Method to manufacture bisphenol A

• US 5,198,591 A
• Filed: 11/22/1991
• Issued: 03/30/1993
• Est. Priority Date: 11/24/1990
• Status: Expired due to Fees

• Current Assignee: Instytut Ciezkiej Ciezkiej Organicznej "Blachownia", Zaklady Chemiczne "Blachownia"
• Original Assignee: ABB Lummus Crest Inc., Instytut Ciezkiej Syntezy Organicznej "Blachownia", Zaklady Chemiczne "Blachownia"
• Inventors: Swiderski, Zbigniew, Mroz, Jerzy, Zajac, Eugeniusz, Olkowska, Janina, Bek, Teodor, Marszycki, Jerzy, Kolt, Jozef, Rzodeczko, Anna, Kiedik, Maciej
• Primary Examiner(s): LONE, WERREN
• Application Number:
  US07/797,428
• Time in Patent Office: 494 Days
• Field of Search: 568/722, 568/727, 568/728, 568/749, 568/753, 568/781, 568/782, 568/806, 568/724, 23/295 R
• US Class Current: 568/727
• CPC Class Codes: C07C 37/20 using aldehydes or ketones
• CPC Class Codes: C07C 37/52 by splitting polyaromatic compounds, e.g. polyphenolalkanes
• CPC Class Codes: C07C 37/84 by crystallisation
• CPC Class Codes: C07C 39/04 Phenol
• CPC Class Codes: C07C 39/06 Alkylated phenols
• CPC Class Codes: C07C 39/16 Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes

Abstract

The invention relates to a process for obtaining a high purity bisphenol from a post-reaction mixture resulting from the step of synthesis of phenol and acetone in the presence of a strong acid cation exhanger catalyst, by the way of crystallation and separation by distillation followed by recovery of bisphenol-A from the step of thermal catalytic decomposition of by product of the principal process technology in a multistage process.

Claims

1. A process to obtain high-purity bisphenol A from a post-reaction mixture resulting from the step of synthesis from phenol and acetone, in the presence of a strong acid cation-exchanger catalyst, by way of crystallization and separation by distillation followed by recovery of bisphenol A from the step of thermal catalytic decomposition of by-products of the principal process technology in a multistage process, the by-products being selected from the group consisting of o,p isomers of bisphenol A, Dianin compound, trisphenols, polyphenols and colored substances, wherein unit (1) of the reaction system is the unit where the following reactions are conducted simultaneously:

reaction of phenol with acetone, reaction of phenol with recycled p-isopropenylphenol, and reactions of isomerizational rearrangement of bisphenol A isomers, at a temperature of about 60°

-95°

C. in the presence of a micro- and macroporous catalyst mixture, whereas the post-reaction mixture is cooled together with acetone and water to obtain a bisphenol-A/phenol slurry adduct in a phenolic solution in unit (2) and the bisphenol-A/phenol slurry adduct in a phenolic solution obtained in unit (2) is separated in unit (3) to obtain crystalline bisphenol-A/phenol adduct and phenol liquor I, whereafter the crystalline adduct is washed with phenolic solution and the crystalline bisphenol-A/phenol adduct obtained in unit (3) is dissolved in at least one of a portion of the phenol liquor I and a phenol liquor II in unit (4) and the mixture is cooled to obtain bisphenol-A/phenol adduct slurry in a phenolic solution, whereafter the slurry obtained in unit (4) is separated in unit (5) into crystalline bisphenol-A/phenol adduct and the phenol liquor II to be sent back to unit (3) while washing the crystalline bisphenol-A/phenol adduct with phenol solution, whereas the high-purity bisphenol A is separated in unit (6) by removing phenol from bisphenol-A/phenol adduct obtained in unit (5), phenol liquor I obtained in unit (3) is distilled in unit (7) by removing water and acetone and part of phenol therefrom, whereas dewartered phenol liquor is sent back to unit (1), whereafter part of the phenol liquor obtained in at least one of unit (3) and unit (7) is decomposed by thermal catalytic decomposition in unit (8) to obtain phenol-containing distillate, p-isopropenylphenol and the process by-products, while reactive components of the distillate obtained in unit (8) are rearranged catalytically in unit (9) leaving the p-isopropenylphenol contained therein substantially intact, and the rearranged distillate is sent back to unit (1) of the process of the invention.

2. A process for preparing bisphenol A, comprising the steps of:

(a) simultaneously (1) reacting phenol with acetone, (2) reacting p-isopropenylphenol with phenol, and (3) subjecting isomers of bisphenol A to isomerization in a single reactant mixture containing a strong acid cation-exchange resin catalyst at a temperature of about 60°

-95°

C. to form a post-reaction mixture containing bisphenol A and phenol, the bisphenol A being produced in each of reactions (1)-(3),

(b) cooling the post-reaction mixture to form a first slurry containing a first bisphenol A-phenol adduct,

(c) subjecting the first slurry to solid-liquid separation to obtain a first crystalline bisphenol A-phenol adduct and a first phenolic solution,

(d) removing water and phenol from at least a portion of the first phenolic solution to form a dewatered first phenolic solution, and recycling a portion of the dewatered first phenolic solution into the reactant mixture of step (a),

(e) washing the first crystalline bisphenol A-phenol adduct with a portion of a second phenolic solution,

(f) dissolving the washed first crystalline bisphenol A-phenol adduct in at least one of a portion of the dewatered first phenolic solution and a portion of the second phenolic solution,

(g) cooling the dissolved mixture from step (f) to form a second slurry containing a second bisphenol A-phenol adduct,

(h) subjecting the second slurry to solid-liquid separation to obtain the second phenolic solution, at least a portion of which is recycled to step (e), and a second crystalline bisphenol A-phenol adduct,

(i) washing the second crystalline bisphenol A-phenol adduct with a third phenolic solution,

(j) removing phenol from the washed second crystalline bisphenol A-phenol adduct to obtain bisphenol A, and

(k) treating the non-watered portion of the first phenolic solution and any remaining portion of the dewatered first phenolic solution to obtain a distillate comprising phenol, p-isopropenylphenol and isomers of bisphenol A, and recycling the distillate to step (a).

3. A process according to claim 2, wherein only non-dewatered phenolic solution is treated in step (k).

4. A process according to claim 2, wherein step (k) comprises subjecting the non-dewatered portion of the first phenolic solution and any remaining portion of the dewatered first phenolic solution to thermal catalytic decomposition.

5. A process as claimed in claim 4, wherein step (k) further comprises the step of subsequently catalytically rearranging the distillate, leaving the p-isopropenylphenol substantially intact.

6. A process as claimed in claim 2, wherein the reactant mixture of step (a) contains about 10-30 wt % by-products comprising at least one member of the group consisting of isomers of bisphenol A, Dianin compound, trisphenols, polyphenols, and colored substances.

7. A process according to claim 2, wherein the post-reaction mixture contains about 15-35 wt % bisphenol A.

8. A process according to claim 2, wherein the post-reaction mixture contains about 20-30 wt % bisphenol A.

9. A process according to claim 2, wherein the first slurry of step (b) contains about 2-6 wt % acetone and about 1-4 wt % water.

10. A process according to claim 2, wherein the first crystalline bisphenol A-phenol adduct is washed in step (e) with the second phenolic solution in a amount of about 0.2-2.0 parts by weight of second phenolic solution per 1 part by weight of adduct.

11. A process according to claim 2, wherein the third phenolic solution used in step (i) comprises about 1-3 parts by weight fresh phenol per 1 part by weight phenol which is removed in step (j).

12. A process according to claim 2, wherein phenol is removed from the washed second crystalline bisphenol A-phenol adduct by vacuum distillation and steam stripping.

13. A process according to claim 2, wherein step (d) comprises a distillation process in which phenol is removed from the first phenolic solution in an amount of about 0.1-0.3 parts by weight of phenol per part by weight of first phenolic solution.

14. A process according to claim 4, wherein the non-dewatered portion of the first phenolic solution is about 0.05-0.2 parts by weight of the first phenolic solution obtained in step (c).

15. A process according to claim 4, wherein the thermal catalytic decomposition is conducted at a temperature of about 200°

-300°

C. in the presence of a catalyst comprising at least one member selected from the group consisting of Na₂ HPO₂, NaHCO₃, Na₂ CO₃ and NaOH.

16. A process according to claim 5, wherein catalytic rearrangement is effected in the presence of 0.05-0.5% by weight of oxalic acid.

17. A process according to claim 4, wherein the third phenolic solution of step (i) comprises fresh phenol.

18. A process according to claim 4, wherein the third phenolic solution of step (i) consists essentially of fresh phenol and removed phenol from step (j) in a ratio of 1-3 parts by weight fresh phenol per 1 part by weight removed phenol from step (j).

19. A process according to claim 2, wherein the reactant mixture of step (a) contains about 10-30 wt % by-products comprising at least 1 member of the group consisting of isomers of bisphenol A, Dianin compound, trisphenols, polyphenols and colored substances, the post-reaction mixture contains about 15-35 wt % bisphenol A, the first slurry of step (b) contains about 2-6 wt % acetone and about 1-4 wt % water, step (d) comprises a distillation process in which phenol is removed from the first phenolic solution in an amount of about 0.1-0.3 parts by weight of phenol per part by weight of first phenolic solution, the first crystalline bisphenol A-phenol adduct is washed in step (e) with the second phenolic solution in an amount of about 0.2-2.0 parts by weight of second phenolic solution per 1 part by weight of adduct, and the third phenolic solution of step (i) consists essentially of fresh phenol and removed phenol from step (j) in a ratio of 1-3 parts by weight fresh phenol per 1 part by weight removed phenol from step (j).

20. A process according to claim 5, wherein the non-dewatered portion of the first phenolic solution is about 0.05-0.2 parts by weight of the first phenolic solution obtained in step (c), and the thermal catalytic decomposition is conducted at a temperature of about 200°

-300°

C. in the presence of a catalyst comprising at least one member selected from the group consisting of Na₂ HPO₂, NaHCO₃, Na₂ CO₃ and NaOH.