Racionalan dizajn niskotemperaturnih eutektičkih otapala za lipazom kataliziranu kinetičku rezoluciju (R,S)-1-feniletanola

master's thesis

• Title (english): Rational design of deep eutectic solvents for lipase catalyzed kinetic resolution (R,S)-1-phenylethanol
• Author: Patricia Galović
• Mentor: Ivana Radojčić Redovniković (mentor)
• Committee member: Marina Cvjetko Bubalo (predsjednik povjerenstva)
• Granter: University of Zagreb; Faculty of Food Technology and Biotechnology; (Department of Biochemical Engineering); (Laboratory for Cell Technology, Application and Biotransformations); Zagreb
• Defense date and country: 2021-12-22, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

Niskotemperaturna eutektička otapala (DES-ovi), kao zelena alternativa organskim otapalima iz neobnovljivih izvora, istraživanjima i implementacijom u enzimski kataliziranim reakcijama pokazuju svoj potencijal buduće primjene u industriji te potencijal zelene kemije kao takve. U ovom je radu primjenom računalnog programa COSMOtherm proveden probir eutektičkih otapala za kinetičku rezoluciju temeljem procjene topljivosti supstrata vinil acetata i (R,S)-1-feniletanola. U odabranim eutektičkim otapalima provedena je kinetička rezolucija te je praćena uspješnost reakcije u hidrofobnom niskotemperaturnom eutektičkom otapalu (Ty:C10) u odnosu na hidrofilno niskotemperaturno eutektičko otapalo (ChCl:U10%) te organsko otapalo etil-acetat (klasično korišteno). Vrijednosti konverzije i enantiomernog viška su se koristile za procjenu uspješnosti reakcije. Timol:dekanska kiselina (Ty:C10) dokazano je najbolje otapalo od ispitanih otapala za provedbu reakcije esterifikacije (R,S)-1-feniletanola, s najvećim udjelom konverzije od 53,04%. Enantiomerni višak je zadovoljavajuć i veći od 97% za sva tri korištena otapala. Također, enantiomerni višak (ee) je najviši za otapalo Ty:C10 i iznosi 98,80%.

Abstract (english)

Deep eutectic solvents (DESs), as a green alternative to organic solvents from non-renewable sources, show their potential for future industrial applications and the potential of green chemistry through research and implementation in enzyme-catalyzed reactions. In this paper, eutectic solvents were investigated for kinetic resolution using the software program COSMOtherm based on the evaluation of the solubility of the substrates vinyl acetate and (R,S)-1-phenylethanol. Kinetic resolution was carried out in selected eutectic solvents and the success of the reaction was monitored in the hydrophobic deep eutectic solvent (Ty:C10) and compared to both hydrophilic deep eutectic solvent (ChCl:U10%) and the organic solvent ethyl acetate (classically used). Conversion and enantiomeric excess values were used to evaluate the success of the reaction. Thymol:decanoic acid (Ty:C10) proved to be the best solvent among the tested solvents for carrying out the esterification reaction of (R,S)-1-phenylethanol with the highest conversion rate of 53.04%. The enantiomeric excess is satisfactory and is more than 97% for all three solvents used. Moreover, the enantiomeric excess (ee) is highest for our most successful solvent Ty:C10 and its value is 98.80%.

• Keywords: zelena kemija; hidrofobna eutektička otapala; lipaza; biokataliza
• Keywords (english): green chemistry; hydrophobic deep eutectic solvents; lipase; biocatalysis
• Language: croatian
• URN:NBN: urn:nbn:hr:159:302093
• Study programme: Title: Bioprocess Engineering; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra inženjer/inženjerka bioprocesnog inženjerstva (magistar/magistra inženjer/inženjerka bioprocesnog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2022-01-31 14:22:05