DE102005004854A1 - Verfahren zur Herstellung von Bis(3-aminopropyl)amin (Dipropylentriamin, DPTA) - Google Patents
Verfahren zur Herstellung von Bis(3-aminopropyl)amin (Dipropylentriamin, DPTA) Download PDFInfo
- Publication number
- DE102005004854A1 DE102005004854A1 DE102005004854A DE102005004854A DE102005004854A1 DE 102005004854 A1 DE102005004854 A1 DE 102005004854A1 DE 102005004854 A DE102005004854 A DE 102005004854A DE 102005004854 A DE102005004854 A DE 102005004854A DE 102005004854 A1 DE102005004854 A1 DE 102005004854A1
- Authority
- DE
- Germany
- Prior art keywords
- column
- pda
- reaction
- reaction zone
- dpta
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 69
- WYMDDFRYORANCC-UHFFFAOYSA-N 2-[[3-[bis(carboxymethyl)amino]-2-hydroxypropyl]-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)CN(CC(O)=O)CC(O)=O WYMDDFRYORANCC-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 title claims abstract description 5
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 title claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 78
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002638 heterogeneous catalyst Substances 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims description 34
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
- 238000004821 distillation Methods 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 238000012856 packing Methods 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 238000009835 boiling Methods 0.000 claims description 12
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 9
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012876 carrier material Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052702 rhenium Inorganic materials 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 230000003014 reinforcing effect Effects 0.000 claims description 2
- 238000000066 reactive distillation Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 9
- 230000003197 catalytic effect Effects 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 150000003141 primary amines Chemical class 0.000 description 7
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 6
- 150000003335 secondary amines Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- -1 ethylene amines Chemical class 0.000 description 5
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- BELZJFWUNQWBES-UHFFFAOYSA-N caldopentamine Chemical compound NCCCNCCCNCCCNCCCN BELZJFWUNQWBES-UHFFFAOYSA-N 0.000 description 4
- 238000006471 dimerization reaction Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- GEIAQOFPUVMAGM-UHFFFAOYSA-N ZrO Inorganic materials [Zr]=O GEIAQOFPUVMAGM-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008362 aminopropionitriles Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000010987 cubic zirconia Substances 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000010457 zeolite Substances 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
- C07C209/64—Preparation of compounds containing amino groups bound to a carbon skeleton by disproportionation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005004854A DE102005004854A1 (de) | 2005-02-01 | 2005-02-01 | Verfahren zur Herstellung von Bis(3-aminopropyl)amin (Dipropylentriamin, DPTA) |
| PCT/EP2006/050592 WO2006082203A1 (de) | 2005-02-01 | 2006-02-01 | Verfahren zur herstellung von bis(3-aminopropyl)amin (dipropylentriamin, dpta) |
| CNA2006800038248A CN101111468A (zh) | 2005-02-01 | 2006-02-01 | 制备双（3-氨基丙基）胺（二亚丙基三胺，dpta）的方法 |
| EP06707954A EP1846358A1 (de) | 2005-02-01 | 2006-02-01 | Verfahren zur herstellung von bis(3-aminopropyl)amin (dipropylentriamin, dpta) |
| US11/815,179 US20080132725A1 (en) | 2005-02-01 | 2006-02-01 | Method for Producing Bis-[(3-Dimethylamino)Propyl]Amine (Dipropylene Triamine, Dpta) |
| JP2007552667A JP2008528558A (ja) | 2005-02-01 | 2006-02-01 | ビス（３−アミノプロピル）アミン（ジプロピレントリアミン、ｄｐｔａ）の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005004854A DE102005004854A1 (de) | 2005-02-01 | 2005-02-01 | Verfahren zur Herstellung von Bis(3-aminopropyl)amin (Dipropylentriamin, DPTA) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102005004854A1 true DE102005004854A1 (de) | 2006-08-17 |
Family
ID=36406022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102005004854A Withdrawn DE102005004854A1 (de) | 2005-02-01 | 2005-02-01 | Verfahren zur Herstellung von Bis(3-aminopropyl)amin (Dipropylentriamin, DPTA) |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20080132725A1 (https=) |
| EP (1) | EP1846358A1 (https=) |
| JP (1) | JP2008528558A (https=) |
| CN (1) | CN101111468A (https=) |
| DE (1) | DE102005004854A1 (https=) |
| WO (1) | WO2006082203A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005004853A1 (de) * | 2005-02-01 | 2006-08-03 | Basf Ag | Verfahren zur Herstellung von Bis-[(3-Dimethylamino)propyl]amin (BisDMAPA) |
| CN101817753B (zh) * | 2010-04-01 | 2012-09-12 | 大连理工大学 | 一种n-(3-氨基丙基)-1,3-丙二胺的制备方法 |
| US9000217B2 (en) | 2010-11-10 | 2015-04-07 | Dow Global Technologies Llc | Transamination of nitrogen-containing compounds to high molecular weight polyalkyleneamines |
