RU2472772C2 - Способ получения триэтилентетрамина (тэта) через этилендиаминдиацетонитрил (эддн) - Google Patents
Способ получения триэтилентетрамина (тэта) через этилендиаминдиацетонитрил (эддн) Download PDFInfo
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- RU2472772C2 RU2472772C2 RU2009136185/04A RU2009136185A RU2472772C2 RU 2472772 C2 RU2472772 C2 RU 2472772C2 RU 2009136185/04 A RU2009136185/04 A RU 2009136185/04A RU 2009136185 A RU2009136185 A RU 2009136185A RU 2472772 C2 RU2472772 C2 RU 2472772C2
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- CWVZGJORVTZXFW-UHFFFAOYSA-N [benzyl(dimethyl)silyl]methyl carbamate Chemical compound NC(=O)OC[Si](C)(C)CC1=CC=CC=C1 CWVZGJORVTZXFW-UHFFFAOYSA-N 0.000 description 1
- VMNCXMXVXKXPRY-UHFFFAOYSA-N acetonitrile;n'-(2-aminoethyl)ethane-1,2-diamine Chemical compound CC#N.NCCNCCN VMNCXMXVXKXPRY-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229910002056 binary alloy Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VIQAOIGVRNWUDN-UHFFFAOYSA-N ethane-1,2-diamine formaldehyde Chemical compound C=O.C(CN)N VIQAOIGVRNWUDN-UHFFFAOYSA-N 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- PBDJMCVHJGOTGP-UHFFFAOYSA-N ethenamine;piperazine Chemical compound NC=C.C1CNCCN1 PBDJMCVHJGOTGP-UHFFFAOYSA-N 0.000 description 1
- UMXYJWSQJORGEM-UHFFFAOYSA-N ethene;piperazine Chemical group C=C.C1CNCCN1 UMXYJWSQJORGEM-UHFFFAOYSA-N 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000003916 ethylene diamine group Chemical group 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- WBIWIXJUBVWKLS-UHFFFAOYSA-N n'-(2-piperazin-1-ylethyl)ethane-1,2-diamine Chemical compound NCCNCCN1CCNCC1 WBIWIXJUBVWKLS-UHFFFAOYSA-N 0.000 description 1
- FEBWTDCQAJKUFJ-UHFFFAOYSA-N n'-[2-[ethyl(piperazin-1-yl)amino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCN(CC)N1CCNCC1 FEBWTDCQAJKUFJ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical class O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07103295.7 | 2007-03-01 | ||
| EP07103295 | 2007-03-01 | ||
| PCT/EP2008/052413 WO2008104582A2 (de) | 2007-03-01 | 2008-02-28 | Neues verfahren zur herstellung von teta über eddn |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2009136185A RU2009136185A (ru) | 2011-04-10 |
| RU2472772C2 true RU2472772C2 (ru) | 2013-01-20 |
Family
ID=39433821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009136185/04A RU2472772C2 (ru) | 2007-03-01 | 2008-02-28 | Способ получения триэтилентетрамина (тэта) через этилендиаминдиацетонитрил (эддн) |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8299249B2 (https=) |
| EP (2) | EP2129651B1 (https=) |
| JP (1) | JP5415287B2 (https=) |
| KR (1) | KR20090122435A (https=) |
| CN (1) | CN101622224B (https=) |
| RU (1) | RU2472772C2 (https=) |
| WO (1) | WO2008104582A2 (https=) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2478092C2 (ru) * | 2007-03-01 | 2013-03-27 | Басф Се | Способ получения смесей этиленаминов |
| JP5377335B2 (ja) * | 2007-03-01 | 2013-12-25 | ビーエーエスエフ ソシエタス・ヨーロピア | テトラエチレンペンタアミンの製造方法 |
| ES2390626T3 (es) * | 2007-03-01 | 2012-11-14 | Basf Se | Método de preparación de trietilentetraamina |
