New cycloadduct precursors of dihalodiphenylsulfones and preparations thereof

Patent metadata

Field	Value
Publication number	US-2020190102-A1
Application number	US-201816636466-A
Country	US
Kind code	A1
Filing date	Aug 6, 2018
Priority date	Aug 7, 2017
Publication date	Jun 18, 2020
Grant date	—

Abstract

The invention relates to new compounds of formula (I) wherein X represents a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine, which are useful for the preparation of 4,4′dihalodiphenylsulfones of formula (III) wherein X is as defined above.

First claim

1 . A compound of formula (I)

wherein X represents a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine.

2 . The compound according to claim 1 , wherein the halogen atom is chlorine or bromine, preferably chlorine.

3 . A process for the preparation of a compound of formula (I) according to claim 1 , comprising reacting divinylsulfone with a halofuran of formula (II)

wherein X represents a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine,
and optionally further isolating the compound of formula (I).

4 . The process according to claim 3 , wherein the halofuran is 3-chlorofuran or 3-bromofuran.

5 . The process according to claim 3 , wherein the molar ratio of the halofuran of formula (II) to divinylsulfone is of at least 2/1.

6 . (canceled)

7 . A process for the preparation of a 4,4′-dihalodiphenylsulfone of formula (III)

wherein X represents a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine,
the process comprising carrying out the dehydration/aromatization of a compound of formula (I)

wherein X is as defined above.

8 . The process according to claim 7 , wherein the dehydration/aromatization is carried out in the presence of an alkali hydroxide.

9 . The process according to claim 7 , wherein the dehydration/aromatization is carried out in the presence of DMSO.

10 . A process for the preparation of a 4,4′-dihalodiphenylsulfone of formula (III)

wherein X represents a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine,
the process comprising:
a) providing a compound of formula (I)

wherein X is as defined above,
b) carrying out the dehydration/aromatization of said compound of formula (I),
c) optionally further isolating compound of formula (III).

11 . The process according to claim 10 , wherein compound of formula (I) is prepared by reacting divinylsulfone with a halofuran of formula (II)

wherein X is as defined above.

12 . (canceled)

13 . A process for the manufacture of a polyarylethersulfone comprising the steps of:
i) preparing a 4,4′-dihalodiphenylsulfone of formula (III)

wherein X represents a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine,
by the process according to claim 7 ,
ii) optionally, isolating the 4,4′-dihalodiphenylsulfone,
iii) forming a reaction mixture comprising the 4,4′-dihalodiphenylsulfone and at least one of M 1 and M 2 , wherein M 1 is at least one dibasic salt of a dihydroxy aromatic compound and M 2 consists of at least one dihydroxy aromatic compound and at least one basic compound,
iv) carrying out a polycondensation reaction of the reaction mixture.

14 . A process for the manufacture of 4,4′-diaminodiphenylsulfone comprising the steps of:
i) preparing a 4,4′-dihalodiphenylsulfone of formula (III)

wherein X represents a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine,
by the process according to claim 7 ,
ii) optionally, isolating the 4,4′-dihalodiphenylsulfone,
iii) carrying out an amination reaction of the 4,4′-dihalodiphenylsulfone with an aminating agent.

15 . The process according to claim 13 , wherein the process comprises the step ii) of isolating the 4,4′-dihalodiphenylsulfone.

16 . The compound according to claim 2 , wherein the halogen atom is chlorine.

17 . The process according to claim 8 , wherein the alkali hydroxide is sodium hydroxide or potassium hydroxide.

18 . The process according to claim 14 , wherein the aminating agent is ammonia.

19 . A process for forming a shaped article, the process comprising solution processing or melt processing the polyarylethersulfone manufactured by the process according to claim 13 .

20 . A shaped article formed by the process according to claim 19 .

Assignees

• Rhodia Operations

Inventors

• Muller Eric

Classifications

• C07D493/08 Primary

  Bridged systems · CPC title

• C07C317/14

  having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C315/04

  by reactions not involving the formation of sulfone or sulfoxide groups · CPC title