Enzymatic epoxidation of soybean oil in the presence of perbutyric acid

Chen, Jingnan; Zhou, Jinfen; Liu, Wei; Bi, Yanlan; Peng, Dan

doi:10.1007/s11696-017-0206-8

Cited by 9 publications

(6 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…397 N435 epoxidation of acid sunflower oil was improved by introducing butyric acid as an active oxygen carrier (reaching an oxirane conversion of 96.4 ± 3.0%). 398,399 Finally, ultrasonic irradiation was used for enhancing N435 activity in the epoxidation of soybean oil. 400 A relative percentage conversion to oxirane oxygen of 91.22% was achieved within 5 h. The lipase was reused six times to produce epoxidized soybean oil.…”

Section: Catalysis Science and Technology Mini Reviewmentioning

confidence: 99%

Novozym 435: the “perfect” lipase immobilized biocatalyst?

Ortíz

Ferreira

Barbosa

et al. 2019

Catal. Sci. Technol.

471

360

View full text Add to dashboard Cite

show abstract

Section: Catalysis Science and Technology Mini Reviewmentioning

confidence: 99%

Novozym 435: the “perfect” lipase immobilized biocatalyst?

Ortíz

Ferreira

Barbosa

et al. 2019

Catal. Sci. Technol.

471

360

View full text Add to dashboard Cite

show abstract

“…Chemoenzymatic epoxidation is the reaction which combines the flexibility of chemical epoxidation and the exquisite selective properties for enzymes in reaction . The reaction mechanism of chemoenzymatic epoxidation consists of two consequent reactions: the first is the conversion of unsaturated fatty acids or esters, where the enzyme reacts with hydrogen peroxide to form unsaturated peroxy carboxylic acid.…”

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

135

View full text Add to dashboard Cite

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.

show abstract

“…To answer the question of whether the most efficient way to produce epoxides, in terms of catalytic performance, is the enzymatic approach via direct epoxidation or the chemical synthesis using peroxy acids, the Prilezhaev reaction was studied in chloroform as proposed in previous studies . A short peroxy acid, perbutyric acid, was used as a model, as suggested in previous works. , The reaction goes through what is called a butterfly mechanism, as depicted in Figure . The study of the reaction at the B3LYP/MM level shows that it occurs in a single step where the transfer of the proton H 1 toward carbonyl oxygen O 1 of the peroxy acid takes place concomitant with the peroxy acid oxygen O 3 attack on carbon of the alkene, the closing of the epoxide ring between C 2 –C 3 of 2-butenal and the formation of butyric acid.…”

Section: Resultsmentioning

confidence: 99%

“…66 A short peroxy acid, perbutyric acid, was used as a model, as suggested in previous works. 67,68 The reaction goes through what is called a butterfly mechanism, as depicted in Figure 8. The study of the reaction at the B3LYP/MM level shows that it occurs in a single step where the transfer of the proton H 1 toward carbonyl oxygen O 1 of the peroxy acid takes place concomitant with the peroxy acid oxygen O 3 attack on carbon of the alkene, the closing of the epoxide ring between C 2 −C 3 of 2-butenal and the formation of butyric acid.…”

Section: Substrate−enzyme Bindingmentioning

confidence: 99%

Computational Studies Suggest Promiscuous Candida antarctica Lipase B as an Environmentally Friendly Alternative for the Production of Epoxides

Galmés

Świderek

Moliner

2021

J. Chem. Inf. Model.

View full text Add to dashboard Cite

Environmentally friendly processes are nowadays a trending topic to get highly desired chemical compounds and, in this sense, the use of enzyme-catalyzed routes is becoming a promising alternative to traditional synthetic methods. In the present paper, a hybrid quantum mechanics/molecular mechanics (QM/MM) computational study on the epoxidation of alkenes catalyzed by the Ser105Ala variant of the promiscuous Candida antarctica lipase B (CALB) is presented in an attempt to search for alternative paths to get useful intermediates in industries. The catalyzed reaction, described at the atomistic level with a model of the full solvated in a box of water molecules, is compared with the alternative epoxidation of alkenes by peroxy acids in chloroform. Freeenergy profiles obtained at the density functional theory (DFT)/MM level show how Ser105Ala CALB is capable of epoxide short alkenes in a twostep process with free-energy barriers, in agreement with available experimental data, that are significantly lower than those of the single-step reaction in solution. The possible (R)-enantioselectivity dictated by the binding step, explored by means of alchemical QM/MM free-energy perturbation (FEP) methods, and the preference for the (S)-enantiomer derived from the free-energy landscape of the chemical steps would cancel out, thus predicting the lack of enantioselectivity experimentally observed. In general, our results provide general information on the molecular mechanism employed by a highly promiscuous enzyme, with potential applications in biotechnology.

show abstract

Enzymatic epoxidation of soybean oil in the presence of perbutyric acid

Cited by 9 publications

References 19 publications

Novozym 435: the “perfect” lipase immobilized biocatalyst?

Novozym 435: the “perfect” lipase immobilized biocatalyst?

Epoxidized vegetable oil and bio‐based materials as PVC plasticizer

Computational Studies Suggest Promiscuous Candida antarctica Lipase B as an Environmentally Friendly Alternative for the Production of Epoxides

Contact Info

Product

Resources

About