IP Library Granted Patent US 6,858,759
Granted Patent B2
US 6,858,759 · App. 10/639,929 · Granted Feb 22, 2005

Process for manufacture of bisphenols

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 6,858,759
App. No.
10/639,929
Granted
Feb 22, 2005
Kind
B2
Abstract

A method for the manufacture of bisphenols comprises introducing a combined feed stream comprising a feed stream and a recycle stream into a reactor system comprising at least one reactor containing a catalytic proportion of an acid catalyst and wherein the combined feed stream comprises a carbonyl compound and a stoichiometric excess of phenol; removing from the reactor system a reactor effluent; splitting the reactor effluent into a crystallization feed stream and an effluent recycle stream; extracting from said crystallization feed stream a bisphenol adduct, remainder comprising a mother liquor stream; dehydrating said mother liquor stream and said effluent recycle stream in a dehydrator wherein excess water and carbonyl compound are removed; and recycling the dehydrated mother liquor and the dehydrated effluent recycle stream back to the combined feed stream to effect improved production of p,p-bisphenol, along with increased reactor selectivity and reduced promoter quantities.

Claims (51)

1. A method for the manufacture of bisphenols comprising:

introducing a combined feed stream comprising a feed stream and a recycle stream into a reactor system comprising at least one reactor containing a catalytic proportion of an acid catalyst and wherein the combined feed stream comprises a carbonyl compound and an amount of greater than or equal to about 60 wt % phenol, wherein the weight percents are based on the total weight of the combined feed stream;

removing from the reactor system a reactor effluent;

splitting the reactor effluent into a crystallization feed stream and an effluent recycle stream;

extracting from said crystallization feed stream a bisphenol adduct, remainder comprising a mother liquor stream;

dehydrating said mother liquor stream and said effluent recycle stream in a dehydrator wherein excess water and carbonyl compound are removed; and

recycling the dehydrated mother liquor and the dehydrated effluent recycle stream back to the combined feed stream to effect improved production of p,p-bisphenol, along with increased reactor selectivity and reduced promoter quantities.

2. The method of claim 1 , wherein the phenol is an ortho-cresol, meta-cresol, 2,6-dimethylphenol, ortho-sec-butylphenol, 1,3,5 xylenol, tetramethylphenol, 2-methyl-6-tert.butylphenol, orthophenylphenol, ortho- and meta-chlorophenol, ortho-bromophenol, 2,6-dichlorophenol, or a combination comprising at least one of the foregoing phenols.

3. The method of claim 1 , wherein the carbonyl compound is acetone, methyl ethyl ketone, methyl propylketone, methyl vinyl acetone, acetophenone and cyclohexanone, or a combination comprising at least one of the foregoing ketones.

4. The method of claim 1 , wherein the carbonyl compound is acetone.

5. The method of claim 1 , wherein the effluent recycle stream comprises about 6 to about 22 wt % of reactor effluent.

6. The method of claim 1 , wherein effluent recycle stream comprises about 8 to about 20 wt % of reactor effluent.

7. The method of claim 1 , wherein carbonyl compound concentration in the combined feed stream is about 1 to about 8 wt % of the total weight of the combined fee stream.

8. The method of claim 1 , wherein p,p-bisphenol concentration in the combined feed stream is about 5 to about 20 wt % of the total weight of the combined feed stream.

9. The method of claim 1 , wherein the catalyst is a sulfonated polystyrene, poly(styrenedivinylbenzene) copolymers, sulfonated phenolformaldehyde resins, or a combination comprising at least one of the foregoing catalysts.

10. The method of claim 1 , wherein the catalyst is an acidic form of sulfonated polystyrene cross-linked with divinylbenzene having an activity of 1.0 and capable of handling a total hydraulic flow of 150 m 3 /hour.

11. The method of claim 1 wherein the catalyst comprises pendant sulfonic acid groups having about 2 to about 4% crosslinking of a divinylbenzene.

12. The method of claim 1 , wherein the promotor is a methyl mercaptan, ethyl mercaptan, propyl mercaptan, 3-mercaptopropionic acid, or a combination comprising at least one of the foregoing promotors.

13. The method of claim 1 , wherein the promotor is 3-mercapto propionic acid and is present in an amount of about 500 to about 10,000 ppm with respect to the total weight of the combined feed stream.

