IP Library Granted Patent US 8,962,117
Granted Patent B2
US 8,962,117 · App. 13/660,195 · Granted Feb 24, 2015

Process for producing bisphenol A with reduced sulfur content, polycarbonate made from the bisphenol A, and containers formed from the polycarbonate

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Quick Facts
Patent No.
US 8,962,117
App. No.
13/660,195
Granted
Feb 24, 2015
Kind
B2
Abstract

In one embodiment, a process for producing a bisphenol A product comprises: reacting phenol with acetone in the presence of a sulfur containing promoter to obtain a reaction mixture comprising bisphenol A, phenol, and the promoter; after reacting the phenol with the acetone, cooling to form a crystal stream comprising crystals of bisphenol A and phenol; separating the crystals from the crystal steam; melting the crystals to form a molten stream of bisphenol A, phenol, and sulfur; contacting the molten stream with a base to reduce a sulfur concentration in the molten stream and form a reduced sulfur stream; and removing phenol from the reduced sulfur stream to form a bisphenol A product. Also disclosed herein is a container comprising: a polycarbonate formed from a bisphenol A having a sulfur concentration of 0.5 to 15 ppm based upon the weight of the bisphenol A.

Claims (52)

1. A process for producing a bisphenol A product comprising:

reacting phenol with acetone in the presence of a sulfur containing promoter to obtain a reaction mixture comprising bisphenol A, phenol, and the promoter;

after reacting the phenol with the acetone, cooling the reaction mixture to form a crystal stream comprising crystals of bisphenol A and phenol;

separating the crystals from the crystal steam;

melting the crystals to form a molten stream of bisphenol A, phenol, and sulfur;

contacting the molten stream with a base to reduce a sulfur concentration in the molten stream and form a reduced sulfur stream; and

removing phenol from the reduced sulfur stream to form a bisphenol A product.

2. The process according to claim 1 , wherein the base comprises an alkali solution.

3. The process according to claim 1 , further comprising adding additional phenol to the molten stream prior to contacting the stream with a base.

4. The process according to claim 1 , wherein the molten stream is contacted with the base at a temperature of 70° C. to 120° C.

5. The process according to claim 4 , wherein the temperature is 80° C. to 100° C.

6. The process according to claim 1 , wherein the promoter comprises a catalyst selected from 3-mercaptopropionic acid, methyl mercaptan, ethyl mercaptan, 2,2-bis(methylthio)propane, mercaptocarboxylic acid, and combinations comprising at least one of the foregoing promoters.

7. The process according to claim 6 , wherein the promoter comprises 3-mercaptopropropionic acid.

8. The process according to claim 1 , wherein the base comprises an anion exchange resin.

9. The process according to claim 8 , wherein the anion exchange resin comprises a tert-amine divinylbenzene/styrene ion exchange copolymer.

10. The process according to claim 1 , wherein the sulfur concentration is reduced to 0.5 ppm to 15 ppm based upon the weight of the bisphenol A.

11. The process according to claim 10 , wherein the sulfur concentration is reduced to 2 ppm to 10 ppm based upon the weight of the bisphenol A.

12. The process according to claim 11 , wherein the sulfur concentration is reduced to 3 ppm to 8 ppm based upon the weight of the bisphenol A.

13. The process according to claim 1 , further comprising, prior to forming the crystal stream,

cooling the reaction mixture to form an initial crystal stream comprising initial crystals of bisphenol A and phenol;

separating the initial crystals from the initial crystal steam;

melting the initial crystals to form an initial molten stream; and

then performing the cooling to form the crystal steam according to claim 1 .

14. The process according to claim 13 , further comprising melt crystallizing the bisphenol A product.

15. A process for making polycarbonate, comprising:

reacting phenol with acetone in the presence of a sulfur containing promoter to obtain a reaction mixture comprising bisphenol A, phenol, and the promoter;

after reacting the phenol with the acetone, cooling the reaction mixture to form a crystal stream comprising crystals of bisphenol A and phenol;

separating the crystals from the crystal steam;

melting the crystals to form a molten stream of bisphenol A, phenol, and sulfur;

contacting the molten stream with a base to reduce a sulfur concentration in the molten stream and form a reduced sulfur stream;

removing phenol from the reduced sulfur stream to form a bisphenol A product; and

reacting, in the presence of a transesterification catalyst, a diaryl carbonate ester and the bisphenol A product.

