Chemo-enzymatic epoxidation of sunflower oil methyl esters

Schneider, Rosana de Cássia de Souza; Lara, Luciano Roni Silva; Bitencourt, Thiago Bergler; Nascimento, Maria da Graça; Nunes, Marta Regina dos Santos

doi:10.1590/s0103-50532009000800013

Cited by 37 publications

(16 citation statements)

References 18 publications

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“…159 Therefore, they are safer than chemical epoxidation and they meet SHE (safety, health, and environment) standards. 160 However, lipase catalyzed processes oen take long reaction times, 121,160,161 which can be reduced by the use of sonication. 47 The hydrogen peroxide to unsaturation ratio, temperature, enzyme loading, stirring speed, reaction time, amount of fatty acid and solvents are the major players in the high conversion and selectivity of the epoxidized product.…”

Section: Enzymatic Methodsmentioning

confidence: 99%

Catalytic developments in the epoxidation of vegetable oils and the analysis methods of epoxidized products

et al. 2019

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Section: Enzymatic Methodsmentioning

confidence: 99%

Catalytic developments in the epoxidation of vegetable oils and the analysis methods of epoxidized products

et al. 2019

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“…The outcome from this study was that the solvent polarity has an undesired effect on lipase stability because of the contest between the enzymatic protein and the solvent for water . Accordingly, hydrophobic solvents are not preferred to be used for lipase catalyzed reactions and to open the way towards many intermediate polarities compounds which could be used as solvents . De Abrêu et al .…”

Section: Oleochemicals Overviewmentioning

confidence: 99%

Epoxidized vegetable oil and bio‐based materials as PVC plasticizer

Hosney

Nadiem

Ashour

et al. 2018

J of Applied Polymer Sci

134

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Phthalate esters received a considerable attention owing to its various applications and the harmful health effects resulting from phthalate exposure; thus, finding an alternative to phthalate derivatives became a necessity. Phthalate esters are commonly used as plasticizer in polymer formulation; in particular for poly(vinyl chloride) (PVC) formulation. According to the researches in the last 18 years, epoxidized vegetable oils are one of the alternatives that are strongly encouraged to substitute phthalate esters since they were proven to be valid in various applications, eco-friendly and sustainable resource. However, most of the production practices for epoxidized vegetable oil are via conventional epoxidation that concentrates on a catalyst that is homogeneous and non-reusable. This type of catalyst, however, causes several problems later in the process. Therefore, the selective epoxidation of vegetable oils process requires new catalytic systems that are more aligned with the green chemistry principles. This article reviews the harmful health effects associated with the exposure to phthalate esters products, explains the usage of oleochemicals resources as a substitute to phthalate esters and describes different approaches for the epoxidation of vegetable oils. Finally, it draws attention to the usage of epoxy and bio-based compounds as plasticizers in PVC manufacturing.

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“…1. In the last decade, different epoxidation processes have been successfully used to obtain epoxidized vegetable oils (EVOs) being soybean oil (SBO) and linseed oil (LO) the most used with difference but it has been reported the use of sunflower oil [8,9] wheat oil [10] castor oil [11] or fish oil [12] with attracting uses as industrial plasticizers. The suitability of a vegetable oil to be subjected to an epoxidation process is directly related to the total content on unsaturated fatty acids being the iodine index a high representative value for the presence of unstaurations which can be converted into oxirane rings.…”

Section: -Introductionmentioning

confidence: 99%

Development of environmentally friendly composite matrices from epoxidized cottonseed oil

Carbonell‐Verdu

Bernardi

Garcia‐Garcia

et al. 2015

European Polymer Journal

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The continuous rise in oil prices has led to the use of other ways to obtain polymer materials. This paper proposes a methodology to obtain a thermosetting resin from cottonseed oil by epoxidation process. The cottonseed oil contains as most representative fatty acids: 52.5% of linoleic acid (C18: 2), 23.9% of palmitic acid (C16: 0) and 17.6% of oleic acid (C18: 1); the real iodine index, which is indicative of the number of double bonds, has a value of 107. Epoxidized cottonseed oil (ECSO) has been successfully obtained using conventional epoxidation process with hydrogen peroxide, acetic acid and sulfuric acid, maintaining a constant temperature of 70 ºC with homogeneous magnetic stirring. Average oxirane oxygen content (OOC) of 5.32% can be obtained by conventional epoxidation process which represents a yield over 83%. The epoxidized oil has been crosslinked with mixtures of two cyclic anhydrides to tailor different properties on final crosslinked thermosetting resins: on the one hand, methyl nadic anhydride (MNA) which is characterized by a rigid molecular structure and on the other hand, dodecenylsuccinic anhydride (DDSA) with a long side chain that can confer flexibility. The crosslinking process has been followed by dynamic differential scanning calorimetry (DSC), ionic mobility and oscillatory rheometry (OR) as well as gel time determination.The effect of the hardener mixture (wt. % DDSA:MNA) on mechanical performance of cured materials has been followed by flexural and impact tests as well as the evolution of the storage modulus (G') by dynamic mechanical analysis (DMA) in torsion mode. By selecting the appropriate hardener mixture, it is possible to obtain crosslinked materials with different properties ranging from

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Chemo-enzymatic epoxidation of sunflower oil methyl esters

Cited by 37 publications

References 18 publications

Catalytic developments in the epoxidation of vegetable oils and the analysis methods of epoxidized products

Catalytic developments in the epoxidation of vegetable oils and the analysis methods of epoxidized products

Epoxidized vegetable oil and bio‐based materials as PVC plasticizer

Development of environmentally friendly composite matrices from epoxidized cottonseed oil

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