Alkoxylation of crude bisphenol A
View Patent ↗Crude bisphenol A containing a ketone solvent remaining form its manufacture and having a melting point of 150° C. or higher may be reacted with one or more alkylene oxide, in the absence of any added ketone solvent, at reduced temperatures compared with conventional, molten methods to give a fully alkoxylated adduct product having reduced color. By at least partially alkoxylating the bisphenol A, its potential for crystallization is disrupted and the partially alkoxylated bisphenol A has a lower melting point than the original bisphenol A permitting it to be more readily further alkoxylated at the reaction temperature. The alkoxylation reaction may be conducted at a temperature in the range of about 30 to about 140° C. Suitable catalysts may include tertiary amines or caustic compounds such as NaOH and KOH.
1. A method for producing a fully alkoxylated bisphenol A comprising:
mixing:
a compound selected from the group consisting of an alkylene oxide and an arylene oxide, with
crude bisphenol A containing a ketone solvent remaining from the manufacture of the crude bisphenol A, with
a catalyst to give a reaction mixture, where the catalyst is selected from the group consisting of:
a tertiary amine catalyst, and
a caustic compound selected from the group consisting of potassium hydroxide and sodium hydroxide,
reacting the compound with the bisphenol A in the reaction mixture at a reaction temperature in the range of about 30 to 140° C. to give an at least partially alkoxylated bisphenol A sufficiently alkoxylated to lower its melting point below the reaction temperature; and
continuing to alkoxylate the at least partially alkoxylated bisphenol A to give the fully alkoxylated bisphenol A;
where the method is conducted in the absence of added ketone solvent.
2. The method of claim 1 where the compound selected from the group consisting of alkylene oxide and arylene oxide is selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, styrene oxide and mixtures thereof.
3. The method of claim 1 where the ketone solvent is selected from the group consisting of methyl isobutyl ketone, diethyl ketone, methyl ethyl ketone, acetone, and mixtures thereof.
4. The method of claim 1 where the reaction is conducted at a pressure in the range from about 5 psig (about 0.03 MPa) to about 100 psig (0.7 MPa).
5. The method of claim 1 where the catalyst is a tertiary amine catalyst and the method is practiced in the absence of a dehydration step.
6. The method of claim 5 where the method is practiced in the absence of a neutralization step.
7. The method of claim 5 where the catalyst is selected from the group consisting of triethylamine, tributylamine, methyl alkyl amines, dimethyl alkyl amines, and mixtures thereof.
8. The method of claim 1 where the catalyst is a caustic compound and the method further comprises:
heating the reaction mixture to dehydrate it; and
neutralizing the reaction mixture.
9. A method for producing a fully alkoxylated bisphenol A comprising:
mixing crude bisphenol A containing a ketone solvent remaining from the manufacture of the crude bisphenol A, with a caustic compound catalyst to give a mixture, where the catalyst is selected from the group consisting of potassium hydroxide and sodium hydroxide;
heating the mixture to dehydrate it;
adding a compound selected from the group consisting of alkylene oxide and arylene oxide, to the mixture to give a reaction mixture;
reacting the compound with the bisphenol A in the reaction mixture at a reaction temperature in the range of about 30 to 140° C. to give an at least partially alkoxylated bisphenol A sufficiently alkoxylated to lower its melting point below the reaction temperature; and
continuing to alkoxylate the at least partially alkoxylated bisphenol A to give the fully alkoxylated bisphenol A;
where the method is conducted in the absence of added ketone solvent.
10. The method of claim 9 where the compound selected from the group consisting of alkylene oxide and arylene oxide is selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, and styrene oxide and mixtures thereof.
11. The method of claim 9 where the ketone solvent is selected from the group consisting of methyl isobutyl ketone, diethyl ketone, methyl ethyl ketone, acetone, and mixtures thereof.
12. The method of claim 9 where the reaction is conducted at a pressure in the range from about 5 psig (about 0.03 MPa) to about 100 psig (0.7 MPa).
13. A method for producing a fully alkoxylated bisphenol A comprising:
mixing crude bisphenol A containing a ketone solvent remaining from the manufacture of the crude bisphenol A, with a tertiary amine catalyst to give a mixture;
adding a compound selected from the group consisting of alkylene oxide and arylene oxide, to the mixture to give a reaction mixture;
reacting the compound with the bisphenol A in the reaction mixture at a temperature in the range of about 30 to 140° C. to give an at least partially alkoxylated bisphenol A sufficiently alkoxylated to lower its melting point below the reaction temperature; and
continuing to alkoxylate the at least partially alkoxylated bisphenol A to give the fully alkoxylated bisphenol A;
where the method is conducted in the absence of added ketone solvent.
14. The method of claim 13 where the compound selected from the group consisting of alkylene oxide and arylene oxide is selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, and styrene oxide and mixtures thereof.
15. The method of claim 13 where the ketone solvent is selected from the group consisting of methyl isobutyl ketone, diethyl ketone, methyl ethyl ketone, acetone, and mixtures thereof.
16. The method of claim 13 where the reaction is conducted at a pressure in the range from about 5 psig (about 0.03 MPa) to about 100 psig (0.7 MPa).
17. The method of claim 13 where the method is practiced in the absence of a dehydration step.
18. The method of claim 13 where the method is practiced in the absence of a neutralization step.
19. The method of claim 13 where the catalyst is selected from the group consisting of triethylamine, tributylamine, methyl alkyl amines, dimethyl alkyl amines, and mixtures thereof.