DE2439275B2 - Verfahren zur Herstellung von Diäthylentriamin und Triäthylentetramin aus Äthylendiamin - Google Patents
Verfahren zur Herstellung von Diäthylentriamin und Triäthylentetramin aus ÄthylendiaminInfo
- Publication number
- DE2439275B2 DE2439275B2 DE19742439275 DE2439275A DE2439275B2 DE 2439275 B2 DE2439275 B2 DE 2439275B2 DE 19742439275 DE19742439275 DE 19742439275 DE 2439275 A DE2439275 A DE 2439275A DE 2439275 B2 DE2439275 B2 DE 2439275B2
- Authority
- DE
- Germany
- Prior art keywords
- ethylenediamine
- reaction
- triethylenetetramine
- diethylenetriamine
- piperazine
- 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- Withdrawn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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 title claims description 22
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 title claims description 19
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 230000008030 elimination Effects 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 22
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 235000002639 sodium chloride Nutrition 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229910017052 cobalt Inorganic materials 0.000 description 5
- 239000010941 cobalt Substances 0.000 description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000007098 aminolysis reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000010970 precious metal Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- -1 amine hydrochloride Chemical class 0.000 description 2
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- NGIMEWRJMGHZPG-UHFFFAOYSA-N n'-[2-(piperazin-1-ylamino)ethyl]ethane-1,2-diamine Chemical compound NCCNCCNN1CCNCC1 NGIMEWRJMGHZPG-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910000570 Cupronickel Inorganic materials 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- DPRMFUAMSRXGDE-UHFFFAOYSA-N ac1o530g Chemical compound NCCN.NCCN DPRMFUAMSRXGDE-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PFQOHNVNWRNBFW-UHFFFAOYSA-N n'-(2-aminoethyl)ethane-1,2-diamine;piperazine Chemical compound C1CNCCN1.NCCNCCN PFQOHNVNWRNBFW-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010626 work up procedure Methods 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742439275 DE2439275B2 (de) | 1974-08-16 | 1974-08-16 | Verfahren zur Herstellung von Diäthylentriamin und Triäthylentetramin aus Äthylendiamin |
| JP9768475A JPS5141308A (ja) | 1974-08-16 | 1975-08-13 | Echirenjiaminyorijechirentoriamin oyobi toriechirentetoraminoseizosuruhoho |
| FR7525327A FR2281920A1 (fr) | 1974-08-16 | 1975-08-14 | Procede de preparation de diethylenetriamine et de triethylenetetramine a partir d'ethylenediamine |
| GB3401875A GB1508460A (en) | 1974-08-16 | 1975-08-15 | Manufacture of diethylenetriamine and triethylenetetramine from ethylenediamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742439275 DE2439275B2 (de) | 1974-08-16 | 1974-08-16 | Verfahren zur Herstellung von Diäthylentriamin und Triäthylentetramin aus Äthylendiamin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2439275A1 DE2439275A1 (de) | 1976-03-04 |
| DE2439275B2 true DE2439275B2 (de) | 1978-09-21 |
Family
ID=5923322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742439275 Withdrawn DE2439275B2 (de) | 1974-08-16 | 1974-08-16 | Verfahren zur Herstellung von Diäthylentriamin und Triäthylentetramin aus Äthylendiamin |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5141308A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2439275B2 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2281920A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1508460A (cg-RX-API-DMAC10.html) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4216307A (en) * | 1977-09-29 | 1980-08-05 | Nippon Oil Company, Ltd. | Polyhexamethylenimine and process for its preparation |
| US4568746A (en) * | 1982-12-29 | 1986-02-04 | Union Carbide Corporation | Catalytic preparation of diethylenetriamine |
| US5410086A (en) * | 1989-06-27 | 1995-04-25 | Burgess; Lloyd M. | Selective preparation of diethylenetriamine |
| SE524126C2 (sv) * | 2001-07-24 | 2004-06-29 | Akzo Nobel Nv | Förfarande för framställning av dietylentriamin och högre polyetylenpolyaminer genom transaminering av etylendiamin |
