Stability of gamma-valerolactone under neutral, acidic, and basic conditions

Claire Yuet Yan Wong, Alex Wing Tat Choi, Matthew Y. Lui, Bálint Fridrich, Attila K. Horváth*, László T. Mika*, István T. Horváth*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

47 Citations (Scopus)

Abstract

Dry gamma-valerolactone (GVL) is stable for several weeks at 150 °C and its thermal decomposition only proceeds in the presence of appropriate catalysts. Since GVL does not react with water up to 60 °C for several weeks, it could be used as a green solvent at mild conditions. At higher temperatures, GVL reacts with water to form 4-hydroxyvaleric acid (4-HVA) and reaches the equilibrium in a few days at 100 °C. Aqueous solutions of acids (HCl and H2SO4) catalyze the ring opening of GVL even at room temperature, which leads to the establishment of an equilibrium between GVL, water, and 4-HVA. Although the 4-HVA concentration would be below 4 mol% in the presence of acids, it could be higher than the concentration of a reagent or a catalyst precursor, not to mention a catalytically active species. The latter could be especially worrisome as 4-HVA could be an excellent bi- or even a tri-dentate ligand for transition metals. Aqueous solution of bases (NaOH and NH4OH) also catalyzes the reversible ring opening of GVL. While in the case of NaOH, the product is the sodium salt of 4-hydroxyvalerate, the reversible reaction of GVL, with NH4OH results in the formation of 4-hydroxyvaleric amide. The reversible ring opening of (S)-GVL in the presence of HCl or NaOH has no effect on the stability of the chiral center.

Original languageEnglish
Pages (from-to)423-429
Number of pages7
JournalStructural Chemistry
Volume28
Issue number2
Early online date1 Dec 2016
DOIs
Publication statusPublished - Apr 2017
Externally publishedYes

Scopus Subject Areas

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

User-Defined Keywords

  • 4-hydroxy-valeric acid
  • Ammonium hydroxide
  • Equilibrium
  • Gamma-valerolactone
  • Hydrochloric acid
  • Solvents
  • Stability
  • Sulfuric acid
  • Water

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