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Capillary-based microreactor for high throughput catalyst screening in Lewis acid and strong Brønsted acid catalyzed reactions

Li, Si (2012) Capillary-based microreactor for high throughput catalyst screening in Lewis acid and strong Brønsted acid catalyzed reactions. Master's Thesis, University of Pittsburgh. (Unpublished)

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Abstract

The microreactor technique has received considerable research attention due to its promising applications in organic chemistry. Compared to traditional organic synthesis, the employment of microreactor has several advantages. First, the small diameter of the microchannel can reduce the reagent mixing time to milliseconds, allowing fast heat transfer and thermal equilibrium. Second, higher yield and better selectivity are often observed for reactions carried out in a microreactor. Most importantly, reaction optimization and catalyst library generation can be rapidly achieved by the microreactor with reagents on a small scale.
In the past few years, our group has been developing a capillary-based microreactor system that is capable of high throughput catalyst screening. This system consists of HPLC apparatus, syringe pumps and capillary tubings, which are all commonly used in the chemistry laboratory. Compared with the traditional chip-based microreactor, our system is easy to operate, and simple to modify. Additionally, it couples with gas chromatography (GC) or high-performance liquid chromatography (HPLC) for online analysis, providing near-real-time reaction monitoring.
One of the applications we explored with our microreactor system was the homogeneous catalysis reaction. The first reaction tested was lanthanide-triflate catalyzed allylation of benzaldehyde with tetraallyltin. With GC online analysis, the reaction was successfully carried out in our microreactor system. The optimized reaction condition, 10% catalyst load/60 min reaction time in room temperature, was much milder compared with any published bench top conditions. The screening of 8 different catalysts for the reaction was accomplished within 2 hours, which led to a significantly shortened optimization time.
The online enantiomeric separation analysis method was developed for a strong chiral Brønsted acid catalyzed asymmetric cyanide addition. Six chiral columns and various separation conditions were involved in the method development. Due to the incompatible issue between the reaction solvent and column bonded phases, a GC method was optimized and chose as our interfaced online analysis method.


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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Li, Sisil13@pitt.eduSIL13
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWeber, Stephensweber@pitt.eduSWEBER
Committee MemberMichael, Adrian amichael@pitt.eduAMICHAEL
Committee MemberFloreancig, Paul florean@pitt.eduFLOREAN
Date: 19 September 2012
Date Type: Publication
Defense Date: 9 August 2012
Approval Date: 19 September 2012
Submission Date: 15 August 2012
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 55
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: MS - Master of Science
Thesis Type: Master's Thesis
Refereed: Yes
Uncontrolled Keywords: microreactor, organic synthesis, analytical chemistry, catalyst screening
Date Deposited: 19 Sep 2012 18:15
Last Modified: 15 Nov 2016 14:02
URI: http://d-scholarship.pitt.edu/id/eprint/13611

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