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1,2-Butanediol

α-Butylene glycol 1,4-Butanediol 2,3-Butanediol Propylene glycol 2-Hydroxybutyraldehyde 2-Hydroxybutyric acid α-Ketobutyric acid

1,2-Butanediol is the organic compound with the formula HOCH(HO)CHCHCH. 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

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

It is produced industrially by hydration of 1,2-epoxybutane.

:[[File:Industrial_synthesis_of_1,2-butanediol.svg|378x378px]] This process requires a ten- to twenty-fold excess of water to suppress the formation of polyethers. Depending on the amount of excess water, the selectivity varies from 70 to 92%. Sulfuric acid or strongly acidic ion exchange resins may be used as catalysts, which allows the reaction to occur under 160 °C and at slightly above atmospheric pressure.

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

It can also be obtained from the dihydroxylation of but-1-ene by OsO4.

Applications

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

Safety

The (rats, oral) is 16g/kg.

Notes

References

References

  1. {{RubberBible62nd
  2. (1937). "Chaleurs de formation de l'oxyde d'ethylene, de l'ethanediol et de quelques homologues". [[Bull. Soc. Chim. Fr.]].
  3. {{ICSC-ref. 03. 95. (March 1996.)
  4. Wurtz, A.. (1859). "Mémoire sur les glycols ou alcools diatomique". [[Ann. Chim. Phys.]].
  5. (2005). "Butanediols, Butenediol, and Butynediol".
  6. {{SIDS-ref. (February 1995.)
  7. (2019-07-23). "Butanediols, Butenediol, and Butynediol". Wiley-VCH Verlag GmbH & Co. KGaA.
  8. "Polyester containing impure 1,2-butanediol".
  9. "Recovery of ethylene glycol from butanediol isomers by azeotropic distillation".
  10. "Process for preparing α-ketobutyric acid".
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alkanediols vicinal-diols substances-discovered-in-the-19th-century butane
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