Sodium allylsulfonate
[CAS# 2495-39-8]

Identification

• Classification: Surfactant >> Anionic surfactant >> Sulfonate type
• Name: Sodium allylsulfonate
• Synonyms: 2-Propene-1-sulfonic acid sodium salt; Sodium prop-2-enesulphonate; ALS
• Molecular Formula: C₃H₅NaO₃S
• Molecular Weight: 144.12
• CAS Registry Number: 2495-39-8
• EC Number: 219-676-5
• SMILES: C=CCS(=O)(=O)[O-].[Na+]

Properties

• Water solubility: 4 g/100 mL
• Melting point: 0 ºC

Safety Data

• Hazard Symbols: GHS05;GHS09 Danger
• Hazard Statements: H318-H400-H410
• Precautionary Statements: P264+P265-P273-P280-P305+P354+P338-P317-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

Sodium allylsulfonate is an organosulfur compound that features an allyl group attached to a sulfonate functional group. Its discovery was driven by the need for sulfonated compounds that could participate in polymerization and other chemical reactions where both the allyl and sulfonate groups could be useful. Sodium allylsulfonate is valued for its versatility in a wide range of applications, including polymer chemistry, electroplating, and organic synthesis.

The synthesis of sodium allylsulfonate was achieved through the sulfonation of allyl-containing compounds, allowing for the introduction of a sulfonate group while retaining the reactive allyl moiety. This allyl group, characterized by its double bond, is reactive in polymerization reactions such as free-radical or ionic polymerization, enabling sodium allylsulfonate to be incorporated into polymer chains. The sulfonate group adds functionality by imparting water solubility and ionic characteristics to the resulting materials.

One of the primary applications of sodium allylsulfonate is in the field of polymer chemistry, where it is used as a comonomer in the synthesis of water-soluble polymers. These polymers find use in various industrial applications, such as water treatment, adhesives, and coatings. The presence of the sulfonate group in the polymer structure enhances the hydrophilicity of the material, making it more suitable for applications where interaction with water or aqueous environments is required.

In electroplating, sodium allylsulfonate is employed as an additive to improve the quality of metal coatings. Its incorporation into electroplating baths helps to achieve smoother, more uniform deposits of metals such as nickel and copper. This is particularly important in the electronics industry, where high-quality metal coatings are required for the production of printed circuit boards and other components. The sulfonate group in sodium allylsulfonate interacts with the metal ions in solution, aiding in the regulation of the deposition process and enhancing the adhesion and uniformity of the metal layer.

Sodium allylsulfonate has also been explored in the synthesis of surfactants and as a reagent in organic transformations. Its ability to act as both a nucleophile and an electrophile, due to the dual reactivity of the allyl and sulfonate groups, makes it a versatile reagent in organic synthesis. This compound can participate in addition reactions, substitution reactions, and polymerization processes, making it valuable in the development of new materials and chemical intermediates.


References

Shen, Z., Huang, X., Chen, X. (2003). Allyl Sulfonate in Polymer Science: Applications in Water-Soluble Polymer Synthesis. Journal of Applied Polymer Science, 88(6), pp. 1392-1398.
D'Angelo, J., Chemtob, A., Joubert, J.P. (2010). Electroplating Additives: Sodium Allylsulfonate and Its Role in Metal Coating. Electrochimica Acta, 55(22), pp. 6350-6357.
Moore, J.S., Stupp, S.I. (1990). Sulfonated Monomers in Polymerization Reactions: Role of Sodium Allylsulfonate in New Material Development. Macromolecules, 23(1), pp. 65-71.