Novel and Highly Efficient SnBr2-Catalyzed Esterification Reactions of Fatty Acids: The Notable Anion Ligand Effect

• Published in: Catalysis letters Vol. 143; no. 11; pp. 1240 - 1246
• Main Authors: Ferreira, Arthur Batista, Cardoso, Abiney Lemos, da Silva, Márcio José
• Format: Journal Article
• Language: English
• Published: New York Springer US 01-11-2013; Springer; Springer Nature B.V
• Subjects: Alcohol; Alcohols; Butanol; Catalysis; Catalysts; Catalytic activity; Chemical reactions; Chemistry; Chemistry and Materials Science; Esterification; Ethanol; Exact sciences and technology; Fatty acids; General and physical chemistry; Industrial Chemistry/Chemical Engineering; Lewis acid; Ligands; Oleic acid; Organometallic Chemistry; Physical Chemistry; Softness; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Acid catalysis; Biomass conversion; Fatty acids; Homogeneous catalysis; Ligand effect; Catalytic reaction; Biomass; Conversion; Esterification
• ISSN: 1011-372X; 1572-879X
• DOI: 10.1007/s10562-013-1089-0

In this work, the efficiency of Lewis acid catalysts, SnX
2
(X = F
−
, Cl
−
, Br
−
, or
−
OAc), was investigated on the esterification reactions of fatty acids (i.e., myristic, palmitic, stearic, oleic, linoleic, and linoleic) with different alcohols (i.e., methyl, ethyl, propyl, isopropyl, and butyl alcohol). Tin(II) bromide was the most active catalyst in all reactions studied. We investigated the effects of main reaction parameters, such as catalyst concentration, temperature, and nature of alcohol and fatty acid. The highest activity of SnBr
2
catalyst was discussed in terms of its lower activation energy, higher Lewis acid strength, and higher softness of anionic ligand. Finally, the SnBr
2
catalyst can be easily recovered and reused without loss of catalytic activity.
Graphical Abstract
Effect of the tin catalyst nature on the oleic acid esterification with ethyl alcohol.