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CAS Number:1184-84-5 and 3039-83-6
Molar mass:108.11 g·mol−1
Synonyms:
Vinylsulfonic acid; VINYL SULFONIC ACID; VINYL sulfonıc acıd; VINYL sulfonic acid; VSA; Ethylenesulfonic acid sodium salt; Sodium vinylsulfonate solution; Vinylsulfonic acid sodium salt; VINYLSULFONIC ACID; ethenesulfonic acid; Ethylenesulfonic acid; Ethylenesulphonic acid; VINYLSULPHONIC ACID; Sodium ethenesulfonate(25%Nasalt); Sodium ethylenesulfonate; vinyl sulfonic acid; ethylene sulfonic acid; Vinylsulfonic Acid; Vinylsulfonic acid; VINYL SULFONIC AIC; VINYL sulfonıc acıd; VINYL sulfonic acid; VSA; Ethylenesulfonic acid sodium salt; Sodium vinylsulfonate solution; Vinylsulfonic acid sodium salt; VINYLSULFONIC ACID; ethenesulfonic acid; Ethylenesulfonic acid; Ethylenesulphonic acid; VINYLSULPHONIC ACID; Sodium ethenesulfonate(25%Nasalt); Sodium ethylenesulfonate; vinyl sulfonic acid; ethylene sulfonic acid; Vinylsulfonic Acid; Vinilsülfonik asit; CANLI SÜLFONİK AIC; VINYL sulfonıc acıd; VİNİL sülfonik asit; VSA; Etilen sülfonik asit sodyum tuzu; Sodyum vinilsülfonat çözeltisi; Vinil sülfonik asit sodyum tuzu; VİNİLSÜLFONİK ASİT; etensülfonik asit; Etilen sülfonik asit; Etilen sülfonik asit; VİNİLSÜLFONİK ASİT; Sodyum etensülfonat (% 25 Nasalt); Sodyum etilensülfonat; vinil sülfonik asit; etilen sülfonik asit; Vinilsülfonik asit; Acide vinylsulfonique; VINYL SULFONIC AIC; VINYL sulfonıc acıd; Acide VINYL sulfonique; VSA; Sel de sodium de l'acide éthylènesulfonique; Solution de vinylsulfonate de sodium; Sel de sodium d'acide vinylsulfonique; ACIDE VINYLSULFONIQUE; acide éthénesulfonique; Acide éthylènesulfonique; Acide éthylènesulfonique; ACIDE VINYLSULPHONIQUE; Éthénesulfonate de sodium (25% Nasalt); Éthylènesulfonate de sodium; acide vinylsulfonique; acide éthylène sulfonique; Acide vinylsulfonique,
Properties of Vinylsulfonic acid:
Chemical formula: C17H34O2
Molar mass: 270.457 g·mol−1
Density: 0.85 g/cm³
Boiling point: 167 °C (333 °F; 440 K) at 9 mmHg
Vinylsulfonic acid is the organosulfur compound with the formula CH2=CHSO3H. It is the simplest unsaturated sulfonic acid.
The C=C double bond is a site of high reactivity.
Polymerize gives polyvinylsulfonic acid, especially when used as a comonomer with functionalized vinyl and (meth)acrylic acid compounds.
It is a colorless, water-soluble liquid, although commercial samples can appear yellow or even red.
Vinylsulfonic acid is produced industrially by the alkaline hydrolysis of carbyl sulfate with subsequent acidification of the resulting vinyl sulfonate salt.
The reaction is highly exothermic (reaction enthalpy: 1,675 kJ/kg) and requires exact maintenance of temperature and pH during the hydrolysis.
When calcium hydroxide is used as the hydrolysis medium, a solution of calcium vinyl sulfonate is obtained.
Acidification of this hydrolysis mixture with sulfuric acid gives vinylsulfonic acid, together with the poorly soluble calcium sulfate.
Vinylsulfonic acid also can be prepared by dehydration of isethionic acid with phosphorus pentoxide.
Vinylsulfonic acid can also be prepared by sulfochlorination of chloroethane, dehydrohalogenation to vinylsulfonyl chloride and subsequent hydrolysis of the acid chloride.
The activated C=C double bond of vinylsulfonic acid reacts readily with nucleophiles in an addition reaction.
2-Aminoethanesulfonic acid is formed with ammonia and 2-methylaminoethanesulfonic acid with methylamine.
Vinylsulfonic acid is the monomer in the preparation of highly acidic or anionic homopolymers and copolymers.
These polymers are used in the electronic industry as photoresists, as ion-conductive polymer electrolyte membranes (PEM) for fuel cells.
For example, transparent membranes with high ion exchange capacity and proton conductivity can be produced from polyvinylsulfonic acid.
Vinylsulfonic acid may also be grafted to polymeric supports (e.g. polystyrene) to give highly acidic ion exchangers, which used as catalysts for esterification and Friedel-Crafts acylations.
Where the sulfonic acid functionality is not essential, the much more usable alkaline aqueous solution of sodium vinylsulfonate is used, which is obtained directly in the alkaline hydrolysis of the carbyl sulfate and is commercially supplied as an aqueous solution.
