Physical–Chemical Characteristics of Cutin Separated from Tomato Waste for the Preparation of Bio-lacquers

Abstract

Green chemistry protocols are proposed to produce high-value chemicals from waste tomatoes. Long-chain hydroxy fatty acids (called cutin acids), in particular the 10,16-dihydroxyhexadecanoic acid and its oligomers, could be innovative building-block chemicals for the synthesis of novel bio-resins and lacquers suitable as internal protective coating for metal food packaging. However, these natural compounds are not currently commercially available. This study investigates the possibility of extracting cutin acids from tomato peels without the use of organic solvents and by an efficient, cost-effective, and environmentally safe method amenable to industrial scale-up. The first route investigated was based on alkaline hydrolysis of the tomato cuticle. The second involved the acid free-selective precipitation of cutin. Finally, cutin was isolated by hydrogen peroxide-assisted hydrolysis. GC-MS analysis revealed the main chemical compound isolated by all methods to be 10,16-dihydroxyhexadecanoic acid, the principal component of tomato cutin, with extraction yields ranging from 81 to 96%. Products are different in terms of appearance, solubility, the degree of crosslinking observed and molecular weight, as shown by GPC analysis. Furthermore, the products extracted were characterized by means of FT-IR spectroscopy and thermal analysis. The cutin obtained through alkaline hydrolysis results the best raw material for bio-resin preparation.