JPS59130839A - ジエチレントリアミンの接触的製造方法 - Google Patents
ジエチレントリアミンの接触的製造方法Info
- Publication number
- JPS59130839A JPS59130839A JP58245617A JP24561783A JPS59130839A JP S59130839 A JPS59130839 A JP S59130839A JP 58245617 A JP58245617 A JP 58245617A JP 24561783 A JP24561783 A JP 24561783A JP S59130839 A JPS59130839 A JP S59130839A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- ethylenediamine
- diethylenetriamine
- nickel
- 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.)
- Granted
Links
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title description 7
- 230000003197 catalytic effect Effects 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims description 42
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 39
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 29
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 25
- 229920000768 polyamine Polymers 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 17
- 229910017052 cobalt Inorganic materials 0.000 claims description 15
- 239000010941 cobalt Substances 0.000 claims description 15
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 15
- 229910052759 nickel Inorganic materials 0.000 claims description 15
- 239000000376 reactant Substances 0.000 claims description 14
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052703 rhodium Inorganic materials 0.000 claims description 11
- 239000010948 rhodium Substances 0.000 claims description 11
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- 239000007868 Raney catalyst Substances 0.000 claims description 5
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 5
- 229920001281 polyalkylene Polymers 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 229910052750 molybdenum Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AWGBWLXGUPTXHF-UHFFFAOYSA-N 2,2,2-trifluoro-n-methyl-n-(2,2,2-trifluoroacetyl)acetamide Chemical compound FC(F)(F)C(=O)N(C)C(=O)C(F)(F)F AWGBWLXGUPTXHF-UHFFFAOYSA-N 0.000 description 1
- 235000001270 Allium sibiricum Nutrition 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 101100227721 Rattus norvegicus Frk gene Proteins 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- -1 polyethylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- C07C209/64—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)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/454,485 US4568746A (en) | 1982-12-29 | 1982-12-29 | Catalytic preparation of diethylenetriamine |
| US454485 | 1999-12-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59130839A true JPS59130839A (ja) | 1984-07-27 |
| JPH0240056B2 JPH0240056B2 (2) | 1990-09-10 |
Family
ID=23804798
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58245617A Granted JPS59130839A (ja) | 1982-12-29 | 1983-12-28 | ジエチレントリアミンの接触的製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4568746A (2) |
| EP (1) | EP0115637B1 (2) |
| JP (1) | JPS59130839A (2) |
| CA (1) | CA1212113A (2) |
| DE (1) | DE3369125D1 (2) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007500731A (ja) * | 2003-08-01 | 2007-01-18 | ビーエーエスエフ アクチェンゲゼルシャフト | エチレンアミンの製造方法 |
| JP2009526801A (ja) * | 2006-02-14 | 2009-07-23 | ビーエーエスエフ ソシエタス・ヨーロピア | モノエチレングリコール（ｍｅｇ）からのエチレンアミン及びエタノールアミンの製造方法 |
| JP2009526810A (ja) * | 2006-02-14 | 2009-07-23 | ビーエーエスエフ ソシエタス・ヨーロピア | 触媒の存在でモノエチレングリコール及びアンモニアの水素化アミノ化によるエチレンアミン及びエタノールアミンの製造方法 |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4625030A (en) * | 1984-05-23 | 1986-11-25 | Union Carbide Corporation | Potentiated nickel catalysts for amination |
| JPH0830044B2 (ja) * | 1987-09-24 | 1996-03-27 | 三菱瓦斯化学株式会社 | ジオクタメチレントリアミンの製造法 |
| US5196588A (en) * | 1987-09-30 | 1993-03-23 | Union Carbide Chemicals & Plastics Technology Corporation | Ethylenediamine and diethylenetriamine producers composition and method for producing same |
| US4977266A (en) * | 1987-09-30 | 1990-12-11 | Union Carbide Chemicals And Plastics Company Inc. | Aminoethylethanolamine and ethylenediamine producers composition and method for producing same |
| US4973692A (en) * | 1987-09-30 | 1990-11-27 | Union Carbide Chemicals And Plastics Company Inc. | Aminoethylethanolamine producers composition and method for producing same |
| US5202490A (en) * | 1987-09-30 | 1993-04-13 | Union Carbide Chemicals & Plastics Technology Corporation | Process for thr manufacture of diethylenetriamine and aminoethylethanolamine |
| US5068330A (en) * | 1987-09-30 | 1991-11-26 | Union Carbide Chemicals And Plastics Technology Corporation | Aminoethyethanolamine and ethylenediamine producers composition and method for producing same |
| US5202491A (en) * | 1987-09-30 | 1993-04-13 | Union Carbide Chemicals & Plastics Technology Corporation | Process for the manufacture of diethylenetriamine |
| US5068329A (en) * | 1987-09-30 | 1991-11-26 | Union Carbide Chemicals And Plastics Technology Corporation | Aminoethylethanolamine producers composition and method for producing same |
| US5166442A (en) * | 1988-12-20 | 1992-11-24 | The Dow Chemical Company | Catalytic reforming of alkyleneamines |
