Continuous production method of hydroxy (meth)acrylate and diester of (meth)acrylate and sulfonic acid resin catalyst

A technology of sulfonic acid resin and acrylate, which is applied in chemical instruments and methods, preparation of ester groups and hydroxyl groups, catalysts for physical/chemical processes, etc. It can solve the problems of affecting downstream use and high product color number

Active Publication Date: 2020-06-02
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Patent document CN103755565 A discloses a preparation method of neopentyl glycol dimethacrylate. In order to prevent product polymerization, a high concentration of nitroxide radicals are used to inhibit polymerization. Since the polymerization inhibitor is difficult to separate from the product, resulting in product High color number affects downstream use

Method used

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  • Continuous production method of hydroxy (meth)acrylate and diester of (meth)acrylate and sulfonic acid resin catalyst

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0091] (a) Styrene, vinyl tris-(trifluoro)methoxysilane, cyclohexyl (meth)acrylate, 1,6-hexanediol diacrylate, n-undecane and azobisisobutyl Nitrile, the molar ratio is 0.5: 1.5: 1: 0.2: 0.6: 0.014 for feeding, using suspension polymerization, reacting at 70°C for 5 hours to prepare low surface energy polymer microspheres;

[0092] (b) Swell the prepared polymer microspheres in methanol for 4 hours, then add sulfuric acid, the molar ratio of polymer microspheres to sulfuric acid is 1:2, sulfonate at 50°C for 8 hours, filter and wash with water Obtain 1# sulfonic acid resin catalyst.

[0093] Utilize GB-T1720-79 (89) paint film adhesion test method and sessile drop contact angle test method to detect the obtained sulfonic acid resin catalyst, the adhesion reaches 2 grades, and the contact angle reaches 103°.

preparation example 2

[0095] (a) Styrene, vinyltris(2,2,2-trifluoro)ethoxysilane, isobornyl (meth)acrylate, 1,4-propanediol diacrylate, n-eicosane and peroxide Benzoyl is fed at a molar ratio of 0.7:2.5:1:0.35:0.9:0.016, and reacted at 95°C for 3 hours by suspension polymerization to prepare low surface energy polymer microspheres;

[0096] (b) Swell the prepared polymer microspheres in n-hexane for 4 hours, then add sulfur trioxide, the molar ratio of polymer microspheres to sulfur trioxide is 1:3, sulfonate at 80°C for 6 hours, filter After washing with water, 2# sulfonic acid resin catalyst can be obtained.

[0097] Utilize GB-T1720-79 (89) paint film adhesion test method and sessile drop contact angle test method to detect the obtained sulfonic acid resin catalyst, the adhesion reaches 2 grades, and the contact angle reaches 110°.

preparation example 3

[0099] (a) Feed styrene, 1,4-propanediol diacrylate, n-eicosane and benzoyl peroxide at a molar ratio of 0.7:0.35:0.9:0.016, and use suspension polymerization at 95°C React for 3 hours to prepare low surface energy polymer microspheres;

[0100] (b) Swell the prepared polymer microspheres in n-hexane for 4 hours, then add sulfur trioxide, the molar ratio of polymer microspheres to sulfur trioxide is 1:3, sulfonate at 80°C for 6 hours, filter After washing with water, 3# sulfonic acid resin catalyst can be obtained.

[0101] Utilize the GB-T1720-79 (89) paint film adhesion test method and sessile drop contact angle test method to detect the obtained sulfonic acid resin catalyst, the adhesion reaches 4 grades, and the contact angle reaches 82°.

[0102]Through the performance test results of the sulfonic acid resin catalysts obtained in the above three preparation examples, it can be seen that the sulfonic acid resin catalysts obtained in Preparation Examples 1 and 2 containing...

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Abstract

The invention belongs to the technical field of a synthesis compound, and provides a sulfoacid resin catalyst and a method for continuously producing (methyl) hydroxyethyl acrylate and (methyl) diester acrylate. The continuous production method comprises the following steps of (1) contacting dihydric alcohol, (methyl) methyl acrylate and polymerization inhibitors to form reaction liquid; continuously injecting the materials into a reaction device containing the sulfoacid resin catalyst for reaction so as to obtain coarse reaction liquid; (2) injecting the coarse reaction liquid obtained in thestep (1) into a phase splitting tank; performing double-solvent extraction; respectively obtaining a water phase containing (methyl) hydroxyethyl acrylate and an oil phase containing (methyl) diesteracrylate; (3) respectively performing rectification on the water phase and the oil phase in the step (2) to obtain (methyl) hydroxyethyl acrylate and (methyl) diester acrylate products. The method has the advantages that the product separation step is simplified; the separation temperature is low and the product purity is high.

Description

technical field [0001] The invention belongs to the technical field of synthetic compound methods, in particular to a method for continuously producing hydroxy (meth)acrylate and diester (meth)acrylate and a preparation method for a sulfonic acid resin catalyst. Background technique [0002] Hydroxy (meth)acrylate is an important acrylate monomer. Hydroxyethyl (meth)acrylate and hydroxypropyl (meth)acrylate can pass through (meth)acrylic acid and ethylene oxide and propylene oxide. Ring-opening preparation, but hydroxy (meth)acrylates containing higher carbon atoms are often prepared by transesterification and esterification. [0003] German patent document No. 1518572 discloses a method for the dehydration and esterification of 1,4-butanediol and acrylic acid to prepare 4-hydroxybutyl acrylate, which uses sulfuric acid and p-toluenesulfonic acid as catalysts to cause side reactions to form A large amount of substances are generated, and since an acid is used as a catalyst,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/10B01J35/08C07C69/54C07C67/03C07C67/58C07C67/54C08F230/08C08F212/08C08F220/18C08F222/14
Inventor 郭华郑京涛黎源鞠昌迅陆国太
Owner WANHUA CHEM GRP CO LTD
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