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Method for continuously producing (methyl) hydroxyethyl acrylate and (methyl) diester acrylate and sulfoacid 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: 2018-01-19
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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  • Method for continuously producing (methyl) hydroxyethyl acrylate and (methyl) diester acrylate and sulfoacid resin catalyst

Examples

Experimental program
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Effect test

preparation example 1

[0091] (a) Combine styrene, vinyltris-(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, and then add sulfuric acid. The molar ratio of polymer microspheres to sulfuric acid is 1:2, and the reaction is sulfonated at 50°C for 8 hours, filtered and washed with water. Obtain 1# sulfonic acid resin catalyst.

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

preparation example 2

[0095] (a) Combine styrene, vinyl tris(2,2,2-trifluoro)ethoxysilane, isobornyl (meth)acrylate, 1,4-propylene glycol diacrylate, n-eicosane and peroxide Benzoyl, the molar ratio is 0.7:2.5:1:0.35:0.9:0.016 for feeding, using suspension polymerization, reacting at 95℃ for 3h to prepare low surface energy polymer microspheres;

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

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

preparation example 3

[0099] (a) Styrene, 1,4-propanediol diacrylate, n-eicosane and benzoyl peroxide were charged with a molar ratio of 0.7:0.35:0.9:0.016, and the suspension polymerization was used at 95℃. React for 3 hours to prepare low surface energy polymer microspheres;

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

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

[0102] From 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 ...

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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 methods for synthesizing compounds, and specifically relates to a method for continuously producing hydroxy (meth)acrylate and diester (meth)acrylate and a method for preparing a sulfonic acid resin catalyst. Background technique [0002] Hydroxy (meth)acrylate is an important acrylate monomer. Hydroxyethyl (meth)acrylate and hydroxypropyl (meth)acrylate can be combined with (meth)acrylic acid and ethylene oxide and propylene oxide. It is prepared by ring opening, 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 preparing 4-hydroxybutyl acrylate by dehydration and esterification reaction of 1,4-butanediol and acrylic acid. This solution uses sulfuric acid and p-toluenesulfonic acid as catalysts to cause side reactions. The amount of production of substances is large, and sin...

Claims

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Application Information

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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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