CN100584820C - A kind of method for preparing 3-alkoxypropylamine - Google Patents
A kind of method for preparing 3-alkoxypropylamine Download PDFInfo
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- CN100584820C CN100584820C CN 200710062128 CN200710062128A CN100584820C CN 100584820 C CN100584820 C CN 100584820C CN 200710062128 CN200710062128 CN 200710062128 CN 200710062128 A CN200710062128 A CN 200710062128A CN 100584820 C CN100584820 C CN 100584820C
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- alcohol
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- propyl amine
- alkoxyl group
- consumption
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- 238000000034 method Methods 0.000 title claims abstract description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 36
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000003756 stirring Methods 0.000 claims abstract description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000001816 cooling Methods 0.000 claims abstract description 15
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 3
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 23
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 4
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 claims description 3
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004440 Isodecyl alcohol Substances 0.000 claims description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 2
- 229960000541 cetyl alcohol Drugs 0.000 claims description 2
- 238000007278 cyanoethylation reaction Methods 0.000 claims description 2
- 238000006073 displacement reaction Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003333 secondary alcohols Chemical class 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000000463 material Substances 0.000 abstract description 4
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 15
- 230000009466 transformation Effects 0.000 description 13
- 238000007599 discharging Methods 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 230000032683 aging Effects 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000012423 maintenance Methods 0.000 description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- ZRJOUVOXPWNFOF-UHFFFAOYSA-N 3-dodecoxypropan-1-amine Chemical compound CCCCCCCCCCCCOCCCN ZRJOUVOXPWNFOF-UHFFFAOYSA-N 0.000 description 2
- ARSMZQPQPVWIFJ-UHFFFAOYSA-N 3-dodecoxypropanenitrile Chemical compound CCCCCCCCCCCCOCCC#N ARSMZQPQPVWIFJ-UHFFFAOYSA-N 0.000 description 2
- 241000790917 Dioxys <bee> Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000008431 aliphatic amides Chemical class 0.000 description 2
- 125000006231 alkoxy propyl group Chemical group 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- -1 sterilant Substances 0.000 description 2
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical class CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- IOIYHMWPEVCBRV-UHFFFAOYSA-N CCC(CCCCC(C)C)[O] Chemical compound CCC(CCCCC(C)C)[O] IOIYHMWPEVCBRV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
一种制备3-烷氧基丙胺的方法是将醇和氢氧化钠水溶液按氢氧化钠用量为醇用量的0.2～1.2wt%混合后搅拌，加热至40-70℃，逐滴加入与醇等摩尔的丙烯腈，滴完丙烯腈后反应1.5-5h，待降温后得到3-烷氧基丙腈；将3-烷氧基丙腈、骨架镍和H2O按比例置于高压釜中，通入氢气至釜中置换釜内空气，搅拌，升温至100～160℃后，向釜中通入氨气和氢气，然后反应2～5h后，降温出料，料液除去催化剂即为产品。本发明具有应条件温和、工艺简单、产率高的优点。A method for preparing 3-alkoxypropylamine is to mix alcohol and sodium hydroxide aqueous solution according to the amount of sodium hydroxide being 0.2-1.2wt% of the alcohol amount, mix them, heat to 40-70°C, and add alcohol and alcohol equimolar acrylonitrile, react for 1.5-5h after dripping acrylonitrile, and obtain 3-alkoxypropionitrile after cooling down; put 3-alkoxypropionitrile, skeleton nickel and H2O in an autoclave in proportion, Put hydrogen into the kettle to replace the air in the kettle, stir, and after raising the temperature to 100-160°C, feed ammonia and hydrogen into the kettle, then react for 2-5 hours, cool down and discharge the material, and remove the catalyst from the material liquid to obtain the product. The invention has the advantages of mild conditions, simple process and high yield.
Description
Technical field
The present invention relates to a kind of method of the 3-of preparation alkoxy propyl amine.
Background technology
Fat primary amine is a class important chemical material, and they can be used for preparing tensio-active agent, sterilant, fuel and lubricant additive, also can be directly used in mineral floating, anticorrosion, road construction and water treatment.Usually aliphatic amide can utilize the animal and plant grease to produce, and also can utilize petroleum component to obtain.
The 3-alkoxy propyl amine is a kind of special aliphatic amide.Its special feature is that except grease and oil, the alcohol of many forms also can be as the synthesis material of 3-alkoxy propyl amine.The derivative of 3-alkoxy propyl amine and amine thereof has comprised the character of different carbon chain lengths and different tensio-active agent.Add typical cats product character, the simple derivative of 3-alkoxy propyl amine and they in oil or organic system, has high workability, low melting point, characteristic easy to use.
