Accelerated Chemical Reactions and Organic Synthesis in Leidenfrost Droplets

Bain, Ryan M.; Pulliam, Christopher J.; Thery, Fabien; Cooks, R. Graham

doi:10.1002/ange.201605899

Title: Accelerated Chemical Reactions and Organic Synthesis in Leidenfrost Droplets

Journal Article · 28 July 2016 · Angewandte Chemie

DOI: https://doi.org/10.1002/ange.201605899 · OSTI ID:1400996

Bain, Ryan M. ^[1]; Pulliam, Christopher J. ^[1]; Thery, Fabien ^[2]; Cooks, R. Graham ^[1]

Department of Chemistry Purdue University 560 Oval Drive West Lafayette IN USA
Department of Chemistry Purdue University 560 Oval Drive West Lafayette IN USA, Laboratory of Neuroscience University of Lille 1 France

Abstract Leidenfrost levitated droplets can be used to accelerate chemical reactions in processes that appear similar to reaction acceleration in charged microdroplets produced by electrospray ionization. Reaction acceleration in Leidenfrost droplets is demonstrated for a base‐catalyzed Claisen–Schmidt condensation, hydrazone formation from precharged and neutral ketones, and for the Katritzky pyrylium into pyridinium conversion under various reaction conditions. Comparisons with bulk reactions gave intermediate acceleration factors (2–50). By keeping the volume of the Leidenfrost droplets constant, it was shown that interfacial effects contribute to acceleration; this was confirmed by decreased reaction rates in the presence of a surfactant. The ability to multiplex Leidenfrost microreactors, to extract product into an immiscible solvent during reaction, and to use Leidenfrost droplets as reaction vessels to synthesize milligram quantities of product is also demonstrated.

View Accepted Manuscript (Publisher)

Cite

Export

Save

Sponsoring Organization:: USDOE

Grant/Contract Number:: FG02-06ER15807

OSTI ID:: 1400996

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Journal Issue: 35 Vol. 128; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

References (25)

