ROBUST PROMOTER CATALYST SYSTEM
A modified ion exchange resin catalyst having an attached dimethyl thiazolidine promoter is disclosed. Also disclosed is a process for catalyzing condensation reactions between phenols and ketones, wherein reactants are contacted with a modified ion exchange resin catalyst having an attached dimethyl thiazolidine promoter. Also disclosed is a process for catalyzing condensation reactions between phenols and ketones that does not utilize a bulk promoter.
1 . A catalyst system comprising a cross-linked, sulfonated ion exchange resin catalyst and a dimethyl thiazolidine promoter.
2 . The catalyst system of claim 1 , wherein the cross-linked, sulfonated ion exchange resin comprises a plurality of sulfonic acid groups and has a degree of cross-linking of from about 1% to about 4%.
3 . The catalyst system of claim 1 , wherein the cross-linked, sulfonated ion exchange resin has a degree of cross-linking of from about 1.5% to about 2.5%.
4 . The catalyst system of claim 1 , wherein the cross-linked, sulfonated ion exchange resin has a degree of cross-linking of about 2%.
5 . The catalyst system of claim 1 , wherein the dimethyl thiazolidine promoter is at least partially bound to the cross-linked, sulfonated ion exchange resin.
6 . The catalyst system of claim 1 , wherein at least a portion of the dimethly thiazolidine promoter is covalently bound to the cross-linked, sulfonated ion exchange resin.
7 . The catalyst system of claim 1 , wherein at least a portion of the dimethyl thiazolidine promoter is ionically bound to the cross-linked, sulfonated ion exchange resin.
8 . The catalyst system of claim 2 , wherein the dimethyl thiazolidine promoter is bound to from about 18% to about 25% of the sulfonic acid groups of the cross-linked, sulfonated ion exchange resin.
9 . The catalyst system of claim 2 , wherein the dimethyl thiazolidine promoter is bound to from about 20% to about 24% of the sulfonic acid groups of the cross-linked, sulfonated ion exchange resin.
10 . The catalyst system of claim 2 , wherein the dimethyl thiazolidine promoter is bound to about 22% of the sulfonic acid groups of the cross-linked, sulfonated ion exchange resin.
11 . The catalyst system of claim 1 , wherein the cross-linked, sulfonated ion exchange resin comprises a polystyrene based ion exchange resin.
12 . The catalyst system of claim 1 , wherein the cross-linked, sulfonated ion exchange resin comprises a polystyrene based ion exchange resin having a degree of cross-linking of from about 1% to about 4%, and wherein at least a portion of the dimethyl thiazolidine promoter is ionically bound to the ion exchange resin.
13 . The catalyst system of claim 1 , wherein the cross-linked, sulfonated ion exchange resin comprises a polysiloxane based ion exchange resin.
14 . The catalyst system of claim 1 , wherein the cross-linked, sulfonated ion exchange resin comprises a polysiloxane based ion exchange resin having a degree of cross-linking of from about 1% to about 4%, and wherein at least a portion of the dimethyl thiazolidine promoter is ionically bound to the ion exchange resin.
15 . An attached promoter catalyst system comprising an ion exchange resin and a dimethyl thiazolidine promoter, wherein the catalyst system is more resistant to hydroxyacetone than a conventional bulk promoter system.
16 . The attached promoter catalyst system of claim 15 , wherein the catalyst system can maintain at least about 60% of its initial performance after 200 hours of operation in the presence of about 10 ppm hydroxyacetone.
17 . The attached promoter catalyst system of claim 15 , wherein the catalyst system can maintain at least about 75% of its initial performance after 200 hours of operation in the presence of about 10 ppm hydroxyacetone.
18 . The attached promoter catalyst system of claim 15 , wherein the catalyst system is substantially unaffected, during operation, by exposure to up to about 1,000 ppm of alcohol.
19 . The attached promoter catalyst system of claim 15 , wherein the catalyst system is substantially unaffected, during operation, by exposure to up to about 3,000 ppm of alcohol.