| BR112013022942A2 (pt) * | 2011-03-22 | 2016-12-06 | Basf Se | processo para hidrogenar nitrilas orgânicas |
| WO2013102097A2 (en) | 2011-12-29 | 2013-07-04 | Dow Global Technologies Llc | Cyclic amine compounds, compositions, and polyurethane foams made therefrom |
| WO2013101345A1 (en) | 2011-12-29 | 2013-07-04 | Dow Global Technologies Llc | Formation of higher molecular weight cyclic polyamine compounds from cyclic polyamine compounds |
| WO2013102053A1 (en) | 2011-12-29 | 2013-07-04 | Dow Global Technologies Llc | Amine polyether polyols and polyurethane foam compositions made from cyclic amine compounds |
| CN102614894B (zh) * | 2012-03-04 | 2013-11-13 | 浙江建业化工股份有限公司 | 用于异丙胺合成二异丙胺的负载型催化剂及其制法和用途 |
| 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 |
| CN105992788A (zh) | 2014-02-26 | 2016-10-05 | 巴斯夫欧洲公司 | 制备聚胺的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0478428B1 (fr) * | 1990-09-25 | 1995-03-08 | Institut Français du Pétrole | Procédé de préparation d'oxyde borique par hydrolyse du borate de méthyle et sa mise en oeuvre dans l'oxydation d'hydrocarbures saturées en alcools |
| KR960022419A (ko) * | 1994-12-29 | 1996-07-18 | 김준웅 | 반응증류를 이용하여 메틸아세테이트로부터 초산과 메탄올을 제조하는 방법 및 장치 |
| DE10129908A1 (de) * | 2001-06-21 | 2003-01-02 | Basf Ag | Verfahren zur Herstellung von sekundären Aminen aus primären Aminen |
| DE10159821A1 (de) * | 2001-12-06 | 2003-06-18 | Basf Ag | Vorrichtung und Verfahren zur Durchführung von heterogen katalysierter Reaktivdestillationen, insbesondere zur Herstellung von Pseudoionen |
| US7098366B2 (en) * | 2001-12-06 | 2006-08-29 | Basf Aktiengesellschaft | Supported metal oxides as catalysts for aldol condensations |
| DE10261195A1 (de) * | 2002-12-20 | 2004-07-01 | Basf Ag | Verfahren zur Herstellung eines symmetrischen sekundären Amins |
| US7393978B2 (en) * | 2003-08-01 | 2008-07-01 | Basf Aktiengesellschaft | Method for producing ethylene-amines |
-
2005
- 2005-02-01 DE DE102005004854A patent/DE102005004854A1/de not_active Withdrawn
-
2006
- 2006-02-01 JP JP2007552667A patent/JP2008528558A/ja not_active Withdrawn
- 2006-02-01 EP EP06707954A patent/EP1846358A1/de not_active Withdrawn
- 2006-02-01 US US11/815,179 patent/US20080132725A1/en not_active Abandoned
- 2006-02-01 CN CNA2006800038248A patent/CN101111468A/zh active Pending
- 2006-02-01 WO PCT/EP2006/050592 patent/WO2006082203A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP1846358A1 (de) | 2007-10-24 |
| CN101111468A (zh) | 2008-01-23 |
| JP2008528558A (ja) | 2008-07-31 |
| US20080132725A1 (en) | 2008-06-05 |
| WO2006082203A1 (de) | 2006-08-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1654214B1 (de) | Verfahren zur herstellung von ethylenaminen | |
| EP2029520B1 (de) | Verfahren zur herstellung von ethylenaminen und ethanolaminen aus monoethylenglykol (meg) | |
| EP1654215B1 (de) | Verfahren zur herstellung von ethylenaminen | |
| EP1986990B1 (de) | Verfahren zur herstellung von ethylenaminen und ethanolaminen durch hydrierende aminierung von monoethylenglykol und ammoniak in gegenwart eines katalysators | |
| EP3700884B1 (de) | Verfahren zur herstellung von ethylenaminen | |
| DE102005004854A1 (de) | Verfahren zur Herstellung von Bis(3-aminopropyl)amin (Dipropylentriamin, DPTA) | |
| EP1986991B1 (de) | Verfahren zur destillativen auftrennung von gemischen, enthaltend monoethylenglykol und diethylentriamin | |
| WO2013178693A1 (de) | Verfahren zur herstellung eines mono-n-alkyl-piperazins | |
| EP1846357B1 (de) | Verfahren zur herstellung von bis-[(3-dimethylamino)propyl]amin (bisdmapa) | |
| WO2013075974A1 (de) | Verfahren zur herstellung von ethylaminen und mono-iso-propylamin (mipa) | |
| EP2635544A1 (de) | Verfahren zur herstellung eines phenylcyclohexans | |
| WO2014184039A1 (de) | Verfahren zur herstellung von n-alkyl-piperazinen | |
| WO2012000952A1 (de) | Verfahren zur herstellung von tri-n-propylamin (tpa) | |
| WO2007036498A1 (de) | Verfahren zur herstellung von ethylenaminen | |
| DE102010040427A1 (de) | Verfahren zur Herstellung von Mono-n-Octylamin (MOA) | |
| EP1934166B1 (de) | Verfahren zur herstellung von ethylenaminen | |
| WO2012013563A1 (de) | Dmapn mit niedrigem dgn-gehalt und ein verfahren zur herstellung von dmapa aus dmapn mit niedrigem dgn-gehalt | |
| DE102005047464A1 (de) | Verfahren zur Herstellung von Ethylenaminen | |
| DE10336003A1 (de) | Verfahren zur Herstellung von Ethylenaminen | |
| DE102004030645A1 (de) | Verfahren zur Herstellung von Ethylenaminen | |
| EP1928816A1 (de) | Verfahren zur herstellung von xylylendiamin | |
| EP2556045A1 (de) | Verfahren zur herstellung von unsymmetrischen sekundären tert.-butylaminen in der gasphase | |
| DE2725669C3 (de) | Verfahren zur Herstellung von sekundären Aminen | |
| WO2018050554A1 (de) | Cyanethylierte methylcylohexandiamin- (mcda) und toluoldiamin- (tda) derivate | |
| DE102005052376A1 (de) | Verfahren zur Herstellung von Ethylenaminen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |