Process for recovering 2,2-bis(4-hydroxyphenyl)propane from an adduct of 2,2-bis(4-hydroxyphenyl)propane and phenol

• US 4,212,997 A
• Filed: 06/27/1978
• Issued: 07/15/1980
• Est. Priority Date: 06/27/1978
• Status: Expired due to Term

• Current Assignee: General Electric Company
• Original Assignee: General Electric Company
• Inventors: Lee, Michael C., Adams, John N., Kissinger, Gaylord M.
• Primary Examiner(s): Morgenstern, Norman
• Application Number:
  US05/919,667
• Time in Patent Office: 749 Days
• Field of Search: 568/724, 568/728
• US Class Current: 568/724
• CPC Class Codes: C07C 37/685 Processes comprising at least two steps in series
• CPC Class Codes: C07C 37/84 by crystallisation
• CPC Class Codes: C07C 39/16 Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes

Abstract

The compound 2,2-bis(4-hydroxyphenyl)propane is recovered in the form of rhombic crystals from an essentially non-crystalline mixture comprising 2,2-bis(4-hydroxyphenyl)propane, organic by-products of the condensation reaction of phenol and acetone, and phenol by lowering the temperature of the mixture from an elevated state to a temperature which is low enough to cause the separation of the phenol and 2,2-bis(4-hydroxyphenyl)propane in equimolar proportions as a crystalline adduct, recovering the adduct, forming a mixture of the adduct and water at an elevated temperature sufficient to completely melt the adduct, and thereafter lowering the temperature of the mixture of water and melted adduct to cause the separation of the 2,2-bis(4-hydroxyphenyl)propane in the form of rhombic crystals substantially free of the phenol. The crystals are easily handled and recovered by means such as filtration or centrifugation, and they can be formed into high quality polycarbonate molding resins.

Claims

1. A process for recovering 2,2-bis(4-hydroxyphenyl)propane in the form of rhombic crystals from a non-crystalline mixture at an elevated temperature above room temperature, the reaction mixture comprising 2,2-bis(4-hydroxyphenyl)propane, organic by-products resulting from the condensation reaction of phenol and acetone, and phenol, wherein said phenol is present in at least an equimolar amount with respect to said 2,2-bis(4-hydroxyphenyl)propane, the process comprising:

(a) lowering the temperature of said mixture from an elevated temperature at which the 2,2-bis(4-hydroxyphenyl)propane is soluble to a temperature sufficient to cause the separation from said mixture of said 2,2-bis(4-hydroxyphenyl) propane and phenol in equimolar proportions as a crystalline adduct and recovering the adduct;

(b) forming an admixture of said adduct of step (a) with an excess of water at an elevated temperature which is at least sufficient to completely melt the adduct, the water being present in an amount at least sufficient to retain the phenol portion of the adduct upon subsequent crystallization therefrom of the 2,2-bis(4-hydroxyphenyl)propane;

(c) lowering the temperature of said mixture of water and melted adduct to a temperature sufficient to cause the selective separation therefrom of the 2,2-bis(4-hydroxyphenol)propane portion of the adduct in the form of rhombic crystals substantially free of said phenol portion; and

(d) recovering said rhombic crystals of 2,2-bis(4-hydroxyphenyl)propane.

2. A process as defined in claim 1 which further comprises:

(e) contacting the recovered rhombic crystals of 2,2-bis(4-hydroxyphenyl)propane with a liquid selected from among water, organic hydrocarbons or mixtures thereof in which said 2,2-bis(4-hydroxyphenyl)propane is insoluble or only slightly soluble, to remove adsorbed water soluble and/or organic solvent soluble impurities therefrom.

3. A process as defined in claim 1 wherein in step (a) the temperature of said non-crystalline mixture comprising 2,2-bis(4-hydroxyphenyl)propane, organic by-products and a phenol is lowered to less than about 45°

C.

4. A process as defined in claim 3 wherein in step (a) the temperature is lowered to a value in the range of from about 38°

to about 42°

C.

5. A process as defined in claim 1 wherein in step (b) the weight ratio of water to the phenol portion of said adduct is in the range of from about 25:

1 to about 31;

1.

6. A process as defined in claim 1 wherein step (b) is conducted at a temperature in the range of from about 80°

to about 90°

C.

7. A process as defined in claim 1 wherein in step (c) the temperature of said mixture of water and melted adduct is lowered to a temperature in the range of from about 45°

to about 50°

C.

8. A process as defined in claim 1 wherein the recovered adduct of step (a) is contacted with phenol to remove adsorbed impurities prior to treatment with step (b).

9. A process as defined in claim 2 wherein the organic hydrocarbon is a halohydrocarbon.

10. A process as defined in claim 9 wherein the halohydrocarbon is methylene chloride.

11. A process for recovering 2,2-bis(4-hydroxyphenyl)propane in the form of rhombic crystals from a non-crystalline mixture at an elevated temperature above room temperature, the reaction mixture comprising 2,2-bis(4-hydroxyphenyl)propane, organic by-products resulting from the condensation reaction of phenol and acetone, and phenol, wherein said phenol is present in at least an equimolar amount with respect to said 2,2-bis(4-hydroxyphenyl)propane, the process comprising:

(a) lowering the temperature of said mixture from an elevated temperature at which the 2,2-bis(4-hydroxyphenyl)propane is soluble to a temperature in the range of from about 38°

to about 42°

C. and sufficient to cause the separation from said mixture of said 2,2-bis(4-hydroxyphenyl)propane and phenol in equimolar proportions as a crystalline adduct and recovering the adduct;

(b) forming an admixture of said adduct of step (a) with an excess of water at an elevated temperature in the range of from about 80°

to about 90°

C. and which is at least sufficient to completely melt the adduct, the water being present in an amount of from about 25;

1 to about 31;

1 with respect to the phenol portion of the adduct and at least sufficient to retain the phenol portion of the adduct upon subsequent crystallization therefrom of the 2,2-bis(4-hydroxyphenyl)propane;

(c) lowering the temperature of said mixture of water and melted adduct to a temperature in the range of from about 45°

to about 50°

C. and sufficient to cause the selective separation therefrom of the 2,2-bis(4-hydroxyphenyl)propane portion of the adduct in the form of rhombic crystals substantially free of said phenol portion; and

(d) recovering said rhombic crystals of 2,2-bis(4-hydroxyphenyl)propane.