Method for producing glycidol

• US 8,969,600 B2
• Filed: 02/05/2013
• Issued: 03/03/2015
• Est. Priority Date: 11/14/2012
• Status: Expired due to Fees

• Current Assignee: Korea Advanced Institute of Science and Technology
• Original Assignee: Korea Advanced Institute of Science and Technology
• Inventors: Lee, Hyun Joo, Lee, Sang Deuk, Ahn, Byoung Sung, Kim, Chang Soo, Choi, Ji Sik
• Primary Examiner(s): Jarrell, Noble
• Assistant Examiner(s): MAURO, JOHN MATTHEW
• Application Number:
  US13/759,692
• Publication Number:
  US 20140135512A1
• Time in Patent Office: 756 Days
• Field of Search: 549/518
• US Class Current: 549/518
• CPC Class Codes: C07D 301/02 Synthesis of the oxirane ring

Abstract

Disclosed is a method for producing glycidol by decarboxylation of glycerol carbonate. In the method, an ionic liquid catalyst is added for the reaction. According to the method glycidol can be produced in high yield and selectivity. The method enables the production of glycidol in an easy, simple and environmentally friendly way.

Claims

1. A method for producing glycidol by decarboxylation of glycerol carbonate, wherein an ionic liquid catalyst is added for the reaction, wherein the ionic liquid catalyst comprises:

2. The method according to claim 1, wherein the ionic liquid catalyst comprises at least one anion selected from the group consisting of PF₆⁻

, BF₄⁻

, F₃CSO₃⁻

, NO₃⁻

, I⁻

, Br⁻

, Cl⁻

, CH₃CO₂⁻

, and HCO₃⁻

.

3. The method according to claim 1, wherein the ionic liquid catalyst is used in an amount of 0.0025 moles or less per one mole of the glycerol carbonate.

4. The method according to claim 1, wherein a Lewis acid metal salt, together with the ionic liquid catalyst, is further added.

5. The method according to claim 4, wherein the Lewis acid metal salt is selected from the group consisting of Zn(NO₃)₂, ZnCl₂, SnCl₄, MgCl₂, AlCl₃, and mixtures thereof.

6. The method according to claim 4, wherein the Lewis acid metal salt is added in an amount of 0.2 moles or less per one mole of the ionic liquid catalyst.

7. The method according to claim 1, wherein a solvent is further added in which the solvent is selected from the group consisting of polyethylene glycol dimethyl ether (DMPEG), dibenzyl ether, and dibutylphthalate.

8. The method according to claim 1, wherein the decarboxylation and glycidol collection are carried out simultaneously in a continuous process.

9. A method for producing glycidol comprising:

putting together glycerol carbonate, 1-butyl-3-methylimidazolium nitrate, Zn(NO₃)₂, and a solvent to form a mixture, wherein the solvent is selected from the group consisting of polyethylene glycol dimethyl ether (DMPEG), dibenzyl ether, and dibutylphthalate;

heating the mixture to not higher than 175°

C. at ambient pressure; and

depressurizing the heated mixture to produce glycidol.