CN100386306C - 3-(2-methoxyethoxy)-propylamine production process - Google Patents
3-(2-methoxyethoxy)-propylamine production process Download PDFInfo
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- CN100386306C CN100386306C CNB2005100414578A CN200510041457A CN100386306C CN 100386306 C CN100386306 C CN 100386306C CN B2005100414578 A CNB2005100414578 A CN B2005100414578A CN 200510041457 A CN200510041457 A CN 200510041457A CN 100386306 C CN100386306 C CN 100386306C
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- methoxy ethoxy
- propylamine
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Abstract
The present invention relates to a method for the chemical synthesis of 3-(2-methoxyethoxy) propylamine. 3-(2-methoxyethoxy)-propylamine with the advantages of good product purity and high yield can be obtained through condensation reaction, distillation and hydrogenation reaction. The present invention has the advantages of mild technological line and operational condition and basic no other loss except for little damage to a distillation still. Meanwhile, no pollution is generated in the whole process, and the present invention has marked social benefit and economic benefit and can be widely used for practical production.
Description
Technical field
The present invention relates to the method for chemosynthesis 3-(2-methoxy ethoxy)-propylamine.
Background technology
3-(2-methoxy ethoxy)-propylamine is a kind of purposes primary amine compounds comparatively widely.It both can be used as the important intermediate of dispersion dyestuffs such as the synthetic bright blue S-GL of dispersion, progressively applies at petroleum chemical industry as a kind of novel corrosion inhibitor and ionization emulsifying agent of external introduction again, but the present domestic manufacturer production of still not having.Therefore, 3-(2-methoxy ethoxy)-propylamine synthetic has very important and practical meanings.Through consulting amount of literature data, determine that its synthetic method is: ethylene glycol monomethyl ether and vinyl cyanide make 3-(2-methoxy ethoxy)-propionitrile through addition condensation reaction under catalyst action, and then hydrogenation makes the itrile group reduction obtain 3-(2-methoxy ethoxy)-propylamine under pressure.Its reaction equation is:
CH
3OCH
2CH
2OH+CH
2＝CH
2CN—→CH
3OCH
2CH
2OCH
2CH
2CN—→CH
3OCH
2CH
2OCH
2CH
2CH
2NH
2
Though more than provide a kind of mentality of designing for synthetic 3-(2-methoxy ethoxy)-propylamine, but be applied to actual production, also have a large amount of work, also need a large amount of creativeness inventions, just can be applied to suitability for industrialized production as parameters such as each technological process, proportionings.
Summary of the invention
The object of the invention be to invent a kind of technology simple, be easy to control, 3-(2-methoxy ethoxy)-propylamine production technique that yield is higher.
The present invention includes following steps:
1) condensation reaction: add sodium methylate and Resorcinol in ethylene glycol monomethyl ether, through stirring, drip vinyl cyanide again, ethylene glycol monomethyl ether and vinyl cyanide feed intake (mol ratio) than being 1: 1～1.1, keep temperature of reaction at 25 ℃～30 ℃ therebetween; Dropwise follow-up continuation of insurance temperature reaction 60 minutes ± 10 minutes;
2) distillation: in above-mentioned reactant, add dense H
2SO
4Be neutralized to pH=7, obtain pale brown look liquid; Pale brown look liquid is carried out air distillation, slowly be warming up to 80 ℃ and steam low boiler cut; Air distillation is carried out underpressure distillation after finishing again, obtains the preceding intermediate product 3-(2-methoxy ethoxy) of hydrogenation-propionitrile colourless liquid; Be used for the follow-up hydrogenation reaction through gas chromatographic detection content (answering 〉=98%).NaSO
4Stay in the still kettle raffinate.
3) hydrogenation reaction: ammonia is fed distillation obtain in 3-(2-methoxy ethoxy)-propionitrile colourless liquid, under the effect of Raney's nickel-cobalt-chromium composite catalyst, temperature of reaction is 90 ℃～100 ℃, under 3～4MPa pressure, carry out the liquid phase catalytic hydrogenation reaction, reaction times is 4 hours ± 0.5 hour, the weight ratio 3-that respectively feeds intake (2-methoxy ethoxy)-propionitrile: catalyzer: ammonia=4000～4500: 20～30: 8500～9000.
