Erythritol Anhydride

Title: Erythritol Anhydride
CAS Registry Number: 564-00-1
CAS Name: (2R,2¢S)-rel-2,2¢-Bioxirane
Additional Names: meso-1,2:3,4-diepoxybutane; butadiene diepoxide; butadiene dioxide; butanedione
Trademarks: Bioxiran
Molecular Formula: C4H6O2
Molecular Weight: 86.09
Percent Composition: C 55.81%, H 7.02%, O 37.17%
Literature 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. 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).
Properties: Liquid. d418 1.113. bp 138°; bp23 50-51°. 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).
Melting point: mp -19°; mp 106° (Beech)
Boiling point: bp 138°; bp23 50-51°; bp761 140-142°
Density: d418 1.113
Toxicity data: 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.
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