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      Synthesis of biosafe isosorbide dicaprylate ester plasticizer by lipase in a solvent-free system and its sub-chronic toxicity in mice

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          Abstract

          The biosafety isosorbide dicaprylate ester plasticizer was synthesized with bubbling dried air in solvent-free system.

          Abstract

          In this study, biosafe isosorbide dicaprylate ester based plasticizer was prepared using renewable feedstock with lipase in a solvent-free system. Different kinds of water removal methods and some important factors including molar ratio of the substrates, reaction temperature and catalyst loading were investigated. Bubbling dried air was determined to be the most effective water removal method. The activation energy ( E) of hydrolysis and esterification to form di-substituted isosorbide were examined to determine the limiting step in the synthesis of isosorbide dicaprylate ester. The E hydrolysis (25.51 kJ mol −1) was found to be higher than E synthesis (35.65 kJ mol −1), demonstrating that the formation of diester from monoester is the critical step in the process. The lipase can be recycled up to 16 times while 80% diester was maintained. Additionally, the properties of poly(vinyl chloride) PVC blends plasticized with isosorbide ester as secondary plasticizer was studied. The results indicated that the thermal stability of plasticized PVC blends was improved, and the tensile strength was increased. Furthermore, the sub-chronic toxicity study in mice showed that the isosorbide ester was safe, indicating its great potential in industrial applications as a plasticizer.

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          Most cited references27

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          Polymers from renewable 1,4:3,6-dianhydrohexitols (isosorbide, isomannide and isoidide): A review

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            Isosorbide as a Renewable Platform chemical for Versatile Applications-Quo Vadis?

            Isosorbide is a platform chemical of considerable importance for the future replacement of fossil resource-based products. Applications as monomers and building blocks for new polymers and functional materials, new organic solvents, for medical and pharmaceutical applications, and even as fuels or fuel additives are conceivable. The conversion of isosorbide to valuable derivatives by functionalization or substitution of the hydroxyl groups is difficult because of the different configurations of the 2- and 5-positions and the resulting different reactivity and steric hindrance of the two hydroxyl groups. Although a substantial amount of work has been published using exclusively the endo or exo derivatives isomannide and isoidide, respectively, as starting material, a considerable effort is still necessary to transfer and adapt these methods for the efficient conversion of isosorbide. This Minireview deals with all aspects of isosorbide chemistry, which includes its production by catalytic processes, special properties, and chemical transformations for its utilization in biogenic polymers and other applications of interest.
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              Lipases as practical biocatalysts.

              Lipases are the most used enzymes in synthetic organic chemistry, catalyzing the hydrolysis of carboxylic acid esters in aqueous medium or the reverse reaction in organic solvents. Recent methodological advancements regarding practical factors affecting lipase activity and enantioselectivity are reviewed. Select practical examples concerning the use of lipases in the production of chiral intermediates are also highlighted.
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                Author and article information

                Journal
                RSCACL
                RSC Advances
                RSC Adv.
                Royal Society of Chemistry (RSC)
                2046-2069
                2016
                2016
                : 6
                : 15
                : 11959-11966
                Affiliations
                [1 ]National Energy R&D Center for Biorefinery
                [2 ]Beijing Key Laboratory of Bioprocess
                [3 ]College of Biology Science and Technology
                [4 ]Beijing University of Chemical Technology
                [5 ]Beijing 100029
                [6 ]Shandong Jiqing Chemical Co., Ltd
                [7 ]Shandong
                [8 ]PR China
                [9 ]Department of Biology and Pharmacy
                [10 ]Zhejiang Pharmaceutical College
                [11 ]315100 Ningbo
                [12 ]People's Republic of China
                Article
                10.1039/C5RA27537G
                9c5b9e4e-242e-4846-80ba-06a4fc187d53
                © 2016
                History

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