Chemical properties

1,3-Propanesultone, also known as 3-hydroxypropanesulfonic acid γ-sultone; 1,2-oxathiolane, 2,2-dioxide, is a white crystalline powder or colorless liquid compound. Melting point is 30–33°C, density is 1.392 g mL?1 (25°C), boiling point is 180°C/30 mmHg. Soluble in water (100 g·L?1); soluble in most organic solvents, including THF, dioxane, DMF and ether. Insoluble in hexane and other aliphatic hydrocarbons. It reacts slowly with water to form 3-hydroxypropanesulfonic acid. It releases toxic sulfur oxide fumes when decomposed. Therefore, it should be stored away from moisture.

Uses

1,3-Propanesultone is widely used in the preparation of different classes of surfactants; for the functionalization of dyes, polymers, nucleosides and proteins to improve their hydrophilicity; and can also be used as a protected form of sulfonic acids, sulfonamides and sulfonates. N-sulfopropyl CS derivatives can be prepared by ring-opening reaction using 1,3-Propanesultone as a sulfonating agent and aqueous acetic acid (2 wt%) as a solvent under nitrogen atmosphere and 30°C. These derivatives have significant effects on hemolysis, red blood cell, white blood cell, platelet aggregation, C3 protein consumption assay and whole blood clotting time, and are widely used in the medical field.

In addition, 1,3-Propanesultone can also be used as an additive for overlithiated layered oxide (OLO) electrolytes to enhance interfacial stability. The surface film derived from 1,3-Propanesultone can effectively inhibit metal dissolution and adverse reactions of electrolytes on the positive electrode (PE), thereby significantly improving the cycling performance of OLO electrodes.

Carcinogenicity

1,3-Propane sultone is highly carcinogenic. It forms DNA-DNA, DNA-RNA, RNA-RNA, DNA-protein, and possibly RNA-protein complexes in vitro. DNA treated with 1,3-propane sultone has increased attachment to microsomal membranes, as well as enhanced adsorption and penetration into Ehrlich ascites tumor cells. It is a small ring alkylated carcinogen that can form such macromolecular complexes. These highly diverse structures may be involved in chemical mutagenesis and tumorigenesis.

References:

[1] SIKERVAR V. 1,3‐Propanesultone[C]. 2014: 0. DOI:10.1002/047084289X.RN01798.

[2] YIM T, KIM S H, WOO S G, et al. 1,3-Propanesultone as an effective functional additive to enhance the electrochemical performance of over-lithiated layered oxides[J]. RSC Advances, 2014, 37: 19172-19176. DOI:10.1039/C4RA01441C.

[3] P E ZELDIN. Macromolecular complexes produced by 1,3-propanesultone.[J]. Cancer research, 1975, 35 6: 1445-1452.