Method for making an oxirane

• US 6,350,888 B1
• Filed: 05/26/2000
• Issued: 02/26/2002
• Est. Priority Date: 09/18/1997
• Status: Expired due to Term

• Current Assignee: Akzo Nobel Chemicals AG (Nouryon BV)
• Original Assignee: Solvay SA (Solvac SA)
• Inventors: Gilbeau, Patrick, Strebelle, Michel, Balthasart, Dominique
• Primary Examiner(s): SOLOLA, TAOFIQ A
• Application Number:
  US09/508,731
• Time in Patent Office: 641 Days
• Field of Search: 549/529, 549/531
• US Class Current: 549/529
• CPC Class Codes: C07D 301/12 with hydrogen peroxide or inorganic peroxides or peracids
• CPC Class Codes: C07D 301/32 Separation; Purification

Abstract

An epoxide prepared by epoxidation of an olefinic compound by a peroixide compound in liquid medium is separated from the reaction medium by liquid-liquid extraction using an extraction solvent.

Claims

1. A process for making 1,2-epoxy-3-chloropropane by reaction between allyl chloride and an inorganic peroxide compound in a liquid medium containing an alcohol as a diluent, the alcohol being at least partially water-soluble, the process comprising:

collecting a mixture of reaction products comprising 1,2-epoxy-3-chloropropane, the alcohol and water and, optionally, the unconverted reactants;

placing the mixture in contact with an extraction solvent selected from the group consisting of o-xylene, m-xylene, p-xylene, p-dichlorobenzene, o-chlorotoluene, m-chlorotoluene, p-chlorotoluene, n-tridecane, o-dichlorobenzene, m-dichlorobenzene, 1,3,5-trimethylbenzene, decalin, o-chlorotoluene, 1,2,3-trichloropropane, allyl chloride, nitrobenzene and n-decane, and mixtures thereof, so as to obtain two distinct liquid phases, said extraction solvent being suitable for dissolving 1,2-epoxy-3-chloropropane, the alcohol being sparingly soluble in the solvent, the liquid phases comprising an extract containing at least some of the extraction solvent and at least 10% of the amount of 1,2-epoxy-3-chloropropane produced, and a raffinate containing at least some of the alcohol and at least some of the water;

collecting separately the extract and the raffinate;

subjecting the extract to a distillation in order to remove 1,2-epoxy-3-chloropropane therefrom; and

subjecting the raffinate to a distillation in order to remove water therefrom.

2. The process according to claim 1, wherein the density of the extraction solvent differs from that of the mixture of reaction products by at least 0.04 g/cm³.

3. The process according to claim 1 wherein the boiling point of the extraction solvent differs from that of 1,2-epoxy-3-chloropropane by at least 5°

C.

4. The process according to claim 1 wherein the mixture of reaction products is placed in counter-current contact with the extraction solvent in a liquid-liquid extraction column, at a temperature of from 0 to 80°

C.

5. The process according to claim 1, wherein the weight ratio between the extraction solvent and the mixture of reaction products is at least equal to 0.1 and does not exceed 20.

6. The process according to claim 1, wherein the alcohol and the unconverted reactants, collected during the distillation, are returned to the step for making 1,2-epoxy-3-chloropropane.

7. The process according to claim 1 wherein the peroxide compound comprises hydrogen peroxide.