1568. 2,3-Butylene Glycol

Nomenclature

CAS number: 513-85-9
2,3-Butanediol; 2,3-dihydroxybutane; dimethylethylene glycol.
C4H10O2; mol wt 90.12.
C 53.31%, H 11.18%, O 35.51%.

Description and references

Occurs in 3 isomeric forms: meso- or erythro-, d(-)-threo-, and l(+)-threo-forms. The commercial product is usually either the meso- or the d(-)-form. Prepn of meso-form from trans-2,3-epoxybutane and of dl-form from cis-2,3-epoxybutane: Wilson, Lucas, J. Am. Chem. Soc. 58, 2396 (1936). Prepn of d(-)- and l(+)-forms from corresponding d- and l-mannitols: Rubin et al., ibid. 74, 425 (1952). Manuf of d(-)-form by fermentation of carbohydrate solns with organisms of the Bacillus subtilis group: Vergnaud, US 2529061 (1950 to Usines de Melle). Manuf from 2-butene: Cosby et al., US 2808429 (1957 to Allied Chem.); Keith et al., US 2974161 (1961 to Sinclair); from 2-butyne: Saegebarth, US 3157704 (1964 to du Pont). Configuration: Morell, Auernheimer, J. Am. Chem. Soc. 66, 792 (1944); Leroux, Lucas, ibid. 73, 41 (1951); Rubin et al., loc. cit.

Chemical structure

Derivative

meso-Form (erythro-Form).

Nomenclature

CAS number: 5341-95-7
(2R,3S)-rel-2,3-Butanediol.

Properties

Hygroscopic crystals from dry diisopropyl ether, mp 34.4°. bp742 181.7°, bp16 89°. d425 0.9939. nD35 1.4324. Moderately sol in diisopropyl ether.

Derivative

dl-threo-Form.

Nomenclature

CAS number: 6982-25-8
(2R,3R)-rel-2,3-Butanediol.

Properties

Hygroscopic crystals from diisopropyl ether, mp 7.6°. bp742 172.7°, bp16 86°. nD25 1.4310. Very sol in diisopropyl ether.

Derivative

d(-)-threo-Form.

Nomenclature

CAS number: 24347-58-8
(2R,3R)-2,3-Butanediol.

Properties

mp 19.7°. bp745 179-180°, bp10 77.5-78°. d425 0.9869. nD25 1.4315. [α]D25 -13.0° (neat).

Derivative

l(+)-threo-Form.

Nomenclature

CAS number: 19132-06-0
(2S,3S)-2,3-Butanediol.

Properties

bp 179-182°. d25 0.9872. nD25 1.4306.