In the preparation method of 3-alkoxy propyl amine, at first from pure and mild vinyl cyanide, prepare the alkoxyl group propionitrile, then with product hydrogenation.For example, people's such as Uter Morene method [J.Am.Chem.Soc.Vol.57, the 1505th page (1945)], the method for narration etc. is known method in No. the 869th, 405, English Patent.Yet in these methods, oxidizing reaction is to carry out under the high hydrogen pressure of about 10MPa.Therefore, these methods can not be said so industrial suitable.On the other hand, Japanese Patent Application Publication discloses a kind of method No. 103505/1975, in this method, use a kind of alkalimetal oxide obtaining nitrile, after removing alkali metal hydroxide with the hydrogenation under about 2.5MPa or lower hydrogen pressure of formed nitrile.This method need be removed the complex operations of alkali metal hydroxide, and its productive rate is low.Therefore this method is as also unsatisfactory by the method that the alkoxyl group propionitrile prepares alkoxy propyl amine with technical scale.
Summary of the invention
The purpose of this invention is to provide a reaction conditions gentleness, technology is simple, productive rate the is high method for preparing the 3-alkoxy propyl amine.
For achieving the above object, the present invention realizes by the following technical solutions:
(1) cyanoethylation reaction:
Is 0.2～1.2wt% mixing back stirring of pure consumption with pure and mild aqueous sodium hydroxide solution by sodium hydroxide concentration, is heated to 40-70 ℃, dropwise adds and pure equimolar vinyl cyanide, drips off vinyl cyanide afterreaction 1.5-5h, obtains 3-alkoxyl group propionitrile after waiting to lower the temperature;
(2) hydrogenation reduction:
With 3-alkoxyl group propionitrile, skeleton nickel and H
2O places autoclave in proportion, feeds hydrogen air in the displacement still to the still, stirs, be warming up to 100～160 ℃ after, in still, feed ammonia and hydrogen, react 2～5h then after, cooling discharge, feed liquid is removed catalyzer and is product;
Described skeleton nickel consumption is 0.7～3wt% of 3-alkoxyl group propionitrile consumption, hydrogen pressure 1.0～2.5MPa, NH
3Pressure 0.4～1.4MPa, H
2The O consumption is 0.7～3.0wt% of 3-alkoxyl group propionitrile consumption.
Aforesaid 3-alkoxy propyl amine is R-O-CH
2CH
2CH
2NH
2, wherein R represents to have 8 to 18 straight or branched alkyl that carbon atom is arranged.
Aforesaid pure R-OH, wherein R represents to have 8 to 18 the straight or branched alkyl that carbon atom is arranged, 2-Ethylhexyl Alcohol, isodecyl alcohol, lauryl alcohol, tridecanol, palmityl alcohol, stearyl alcohol, i-octadecanol or 2-octyl dodecanols.In these alcohol, first-selected straight chain alcohol is preferably primary alconol or secondary alcohol.
Aforesaid 3-alkoxyl group propionitrile is R-O-CH
2CH
2CN, wherein R represents to have 8 to 18 straight or branched alkyl that carbon atom is arranged.
Advantage of the present invention is as follows:
1, when carrying out hydrogenating reduction, hydrogen pressure is lower than 2.5MPa, the reaction conditions gentleness.
2, after the preparation of intermediate 3-alkoxyl group propionitrile, the complex operations that does not need to remove alkali metal hydroxide can directly be carried out hydrogenating reduction.
3, transformation efficiency height.
4, technology is simple, and is easy to operate.
Embodiment
Embodiment 1
Different tridecanol 150g (0.75mol) and aqueous sodium hydroxide solution 1.35g are mixed, be heated to 60 ℃, drip vinyl cyanide 50ml (0.75mol) then, after being added dropwise to complete, under 60 ℃, stir, behind the aging 3.5h, stop heating, cooling, discharging, obtain 3-alkoxyl group propionitrile, transformation efficiency is 92.95%.
Again 3-alkoxyl group propionitrile 150g, skeleton nickel 3g and water 4.5g are placed autoclave, feed hydrogen and to still, replace air in the still, stir, feed hydrogen and to still, replace air in the still, stir, reaction system is heated to 140 ℃, with hydrogen 2.0MPa and ammonia 1.0MPa pressurization, under this pressure of maintenance, react, behind the question response 3h, stop heating, with reaction system cooling back discharging, remove skeleton nickel to obtain the 3-alkoxy propyl amine with filtration method, transformation efficiency is 95.57%.
Embodiment 2
With C
8-10Alcohol 150g (0.75mol) and aqueous sodium hydroxide solution 1.8g mix, and are heated to 40 ℃, drip vinyl cyanide 50ml (0.75mol) then, after being added dropwise to complete, stir under 40 ℃, behind the aging 5h, stop heating, cooling, and discharging obtains 3-C
8-10Alkoxyl group propionitrile, transformation efficiency are 95.93%.
