Sustainable Process for Production of Azelaic Acid Through Oxidative Cleavage of Oleic Acid
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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.
KeywordsOleic acid Azelaic acid Pelargonic acid Hydrogen peroxide Tungstic acid Sodium hypochlorite
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).
- 4.Brown AC, Goebel CG, Oehlschlaeger HF, Rolfes RP (1957) Method of making azelaic acid. US Patent 2,813,113Google Scholar
- 5.Nojori R, Aoku M, Sato K (2003) Green oxidation with aqueous hydrogen peroxide. Chem Commun 16:1977–1986Google Scholar
- 7.Warwel S, Rüsch gen. Klaas M (1997) Oxidative cleavage of unsaturated fatty acids without ozone. Lipid Technol 9:10–14Google Scholar
- 8.Herrmann AT, Warwel S, Rüsch gen. Klaas M (1977) Production of compounds containing carboxylic acid. German Patent 19,724,736Google Scholar
- 9.Antonelli E, D’Aloisio R, Gambaro M, Fiorani T, Venturello C (1998) Efficient oxidative cleavage of olefins to carboxylic acids with hydrogen peroxide catalyzed by methyltrioctylammonium tetrakis(oxodiperoxotungsto)phosphate(3-) under two-phase conditions. Synthetic aspects and investigation of the reaction course. J Org Chem 63:7190–7206CrossRefGoogle Scholar
- 10.Song HY, Chen J, Tong J (2005) Study on synthesis of azelaic acid by catalytic oxidation using phase transfer catalyst. Huaxue Shiji 27:65–67Google Scholar
- 19.Van Aken K, Strekowski L, Patiny L (2006) EcoScale, a semi-quantitative tool to select an organic preparation based on economical and ecological parameters. Beilstein J Org Chem 3:2Google Scholar
- 20.Lemaire M, Favre-Reguillon A, Paquit B, Claude S, Raoul Y (2011) Method for preparing carboxylic acids by oxidative cleavage of a vicinal diol. WO 2011(107721):A1Google Scholar
- 21.Levey M (1959) Chemistry and technology in ancient Mesopotamia. Elsevier, Amsterdam, pp 33–34Google Scholar