1,2-Butanediol

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1,2-Butanediol
Molecular forula of 1,2-Butanediol
Butanediol molecule
Names
Preferred 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
EC Number
  • 209-527-2
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[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
Std enthalpy of
formation (ΔfH⦵298)
 −532.8 kJ/mol [2]
Std enthalpy of
combustion (ΔcH⦵298)
 −2479 kJ/mol
Hazards[3]
Flash point 90 °C (194 °F; 363 K)
Safety data sheet (SDS) ICSC 0395
Related compounds
Related butanediols
 1,3-Butanediol
1,4-Butanediol
2,3-Butanediol
Related compounds
 Ethylene glycol
Propylene glycol

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).
☒N  (what is checkY☒N ?)
Infobox references

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.

Preparation[]

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]

Applications[]

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]

Safety[]

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

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.

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. ^ 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 & Hayashi, Kohji, "Polyester containing impure 1,2-butanediol", published 1986-06-24, assigned to Mitsubishi Monsanto Chemical Company .
  7. ^ US 4966658, Berg, Lloyd, "Recovery of ethylene glycol from butanediol isomers by azeotropic distillation", published 1990-10-30 . US 5423955, Berg, Lloyd, "Separation of propylene glycol from 1,2-butanediol by azeotropic distillation", published 1995-06-13 .
  8. ^ Wurtz, A. (1859), "Mémoire sur les glycols ou alcools diatomique" [Dissertation on glycols, or diatomic alcohols], Ann. Chim. Phys., 55: 400.
  9. ^ US 5155263, Imanari, Makoto; Iwane, Hiroshi & Suzuki, Masashi et al., "Process for preparing α-ketobutyric acid", published 1992-10-13, assigned to Mitsubishi Petrochemical Co., Ltd. .

External links[]

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