CN101462978A - N-methylol acrylamide and preparation thereof - Google Patents
N-methylol acrylamide and preparation thereof Download PDFInfo
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- CN101462978A CN101462978A CN 200710151073 CN200710151073A CN101462978A CN 101462978 A CN101462978 A CN 101462978A CN 200710151073 CN200710151073 CN 200710151073 CN 200710151073 A CN200710151073 A CN 200710151073A CN 101462978 A CN101462978 A CN 101462978A
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- acrylamide
- stopper
- hydroxymethyl acrylamide
- preparation
- phenothiazine
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Abstract
The invention relates to a N-methylolacrylamide and a preparation method thereof, belonging to the fine chemistry industry field. Acrylamide and paraformaldehyde are used as raw materials, and the N-methylolacrylamide is prepared by reaction in the presence of a catalyst and solvent; wherein, one or several of parahydroxyben-zaldehyde, hydroquinone and phenothiazine are added in a reaction system. The invention optimizes the reaction environment required by the production, has fewer byproducts and improves the product quality and the yield correspondingly, and the invention has simple technology and convenient use and is safe and environment-friendly.
Description
Technical field
The invention belongs to field of fine chemical, particularly relate to a kind of N hydroxymethyl acrylamide and preparation method thereof.
Background technology
Acrylamide series is used widely as a kind of cross-linking monomer, and N hydroxymethyl acrylamide is used more extensive as the principal item of this cross-linking monomer.The preparation method of existing N hydroxymethyl acrylamide has the following disadvantages: 1. the solvent of Shi Yonging all belongs to hazardous substance; 2. pollute greatly, environmental-protecting performance is poor; 3. strong toxicity; 4. cost height.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art part, a kind of high-quality, low-cost, high yield, low emission, pollution-free and N hydroxymethyl acrylamide that technology is simple, easy to use and preparation method thereof are provided.
The present invention realizes that the technical scheme of purpose is:
A kind of N hydroxymethyl acrylamide, its moiety and weight percent are respectively:
Acrylamide 40～70
Paraformaldehyde 96 10～30
Water 15～30
Catalyzer 1～10
The addition of stopper is 0～500ppm in the reaction system.
And described catalyzer is wherein one or more mixtures of sodium methylate, sodium hydroxide and yellow soda ash.
And described stopper is the wherein a kind of of p-Hydroxybenzaldehyde, Resorcinol and phenothiazine, or two or more mixture.
And the addition of Resorcinol, MEHQ, phenothiazine is respectively in the described stopper:
Resorcinol: 0～200ppm
MEHQ: 100～500ppm
Phenothiazine: 50～300ppm.
A kind of preparation method of N hydroxymethyl acrylamide, the step of its preparation method is:
(1). by proportioning acrylamide, Paraformaldehyde 96, water are fully mixed the formation mixing solutions in reactor, the addition of stopper is 0～500ppm in the reaction system, opens steam valve then, the control rate of heating;
(2). in vapour pressure is that 0.5～1Mpa, temperature add catalyzer at 35～45 ℃;
(3). kept 1～2 hour when temperature rises to 55～65 ℃, reaction finishes, and crystallisation by cooling produces crystallisate;
(4). crystallisate dewaters through water extracter, is drying to obtain the N hydroxymethyl acrylamide finished product.
Advantage of the present invention and positively effect are:
1. the present invention adopts water to make solvent, and does not use the organic solvent of hazard class, realize pollution-free, good environmental protection; Toxicity is little, and is harmless; Cost is low, the quality product height, and the no waste discharging, more environmental protection is used more convenient.
2. the present invention has optimized and has produced required reaction environment, and byproduct reduces, and quality product is improved, the corresponding raising of yield, and technology is simple, and easy to use, safety and environmental protection.
Embodiment
Below in conjunction with embodiment, the present invention is further described; Following embodiment is illustrative, is not determinate, can not limit protection scope of the present invention with following embodiment.
Need to prove:
The addition of Resorcinol, MEHQ, phenothiazine is respectively in the stopper:
Resorcinol: 0～200ppm
MEHQ: 100～500ppm
Phenothiazine: 50～300ppm.
Embodiment 1:
A kind of N hydroxymethyl acrylamide, its moiety and weight (kg) are:
Acrylamide 60
Paraformaldehyde 96 20
Water 15
Sodium methylate 2.
A kind of preparation method's of N hydroxymethyl acrylamide step is:
(1). by proportioning acrylamide, Paraformaldehyde 96, water, MEHQ, sodium methylate are fully mixed the formation mixing solutions in reactor, the addition of stopper MEHQ is 100～500ppm; Open steam valve then, the control rate of heating;
(2). in vapour pressure is that 0.5～1Mpa, temperature add the catalyzer sodium methylate at 40 ℃;
(3). kept 1.5 hours when temperature rises to 60 ℃, reaction finishes, and crystallisation by cooling produces crystallisate;
(4). crystallisate dewaters through water extracter, is drying to obtain finished product.
