSA-N 2-[2-[2-[2-carboxyethyl(carboxymethyl)amino]ethyl-(carboxymethyl)amino]ethyl-(carboxymethyl)amino]-3-phenylmethoxypropanoic acid Chemical compound OC(=O)CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)C(C(O)=O)COCC1=CC=CC=C1 ROVQPMUIXHLBSK-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 229920000768 polyamine Polymers 0.000 claims description 3
- LDGWQMRUWMSZIU-LQDDAWAPSA-M 2,3-bis[(z)-octadec-9-enoxy]propyl-trimethylazanium;chloride Chemical compound [Cl-].CCCCCCCC\C=C/CCCCCCCCOCC(C[N+](C)(C)C)OCCCCCCCC\C=C/CCCCCCCC LDGWQMRUWMSZIU-LQDDAWAPSA-M 0.000 claims description 2
- AQOXEJNYXXLRQQ-KRWDZBQOSA-N 2-[[(2s)-2-[bis(carboxymethyl)amino]-3-(4-ethoxyphenyl)propyl]-[2-[bis(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound CCOC1=CC=C(C[C@@H](CN(CCN(CC(O)=O)CC(O)=O)CC(O)=O)N(CC(O)=O)CC(O)=O)C=C1 AQOXEJNYXXLRQQ-KRWDZBQOSA-N 0.000 claims description 2
- 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 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- OUDSFQBUEBFSPS-UHFFFAOYSA-N ethylenediaminetriacetic acid Chemical compound OC(=O)CNCCN(CC(O)=O)CC(O)=O OUDSFQBUEBFSPS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000267 glycino group Chemical group [H]N([*])C([H])([H])C(=O)O[H] 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 150000003891 oxalate salts Chemical class 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- HSXRCEVTMOWCFI-UHFFFAOYSA-N 2-[4,7,10-tris(carboxymethyl)-6-methyl-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound CC1CN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CCN1CC(O)=O HSXRCEVTMOWCFI-UHFFFAOYSA-N 0.000 claims 1
- RZESKRXOCXWCFX-UHFFFAOYSA-N 2-[bis[2-[carboxymethyl-[2-(methylamino)-2-oxoethyl]amino]ethyl]amino]acetic acid Chemical compound CNC(=O)CN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC(=O)NC RZESKRXOCXWCFX-UHFFFAOYSA-N 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- MVWDJLOUEUAWIE-UHFFFAOYSA-N O=C=O.O=C=O Chemical compound O=C=O.O=C=O MVWDJLOUEUAWIE-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 7
- 229960003330 pentetic acid Drugs 0.000 description 7
- 238000001035 drying Methods 0.000 description 6
- 150000000921 Gadolinium Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 3
- MOJMYWALZOTAOX-UHFFFAOYSA-H O.O.O.O.O.O.O.O.O.O.C(C(=O)[O-])(=O)[O-].[Gd+3].C(C(=O)[O-])(=O)[O-].C(C(=O)[O-])(=O)[O-].[Gd+3] Chemical compound O.O.O.O.O.O.O.O.O.O.C(C(=O)[O-])(=O)[O-].[Gd+3].C(C(=O)[O-])(=O)[O-].C(C(=O)[O-])(=O)[O-].[Gd+3] MOJMYWALZOTAOX-UHFFFAOYSA-H 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- MXZROTBGJUUXID-UHFFFAOYSA-I [Gd+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC(=O)[O-])CCN(CC([O-])=O)C(C([O-])=O)COCC1=CC=CC=C1 Chemical compound [Gd+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC(=O)[O-])CCN(CC([O-])=O)C(C([O-])=O)COCC1=CC=CC=C1 MXZROTBGJUUXID-UHFFFAOYSA-I 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229910001938 gadolinium oxide Inorganic materials 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- HHLZCENAOIROSL-UHFFFAOYSA-N 2-[4,7-bis(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound OC(=O)CN1CCNCCN(CC(O)=O)CCN(CC(O)=O)CC1 HHLZCENAOIROSL-UHFFFAOYSA-N 0.000 description 1
- PCZHWPSNPWAQNF-LMOVPXPDSA-K 2-[[(2s)-2-[bis(carboxylatomethyl)amino]-3-(4-ethoxyphenyl)propyl]-[2-[bis(carboxylatomethyl)amino]ethyl]amino]acetate;gadolinium(3+);hydron Chemical compound [Gd+3].CCOC1=CC=C(C[C@@H](CN(CCN(CC(O)=O)CC([O-])=O)CC([O-])=O)N(CC(O)=O)CC([O-])=O)C=C1 PCZHWPSNPWAQNF-LMOVPXPDSA-K 0.000 description 1
- IQUHNCOJRJBMSU-UHFFFAOYSA-N H3HP-DO3A Chemical compound CC(O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 IQUHNCOJRJBMSU-UHFFFAOYSA-N 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000003926 complexometric titration Methods 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- AJNVQOSZGJRYEI-UHFFFAOYSA-N digallium;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Ga+3].[Ga+3] AJNVQOSZGJRYEI-UHFFFAOYSA-N 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- OCDAWJYGVOLXGZ-VPVMAENOSA-K gadobenate dimeglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC(O)=O)C(C([O-])=O)COCC1=CC=CC=C1 OCDAWJYGVOLXGZ-VPVMAENOSA-K 0.000 description 1
