CA1191160A

CA1191160A - Process in the production of bis(4-hydroxyphenyl) biphenyl disulfone

Info

Publication number: CA1191160A
Application number: CA000427081A
Authority: CA
Inventors: Sivaram Krishnan; John R. Sanderson
Original assignee: Mobay Corp
Current assignee: Bayer Corp
Priority date: 1982-06-01
Filing date: 1983-04-29
Publication date: 1985-07-30
Also published as: DE3318355A1

Abstract

A PROCESS IN THE PRODUCTION OF
BIS(4-HYDROXYPHENYL)BIPHENYL DISULFONE
ABSTRACT OF THE DISCLOSURE

The present invention relates to a process for the production of bis(4-hydroxyphenyl)biphenyl disulfone.

Description

Mo -23~2 ~ PROCESS IN rrHE PRODUCTION OF
BIS (4-l[YDROXYPllE'N~L) BIPHENYI, D:CSULFONE
BACKGROIJND OF TEIE IMVENTION
Bis(4-hydroxyphenyl)biphenyl disulfone has been found to be a useful monomer in preparing polymers such as polyure-thanes, polycarbonates, polyethers, polyesters and polysulfones. Polycarbonates prepared using such a monomer are disclosed in U.S. Patent 3,2~9,986. Such polymers are generally useful in films, fibers, injection molded parts, extruded tubes and molded parts, blow molded articles and coatings.
The object of the present invention is to provide a novel process for the preparation of bis(4-hydroxyphenyl) biphenyl disulfone.
SUMMARY OE'_~IE INVENTION
The present invention pertains to a process for the preparation of bis(4-hydroxyphenyl)biphenyl disulfone com-prising reacting 4,4'-dibromobiphenyl with 4-mercapto-phenol to produce bis(4-hydroxyphenyl)bi.phenyl disulfide and oxidizing the bis(4-hydroxyphenyl)biphenyl disulfide to produce bis(4-hydroxyphenyl)biphenyl disulfone; in a preferred embodi.ment said oxidizing is carried out using hydrogen peroxide and acetic acid.
DETAILED DESCRIPTION OF THE INVENTION
The process of the invention Eor the preparation of bis(4-hydroxyphenyl)biphenyl disul-fone may be illustrated by the following general reaction scheme:
Br ~ Br +HS ~ OH diKetchOylfohrmat ide ,~Ho ~ S ~ ~ S ~ OH

HO ~ S02 ~ S02 ~ OH ~- acetic acid,heat As indicated above, 4,4'-dibromobiphenyl is reacted with 4-mercaptophenol in the presence of dimethylformamide Mo-2382 .

and potasslum carbonate to produce 1.7is (~~hydrOX~pherlyL) b:iphe~yL clisul~ide which in turn is reacted in the prescn~e of hyc1ro~en peroxide and acetic acid to produce the bis(4-hydroxyphenyl) biphenyl disulfone. The resulting monomer 5 is generally recovered as a precipitate and is then separ-ated and dried.
The process of the invention is advantageous in that it produces high purity (99.9-~ %) bis(4-hydroxyphenyl) biphenyl disulforle in high yields ~80% and higher).
The invention will be further illustrated, but is not intended to be limited, by the following example.
EXAMPLE
Preparation of bis(4-hydroxyphenyl)biphenyl disulfide (HPSB) .
Potassium carbonate (75.9 g, 0.55 mol) was charged 15 to a 2 liter flask equipped with a stirrer, condenser, dropping funnel, thermometer and nitrogen purge. Dimeth~l-formamide (200 ml) was added and the solution heated to 80-90C. 4-mercaptophenol (69.3 g, 0.55 mol) in 200 ml of dimethylformamide was added to the stirrer reaction 20 mixture over one hour. ~he reaction mixture was maintained at 100-110C for two hours. Solid 4,4'-dibromobiphenyl (78 g, 0.25 mol) was then added over one hour. The reaction mixture was refluxed for 18 hours, cooled to room temperature, and poured into 10% HCl. The white to 25 yellow solid was collected with suction and washed with water. The solid was treated with 5-10% NaOH and fil-tered once more with suction. The mother liquor was acidified to pH~2, and the solid collected and recry-stallized from chlorobenæene/methanol. A 34% yield of 30 pure HPSB was obtained with a melting point of 214~217C.
Calculated analysis of C24H18O2S2:
C, 71.64; H, 4.47; S, 15.92.
Found- C, 71.76; H, 4.61; S, 15.73.

Mo-2382 ~3~

-3~
Preparation oE his(4-hyclroxyphenyL)hiphenyLdisulfone (IIBD) from bis(4-hydroxyphenyl)biphenyl disulflde (IIPSB) _ ~
TIPSB (~0.2 g, 0.10 mol) ancl 250 ml of glacial acetic acid were placed in a liter flask equipped with a stirrer, 5 thermometer, dropping funnel and heating mantle. The reaction mixture was heated to 70-75C and (113 g, 1.0 mol) 30~ hydrogen peroxide was added over 2 hours. The reaction mixture was heated for an additional 4 hours at 70-75~C and 250 ml water were added. The light ye]low 10 solid was collected with suction and washed with water.
After drying 4~.2 g, (91% yield) pure bis(4-hydroxyphenyl) biphenyl disulfone was obtained having a melting point of 236-240C.
Although the invention has been described in detail 15 in the foregoing for the purpose of illustration, it is to be understood that such detail is solely for that purpose and that variations can be made therein by those skilled in the art without departing from the spirit and scope of the invention except as it may be limited by the 20 claims.

Mo-2382

Claims

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. A process for the preparation of bis(4-hydroxy-phenyl)biphenyl disulfone comprising reacting 4,4'-di-bromobiphenyl with 4-mercaptophenol to produce bis(4-hydroxyphenyl)biphenyl disulfide and oxidizing said bis(4-hydroxyphenyl)biphenyl disulfide to bis(4-hydroxyphenyl) biphenyl disulfone.

2. The process of Claim 1 wherein said 4,4'-dibromo-biphenyl is reacted with 4-mercaptophenol in the presence of dimethylformamide and potassium carbonate.

3. The process of Claim 1 wherein said bis(4-hydroxyphenyl)biphenyl disulfide is oxidized to bis(4-hydroxyphenyl)-biphenyl disulfone in the presence of hydrogen peroxide and acetic acid.