5397-34-2

Usage

Uses

Used in Thermal Printing Industry:
2,4'-DIHYDROXYDIPHENYL SULFONE is used as a key component in the production of thermal printing papers. It is utilized for its ability to form colorless leuco dyes that can be developed into a visible image upon exposure to heat. This property makes it an essential material in the manufacturing of thermal printers and their consumables.
Used in Dye Development:
In the dye industry, 2,4'-DIHYDROXYDIPHENYL SULFONE is used as a starting material for the synthesis of black leuco dyes. These dyes are important for various applications, including the production of color films, photographic materials, and other imaging technologies. 2,4'-DIHYDROXYDIPHENYL SULFONE's chemical structure allows for the development of dyes with high color strength and stability, making it a valuable resource in the dye industry.
Used in Polymer Synthesis:
2,4'-DIHYDROXYDIPHENYL SULFONE is also utilized as a monomer in the synthesis of various polymers, such as polyethersulfone (PES) and polyphenylene sulfide (PPS). These polymers are known for their high thermal stability, mechanical strength, and chemical resistance, making them suitable for use in the electronics, automotive, and aerospace industries.
Used in Pharmaceutical Industry:
Due to its chemical properties, 2,4'-DIHYDROXYDIPHENYL SULFONE can be used as an intermediate in the synthesis of various pharmaceutical compounds. Its ability to form stable derivatives with other molecules makes it a valuable building block for the development of new drugs and therapeutic agents.

InChI:InChI=1/C12H10O4S/c13-9-5-7-10(8-6-9)17(15,16)12-4-2-1-3-11(12)14/h1-8,13-14H

Synthetic route

phenol (108-95-2) → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
Stage #1: phenol With sulfuric acid; benzene-1,3-disulfonic acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5h; Heating / reflux; Stage #2: at 170 - 185℃; under 525.053 Torr; for 2h; Product distribution / selectivity;	A 94% B n/a
With sulfuric acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5h; Product distribution / selectivity; Heating / reflux;	A 89% B n/a
Stage #1: phenol With sulfuric acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5h; Heating / reflux; Stage #2: at 170 - 185℃; under 525.053 Torr; for 2h; Product distribution / selectivity;	A 83% B n/a

1-chloro-2-(4-chlorophenylsulfonyl)benzene (38980-51-7) → 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
With potassium hydroxide at 160 - 165℃;
With potassium hydroxide at 160 - 165℃;

1-methoxy-2-((4-methoxyphenyl)sulfonyl)benzene (24197-29-3) → 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
With aluminium trichloride; xylene

sulfuric acid (7664-93-9) + phenol (108-95-2) → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
at 165 - 200℃;

sulfuric acid (7664-93-9) + sulfur trioxide (7446-11-9) + phenol (108-95-2) → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
at 180 - 190℃;

4-Methoxybenzenethiol (696-63-9) → 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: copper-powder / 235 - 240 °C 2: KMnO4; glacial acetic acid / Erwaermen auf dem Dampfbad 3: AlCl3; xylene View Scheme

monosodium salt of 2,4'-dihydroxydiphenylsulfone (202924-57-0) → 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
With sulfuric acid In water
With sulfuric acid In methanol

fluorosulphonic acid (HFSO3) + phenol (108-95-2) → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
With hydrogen fluoride

4,4'-dichlorodiphenyl sulphone (80-07-9) + 1-chloro-2-(4-chlorophenylsulfonyl)benzene (38980-51-7) → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
With water; sodium hydroxide at 220℃; for 4h;

chlorobenzene (108-90-7) → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
Stage #1: chlorobenzene With sulfur trioxide; dimethyl sulfate at 30℃; for 2h; Stage #2: With sodium hydroxide In water at 220℃; for 4h;

trifluoromethylsulfonic anhydride (358-23-6) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2) → 2,4'-bis(trifluoromethylsulfonyloxy)diphenylsulfone (1228364-92-8)

Conditions	Yield
Stage #1: 2,4'-dihydroxydiphenyl sulfone With pyridine In dichloromethane at -78℃; for 0.166667h; Inert atmosphere; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at -78 - 0℃; Inert atmosphere;	81%

2,4'-dihydroxydiphenyl sulfone (5397-34-2) → (2-benzoyloxy-phenyl)-(4-benzoyloxy-phenyl)-sulfone

