CA1128069A - Hydrogenation of aliphatic nitriles to primary amines - Google Patents
Hydrogenation of aliphatic nitriles to primary aminesInfo
- Publication number
- CA1128069A CA1128069A CA344,191A CA344191A CA1128069A CA 1128069 A CA1128069 A CA 1128069A CA 344191 A CA344191 A CA 344191A CA 1128069 A CA1128069 A CA 1128069A
- Authority
- CA
- Canada
- Prior art keywords
- solvent
- nitriles
- nitrile
- hydrogen
- aliphatic
- 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.)
- Expired
Links
- -1 aliphatic nitriles Chemical class 0.000 title claims abstract description 16
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 8
- 150000003141 primary amines Chemical class 0.000 title description 8
- 150000002825 nitriles Chemical class 0.000 claims abstract description 28
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000002904 solvent Substances 0.000 claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 19
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 8
- 239000010941 cobalt Substances 0.000 claims abstract description 8
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims abstract description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 125000005237 alkyleneamino group Chemical group 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- VTHRQKSLPFJQHN-UHFFFAOYSA-N 3-[2-(2-cyanoethoxy)ethoxy]propanenitrile Chemical group N#CCCOCCOCCC#N VTHRQKSLPFJQHN-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 1
- 125000005219 aminonitrile group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229930189585 ingamine Natural products 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring 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
- C07C209/44—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
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)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8,315 | 1979-02-01 | ||
| US06/008,315 US4235821A (en) | 1979-02-01 | 1979-02-01 | Hydrogenation of aliphatic nitriles to primary amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1128069A true CA1128069A (en) | 1982-07-20 |
Family
ID=21730952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA344,191A Expired CA1128069A (en) | 1979-02-01 | 1980-01-22 | Hydrogenation of aliphatic nitriles to primary amines |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4235821A (enExample) |
| JP (1) | JPS55122744A (enExample) |
| BE (1) | BE881482A (enExample) |
| CA (1) | CA1128069A (enExample) |
| DE (1) | DE3003729A1 (enExample) |
| FR (1) | FR2447900B1 (enExample) |
| GB (1) | GB2042529B (enExample) |
| IT (1) | IT1193368B (enExample) |
| NL (1) | NL8000622A (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4721811A (en) * | 1985-08-26 | 1988-01-26 | W. R. Grace & Co. | Synthesis of aliphatic polyamines |
| US4739120A (en) * | 1986-08-21 | 1988-04-19 | The Dow Chemical Company | Process for the hydrogenation of nitriles to primary amines |
| US5097072A (en) * | 1990-02-05 | 1992-03-17 | W.R. Grace & Co.-Conn. | Preparation of polyamines |
| US5034560A (en) * | 1990-10-19 | 1991-07-23 | The Standard Oil Company | Synthesis of ethylamines |
| US5105015A (en) * | 1991-06-04 | 1992-04-14 | W. R. Grace & Co.-Conn. | Synthesis of non-cyclic aliphatic polyamines |
| US5286906A (en) * | 1991-09-25 | 1994-02-15 | Mitsubishi Kasei Corporation | Process for the preparation of 3-aminomethyl-3,5,5-trialkylcyclohexylamine |
| US5354343A (en) * | 1992-08-31 | 1994-10-11 | Shell Oil Company | Gasoline composition |
| US5629451A (en) * | 1994-06-30 | 1997-05-13 | Chemical Research & Licensing Company | Reduction of nitrile contaminants by selective hydrogenation |
| US5874625A (en) * | 1996-11-04 | 1999-02-23 | Henkel Corporation | Process to hydrogenate organic nitriles to primary amines |
| JP5415287B2 (ja) * | 2007-03-01 | 2014-02-12 | ビーエーエスエフ ソシエタス・ヨーロピア | Ｅｄｄｎを経由するｔｅｔａの新規製法 |
| ES2390626T3 (es) * | 2007-03-01 | 2012-11-14 | Basf Se | Método de preparación de trietilentetraamina |
| KR20090122434A (ko) * | 2007-03-01 | 2009-11-30 | 바스프 에스이 | 에틸렌아민의 제조 방법 |
