The combined use of ultrasound and molecular sieves improves the synthesis of ethyl butyrate catalyzed by immobilized Thermomyces lanuginosus lipase

•Ultrasound energy was used as mixing system in the esterification reaction of flavor esters.•Enzyme stability in butyric acid was improved under ultrasound-assisted reaction.•The use of molecular sieves improved the yield 1.5-times.•The combined use of molecular sieves and ultrasound increased the...

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Veröffentlicht in:Ultrasonics sonochemistry 2015-01, Vol.22, p.89-94
Hauptverfasser: Paludo, Natalia, Alves, Joana S., Altmann, Cintia, Ayub, Marco A.Z., Fernandez-Lafuente, Roberto, Rodrigues, Rafael C.
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container_issue
container_start_page 89
container_title Ultrasonics sonochemistry
container_volume 22
creator Paludo, Natalia
Alves, Joana S.
Altmann, Cintia
Ayub, Marco A.Z.
Fernandez-Lafuente, Roberto
Rodrigues, Rafael C.
description •Ultrasound energy was used as mixing system in the esterification reaction of flavor esters.•Enzyme stability in butyric acid was improved under ultrasound-assisted reaction.•The use of molecular sieves improved the yield 1.5-times.•The combined use of molecular sieves and ultrasound increased the operational stability. In this work, the combined use of ultrasound energy and molecular sieves was investigated for the synthesis of ethyl butyrate, ester with mango and banana notes, catalyzed by the immobilized lipase from Thermomyces lanuginosus (Lipozyme TL-IM). Initially, the best concentrations of biocatalysts (35%) and butyric acid (0.7M) were tested using ultrasound as an alternative to mechanical agitation. The amount of acid in the reaction could be increased by 2-fold when compared to previous works where mechanical agitation was used. In the next step, substrate molar ratio and reaction temperature were optimized and the best conditions were at their lowest levels: 1:1 (acid:alcohol), and 30°C, reaching 61% of conversion in 6h. Molecular sieves (3Å) were added to optimized reaction medium in order to remove the formed water and improve the maximum yield. The reaction yield increased 1.5 times, reaching 90% of conversion in 6h, when 60mg of molecular sieves per mmol of butyric acid was used. Finally, the reuse of Lipozyme TL-IM for the ultrasound-assisted synthesis of ethyl butyrate was verified for 10 batches, without any appreciable loss of activity, whereas in systems using mechanical agitation, the biocatalyst was completely inactivated after 5 batches. These results suggest that the combined use of ultrasound and molecular sieves greatly improve esterification reactions by stabilizing the enzyme and increasing yields.
doi_str_mv 10.1016/j.ultsonch.2014.05.004
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In this work, the combined use of ultrasound energy and molecular sieves was investigated for the synthesis of ethyl butyrate, ester with mango and banana notes, catalyzed by the immobilized lipase from Thermomyces lanuginosus (Lipozyme TL-IM). Initially, the best concentrations of biocatalysts (35%) and butyric acid (0.7M) were tested using ultrasound as an alternative to mechanical agitation. The amount of acid in the reaction could be increased by 2-fold when compared to previous works where mechanical agitation was used. In the next step, substrate molar ratio and reaction temperature were optimized and the best conditions were at their lowest levels: 1:1 (acid:alcohol), and 30°C, reaching 61% of conversion in 6h. Molecular sieves (3Å) were added to optimized reaction medium in order to remove the formed water and improve the maximum yield. The reaction yield increased 1.5 times, reaching 90% of conversion in 6h, when 60mg of molecular sieves per mmol of butyric acid was used. Finally, the reuse of Lipozyme TL-IM for the ultrasound-assisted synthesis of ethyl butyrate was verified for 10 batches, without any appreciable loss of activity, whereas in systems using mechanical agitation, the biocatalyst was completely inactivated after 5 batches. 