Method for producing a Bisphenol

Patent metadata

Field	Value
Publication number	US-10005709-B2
Application number	US-201715586494-A
Country	US
Kind code	B2
Filing date	May 4, 2017
Priority date	May 10, 2016
Publication date	Jun 26, 2018
Grant date	Jun 26, 2018

Abstract

In an embodiment, a method of producing a bisphenol comprises reacting a phenolic compound with a reactant comprising one or both of an aldehyde and a ketone in the presence of a catalyst system and methanol to produce the bisphenol; wherein the methanol is present in an amount of 250 to 5,000 ppm based on the total weight of the reactant; wherein the catalyst system comprises an ion-exchange resin comprising a plurality of sulfonic acid sites; and 5 to 35 mol % of an attached promoter molecule based on the total moles of the sulfonic acid sites in the catalyst system; and wherein the attached promoter molecule comprises at least two thiol groups per attached promoter molecule.

First claim

We claim:

1. A method of producing a bisphenol comprising:
reacting a phenolic compound with a reactant comprising one or both of an aldehyde and a ketone in the presence of a catalyst system and methanol to produce the bisphenol; wherein the methanol is present in an amount of 250 to 5,000 ppm based on the total weight of the reactant;
wherein the catalyst system comprises an ion-exchange resin comprising a plurality of sulfonic acid sites; and 5 to 35 mol % of an attached promoter molecule based on the total moles of the sulfonic acid sites in the catalyst system; and wherein the attached promoter molecule comprises at least two thiol groups per attached promoter molecule;
wherein an average particle size of the catalyst system is 300 to 1,500 micrometers at a moisture content of 60 to 90 wt %.

2. The method of claim 1 , wherein the catalyst system comprises 10 to 30 mol %, of the attached promoter molecule based on the total moles of the sulfonic acid sites in the catalyst system.

3. The method of claim 1 , wherein the catalyst system comprises 10 to 25 mol % of the attached promoter molecule based on the total moles of the sulfonic acid sites in the catalyst system.

4. The method of claim 1 , wherein the catalyst system comprises 10 to 20 mol % of the attached promoter molecule based on the total moles of the sulfonic acid sites in the catalyst system.

5. The method of claim 1 , wherein the catalyst system is a reaction product of a monovinylaromatic monomer and less than or equal to 4 wt % of a polyvinyl aromatic monomer based on the total amount of monomer.

6. The method of claim 5 , wherein the monovinylaromatic monomer comprises styrene.

7. The method of claim 5 , wherein the polyvinyl aromatic monomer comprises divinyl benzene.

8. The method of claim 1 , wherein the catalyst system is the polymerization product of 1.0 to 2.0 wt % of the polyvinyl aromatic monomer.

9. The method of claim 1 , wherein the catalyst system has the formula

wherein IER is a crosslinked resin, a and b are each independently an integer of 0 to 5, R n is covalently or ionically bound to the sulfonic acid site and is an amine, a pyridine, a phosphonium, or a C 1-4 group; and R 1 , R 2 , R 3 , and R 4 are each independently H, OH, SH, or an alkyl group.

10. The method of claim 1 , wherein the attached promoter molecule has the formula

wherein a and b are each independently an integer of 0 to 5, R n is an amine, a pyridine, a phosphonium, or a C 1-4 group; and R 1 , R 2 , R 3 , and R 4 are each independently H, OH, SH, or an alkyl group.

11. The method of claim 1 , wherein the attached promoter molecule comprises bis-2-(mercaptoethyl)amine.

12. The method of claim 1 , wherein the phenolic compound comprises a monocyclic phenolic compound.

13. The method of claim 12 , wherein the monocyclic phenolic compound is substituted with up to 5 substituents.

14. The method of claim 1 , wherein the phenolic compound comprises phenol, the reactant comprises acetone.

15. The method of claim 1 , wherein the catalyst system has an increased lifetime as compared to a cysteamine catalyst system comprising an attached cysteamine promoter; wherein the cysteamine catalyst system has one of a same amount of an acid site neutralization of the respective sulfonic acid sites or a same concentration of thiol groups as the catalyst system.

16. The method of claim 1 , wherein the phenolic compound comprises a polycyclic phenolic compound.

17. The method of claim 16 , wherein the polycyclic phenolic compound is substituted with up to 5 substituents.

Assignees

• Sabic Global Technologies Bv

Inventors

• Gonzalez Vidal Nathalie
• Van Goudswaard Alexander

Classifications

• C07C39/16

  Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes · CPC title

• C08J3/24

  Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K) · CPC title

• C08J2325/06

  Polystyrene · CPC title

• B01J2531/004

  Ligands · CPC title

• B01J31/00

  Catalysts comprising hydrides, coordination complexes or organic compounds (catalyst compositions used only in polymerisation reactions C08 {; catalytic antibodies C12N9/0002}) · CPC title