Accelerated CarbonCarbon Bond-Forming Reactions in Preparative Electrospray Müller, Thomas; Badu-Tawiah, Abraham; Cooks, R. Graham Angewandte Chemie, Vol. 124, Issue 47 https://doi.org/10.1002/ange.201206632	journal	October 2012
Syntheses of Isoquinoline and Substituted Quinolines in Charged Microdroplets Banerjee, Shibdas; Zare, Richard N. Angewandte Chemie, Vol. 127, Issue 49 https://doi.org/10.1002/ange.201507805	journal	October 2015
The Role of the Interface in Thin Film and Droplet Accelerated Reactions Studied by Competitive Substituent Effects Li, Yafeng; Yan, Xin; Cooks, R. Graham Angewandte Chemie, Vol. 128, Issue 10 https://doi.org/10.1002/ange.201511352	journal	February 2016
Accelerated CarbonCarbon Bond-Forming Reactions in Preparative Electrospray Müller, Thomas; Badu-Tawiah, Abraham; Cooks, R. Graham Angewandte Chemie International Edition, Vol. 51, Issue 47 https://doi.org/10.1002/anie.201206632	journal	October 2012
Syntheses of Isoquinoline and Substituted Quinolines in Charged Microdroplets Banerjee, Shibdas; Zare, Richard N. Angewandte Chemie International Edition, Vol. 54, Issue 49 https://doi.org/10.1002/anie.201507805	journal	October 2015
The Role of the Interface in Thin Film and Droplet Accelerated Reactions Studied by Competitive Substituent Effects Li, Yafeng; Yan, Xin; Cooks, R. Graham Angewandte Chemie International Edition, Vol. 55, Issue 10 https://doi.org/10.1002/anie.201511352	journal	February 2016
Chemical Reactivity Assessment Using Reactive Paper Spray Ionization Mass Spectrometry: The Katritzky Reaction Yan, Xin; Augusti, Rodinei; Li, Xin ChemPlusChem, Vol. 78, Issue 9 https://doi.org/10.1002/cplu.201300172	journal	August 2013
Practical implications of some recent studies in electrospray ionization fundamentals Cech, Nadja B.; Enke, Christie G. Mass Spectrometry Reviews, Vol. 20, Issue 6, p. 362-387 https://doi.org/10.1002/mas.10008	journal	January 2001
Direct analysis of anabolic steroids in urine using Leidenfrost phenomenon assisted thermal desorption-dielectric barrier discharge ionization mass spectrometry Saha, Subhrakanti; Mandal, Mridul Kanti; Nonami, Hiroshi Analytica Chimica Acta, Vol. 839 https://doi.org/10.1016/j.aca.2014.05.009	journal	August 2014
The bursting of soap-bubbles in a uniform electric field Wilson, C. T. R.; Taylor, G. I. Mathematical Proceedings of the Cambridge Philosophical Society, Vol. 22, Issue 5 https://doi.org/10.1017/S0305004100009609	journal	July 1925
Probing Interfacial Chemistry of Single Droplets with Field-Induced Droplet Ionization Mass Spectrometry: Physical Adsorption of Polycyclic Aromatic Hydrocarbons and Ozonolysis of Oleic Acid and Related Compounds Grimm, Ronald L.; Hodyss, Robert; Beauchamp, J. L. Analytical Chemistry, Vol. 78, Issue 11, p. 3800-3806 https://doi.org/10.1021/ac0601922	journal	June 2006
Unraveling the Mechanism of Electrospray Ionization Konermann, Lars; Ahadi, Elias; Rodriguez, Antony D. Analytical Chemistry, Vol. 85, Issue 1 https://doi.org/10.1021/ac302789c	journal	November 2012
Mass Spectrometry of Acoustically Levitated Droplets Westphall, Michael S.; Jorabchi, Kaveh; Smith, Lloyd M. Analytical Chemistry, Vol. 80, Issue 15 https://doi.org/10.1021/ac800317f	journal	August 2008
Straightforward Synthesis of Metal Nanoparticles and Hierarchical Porous Metals Assisted by Partial Film Boiling Phenomena Lee, Dong-Wook; Jin, Min-Ho; Lee, Chun-Boo Chemistry of Materials, Vol. 27, Issue 15 https://doi.org/10.1021/acs.chemmater.5b00143	journal	July 2015
On-Line Synthesis and Analysis by Mass Spectrometry Bain, Ryan M.; Pulliam, Christopher J.; Raab, Shannon A. Journal of Chemical Education, Vol. 92, Issue 12 https://doi.org/10.1021/acs.jchemed.5b00165	journal	September 2015
Inverse Leidenfrost Effect: Levitating Drops on Liquid Nitrogen Adda-Bedia, M.; Kumar, S.; Lechenault, F. Langmuir, Vol. 32, Issue 17 https://doi.org/10.1021/acs.langmuir.6b00574	journal	April 2016
Mass Spectrometry in Organic Synthesis: Claisen–Schmidt Base-Catalyzed Condensation and Hammett Correlation of Substituent Effects Bain, Ryan M.; Pulliam, Christopher J.; Yan, Xin Journal of Chemical Education, Vol. 91, Issue 11 https://doi.org/10.1021/ed500288m	journal	July 2014
Dynamics of Field-Induced Droplet Ionization: Time-Resolved Studies of Distortion, Jetting, and Progeny Formation from Charged and Neutral Methanol Droplets Exposed to Strong Electric Fields Grimm, Ronald L.; Beauchamp, J. L. The Journal of Physical Chemistry B, Vol. 109, Issue 16 https://doi.org/10.1021/jp0450540	journal	April 2005
Green chemistry and nanofabrication in a levitated Leidenfrost drop Abdelaziz, Ramzy; Disci-Zayed, Duygu; Hedayati, Mehdi Keshavarz Nature Communications, Vol. 4, Issue 1 https://doi.org/10.1038/ncomms3400	journal	October 2013
Accelerated bimolecular reactions in microdroplets studied by desorption electrospray ionization mass spectrometry Girod, Marion; Moyano, Encarnacion; Campbell, Dahlia I. Chem. Sci., Vol. 2, Issue 3 https://doi.org/10.1039/C0SC00416B	journal	January 2011
Accelerated Hantzsch electrospray synthesis with temporal control of reaction intermediates Bain, Ryan M.; Pulliam, Christopher J.; Cooks, R. Graham Chemical Science, Vol. 6, Issue 1 https://doi.org/10.1039/C4SC02436B	journal	January 2015
Microdroplet fusion mass spectrometry for fast reaction kinetics Lee, Jae Kyoo; Kim, Samuel; Nam, Hong Gil Proceedings of the National Academy of Sciences, Vol. 112, Issue 13 https://doi.org/10.1073/pnas.1503689112	journal	March 2015
Some Investigations on the Deformation and Breaking of Water Drops in Strong Electric Fields Macky, W. A. Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 133, Issue 822 https://doi.org/10.1098/rspa.1931.0168	journal	October 1931
Investigations on Lightning Discharges and on the Electric Field of Thunderstorms Wilson, C. T. R. Philosophical Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 221, Issue 582-593 https://doi.org/10.1098/rsta.1921.0003	journal	January 1921
Leidenfrost Dynamics Quéré, David Annual Review of Fluid Mechanics, Vol. 45, Issue 1 https://doi.org/10.1146/annurev-fluid-011212-140709	journal	January 2013

Similar Records

Accelerated Chemical Reactions and Organic Synthesis in Leidenfrost Droplets

Journal Article · 2016 · Angewandte Chemie (International Edition) · OSTI ID:1401698

Bain, Ryan M.; Pulliam, Christopher J.; Thery, Fabien; +1 more

Conducting reactions in Leidenfrost-levitated droplets

Patent · 2020 · OSTI ID:1735255

Cooks, Robert Graham; Pulliam, Christopher; Bain, Ryan M.

Conducting reactions in leidenfrost-levitated droplets

Patent · 2022 · OSTI ID:1986643

Cooks, Robert Graham; Pulliam, Christopher; Bain, Ryan M.

Title: Accelerated Chemical Reactions and Organic Synthesis in Leidenfrost Droplets

Citation Formats

References (25)

Similar Records

Related Subjects