2,3-Butylene Glycol
Title: 2,3-Butylene Glycol
CAS Registry Number: 513-85-9
CAS Name: 2,3-Butanediol
Additional Names: 2,3-dihydroxybutane; dimethylethylene glycol
Molecular Formula: C4H10O2
Molecular Weight: 90.12
Percent Composition: C 53.31%, H 11.18%, O 35.51%
Line Formula: CH3CH(OH)CH(OH)CH3
Literature 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.
 
Derivative Type: meso-Form (erythro-Form)
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.
Melting point: mp 34.4°
Boiling point: bp742 181.7°; bp16 89°
Index of refraction: nD35 1.4324
Density: d425 0.9939
 
Derivative Type: DL-threo-Form
Properties: Hygroscopic crystals from diisopropyl ether, mp 7.6°. bp742 172.7°, bp16 86°. nD25 1.4310. Very sol in diisopropyl ether.
Melting point: mp 7.6°
Boiling point: bp742 172.7°; bp16 86°
Index of refraction: nD25 1.4310
 
Derivative Type: D(-)-threo-Form
Properties: mp 19.7°. bp745 179-180°, bp10 77.5-78°. d425 0.9869. nD25 1.4315. [a]D25 -13.0° (neat).
Melting point: mp 19.7°
Boiling point: bp745 179-180°; bp10 77.5-78°
Optical Rotation: [a]D25 -13.0° (neat)
Index of refraction: nD25 1.4315
Density: d425 0.9869
 
Derivative Type: L(+)-threo-Form
Properties: bp 179-182°. d25 0.9872. nD25 1.4306.
Boiling point: bp 179-182°
Index of refraction: nD25 1.4306
Density: d25 0.9872

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