Reaction Acceleration in Thin Films with Continuous Product Deposition for Organic Synthesis
Abstract
Thin film formats are used to study the Claisen-Schmidt base-catalyzed condensation of 6-hydroxy-1-indanone with substituted benzaldehydes and to compare the reaction acceleration relative to the bulk. Relative acceleration factors initially exceeded 103 and were on the order of 102 at steady state, although the confined volume reaction was not electrostatically driven. Substituent effects were muted compared to those in the corresponding bulk and microdroplet reactions and it is concluded that the rate-limiting step at steady state is reagent transport to the interface. Conditions were found that allowed product deposition from the thin film to occur continuously as the reaction mixture was added and as the solvent evaporated. Yields of 74% and production rates of 98 mgh–1 were reached in a very simple experimental system that could be multiplexed to greater scales.
- Publication Date:
- Research Org.:
- Purdue Univ., West Lafayette, IN (United States)
- Sponsoring Org.:
- USDOD; Defense Advanced Research Projects Agency (DARPA); USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1533109
- Alternate Identifier(s):
- OSTI ID: 1374907
- Grant/Contract Number:
- FG02-06ER15807; W911NF-16-2-0020
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Angewandte Chemie (International Edition)
- Additional Journal Information:
- Journal Name: Angewandte Chemie (International Edition); Journal Volume: 56; Journal Issue: 32; Journal ID: ISSN 1433-7851
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; chemistry; confined-volume reactions; mass spectrometry; reaction acceleration; spray-based ionization; thin films
Citation Formats
Wei, Zhenwei, Wleklinski, Michael, Ferreira, Christina, and Cooks, R. Graham. Reaction Acceleration in Thin Films with Continuous Product Deposition for Organic Synthesis. United States: N. p., 2017.
Web. doi:10.1002/anie.201704520.
Wei, Zhenwei, Wleklinski, Michael, Ferreira, Christina, & Cooks, R. Graham. Reaction Acceleration in Thin Films with Continuous Product Deposition for Organic Synthesis. United States. https://doi.org/10.1002/anie.201704520
Wei, Zhenwei, Wleklinski, Michael, Ferreira, Christina, and Cooks, R. Graham. Mon .
"Reaction Acceleration in Thin Films with Continuous Product Deposition for Organic Synthesis". United States. https://doi.org/10.1002/anie.201704520. https://www.osti.gov/servlets/purl/1533109.
@article{osti_1533109,
title = {Reaction Acceleration in Thin Films with Continuous Product Deposition for Organic Synthesis},
author = {Wei, Zhenwei and Wleklinski, Michael and Ferreira, Christina and Cooks, R. Graham},
abstractNote = {Thin film formats are used to study the Claisen-Schmidt base-catalyzed condensation of 6-hydroxy-1-indanone with substituted benzaldehydes and to compare the reaction acceleration relative to the bulk. Relative acceleration factors initially exceeded 103 and were on the order of 102 at steady state, although the confined volume reaction was not electrostatically driven. Substituent effects were muted compared to those in the corresponding bulk and microdroplet reactions and it is concluded that the rate-limiting step at steady state is reagent transport to the interface. Conditions were found that allowed product deposition from the thin film to occur continuously as the reaction mixture was added and as the solvent evaporated. Yields of 74% and production rates of 98 mgh–1 were reached in a very simple experimental system that could be multiplexed to greater scales.},
doi = {10.1002/anie.201704520},
journal = {Angewandte Chemie (International Edition)},
number = 32,
volume = 56,
place = {United States},
year = {Mon May 29 00:00:00 EDT 2017},
month = {Mon May 29 00:00:00 EDT 2017}
}
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