- HZHFFEYYPYZMNU-UHFFFAOYSA-K gadodiamide Chemical compound [Gd+3].CNC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC(=O)NC HZHFFEYYPYZMNU-UHFFFAOYSA-K 0.000 description 1
- 229940075613 gadolinium oxide Drugs 0.000 description 1
- CMIHHWBVHJVIGI-UHFFFAOYSA-N gadolinium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Gd+3].[Gd+3] CMIHHWBVHJVIGI-UHFFFAOYSA-N 0.000 description 1
- LGMLJQFQKXPRGA-VPVMAENOSA-K gadopentetate dimeglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O LGMLJQFQKXPRGA-VPVMAENOSA-K 0.000 description 1
- RYHQMKVRYNEBNJ-BMWGJIJESA-K gadoterate meglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 RYHQMKVRYNEBNJ-BMWGJIJESA-K 0.000 description 1
- GFSTXYOTEVLASN-UHFFFAOYSA-K gadoteric acid Chemical compound [Gd+3].OC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 GFSTXYOTEVLASN-UHFFFAOYSA-K 0.000 description 1
- 229910001195 gallium oxide Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000010842 industrial wastewater Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- 239000003643 water by type 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
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
Classifications
-
- 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
- C22B59/00—Obtaining rare earth metals
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
- C01F17/00—Compounds of rare earth metals
- C01F17/10—Preparation or treatment, e.g. separation or purification
- C01F17/17—Preparation or treatment, e.g. separation or purification involving a liquid-liquid extraction
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
- C01F17/00—Compounds of rare earth metals
- C01F17/20—Compounds containing only rare earth metals as the metal element
- C01F17/206—Compounds containing only rare earth metals as the metal element oxide or hydroxide being the only anion
- C01F17/224—Oxides or hydroxides of lanthanides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Geology (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Environmental & Geological Engineering (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Manufacture And Refinement Of Metals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI950986A IT1275426B (it) | 1995-05-16 | 1995-05-16 | Recupero del gadolinio e dei suoi agenti complessanti da soluzioni acquose contenenti i loro complessi |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO962041D0 NO962041D0 (no) | 1996-05-20 |
| NO962041L NO962041L (no) | 1996-11-18 |
| NO312890B1 true NO312890B1 (no) | 2002-07-15 |
Family
ID=11371605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19962041A NO312890B1 (no) | 1995-05-16 | 1996-05-20 | Gjenvinning av gadolinium og dets kompleksdannende midler fra vandige opplösninger inneholdende deres komplekser |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5595714A (fr) |
| EP (1) | EP0743283B1 (fr) |
| JP (1) | JP2889914B2 (fr) |
| AT (1) | ATE202542T1 (fr) |
| DE (2) | DE69613510T2 (fr) |
| ES (1) | ES2095821T3 (fr) |
| GR (1) | GR970300003T1 (fr) |
| IT (1) | IT1275426B (fr) |
| NO (1) | NO312890B1 (fr) |
| PT (1) | PT743283E (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009053171B4 (de) | 2009-11-04 | 2011-07-21 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Verfahren zur Herstellung des Calcium-Komplexes von Dihydroxy-hydroxy-methylpropyl-tetraazacyclododecan-triessigsäure (Calcobutrol) |
| EP2699556A1 (fr) | 2011-04-21 | 2014-02-26 | Bayer Intellectual Property GmbH | Préparation de gadobutrol de pureté élevée |
| EP2782900B1 (fr) * | 2011-11-25 | 2018-01-10 | Biophore India Pharmaceuticals Pvt. Ltd. | Procédé de purification de polyaminocarboxylates |
