Bis- 4-hydroxyphenyl -sulfone

Bis-(4-hydroxyphenyl) sulfone is also addressed as 4,4 -dihydroxydiphenyl sulfone, or 4,4 -bisphenol S. It is of great conunereial interest for the preparation of PES. It can be prepared by reacting phenol with sulfurie acid, without using a solvent. Sueh proeesses give a erude product with 60-70% bis-(4-hydroxyphenyl)-sulfone. 

In addition, the crude produet contains 20-30% of the isomer 2,4-di-hydroxydiphenyl sulfone and ea. 10% of 6-hydroxy[l,3-bis-(4-hydroxy-phenylsulfonyl]benzene. 

A major effort is required to isolate the desired bis-(4-hydroxyphen-yl)-sulfone in high purity from the mixture. Yield and selectivity of the reaction can be improved by using a solvent. Purification is simplified, when the bis-(4-hydrox q)henyl)-sulfone formed is selectively deposited on a nucleating surface, i.e., a supercooled surface, during or after the reaction, and thus removed from the reaction medium.  

Suitable solvents are either excess phenol or an inert aromatic solvent. Preferred solvents are those in which the 2,4 -isomer is more highly soluble than the bis-(4-hydroxyphenyl)-sulfone, such as chlorobenzene, dichlorobenzene and trichlorobenzene. 

In a semi-continuous process, in the first step phenol is extensively reacted with sulfuric acid to give phenolsulfonic acid. Any water of reaction thereby formed is removed by distillation. Then, the phenolsulfonic acid is reacted with phenol to give bis-(4-hydroxyphenyl)-sulfone and the water of reaction formed is again removed by distillation.  

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Aluminium tetrahydroborate, Alkenes, Oxygen Benzeneseleninic acid, Hydrazine derivatives Benzyltriethylammonium permanganate Bis(4-hydroxyphenyl) sulfone... 

Aluminium chloride, Nitrobenzene, 0062 Ammonium hydrogen sulfite, 4545 Benzyltriethylammonium permanganate, 3617 Bis(4-hydroxyphenyl) sulfone, 3497 2-Chloro-5-nitrobenzenesulfonic acid, 2144 1,3 -Dichloro-5,5-dimethyl-2,4-imidazolidindione, 1865 f Dimethyl sulfoxide, 0921... 

Bis(4-hydroxyphenyl)-sulfone(,ca.lled Sulfonyldi-pbenol in CA 5th Decennial Formula Index)[cal-led Bis(4-oxy-phenyl)-sulfon 4.4 -Dioxy-diphenyl-sulfon or 4.4 -Dioxy-sulfobenzid in Ger], H0.C6Ha.S02.C6H4.0H mw 252.29, O 25.37% ndls(from w), mp 238-239° forms salts other props and methods of prepn are given in Beil 6,... 

Sulfonyl-bis(2,6-dinitrophenol) in CA 5th Decennial Formula Index] [called Bis(3.5-dinitro -4-oxy-phenyl)-sulfon or 3.5.3 .5 -Tetranitro-4.4 -dioxy-diphenylsulfon in Ger], 0aS[(02N)2C6H2.0H]2 mw 430.27, N 13.02% very bitter-tasting straw-yel ndlsffrom boiling w), mp 257-258°(Ref 4) insol in most org solvs can be prepd by nitrating either bis(3-nitro-4-hydroxy-phenyl)-sulfone or bis(4-hydroxyphenyl)-sulfone and by hydrolyzing bis(3,5-dinitro-4-chlorophenyl) -sulfone(Refs 1 2). It forms salts which can be used in ignition compositions(Ref 3)... 