| ATE344228T1 (de) | 2003-08-01 | 2006-11-15 | Basf Ag | Verfahren zur herstellung von ethylenaminen |
| DE10335991A1 (de) | 2003-08-01 | 2005-02-24 | Basf Ag | Verfahren zur Herstellung von Ethylenaminen |
| DE10359811A1 (de) * | 2003-12-19 | 2005-07-21 | Basf Ag | Verfahren zur Erhöhung der Raum-Zeit-Ausbeute (RZA) in einem Verfahren zur Herstellung eines symmetrischen sekundären Amins |
| DE502006005367D1 (de) | 2005-09-30 | 2009-12-24 | Basf Se | Verfahren zur herstellung von ethylenaminen |
| ATE448192T1 (de) | 2005-09-30 | 2009-11-15 | Basf Se | Verfahren zur herstellung von ethylenaminen |
| DE102005048552A1 (de) | 2005-10-11 | 2007-04-12 | Basf Ag | Verfahren zur Herstellung von Ethylenaminen |
| CN101384541B (zh) | 2006-02-14 | 2012-06-13 | 巴斯夫欧洲公司 | 在催化剂存在下通过单乙二醇和氨的氢化胺化生产亚乙基胺和乙醇胺的方法 |
| EP2029520B1 (de) | 2006-02-14 | 2013-07-31 | Basf Se | Verfahren zur herstellung von ethylenaminen und ethanolaminen aus monoethylenglykol (meg) |
| US8299249B2 (en) * | 2007-03-01 | 2012-10-30 | Basf Se | Method for producing TETA by means of EDDN |
| CN101675024B (zh) * | 2007-03-01 | 2013-07-10 | 巴斯夫欧洲公司 | 制备三亚乙基四胺的方法 |
| US8383861B2 (en) | 2008-10-06 | 2013-02-26 | Dow Global Technologies Llc | Methods for making ethanolamine(s) and ethyleneamine(s) from ethylene oxide and ammonia, and related methods |
| ES2444924T3 (es) | 2008-10-06 | 2014-02-27 | Union Carbide Chemicals & Plastics Technology Llc | Métodos para preparar triaminas N-aminofuncionales cíclicas |
| WO2010042164A2 (en) | 2008-10-06 | 2010-04-15 | Union Carbide Chemicals & Plastics Technology Llc | Transalkoxylation of nucleophilic compounds |
| WO2010042160A1 (en) * | 2008-10-06 | 2010-04-15 | Union Carbide Chemicals & Plastics Technology Llc | A process to selectively manufacture diethylenetriamine (deta) or other desirable ethylenamines via continuous transamination of ethylenediamine (eda), and other ethyleneamines over a heterogeneous catalyst system |
| EP2352585B1 (en) | 2008-10-06 | 2020-06-17 | Union Carbide Corporation | Low metal loaded, alumina supported, catalyst compositions and amination process |
| US8187997B2 (en) | 2008-10-06 | 2012-05-29 | Union Carbide Chemicals & Technology LLC | Low metal loaded, catalyst compositions including acidic mixed metal oxide as support |
| CN102224129B (zh) | 2008-10-06 | 2015-02-11 | 联合碳化化学品及塑料技术公司 | 制备乙撑胺的方法 |
| US9000217B2 (en) | 2010-11-10 | 2015-04-07 | Dow Global Technologies Llc | Transamination of nitrogen-containing compounds to high molecular weight polyalkyleneamines |
| US8993759B2 (en) | 2010-11-10 | 2015-03-31 | Dow Global Technologies Llc | Transamination of nitrogen-containing compounds to make cyclic and cyclic/acyclic polyamine mixtures |
| CN104245683B (zh) | 2011-12-29 | 2017-06-30 | 陶氏环球技术有限责任公司 | 环胺化合物、组合物及由其制备的聚氨酯泡沫体 |
| WO2013102053A1 (en) | 2011-12-29 | 2013-07-04 | Dow Global Technologies Llc | Amine polyether polyols and polyurethane foam compositions made from cyclic amine compounds |
| BR112014016218A8 (pt) | 2011-12-29 | 2017-07-04 | Dow Global Technologies Llc | produto de reação, composição de reação e método para manufaturar uma amina polifuncional |
| JP2016514178A (ja) | 2013-02-28 | 2016-05-19 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ポリアミン及びその製造方法 |
| US8987518B2 (en) | 2013-02-28 | 2015-03-24 | Basf Se | Polyamines and process for preparation thereof |
| 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 |
| EP3110872A1 (de) | 2014-02-26 | 2017-01-04 | Basf Se | Verfahren zur herstellung von polyaminen |
| WO2022179864A1 (en) | 2021-02-25 | 2022-09-01 | Basf Se | Process for the production of polyalkylene-polyamines by condensation of alkylene-diamines |
-
1974
- 1974-08-16 DE DE19742439275 patent/DE2439275B2/de not_active Withdrawn
-
1975
- 1975-08-13 JP JP9768475A patent/JPS5141308A/ja active Pending
- 1975-08-14 FR FR7525327A patent/FR2281920A1/fr active Granted
- 1975-08-15 GB GB3401875A patent/GB1508460A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2439275A1 (de) | 1976-03-04 |
| FR2281920B3 (cg-RX-API-DMAC10.html) | 1978-04-07 |
| JPS5141308A (ja) | 1976-04-07 |
| FR2281920A1 (fr) | 1976-03-12 |
| GB1508460A (en) | 1978-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| OI | Miscellaneous see part 1 | ||
| BHN | Withdrawal |