Butane-1,2-diol
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| 1,2-Butanediol | |
|---|---|
| IUPAC name | Butane-1,2-diol |
| Other names | 1,2-Dihydroxybutane α-Butylene glycol |
| Identifiers | |
| InChI | InChI=1/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3 |
| InChIKey | BMRWNKZVCUKKSR-UHFFFAOYAV |
| Standard InChI | InChI=1S/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3 |
| Standard InChIKey | BMRWNKZVCUKKSR-UHFFFAOYSA-N |
| CAS number | [] |
| EC number | |
| RTECS | EK0380000 |
| ChemSpider | |
| Properties[1][2][3] | |
| Chemical formula | C4H10O2 |
| Molar mass | 90.121 g/mol |
| Density | 1.0023 g/cm3 (20 ºC) |
| Melting point |
−50 °C[note 1] |
| Boiling point |
195–196.9 °C |
| Solubility in water | miscible |
| Solubility | soluble in ethanol, acetone; sparingly soluble in esters and ethers; insoluble in hydrocarbons |
| Refractive index (nD) | 1.4378 (20 ºC) |
| Viscosity | 7.3 mPa s (20 ºC) |
| Thermochemistry[4] | |
| Std enthalpy of formation ΔfH |
−532.8 kJ/mol |
| Std enthalpy of combustion ΔcH |
−2479 kJ/mol |
| Hazards[5] | |
| Material safety data sheet (MSDS) | ICSC |
| EU index number | not listed |
| Flash point | 90 ºC |
| Related compounds | |
| Other butanediols | 1,3-Butanediol 1,4-Butanediol 2,3-Butanediol |
| Other compounds | Ethylene glycol Propylene glycol 2-Hydroxybutyraldehyde 2-Hydroxybutyric acid |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
Butane-1,2-diol 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 butane-1,4-diol 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 produced 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
- ↑ The value of −50 ºC 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.
- ↑ It should be noted that the catalytic hydrocracking of starches and sugars is not currently a major industrial route to ethylene glycol and propylene glycol, partly because of the complexity of the mixtures of polyhydric alcohols which is formed.
References
- ↑ CRC Handbook of Chemistry and Physics, 62nd ed.; Weast, Robert C., Ed.; CRC Press: Boca Raton, FL, 1981; p C-190. ISBN 0-8493-0462-8.
- ↑ Ullmann’s Encyclopedia of Industrial Chemistry, 5th ed.; Wiley-VCH: Weinheim, 2005; Vol. A1, p VA4 461.
- ↑ 3.0 3.1 1,2-Butanediol; SIDS Initial Assessment Report; Organisation for Economic Co-operation and Development, February 1995, <http://www.inchem.org/documents/sids/sids/584032.pdf>.
- ↑ Moureu, H.; Dode, M. Chaleurs de formation de l'oxyde d'ethylene, de l'ethanediol et de quelques homologues. Bull. Soc. Chim. Fr. 1937, 4, 637–47.
- ↑ 1,2-Butanediol; International Chemical Safety Card 0395; International Labour Organization: Geneva, March 1996, <http://www.inchem.org/documents/icsc/icsc/eics0395.htm>.
- ↑ Wurtz, A. Ann. Chim. Phys. 1859, 55, 400.
- ↑ 7.0 7.1 Hasegawa, Ryuichi; Hayashi, Kohji (Mitsubishi Monsanto Chemical Company) Polyester containing impure 1,2-butanediol. US Patent 4596886, published 5 July 1986.
- ↑ Berg, Lloyd Recovery of ethylene glycol from butanediol isomers by azeotropic distillation. US Patent 4966658, published 5 July 1990. Berg, Lloyd Separation of propylene glycol from 1,2-butanediol by azeotropic distillation. US Patent 5423955, published 5 July 1995.
- ↑ Imanari, Makoto; Iwane, Hiroshi; Suzuki, Masashi, et al. (Mitsubishi Petrochemical Co., Ltd.) Process for preparing α-ketobutyric acid. US Patent 5155263, published 5 July 1992.
External links
- International Chemical Safety Card 0395
- 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
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