Biphenyl-4-sulfonic acid

Biphenyl and Derivatives (Table VII). Biphenyl-4-sulfonic acid can be prepared very satisfactorily by sulfonation with sulfuric acid in nitrobenzene solution (90% yield) or by the action of chlorosulfonic acid in tetrachloroethane at 50°." Sulfuric acid alone either gives a mixture of the 4-mono- and 4,4 -di-sulfonic adds with unchanged hydrocarbon or, with excess reagent, yields chiefly the di- derivative. The monosulfonic acid is readily freed from the disulfonic acid through its sparingly soluble copper salt the disulfonic acid remains in solution and can be crs stallized... 

This method is a modification of that of Buckles, Hausman, and Wheeler.2 4,4 -Dibromobiphenyl has also been prepared by the bromination of biphenyl in water,3 carbon disulfide,4 and glacial acetic acid 6 by the bromination of a mixture of biphenyl-sulfonic acids in dilute sulfuric acid 6 by the action of sodium carbonate on the perbromide obtained from the reaction of di-azotized benzidine with bromine water 7 and by passing />-di-bromobenzene vapor through a red-hot tube.8... 

Minor Uses. Small amounts of benzene find use in production of benzene-sulfonic acid. y -Benzenedisulfonic acid is used to produce resorcinol [108-46-3] (1,3-dihydroxybenzene). Benzene is thermally dimerized to yield biphenyl [92-52-4] Benzene can also be converted... 

Rhodococcus sp. Strain T09 A Rhodococcus strain T09 was isolated by enrichment on media-containing BT. The desulfurization mechanism of this organism was reported to be similar to Gordonia sp. 213E due to the observation of similar intermediates however, the substrate specificity was different. The strain T09 could use 2-methyl, 3-methyl and 5-methyl BT apart from BT as sole source of sulfur for growth, but not 7-methyl or ethyl derivatives. Additionally, it could also use methyl thiobenzothiazole, marcaptobenzothiazole, as well as benzene sulfide, benzene sulfonate, biphenyl sulfinate, dimethyl sulfate, dimethyl sulfone, dimethyl sulfide, methane sulfonic acid, thiophene, and taurine as sole sulfur sources. However, it could not grow on DBT or DBT sulfone. 

Principally, one commercially available sulfonated diamine (4,4 -diamino-2,2 -biphenyl disulfonic acid) has been used to synthesize sulfonated polyimides. In addition to the commercially available diamine, several novel sulfonated diamines incorporating flexible or kinked structures have been prepared in Okamoto s lab. " The chemical structures and names of all five diamines are shown in Figure 23. 

Uses Manufacture of ethylbenzene (preparation of styrene monomer), dodecylbenzene (for detergents), cyclohexane (for nylon), nitrobenzene, aniline, maleic anhydride, biphenyl, benzene hexachloride, benzene sulfonic acid, phenol, dichlorobenzenes, insecticides, pesticides, fumigants, explosives, aviation fuel, flavors, perfume, medicine, dyes, and many other organic chemicals paints, coatings, plastics and resins food processing photographic chemicals nylon intermediates paint removers rubber cement antiknock gasoline solvent for fats, waxes, resins, inks, oils, paints, plastics, and rubber. 

The 3,7-disulfonyl chloride of dibenzothiophene 5,5-dioxide has been isolated from the reaction of biphenyl with chlorosulfonic acid. The reaction proceeds via the 2,4,4 -trisulfonyl chloride of biphenyl. This reaction has now been extended to give sulfonic acid derivatives of 3-phenyl- and 3-biphenylyldibenzothiophene 5,5-dioxide. Treatment of p-terphenyl with oleum or chlorosulfonic acid at 100° yields (141a) (46%), and similarly p-quaterphenyl yields 141b (47%). A later... 

Since the publication of CHEC-II(1996), there have been very few examples related to the reactivity of substituents attached to ring carbon atoms. One case involves the reaction of 3-benzylidene-2,3-dihydro-2-methyl-l,2-benzothiazin-4-one 1,1-dioxide 163 with the alkylidenephosphorane derived from salt 164 forming the tricyclic-fused ring compound 165 (Scheme 20) <1996J(P1)2541>. This material 165 was oxidized with 2,3-dichloro-5,6-dicyano-l,4-benzoquinone (DDQ) affording the biphenyl 166. Ring-opened product 167 was produced from 165 upon exposure to />-toluene-sulfonic acid and heat. 

Minor Uses. Small amounts of benzene find use in production of benzene-sulfonic acid. ///- B enz ene dis ulfonic acid is used to produce resorcinol [108-46-3], C6H602, (1,3-dihydroxybenzene). Benzene is thermally dimerized to yield biphenyl [92-52-4], C12H10. Benzene can also be converted into />-diisopropylbenzene [100-18-5], C12H18, which is oxidized to hydroquinone (1,4-dihydroxybenzene), a useful antioxidant. Because of its well-recognized toxicity, litde benzene is employed for solvent purposes, and then only when no suitable substitutes are available. 

Potent inhibition of the herpes simplex virus has been observed using biphenyl disulfonic acid urea copolymers. Sulfonic acid derivatives have been shown to be potent antihuman immunodeficiency virus (anti-HIV) agents. 

Meyer32 has shown that 2-(stilben-4-yl)- and 7-styrylbenzo[h]furans containing sulfonic acid groups can be prepared from the phenyl-iminomethyl derivatives of benzene, biphenyl, and naphthalene. 

Distyrylbiphenyls, discovered in 1967, can be produced in a similar way to distyrylbenzenes [34], The reaction of 4,4 -bis(chloromethyl)biphenyl with trimethyl phosphite yields 4,4 -bis(dimethoxyphosphonomethyl)biphenyl [27344-43-0. Reaction with, for example, benzaldehyde-2-sulfonic acid gives 4,4 -di(2-sulfostyryl)biphenyl disodium salt (10) [27344-41-8],... 

Wittig et al. separated biphenyl-a-phenyl-naphthylphosphine (76) into its enantiomers by using D-(+)-campher-10-sulfonic acid the rotational strengths are ... 

BIPHENYL ETHER (101-84-8) Combustible liquid (flash point 239°F/1 IS C). Contact with strong acids, strong oxidizers may cause fire and explosions. Incompatible with chloro-sulfonic acid. Attacks some plastics, rubber, and coatings. How or agitation of substance may generate electrostatic charges due to low conductivity. 

Chart 6.9 Device used to produce white light. PEDOT poly(3,4-ethylenedioxythiophene), PSS poly(styrene sulfonic acid), CBP 4,4 -di(N-carbazolyl)-biphenyl (see Chart 6.10),... 

Di-(styryl)-biphenyls are also obtained by the Homer-Wittig reaction of the phosphonate derived from l,4-bis-(chloromethyl)-biphenyl (37) and triethyl phosphite (38) with benzaldehyde-2-sulfonic acid (40), giving the corresponding distyrylbiphenyl disodium salt (e.g., 41, see Scheme 28.2). This class of FWAs is widely used in detergent applications due to its unique whitening benefits... 

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