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Methyl acrylate preparation method

A technology of acrylate and manufacturing method, applied in the field of acrylate manufacturing, can solve problems such as insufficient storage stability and thermal stability of acrylate

Active Publication Date: 2011-09-28
TOAGOSEI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] However, although the method described in Patent Document 2 can effectively shorten the separation time of the organic layer and the water layer, the storage stability and thermal stability of the obtained (meth)acrylate are insufficient.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103] (Example 1) (manufacture of 4 functional group acrylate)

[0104] In a 2L four-necked flask with a side tube provided with a reflux tube, 500 g of an 8-mol adduct of ethylene oxide (hereinafter referred to as (DGEO)) of diglycerol, 306 g of acrylic acid, 550 g of toluene, 13 g of sulfuric acid, and p-benzene Diphenol monomethyl ether (hereinafter referred to as (MQ)) 1.4g, copper chloride 1.4g, blow into oxygen-containing gas (oxygen 5 volume %, nitrogen 95 volume %, the same below), and adjust the reaction temperature to be 80~110 ℃ at the same time , The reaction system pressure is 400 ~ 760mmHg, while heating and stirring. The generated water was discharged out of the system with a Dean-Stark tube, and a dehydration-esterification reaction was performed for 7 hours.

[0105] After the reaction was completed, the reaction solution was cooled to below 40° C., and toluene and pure water were added for extraction and washing. Then, 400 g of a 20% by mass sodium hydroxi...

Embodiment 2

[0110] (Example 2) (manufacture of 4 functional group acrylate)

[0111] In Example 1, change to DGEO800g, acrylic acid 829g, toluene 883g, sulfuric acid 34g, MQ is 2.5g, cupric chloride 2.5g, carry out 10 hours reaction under reaction system pressure 600~760mmHg, besides, use The same method as in Example 1 was carried out for dehydration esterification.

[0112] After completion of the reaction, neutralization and washing were performed in the same manner as in Example 1 except that 700 g of 20% NaOH water was used.

[0113] To the obtained organic layer, 2.25 g of tetrabutylammonium bromide (hereinafter referred to as (TBPB)) (0.09 mol% relative to the number of hydroxy groups of DGEO), 2,6-di-tert-butyl-4 - 0.56 g of methylphenol (hereinafter referred to as (BHT)), 135 g of 20% NaOH water (7.6 mol% relative to the number of moles of hydroxyl groups in DGEO), and stirred at 65° C. for 3 hours.

[0114] After standing still, the lower layer was discharged, 810 g of pure wa...

Embodiment 3

[0117] (Example 3) (manufacture of 4 functional group acrylate)

[0118] Esterification was carried out under the same raw materials and conditions as in Example 2.

[0119] After the reaction, the same method as in Example 2 was used for neutralization and washing.

[0120] To the obtained organic layer, 2.48 g of an aqueous 80% tetrabutylphosphonium chloride solution (hereinafter referred to as (TBPC1)) (0.09 mol% relative to the hydroxyl group of DGEO), 0.56 g of BHT, and 135 g of 20% NaOH water were added. (7.6 mol% with respect to the number of moles of the hydroxyl group of DGEO) It stirred at 65 degreeC for 3 hours.

[0121] After standing still, the lower layer was discharged, 810 g of pure water was added to carry out extraction and washing, 1.99 g of MQ was added, and toluene was distilled off under reduced pressure while blowing an oxygen-containing gas. Acrylate was obtained after filtering the obtained crude reaction product under pressure.

[0122] About the o...

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Abstract

A process for producing a (methyl)acrylic ester, characterized by carrying out a dehydration esterification reaction of (meth)acrylic acid and an alcohol in the presence of an acid catalyst; adding to the reaction solution an aqueous solution of alkali metal hydroxide and any of compounds of the following general formula (1) and heating the mixture at 45 DEG to 100 DEG C. (1) (in the general formula (1), A is a nitrogen atom or phosphorus atom; each of R<1> to R<4> independently is a C=5 alkyl, phenyl or benzyl; and X<-> is an inorganic anion or organic acid ion.) By this process, there can be obtained a (methyl)acrylic ester improved in storage stability and thermal stability.

Description

technical field [0001] The invention relates to a method for producing (meth)acrylate, which belongs to the technical field of methods for producing (meth)acrylate. Background technique [0002] Since (meth)acrylate is cured by ultraviolet irradiation or electron beam irradiation, it is generally used as a mixing component of a photocurable composition for various industrial applications such as optical lenses, printing inks, coating agents, and adhesives. [0003] However, when the storage stability and thermal stability of (meth)acrylate are poor, trouble may arise. [0004] For example, when the storage stability of the (meth)acrylate is poor, a polymerization reaction may occur during storage to generate a polymer component, or the (meth)acrylate may be decomposed to generate an acid component such as (meth)acrylic acid. [0005] A (meth)acrylate composition containing a polymer component is not suitable for use in optical lens applications where uniformity and transluc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/08C07C67/60C07C69/54C07B61/00
CPCC07C67/08C07C67/60
Inventor 桥本直树佐内康之
Owner TOAGOSEI CO LTD
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