16. A process for making polycarbonate, comprising:

reacting phenol with acetone in the presence of a sulfur containing promoter to obtain a reaction mixture comprising bisphenol A, phenol, and the promoter;

after reacting the phenol with the acetone, cooling the reaction mixture to form a crystal stream comprising crystals of bisphenol A and phenol;

separating the crystals from the crystal steam;

melting the crystals to form a molten stream of bisphenol A, phenol, and sulfur;

contacting the molten stream with a base to reduce a sulfur concentration in the molten stream and form a reduced sulfur stream;

removing phenol from the reduced sulfur stream to form a bisphenol A product;

forming a mixture of the bisphenol A product in aqueous caustic material;

adding the mixture to a water-immiscible solvent medium; and

contacting the reactants with a carbonate precursor in the presence of a catalyst to form the polycarbonate.

17. A container, comprising the polycarbonate from claim 16 .

18. A container, comprising a polycarbonate formed from a bisphenol A having a sulfur concentration of 0.5 ppm to 15 ppm based upon the weight of the bisphenol A.

19. The container according to claim 18 , wherein the container is a food container.

20. The container according to claim 18 , wherein the bisphenol A was formed using a sulfur containing promoter.

21. The container according to claim 18 , wherein the sulfur concentration is to 2 ppm to 10 ppm based upon the weight of the bisphenol A.

22. The container according to claim 21 , wherein the sulfur concentration is 3 ppm to 8 ppm based upon the weight of the bisphenol A.

23. The container according to claim 18 , wherein the container is a bottle.

24. The container according to claim 23 , wherein the bottle is selected from a baby bottle, beverage bottle, medical bottle, and personal care bottle.

25. The container according to claim 24 , wherein the bottle is a beverage bottle selected from a juice bottle, water bottle, carbonated drink bottle, alcoholic beverage bottle.

26. The container according to claim 24 , wherein the bottle is a beverage bottle selected from bottles having a capacity of two liters, a capacity of 20 ounces, a capacity of 16.9 ounces, a capacity of 12 ounces, a capacity of 6 ounces, and/or a filled weight of 200 to 800 grams.

Assignments (4)
CORRECTIVE ASSIGNMENT TO CORRECT THE 12/116841, 12/123274, 12/345155, 13/177651, 13/234682, 13/259855, 13/355684, 13/904372, 13/956615, 14/146802, 62/011336 PREVIOUSLY RECORDED ON REEL 033591 FRAME 0673. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded Aug 29, 2014
From: SABIC INNOVATIVE PLASTICS IP B.V.
To: SABIC GLOBAL TECHNOLOGIES B.V.
Reel/Frame 033663/0427 →
CORRECTIVE ASSIGNMENT TO CORRECT REMOVE 10 APPL. NUMBERS PREVIOUSLY RECORDED AT REEL: 033591 FRAME: 0673. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded Aug 28, 2014
From: SABIC INNOVATIVE PLASTICS IP B.V.
To: SABIC GLOBAL TECHNOLOGIES B.V.
Reel/Frame 033649/0529 →
CHANGE OF NAME Recorded Aug 22, 2014
From: SABIC INNOVATIVE PLASTICS IP B.V.
To: SABIC GLOBAL TECHNOLOGIES B.V.
Reel/Frame 033591/0673 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 11, 2012
From: BELFADHEL, HATEM ABDALLAH; DE BROUWER, JOHANNES; VIEVEEN, MARCEL; WOLD, CHRISTIAN; BRANDER, ERIC
To: SABIC INNOVATIVE PLASTICS IP B.V.
Reel/Frame 029447/0728 →