# US 9,518,035 B2 · Method for preparing glycidol using glycerol and glycidol obtained thereby

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- Number: US 9,518,035 B2
- Document ID: US9518035B2
- Status: Granted
- Kind: B2
- Application number: 15/015,890
- Filed: 2016-02-04
- Published: 2016-08-25
- Granted: 2016-12-13
- Earliest claimed: 2015-02-23
- Assignees: Korea Institute of Science and Technology
- Applicants: Korea Institute of Science and Technology
- Inventors: Hyun Joo Lee; Byoung Sung Ahn; Sang Deuk Lee; Ji Sik Choi; Hyejeong Lee; Hye Jin Lee
- Web page: https://patentgrep.com/patent/US9518035B2

## CPC

- C07D 301/02: Synthesis of the oxirane ring
- C07D 317/20: Free hydroxyl or mercaptan
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A method for preparing glycidol using glycerol includes mixing glycerol with urea in the presence of at least one zinc-based catalyst selected from the group consisting of Zn(NO3)2, ZnCl2, ZnO and Zn(OAc)2 under a pressure of 0.5-10 kPa at a temperature of 100-170° C. to obtain glycerol carbonate; filtering the glycerol carbonate mixed with the zinc-based catalyst through an adsorbent including a polymer resin coordinated with amine groups to separate the zinc-based catalyst and glycerol carbonate from each other; and carrying out reaction of the glycerol carbonate separated from the zinc-based catalyst in the presence of an anion alkali metal salt catalyst that is Na, K, Rb, Cs or a mixture thereof containing at least one anion selected from the group consisting of Cl−, Br−, I−, NO3−, NO2− and acetate under a pressure of 0.13-6.67 kPa at a temperature of 140-250° C. to obtain glycidol.

## Claims

### Claim 1

A method for preparing glycidol, comprising the steps of:
(A) mixing glycerol with urea in the presence of a zinc-based catalyst to obtain glycerol carbonate;
(B) filtering the glycerol carbonate mixed with the zinc-based catalyst through an adsorbent including a polymer resin coordinated with amine groups to separate the zinc-based catalyst and glycerol carbonate from each other; and
(C) carrying out reaction of the glycerol carbonate separated from the zinc-based catalyst in the presence of an anion alkali metal salt catalyst to obtain glycidol.

### Claim 2 (depends on 1)

The method for preparing glycidol according to claim 1, wherein the amine group in step (B) is selected from the group consisting of ethylenediamine, diethylenetriamine and triethylenetetramine.

### Claim 3 (depends on 1)

The method for preparing glycidol according to claim 1, wherein the polymer resin in step (B) is Merrifield resin or Wang resin.

### Claim 4 (depends on 1)

The method for preparing glycidol according to claim 1, wherein the adsorbent in step (B) comprises amine groups present in the polymer resin at a concentration of 1.5-4 mmol/g.

### Claim 5 (depends on 1)

The method for preparing glycidol according to claim 1, wherein the zinc-based catalyst in step (A) is at least one selected from the group consisting of Zn(NO3)2, ZnCl2, ZnO and Zn(OAc)2.

### Claim 6 (depends on 1)

The method for preparing glycidol according to claim 1, wherein urea is mixed with glycerol at a ratio of 1-5 moles per mole of glycerol, in step (A).

### Claim 7 (depends on 1)

The method for preparing glycidol according to claim 1, wherein the zinc-based catalyst is mixed in an amount of 0.1-5 mole % based on glycerol, in step (A).

### Claim 8 (depends on 1)

The method for preparing glycidol according to claim 1, wherein the anion alkali metal salt catalyst in step (C) is Na, K, Rb, Cs or a mixture thereof containing at least one anion selected from the group consisting of Cl−, Br−, I−, NO3−, NO2− and acetate.

### Claim 9 (depends on 1)

The method for preparing glycidol according to claim 1, wherein the anion alkali metal salt catalyst is used in an amount of 0.1-5 mole % based on glycerol carbonate, in step (C).

### Claim 10 (depends on 1)

The method for preparing glycidol according to claim 1, wherein step (C) is carried out in a continuous reaction mode in which glycidol is recovered continuously under reduced pressure.