Mathematical modeling of a continuous-flow packed-bed reactor with immobilized lipase for kinetic resolution of (R,S)-2-pentanol.

Aslı Soyer Malyemez,Ülkü Mehmetoğlu,Abdulwahab Giwa,Emine Bayraktar

doi:10.3906/kim-1910-22

Abstract

In this study, the kinetic resolution of (R,S)-2-pentanol via transesterification to achieve S-2-pentanol, a key intermediate required in the synthesis of anti-Alzheimer drugs, was investigated in continuous-flow packed-bed reactors. The effects of residence time, substrate concentration, and operation time of the enzyme were investigated. Under steady state conditions, 50% conversion and enantiomeric excess of the substrate (ee S >99% were achieved at a residence time of 0.04 min. Productivity of the continuous-flow process (1.341 mmol/min/g)was about 4 times higher than that of the corresponding batch process (0.363 mmol/min/g). In addition, the mathematical modeling of the packed-bed reactor was conductedusing an axial dispersion model. Ping Pong Bi Bi kinetics was used in this model. Design parameters were determined and the developed equations were solved using an algorithm for solving boundary value problems for ordinary differential equations by collocation (bvp4c) using MATLAB. The results, obtained from the model, fitted the experimental data very well.).

Highlights

Pure secondary alcohols and their derivatives are widely used as building blocks in the chemical and pharmaceutical industries
The production of (S)-2-pentanol, using immobilized lipase, with a continuous-flow packed-bed reactor has not been investigated in detail far
Kinetic resolution of (R,S)-1-phenylethanol was investigated in batch and continuous-flowpacked-bed reactors

Summary

Introduction

Pure secondary alcohols and their derivatives are widely used as building blocks in the chemical and pharmaceutical industries. In order to obtain maximum enantioselectivity with kinetic resolution, the reaction must be terminated after a certain time This can be performed via regulation of the flow rate; in other words, the residence time in the continuous-flow system. The production of (S)-2-pentanol, using immobilized lipase, with a continuous-flow packed-bed reactor has not been investigated in detail far. Kinetic resolution of (R,S)-1-phenylethanol was investigated in batch and continuous-flowpacked-bed reactors. It was found that the continuous-flow reactions were successfully performed for the kinetic resolution of 1-phenylethanolwithout enantioselectivity changes related to the reactor configuration, and the productivity (specific rate) of the lipases was higher in the continuous-flow reactor than. Kinetic resolution of (R,S)-2pentanol (Figure 1) was studied in a continuous-flow packed-bed reactor. The packed-bed reactor design model was investigated and equations of the proposed model were solved using MATLAB (MathWorks, Inc., Natick, MA, USA)

Materials and methods

Analytical model

Mathematical method

Findings

Effect of substrate concentration