Bridging racemic lactate esters with stereoselective polylactic acid using commercial lipase catalysis

Wouwe, Pieter Van; Dusselier, Michiel; Basic, Aurelie; Sels, Bert F.

doi:10.1039/c3gc41457d

Cited by 25 publications

(25 citation statements)

References 107 publications

(136 reference statements)

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“…Candida rugosa lipase (CRL) was found to catalyze the enantioselective hydrolysis of l ‐alkyl lactates in water at ambient conditions, providing easily separated and processable mixtures of l ‐acid and d ‐ester. This route aligns well with chemocatalytic production routes that showed high alkyl lactate yields in alcoholic media . An overview of LA syntheses including enantiomeric separation is presented in Scheme .…”

Section: Lactic‐acid Synthesissupporting

confidence: 56%

“…Alternatively, we propose the route shown in Scheme . Based on our progress in the chemocatalytic conversion of sugars into racemic alkyl lactates, the enzymatic resolution of this racemate and the one‐step synthesis of lactide from LA, we are convinced of the potential of this route. First, the Sn‐Beta zeolite seems especially interesting for producing racemic ethyl lactates from sugars, backed by the reported high catalytic productivity .…”

Section: View On Enantioselectivitymentioning

confidence: 99%

“…First, the Sn‐Beta zeolite seems especially interesting for producing racemic ethyl lactates from sugars, backed by the reported high catalytic productivity . A following enzymatic resolution by enantioselective hydrolysis with Candida rugose lipase is very straightforward and commercially attractive, providing the pure enantiomeric acid for the one‐step zeolite‐catalyzed (liquid‐phase) lactide synthesis. Note that avoiding racemization during lactide synthesis is critical in this scheme, as l ‐ and d ‐LA (or esters) were already produced and separated in a prior enantioselective step.…”

Section: View On Enantioselectivitymentioning

confidence: 99%

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Lactide Synthesis and Chirality Control for Polylactic acid Production

et al. 2016

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Polylactic acid (PLA) is a very promising biodegradable, renewable, and biocompatible polymer. Aside from its production, its application field is also increasing, with use not only in commodity applications but also as durables and in biomedicine. In the current PLA production scheme, the most expensive part is not the polymerization itself but obtaining the building blocks lactic acid (LA) and lactide, the actual cyclic monomer for polymerization. Although the synthesis of LA and the polymerization have been studied systematically, reports of lactide synthesis are scarce. Most lactide synthesis methods are described in patent literature, and current energy-intensive, aselective industrial processes are based on archaic scientific literature. This Review, therefore, highlights new methods with a technical comparison and description of the different approaches. Water-removal methodologies are compared, as this is a crucial factor in PLA production. Apart from the synthesis of lactide, this Review also emphasizes the use of chemically produced racemic lactic acid (esters) as a starting point in the PLA production scheme. Stereochemically tailored PLA can be produced according to such a strategy, giving access to various polymer properties.

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Section: Lactic‐acid Synthesissupporting

confidence: 56%

Section: View On Enantioselectivitymentioning

confidence: 99%

Section: View On Enantioselectivitymentioning

confidence: 99%

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Lactide Synthesis and Chirality Control for Polylactic acid Production

et al. 2016

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“…The use of the racemic mixture in the production of poly(lactic acid) provides a polymer with a low degree of crystallinity and low tensile strength. The pure L-isomer is preferred to produce poly(lactic acid) because it provides a polymer with higher tensile strength and crystallinity and, in this case, the product derived from the fermentative process is preferred (Van Wouve et al, 2013). The racemic mixture, however, has been added to the pure Lisomer during polymerization to change the properties of poly(lactic acid), producing a wide range of physical properties (Datta and Henry, 2006).…”

Section: Resultsmentioning

confidence: 99%

Production of Lactic Acid From Glycerol by Applying an Alkaline Hydrothermal Process Using Homogeneous Catalysts and High Glycerol Concentration

Rodrigues

Maia

Fernandes

2015

Braz. J. Chem. Eng.

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-The production of lactic acid from glycerol by means of the alkaline hydrothermal process was evaluated using high concentrations of glycerol. The operating conditions that influence the hydrothermal process were studied. Temperature (250 -280 °C), catalyst to glycerol molar ratio (0.05 to 0.15), and water to glycerol volumetric ratio (0.8 to 1.5) were evaluated, as well as the use of NaOH and KOH as catalysts. A concentration of lactic acid of 122 g/L was obtained at 260 °C, 0.04 NaOH to glycerol molar ratio, 1.0 water to glycerol volumetric ratio and 3 h of reaction using crude glycerol as raw material. The results showed higher lactic acid concentration and productivity than the fermentative process and the hydrothermal process carried out using low initial glycerol concentration.

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“…However, chirality control is very important if lactide (industrial building block of PLA) production is the target as this will determine the properties of the polymer. Chromatographic methods [22,23], chemical resolution [24] and the combination of the chemo-and biocatalysis [25] are regarded as the means for chiral resolution of racemic lactic acid. Nonetheless, enantioselective chemoproduction of lactic acid from sugars directly has not been reported.…”

Section: Introductionmentioning

confidence: 99%

Chemocatalytic Production of Lactates from Biomass-Derived Sugars

Zhang

et al. 2018

International Journal of Chemical Engineering

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In recent decades, a great deal of attention has been paid to the exploration of alternative and sustainable resources to produce biofuels and valuable chemicals, with aims of reducing the reliance on depleting confined fossil resources and alleviating serious economic and environmental issues. In line with this, lignocellulosic biomass-derived lactic acid (LA, 2-hydroxypropanoic acid), to be identified as an important biomass-derived commodity chemical, has found wide applications in food, pharmaceuticals, and cosmetics. In spite of the current fermentation of saccharides to produce lactic acid, sustainability issues such as environmental impact and high cost derived from the relative separation and purification process will be growing with the increasing demands of necessary orders. Alternatively, chemocatalytic approaches to manufacture LA from biomass (i.e., inedible cellulose) have attracted extensive attention, which may give rise to higher productivity and lower costs related to product work-up. is work presents a review of the state-of-the-art for the production of LA using homogeneous, heterogeneous acid, and base catalysts, from sugars and real biomass like rice straw, respectively. Furthermore, the corresponding bio-based esters lactate which could serve as green solvents, produced from biomass with chemocatalysis, is also discussed. Advantages of heterogeneous catalytic reaction systems are emphasized. Guidance is suggested to improve the catalytic performance of heterogeneous catalysts for the production of LA.

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Bridging racemic lactate esters with stereoselective polylactic acid using commercial lipase catalysis

Cited by 25 publications

References 107 publications

Lactide Synthesis and Chirality Control for Polylactic acid Production

Lactide Synthesis and Chirality Control for Polylactic acid Production

Production of Lactic Acid From Glycerol by Applying an Alkaline Hydrothermal Process Using Homogeneous Catalysts and High Glycerol Concentration

Chemocatalytic Production of Lactates from Biomass-Derived Sugars

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