Preparation of alkylene carbonates

• US 4,786,741 A
• Filed: 11/15/1982
• Issued: 11/22/1988
• Est. Priority Date: 11/15/1982
• Status: Expired due to Fees

• Current Assignee: Scientific Design Company, Inc. (Clariant AG)
• Original Assignee: Scientific Design Company, Inc. (Clariant AG)
• Inventors: Sachs, Howard M.
• Primary Examiner(s): Hollrah, Glennon H.
• Assistant Examiner(s): RUSSELL, MARK
• Application Number:
  US06/441,191
• Time in Patent Office: 2,199 Days
• Field of Search: 549/230
• US Class Current: 549/230
• CPC Class Codes: C07D 319/06 not condensed with other rings
• CPC Class Codes: C07D 321/00 Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00

Abstract

Alkylene carbonates, particularly ethylene carbonate, are prepared by the reaction of an alkylene oxide with carbon dioxide in the presence of a catalyst at temperatures ranging upwards from 20° C., particularly temperatures above about 90° C., preferably 90°-170° C. The conversion of alkylene oxide to alkylene carbonate can be carried out in the presence of water while minimizing the undesirable hydrolysis of the carbonate to the corresponding alkylene glycol and formation of higher glycols. This is achieved by maintaining the water to alkylene oxide molar ratio and the carbon dioxide to alkylene oxide ratio within the stated limits and adjusting the carbon dioxide partial pressure to provide the desired selectivity to alkylene carbonate.

Claims

1. In a process for preparing alkylene carbonate by the reaction of the corresponding alkylene oxide with carbon dioxide in the presence of an effective amount of at least one catalyst selected from the group consisting of organic quaternary ammonium halides, organic quaternary phosphonium halides, organic sulfonium halides, and organic antimony halides and water, the improvement comprising controlling the selectivity of alkylene carbonate and suppressing formation of higher molecular weight glycols to produce high yields of alkylene carbonate by carrying out said reaction at temperatures above about 90°

C. with a molar ratio of carbon dioxide to alkylene oxide of at least about 1/1, a water to alkylene oxide molar ratio greater than about 0.01/1, and a carbon dioxide partial pressure sufficient to provide the selectivity to alkylene carbonate desired.

2. The process of claim 1 wherein said reaction temperature is between about 90°

C. and about 170°

C.

3. The process of claim 1 wherein said molar ratio of water to alkylene oxide is between about 0.01/1 and about 4/1.

4. The process of claim 3 wherein said molar ratio of water to alkylene oxide is between about 0.1/1 and about 2/1.

5. The process of claim 1 wherein said catalyst is an organic quaternary phosphonium halide.

6. The process of claim 5 wherein said catalyst is methyl triphenyl phosphonium iodide.

7. The process of claim 1 wherein said catalyst is up to about 0.10 mols per mol of alkylene oxide.

8. The process of claim 1 wherein said alkylene carbonate is ethylene carbonate.

9. A process for preparing alkylene carbonate from the reaction of the corresponding alkylene oxide with carbon dioxide in the presence of water comprising contacting said carbon dioxide with said alkylene oxide in the molar ratio of at least 1/1 in the presence of at least 0.01 mol of water for each mol of alkylene oxide and in the presence of up to about 0.1 mols of at least one catalyst selected from the group consisting of organic quaternary ammonium halides, organic quaternary phosphonium halides, organic sulfonium halides, and organic antimony halides per mol of alkylene oxide at a temperature above about 90°

C. and a total pressure selected to provide a partial pressure of carbon dioxide sufficient to produce more alkylene carbonate than mono alkylene glycol and to minimize production of higher glycols.

10. The process of claim 9 wherein said alkylene oxide is converted to alkylene carbonate with a selectivity of at least 90%.