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Journal of the American Oil Chemists' Society

, Volume 92, Issue 11–12, pp 1701–1707 | Cite as

Sustainable Process for Production of Azelaic Acid Through Oxidative Cleavage of Oleic Acid

  • Vincenzo Benessere
  • Maria E. Cucciolito
  • Augusta De Santis
  • Martino Di Serio
  • Roberto Esposito
  • Francesco Ruffo
  • Rosa Turco
Original Paper

Abstract

This work describes two sustainable methods for production and purification of azelaic acid (AA) to replace the current process of ozonolysis of oleic acid (OA). The first proceeds in two steps, coupling smooth oxidation of OA to 9,10-dihydroxystearic acid (DSA) with subsequent oxidative cleavage by sodium hypochlorite. An alternative methodology is also proposed, using a chemocatalytic system consisting of H2O2/H2WO4 for direct oxidative cleavage of the double bond of OA at 373 K. A convenient technique for separation and purification of azelaic acid is also proposed.

Keywords

Oleic acid Azelaic acid Pelargonic acid Hydrogen peroxide Tungstic acid Sodium hypochlorite 

Notes

Acknowledgments

The authors warmly thank Prof. Thierry Ollevier (Université Laval, Canada) for helpful discussions. The authors thank MIUR (Progetto Rebiochem—Cluster 2012) for financial support. The authors also thank Solvay (Rosignano, Italy) for a generous loan of hydrogen peroxide (60 % v/v).

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Copyright information

© AOCS 2015

Authors and Affiliations

  • Vincenzo Benessere
    • 1
    • 2
  • Maria E. Cucciolito
    • 1
    • 2
  • Augusta De Santis
    • 1
  • Martino Di Serio
    • 1
    • 2
  • Roberto Esposito
    • 1
    • 2
  • Francesco Ruffo
    • 1
    • 2
  • Rosa Turco
    • 1
    • 2
  1. 1.Dipartimento di Scienze ChimicheUniversità di Napoli “Federico II”NaplesItaly
  2. 2.Consorzio Interuniversitario di Reattività Chimica e Catalisi (CIRCC)BariItaly

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