| JP5480276B2 (ja) | 2008-10-06 | 2014-04-23 | ユニオン カーバイド ケミカルズ アンド プラスティックス テクノロジー エルエルシー | 担体として酸性混合金属酸化物を含む低金属（ニッケル及びレニウム）触媒組成物 |
| EP2356095B2 (en) | 2008-10-06 | 2017-09-27 | Union Carbide Chemicals & Plastics Technology LLC | Methods of making cyclic, n-amino functional triamines |
| JP5469173B2 (ja) | 2008-10-06 | 2014-04-09 | ユニオン カーバイド ケミカルズ アンド プラスティックス テクノロジー エルエルシー | 金属低配合、アルミナ担持触媒組成物及びアミノ化方法 |
| JP2012504610A (ja) | 2008-10-06 | 2012-02-23 | ユニオン カーバイド ケミカルズ アンド プラスティックス テクノロジー エルエルシー | エチレンアミンの製造方法 |
| WO2010069856A1 (de) | 2008-12-19 | 2010-06-24 | Basf Se | Verfahren zur herstellung von reinem triethanolamin (teoa) |
| US8586795B2 (en) | 2009-06-18 | 2013-11-19 | Basf Se | Methyl-substituted teta compounds |
| WO2011067226A1 (de) | 2009-12-02 | 2011-06-09 | Basf Se | Verfahren zur destillation von gemischen enthaltend ethylendiamin, n-methylethylendiamin und wasser und damit erhältliche gemische aus ethylendiamin und n-methylethylendiamin mit einem geringen n-methylethylendiamingehalt |
| WO2011107512A1 (en) * | 2010-03-02 | 2011-09-09 | Basf Se | The use of linear triethylentetramine as curing agent for epoxy resins |
| EP2557074A1 (en) * | 2011-08-11 | 2013-02-13 | Astellas Pharma Inc. | Process for the preparation of N,N,N',N'-tetrakis(3-aminopropyl)-1,4-butanediamine |
| CN103764614A (zh) * | 2011-08-31 | 2014-04-30 | 巴斯夫欧洲公司 | Eddn或edmn氢化反应出料的后处理方法 |
| WO2013030254A1 (de) * | 2011-08-31 | 2013-03-07 | Basf Se | Verfahren zur herstellung von teta und/oder deta |
| IN2014CN00796A (https=) | 2011-08-31 | 2015-04-03 | Basf Se | |
| WO2013030259A1 (de) * | 2011-08-31 | 2013-03-07 | Basf Se | Verfahren zur herstellung von teta |
| US20130053536A1 (en) * | 2011-08-31 | 2013-02-28 | Basf Se | Process for preparing eddn and/or edmn and a process for preparing deta and/or teta |
| JP2014525942A (ja) * | 2011-08-31 | 2014-10-02 | ビーエーエスエフ ソシエタス・ヨーロピア | Ｆａｃｈとｅｄａの反応によるｅｄｄｎおよび／またはｅｄｍｎの製造方法 |
| CN103764618A (zh) * | 2011-08-31 | 2014-04-30 | 巴斯夫欧洲公司 | 制备edfa和/或edmfa以及deta和/或teta的方法 |
| US8952156B2 (en) | 2011-08-31 | 2015-02-10 | Basf Se | Process for working up reaction outputs from the hydrogenation of EDDN or EDMN |
| WO2013030144A1 (de) * | 2011-08-31 | 2013-03-07 | Basf Se | Verfahren zur herstellung von eddn, edmn, teta und deta |
| WO2013030249A1 (de) * | 2011-08-31 | 2013-03-07 | Basf Se | Verfahren zur herstellung von aminen durch hydrierung von nitrilen |
| WO2013030255A1 (de) * | 2011-08-31 | 2013-03-07 | Basf Se | Verfahren zur herstellung von eddn und/oder edmn sowie verfahren zur herstellung von deta und/oder teta |
| US9012638B2 (en) | 2011-08-31 | 2015-04-21 | Basf Se | Process for preparing EDDN and/or EDMN by conversion of FACH and EDA |
| WO2013030023A1 (de) * | 2011-08-31 | 2013-03-07 | Basf Se | Verfahren zur herstellung von eddn und/oder edmn sowie ein verfahren zur herstellung von deta und/oder teta |
| US8946459B2 (en) | 2011-08-31 | 2015-02-03 | Basf Se | Process for preparing EDDN and/or EDMN by reacting EDFA and/or EDMFA with HCN |
| US9096497B2 (en) | 2011-08-31 | 2015-08-04 | Basf Se | Process for preparing EDDN and EDMN |
| WO2013030143A1 (de) | 2011-08-31 | 2013-03-07 | Basf Se | Verfahren zur herstellung von eddn und/edmn |
