Description
4-hydroxybenzenesulfonic acid is an arenesulfonic acid that is phenol substituted by a sulfo group at C-4. It is functionally related to a phenol. Results obtained in a comparative study using the disulfide-bridge containing peptide deaminoarginine-vasopressin and several commonly used matrices indicate that the reduction-inhibiting efficiency of 4-hydroxy benzene sulfonic acid is comparable to that of 3-nitrobenzyl alcohol while reduction is found to be important in matrices such as thioglycerol and glycerol. Experiments conducted on peptides such as met-enkephalin and bradykinin, nucleosides and other polar compounds reveal that 4-hydroxybenzenesulfonic acid is a good solvent and has physical properties similar to glycerol. This new matrix material is a radical scavenger, is surface active, allows persistent secondary-ion beams, and produces a low background signal[1].
Chemical Properties
yellowish oily liquid
Uses
4-Hydroxybenzenesulfonic Acid is used as a redox-mediator in the laccase-catalyzed degradation of indigo, a textile dye. Also used in oilfield chemicals, metal working, and as a polymerization catalyst.
Application
Crude 4-hydroxybenzenesulfonic acid obtained by hot sulfonation, i.e., mixed with 2- hydroxybenzenesulfonic acid, is used as such in the manufacture of synthetic tanning agents. Condensation products of phenolsulfonic acid mixtures with formaldehyde improve the dyeing properties of polyamide fibers. 4-Hydroxybenzenesulfonic acid and 2-halogenomalonic esters form the corresponding ethers, which are used in the manufacture of polyesters with improved affinity for basic dyes. If a mixture of hydroxybenzenesulfonic acids and bis(hydroxyphenyl) sulfone is condensed with formaldehyde, and hydrogensulfite is subsequently added, substances with good dispersing effects on dyes are obtained. They also are used as thinning agents for cement. Most of the 4-hydroxybenzenesulfonic acid is used as an additive for electroplating baths. By comparison, the acid is relatively unimportant as a dye intermediate. With ethylene oxide it forms poly(ethoxy)oxybenzenesulfonic acid, which can be used as a plasticizer and emulsifier.
Definition
ChEBI: An arenesulfonic acid that is phenol substituted by a sulfo group at C-4.
Production Methods
The synthesis of 4-Hydroxybenzenesulfonic acid is as follows：Phenol (25 kg) and 96% sulfuricacid(28 kg) are heated to 50 ℃; then1.25 kg additional sulfuric acid is added and the reaction mixture is heated at 110 ℃ for 5 – 6 h. Reaction water, together with about 5% of the phenol, is distilled off during this period. Yield 95%.
Flammability and Explosibility
Nonflammable
References
[1] J. Visentini, Michel J. Bertrand, P. M. Nguyen. “The use of 4-hydroxybenzenesulfonic acid as a reduction-inhibiting matrix in liquid secondary-ion mass spectrometry.” Rapid Communications in Mass Spectrometry 5 12 (1991): 586–590.