| WO2008104551A1 (de) * | 2007-03-01 | 2008-09-04 | Basf Se | Verfahren zur herstellung von tetraethylenpentaamin |
| KR20090122436A (ko) * | 2007-03-01 | 2009-11-30 | 바스프 에스이 | 에틸렌디아민의 제조 방법 |
| JP5415286B2 (ja) * | 2007-03-01 | 2014-02-12 | ビーエーエスエフ ソシエタス・ヨーロピア | エチレンアミン混合物の製造方法 |
| JP2010520167A (ja) * | 2007-03-01 | 2010-06-10 | ビーエーエスエフ ソシエタス・ヨーロピア | 原料ａａｎからのエチレンアミンの製造方法 |
| WO2013184827A1 (en) * | 2012-06-05 | 2013-12-12 | Pastine Stefan J | Synthesis of and compositions containing diaminoacetals and diaminoketals |
| TWI565686B (zh) * | 2015-11-26 | 2017-01-11 | 南亞塑膠工業股份有限公司 | 一種ｎ，ｎ’－雙（３－胺基丙基）－１，２－乙二胺的製備方法 |
| US10919839B2 (en) | 2017-07-11 | 2021-02-16 | Aditya Birla Chemicals (Usa) Llc | Silicon-containing compositions and their methods of use |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1049388A (fr) * | 1951-04-30 | 1953-12-29 | Clyon Spa | Procédé pour l'hydrogénation de di-nitriles aliphatiques sous basse presssion et basse température |
| US3372195A (en) * | 1964-05-04 | 1968-03-05 | Dow Chemical Co | Reduction of nitriles to primary amines |
| GB1125706A (en) * | 1965-01-20 | 1968-08-28 | Ici Ltd | Process for the production of hexamethylene diamine |
| DE1593764A1 (de) * | 1967-02-11 | 1970-12-10 | Basf Ag | Verfahren zur Herstellung von 1,4-Alkylendiaminen |
| DE1793028B2 (de) * | 1968-07-25 | 1973-10-31 | Arkadij A. Moskau Artemjew | Verfahren zur Herstellung von Hexamethylendiamin |
| DE2004405A1 (de) * | 1970-01-31 | 1971-08-05 | Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen | Verfahren zur Herstellung von 1,3 Propylendiaminen und Di (1,3 propylen) triaminen |
| BE794577A (fr) * | 1972-04-21 | 1973-07-26 | Du Pont | Procede pour supprimer la formation de diaminocyclohexane dans la fabrication de l'hexamethylenediamine |
| JPS5082003A (enExample) * | 1973-11-14 | 1975-07-03 | ||
| US3898286A (en) * | 1973-11-19 | 1975-08-05 | Phillips Petroleum Co | Catalytic hydrogenation of unsaturated dinitriles employing palladium and ruthenium as catalyst |
| US3896173A (en) * | 1973-11-19 | 1975-07-22 | Phillips Petroleum Co | Two stage catalytic hydrogenation of unsaturated dinitriles employing ruthenium, nickel or mixture thereof as catalytic agent |
| US3896174A (en) * | 1973-11-19 | 1975-07-22 | Phillips Petroleum Co | Catalytic hydrogenation of unsaturated dinitriles employing ruthenium, nickel or mixture thereof as catalytic agent |
| US3880928A (en) * | 1973-11-19 | 1975-04-29 | Phillips Petroleum Co | Catalytic hydrogenation of unsaturated dinitriles employing rhodium as catalytic agent |
| US3962337A (en) * | 1974-10-29 | 1976-06-08 | Phillips Petroleum Company | Hydrogenation of unsaturated dinitriles for employing palladium and ruthenium catalyst in aqueous tertiary alkanol |
| JPS5915898B2 (ja) * | 1975-09-23 | 1984-04-12 | 旭化成株式会社 | 低級ジアルキルアミンおよび飽和環状イミンの製造法 |
| IL53034A0 (en) * | 1976-10-18 | 1977-11-30 | Sun Oil Co | Hydrogenation of bis(2-cyanoethoxy) compounds |
-
1979
- 1979-02-01 US US06/008,315 patent/US4235821A/en not_active Expired - Lifetime
-
1980
- 1980-01-22 CA CA344,191A patent/CA1128069A/en not_active Expired
- 1980-01-22 IT IT19375/80A patent/IT1193368B/it active
- 1980-01-29 FR FR8001860A patent/FR2447900B1/fr not_active Expired
- 1980-01-30 JP JP884380A patent/JPS55122744A/ja active Granted
- 1980-01-30 GB GB8003192A patent/GB2042529B/en not_active Expired
- 1980-01-31 NL NL8000622A patent/NL8000622A/nl not_active Application Discontinuation
- 1980-01-31 BE BE0/199216A patent/BE881482A/fr not_active IP Right Cessation
- 1980-02-01 DE DE19803003729 patent/DE3003729A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IT8019375A0 (it) | 1980-01-22 |
| FR2447900B1 (fr) | 1985-08-02 |
| BE881482A (fr) | 1980-07-31 |
| US4235821A (en) | 1980-11-25 |
| IT1193368B (it) | 1988-06-15 |
| FR2447900A1 (fr) | 1980-08-29 |
| GB2042529A (en) | 1980-09-24 |
| JPH0152381B2 (enExample) | 1989-11-08 |
| NL8000622A (nl) | 1980-08-05 |
| DE3003729A1 (de) | 1980-08-14 |
| GB2042529B (en) | 1983-05-18 |
| JPS55122744A (en) | 1980-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |