1,2-Butanediol

1,2-Butanediol
IUPAC name

Butane-1,2-diol
Other names

1,2-Dihydroxybutane
α-Butylene glycol
Identifiers
CAS number 584-03-2 Y
ChemSpider 10948 Y
UNII RUN0H01QEU Y
EC-number 209-527-2
ChEBI CHEBI:52682 Y
RTECS number EK0380000
Jmol-3D images Image 1
Image 2
Properties[1][2][3]
Molecular formula C4H10O2
Molar mass 90.121 g/mol
Density 1.0023 g/cm3 (20 °C)
Melting point

−50 °C[note 1]
Boiling point

195–196.9 °C
96.5 °C (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 ΔfHo298		 −532.8 kJ/mol
Std enthalpy of
combustion ΔcHo298		 −2479 kJ/mol
Hazards[4]
MSDS ICSC 0395
EU Index not listed
Flash point 90 °C
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
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

1,2-Butanediol is a vic-diol (glycol) first described by Charles-Adolphe Wurtz in 1859.[5] It is produced industrially as a byproduct of the production of 1,4-butanediol from butadiene,[6] and is also a byproduct of the catalytic hydrocracking of starches and sugars such as sorbitol to ethylene glycol and propylene glycol.[7][note 2] It is used to produced polyester resins and plasticizers,[3][6] and is a potential feedstock for the industrial production of α-ketobutyric acid, a precursor to many amino acids.[8]

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. ^ a b 1,2-Butanediol, SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, February 1995, http://www.inchem.org/documents/sids/sids/584032.pdf .
  4. ^ 1,2-Butanediol, International Chemical Safety Card 0395, Geneva: International Programme on Chemical Safety, March 1996, http://www.inchem.org/documents/icsc/icsc/eics0395.htm .
  5. ^ Wurtz, A. (1859), Ann. Chim. Phys. 55: 400 .
  6. ^ a b US 4596886, Hasegawa, Ryuichi & Kohji Hayashi, "Polyester containing impure 1,2-butanediol" .
  7. ^ 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" .
  8. ^ US 5155263, Imanari, Makoto; Hiroshi Iwane & Masashi Suzuki et al., "Process for preparing α-ketobutyric acid" .

External links