Bisphenol-A plant yield enhancement

• US 8,039,679 B2
• Filed: 08/24/2006
• Issued: 10/18/2011
• Est. Priority Date: 10/07/2005
• Status: Active Grant

• Current Assignee: Badger Licensing LLC (TechnipFMC, plc)
• Original Assignee: Badger Licensing LLC (TechnipFMC, plc)
• Inventors: Evitt, Steven D., Fetsko, Stephen W., Chi, Chung-Ming
• Primary Examiner(s): KEYS, ROSALYND ANN
• Application Number:
  US12/066,630
• Publication Number:
  US 20090221858A1
• Time in Patent Office: 1,881 Days
• Field of Search: None
• US Class Current: 568/723
• CPC Class Codes: C07C 15/085 Isopropylbenzene
• CPC Class Codes: C07C 2/66 Catalytic processes
• CPC Class Codes: C07C 37/20 using aldehydes or ketones
• CPC Class Codes: C07C 37/72 by liquid-liquid treatment
• CPC Class Codes: C07C 37/74 by distillation
• CPC Class Codes: C07C 37/84 by crystallisation
• CPC Class Codes: C07C 39/16 Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
• CPC Class Codes: C07C 407/00 Preparation of peroxy compounds
• CPC Class Codes: C07C 409/10 Cumene hydroperoxide
• CPC Class Codes: C07C 45/53 of hydroperoxides
• CPC Class Codes: C07C 49/08 Acetone
• CPC Class Codes: Y02P 20/10 Process efficiency

Abstract

An improved process is provided for producing bisphenol-A (BPA) comprising steps of (1) contacting benzene and a C₃ alkylating agent to produce an alkylation effluent comprising cumene; (2) oxidizing the cumene to produce the corresponding hydroperoxide; (3) cleaving the hydroperoxide to produce product comprising phenol and acetone; (4) reacting acetone with phenol to form a reaction product stream comprising crude bisphenol-A product; (5) distilling the reaction product stream, while sending downstream to a BPA-phenol adduct crystallization and purification step, the resulting concentrated BPA phenolic feed stream; (6) producing BPA-phenol adduct crystals by crystallization of the concentrated BPA phenolic feed stream; (7) separating the BPA-phenol adduct crystals by solid-liquid separationr; (8) cracking a stream comprising at least a portion of said final mother liquor to recover a product; and (9) recovering and feeding the phenol product of step (8) to step (4) and/or step (7).

Claims

1. A process for producing bisphenol-A comprising the steps of:

(a) reacting acetone with a stoichiometric excess of phenol under acidic conditions to form a reaction product stream comprising crude bisphenol-A product, unreacted phenol, possibly unreacted acetone, water of condensation, and other reaction byproducts;

(b) distilling the reaction product stream from step (a) to distill off an unreacted phenol stream, possibly an unreacted acetone stream, and the water of condensation, and sending a concentrated BPA phenolic feed stream consisting essentially of phenol, bisphenol-A and byproducts downstream to BPA-phenol adduct crystallization and purification steps;

(c) cooling and crystallizing BPA-phenol adduct crystals from the concentrated BPA phenolic feed stream by vaporization of an alkane hydrocarbon or mixture of hydrocarbons containing from 4 to 6 carbons;

(d) separating BPA-phenol adduct crystals by solid-liquid separation and washing same in one or multiple stages with a phenol wash stream comprising at least a portion of the unreacted phenol stream recovered from step (b), or spent phenol wash or mother liquor streams from subsequent crystallization, solid-liquid separation, and wash steps, to produce final washed BPA-phenol adduct, final spent wash and final mother liquor;

(e) cracking a stream comprising at least a portion of said final mother liquor of step (d) in a reactor with a basic catalyst under reaction conditions including a temperature from about 200 to about 350°

C., a pressure from about 1.33 to 101.3 kPa-a, a residence time from about 5 to about 600 minutes and a catalyst concentration from about 5 to about 1500 wppm, to recover from about 60 to about 90 wt. % of said portion of said final mother liquor cracked stream as phenol having a purity level of from about 95 to about 100 wt. %, and from about 10 to about 40 wt. % of said cracked stream as heavy residue byproduct; and

(f) recovering and feeding the phenol product of step (e) to step (a) and/or step (d).

2. The process of claim 1 wherein the phenol wash stream of step (d) includes at least a portion of the unreacted phenol stream recovered from step (b).

3. The process of claim 1 wherein the portion of said final mother liquor of step (d) in step (e) is from about 0.5 to about 20 wt. %.

4. The process of claim 1 wherein step (a) is conducted in the presence of an acid catalyst selected from the group consisting of a homogeneous catalyst, a heterogeneous catalyst and combinations thereof.

5. The process of claim 4 wherein step (a) is conducted in the presence of an added promoter selected from the group consisting of methyl mercaptan, ethyl mercaptan, 2,2-bis(methylthio)propane, mercaptocarboxylic acid, and promoter-bound resins.

6. The process of claim 1 wherein the reaction conditions of step (e) include a temperature from about 215 to about 260°

C., and a pressure from about 13.3 to 46.7 kPa-a.

7. The process of claim 1 wherein at least a portion of the acetone and phenol of step (a) results from steps comprising:

(1) contacting benzene and a C₃ alkylating agent under alkylation conditions with an alkylation catalyst in a reaction zone to produce an alkylation effluent comprising cumene;

(2) oxidizing the cumene from step (1) to produce the corresponding hydroperoxide; and

(3) cleaving the hydroperoxide from step (2) to produce product comprising phenol and acetone;

and said cracking stream of step (e) comprises from about 0.5 to about 20 wt. % of said final mother liquor of step (d).

8. The process of claim 7 wherein said alkylating agent comprises an aliphatic or aromatic organic compound having one of more available alkylating aliphatic groups of 3 carbon atoms, or mixtures thereof.

9. The process of claim 8 wherein said alkylating agent is selected from the group consisting of propylene, propanol, propionaldehyde, propyl halide and mixtures thereof.

10. The process of claim 7, wherein said alkylation effluent produced in step (1) comprises polyisopropylbenzenes and the process further comprises contacting said polyisopropylbenzenes with benzene in the presence of a transalkylation catalyst to produce cumene.

11. The process of claim 7, wherein the cleaving step (3) is conducted in the presence of a catalyst comprising at least one of sulfuric acid, perchloric acid, phosphoric acid, hydrochloric acid, p-toluenesulfonic acid, ferric chloride, boron trifluoride, sulfur dioxide and sulfur trioxide.

12. The process claim 7, wherein the cleaving step (3) is conducted at a temperature from about 20°

C. to about 150°

C., a pressure from about 0 to about 7000 kPa and a liquid hourly space velocity (LHSV) based on the hydroperoxide from about 0.1 to about 100 hr<sup>−

1</sup>.

13. The process of claim 7, wherein step (a) is conducted in the presence of an added promoter selected from the group consisting of methyl mercaptan, ethyl mercaptan, 2,2-bis(methylthio)propane, mercaptocarboxylic acid, and promoter-bound resins.

14. The process of claim 7, wherein the reaction conditions of step (e) include a temperature from about 215 to about 260°

C., and a pressure from about 13.3 to 46.7 kPa-a.