Esterification reaction

• US 4,007,218 A
• Filed: 07/31/1975
• Issued: 02/08/1977
• Est. Priority Date: 12/07/1973
• Status: Expired due to Term

• Current Assignee: Standard Oil Company (BP PLC)
• Original Assignee: Standard Oil Company (BP PLC)
• Inventors: Ghanayem, Ibrahim, Trevillyan, Alvin E.
• Primary Examiner(s): Myers, Jane S.
• Application Number:
  US05/600,858
• Time in Patent Office: 558 Days
• Field of Search: 260/475 B, 260/485 S, 260/475 R, 260/485 R, 260/475 PN, 260/475 N, 260/485 L, 260/485 N, 260/479 S
• US Class Current: 560/99
• CPC Class Codes: C07C 69/44 Adipic acid esters

Abstract

Process of producing relatively pure esters, which comprises reacting a solution of organic acid compound in excess monohydroxy compound in the presence of a tetraalkyl titanate esterification catalyst to produce a monohydroxy solution of organic ester, treating the dissolved organic ester in the substantial absence of water at a temperature of at least 120° C. with solid alkaline earth metal oxide or hydroxide adding at least two mols of water per mol of alkaline earth metal at up to 100° C. and partitioning solid alkaline earth metal compound from the dissolved organic ester.

Claims

1. The process of producing relatively pure esters, which comprises reacting a solution of at least one organic polycarboxylic acid compound selected from the group consisting of phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, 2,5-dibromoterephthalic acid, trimellitic anhydride, trimellitic acid, adipic acid, adipic anhydride, and sebacic acid in the presence of a tetraalkyl titanate esterification catalyst in excess monohydroxy hydrocarbon compounds selected from the group consisting of alcohols containing from 1 to 24 carbon atoms and aromatic hydroxy compounds containing 6 to 18 carbon atoms to produce a monohydroxy solution of organic ester, treating the dissolved organic ester in the substantial absence of unbound water at a temperature of at least 120°

C with at least one solid alkaline earth metal compound selected from the group consisting of alkaline earth metal oxide and alkaline earth metal hydroxide, adding subsequently two to twenty mols of water per mol of alkaline earth compound to the dissolved ester at up to 100°

C and partitioning solid alkaline earth metal compound from the dissolved organic ester, wherein the concentration of alkaline earth metal compound is 0.1 to 35 equivalents per equivalent of acid material in the monohydroxy solution of organic ester.

2. The process of claim 1, wherein said tetraalkyl titanate is selected from the group consisting of tetraisopropyl titanate and tetrabutyl titanate.

3. The process of claim 2, wherein the alkaline earth metal compound is an alkaline earth metal hydroxide.

4. The process of claim 3 wherein said alkaline earth metal hydroxide is calcium hydroxide.

5. The process of claim 3, wherein said alkaline earth metal hydroxide is a hydrated alkaline earth metal oxide.

6. The process of claim 5, wherein said alkaline earth metal oxide is calcium oxide.

7. The process of claim 1, wherein said polycarboxylic acid compound is a trimellitic acid compound.

8. The process of claim 7, wherein said monohydroxy compound is used in a concentration of from about 1 to 10 moles per equivalent of polycarboxylic acid compound.

9. The process of claim 8, wherein said monohydroxy compound is 2-ethylhexanol.