1,4-Butane sultone

Description

1,4-Butane sultone is an impurity in sulfobutyl ether β-cyclodextrin (SBE-β-CD), and has been reported to be a weak carcinogen. 1,4-Butane sultone can be used for preparation of Br?nsted acidic ionic liquids and the ionic liquid is green, highly water soluble, thermally stable, specific and catalytically stable, and can be used for the preparation of symmetrical 3,3'-diaryloxyoctanone compounds^[1-2].

Chemical properties

Butanesultone is a viscous, clear, colourless – or yellowish/brown – and odourless liquid. When heated, vapours of butanesultone are known to form explosive mixtures with air and are reported to cause explosion hazards.

The Uses of 1,4-Butane sultone

1,4-Butane sultone serves as a reactant in the preparation of conjugated polymers, including polybetaine and poly[2-ethynyl-N-(4-sulfobutyl)pyridinium betaine] (PESPB). It is also utilized in the synthesis of Bronsted acid catalysts such as 4-(succinimido)-1-butane sulfonic acid and poly(4-vinylpyridinium butane sulfonic acid) hydrogen sulfate. These catalysts are known to facilitate the synthesis of 1-amidoalkyl-2-naphthols, substituted quinolines, and pyrano[4,3-b]pyran derivatives.
1,4-Butane sultone is an intermediate widely used in various applications, including the production of sulfonated surfactants and as an alkylating agent with weak carcinogenic activity. It finds use in photo development and electroplating processes and is also employed as an intermediate for the production of active pharmaceutical ingredients (APIs). Additionally, it is used in the synthesis of sulfobutylether-β-cyclodextrin (SEBCD).

Safety Profile

Suspected carcinogen with experimental tumorigenic data. Poison by subcutaneous, intravenous, and intraperitoneal routes. Moderately toxic by ingestion. Experimental reproductive effects. Human mutation data reported. See also SULFONATES. When heated to decomposition it emits toxic fumes of SOx

Synthesis

Performing sulfonation on 3-butylene-1-alcohol or 3-butylene-1-chlorine serving as a raw material and a sulfonating agent under the oxidation-reduction of an initiator;performing acidification after the reaction is finished;performing lactonization by high vacuum dehydration cyclization and azeotropic dehydration cyclization;and finally refining to obtain a 1,4-butane sultone finished product.

References

[1] LAYLA A. TAIB; Mosadegh K. Introduction of novel br?nsted acidic ionic liquids with perchlorate counter-anion for one-pot synthesis of symmetric 3,3′-diaryloxindoles[J]. Research on Chemical Intermediates, 2021. DOI:10.1007/s11164-021-04419-5.
[2] MENG WANG. Determination of Low-ppm Levels of 1,4-Butane Sultone in Sulfobutyl Ether β-Cyclodextrin Using Liquid–Liquid Extraction and GC–MS[J]. Chromatographia, 2012. DOI:10.1007/s10337-012-2275-8.