Embodiment 2:
Acrylamide 50
Paraformaldehyde 96 15
Water 25
Yellow soda ash 5.
Stopper adopts phenothiazine in the reaction system, and addition is 50～300ppm.
The step of its preparation method is same as embodiment 1.
Embodiment 3:
Acrylamide 45
Paraformaldehyde 96 25
Water 20
Sodium hydroxide 6.
Stopper is selected Resorcinol for use in the reaction system, and addition is 0～200ppm.
The step of its preparation method is same as embodiment 1.
Claims (5)
1. N hydroxymethyl acrylamide, it is characterized in that: its moiety and weight percent are respectively:
Acrylamide 40～70
Paraformaldehyde 96 10～30
Water 15～30
Catalyzer 1～10
The addition of stopper is 0～500ppm in the reaction system.
2. described a kind of N hydroxymethyl acrylamide according to claim 1 is characterized in that: described catalyzer is the wherein a kind of of sodium methylate, sodium hydroxide and yellow soda ash, or two or more mixture.
3. described a kind of N-hydroxyl bisacrylamide according to claim 1, it is characterized in that: described stopper is the wherein a kind of of p-Hydroxybenzaldehyde, Resorcinol and phenothiazine, or two or more mixture.
4. described a kind of N hydroxymethyl acrylamide according to claim 3, it is characterized in that: the addition of Resorcinol, MEHQ, phenothiazine is respectively in the described stopper:
Resorcinol: 0～200ppm
MEHQ: 100～500ppm
Phenothiazine: 50～300ppm.
5. the preparation method of an a kind of N hydroxymethyl acrylamide as claimed in claim 1, it is characterized in that: the step of its preparation method is:
(1). by proportioning acrylamide, Paraformaldehyde 96, water are fully mixed the formation mixing solutions in reactor, the addition of stopper is 0～500ppm in the reaction system, opens steam valve then, the control rate of heating;
(2). in vapour pressure is that 0.5～1Mpa, temperature add catalyzer at 35～45 ℃;
(3). kept 1～2 hour when temperature rises to 55～65 ℃, reaction finishes, and crystallisation by cooling produces crystallisate;
(4). crystallisate dewaters through water extracter, is drying to obtain the N hydroxymethyl acrylamide finished product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007101510730A CN101462978B (en) | 2007-12-17 | 2007-12-17 | N-methylol acrylamide and preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007101510730A CN101462978B (en) | 2007-12-17 | 2007-12-17 | N-methylol acrylamide and preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101462978A true CN101462978A (en) | 2009-06-24 |
| CN101462978B CN101462978B (en) | 2012-06-27 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2007101510730A Expired - Fee Related CN101462978B (en) | 2007-12-17 | 2007-12-17 | N-methylol acrylamide and preparation thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112679376A (en) * | 2020-12-24 | 2021-04-20 | 湖北鑫甬生物环保科技有限公司 | Synthesis method of N, N' -methylene bisacrylamide |
| CN112939799A (en) * | 2020-12-24 | 2021-06-11 | 湖北鑫甬生物环保科技有限公司 | Synthesis method of N-hydroxymethyl acrylamide |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3887618A (en) * | 1974-02-28 | 1975-06-03 | American Cyanamid Co | Use of weak base resins as catalysts for the methylolation of acrylamide |
| DE3414525A1 (en) * | 1984-04-17 | 1985-10-24 | Wacker-Chemie GmbH, 8000 München | METHOD FOR PRODUCING AQUEOUS N-METHYLOL (METH) ACRYLAMIDE SOLUTIONS |
| CN85105587A (en) * | 1985-07-17 | 1987-01-14 | 江苏省海水综合利用研究所 | The preparation method of N hydroxymethyl acrylamide |
| KR100368784B1 (en) * | 1994-09-16 | 2003-04-11 | 미쯔비시 레이온 가부시끼가이샤 | N-methylol acrylamide crystals, preparation method thereof and storage method thereof |
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2007
- 2007-12-17 CN CN2007101510730A patent/CN101462978B/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112679376A (en) * | 2020-12-24 | 2021-04-20 | 湖北鑫甬生物环保科技有限公司 | Synthesis method of N, N' -methylene bisacrylamide |
| CN112939799A (en) * | 2020-12-24 | 2021-06-11 | 湖北鑫甬生物环保科技有限公司 | Synthesis method of N-hydroxymethyl acrylamide |
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| CN101462978B (en) | 2012-06-27 |
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Address after: 300240 Tianjin Admiralty street Dongli District Xu Zhuangzi Patentee after: TIANJIN CHEMICAL REAGENT RESEARCH INSTITUTE CO., LTD. Address before: 300240 Tianjin Admiralty street Dongli District Xu Zhuangzi Patentee before: Tianjin chemical research institute |
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Granted publication date: 20120627 Termination date: 20161217 |
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