Method for producing an epoxide, in particular of glycidol, and installation for implementation

• US 6,316,641 B1
• Filed: 09/08/1999
• Issued: 11/13/2001
• Est. Priority Date: 03/12/1997
• Status: Expired due to Fees

• Current Assignee: Organisation Nationale Interprofessionelle Des Oleagineux
• Original Assignee: Organisation Nationale Interprofessionelle Des Oleagineux
• Inventors: Yoo, Jeong-Woo, Gaset, Antoine, Mouloungui, Zéphirin
• Primary Examiner(s): Solola, Taofiq A.
• Application Number:
  US09/380,710
• Time in Patent Office: 797 Days
• Field of Search: 549/519, 549/541
• US Class Current: 549/519
• CPC Class Codes: C07D 301/02 Synthesis of the oxirane ring

Abstract

The invention concerns a method for preparing an epoxide, in particular glycidol, wherein a cyclic organic carbonate, in particular glycerol carbonate, is heated under reduced pressure so as to carry out a reaction to contract the carbonate ring into an epoxide ring. According to the present invention, the reaction is carried out in a solid/liquid system in the presence of a polyol and a solid catalyst consisting of a type A zeolite or γ-alumina. The method, which may be carried out continuously, enables the epoxide to be formed in a single step, the epoxide being exhausted in the form of vapor which only has to be extracted and separated from the carbon dioxide formed.

Claims

1. A process for preparing an epoxide of the formula:

wherein R is hydrogen, hydroxy, alkyl, alkoxy or acyloxy, comprising the steps of;

heating a cyclic organic carbonate of the formula;

wherein R is as defined above, under reduced pressure to a temperature of at least about 165°

C. so as to effect transformation of the carbonate ring into an epoxy ring,

wherein said transformation is carried out in a solid/liquid medium in the presence of a polyol and a solid catalyst comprising a type A zeolite or γ

-alumina.

2. The process as claimed in claim 1, wherein glycerol or a polyglycerol is used as the polyol.

3. The process as claimed in claim 1, wherein a zeolite in the H form or containing an alkali metal or alkaline earth cation is used as the solid catalyst.

4. The process as claimed in claim 3, wherein said zeolite is mixed into said medium in the form of powder with a mean particle size of between 3 and 5 microns.

5. The process as claimed in claim 3, wherein between 3.5 and 10.5 g of zeolite per mole of cyclic organic carbonate is used.

6. The process as claimed in claim 1, wherein between 0.1 and 0.4 mole of polyol per mole of cyclic organic carbonate is used.

7. The process as claimed in claim 1, wherein the epoxide prepared is glycidol or a glycidyl compound,

wherein glycerol carbonate or a glycidyl compound is used as the cyclic organic carbonate and glycerol is used as the polyol.

8. The process as claimed in claim 7, wherein the medium is heated to a temperature between 170°

C. and 210°

C. and the pressure is adjusted to a value between 3×

30³ and 10×

10³ Pascals.

9. The process as claimed in claim 8, wherein the pressure is adjusted to a value between 3.3×

10³ and 6×

10³ Pascals.

10. The process as claimed in claim 7, further comprising the steps of:

extracting vapors formed of glycidol or glycidyl compound and carbon dioxide from the medium, and

separating the glycidol or glycidyl compound by condensation.

11. The process as claimed in claim 10, further comprising the steps of:

adding glycerol carbonate to the medium to maintain an initial glycerol carbonate concentration, and

adding polyol to keep the proportion of polyol between 0.1 and 0.4 mole of polyol per mole of glycerol carbonate.

12. The process as claimed in claim 10, further comprising the steps of:

delivering a mixture of glycerol carbonate, glycerol and solid catalyst in powder form into a thin-film reactor adapted to centrifuge the mixture and to form a revolving peripheral film;

extracting the medium, vapors of glycidol or a glycidyl compound and a resultant carbon dioxide formed from an upper part of the reactor; and

extracting the other constituents of the medium from a lower part of the reactor.