Enzymatic Synthesis of a Diene Ester Monomer Derived from Renewable Resource

• Published in: Applied biochemistry and biotechnology Vol. 189; no. 3; pp. 745 - 759
• Main Authors: de Oliveira Romera, Cristian, de Oliveira, Débora, Sayer, Claudia, de Araújo, Pedro Henrique Hermes
• Format: Journal Article
• Language: English
• Published: New York Springer US 01-11-2019; Springer Nature B.V
• Subjects: Biocatalysis; Biochemistry; Biotechnology; Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry Techniques, Synthetic; Chloroform; Enzymatic synthesis; Enzymes; Esterification; Esters - chemical synthesis; Esters - chemistry; Free radical polymerization; Fungal Proteins - metabolism; Green Chemistry Technology; Kinetics; Lipase - metabolism; Metathesis; Methacrylates - chemistry; Monomers; Polyhydroxyethyl methacrylate; Polymerization; Polymers; Purification; Raw materials; Reaction kinetics; Reaction time; Renewable resources; Substitution reactions; Substrates; Sustainable yield; Undecylenic Acids - chemistry; HEMA; Novozym 435; Lipase; Esterification; 10-undecenoic acid; Diene ester monomer
• ISSN: 0273-2289; 1559-0291
• DOI: 10.1007/s12010-019-03043-9

The total or partial substitution of fossil raw materials by biobased materials from renewable resources is one of the great challenges of our society. In this context, the reaction under mild condition as enzyme-catalyzed esterification was applied to investigate the esterification of the biobased 10-undecenoic acid with 2-hydroxyethyl methacrylate (HEMA) to obtain a new diene ester monomer. The environmentally friendly enzymatic reaction presented up to 100% of conversion; moreover, the production of possible by-products was minimized controlling reaction time and amount of enzyme. Furthermore, the presence of chloroform was evaluated during the enzymatic reactions and despite high conversions with higher enzyme concentration, the solvent-free system showed fast kinetics even with 1.13 U/g substrates. In addition, the commercial immobilized lipases Novozym 435 and NS 88011 could be applied for up to 10 cycles keeping conversions about 90%. The scale-up of the reaction was possible and a purification procedure was applied in order to isolate the diene ester monomer 2-(10-undecenoyloxy)ethyl methacrylate, preserving its double bonds, which could allow a potential use of this product in the synthesis of new renewable polymers through techniques as metathesis, thiol-ene, or free-radical polymerization.