| US5210307A (en) * | 1988-12-20 | 1993-05-11 | The Dow Chemical Company | Catalytic reforming of alkyleneamines to linearly-extended polyalkylenepolyamines |
| US4996363A (en) * | 1988-12-20 | 1991-02-26 | The Dow Chemical Company | Catalytic reforming of alkyleneamines to linearly-extended polyalkylenepolyamines |
| 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 |
| DE102005047458A1 (de) * | 2005-09-30 | 2007-04-12 | Basf Ag | Verfahren zur Herstellung von Aminodiglykol (ADG) und Morpholin |
| DE502006005368D1 (de) * | 2005-09-30 | 2009-12-24 | Basf Se | Verfahren zur herstellung von ethylenaminen |
| CN101277922B (zh) * | 2005-09-30 | 2011-08-17 | 巴斯夫欧洲公司 | 生产亚乙基胺的方法 |
| DE102005048552A1 (de) * | 2005-10-11 | 2007-04-12 | Basf Ag | Verfahren zur Herstellung von Ethylenaminen |
| US8188318B2 (en) * | 2008-10-06 | 2012-05-29 | Union Carbide Chemicals & Plastics Technology Llc | Method of manufacturing ethyleneamines |
| EP2487151B1 (en) * | 2008-10-06 | 2015-09-02 | Dow Global Technologies LLC | Process for separating alkylethyleneamine(s) from ethyleneamine(s) compositions |
| EP2356095B2 (en) * | 2008-10-06 | 2017-09-27 | Union Carbide Chemicals & Plastics Technology LLC | Methods of making cyclic, n-amino functional triamines |
| JP5806116B2 (ja) * | 2008-10-06 | 2015-11-10 | 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 | 求核性化合物のトランスアルコキシル化 |
| 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 |
| CN102239002B (zh) | 2008-10-06 | 2013-10-30 | 联合碳化化学品及塑料技术公司 | 低金属负载的氧化铝载体的催化剂组合物和氨基化方法 |
| EP2344445B1 (en) * | 2008-10-06 | 2017-05-10 | 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 |
| 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 |
| WO2012064484A1 (en) | 2010-11-10 | 2012-05-18 | Dow Global Technologies Llc | Transamination of nitrogen-containing compounds to high molecular weight polyalkyleneamines |
| CN103159630B (zh) * | 2011-12-14 | 2015-05-20 | 中国科学院大连化学物理研究所 | 一种以乙醇胺和氨为原料制备乙二胺的方法 |
| WO2013101345A1 (en) | 2011-12-29 | 2013-07-04 | Dow Global Technologies Llc | Formation of higher molecular weight cyclic polyamine compounds from cyclic polyamine compounds |
| WO2013102097A2 (en) | 2011-12-29 | 2013-07-04 | Dow Global Technologies Llc | Cyclic amine compounds, compositions, and polyurethane foams made therefrom |
| US9611351B2 (en) | 2011-12-29 | 2017-04-04 | Dow Global Technologies Llc. | Amine polyether polyols and polyurethane foam compositions made from cyclic amine compounds |
| WO2015084619A1 (en) | 2013-12-02 | 2015-06-11 | Dow Global Technologies Llc | Preparation of high molecular weight, branched, acyclic polyalkyleneamines and mixtures thereof |
| US20220162152A1 (en) * | 2019-03-05 | 2022-05-26 | Basf Se | Preparation of polyalkylene-polyamines by reductive amination |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3714259A (en) * | 1970-08-20 | 1973-01-30 | Jefferson Chem Co Inc | Production of linear polyethylene polyamines |
| GB1508460A (en) * | 1974-08-16 | 1978-04-26 | Basf Ag | Manufacture of diethylenetriamine and triethylenetetramine from ethylenediamine |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2781399A (en) * | 1953-02-24 | 1957-02-12 | Armour & Co | Preparation of secondary amines |
| US2861995A (en) * | 1956-04-27 | 1958-11-25 | Dow Chemical Co | Process for the conversion of ethanolamine |
| DE1170960B (de) * | 1957-06-27 | 1964-05-27 | Dow Chemical Co | Kontinuierliches Verfahren zur Herstellung von Di- und Polyaminen |
| US3068290A (en) * | 1957-07-23 | 1962-12-11 | Electro Chimie Metal | Process of making ethylenediamine |
| US4036881A (en) * | 1975-06-02 | 1977-07-19 | Texaco Development Corporation | Preparation of polyalkylene polyamines |
-
1982
- 1982-12-29 US US06/454,485 patent/US4568746A/en not_active Expired - Lifetime
-
1983
- 1983-11-24 CA CA000441889A patent/CA1212113A/en not_active Expired
- 1983-12-28 DE DE8383113181T patent/DE3369125D1/de not_active Expired
- 1983-12-28 EP EP83113181A patent/EP0115637B1/en not_active Expired
- 1983-12-28 JP JP58245617A patent/JPS59130839A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3714259A (en) * | 1970-08-20 | 1973-01-30 | Jefferson Chem Co Inc | Production of linear polyethylene polyamines |
| GB1508460A (en) * | 1974-08-16 | 1978-04-26 | Basf Ag | Manufacture of diethylenetriamine and triethylenetetramine from ethylenediamine |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007500731A (ja) * | 2003-08-01 | 2007-01-18 | ビーエーエスエフ アクチェンゲゼルシャフト | エチレンアミンの製造方法 |
| JP2009526801A (ja) * | 2006-02-14 | 2009-07-23 | ビーエーエスエフ ソシエタス・ヨーロピア | モノエチレングリコール（ｍｅｇ）からのエチレンアミン及びエタノールアミンの製造方法 |
| JP2009526810A (ja) * | 2006-02-14 | 2009-07-23 | ビーエーエスエフ ソシエタス・ヨーロピア | 触媒の存在でモノエチレングリコール及びアンモニアの水素化アミノ化によるエチレンアミン及びエタノールアミンの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1212113A (en) | 1986-09-30 |
| DE3369125D1 (en) | 1987-02-19 |
| EP0115637B1 (en) | 1987-01-14 |
| EP0115637A1 (en) | 1984-08-15 |
| JPH0240056B2 (2) | 1990-09-10 |
| US4568746A (en) | 1986-02-04 |
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