# US 9,040,724 B2 · Diaryl sulfone compound, and manufacturing method for same

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- Number: US 9,040,724 B2
- Document ID: US9040724B2
- Status: Granted
- Kind: B2
- Application number: 13/583,725
- Filed: 2011-03-09
- Published: 2013-01-03
- Granted: 2015-05-26
- Earliest claimed: 2010-03-18
- Assignees: Sumitomo Seika Chemicals Co., Ltd.
- Applicants: Paul Kuad; Hisaaki Kanda; Takeshi Fujiwara; Hiroyuki Shiraishi
- Inventors: Paul Kuad; Hisaaki Kanda; Takeshi Fujiwara; Hiroyuki Shiraishi
- Web page: https://patentgrep.com/patent/US9040724B2

## CPC

- C07C 323/65: containing sulfur atoms of sulfone or sulfoxide groups bound to the carbon skeleton
- C07C 319/06: from sulfides, hydropolysulfides or polysulfides
- C07C 327/06: to hydrogen atoms or to carbon atoms of an acyclic saturated carbon skeleton
- C07D 331/02: Three-membered rings
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention provides a diaryl sulfone compound represented by Formula (1) below: wherein R1 to R4 and R1′ to R4′ are the same or different; each represents hydrogen, C1-4 alkyl, or halogen; and R5 is (thio)glycidyl, acryloyl, or the like; and a method for producing the same. According to the present invention, a novel compound useful as a monomer for producing synthetic resin having a high refractive index and excellent transparency for optical materials can be efficiently produced with a simple production process, using an inexpensive material as a starting material.

## Claims

### Claim 1

A diaryl sulfone compound represented by Formula (1):
wherein R1 to R4 and R1′ to R4′ are the same or different, and each represents hydrogen, C1-4 alkyl, or halogen; and R5 is a group represented by the following formula:
wherein R6 represents C1-4 alkylene, and A represents oxygen or sulfur;
or a group represented by the following formula:
wherein R7 represents C2-5 alkenyl.

### Claim 2 (depends on 1)

The diaryl sulfone compound according to claim 1, represented by Formula (1-1):
wherein R1 to R4 and R1′ to R4′ are the same or different, and each represents hydrogen, C1-4 alkyl or halogen; R6 represents C1-4 alkylene; and A represents oxygen or sulfur.

### Claim 3 (depends on 1)

The diaryl sulfone compound according to claim 1, represented by Formula (1-2):
wherein R1 to R4 and R1′ to R4′ are the same or different, and each represents hydrogen, C1-4 alkyl or halogen; and R7 represents C2-5 alkenyl.

### Claim 4 (depends on 1)

The diaryl sulfone compound according to claim 1, wherein R1 to R4 and R1′ to R4′ are all hydrogen.

### Claim 5

A method for producing a diaryl sulfone compound represented by Formula (1-1-a):
wherein R1 to R4 and R1′ to R4′ are the same or different, and each represents hydrogen, C1-4 alkyl or halogen; and R6 is C1-4 alkylene;
the method comprising reacting a 4,4′-dimercaptodiaryl sulfone compound represented by Formula (2):
wherein R1 to R4, R1′ to R4′, and R6 are as defined above;
with a halide represented by Formula (3):
wherein R6 is as defined above and X is halogen;
in a solvent in the presence of at least one catalyst selected from the group consisting of lithium chloride and lithium bromide to produce a compound represented by Formula (4):
wherein R1 to R4, R1′ to R4′, R6, and X are as defined above; and reacting the resulting compound with a base to perform a dehydrohalogenation reaction.

### Claim 6

A method for producing diaryl sulfone compound represented by Formula (1-1-b):
wherein R1 to R4 and R1′ to R4′ are the same or different, and each represents hydrogen, C1-4 alkyl, or halogen; and R6 represents C1-4 alkylene;
the method comprising reacting a compound represented by Formula (1-1-a):
wherein R1 to R4, R1′ to R4′, and R6 are as defined above;
with at least one compound selected from the group consisting of thiourea and thiocyanates, in an organic solvent.

### Claim 7

A method for producing a diaryl sulfone compound represented by Formula (1-2):
wherein R1 to R4 and R1′ to R4′ are the same or different, and each represents hydrogen, C1-4 alkyl, or halogen; and R7 represents C2-5 alkenyl;
the method comprising reacting a salt of 4,4′-dimercaptodiaryl sulfone represented by Formula (2-1):
wherein R1 to R4, R1′ to R4′, and R7 are as defined above; and M represents a cation moiety of a base;
with a halide represented by Formula (5):
wherein R7 is as defined above, and X represents halogen.

### Claim 8

A method for producing a dimercaptodiaryl sulfone compound represented by Formula (2):
wherein R1 to R4 and R1′ to R4′ are the same or different, and each represents hydrogen, C1-4 alkyl, or halogen;
the method comprising reacting a dimethylthiodiaryl sulfone compound represented by Formula (6):
wherein R1 to R4 and R1′ to R4′ are as defined above;
with at least one halogenating agent selected from the group consisting of chlorine, sulfuryl chloride, phosphorus pentachloride, phosphorous trichloride, hypochlorous acid and bromine to obtain a diaryl sulfone compound represented by Formula (7):
wherein R1 to R4 and R1′ to R4′ are as defined above; X represents halogen; and m and n each represents an integer of 1 to 3; and subjecting the resulting compound to hydrolysis.

### Claim 9 (depends on 2)

The diaryl sulfone compound according to claim 2, wherein R1 to R4 and R1′ to R4′ are all hydrogen.

### Claim 10 (depends on 3)

The diaryl sulfone compound according to claim 3, wherein R1 to R4 and R1′ to R4′ are all hydrogen.