3676. Erythritol Anhydride

Nomenclature

CAS number: 564-00-1
(2R,2′S)-rel-2,2′-Bioxirane; meso-1,2:3,4-diepoxybutane; butadiene diepoxide; butadiene dioxide; butanedione; Bioxiran.
C4H6O2; mol wt 86.09.
C 55.81%, H 7.02%, O 37.17%.

Description and references

Prepn from erythrityl chlorohydrin: Przybytek, Ber. 17, 1091 (1884); by refluxing 1,4-dichloro-2,3-butanediol in tetrahydrofuran with NaOH: Reppe, Ann. 596, 141 (1955); meso-form from 1,4-dihydroxy-2-butene or from 3,4-epoxy-1-butene and dl-form from 1,4-dibromo-2-butene: Beech, J. Chem. Soc. 1951, 2483 DOI. Use to prevent microbial spoilage: H. D. Michener, J. C. Lewis, US 2934439 (1960 to U.S. Secy of Agr.). Toxicity data: H. F. Smyth et al., Arch. Ind. Hyg. Occup. Med. 10, 61 (1954).

Chemical structure

Properties

Liquid. d418 1.113. bp 138°; bp23 50-51°. Flammable. meso-form, bp761 140-142°. mp -19°. Compd with piperidine, mp 106° (Beech). Misc with water which hydrolyzes it to erythritol. LD50 orally in rats: 0.078 g/kg (Smyth).

Caution

This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-94.

Use

Curing polymers; crosslinking textile fibers.