Pyrolysis in the presence of tetramethylammonium hydroxide (TMAH) at a lower temperature of 300° C was studied for both PES and PSF [11]. In this study, the main component for the thermally assisted hydrolysis and methylation of PES was dimethyl derivative of bis(4-hydroxyphenyl)sulfone. This compound was formed through selective cleavages of ether linkages maintaining intact the sulfone structures. For PSF thermally assisted hydrolysis and methylation at 300° C, the main constituents were dimethyl derivative of bis(4-hydroxyphenyl)isopropylidene (bisphenol A) and also dimethyl derivative of bis(4-hydroxyphenyl)sulfone. A partial decomposition of the sulfone groups in PSF during the THM reaction also was noted. The findings also were confirmed by matrix assisted laser desorption mass spectrometric measurements. 

The copolymerization of 5-[(4-fluorophenyl)sulfonyl]-2-fiuorobenz-oic acid with bis-(4-hydroxyphenyl)-sulfone results in carboxylated PES. However, during polycondensation, partial decarboxylation occurs. The copolymerization of 2,5-dihydroxybenzoic acid with bis-(4-fluorophenyl)-sulfone results in a PES with quantitative decarboxylation. ... 

The momomers can be chain extended with bis-(4-fluorophenyl)sulf-one or bis-(4-hydroxyphenyl)-sulfone, respectively in a next condensation step. Eventually, in a final condensation step, block copolymers containing blocks of unsulfonated aromatic polyether sulfones and blocks of aromatic polyether sulfones sulfonated on the aromatic rings are obtained. The block copolymers provide compounds with both an adjustable degree of sulfonation and a defined length of sulfonated and unsulfonated blocks. The materials are suitable for the preparation of synthetic membranes. 

M. Stumpp, R Neumann, W. Ruehenback, and M. Bergner. Preparation of bis(4-hydroxyphenyl)sulfone. US Patent 5059715, assigned to BASF Aktiengesellschaft (Ludwigshafen, DE), October 22, 1991. 

Bis (4-hydroxyphenyl) sulfone Bis (p-hydroxyphenyl) sulfone. See 4,4 -Dihydroxydiphenyl sulfone... 

Dihydroxydiphenyldimethylmethane diglycidyl ether. See Bisphenol A diglycidyl ether 4,4 -Dihydroxydiphenyl ketone. See 4,4 -Dihydroxybenzophenone 2,2-(4,4-Dihydroxydiphenyl) propane p,p -Dihydroxydiphenylpropane. See Bisphenol A Dihydroxydiphenylsilane. See Diphenylsilanediol 4,4 -Dihydroxydiphenyl sulfone CAS 80-09-1 EINECS/ELINCS 201-250-5 Synonyms Bis (4-hydroxyphenyl) sulfone Bis (p-hydroxyphenyl) sulfone 4,4 -Bisphenol S Bisphenol S BPS 1 p,p -Dihydroxydiphenyl sulfone 4-Hydroxyphenyl sulfone Phenol, 4,4 -sulfonylbis- Phenol, 4,4 -sulfonyldi- SDP 1,1 -Sulfonylbis (4-hydroxybenzene) Sulfonyl bisphenol 4,4 -Sulfonylbisphenol 4,4 -Sulfonyldiphenol... 

Bis-(4-hydroxyphenyl)-sulfone is also addressed as 4,4 -dihydroxydiphenyl sulfone, or 4,4 -bisphenol S. 

Telechelic compounds are oligomers or low-molecular-weight polymers carrying monofunctional terminal groups or reactive terminal groups, respectively, on both chain ends. Block suifone copolymers have been synthesized from hydroxy-telechelic sulfonated PESs and fluorotelechelic PESs. As a monomer for the sulfonated hydroxy-telechelic compound, 3,3 -sulfonyl bis-(6-hydroxybenzene sulfonic acid) disodium salt is used [34]. This compound is synthesized from bis-(4-hydroxyphenyl)-sulfone by sulfonation with concentrated sulfuric acid and subsequent neutralization. 

The monomers can be chain extended with bis-(4-fluorophenyl)suifone or bis-(4-hydroxyphenyl)-sulfone, respectively, in a next condensation step. 

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