Production Methods

Diepoxybutane is prepared by chlorination of butadiene followed by epoxidation with peracetic acid, with subsequent hydrolysis of the epoxide group and final reepoxidation with caustic.

Reactivity Profile

Epoxides, such as 1,3-BUTADIENE DIEPOXIDE, are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.

Hazard

Probable carcinogen; neoplastigen; tumorigenic; poison; mutagen.

Health Hazard

Severe skin and eye irritant. Accidental minor exposure caused swelling of the eyelids, upper respiratory tract irritation and painful eye irritation 6 hours after exposure.NOTE: The dl- and meso-forms (CAS Registry Numbers 298-18-0 and 564-00-1, respectively) as well as the L(-) form (CAS Registry Number 30031-64-2) have all been determined to be positive animal carcinogens.

Fire Hazard

When heated to decomposition 1,3-BUTADIENE DIEPOXIDE emits acrid smoke and irritating fumes.

Safety Profile

Confirmed carcinogen withexperimental tumorigenic data. Poison by ingestion,inhalation, skin contact, and intraperitoneal routes.Human mutation data reported. A severe skin and eyeirritant. When heated to decomposition it emits acridsmoke and irritat

Carcinogenicity

Diepoxybutane is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.

General Description

1,3-Butadiene diepoxide (also known as meso-bisoxirane) is a compound of interest as a potential building block for natural product synthesis and as a toxic metabolite of butadiene. It exists in two conformations (trans and gauche) in fluid phases, with the trans conformer (C_i symmetry) being more stable than the gauche conformer (C₁ symmetry). Spectroscopic studies reveal a ΔH value of 0.31 ± 0.10 kcal/mol between these conformers in the liquid state, and only the trans form persists in the solid state. The gauche conformer has a dipole moment of 3.03 D and a dihedral angle of approximately 60° between the H-C-C'-H' atoms.