| JP2017500386A (ja) | 2013-12-02 | 2017-01-05 | ダウ グローバル テクノロジーズ エルエルシー | 高分子量の分岐鎖非環式ポリアルキレンアミン及びその混合物の調製 |
| US9888584B2 (en) | 2014-12-31 | 2018-02-06 | Invensas Corporation | Contact structures with porous networks for solder connections, and methods of fabricating same |
| BR112018014272B1 (pt) | 2016-02-12 | 2021-12-28 | Akzo Nobel Chemicals International B.V. | Processo de preparação de etilenoaminas |
| MX390660B (es) * | 2016-02-12 | 2025-03-21 | Akzo Nobel Chemicals Int Bv | Proceso para preparar etilenaminas superiores y derivados de etilenamina. |
| BR112018014270B1 (pt) | 2016-02-12 | 2022-10-11 | Akzo Nobel Chemicals International B.V. | Processo de preparação de etilenoaminas |
| TWI762669B (zh) | 2017-07-10 | 2022-05-01 | 荷蘭商安科智諾貝爾化學國際公司 | 製造較高分子量伸乙基胺之方法 |
| TWI762670B (zh) * | 2017-07-10 | 2022-05-01 | 荷蘭商安科智諾貝爾化學國際公司 | 製備較高分子量伸乙基胺或其脲衍生物之方法 |
| US11339117B2 (en) | 2017-10-27 | 2022-05-24 | Basf Se | Method for the production of ethyleneamines |
| CN111278802A (zh) | 2017-10-27 | 2020-06-12 | 巴斯夫欧洲公司 | 制备亚乙基胺的方法 |
| JP7277455B2 (ja) | 2017-10-27 | 2023-05-19 | ビーエーエスエフ ソシエタス・ヨーロピア | Ｅｄａ含有混合物からのｎ－メチルエチレンジアミンの分離除去 |
| JP7268016B2 (ja) | 2017-10-27 | 2023-05-02 | ビーエーエスエフ ソシエタス・ヨーロピア | エチレンアミンの製造方法 |
| CN109490453A (zh) * | 2018-11-06 | 2019-03-19 | 广东省安全生产技术中心有限公司 | 一种三乙烯四胺的分离鉴定方法 |
| CN113924286A (zh) * | 2019-06-13 | 2022-01-11 | 陶氏环球技术有限责任公司 | 制备乙二胺四乙酸 |
| JP2023510492A (ja) | 2019-12-13 | 2023-03-14 | ビーエーエスエフ ソシエタス・ヨーロピア | Ｅｄａ含有混合物からのｎ－メチルエチレンジアミンの分離 |
| CA3201514A1 (en) * | 2020-12-16 | 2022-06-23 | Nouryon Chemicals International B.V. | Manufacture of nitrile compounds |
| CN119451938A (zh) | 2022-06-29 | 2025-02-14 | 巴斯夫欧洲公司 | 用于制造亚乙基胺的方法 |
| WO2024002740A1 (en) | 2022-06-29 | 2024-01-04 | Basf Se | Method for manufacture of ethyleneamines |
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2008
- 2008-02-28 US US12/529,072 patent/US8299249B2/en not_active Expired - Fee Related
- 2008-02-28 JP JP2009551210A patent/JP5415287B2/ja not_active Expired - Fee Related
- 2008-02-28 KR KR1020097018164A patent/KR20090122435A/ko not_active Withdrawn
- 2008-02-28 EP EP08717210.2A patent/EP2129651B1/de not_active Not-in-force
- 2008-02-28 RU RU2009136185/04A patent/RU2472772C2/ru not_active IP Right Cessation
- 2008-02-28 WO PCT/EP2008/052413 patent/WO2008104582A2/de not_active Ceased
- 2008-02-28 EP EP12183433.7A patent/EP2537835B1/de not_active Not-in-force
- 2008-02-28 CN CN200880006798.3A patent/CN101622224B/zh not_active Expired - Fee Related
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| SU276964A1 (ru) * | Способ получения эtилehдиamиh-n,n'-диуkcуchoикислоты | |||
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2129651A2 (de) | 2009-12-09 |
| JP5415287B2 (ja) | 2014-02-12 |
| US8299249B2 (en) | 2012-10-30 |
| EP2537835B1 (de) | 2014-04-30 |
| KR20090122435A (ko) | 2009-11-30 |
| EP2537835A1 (de) | 2012-12-26 |
| US20100121064A1 (en) | 2010-05-13 |
| CN101622224B (zh) | 2015-10-07 |
| WO2008104582A3 (de) | 2009-02-12 |
| JP2010520170A (ja) | 2010-06-10 |
| WO2008104582A2 (de) | 2008-09-04 |
| EP2129651B1 (de) | 2013-04-10 |
| CN101622224A (zh) | 2010-01-06 |
| RU2009136185A (ru) | 2011-04-10 |
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