14. A process for the preparation of bisphenols comprising:

reacting acetone with an excess of phenol in a reactor containing a catalyst bed comprising an acidic form of sulfonated polystyrene cross-linked with divinylbenzene having an activity of 1.0, treated with 3-methyl propionic promotor;

splitting the reactor effluent into a crystallization feed stream and an effluent recycle stream, wherein the effluent recycle stream comprises about 6 to about 22 wt % of the reactor effluent;

extracting from the crystallization feed stream a bisphenol adduct to leave behind a mother liquor;

dehydrating the mother liquor and the effluent recycle stream to produce a recycle stream;

combining the recycle stream with a new feed stream to produce a combined feed stream wherein the combination of the recycle stream and feed stream results in an improved production of p,p-bisphenol or reduced levels of promotor.

15. A method of claim 14 , wherein the reactor inlet temperature is about 45° C. to about 60° C.

16. A method of claim 14 , wherein the p,p-bisphenol concentration in the combined feed stream is about 5 to about 20 wt % of the total weight of the combined feed.

17. A method of claim 14 , wherein the acetone concentration in the combined feed stream is about 1 to about 8 wt % of the total weight of the combined feed.

18. A method for manufacturing a polycarbonate comprising:

reacting p,p-bisphenol with a carbonate precursor, wherein the p,p-bisphenol is manufactured by a process comprising:

introducing a combined feed stream comprising a feed stream and a recycle stream into a reactor system comprising at least one reactor containing a catalytic proportion of an acid catalyst and wherein the combined feed stream comprises a carbonyl compound and a stoichiometric excess of phenol;

removing from the reactor system a reactor effluent;

splitting the reactor effluent into a crystallization feed stream and an effluent recycle stream;

extracting from said crystallization feed stream a bisphenol adduct, remainder comprising a mother liquor stream;

dehydrating said mother liquor stream and said effluent recycle stream in a dehydrator wherein excess water and carbonyl compound are removed; and

recycling the dehydrated mother liquor and the dehydrated effluent recycle stream back to the combined feed stream to effect the production of p,p-bisphenol.

19. The method of claim 18 , wherein the p,p-bisphenol is interfacially reacted with the carbonate precursor.

20. The method of claim 19 , wherein the carbonate precursor is a carbonyl halide.

21. The method of claim 20 , wherein the carbonyl halide is phosgene.

22. The method for claim 18 , wherein the polycarbonate has a number average molecular weight of about 3,000 to about 1,000,000 grams/mole.

23. A method for manufacturing a polycarbonate comprising:

reacting p,p-bisphenol with a carbonic acid diester, wherein the p,p-bisphenol is manufactured by a process comprising:

introducing a combined feed stream comprising a feed stream and a recycle stream into a reactor system comprising at least one reactor containing a catalytic proportion of an acid catalyst and wherein the combined feed stream comprises a carbonyl compound and a stoichiometric excess of phenol;

removing from the reactor system a reactor effluent;

splitting the reactor effluent into a crystallization feed stream and an effluent recycle stream;

extracting from said crystallization feed stream a bisphenol adduct, remainder comprising a mother liquor stream;

dehydrating said mother liquor stream and said effluent recycle stream in a dehydrator wherein excess water and carbonyl compound are removed; and

recycling the dehydrated mother liquor and the dehydrated effluent recycle stream back to the combined feed stream to effect the production of p,p-bisphenol.

24. The method of claim 23 , wherein reacting the p,p-bisphenol with the carbonic acid diester is conducted in a melt.

25. The method of claim 22 , wherein the carbonic acid diester is diphenyl carbonate.

26. The method for claim 22 , wherein the polycarbonate has a number average molecular weight of about 3,000 to about 1,000,000 grams/mole.

Assignments (2)
RELEASE OF SECURITY INTEREST Recorded Mar 17, 2014
From: CITIBANK, N.A.
To: SABIC INNOVATIVE PLASTICS IP B.V.
Reel/Frame 032459/0798 →
SECURITY AGREEMENT Recorded Aug 18, 2008
From: SABIC INNOVATIVE PLASTICS IP B.V.
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 021423/0001 →