2,4'-dihydroxydiphenyl sulfone (5397-34-2) + acetyl chloride (75-36-5) → (2-acetoxy-phenyl)-(4-acetoxy-phenyl)-sulfone (57154-52-6)

Conditions	Yield
With acetic acid

2,4'-dihydroxydiphenyl sulfone (5397-34-2) + dimethyl sulfate (77-78-1) → 1-methoxy-2-((4-methoxyphenyl)sulfonyl)benzene (24197-29-3)

Conditions	Yield
With alkaline solution

N,N-bis-(2-chloroethyl)carbamoyl chloride (2998-56-3) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2) → 2,4'-Bisdiphenylsulfon (6526-89-2)

Conditions	Yield
With pyridine

Upstream product

• 38980-51-7 1-chloro-2-(4-chlorophenylsulfonyl)benzene 
• 24197-29-3 1-methoxy-2-((4-methoxyphenyl)sulfonyl)benzene 
• 7664-93-9 sulfuric acid 
• 108-95-2 phenol 
• 7446-11-9 sulfur trioxide 
• 696-63-9 4-Methoxybenzenethiol 
• 696-62-8 para-iodoanisole 
• 80-07-9 4,4'-dichlorodiphenyl sulphone 
• 108-90-7 chlorobenzene 
• 202924-57-0 monosodium salt of 2,4'-dihydroxydiphenylsulfone 
• 14065-23-7 1-methoxy-2-[(4-methoxyphenyl)thio]benzene 
• 7217-59-6 2-Methoxybenzenethiol 
• 529-28-2 4-iodoanisol 

Downstream Products

• 57154-52-6 (2-acetoxy-phenyl)-(4-acetoxy-phenyl)-sulfone 
• 24197-29-3 1-methoxy-2-((4-methoxyphenyl)sulfonyl)benzene 
• 6526-89-2 2,4'-Bisdiphenylsulfon 

Relevant academic research and scientific papers

Separation of 2,4′- and 4,4′-dihydroxydiphenyl sulfones

To develop a procedure for separating 2,4′- and 4,4′- dihydroxydiphenyl sulfones, their acidity and solubility in water were studied. Pleiades Publishing, Inc., 2006.

Thermal recording material

A thermal recording material having both of excellent coloring property and storage stability with a low cost is provided. The thermal recording material contains a leuco dye and a developer in a coloring layer, and the developer contains 2,4′-dihydroxydiphenylsulfone and 4,4′-dihydroxydiphenylsulfone with a specific ratio, and the above-mentioned two kinds of the dihydroxydiphenylsulfones are made a material obtained by sequentially undergoing a separating step for heightening the weight ratio of a 2,4′ material from a dichlorodiphenylsulfone mixture containing the 2,4′ material and a 4,4′ material, a reaction step of hydrolyzing the mixture to obtain a dihydroxydiphenylsulfone mixture, and a post-treatment step of subjecting to decolorization and purification.

Liquid-crystal aromatic polyesters containing azo and sulfone units

Two novel aromatic polyesters containing azo and sulfone units were synthesized by poly-condensation of 4,4′-azobenzene-dicarbonyl chloride with dihydroxydiphenyl sulfones at low temperature. The synthesized polymers exhibited good solubility, inherent viscosity (reaches 1.05 dL g-1), high glass transition temperature (above 200 °C) and thermal stability (≤ 5 % weight loss at 348 °C), which were characterized by Fourier transform infrared spectroscopy. The liquid crystalline and photoisomerization properties were observed by polarizing optical microscope and an ultraviolet-visible spectrophotometer.

PROCESS FOR THE PRODUCTION OF A SULFONE MONOMER

The present invention provides an economic and environmentally friendly method for the preparation of polymer grade 4,4'-dichlorodiphenyl sulfone which is substantially free of 2,4' and 3,4'-isomers of dichlorodiphenyl sulfone with yield of over 90%, with substantially reduced reaction times without the use of impregnated catalysts. Further no toxic byproducts such as dimethyl pyrosulfate are formed thereby reducing the load on effluent treatment with the added advantage of substantially recycling the reactants and byproducts. Further the present invention discloses a process is disclosed in which isomeric mixture of 4,4'-, 3,4'-, and 2,4'-dichlorodiphenyl sulfone produced during the preparation of 4,4'-dichlorodiphenyl sulfone is converted to value added products such as diphenyl sulfone, 2,4'- dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenyl sulfone and 2-aminodiphenyl sulfone.

