IP Library Granted Patent US 9,303,003
Granted Patent B2
US 9,303,003 · App. 14/434,211 · Granted Apr 5, 2016

Process for producing glycidyl (meth)acrylate

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Quick Facts
Patent No.
US 9,303,003
App. No.
14/434,211
Granted
Apr 5, 2016
Kind
B2
Abstract

Provided is glycidyl(meth)acrylate which is reduced in the content of impurities including chlorine. This process comprises reacting epichlorohydrin with an alkali metal (meth)acrylate in the presence of a catalyst to produce glycidyl(meth)acrylate, the process including a step in which the reaction is conducted while making a Bronsted acid present in the reaction system in an amount of 0.0001-0.08 mol per mol of the alkali metal (meth)acrylate.

Claims (16)

1. A process, comprising:

reacting epichlorohydrin with an alkali metal salt of (meth)acrylic acid in the presence of a catalyst, thereby producing glycidyl (meth)acrylate,

wherein reacting the epichlorohydrin with the alkali metal salt of (meth)acrylic acid is in the presence of a Broensted acid in a reaction system in an amount of 0.0001 mol to 0.08 mol per mol of the alkali metal salt of (meth)acrylic acid,

wherein a total content of chloropropenyl (meth)acrylate and 1,3-dichloro-2-propanol in a reaction solution is 2770 ppm or less,

wherein the catalyst is a quaternary ammonium salt and/or an ion exchange resin comprising a quaternary ammonium salt.

2. The process of claim 1 , wherein a content of chloropropenyl (meth)acrylate in the reaction solution is 850 ppm or less.

3. The process of claim 1 , wherein a content of 1,3-dichloro-2-propanol in the reaction solution is 2560 ppm or less.

4. The process of claim 2 , wherein a content of 1,3-dichloro-2-propanol in the reaction solution is 2560 ppm or less.

5. The process of claim 1 , wherein the catalyst is a quaternary ammonium salt.

6. The process of claim 1 , wherein the catalyst is an ion exchange resin comprising a quaternary ammonium salt.

7. The process of claim 1 , wherein the Broensted acid is (meth)acrylic acid, benzoic acid, acetic acid, methane sulfonic acid, or any combination thereof.

8. The process of claim 1 , wherein a total chlorine content is 486 ppm or less.

9. The process of claim 1 , further comprising neutralizing (meth)acrylic acid with an alkali metal hydroxide, thereby obtaining the alkali metal salt of (meth)acrylic acid, prior to the reacting of epichlorohydrin with the alkali metal salt of (meth)acrylic acid,

wherein a molar mixing ratio of the (meth)acrylic acid to the alkali metal hydroxide is from 0.9 to 1.1.

10. The process of claim 1 , wherein the process does not comprise distillation.

11. The process of claim 1 , wherein the process further comprises washing then distilling the glycidyl (meth)acrylate.

Assignments (2)
CHANGE OF NAME Recorded Sep 5, 2017
From: MITSUBISHI RAYON CO., LTD.
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 043750/0834 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 8, 2015
From: MURATA, NAOSHI; MORI, HIROYUKI
To: MITSUBISHI RAYON CO., LTD.
Reel/Frame 035359/0157 →