Methods for preparing 1,1,1-tris(4-hydroxyphenyl)alkanes
View Patent ↗A method for preparing 1,1,1,-tris(4-hydroxyphenyl)alkanes generally comprises reacting a mixture of an aromatic hydroxy compound and a ketone in the presence of at least one ion exchange resin catalyst and optionally a co-catalyst to produce the 1,1,1-tris(4-hydroxyphenyl)alkanes of formula:
1. A method comprising;
reacting a mixture of an aromatic hydroxy compound and a ketone in the presence of at least one ion exchange resin catalyst to produce a 1,1,1-tris(4-hydroxyphenyl)compound of formula:
wherein the aromatic hydroxy compound has a formula of,
wherein the ketone has a formula of,
wherein R 1 and R 2 are independently at each occurrence selected from the group consisting of an aliphatic radical, a cycloaliphatic radical and an aromatic radical; “n” is an integer of value 0 to 3.
2. The method of claim 1 , wherein the mixture is reacted in the presence of the at least one ion exchange resin catalyst and a mercaptan co-catalyst.
3. The method of claim 1 , wherein the 1,1,1-tris(4-hydroxyphenyl)compound is 1,1,1-tris (4-hydroxyphenyl)ethane.
4. The method of claim 1 , wherein the aromatic hydroxy compound is phenol.
5. The method of claim 1 , wherein the ketone is 2,4, pentanedione.
6. The method of claim 1 , wherein the aromatic hydroxy compound and the ketone are at a molar ratio of 3-30:1.
7. The method of claim 1 , wherein the aromatic hydroxy compound and the ketone are at a molar ratio of 8-15:1.
8. The method of claim 1 , wherein reacting the mixture is in a batch mode.
9. The method of claim 8 , wherein the ion exchange resin catalyst is present at from 2 to 20 weight percent based on a weight of the aromatic hydroxy compound.
10. The method of claim 1 , wherein reacting the mixture is in a continuous mode.
11. The method of claim 10 , wherein the mixture of the aromatic hydroxy compound and the ketone is at a weighted hourly space velocity of about 0.2 to about 4.
12. The method of claim 2 , wherein the mercaptan co-catalyst has a formula:
wherein A is an aliphatic radical having 1 to 12 carbon atoms, a cycloaliphatic radical having 3 to 12 carbon atoms or an aromatic radical having 1 to 12 carbon atoms, B 2 is selected from the group consisting of a hydrogen, a hydroxyl, —S—H, —S—R 3 , —COOR 4 and SO 3 R 4 , B 1 is selected from the group consisting of —S—H, —S—R 3 , —SCOOR 4 and SCOR 4 , wherein R 3 is a tertiary alkyl group having 4 to 25 carbon atoms and R 4 is selected from the group consisting of a hydrogen and an aliphatic radical having 1 to 12 carbon atoms, a cycloaliphatic radical having 3 to 12 carbon atoms, an aromatic radical having 1 to 12 carbon atoms, and m is an integer having a value of 0 or 1.
13. The method of claim 1 , wherein the mercaptan co-catalyst is 3-mercaptopropanesulfonic acid.
14. The method of claim 1 , wherein the mercaptan co-catalyst is 0.01 weight percent to 5 weight percent based on a total weight of the mixture.
15. The method of claim 1 , wherein reacting the mixture comprises heating the mixture to a temperature of 30° C. to 100° C.
16. The method of claim 1 , further comprising reacting the 1,1,1-tris(4-hydroxyphenyl)compound with one or more co-monomers to form a branched polymer.
17. The method of claim 1 , further comprising purifying the 1,1,1-tris(4-hydroxyphenyl)compound by forming an adduct.
18. A method for producing 1,1,1-tris(4-hydroxyphenyl)ethane, comprising:
reacting a mixture of phenol and 2,4-pentanedione in the presence of at least one ion exchange resin catalyst and optionally a mercaptan co-catalyst to form the 1,1,1-tris(4-hydroxyphenyl)ethane.
19. The method of claim 18 , further comprising purifying 1,1,1-tris(4-hydroxyphenyl)ethane by forming an adduct with bisphenol-A, phenol or a mixture of the bisphenol-A and the phenol.