1,4-Butane sultone Chemical Properties

Melting point:

12-15 °C (lit.)

Boiling point:

>165 °C/25 mmHg (lit.)

Density 

1.331 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.464(lit.)

Flash point:

>230 °F

storage temp. 

Store below +30°C.

solubility 

54g/l (decomposition)

form 

Liquid

color 

Clear colorless to yellow

Water Solubility 

54 g/L (20 ºC) decomposes

Sensitive 

Moisture Sensitive

BRN 

110588

InChIKey

MHYFEEDKONKGEB-UHFFFAOYSA-N

CAS DataBase Reference

1633-83-6(CAS DataBase Reference)

EPA Substance Registry System

1,2-Oxathiane, 2,2-dioxide (1633-83-6)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-40-68-20/21/22

Safety Statements 

22-36/37-45-36

RIDADR 

2810

WGK Germany 

3

RTECS 

RP4300000

TSCA 

Yes

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29349990

Hazardous Substances Data

1633-83-6(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 500 mg/kg

MSDS

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1,4-Butane sultone Usage And Synthesis

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.

Uses

1,4-Butane Sultone is an alkylating agent with weak carcinogenic activity.

Uses

1,4-Butane sultone can be employed as a reactant in the preparation of conjugated polymers which include polybetaine, poly[2-ethynyl-N-(4-sulfobutyl)pyridinium betaine] (PESPB).
It can also be used in the preparation of Bronsted acid catalysts such as 4-(succinimido)-1-butane sulfonic acid and poly(4-vinylpyridinium butane sulfonic acid) hydrogen sulfate. These catalysts facilitate the synthesis of 1-amidoalkyl-2-naphthols, substituted quinolines, and pyrano[4,3-b]pyran derivatives.

Application

1,4-Butane sultone is an intermediate widely used for sulfonated surfactants.It is also applied in photo development and electroplating.It is used as the Intermediate for the production of APIs.It used in 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.

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