CN101462978B - N-methylol acrylamide and preparation thereof - Google Patents
N-methylol acrylamide and preparation thereof Download PDFInfo
- Publication number
- CN101462978B CN101462978B CN2007101510730A CN200710151073A CN101462978B CN 101462978 B CN101462978 B CN 101462978B CN 2007101510730 A CN2007101510730 A CN 2007101510730A CN 200710151073 A CN200710151073 A CN 200710151073A CN 101462978 B CN101462978 B CN 101462978B
- Authority
- CN
- China
- Prior art keywords
- preparation
- phenothiazine
- stopper
- reaction
- 500ppm
- 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 - Fee Related
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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
Acrylic amide 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.There is following deficiency in the preparation method of existing N hydroxymethyl acrylamide: 1. the solvent that uses all belongs to hazardous substance; 2. pollute greatly, environmental-protecting performance is poor; 3. strong toxicity; 4. cost is high.
Summary of the invention
The objective of the invention is to overcome the weak point of prior art, 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 moity and weight percent are respectively:
Acrylic amide 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 PARA HYDROXY BENZALDEHYDE, 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 acrylic amide, Paraformaldehyde 96, water are fully mixed the formation mixing solutions in reaction kettle, the addition of stopper is 0～500ppm in the reaction system, opens steam valve then, the control rate of heating;
(2). in vp is that 0.5～1Mpa, temperature add catalyzer at 35～45 ℃;
(3). when temperature rises to 55～65 ℃, kept 1～2 hour, 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, and quality product is high, the no waste discharging, and more environmental protection is used more convenient.
2. the present invention has optimized and has produced required reaction environment, and sub product 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 specified; 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 moity and weight (kg) are:
Acrylic amide 60
Paraformaldehyde 96 20
Water 15
Sodium methylate 2.
A kind of preparing method's of N hydroxymethyl acrylamide step is:
(1). by proportioning acrylic amide, Paraformaldehyde 96, water, MEHQ, sodium methylate are fully mixed the formation mixing solutions in reaction kettle, the addition of stopper MEHQ is 100～500ppm; Open steam valve then, the control rate of heating;
(2). in vp is that 0.5～1Mpa, temperature add the catalyzer sodium methylate at 40 ℃;
(3). when temperature rises to 60 ℃, kept 1.5 hours, reaction finishes, and crystallisation by cooling produces crystallisate;
(4). crystallisate dewaters through water extracter, is drying to obtain finished product.
Embodiment 2:
Acrylic amide 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:
Acrylic amide 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 (1)
1. the preparation method of a N hydroxymethyl acrylamide, it is characterized in that: the step of its preparation method is:
(1). by proportioning acrylic amide, Paraformaldehyde 96, water are fully mixed the formation mixing solutions in reaction kettle, the addition of stopper is 0～500ppm in the reaction system, opens steam valve then, the control rate of heating;
(2). in vp is that 0.5～1Mpa, temperature add catalyzer at 35～45 ℃;
(3). when temperature rises to 55～65 ℃, kept 1～2 hour, reaction finishes, and crystallisation by cooling produces crystallisate;
(4). crystallisate dewaters through water extracter, is drying to obtain the N hydroxymethyl acrylamide finished product;
Wherein, the moity of reaction system and weight percent are respectively:
The addition of stopper is 0～500ppm in the reaction system;
Described catalyzer is the wherein a kind of or mixture of sodium methylate and yellow soda ash;
Described stopper is the wherein a kind of or mixture of PARA HYDROXY BENZALDEHYDE and phenothiazine;
The addition of MEHQ, phenothiazine is respectively in the described stopper:
MEHQ: 100～500ppm
Phenothiazine: 50～300ppm.