COLOR DEVELOPING COMPOSITION CONTAINING MOLECULAR COMPOUND, AND RECORDING MATERIAL

Provided is a color-developing composition containing a molecular compound which has as a component compound a compound represented by formula (I) [wherein Y represents a C1-C12 hydrocarbon group which is chained or branched and saturated or unsaturated, or a C1-C8 hydrocarbon group which is chained or branched, saturated or unsaturated and has an ether or thioether bond; R1, R2, R3 and R4 each independently represent a C1-C6 alkyl group or C2-C6 alkenyl group; n, p, q and r each represents any integer of 0 to 4; and m represents any integer of 0 to 2]. Also provided is a recording material with a sufficient color-forming sensitivity, superior storage stability, and especially with an extremely little background fogging in a heat resistance test.

Process for producing high-purity 4,4'-dihydroxydiphenyl sulfone

The present invention provides a process for producing 4,4′-dihydroxydiphenylsulfone of very high purity. In particular, the present invention provides a process for producing 4,4′-dihydroxydiphenylsulfone of high purity comprising the steps of subjecting phenol in combination with a sulfonating agent or phenolsulfonic acid to a dehydration reaction in the presence of an aromatic nonpolar solvent while suspending the resulting dihydroxydiphenylsulfone therein, mixing the reaction suspension with a polar solvent to at least partially dissolve the dihydroxydiphenylsulfone, and precipitating 4,4′-dihydroxydiphenylsulfone.

PROCESS FOR PRODUCING 4,4-BISPHENOL SULFONE

A process for producing 4,4'-bisphenol sulfone by reacting phenol with sulfuric acid, which includes conducting a dehydration reaction in a mixed solvent including an aliphatic saturated hydrocarbon having a boiling point of 175°C or higher and mesitylene, and finally distilling off the mesitylene from the reaction system, or includes conducting the reaction in a solvent including an aliphatic saturated hydrocarbon in a reaction vessel equipped with a fractionating device. Thus, 4,4'-bisphenol sulfone can be produced in high yield with a high operating efficiency. Also, provided is a process for easily producing 4,4'-bisphenol sulfone having a high purity which includes conducting the reaction in a solvent containing an aliphatic saturated hydrocarbon, subsequently adding a C1-3 alcohol to the reaction mixture, separating an alcohol layer, and recrystallizing the 4,4'-bisphenol sulfone from the alcohol layer.

PROCESS FOR PRODUCING 2,4'-DIHYDROXYDIPHENYL SULFONE

A process for producing 2,4'-dihydroxydiphenylsulfone which comprises separating 4,4'-dihydroxydiphenylsulfone by crystallization from a mixture containing 4,4'-dihydroxydiphenylsulfone, 2,4'-dihydroxydiphenylsulfone, phenolsulfonic acid and phenol which is obtained by dehydration of phenol and sulfuric acid or phenolsulfonic acid to obtain a mixture having a content of 2,4'-dihydroxydiphenylsulfone greater than the content of 4,4'-dihydroxydiphenylsulfone, crystallizing 2,4'-dihydroxydiphenylsulfone by adjusting the composition of the solvent of the obtained mixture so that the ratio of the amounts by weight of phenol to water is 10:90 to 90:10, and separating 2,4'-dihydroxydiphenylsulfone by filtration; and a process as described above in which the filtrate obtained by the filtration is used as the raw material for the hydration.

PROCESS FOR PRODUCING MIXTURE OF DIHYDROXYDIPHENYLSULFONE ISOMERS

The present invention provides a process for producing a mixture of dihydroxydiphenylsulfone isomers containing 2,4'-dihydroxydiphenylsulfone, the process comprising heating 4,4'-dihydroxydiphenylsulfone or a mixture of dihydroxydiphenylsulfone isomers containing at least 85 wt.% of 4,4'-dihydroxydiphenylsulfone in the presence of phenol and sulfuric or sulfonic acid.

PROCESS FOR PRODUCING MIXTURE OF DIHYDROXYDIPHENYLSULFONE ISOMERS

The present invention provides a process for producing a mixture of 4,4'- and 2,4'-dihydroxydiphenylsulfones comprising heating trihydroxytriphenyldisulfone or a mixture of dihydroxydiphenylsulfone isomers containing trihydroxytriphenyldisulfone in the presence of phenol and an acid catalyst.