Diepoxybutane

Diepoxybutane is a highly reactive epoxide that exists as a colorless liquid at room temperature[2]. It is known by several names, including butane diepoxide, butadiene diepoxide, and 1,2:3,4-diepoxybutane[1][2]. This compound is characterized by its high reactivity, which is more pronounced than that of other ethers, due to its cyclic ether structure containing a three-atom ring that approaches an equilateral triangle[2].

Physical and Chemical Properties

Diepoxybutane has a molecular weight of 86.1, a specific gravity of 0.96, and a melting point of -19°C (for the meso form)[1]. Its boiling point is 138°C, and it has a log Kow of -0.28, indicating its hydrophilic nature[1]. The compound is highly soluble in water, with a solubility of 1,000 g/L, and has a vapor pressure of 3.9 mm Hg at 20°C[1].

Carcinogenicity and Toxicity

Diepoxybutane is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals[1]. Although no epidemiological studies have been identified that evaluate the relationship between human cancer and exposure specifically to diepoxybutane, its carcinogenic potential is recognized[1]. The compound is also highly toxic, with symptoms of exposure including swollen eyelids, irritation of the upper respiratory tract, and painful eye irritation[4].

Uses

Diepoxybutane has been used as a research chemical, a chemical intermediate, a curing agent for polymers, a cross-linking agent for textile fabrics, and as a preservative[1][2]. It is also used in the diagnosis of Fanconi anemia, a genetic disorder characterized by chromosomal instability, due to its ability to induce chromosomal breaks[5].

Environmental Fate and Exposure

Diepoxybutane is not expected to persist in the environment due to its physical and chemical properties[1]. If released to air, it is expected to exist in the vapor state and be degraded by photochemically produced hydroxyl radicals, with a half-life of 16 days[1]. If released to water or soil, it is expected to volatilize, and it is not expected to adsorb to soils or sediments or to bioaccumulate in aquatic or terrestrial organisms[1]. The primary routes of potential human exposure to diepoxybutane are inhalation and dermal contact[1].

Availability and Production

Diepoxybutane is not produced commercially in the United States, but it was available from eleven suppliers, including four U.S. suppliers, in 2009[1]. No data on U.S. imports or exports of diepoxybutane were found[1].

Citations:

[1] https://ntp.niehs.nih.gov/sites/default/files/ntp/roc/content/profiles/diepoxybutane.pdf

[2] https://en.wikipedia.org/wiki/Diepoxybutane

[3] https://www.sigmaaldrich.com/US/en/product/aldrich/202533

[4] https://pubchem.ncbi.nlm.nih.gov/compound/1_2_3_4-Diepoxybutane

[5] https://www.sciencedirect.com/topics/pharmacology-toxicology-and-pharmaceutical-science/diepoxybutane