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 CN101462978A (en) | 2009-06-24 |
| CN101462978B true CN101462978B (en) | 2012-06-27 |
Family
ID=40803799
Family Applications (1)
| 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 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101462978B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112939799B (en) * | 2020-12-24 | 2023-06-27 | 湖北鑫甬生物环保科技有限公司 | Synthesis method of N-methylol acrylamide |
| CN112679376B (en) * | 2020-12-24 | 2023-06-30 | 湖北鑫甬生物环保科技有限公司 | Synthesis method of N, N' -methylene bisacrylamide |
Citations (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 |
| US4567297A (en) * | 1984-04-17 | 1986-01-28 | Wacker-Chemie Gmbh | Preparation of aqueous N-methylol amide 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 |
| CN1135748A (en) * | 1994-09-16 | 1996-11-13 | 日东化学工业株式会社 | N-methylolacrylamide crystal process for producing the same and method of storing the same |
-
2007
- 2007-12-17 CN CN2007101510730A patent/CN101462978B/en not_active Expired - Fee Related
Patent Citations (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 |
| US4567297A (en) * | 1984-04-17 | 1986-01-28 | Wacker-Chemie Gmbh | Preparation of aqueous N-methylol amide 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 |
| CN1135748A (en) * | 1994-09-16 | 1996-11-13 | 日东化学工业株式会社 | N-methylolacrylamide crystal process for producing the same and method of storing the same |
Non-Patent Citations (3)
| Title |
|---|
| 吴才玉等.N-羟甲基丙烯酰胺的合成.《N-羟甲基丙烯酰胺的合成》.1998,(第6期),第8-10页. * |
| 安原初等.N-羟甲基丙烯酰胺水剂合成工艺及其应用.《河南化工》.2000,(第9期),第9-10页. * |
| 张玉华等.N-羟甲基丙烯酰胺.《陕西化工》.1989,(第3期),第33-34页. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101462978A (en) | 2009-06-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Vigier et al. | Combination of Pd/C and Amberlyst-15 in a single reactor for the acid/hydrogenating catalytic conversion of carbohydrates to 5-hydroxy-2, 5-hexanedione | |
| JP7027547B2 (en) | Methods and Applications for Producing Highly Active Lignin and By-Product Furfural | |
| CN102631930A (en) | Catalyst for preparing furfuryl alcohol from furfural by vapor phase hydrogenation and preparation method thereof | |
| CN109369550B (en) | Preparation method of triazine ultraviolet absorbent | |
| CN106631720B (en) | Method for directly synthesizing polymethoxy dimethyl ether by taking dilute formaldehyde and methylal as raw materials | |
| CN101462978B (en) | N-methylol acrylamide and preparation thereof | |
| CN101157708A (en) | Block polyether compound modified lignin and preparation method and uses thereof | |
| CN104387234A (en) | Method for synthesizing 3-methyl-3-butene-1-ol | |
| CN103289073A (en) | Preparation method of polycarboxylate water-reducing agent macromonomer methylallyl alcohol polyethenoxy ether | |
| CN108355706A (en) | Multistage porous molecular sieve, preparation method and its application in synthesizing diamino diphenylmethane derivatives | |
| CN103756001B (en) | The production method of the inorganic graft modification phenolic resin foam of high flame retardant high tenacity | |
| CN103145937B (en) | Method for preparing hydroxyl-blocked polysiloxane-toughened modified phenolic resin | |
| CN104016905A (en) | Method for preparing 2-vinylpyridine | |
| CN103012079A (en) | Method for synthesizing ethylene glycol allyl ether under catalysis of solid base catalyst | |
| CN103951699B (en) | A kind of method of low pressure Fast back-projection algorithm diethyl hypophosphite and products thereof and application | |
| CN102320978A (en) | Preparation method of anhydrous system o-nitroanisole | |
| CN109225349B (en) | Preparation method of catalyst for preparing isobutene by cracking methyl tert-butyl ether | |
| CN107881201A (en) | A kind of method of m-hydroxybenzoic acid synthesis resorcinol | |
| CN110229126B (en) | Based on high temperature high pressure CO2Method for decomposing fructose by system catalysis | |
| CN107382659A (en) | A kind of preparation method of 2,3,3,3 tetrafluoropropene | |
| CN103936568B (en) | A kind of method being prepared by methoxy toluene to p-methoxybenzyl alcohol | |
| CN109384654B (en) | Method for producing ethylene glycol mono-tert-butyl ether | |
| CN109232196B (en) | Preparation method of methyl tert-butyl ether | |
| CN102093510A (en) | Method for synthesizing m-pentadiene petroleum resin by thermal polymerization | |
| CN111944083A (en) | Preparation method of modified macroporous acidic cation exchange resin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C56 | Change in the name or address of the patentee | ||
| CP01 | Change in the name or title of a patent holder |
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 |
|
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20120627 Termination date: 20161217 |