Journal of Molecular Catalysis B: Enzymatic 81 (2012) 7–11 Contents lists available at SciVerse ScienceDirect Journal of Molecular Catalysis B: Enzymatic jo u rn al hom epa ge: www.elsevier.com/locate/molcatb Epoxidation of oleic acid catalyzed by PSCI-Amano lipase optimized by experimental design Flávia de Abreu Corrêa a,b , Felipe K. Sutili a,b , Leandro S.M. Miranda a , Selma G.F. Leite b , Rodrigo O.M.A. De Souza a , Ivana C.R. Leal a,c,∗ a Biocatalysis and Organic Synthesis Group, Centro de Tecnologia, Bloco A, Universidade Federal do Rio de Janeiro, CEP: 21941-909 Ilha do Fundão, Rio de Janeiro, Brazil b Escola de Química, Laboratório de Microbiologia Industrial, Bloco E, Lab-11, Universidade Federal do Rio de Janeiro, Ilha do Fundão, Rio de Janeiro, Brazil c Curso de Farmácia, Campus Macaé, Pólo Universitário, Universidade Federal do Rio de Janeiro, CEP: 27930-560 Macaé, Rio de Janeiro, Brazil a r t i c l e i n f o Article history: Received 15 September 2011 Received in revised form 12 March 2012 Accepted 16 March 2012 Available online 28 March 2012 Keywords: Central composite design (CCD) Epoxidation Lipase Oleic acid a b s t r a c t The present work focuses on the oleic acid epoxide production by using PSCI Amano Lipase as biocatalyst in the reaction. An experimental design (central composite design – CCD) adopting surface response was applied to this purpose. Reactions were performed in a shaker equipment and different variables were investigated, such as temperature (25–55 ◦ C), enzyme load (10–20 wt% of oleic acid mass), hydrogen peroxide load (0.1–0.2%) and reaction time. PSCI-Amano enzyme showed its best behavior as biocatalyst after 3 h of reaction at 55 ◦ C, 10% enzyme load, 0.2% hydrogen peroxide and, applying 150 rpm as stirring. On these conditions, the epoxide yield was around 88%. © 2012 Elsevier B.V. All rights reserved. 1. Introduction Oleochemicals are hydrocarbons derived from vegetable oils closely related to petrochemicals and well suited for transforma- tions by the chemical industry [1]. Vegetable oils and fatty acids can be used in cosmetics, lubricants, chemical additives, detergents, pharmaceuticals, polymers, and other products [2]. Vegetable oils and their unsaturated fatty acids can be converted into epoxies which are useful intermediates in organic synthesis by participating in many reactions due to the high oxirane ring reactivity [3]. Among their important applications there is the func- tion as plasticizer for polyvinyl chloride (PVC). Plasticizers increase flexibility, workability or distensibility of plastics, hence render- ing them suitable for diverse applications [4]. One of the most important plastics additives currently adopted is the epoxidized soybean oil (ESBO) which has a stable market of approximately 100,000 tons/year [5]. Global demand for plasticizers is projected to grow to 7.6 million tons per year until 2018. The main market is the Asia-Pacific region, with China holding on to its dominating position with 65% share [6]. ∗ Corresponding author. Present address: Rua Aluisio da Silva Gomes no. 50, Uni- versidade Federal do Rio de Janeiro, Campus Macaé, UFRJ, Pólo Universitário, Granja dos Cavaleiros CEP: 27930-560, Macaé, Brazil. Tel.: +55 21 25627807/22 27962563. E-mail address: ivanafarma@yahoo.com.br (I.C.R. Leal). The most used procedure to produce epoxidized fatty acid esters currently consists of two steps involving alcoholysis of triglyc- erides/fatty acids using KOH as catalyst followed by epoxidation of peroxyacetic acid esters or peroxyformic (Scheme 1) [7]. The formation of byproducts occurs due to the high medium acidity. In addition, corrosion and production of large amounts of salts when acids are neutralized are one of the problems associated with this type of reaction [4]. Chemo-enzymatic epoxidation reaction often provides a more selective and environment-friendly alternative to the Prilezhaev epoxidation process [8,9]. In the chemo-enzymatic epoxidation reaction, the enzyme normally catalyzes the peracid formation from the corresponding fatty acid and hydrogen peroxide [10]. Then the peracid spontaneously transfers oxygen to the double bond forming the epoxide (Scheme 2) [11]. Lipases or triacylglycerol hydrolases are an important group of biotechnologically relevant enzymes with immense applications in food, dairy, detergent and pharmaceutical industries. Lipases are also defined as glycerol ester hydrolases that catalyze the hydroly- sis of triglycerides into free fatty acids and glycerol. They can also catalyze esterification, acidolysis, interesterification, alcoholysis and aminolysis in addition to the hydrolytic activity on triglyc- erides. Lipases are produced from microbes, specifically bacteria and, they play a vital role in commercial ventures [12,13]. They represent a broadly employed renewable biocatalyst in lipids trans- formation.Therefore, this work aims at performing the epoxidation of oleic acid using lipase as biocatalyst and the Central composite 1381-1177/$ – see front matter © 2012 Elsevier B.V. All rights reserved. doi:10.1016/j.molcatb.2012.03.011