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Method of producing glycidyl 2-hydroxyisobutyrate

一种缩水甘油酯、羟基异丁酸的技术，应用在环氧树脂用反应性稀释剂,环氧树脂组合物领域，达到提高反应收率、容易且稳定制备、降低副产物的量的效果

Inactive Publication Date: 2005-06-22
MITSUBISHI GAS CHEM CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, since the hydroxyl and carboxyl groups easily react with epichlorohydrin, there has been no method so far that can easily and stably prepare a compound having a hydroxyl group and a glycidyl group in the same molecule with high purity.

Method used

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  • Method of producing glycidyl 2-hydroxyisobutyrate
  • Method of producing glycidyl 2-hydroxyisobutyrate
  • Method of producing glycidyl 2-hydroxyisobutyrate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～5 and comparative example 1

[0043] At room temperature and normal pressure, add 37.83g (0.3 mole) sodium 2-hydroxyisobutyrate, 138.7g (1.5 mole) epichlorohydrin, 0.25g tetramethyl chloride Ammonium and purified water were heated from room temperature to an internal temperature of 120° C. within 10 minutes, kept at this temperature for 1.5 hours to react, and then cooled to room temperature. After adding water therein and leaving it to stand for 1.5 hours, the organic solvent phase was taken out, epichlorohydrin was distilled off in a distillation apparatus equipped with a Vigreul distillation tube, and the resulting residue was distilled under reduced pressure to obtain 2-hydroxyisobutyric acid glycidyl esters. The mol ratio of feeding intake, reaction conditions and reaction yield, the amount of by-products after vacuum distillation are as shown in Table 1 and 2. In addition, the addition rate of the catalyst and water in a table|surface is the quantity calculated with respect to the total weight of ep...

Embodiment 1     Embodiment 2     Embodiment 3

[0046] Feeding molar ratio (formula (1) raw material compound / EpCH) 0.2 0.2 0.2

[0047] Reaction temperature (℃) 120 120 120

[0048] Reaction time (hours) 1.5 1.5 1.5

[0049] Catalyst Type TMAC TMAC TMAC

[0050] Amount added (g) 0.25 0.25 0.25

[0051] Addition rate (weight%) 0.14 0.14 0.14

[0052] Amount of water added (g) 0.55 1.00 2.00

[0053] Addition rate (weight%) 0.31 0.56 1.11

[0054] Reaction yield (%) 69 66 65

[0055] By-product amount (weight%) 2.1 0.70 0.30

[0056] Table 2

Embodiment 4

[0057] Example 4 Example 5 Comparative Example 1

[0058] Feeding molar ratio (formula (1) raw material compound / EpCH) 0.2 0.2 0.2

[0059] Reaction temperature (℃) 120 120 120

[0060] Reaction time (hours) 1.5 1.5 1.5

[0061] Catalyst Type TMAC TMAC TMAC

[0062] Amount added (g) 0.25 0.25 0.25

[0063] Addition rate (weight%) 0.14 0.14 0.14

[0064] Amount of water added (g) 0.20 5.00 0

[0065] Addition rate (weight%) 0.11 2.75 0

[0066] Reaction yield (%) 62 47 62

[0067] By-product amount (weight %) 4.9 0.85 6.4

[0068] As shown in Table 1 and Table 2, under the conditions of the present invention (Examples 1-5), the reaction yield was high, and at least the amount of by-products after vacuum distillation was suppressed. It can be seen that these effects are remarkable when the addition amount of water is adjusted within a specific range (Examples 1 to 3). On the other ha...

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Abstract

The present invention provides a method for stably preparing high-purity glycidyl 2-hydroxyisobutyrate with high yield. Moreover, this invention provides the reactive diluent for epoxy resins which used the said glycidyl 2-hydroxyisobutyrate, and an epoxy resin composition.

Description

technical field [0001] The invention relates to a preparation method of glycidyl 2-hydroxyisobutyrate represented by formula (2). More specifically, it relates to a method for producing high-purity glycidyl 2-hydroxyisobutyrate by reacting a raw material compound in the presence of water, and a product containing glycidyl 2-hydroxyisobutyrate obtained by the above method. Reactive diluent for epoxy resin, and epoxy resin composition. [0002] Background technique [0003] Using catalysts such as quaternary ammonium salts, the method for preparing glycidyl esters from carboxylic acids, or alkali metal salts thereof, and epichlorohydrin is known (for example, refer to Japanese Patent Application Laid-Open No. 9-59268, Japanese Patent Laid-Open No. 2003-171371 ). In addition, a method for producing glycidyl ether from alcohol and epichlorohydrin using a catalyst such as a quaternary ammonium salt is also known (see, for example, JP-A-5-32650 and JP-A-5-163260). [0004] H...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/10C07C29/32C07D303/16
CPCC07D303/16C07C29/10C07C29/32
Inventor 志田隆敏铃木周
Owner MITSUBISHI GAS CHEM CO INC
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