20 . The attached promoter catalyst system of claim 15 , wherein the catalyst system is substantially unaffected by recycled bisphenol-A impurities.
21 . The attached promoter catalyst system of claim 15 , wherein the catalyst system, in a condensation reaction, can selectively catalyze the production of p,p-bisphenol-A in a ratio of at least about 25:1 (p,p-bisphenol-A:o,p-bisphenol-A).
22 . The attached promoter catalyst system of claim 15 , wherein the catalyst system, in a condensation reaction, can selectively catalyze the production of p,p-bisphenol-A in a ratio of at least about 30:1 (p,p-bisphenol-A:o,p-bisphenol-A).
23 . A method for catalyzing a condensation reaction, the method comprising contacting two or more reactants with a modified ion exchange resin catalyst in the absence of a bulk promoter.
24 . The method of claim 23 , wherein the method does not utilize a 3-mercaptopropionic acid bulk promoter.
25 . The method of claim 23 , wherein the modified ion exchange resin catalyst comprises a cross-linked, sulfonated ion exchange resin.
26 . The method of claim 25 , wherein the cross-linked, sulfonated ion exchange resin comprises a plurality of sulfonic acid groups and has a degree of cross-linking of from about 1% to about 4%.
27 . The method of claim 25 , wherein the cross-linked, sulfonated ion exchange resin has a degree of cross-linking of from about 1.5% to about 2.5%.
28 . The method of claim 25 , wherein the cross-linked, sulfonated ion exchange resin has a degree of cross-linking of about 2%.
29 . The method of claim 25 , wherein the modified ion exchange resin catalyst comprises an attached dimethyl thiazolidine promoter.
30 . The method of claim 29 , wherein the dimethyl thiazolidine promoter is at least partially bound to the cross-linked, sulfonated ion exchange resin.
31 . The method of claim 29 , wherein at least a portion of the dimethly thiazolidine promoter is covalently bound to the cross-linked, sulfonated ion exchange resin.
32 . The method of claim 29 , wherein at least a portion of the dimethyl thiazolidine promoter is ionically bound to the cross-linked, sulfonated ion exchange resin.
33 . The method of claim 29 , wherein the dimethyl thiazolidine promoter is bound to from about 18% to about 25% of the sulfonic acid groups of the cross-linked, sulfonated ion exchange resin.
34 . The method claim 29 , wherein the dimethyl thiazolidine promoter is bound to from about 20% to about 24% of the sulfonic acid groups of the cross-linked, sulfonated ion exchange resin.
35 . The method of claim 29 , wherein the dimethyl thiazolidine promoter is bound to about 22% of the sulfonic acid groups of the cross-linked, sulfonated ion exchange resin.
36 . The method of claim 29 , wherein the cross-linked, sulfonated ion exchange resin comprises a polystyrene based ion exchange resin.
37 . The method of claim 29 , wherein the cross-linked, sulfonated ion exchange resin comprises a polystyrene based ion exchange resin having a degree of cross-linking of from about 1% to about 4%, and wherein at least a portion of the dimethyl thiazolidine promoter is ionically bound to the ion exchange resin.
38 . The method of claim 29 , wherein the cross-linked, sulfonated ion exchange resin comprises a polysiloxane based ion exchange resin.
39 . The method of claim 29 , wherein the cross-linked, sulfonated ion exchange resin comprises a polysiloxane based ion exchange resin having a degree of cross-linking of from about 1% to about 4%, and wherein at least a portion of the dimethyl thiazolidine promoter is ionically bound to the ion exchange resin.
40 . The method of claim 23 , wherein the two or more reactants comprise a phenol and at least one of a ketone, an aldehyde, or a combination thereof.
41 . A method for the production of bisphenol-A, the method comprising contact a phenol and at least one of a ketone, an aldehyde, or a combination thereof in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter, wherein the method does not comprise a pretreatment and/or purification step for the phenol, ketone, and/or aldehyde.