| US8940256B2 (en) | 2011-12-07 | 2015-01-27 | Xylon Technical Ceramics, Inc. | Method for recycling of rare earth and zirconium oxide materials |
| CN106187930B (zh) * | 2016-07-12 | 2018-10-19 | 嘉实（湖南）医药科技有限公司 | 高纯度考布曲钙的制备方法 |
| KR102395523B1 (ko) | 2016-09-27 | 2022-05-10 | 바이엘 파마 악티엔게젤샤프트 | 칼코부트롤의 변형체 a의 결정형의 제조 방법 |
| EP3820853A4 (fr) * | 2018-07-10 | 2022-08-17 | Biophore India Pharmaceuticals Pvt. Ltd. | Procédé de préparation d'acide 2,2',2''-(10-((2r,3s)-1,3,4-trihydroxy butan-2-yl)-1,4,7,10-tétraazacyclododécane-1,4,7-triyl) triacétique et de ses complexes |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA597181A (en) * | 1960-05-03 | Krumholz Pawel | Process for separating ions by ion exchange | |
| US2798789A (en) * | 1954-02-11 | 1957-07-09 | Frank H Spedding | Method of separating rare earths |
| US2897050A (en) * | 1954-04-28 | 1959-07-28 | Air Reduction | Separation of rare earth values by means of a cation exchange resin |
| US3054655A (en) * | 1957-09-02 | 1962-09-18 | Krumholz Pawel | Process for separating rare earths and yttrium by ion exchange |
| GB862688A (en) * | 1957-09-02 | 1961-03-15 | Pawel Krumholz | A process for separating ions by ion-exchange |
| US3033646A (en) * | 1957-10-09 | 1962-05-08 | Dow Chemical Co | Method of separating rare earth metal ions |
| US3037841A (en) * | 1958-08-19 | 1962-06-05 | Krumholz Pawel | Process for separating ions by ion exchange |
| US3167389A (en) * | 1962-05-15 | 1965-01-26 | American Potash & Chem Corp | Ion exchange process for separating the rare earths |
| US3275404A (en) * | 1963-10-07 | 1966-09-27 | Research Corp | Process for separating rare earth metal values |
| US3615173A (en) * | 1969-04-03 | 1971-10-26 | J Oscar Winget | Separation of rare earth elements by ion exchange |
| DE2818997C2 (de) * | 1978-02-17 | 1980-02-07 | Schweizerische Aluminium Ag, Chippis (Schweiz) | Verfahren zur Rückgewinnung und Trennung von Gadolinium und Gallium aus Schrott |
| US4400360A (en) * | 1982-12-01 | 1983-08-23 | Allied Corporation | Recovery of gadolinium and gallium oxides |
| US4405568A (en) * | 1982-12-20 | 1983-09-20 | Allied Corporation | Recovery of gadolinium and gallium oxides |
| US4438078A (en) * | 1982-12-20 | 1984-03-20 | Allied Corporation | Recovery of gadolinium and gallium oxides |
| JPS63182216A (ja) * | 1987-01-20 | 1988-07-27 | Daido Steel Co Ltd | 希土類元素の分離回収方法 |
-
1995
- 1995-05-16 IT ITMI950986A patent/IT1275426B/it active IP Right Grant
- 1995-05-24 US US08/448,741 patent/US5595714A/en not_active Expired - Lifetime
-
1996
- 1996-04-19 PT PT96106176T patent/PT743283E/pt unknown
- 1996-04-19 EP EP96106176A patent/EP0743283B1/fr not_active Expired - Lifetime
- 1996-04-19 DE DE69613510T patent/DE69613510T2/de not_active Expired - Lifetime
- 1996-04-19 AT AT96106176T patent/ATE202542T1/de not_active IP Right Cessation
- 1996-04-19 ES ES96106176T patent/ES2095821T3/es not_active Expired - Lifetime
- 1996-04-19 DE DE0743283T patent/DE743283T1/de active Pending
- 1996-05-15 JP JP8157335A patent/JP2889914B2/ja not_active Expired - Lifetime
- 1996-05-20 NO NO19962041A patent/NO312890B1/no not_active IP Right Cessation
-
1997
- 1997-02-28 GR GR970300003T patent/GR970300003T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US5595714A (en) | 1997-01-21 |
| NO962041D0 (no) | 1996-05-20 |
| DE743283T1 (de) | 1997-05-15 |
| JP2889914B2 (ja) | 1999-05-10 |
| JPH09100284A (ja) | 1997-04-15 |
| NO962041L (no) | 1996-11-18 |
| ATE202542T1 (de) | 2001-07-15 |
| EP0743283A3 (fr) | 1998-07-08 |
| ITMI950986A1 (it) | 1996-11-16 |
| GR970300003T1 (en) | 1997-02-28 |
| EP0743283B1 (fr) | 2001-06-27 |
| ES2095821T1 (es) | 1997-03-01 |
| ES2095821T3 (es) | 2001-09-01 |
| ITMI950986A0 (it) | 1995-05-16 |
| EP0743283A2 (fr) | 1996-11-20 |
| IT1275426B (it) | 1997-08-07 |
| DE69613510T2 (de) | 2001-10-25 |
| PT743283E (pt) | 2001-10-31 |
| DE69613510D1 (de) | 2001-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |