CN1544416A - Acidamide derivative preparation method - Google Patents
Acidamide derivative preparation method Download PDFInfo
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- CN1544416A CN1544416A CNA2003101054941A CN200310105494A CN1544416A CN 1544416 A CN1544416 A CN 1544416A CN A2003101054941 A CNA2003101054941 A CN A2003101054941A CN 200310105494 A CN200310105494 A CN 200310105494A CN 1544416 A CN1544416 A CN 1544416A
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- fatty group
- bromobenzaldehyde
- acetaldehyde
- exchange resin
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Abstract
A process for preparing amide derivant, comprises reacting fatty group amide with aldehydes in methyl alcohol or carbon tetrachloride or benzene or methylbenzene or dioxane or acetonitrile with the presence of catalyst, and separating the reaction product, characterized in that the catalyst is type H strong acidic positive ion exchange resin, the aldehyde is selected from the groups of paraformaldehyde, acetaldehyde, propionaldehyde, chloral, bromal, glyoxylic acid, 4-bromobenzaldehyde, 3-bromobenzaldehyde, hydrosulfide acetaldehyde, p-nitrobenzaldehyde, and 4-hydroxybenzaldehyde. The formula of the fatty group amide is described in the specification, wherein R 2 is saturated or unsaturated fatty group having 2-12 carbon atoms, the type H strong acidic positive ion exchange resin is sulphonated coal, sulfonated phenylethene copolymer or sulfonated phenol formaldehyde resin.
Description
Technical field
The present invention relates to a kind of amide derivatives, particularly relate to a kind of preparation method of amide derivatives.
Background technology
Chloride N-hydroxyalkyl amide derivative has widely to be used, as being used as thiofide, its polymkeric substance is usually used in fireproofing agent and marine antifouling coating or the like, during preparation, usually with strong acid or highly basic as catalyst for reaction, make the reaction of acid amides and aldehydes generate corresponding N-hydroxyalkyl amide analog derivative.No. 835579 patent reports of Britain in benzene solvent, make catalyzer with highly basic such as Trimethylamine 99, by the reaction of unsaturated amides and chloral, prepare the corresponding amide derivative---N-(1-hydroxyl-2,2,2-three chloroethyls) unsaturated fatty acids base acid amides.At a paper (Farafontova V.I., Podgornova, Deng at Zh.Prikl.Khim (Leningrad), 1975,48 (1) 240-3 (RUSS)) report in: the reaction of (methyl) acrylamide and Paraformaldehyde 96 or chloral can obtain higher yields corresponding N-methylol (methyl) acrylamide under sodium methylate catalysis.No. 135234 patent reports of Poland in methanol solvate, be catalyzer with the p-methyl benzenesulfonic acid, react by unsaturated amides and chloral, prepare the corresponding amide derivative---N-(1-hydroxyl-2,2,2-three chloroethyls) unsaturated fatty acids base acid amides.These preparation methods' common drawback is that catalyzer strong acid or alkaline corrodibility are extremely strong, and easily produces spent acid or salkali waste, and unreacting material also is difficult to separate and reuse.
Summary of the invention
The preparation method who the purpose of this invention is to provide a kind of amide derivatives, it uses H type storng-acid cation exchange resin to be catalyzer, can overcome existing preparation method's above-mentioned shortcoming.
A kind of preparation method of amide derivatives, be included in methyl alcohol or tetracol phenixin or benzene or toluene or dioxane or the acetonitrile under the effect of catalyzer, make fatty group acid amides and aldehyde reaction, and isolate reaction product, it is characterized in that described catalyzer is a H type storng-acid cation exchange resin.
Advantage of the present invention is to have avoided strong acid or alkaline corrosion, and safety is convenient to operation, and catalyzer and unreacted raw material are leached promptly and can reuse.
Embodiment
The preparation of embodiment 1.N-(1-hydroxyl-2,2,2-three chloroethyls) acrylamide
Experimental procedure: (I) in the 1000ml there-necked flask; the acrylamide, the 0.5 gram stopper thiodiphenylamine that add 71.1 grams (1mol); 15g Amberlyst35 (storng-acid cation exchange resin of the H type that Shanghai ROHM AND HAAS chemical industry company limited produces) and 150 ml methanol; logical nitrogen; after several minutes reaction flask is inserted in the 80-90 ℃ of oil bath; under agitation slowly splash into 100 ml methanol solution of 181.5 gram Chloral Hydrates then; added in about 2～3 hours, and under nitrogen protection, continued heated and stirred reaction 1～2 hour.
(II) reaction mixture is filtered, and with methanol wash H type Zeo-karb for several times, merge washings and mother liquor.
(III) with gained liquid 50 ℃ of following evaporated under reduced pressure, promptly get thick product after the drying.
(IV) thick product can be got the white plates crystal with re-crystallizing in ethyl acetate.Filter, after the amount of ethyl acetate washing, oven dry can get highly finished product 164g, and productive rate is 75%.
The preparation of embodiment 2.N-(1-hydroxyl-2,2,2-three chloroethyls) Methacrylamide
Experimental procedure: (I) in the 1000ml there-necked flask; add 85.1 gram (1mol) Methacrylamides, 0.5 gram thiodiphenylamine; 15g Amberlyst and 150 ml methanol; behind the logical nitrogen number minute reaction flask is inserted in the 80-90 ℃ of oil bath; under agitation slowly splash into 100 ml methanol solution of 181.5 gram Chloral Hydrates then; added in about 2～3 hours, and under nitrogen protection, continued heated and stirred reaction 1～2 hour.
(II) reaction mixture is filtered, and with methanol wash H type Zeo-karb for several times, merge washings and mother liquor.
(III) with gained liquid 50 ℃ of following evaporated under reduced pressure, promptly get thick product after the drying.
(IV) thick product can be got white solid with re-crystallizing in ethyl acetate.Thick product can be got the white plates crystal with re-crystallizing in ethyl acetate.Filter, after the amount of ethyl acetate washing, oven dry can get highly finished product 163g, and productive rate is 70%.
The structural formula of the unsaturated fatty acids base acid amides that the present invention is used is:
Wherein R is the saturated or undersaturated fatty group that contains 2～12 carbon atoms, as CH
2-CH, CH
2-CCH
3, CH
3(CH
2)
8, (CH
3)
2CHCH-CH (CH
2)
4Used aldehyde is Paraformaldehyde 96, acetaldehyde, propionic aldehyde, chloral, Chloral Hydrate, bromal, oxoethanoic acid, p-bromobenzaldehyde, 3-bromobenzaldehyde, mercapto-acetaldehyde, paranitrobenzaldehyde or p-Hydroxybenzaldehyde.Catalyzer used in the preparation feedback is the storng-acid cation exchange resin of H type, comprises sulphonated coal, sulfonated phenylethylene copolymer or sulfonated phenol formaldehyde resin.The amide derivatives of the present invention's preparation can be used for production or the film-formable polymer monomer and the fireproofing agent of the stain control agent of antifouling paint, thiofide etc.
Claims (5)
1, a kind of preparation method of amide derivatives, be included in methyl alcohol or tetracol phenixin or benzene or toluene or dioxane or the acetonitrile under the effect of catalyzer, make the reaction of fatty group acid amides and aldehydes, and isolate reaction product, it is characterized in that described catalyzer is a H type storng-acid cation exchange resin.
2, preparation method as claimed in claim 1 is characterized in that described aldehyde is Paraformaldehyde 96, acetaldehyde, propionic aldehyde, chloral, Chloral Hydrate, bromal, oxoethanoic acid, p-bromobenzaldehyde, 3-bromobenzaldehyde, mercapto-acetaldehyde, paranitrobenzaldehyde or p-Hydroxybenzaldehyde.
3, preparation method as claimed in claim 1 is characterized in that the structural formula of described fatty group acid amides is:
Wherein R is the saturated or undersaturated fatty group that contains 2～12 carbon atoms.
4, preparation method as claimed in claim 1 is characterized in that described H type storng-acid cation exchange resin is sulphonated coal, sulfonated phenylethylene copolymer or sulfonated phenol formaldehyde resin.
5, preparation method as claimed in claim 1 is characterized in that feeding nitrogen in described preparation feedback, and adds stopper.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200310105494 CN1218931C (en) | 2003-11-10 | 2003-11-10 | Acidamide derivative preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200310105494 CN1218931C (en) | 2003-11-10 | 2003-11-10 | Acidamide derivative preparation method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1544416A true CN1544416A (en) | 2004-11-10 |
| CN1218931C CN1218931C (en) | 2005-09-14 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200310105494 Expired - Fee Related CN1218931C (en) | 2003-11-10 | 2003-11-10 | Acidamide derivative preparation method |
Country Status (1)
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102424645A (en) * | 2011-07-29 | 2012-04-25 | 湖南大学 | Method for synthesizing aromatic amide and aromatic methanol |
-
2003
- 2003-11-10 CN CN 200310105494 patent/CN1218931C/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102424645A (en) * | 2011-07-29 | 2012-04-25 | 湖南大学 | Method for synthesizing aromatic amide and aromatic methanol |
| CN102424645B (en) * | 2011-07-29 | 2013-09-11 | 湖南大学 | Method for synthesizing aromatic amide and aromatic methanol |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1218931C (en) | 2005-09-14 |
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