Towards regioselective enzymatic hydrolysis and glycerolysis of tricaprylin in miniemulsion and the direct preparation of polyurethane from the hydrolysis products

Lima, Ana Paula Dantas de; Aschenbrenner, Eugen M.; Oliveira, Sâmeque do Nascimento; Doucet, Jean-Baptiste; Weiss, Clemens K.; Ziener, Ulrich; Fonseca, Luís P.; Ricardo, Nágila M.P.S.; Freitas, Liane Lucy de Lucca; Petzhold, César Liberato; Landfester, Katharina

doi:10.1016/j.molcatb.2013.10.013

Cited by 12 publications

(8 citation statements)

References 60 publications

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“…Aqueous miniemulsions (oil-in-water (o/w)) are systems characterized by oil droplets in the range between 200 and 300 nm, dispersed in a continuous water phase, which contributes to about 80% (w/w) [37]. Several reactions have been carried out in miniemulsion systems using enzymes by our research group, such as high-added-value ester synthesis using various lipases and cutinases [38][39][40], resolution of enantiomers with Candida antarctica lipase B (CALB) [41], triglyceride hydrolysis, and glycerolysis with Pseudomonas cepacia [42]. More recently, aldol reactions were performed using Rhizopus arrhizus lipase [43].…”

Section: Introductionmentioning

confidence: 99%

Biodegradable Polyester Synthesis in Renewed Aqueous Polycondensation Media: The Core of the New Greener Polymer-5B Technology

2021

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An innovative enzymatic polycondensation of dicarboxylic acids and dialcohols in aqueous polymerization media using free and immobilized lipases was developed. Various parameters (type of lipases, temperature, pH, stirring type and rate, and monomer carbon chain length) of the polycondensation in an oil-in-water (o/w) miniemulsion (>80% in water) were evaluated. The best results for polycondensation were achieved with an equimolar monomer concentration (0.5 M) of octanedioic acid and 1,8-octanediol in the miniemulsion and water, both at initial pH 5.0 with immobilized Pseudozyma antarctica lipase B (PBLI). The synthesized poly(octamethylene suberate) (POS) in the miniemulsion is characterized by a molecular weight of 7800 g mol−1 and a conversion of 98% at 45 °C after 48 h of polycondensation in batch operation mode. A comparative study of polycondensation using different operation modes (batch and fed-batch), stirring type, and biocatalyst reutilization in the miniemulsion, water, and an organic solvent (cyclohexane:tetrahydrofuran 5:1 v/v) was performed. Regarding the polymer molecular weight and conversion (%),batch operation mode was more appropriate for the synthesis of POS in the miniemulsion and water, and fed-batch operation mode showed better results for polycondensation in the organic solvent. The miniemulsion and water used as polymerization media showed promising potential for enzymatic polycondensation since they presented no enzyme inhibition for high monomer concentrations and excellent POS synthesis reproducibility. The PBLI biocatalyst presented high reutilization capability over seven cycles (conversion > 90%) and high stability equivalent to 72 h at 60 °C on polycondensation in the miniemulsion and water. The benefits of polycondensation in aqueous media using an o/w miniemulsion or water are the origin of the new concept strategy of the green process with a green product that constitutes the core of the new greener polymer-5B technology.

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Section: Introductionmentioning

confidence: 99%

Biodegradable Polyester Synthesis in Renewed Aqueous Polycondensation Media: The Core of the New Greener Polymer-5B Technology

2021

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“…High-performance liquid chromatography (HPLC, Thermo Scientific Ultimate 3000) was used in the quantification of TAG, DAG MAG and FFA according procedure described by Lima et al [20].…”

Section: Sample Analysismentioning

confidence: 99%

Kinetic Study of Liquid Lipase-catalyzed Glycerolysis From Olive Oil Using Lipozyme TL 100L

Oliveira¹,

Finco²,

Fiametti³

et al. 2021

Preprint

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Monoacylglycerol (MAG) and diacylglycerol (DAG) are two natural components found in most edible oils and fats. Conventional synthesis of MAG and DAG is usually conducted by glycerolysis of triacylglycerol (TAG) at high temperatures (above 200 °C) in the presence of an alkaline catalyst. In this work, the synthesis of MAG and DAG using enzymatic glycerolysis of olive oil was investigated using Tween 80 as surfactant, n-butanol as co-surfactant and the novel lipase in liquid formulation Lipozyme TL 100L as catalyst. Experimental design was used to evaluate the effect of enzyme load and reaction temperature on the feedstock conversion. Enzyme load and system temperature were significant variables in the statistical design and the best condition was found at 35 °C, 7.5 vol% of Lipozyme TL 100 and 2:1 molar ratio (glycerolysis:oil) with conversion of TAG at approximately 98 % after 2 h of process. A mathematical model based on the Ping-Pong Bi-Bi mechanism was used to describe the reaction kinetics. The model adequately described the behavior of the system and can be a useful tool for the design of reactors in larger scales.

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“…Fatty acids can be derived from vegetable oils by hydrolysis (Mutlu and Meier, 2010 ; De Lima et al, 2013 ). They have been intensively studied for the use as building blocks in polymer science and derivatized to a variety of functional monomers.…”

Section: Polymers and Monomers From Natural Resourcesmentioning

confidence: 99%

Nanoparticles from renewable polymers

Wurm

Weiss

2014

Front. Chem.

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The use of polymers from natural resources can bring many benefits for novel polymeric nanoparticle systems. Such polymers have a variety of beneficial properties such as biodegradability and biocompatibility, they are readily available on large scale and at low cost. As the amount of fossil fuels decrease, their application becomes more interesting even if characterization is in many cases more challenging due to structural complexity, either by broad distribution of their molecular weights (polysaccharides, polyesters, lignin) or by complex structure (proteins, lignin). This review summarizes different sources and methods for the preparation of biopolymer-based nanoparticle systems for various applications.

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Towards regioselective enzymatic hydrolysis and glycerolysis of tricaprylin in miniemulsion and the direct preparation of polyurethane from the hydrolysis products

Cited by 12 publications

References 60 publications

Biodegradable Polyester Synthesis in Renewed Aqueous Polycondensation Media: The Core of the New Greener Polymer-5B Technology

Biodegradable Polyester Synthesis in Renewed Aqueous Polycondensation Media: The Core of the New Greener Polymer-5B Technology

Kinetic Study of Liquid Lipase-catalyzed Glycerolysis From Olive Oil Using Lipozyme TL 100L

Nanoparticles from renewable polymers

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