In order to improve the purity of product, can be with the further rectification and purification of step 3) gained crude product.
The method of rectification and purification is: still kettle is loaded onto rectifying column, and normal pressure steams a small amount of low boiler cut, and broad in the middle section cut is refined product, and still is residual to be the not 3-of hydrogenation (2-methoxy ethoxy)-high boiling fractions such as propionitrile of minute quantity.
Operational path operational condition gentleness of the present invention, good product purity, and also yield is higher, except that a small amount of distillation still residue, does not have other losses substantially.Whole flow process does not produce any pollution simultaneously, and social benefit and remarkable in economical benefits can be widely used in actual production.
Specific embodiment
1, main raw material:
Industrial ethylene glycol monomethyl ether (concentration 〉=95%); Industrial vinyl cyanide (purity 〉=98%); Sodium methylate, Resorcinol, dense H
2SO
4, hydrogen, ammonia
2, condensation reaction:
In container, add 410kg ethylene glycol monomethyl ether, 5kg sodium methylate, 0.33kg Resorcinol, through fully stirring, slowly dripped the 284kg vinyl cyanide in 3 hours, ethylene glycol monomethyl ether and vinyl cyanide feed ratio are 1mol: 1.05mol, keep temperature of reaction at 25 ℃～30 ℃ therebetween.Dropwise follow-up continuation of insurance temperature reaction 1 hour, and survey terminal point with gas chromatograph, the terminal point controlling index is acrylonitrile content≤1%.As less than terminal point, then continue insulation.
3, distillation:
As vinyl cyanide oneself basically after the complete reaction, add the dense H of about 2kg
2SO
4In and feed liquid, adjust pH and reach 7.The reaction product that obtain this moment is pale brown look, still is liquid, water soluble.Owing to can separate out solid NaSO during this product low temperature
4So, before hydrogenation reaction, must be removed by distillation procedure.
At first carry out air distillation, slowly be warming up to 80 ℃ and steam low boiler cut.Air distillation is carried out underpressure distillation after finishing again, thereby obtains the preceding intermediate product 3-(2-methoxy ethoxy) of hydrogenation-propionitrile, is colourless liquid, is used for the follow-up hydrogenation reaction through gas chromatographic detection content (answering 〉=98%).NaSO
4Stay in the still kettle raffinate.
4, hydrogenation reaction:
Hydrogenation reaction equipment is the stainless steel pressure still, and catalyzer is Raney's nickel-cobalt-chromium composite catalyst, and temperature of reaction is 90～100 ℃, carries out liquid phase catalytic hydrogenation (feeding ammonia in the reaction process) under 3～4MPa hydrogen pressure in alcohol solvent.
Concrete feed ratio is: intermediate product 3-(2-the methoxy ethoxy)-about 440kg of propionitrile, catalyzer 2.5kg, ammonia 880kg.About 4 hours of reaction times.Obtain crude product.
After reaction finished, ammonia was derived by the another one tower, can recycle when secondary response down.
5, purify:
Still kettle is loaded onto rectifying column, and normal pressure steams a small amount of low boiler cut, and broad in the middle section cut is refined product, and still is residual to be the not 3-of hydrogenation (2-methoxy ethoxy)-high boiling fractions such as propionitrile of minute quantity.
Crude product obtains content greater than the finished product 3-(2-methoxy ethoxy)-propylamine of 99.5% through rectification and purification, and total recovery is 91%.