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In this work, the combined use of ultrasound energy and molecular sieves was investigated for the synthesis of ethyl butyrate, ester with mango and banana notes, catalyzed by the immobilized lipase from Thermomyces lanuginosus (Lipozyme TL-IM). Initially, the best concentrations of biocatalysts (35%) and butyric acid (0.7M) were tested using ultrasound as an alternative to mechanical agitation. The amount of acid in the reaction could be increased by 2-fold when compared to previous works where mechanical agitation was used. In the next step, substrate molar ratio and reaction temperature were optimized and the best conditions were at their lowest levels: 1:1 (acid:alcohol), and 30°C, reaching 61% of conversion in 6h. Molecular sieves (3Å) were added to optimized reaction medium in order to remove the formed water and improve the maximum yield. The reaction yield increased 1.5 times, reaching 90% of conversion in 6h, when 60mg of molecular sieves per mmol of butyric acid was used. Finally, the reuse of Lipozyme TL-IM for the ultrasound-assisted synthesis of ethyl butyrate was verified for 10 batches, without any appreciable loss of activity, whereas in systems using mechanical agitation, the biocatalyst was completely inactivated after 5 batches. These results suggest that the combined use of ultrasound and molecular sieves greatly improve esterification reactions by stabilizing the enzyme and increasing yields.</description><subject>Ascomycota - enzymology</subject><subject>Biocatalysis</subject><subject>Butyrates - chemical synthesis</subject><subject>Butyrates - chemistry</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Chemistry Techniques, Synthetic - methods</subject><subject>Enzymes, Immobilized - chemistry</subject><subject>Enzymes, Immobilized - metabolism</subject><subject>Esterification</subject><subject>Esterification reactions</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Ion Exchange Resins - chemistry</subject><subject>Lipase - chemistry</subject><subject>Lipase - metabolism</subject><subject>Lipases</subject><subject>Lipozyme TL-IM</subject><subject>Molecular sieves</subject><subject>Operational stability</subject><subject>Physical chemistry of induced reactions (with radiations, particles and ultrasonics)</subject><subject>Temperature</subject><subject>Theory of reactions, general kinetics. 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In this work, the combined use of ultrasound energy and molecular sieves was investigated for the synthesis of ethyl butyrate, ester with mango and banana notes, catalyzed by the immobilized lipase from Thermomyces lanuginosus (Lipozyme TL-IM). Initially, the best concentrations of biocatalysts (35%) and butyric acid (0.7M) were tested using ultrasound as an alternative to mechanical agitation. The amount of acid in the reaction could be increased by 2-fold when compared to previous works where mechanical agitation was used. In the next step, substrate molar ratio and reaction temperature were optimized and the best conditions were at their lowest levels: 1:1 (acid:alcohol), and 30°C, reaching 61% of conversion in 6h. Molecular sieves (3Å) were added to optimized reaction medium in order to remove the formed water and improve the maximum yield. The reaction yield increased 1.5 times, reaching 90% of conversion in 6h, when 60mg of molecular sieves per mmol of butyric acid was used. Finally, the reuse of Lipozyme TL-IM for the ultrasound-assisted synthesis of ethyl butyrate was verified for 10 batches, without any appreciable loss of activity, whereas in systems using mechanical agitation, the biocatalyst was completely inactivated after 5 batches. These results suggest that the combined use of ultrasound and molecular sieves greatly improve esterification reactions by stabilizing the enzyme and increasing yields.</abstract><cop>Kidlington</cop><pub>Elsevier B.V</pub><pmid>24844439</pmid><doi>10.1016/j.ultsonch.2014.05.004</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record>
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source MEDLINE; Elsevier ScienceDirect Journals
subjects Ascomycota - enzymology
Biocatalysis
Butyrates - chemical synthesis
Butyrates - chemistry
Catalysis
Chemistry
Chemistry Techniques, Synthetic - methods
Enzymes, Immobilized - chemistry
Enzymes, Immobilized - metabolism
Esterification
Esterification reactions
Exact sciences and technology
General and physical chemistry
Ion Exchange Resins - chemistry
Lipase - chemistry
Lipase - metabolism
Lipases
Lipozyme TL-IM
Molecular sieves
Operational stability
Physical chemistry of induced reactions (with radiations, particles and ultrasonics)
Temperature
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Ultrasonic chemistry
Ultrasonics
Ultrasound
title The combined use of ultrasound and molecular sieves improves the synthesis of ethyl butyrate catalyzed by immobilized Thermomyces lanuginosus lipase
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