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1,2-Butanediol

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1,2-Butanediol is the organic compound with the formula HOCH2(HO)CHCH2CH3. It is classified as a vic-diol (glycol. It is chiral, although typically it is encountered as the racemic mixture. It is a colorless liquid.

1,2-Butanediol
Molecular forula of 1,2-Butanediol
Butanediol molecule
Names
IUPAC name
Butane-1,2-diol
Other names
1,2-Dihydroxybutane
α-Butylene glycol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.663
EC Number
  • 209-527-2
RTECS number
  • EK0380000
UNII
Properties[1]
C4H10O2
Molar mass 90.121 g/mol
Density 1.0023 g/cm3 (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)
miscible
Solubility soluble in ethanol, acetone; sparingly soluble in esters and ethers; insoluble in hydrocarbons
1.4378 (20 °C)
Viscosity 7.3 mPa s (20 °C)
Thermochemistry
−532.8 kJ/mol [2]
−2479 kJ/mol
Hazards[3]
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

PreparationEdit

It is produced industrially by hydration of 1,2-epoxybutane.[4][5]

1,2-Butanediol is a byproduct of the production of 1,4-butanediol from butadiene,[6] It is also a byproduct of the catalytic hydrocracking of starches and sugars such as sorbitol to ethylene glycol and propylene glycol.[7]

This diol was first described by Charles-Adolphe Wurtz in 1859.[8]

ApplicationsEdit

It has been patented for the production of polyester resins and plasticizers.[5][6] It is a potential feedstock for the industrial production of α-ketobutyric acid, a precursor to some amino acids.[9]

SafetyEdit

The LD50 (rats, oral) is 16g/kg.[4]

NotesEdit

  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.

ReferencesEdit

  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. ^ 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.
  3. ^ 1,2-Butanediol, International Chemical Safety Card 0395, Geneva: International Programme on Chemical Safety, March 1996.
  4. ^ a b "Butanediols, Butenediol, and Butynediol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2005. doi:10.1002/14356007.a04_455.
  5. ^ a b 1,2-Butanediol (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, February 1995.
  6. ^ a b US 4596886, Hasegawa, Ryuichi & Kohji Hayashi, "Polyester containing impure 1,2-butanediol", assigned to Mitsubishi Monsanto Chemical Company .
  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. ^ Wurtz, A. (1859), Ann. Chim. Phys., 55: 400CS1 maint: untitled periodical (link).
  9. ^ US 5155263, Imanari, Makoto; Hiroshi Iwane & Masashi Suzuki et al., "Process for preparing α-ketobutyric acid", assigned to Mitsubishi Petrochemical Co., Ltd. .

External linksEdit