1,2-Butanediol

1,2-Butanediol

Names
IUPAC name Butane-1,2-diol
Other names 1,2-Dihydroxybutane α-Butylene glycol
Identifiers
CAS Number	584-03-2
ChEBI	CHEBI:52682
ChemSpider	10948
EC Number	209-527-2
Jmol interactive 3D	Image Image
RTECS number	EK0380000
UNII	RUN0H01QEU
InChI InChI=1S/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3 Key: BMRWNKZVCUKKSR-UHFFFAOYSA-N InChI=1/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3 Key: BMRWNKZVCUKKSR-UHFFFAOYAV
SMILES OCC(O)CC CCC(CO)O
Properties[1][2][3]
Chemical formula	C4H10O2
Molar mass	90.121 g/mol
Density	1.0023 g/cm^3 (20 °C)
Melting point	−50 °C (−58 °F; 223 K)[note 1]
Boiling point	195 to 196.9 °C (383.0 to 386.4 °F; 468.1 to 470.0 K) (96.5 °C at 10 mmHg)
Solubility in water	miscible
Solubility	soluble in ethanol, acetone; sparingly soluble in esters and ethers; insoluble in hydrocarbons
Refractive index (nD)	1.4378 (20 °C)
Viscosity	7.3 mPa s (20 °C)
Thermochemistry
Std enthalpy of formation (ΔfH^o298)	−532.8 kJ/mol [4]
Std enthalpy of combustion (ΔcH^o298)	−2479 kJ/mol
Hazards[5]
Safety data sheet	ICSC 0395
Flash point	90 °C (194 °F; 363 K)
Related compounds
Related butanediols	1,3-Butanediol 1,4-Butanediol 2,3-Butanediol
Related compounds	Ethylene glycol Propylene glycol 2-Hydroxybutyraldehyde 2-Hydroxybutyric acid α-Ketobutyric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1,2-Butanediol is a vic-diol (glycol) first described by Charles-Adolphe Wurtz in 1859.^[6] It is produced industrially as a byproduct of the production of 1,4-butanediol from butadiene,^[7] and is also a byproduct of the catalytic hydrocracking of starches and sugars such as sorbitol to ethylene glycol and propylene glycol.^{[8][note 2]} It is used to produce polyester resins and plasticizers,^[3][7] and is a potential feedstock for the industrial production of α-ketobutyric acid, a precursor to many amino acids.^[9]

Notes

1. The value of −50 °C for the melting point is taken from Ullmann's Encyclopedia of Industrial Chemistry and used by the Hazardous Substances Data Bank and the OECD Screening Information Dataset. Other reported values of the melting point range from −114 °C to −30 °C.
2. The catalytic hydrocracking of starches and sugars has been successfully commercialized by S2G Biochem Inc. in partnership with International Polyol Chemical, Inc., as of 2007. http://www.s2gbiochem.com/technology.html

References

1. Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-190. ISBN 0-8493-0462-8..
2. Ullmann's Encyclopedia of Industrial Chemistry A1, Weinheim: Wiley-VCH, 2005, p. VA4 461.
3. 1,2-Butanediol (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, February 1995.
4. Moureu, H.; Dode, M. (1937), "Chaleurs de formation de l'oxyde d'ethylene, de l'ethanediol et de quelques homologues", Bull. Soc. Chim. Fr. 4: 637–47.
5. 1,2-Butanediol, International Chemical Safety Card 0395, Geneva: International Programme on Chemical Safety, March 1996.
6. Wurtz, A. (1859), Ann. Chim. Phys. 55: 400.
7. US 4596886, Hasegawa, Ryuichi & Kohji Hayashi, "Polyester containing impure 1,2-butanediol" .
8. US 4966658, Berg, Lloyd, "Recovery of ethylene glycol from butanediol isomers by azeotropic distillation" . US 5423955, Berg, Lloyd, "Separation of propylene glycol from 1,2-butanediol by azeotropic distillation" .
9. US 5155263, Imanari, Makoto; Hiroshi Iwane & Masashi Suzuki et al., "Process for preparing α-ketobutyric acid" .

External links

• International Chemical Safety Card 03
• SIDS Initial Assessment Report for 1,2-Butanediol from the Organisation for Economic Co-operation and Development (OECD)
• NLM Hazardous Substances Data Bank entry for 1,2-butanediol