Sythesis of bisphenols

Patent metadata

Field	Value
Publication number	US-10155709-B2
Application number	US-201515325333-A
Country	US
Kind code	B2
Filing date	Jul 14, 2015
Priority date	Jul 15, 2014
Publication date	Dec 18, 2018
Grant date	Dec 18, 2018

Abstract

Various embodiments disclosed relate to methods and apparatus for synthesizing various biphenols. In various embodiments, the present invention provides a method of making a bisphenol including feeding a phenol at or proximate to the first end of a reactor column including a first end and a second end and including a solid catalyst distributed in multiple locations between the first end and the second end of the reactor column. The method includes feeding an oxomethylene compound to the reactor column at a first location that is at or proximate the first end and at one or more additional locations between the first location and the second end of the reactor column, and removing at least some water from the reactor column. The method includes removing a product composition including a diphenolmethylene product at or proximate to the second end of the reactor column.

First claim

What is claimed is:

1. A method of making a bisphenol, the method comprising:
feeding phenol at or proximate to a first end of a reactor column comprising a first end and a second end, the reactor column comprising a solid catalyst distributed in multiple locations between the first end and the second end of the reactor column, wherein the phenol is substituted or unsubstituted;
feeding oxomethylene compound to the reactor column at a first location that is at or proximate the first end and at an additional location between the first location and the second end of the reactor column, wherein the oxomethylene compound has the structure R 1 —C(O)—R 2 , wherein R 1 and R 2 are each independently —H, halide, or a substituted or unsubstituted (C 1 -C 10 )hydrocarbyl, or R 1 and R 2 together form a substituted or unsubstituted (C 1 -C 20 )hydrocarbyl ring that comprises the —C(O)— of the oxomethylene compound;
contacting the phenol and the oxomethylene compound in the reactor column in the presence of the catalyst sufficiently to condense the phenol and oxomethylene compound to give a bisphenol product and water;
removing at least some of the water from the reactor column by at least one of entraining the water in an inert gas and operating the reactor column under a vacuum; and
removing a product composition comprising the bisphenol product at or proximate to the second end of the reactor column, wherein the removing of the water is sufficient such that the product composition is about 5 wt % or less water;
wherein the reactor column has a temperature profile comprising a higher temperature at the first end and a lower temperature at the second end.

2. The method of claim 1 , wherein about 5 wt % to about 50 wt % of the product composition is the bisphenol product.

3. The method of claim 1 , further comprising purifying the product composition to provide the bisphenol product at a purity of at least about 90 wt % without subjecting the product composition to dehydration.

4. The method of claim 1 , wherein in the product composition, the concentration of the bisphenol product divided by the sum of the concentration of the bisphenol product and the concentration of all other side-products is about 50% to about 98%.

5. The method of claim 1 , wherein the method produces about 0.05 to about 5 kg of the bisphenol product per kg of the catalyst in the reactor column per hour of performance of the method.

6. The method of claim 1 , further comprising feeding the inert gas to the reactor column, wherein a feed rate of the inert gas divided by a feed rate of the phenol and the oxomethylene compound is about 0.001 L/kg to about 3 L/kg.

7. The method of claim 1 , wherein the method produces about 1 to about 50,000 kg of the bisphenol product per hour per m 3 of reactor column volume.

8. The method of claim 1 , further comprising feeding a promoter to the reactor column, wherein the phenol and the oxomethylene contact one another in the presence of the promoter.

9. The method of claim 1 , further comprising feeding the inert gas to one end of the reactor column, wherein the inert gas travels from one end of the reactor column to the other end, wherein the inert gas has a velocity from one end of the reactor column to the other end of about 0.01 cm/sec to about 30 cm/sec.

10. The method of claim 1 , wherein the inert gas is injected at or proximate to a bottom end of the reactor column, and wherein the inert gas is removed from the reactor column at or proximate to a top end of the reactor column.

11. The method of claim 1 , wherein the reactor column is operated with a weight hourly space velocity of about 0.1 h −1 to about 30 h −1 .