Again with 3-C
8-10Alkoxyl group propionitrile 150g, skeleton nickel 4.5g and water 3g place autoclave, feed hydrogen and to still, replace air in the still, stir, reaction system is heated to 160 ℃,, under this pressure of maintenance, reacts with hydrogen 2.5MPa and ammonia 1.4MPa pressurization, behind the question response 5h, stop heating,, remove catalyzer to obtain 3-C with filtration method with reaction system cooling back discharging
8-10Alkoxy propyl amine, transformation efficiency are 96.57%.
Embodiment 3
I-octadecanol 150g (0.75mol) and aqueous sodium hydroxide solution 0.3g are mixed, be heated to 70 ℃, drip vinyl cyanide 50ml (0.75mol) then, after being added dropwise to complete, under 70 ℃, stir, behind the aging 5h, stop heating, cooling, discharging, obtain 3-isooctadecane oxygen base propionitrile, transformation efficiency is 94.33%.
Again 3-isooctadecane oxygen base propionitrile 150g, skeleton nickel 2g and water 1g are placed autoclave, feed hydrogen and to still, replace air in the still, stir, reaction system is heated to 150 ℃, with hydrogen 2.5MPa and ammonia 1.0MPa pressurization, under this pressure of maintenance, react, behind the question response 5h, stop heating, with reaction system cooling back discharging, remove catalyzer to obtain 3-isooctadecane oxygen base propylamine with filtration method, transformation efficiency is 96.57%.
Embodiment 4
Lauryl alcohol 150g (0.75mol) and aqueous sodium hydroxide solution 1.4g are mixed, be heated to 70 ℃, drip vinyl cyanide 50ml (0.75mol) then, after being added dropwise to complete, under 70 ℃, stir, behind the aging 3h, stop heating, cooling, discharging, obtain 3-dodecyloxy propionitrile, transformation efficiency is 91.53%.
Again 3-ten dioxy base propionitrile 150g, skeleton nickel 3g and water 3g are placed autoclave, feed hydrogen and to still, replace air in the still, stir, reaction system is heated to 100 ℃, with hydrogen 1.0MPa and ammonia 1.0MPa pressurization, under this pressure of maintenance, react, behind the question response 5h, stop heating, with reaction system cooling back discharging, remove catalyzer to obtain 3-dodecyloxy propylamine with filtration method, transformation efficiency is 95.67%.
Embodiment 5
Isodecyl alcohol 150g (0.75mol) and aqueous sodium hydroxide solution 0.3g are mixed, be heated to 50 ℃, drip vinyl cyanide 50ml (0.75mol) then, after being added dropwise to complete, under 50 ℃, stir, behind the aging 1.5h, stop heating, cooling, discharging, obtain 3-isodecyl alkoxyl group propionitrile, transformation efficiency is 90.77%.
Again 3-isodecyl oxygen base propionitrile 150g, skeleton nickel 1g and water 3g are placed autoclave, feed hydrogen and to still, replace air in the still, stir, reaction system is heated to 160 ℃, with hydrogen 1.2MPa and ammonia 0.4MPa pressurization, under this pressure of maintenance, react, behind the question response 2h, stop heating, with reaction system cooling back discharging, remove catalyzer to obtain 3-isodecyl alkoxy propyl amine with filtration method, transformation efficiency is 93.85%.
Embodiment 6
Lauryl alcohol 150g (0.75mol) and aqueous sodium hydroxide solution 1.5g are mixed, be heated to 50 ℃, drip vinyl cyanide 50ml (0.75mol) then, after being added dropwise to complete, under 50 ℃, stir, behind the aging 1.5h, stop heating, cooling, discharging, obtain 3-dodecyloxy propionitrile, transformation efficiency is 92.73%.
Again 3-ten dioxy base propionitrile 150g, skeleton nickel 4.5g and water 2g are placed autoclave, feed hydrogen and to still, replace air in the still, stir, reaction system is heated to 120 ℃, with hydrogen 1.5MPa and ammonia 0.8MPa pressurization, under this pressure of maintenance, react, behind the question response 3h, stop heating, with reaction system cooling back discharging, remove catalyzer to obtain 3-dodecyloxy propylamine with filtration method, transformation efficiency is 94.52%.
Claims (6)
1, a kind of method for preparing the 3-alkoxy propyl amine is characterized in that comprising the steps:
(1) cyanoethylation reaction:
Is 0.2～1.2wt% mixing back stirring of pure consumption with pure and mild aqueous sodium hydroxide solution by sodium hydroxide concentration, is heated to 40-70 ℃, dropwise adds and pure equimolar vinyl cyanide, drips off vinyl cyanide afterreaction 1.5-5h, obtains 3-alkoxyl group propionitrile after waiting to lower the temperature;
(2) hydrogenation reduction:
With 3-alkoxyl group propionitrile, skeleton nickel and H
2O places autoclave in proportion, feeds hydrogen air in the displacement still to the still, stirs, be warming up to 100～160 ℃ after, in still, feed ammonia and hydrogen, react 2～5h then after, cooling discharge, feed liquid is removed catalyzer and is product;
Described skeleton nickel consumption is 0.7～3wt% of 3-alkoxyl group propionitrile consumption, hydrogen pressure 1.0～2.5MPa, NH
3Pressure 0.4～1.4MPa, H
2The O consumption is 0.7～3.0wt% of 3-alkoxyl group propionitrile consumption.
