Chemical transformations in technical cashew nut shell liquid and isolated mixture of cardanols, evaluation of the antioxidant activity and thermal stability of the products for use in pure biodiesel

• Published in: Fuel (Guildford) Vol. 235; pp. 1010 - 1018
• Main Authors: Costa, Kênia de P., de Viveiros, Bárbara M., Schmidt Junior, Marco Aurelio S., Suarez, Paulo A.Z., Rezende, Michelle J.C.
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 01.01.2019; Elsevier BV
• Subjects: Anacardiaceae; Antioxidants; Biodiesel; Biodiesel fuels; Biofuels; Cardanol; Cashew nut shell liquid; Cashews; Chemical synthesis; Derivatives; Diesel; Fluids; NMR; Nuclear magnetic resonance; Organic chemistry; Oxidative stability; Phenols; Stability analysis; t-CNSL; Thermal stability; Transformations; Cardanol; Cashew nut shell liquid; Oxidative stability; Biodiesel; t-CNSL; Thermal stability
• ISSN: 0016-2361; 1873-7153
• DOI: 10.1016/j.fuel.2018.08.111

•Hydrolysis of t-CNSL and cardanol epoxides is reported for the first time.•Methanolysis of t-CNSL and cardanol epoxides is also unpublished.•Oxygenated cardanol derivatives gave remarkable oxidative stability to biodiesel.•A new polyol derived from cardanol proved to be an excellent antioxidant additive.•Oxygenated derivatives had better thermal stability than t-CNSL and cardanol. Biodiesel demand is increasing all over the world. The maintenance of oxidative stability is extremely important to biodiesel market, from the point of view of the quality of the fuel as the economic amount involved. In the present work, we synthesized new antioxidant candidates for biodiesel from chemical transformations in alkyl phenols present in technical cashew nut shell liquid (t-CNSL) and, more specifically, in cardanols isolated from t-CNSL. This raw material is viable, easy accessed and low cost. Five chemical transformations were performed in both t-CNSL and cardanols with yields from 50% to 92%. The starting materials and their respective derivatives were characterized by 1H NMR, 13C NMR and IR. Antioxidant activity and thermal stability of the products were evaluated. The induction period for pure biodiesel was 6.35 h and the addition of 0.5% (w/w) of cardanols increased to 7.37 h. Two products presented excellent antioxidant activity, epoxidized cardanols (4) and hydrolyzed cardanols (6). They increased the induction period to 15.05 h and 18.62 h, respectively. The oxygenated derivatives also showed better thermal stability than the starting materials.