12. The method of claim 1 , wherein the phenol is phenol, cresol, 2-isopropylphenol, or 2-phenylphenol.

13. The method of claim 1 , wherein the phenol is an unsubstituted hydroxybenzene.

14. The method of claim 1 , wherein the oxomethylene compound is acetone, acetophenone, hexafluoroacetone, butanone, benzophenone, acetaldehyde, formaldehyde, substituted or unsubstituted cyclohexanone, or 3,3,5-trimethylcyclohexanone.

15. The method of claim 1 , wherein the oxomethylene compound is acetone.

16. The method of claim 1 , wherein the bisphenol is at least one selected from the group consisting of: bisphenol A (2,2-bis(4-hydroxyphenyl)propane), bisphenol AP (1,1-bis(4-hydroxyphenyl)-1-phenyl-ethane), bisphenol AF (2,2-bis(4-hydroxyphenyl)hexafluoropropane), bisphenol B (2,2-bis(4-hydroxyphenyl)butane), bisphenol BP (bis-(4-hydroxyphenyl) diphenylmethane), bisphenol C (2,2-bis(3-methyl-4-hydroxyphenyl)propane), bisphenol E (1,1-Bis(4-hydroxyphenyl)ethane), bisphenol F (bis(4-hydroxydiphenyl)methane), bisphenol G (2,2-bis(4-hydroxy-3-isopropyl-phenyl)propane), bisphenol PH (5,5′-(1-methylethyliden)-bis[1,1′-(bisphenyl)-2-ol]propane), bisphenol TMC (1,1-bis(4-hydroyphenyl)-3,3,5-trimethyl-cyclohexane), and bisphenol Z (1,1-bis(4-hydroxyphenyl)-cyclohexane).

17. The method of claim 1 , wherein the bisphenol is bisphenol A (4,4′-(propane-2,2-diyl)diphenol).

18. The method of claim 1 ,
wherein the first end is a top end of a reactor column and the second end is a bottom end,
wherein the reactor column has a holdup of the catalyst of about 20 vol % to about 60 vol %;
wherein the oxomethylene compound comprises acetone which is fed to the reactor column at a first location that is at or proximate the top end and at an additional location between the first location and the bottom end of the reactor column, wherein the reactor column is operated with a weight hourly space velocity of about 5 h −1 to about 20 h −1 ;
wherein the bisphenol product is bisphenol A (4,4′-(propane-2,2-diyl)diphenol);
wherein the water is removed from the reactor column by at least one of entraining the water in an inert gas injected at or proximate the bottom end of the reactor column and removed from the reactor column at or proximate to the top end of the reactor column, wherein a feed rate of the inert gas divided by the feed rate of the phenol and the acetone is about 0.01 L/kg to about 0.55 L/kg, wherein the removing of the water is sufficient such that the product composition is about 2 wt % or less water; and
wherein the product composition comprising the bisphenol A is removed at or proximate to the bottom end, wherein about 8 wt % to about 35 wt % of the product composition is the bisphenol A, and in the product composition the concentration ratio of the bisphenol A divided by sum of the concentration of the bisphenol A and the concentration of all other side-products is about 70% to about 95%;
wherein the method produces about 0.1 to about 2 kg of the bisphenol A per kg of the catalyst in the reactor column per hour of performance of the method, and about 10 to about 1,000 kg of the bisphenol A per hour per m 3 of reactor column volume.

Assignees

• Sabic Global Technologies Bv

Inventors

• Manchekar Arun Vasant
• Anapat Samir
• Oyevaar Martin

Classifications

• C07C37/20 Primary

  using aldehydes or ketones · CPC title

• Y02P20/127

  Cross-Sectional Technologies · mapped topic

• C07C39/16 Primary

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

• B01D3/009 Primary

  in combination with chemical reactions · CPC title

• C07C37/68

  Purification; separation; Use of additives, e.g. for stabilisation {(C07C37/004 and C07C37/005 take precedence)} · CPC title