2, a kind of method for preparing the 3-alkoxy propyl amine as claimed in claim 1 is characterized in that described alcohol is R-OH, and wherein R represents to have the straight or branched alkyl of 8 to 18 carbon atoms.
3, a kind of method for preparing the 3-alkoxy propyl amine as claimed in claim 2 is characterized in that described R is a straight chained alkyl.
4, a kind of method for preparing the 3-alkoxy propyl amine as claimed in claim 2 is characterized in that described alcohol is 2-Ethylhexyl Alcohol, isodecyl alcohol, lauryl alcohol, tridecanol, palmityl alcohol, stearyl alcohol or i-octadecanol.
5, a kind of method for preparing the 3-alkoxy propyl amine as claimed in claim 2 is characterized in that described alcohol is primary alconol or secondary alcohol.
6, a kind of method for preparing the 3-alkoxy propyl amine as claimed in claim 1 is characterized in that described 3-alkoxyl group propionitrile is R-O-CH
2CH
2CN, wherein R represents to have the straight or branched alkyl of 8 to 18 carbon atoms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200710062128 CN100584820C (en) | 2007-06-06 | 2007-06-06 | A kind of method for preparing 3-alkoxypropylamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200710062128 CN100584820C (en) | 2007-06-06 | 2007-06-06 | A kind of method for preparing 3-alkoxypropylamine |
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| Publication Number | Publication Date |
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| CN101058546A CN101058546A (en) | 2007-10-24 |
| CN100584820C true CN100584820C (en) | 2010-01-27 |
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| CN 200710062128 Expired - Fee Related CN100584820C (en) | 2007-06-06 | 2007-06-06 | A kind of method for preparing 3-alkoxypropylamine |
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX352083B (en) | 2011-04-13 | 2017-11-08 | Basf Se | Amine and diamine compounds and their use for inverse froth flotation of silicate from iron ore. |
| CN103755575A (en) * | 2013-11-21 | 2014-04-30 | 中国林业科学研究院林产化学工业研究所 | Ether amine preparation method |
| CN104829469A (en) * | 2015-04-03 | 2015-08-12 | 广东省石油化工研究院 | Ether amine flotation agent synthesis method |
| CN109456204B (en) * | 2018-10-30 | 2021-10-15 | 昆山市祥和精细化工厂 | Preparation method of gamma-methoxypropylamine |
| CN113004171B (en) * | 2021-03-09 | 2022-09-16 | 万华化学集团股份有限公司 | Preparation method of 3-methoxypropylamine |
| CN115246778B (en) * | 2022-08-15 | 2024-09-17 | 江苏万盛大伟化学有限公司 | Preparation method of fatty alkoxy propylamine |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2280790A (en) * | 1940-12-23 | 1942-04-28 | Resinous Prod & Chemical Co | Unsaturated ether nitriles |
| GB869405A (en) * | 1958-11-21 | 1961-05-31 | Dehydag Gmbh | Process for the preparation of ether-amines |
| US4313004A (en) * | 1981-02-02 | 1982-01-26 | Milliken Research Corporation | Process for the reduction of dicyanoglycols |
| CN85100307A (en) * | 1985-04-01 | 1986-08-06 | 抚顺市化工研究设计院 | Process of producing dipropylamine by hydrogenation of acrylonitrile |
| CN1362402A (en) * | 2000-12-28 | 2002-08-07 | 花王株式会社 | Ether amide production method |
-
2007
- 2007-06-06 CN CN 200710062128 patent/CN100584820C/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2280790A (en) * | 1940-12-23 | 1942-04-28 | Resinous Prod & Chemical Co | Unsaturated ether nitriles |
| GB869405A (en) * | 1958-11-21 | 1961-05-31 | Dehydag Gmbh | Process for the preparation of ether-amines |
| US4313004A (en) * | 1981-02-02 | 1982-01-26 | Milliken Research Corporation | Process for the reduction of dicyanoglycols |
| CN85100307A (en) * | 1985-04-01 | 1986-08-06 | 抚顺市化工研究设计院 | Process of producing dipropylamine by hydrogenation of acrylonitrile |
| CN1362402A (en) * | 2000-12-28 | 2002-08-07 | 花王株式会社 | Ether amide production method |
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| CN101058546A (en) | 2007-10-24 |
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