BioChem - DOS

In Situ Separation of the Chiral Target Compound (S)-2-Pentanol in Biocatalytic Reactive Distillation

Industrial & engineering chemistry research

Kü hn, Steffen; Sluyter, Gerrit; Christlieb, Marc-Andreas; Heils, René Stö bener, Anne; Kleber, Joscha; Smirnova, Irina; Liese, Andreas

<P><I>In situ</I> separation of a chiral target compound is realized for the first time as distillate on top of an integrated biocatalytic batch reactive distillation column. The applied reaction system is the racemic resolution of (<I>R</I>/<I>S</I>)-2-pentanol in a transesterification with propyl butyrate, which is catalyzed by immobilized <I>Candida antarctica</I> lipase B (Novozym435). Biocatalyst integration is realized in baskets of wire gauze catalytic packings as column internals. The equilibrium limited reaction is shifted to the product side by fractional distillation of low boiling propanol and the target compound (<I>S</I>)-2-pentanol. Increased molar fractions up to <I>x</I><SUB>(<I>S</I>)-2-PeOH</SUB> = 65 &plusmn; 4% with an enantiomeric excess of 90 &plusmn; 4% and 51 &plusmn; 3% overall conversion are reached for (<I>S</I>)-2-pentanol. Feasibility of the reaction system is investigated in our preselection tool. This tool is developed to evaluate predefined operation conditions in the column setup for transesterification reactions based on criteria regarding biocatalyst stability and boiling point differences between the reactants. The subsequently selected reaction of (<I>R</I>/<I>S</I>)-2-pentanol with propyl butyrate is successfully carried out in a batch reactive distillation column with <I>in situ</I> separation of our target compound (<I>S</I>)-2-pentanol. In contrast to current examples in the literature, this clearly demonstrates the possibility of one-pot target compound isolation within chiral synthesis applying biocatalytic reactive distillation.</P><P><B>Graphic Abstract</B><BR><IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/iecred/2017/iecred.2017.56.issue-22/acs.iecr.7b01163/production/images/medium/ie-2017-01163u_0012.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ie7b01163'>ACS Electronic Supporting Info</A></P>

2017

American Chemical Society

0888-5885

1520-5045

56

22

pp.6451-6461

10.1021/acs.iecr.7b01163

http://click.ndsl.kr/servlet/OpenAPIDetailView?keyValue=05787966&target=NART&cn=NART77968020