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1,2-Butanediol

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1,2-Butanediol
Molecular forula of 1,2-Butanediol
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 Edit this at Wikidata
RTECS number
  • EK0380000
UNII
  • InChI=1S/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3 checkY
    Key: BMRWNKZVCUKKSR-UHFFFAOYSA-N checkY
  • InChI=1/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3
    Key: BMRWNKZVCUKKSR-UHFFFAOYAV
  • OCC(O)CC
  • CCC(CO)O
Properties
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)
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 [4]
−2479 kJ/mol
Hazards
Flash point 90 °C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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 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

  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. Vol. A1. Weinheim: Wiley-VCH. p. VA4 461. ISBN 978-3527306732..
  3. ^ a b 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 {{citation}}: Missing or empty |title= (help).
  7. ^ a b Polyester containing impure 1,2-butanediol, 1986 {{citation}}: Unknown parameter |assignee= ignored (help); Unknown parameter |country-code= ignored (help); Unknown parameter |inventor1-first= ignored (help); Unknown parameter |inventor1-last= ignored (help); Unknown parameter |inventor2-first= ignored (help); Unknown parameter |inventor2-last= ignored (help); Unknown parameter |patent-number= ignored (help).
  8. ^ Recovery of ethylene glycol from butanediol isomers by azeotropic distillation, 1990 {{citation}}: Unknown parameter |country-code= ignored (help); Unknown parameter |inventor-first= ignored (help); Unknown parameter |inventor-last= ignored (help); Unknown parameter |patent-number= ignored (help). Separation of propylene glycol from 1,2-butanediol by azeotropic distillation, 1995 {{citation}}: Unknown parameter |country-code= ignored (help); Unknown parameter |inventor-first= ignored (help); Unknown parameter |inventor-last= ignored (help); Unknown parameter |patent-number= ignored (help).
  9. ^ Process for preparing α-ketobutyric acid, 1992 {{citation}}: Unknown parameter |assignee= ignored (help); Unknown parameter |country-code= ignored (help); Unknown parameter |inventor1-first= ignored (help); Unknown parameter |inventor1-last= ignored (help); Unknown parameter |inventor2-first= ignored (help); Unknown parameter |inventor2-last= ignored (help); Unknown parameter |inventor3-first= ignored (help); Unknown parameter |inventor3-last= ignored (help); Unknown parameter |inventor4-first= ignored (help); Unknown parameter |inventor4-last= ignored (help); Unknown parameter |patent-number= ignored (help).
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