Process for preparing a bisphenol

• US 5,288,926 A
• Filed: 02/04/1993
• Issued: 02/22/1994
• Est. Priority Date: 03/02/1992
• Status: Expired due to Term

• Current Assignee: The Dow Chemical Company (Dow, Inc.)
• Original Assignee: The Dow Chemical Company (Dow, Inc.)
• Inventors: Tank, Dieter, Wallbaum, Ulrich, Frey, Johann-Wilhelm, Patrascu, Emil, Gressmann, Jochen
• Primary Examiner(s): LONE, WERREN
• Application Number:
  US08/013,603
• Time in Patent Office: 383 Days
• Field of Search: 568/722, 568/727, 568/723, 568/728, 568/724
• US Class Current: 568/727
• CPC Class Codes: C07C 37/20 using aldehydes or ketones
• CPC Class Codes: C07C 37/82 by solid-liquid treatment; by chemisorption
• CPC Class Codes: C07C 39/04 Phenol
• CPC Class Codes: C07C 39/16 Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
• CPC Class Codes: Y02P 20/52 using catalysts, e.g. selective catalysts

Abstract

Bisphenols are prepared by

a) reacting a phenolic compound with a carbonyl compound in a reaction mixture, containing the carbonyl compound, a stoichiometric excess of the phenolic compound and a catalyst, to produce a product mixture containing a bisphenol,

b) separating bisphenol from the product mixture to leave a mother liquor and

c) recycling at least a portion of the mother liquor to the reaction mixture.

At least a portion of the phenolic compound is contacted with a strongly acidic cation exchange resin and a strongly basic anion exchange resin before the phenolic compound is used in the reaction step a) and/or at least a portion of the product mixture and/or at least a portion or the mother liquor is contacted with a strongly acidic cation exchange resin and a strongly basic anion exchange resin before mother liquor is recycled to the reaction mixture.

Claims

1. A process of preparing a bisphenol comprising the steps of:

a) reacting a phenolic compound selected from the group consisting of phenol, cresols, xylenols, chlorophenols, thymol, carvacrol, cumenol, 2-methyl-6-ethylphenol, 2,4-dimethyl-3-ethylphenol, 4-ethylphenol, 2-ethyl-4-methylphenol, 2,3,6-trimethylphenol, 2-methyl-4-tertiary-butylphenol, 2,4-ditertiary-butyl-phenol, 4-methyl-2-tertiary-butylphenol, 2-teritary-butyl-4-methylphenol, 2,3,5,6-tetramethylphenol, 2,6-dimethylphenol, 2,6- ditertiary-butylphenol, 3,5-dimethylphenol, 3,5-diethylphenol, 2-methyl-3,5-diethylphenol, o-phenylphenol, p-phenylphenol, tetraphenolethane, the naphthols and phenanthrol with a carbonyl compound having the formula;

##STR3## wherein R₁ is selected from the group consisting of aliphatic, cycloaliphatic and aromatic radicals, and R₂ is selected from the group consisting of aliphatic, cycloaliphatic, aromatic radicals and hydrogen in a reaction mixture, containing said carbonyl compound, a stoichiometric excess of said phenolic compound and a strongly acidic ion exchange resin catalyst, to produce a product mixture containing a bisphenol;

b) separating bisphenol from the product mixture to leave a motor liquor; and

c) recycling at least a portion of the mother liquor to the reaction mixture,

wherein at least one of the following steps is conducted;

i) at least a portion of the phenolic compound is contacted with a strongly acidic cation exchange resin and a strongly basic anion exchange resin before the phenolic compound is used in reaction step a);

ii) at least a portion of the product mixture is contacted with a strongly acidic cation exchange resin and a strongly basic anion exchange resin before mother liquor is recycled to the reaction mixture;

or

iii) at least a portion of the mother liquor is contacted with a strongly acidic cation exchange resin and a strongly basic anion exchange resin before mother liquor is recycled to the reaction mixture.

2. The process of claim 1, wherein at least a portion of both the phenolic compound and the mother liquor is contacted with a strongly acidic cation exchange resin and a strongly basic anion exchange resin.

3. The process of claim 1, wherein the strongly acidic cation exchange resin and the strongly basic anion exchange resin are arranged in a mixed bed.

4. The process of claim 2, wherein the strongly acidic cation exchange resin and the strongly basic anion exchange resin are arranged in a mixed bed.

5. The process of claim 3, wherein the mixed bed contains from 50 to 70 weight percent of the strongly acidic cation exchange resin, based on the total of the cation and anion exchange resin.

6. The process of claim 4, wherein the mixed bed contains from 50 to 70 weight percent of the strongly acidic cation exchange resin, based on the total of the cation and anion exchange resin.

7. The process of claim 1 wherein the strongly acidic cation exchange resin contains --SO₃ H groups.

8. The process of claim 1 wherein the strongly basic anion exchange resin contains --NR₃ R₄ R₅ OH groups wherein R₃ and R₄ are, each independently, hydrogen or C_1-6 -alkyl, and R₅ is hydrogen, C_1-6 -alkyl, hydroxy-C_1-3 -alkyl or a mono- or di-C_1-6 -alkylaminoethylene group.

9. The process of claim 1 wherein the strongly acidic cation exchange resin contains a matrix of a cross-linked polystyrene or a cross-linked poly(alpha-methylstyrene) or a cross-linked polymer of styrene or alpha-methylstyrene which is substituted at the benzene ring with C_1-6 -alkyl Or halogeno-C_1-6 -alkyl and the resin is in the form of beads which have a decreased level of cross-linkages in the shell area as compared to the core area.

10. The process of claim 1 wherein the strongly basic anion exchange resin contains a matrix of a cross-linked polystyrene or a cross-linked poly(alpha-methylstyrene) or a cross-linked polymer of styrene or alpha-methylstyrene which is substituted at the benzene ring with C_1-6 -alkyl or halogeno-C_1-6 -alkyl and the resin is in the form of beads which have a decreased level of cross-linkages in the shell area as compared to the core area.

11. The process of claim 1 wherein at least one member of the group consisting of product mixture, mother liquor and phenolic compound is contacted with the strongly acidic cation exchange resin and the strongly basic anion exchange resin at a temperature of form about 40°

to about 95°

C.

12. The process of claim 1 wherein water and carbonyl compound are removed from the product mixture before bisphenol is separated from the product mixture.

13. The process of claim 1 wherein the carbonyl compound is selected from the group consisting of acetone, 1,3-dichloroacetone, dimethyl ketone, methyl ethyl ketone, diethyl ketone, dibutyl ketone, methyl isobutyl ketone, cyclohexanone, fluoroenone, propionylphenone, methyl amyl ketone, mesityl oxide, cyclopentanone, acetophenone, formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde and benzaldehyde.

14. The process of claim 1 wherein the carbonyl compound is acetone or fluorenone.

15. The process of claim 1 wherein phenol is reacted with acetone to produce bisphenol A.

16. The process of claim 15 wherein bisphenol A is separated from the product mixture in the form of a bisphenol A/phenol adduct.

17. The process of claim 16 wherein bisphenol A/phenol adduct is washed with phenol which has been contacted with a strongly acidic cation exchange resin and a strongly basic anion exchange resin.

18. A bisphenol produced according to the process of claim 1.

19. Bisphenol A produced according to the process of claim 16.