Claims (3)
1.3-(2-methoxy ethoxy)-propylamine production technique is characterized in that may further comprise the steps:
1) condensation reaction: add sodium methylate and Resorcinol in ethylene glycol monomethyl ether, through stirring, drip vinyl cyanide again, the mol ratio that ethylene glycol monomethyl ether and vinyl cyanide feed intake is 1: 1～1.1, keeps temperature of reaction at 25 ℃～30 ℃ therebetween; Dropwise follow-up continuation of insurance temperature reaction 60 minutes ± 10 minutes;
2) distillation: in above-mentioned reactant feed liquid, add dense H
2SO
4Be neutralized to pH=7, obtain pale brown look liquid; Pale brown look liquid is carried out air distillation, slowly be warming up to 80 ℃, steam low boiler cut; Air distillation is carried out underpressure distillation after finishing again, obtains the preceding intermediate product 3-(2-methoxy ethoxy) of hydrogenation-propionitrile colourless liquid;
3) hydrogenation reaction: ammonia is fed in 3-(2-methoxy ethoxy)-propionitrile colourless liquid, under the effect of Raney's nickel-cobalt-chromium composite catalyst, temperature of reaction is 90 ℃～100 ℃, under 3～4MPa pressure, carry out the liquid phase catalytic hydrogenation reaction, reaction times is 4 hours native 0.5 hour, the weight ratio 3-that respectively feeds intake (2-methoxy ethoxy)-propionitrile: catalyzer: ammonia=4000～4500: 20～30: 8500～9000.
2. according to the described 3-of claim 1 (2-methoxy ethoxy)-propylamine production technique, it is characterized in that step 3) gained crude product rectification and purification.
3. according to the described 3-of claim 2 (2-methoxy ethoxy)-propylamine production technique, it is characterized in that the method for rectification and purification is: still kettle is loaded onto rectifying column, and normal pressure steams a small amount of low boiler cut, and broad in the middle section cut is refined product.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100414578A CN100386306C (en) | 2005-08-08 | 2005-08-08 | 3-(2-methoxyethoxy)-propylamine production process |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100414578A CN100386306C (en) | 2005-08-08 | 2005-08-08 | 3-(2-methoxyethoxy)-propylamine production process |
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| Publication Number | Publication Date |
|---|---|
| CN1733702A CN1733702A (en) | 2006-02-15 |
| CN100386306C true CN100386306C (en) | 2008-05-07 |
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| CNB2005100414578A Expired - Fee Related CN100386306C (en) | 2005-08-08 | 2005-08-08 | 3-(2-methoxyethoxy)-propylamine production process |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108129352A (en) * | 2017-12-27 | 2018-06-08 | 惠州市宙邦化工有限公司 | A kind of preparation method of 3- allyloxys propionitrile |
| CN115246778A (en) * | 2022-08-15 | 2022-10-28 | 江苏万盛大伟化学有限公司 | Preparation method of fatty alkoxy propylamine |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RO69385A2 (en) * | 1976-04-28 | 1980-10-30 | Institutul De Cercetari,Inginerie Tehnologica Si Proiectare Pentru Rafinarii,Ro | PROCESS FOR THE PREPARATION OF PRIMARY ALCOHAMINS |
| JPH04117348A (en) * | 1990-09-06 | 1992-04-17 | New Japan Chem Co Ltd | Production of aliphatic primary amine |
-
2005
- 2005-08-08 CN CNB2005100414578A patent/CN100386306C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RO69385A2 (en) * | 1976-04-28 | 1980-10-30 | Institutul De Cercetari,Inginerie Tehnologica Si Proiectare Pentru Rafinarii,Ro | PROCESS FOR THE PREPARATION OF PRIMARY ALCOHAMINS |
| JPH04117348A (en) * | 1990-09-06 | 1992-04-17 | New Japan Chem Co Ltd | Production of aliphatic primary amine |
Non-Patent Citations (2)
| Title |
|---|
| 3－（2－甲氧基乙氧基）－丙胺合成工艺. 张存.精细化工中间体，第31卷第6期. 2001 |
| 3－（2－甲氧基乙氧基）－丙胺合成工艺. 张存.精细化工中间体，第31卷第6期. 2001 * |
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| CN1733702A (en) | 2006-02-15 |
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Assignee: Yangzhou Liushi Chemicals Co., Ltd. Assignor: Yangzhou University Contract record no.: 2010320000925 Denomination of invention: Process for producing 3- (2- methoxy - ethoxy) - amphetamine Granted publication date: 20080507 License type: Exclusive License Open date: 20060215 Record date: 20100714 |
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