Chemo-enzymatic epoxidation catalyzed by C. antarctica lipase immobilized in microemulsion-based organogels

Zanette, A. F.; Zampakidi, I.; Sotiroudis, Georgios; Zoumpanioti, Maria; Leal, Ivana Corrêa Ramos; Souza, Rodrigo O. M. A. de; Cardozo‐Filho, Lúcio; Xenakis, Aristotelis

doi:10.1016/j.molcatb.2014.05.013

Cited by 17 publications

(15 citation statements)

References 27 publications

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“…They found that the conversion of oleic acid was about 90%. While Zanette et al . studied chemoenzymatic epoxidation of oleic and linoleic acid with hydrogen peroxide using C. antarctica lipase immobilized in organogels which is considered as a semi‐solid catalyst that can be easily isolated from the product.…”

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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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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“…Within this class of enzymes, perhydrolases are able to efficiently catalyze perhydrolysis reactions for the formation of peracids [5,6], but the unusual participation of lipases for global oxidative process has attracted the attention of different research groups in the last decade [5,7,8]. Thus, examples of lipase-mediated epoxidation [9][10][11][12][13][14], Baeyer-Villiger reactions [15][16][17][18][19], perhydrolysis of carboxylic acid and esters [20], sequential Baeyer-Villiger reaction and ring-opening polymerization [21], and also consecutive esterification and Baeyer-Villiger cascade reactions [22] have appeared in the literature, giving access to synthetically useful oxygenated heterocycles through clean and selective transformations under mild reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Lactonization reactions through hydrolase-catalyzed peracid formation. Use of lipases for chemoenzymatic Baeyer–Villiger oxidations of cyclobutanones

González‐Martínez

Rodríguez‐Mata

Méndez-Sánchez

et al. 2015

Journal of Molecular Catalysis B: Enzymatic

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Abstract:A one-pot chemoenzymatic method has been described for the synthesis of -butyrolactones starting from the corresponding ketones through a Baeyer-Villiger reaction.The approach is based on a lipase-catalyzed perhydrolysis for the formation of peracetic acid, which is the responsible for the ketone oxidation. Optimization studies have been performed in the oxidation of cyclobutanone, finding Candida antarctica lipase type B, ethyl acetate and urea-hydrogen peroxide complex as the best system. The relative ratio of these reagents has also been analyzed in depth. This synthetic approach has been successfully extended to a family of 3-substituted cyclobutanones in high substrate concentration, yielding the corresponding lactones with excellent isolated yields and purities, under mild reaction conditions and after a simple extraction protocol.

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“…The peracid then donates oxygen to the double bond, producing an epoxide and regenerating the carboxylic acid. 7 Chemoenzymatic epoxidation is one of the most efficient processes wherein chemical and enzymatic processes are combined together. Mainly, Candida antarctica lipase B (CAL B) has been employed for different organic reactions such as hydrolysis, acylation, esterification, alcoholysis, and epoxidation.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Epoxidation of Limonene Using a Novel Surface-Functionalized Silica Catalyst Derived from Agricultural Waste

Salvi

Yadav

2020

ACS Omega

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Limonene is one of the most important terpenes having wide applications in food and fragrance industries. The epoxide of limonene, limonene oxide, finds important applications as a versatile synthetic intermediate in the chemical industry. Therefore, attempts have been made to synthesize limonene oxide using eco-friendly processes because of stringent regulations on its production. In this regard, we have attempted to synthesize it using a cost-effective and eco-friendly process. Chemoenzymatic epoxidation of limonene to limonene oxide was carried out using in situ generation of peroxy octanoic acid from octanoic acid and H 2 O 2 . In this study, agricultural-waste rice husk ash (RHA)-derived silica was surface-functionalized using (3-aminopropyl) triethoxysilane (APTS), which was cross-linked using glutaraldehyde for immobilization of Candida antarctica lipase B. Furthermore, the immobilized enzyme was entrapped in calcium alginate beads to avoid enzyme leaching. Thus, limonene oxide was prepared using this catalyst under conventional and microwave heating. The microwave irradiation intensifies the process, reducing the reaction time under the same conditions. Maximum conversion of limonene to limonene oxide of 75.35 ± 0.98% was obtained in 2 h at 50 °C using a microwave power of 50 W. In the absence of microwave irradiation, the conventional heating gave 44.6 ± 1.14% conversion in 12 h. The reaction mechanism was studied using the Lineweaver–Burk plot, which follows a ternary complex mechanism with inhibition due to peroxyoctanoic acid (in other words H 2 O 2 ). The prepared catalyst shows high reusability and operational stability up to four cycles.

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Chemo-enzymatic epoxidation catalyzed by C. antarctica lipase immobilized in microemulsion-based organogels

Cited by 17 publications

References 27 publications

Epoxidized vegetable oil and bio‐based materials as PVC plasticizer

Epoxidized vegetable oil and bio‐based materials as PVC plasticizer

Lactonization reactions through hydrolase-catalyzed peracid formation. Use of lipases for chemoenzymatic Baeyer–Villiger oxidations of cyclobutanones

Chemoenzymatic Epoxidation of Limonene Using a Novel Surface-Functionalized Silica Catalyst Derived from Agricultural Waste

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