Improved Chemical SynthesisImproved Chemical Synthesis ...
Improved Chemical Synthesis Using Automated Microfluidic Platforms
Jonathan McMullen & Klavs F. Jensen
Department of Chemical Engineering Massachusetts Institute of Technology Cambridge, MA 02139 617 253 4589 kfjensen@mit.edu web.mit.edu/jensenlab
Chemistry classic science traditionally performed batchwise
~1900
~1750
~2000
2
1
Continuous flow microsystems reduce cost of information per experiment and enable new operating conditions
Reactor 2 Separator Reactor 1
Integrated continuous, microreactors, separation and detection units in chemically compatible materials
High throughput, automated, and optimized synthesis Integrates analytics and workflow Less waste and better use of resources Platform for exploring new reaction chemistry and conditions not
easily accessed in batch
3
Microreactor technology advantages Controlling mixing
Desired features:
? chemical compatibility (e.g., glass surfaces)
? controlled mixing
activator acceptor donor
D. Ratner, K.F. Jensen, P. Seeberger et al.,
4
Chem Comm 2005, 24, 578
2
Microreactor technology advantages Controlling mixing
Desired features:
? chemical compatibility (e.g., glass surfaces)
? controlled mixing
activator acceptor donor
DU. Rsaitnnegr, gK.aF.sJetnosemn,iPx. Seeberger et al.,
5
Ch-emBlCaocmkmin2k00i5n,t2o4,w5a7t8er (S. Khan)
Microreactor technology advantages Controlling residence time and temperature
TE heater/ cooler
Desired features:
? chemical compatibility ? controlled mixing ? well defined reaction time
(residence time) ? ability to quench reaction ? temperature control (bath
or TE element) ? connections to fluid
handling
Heat sink fluid chamber
40 mm
3
Microreactors can be fabricated for a variety of reactions
Chips customized for
? Gas ? liquid reaction ? Gas ? liquid ? solid
reaction ? Immobilized catalyst
Reactors integrated with
? Heaters ? Mixers ? Separators ? Temperature measurement ? Spectroscopy
7
Continuous flow systems could revolutionize the development and production chain for fine chemicals and pharmaceuticals
Discovery
Laboratory
Plant
`
Biologists Chemists
Chemists Engineers
Different discovery, development and production platforms are slow and complicate scale-up
Integrated and automated continuous process platforms span across length scales and accelerate translation of
8 discoveries into development and production
4
Combining continuous flow microreactors with liquid handling yields a reaction screening platform
? Set reaction temperature and residence time
? Withdraw reagents from sample well
? Inject samples into microfluidic flow system
? Detect reaction segment
? Collect reaction segment
? Perform analysis offline
Liquid handler
Flow inlets
Temp. control
UV/Vis
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To waste
Fraction collector
J.R. Goodell, J.P. McMullen, K.F. Jensen, J.A. Porco, A.B. Beeler, et al., J. Org. Chem (in press)
Combining continuous flow microreactors with liquid handling yields a reaction screening platform
reagents
O
O MeO
H
Ph Me 3H
Continuous screening of
reactions - building a library
A1+B, A1+C, ... A2+B, A2+C, ...
Ex: retro Dieckmann reaction analysis by UPLC
Compound libraries can be generated quickly
10
J.R. Goodell, J.P. McMullen, K.F. Jensen, J.A. Porco, A.B. Beeler, et al., J. Org. Chem (in press)
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