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Surya Prakash

Distinguished Professor, George A. and Judith A. Olah Nobel Laureate Chair in Hydrocarbon Chemistry and Professor of Chemistry and Chemical Engineering and Materials Science
Surya Prakash
Email gprakash@usc.edu Office LHI 103 Office Phone (213) 740-5984

Research & Practice Areas

Professor Prakash and his group’s research interests are in the area of Synthetic Organic, Mechanistic and Hydrocarbon chemistry related to energy. Our projects cover a wide range of subjects in the area of selective fluorinations, oxidations, energetic materials, reductions, stereoselective reactions, electrochemical synthesis, hydrocarbon activation and isomerization, direct oxidation fuel cells, lithium ion battery electrolytes, electrochemistry, polymer chemistry, superacid catalyzed reactions, stable carbocation chemistry, application of ab initio and DFT theory and NMR chemical shift calculations. Our group also utilizes extensively all the modern spectroscopic and analytical tools in organic structure characterization as well as in mechanistic studies.

Video

Biography

Professor Surya Prakash was born in 1953 in Bangalore, India. He holds a B.Sc. (Hons) in Chemistry (1972) from the Bangalore University and a M.Sc. from IIT, Madras (1974). He obtained his Ph. D. in chemistry under the tutelage of late Professor Olah (1994 Nobel Laureate in Chemistry) at the University of Southern California (USC) in 1978. He joined USC faculty in 1981 and is currently a Professor of Chemistry, Chemical Engineering and Materials Science, and Director holding the Georeg A. and Judith A. Olah Nobel Laureate Chair in Hydrocarbon Chemistry at the Loker Hydrocarbon Research Institute. He also served as the Chairman of the Chemistry Department (2017-2021). His research encompasses superacid, hydrocarbon, synthetic organic, organosilicon and organofluorine chemistry, with particular emphasis in the areas of energy, greenhouse gas abatement and catalysis. He is a Co-Proponent of the Methanol Economy Concept based on carbon dioxide capture and recycling.  He co-invented the direct oxidation methanol fuel cell. He has trained more than 150 doctoral and post-doctoral scholars. He is a prolific author with ~ 840 peer-reviewed publications holding > 120 patents. He has published 14 books. He has received many awards and recognitions including the American Chemical Society Awards: 2004 Creative Work in Fluorine Chemistry, 2006 George A. Olah Award in Hydrocarbon or Petroleum Chemistry, 2006 Richard C. Tolman Award and 2018 Arthur C. Cope Late Career Scholars Award. He has also received the 2007 Distinguished Alumni Award from IIT, Madras and the 2010 CRSI Medalfrom the Chemical Research Society of India. He has co-shared with the late Professor Olah, the inaugural $1 Million the 2013 Eric and Sheila Samson Prime Minister’s Prize for Innovation in Alternative Fuels for Transportation by the State of Israel. In 2015, he won the Henri Moissan International Prize for excellence in Fluorine Chemistry. He is a Fellow of the AAAS, a Member of the European Academy of Arts, Sciences and Humanities, a Fellow of the European Academy of Sciences, Foreign Fellow of National Academy of Sciences, India and a Fellow of the American Chemical Society. He also sits on Editorial Boards of several International Journals. Prakash’s co-authored book (with G. A. Olah and A. Goeppert), “Beyond Oil and Gas: The Methanol Economy” (1st Edition, 2006; 2nd Edition, 2009; 3rd Expanded Edition 2018, Wiley VCH, translated into Chinese, Hungarian, Japanese, Swedish and Russian) is getting worldwide attention.

 

Education

  • Ph.D. , University of Southern California, 1/1978
  • M.S. , I.I.T., Madras, India, 1/1974
  • B.S. , Bangalore University, India, 1/1972

  • Summary Statement of Research Interests

    Professor Prakash has broad range of interests in synthetic organic and organofluorine chemistry, hydrocarbon chemistry and energy storage areas. Since 1989, Prakash has collaborated with NASA’s Jet Propulsion Laboratory (JPL)/Caltech to develop the methanol fuel cell as part of a project funded by the Defense Advanced Research Projects Agency. He has engineered a membrane that blocks methanol; representing a major break-through in terms of commercializing the methanol fuel-cell technology. The work has many practical applications. Smart Fuel Cell Corp. (SFC) have obtained a license from USC-Caltech to commercialize the Methanol Fuel Cell Technology. The Methanol Economy Concept patents co-developed with Professor Olah have been licensed to UOP-Honeywell by USC.

    Detailed Statement of Research Interests

    Synthetic Organic, Mechanistic, Hydrocarbon and Energy Related Chemistry

    Professor Prakash and his group’s research interests cover a wide range of subjects in the area of selective fluorinations, oxidations, energetic materials, reductions, stereoselective reactions, electrochemical synthesis, hydrocarbon activation and isomerization, anthropogenic CO2 capture and conversion to carbon-neutral fuels and feed-stocks, direct oxidation fuel cells, lithium ion battery electrolytes, iron batteries, flow batteries, electrochemistry, polymer chemistry, superacid catalyzed reactions, stable carbocation chemistry, application of ab initio and DFT theory and NMR chemical shift calculations. Our group also utilizes extensively all modern spectroscopic and analytical tools in organic structure characterization as well as in mechanistic studies. Synthetic Organic Chemistry Our efforts in this area mainly emphasize the development of new reactions and reagents, which greatly benefit practicing synthetic organic chemists. Although our goal is not oriented towards target molecule synthesis, development of single step selective and stereoselective transformations is of immense value in general organic synthesis. We have developed many fluorination protocols based on pyridinium polyhydrogen fluorides (ionic liquids) as room temperature nucleophilic fluorinating agents. Many of the methods replace the use of highly toxic HF and elemental fluorine. Selective trifluoromethylations, difluoromethylations and difluoromethylenations have been achieved using the trifluoromethyltrimethylsilane (the Ruppert-Prakash Reagent). Related fluoroalkylations using sulfur-based reagents have shown great promise. Recent efforts involve fluoroalkylation and fluoroalkoxylations involving photoredox catalysis. Such methods have gained wide use in the area of small molecule-based drug discovery. Silicon reagents such as trialkylsilanes, trimethylsilyl nitrile and azide have been developed as useful synthons. A new ionic hydrogenation method using trialkylsilanes as reducing agent has resulted in general-purpose ether and sulfide synthesis method. We have adopted the method for the preparation of polymers and crown ethers. Increasingly, superacids serve as excellent high acidity medium for electrophilic reactions (so called superelectrophilic activation). Using CF3SO3H, CH3SO3H or BF3-H2O as a high acidity and non-oxidizing medium, a host of new reactions for deactivated aromatics such as iodination, acylation, nitration etc., are being developed. Use of solid strong acid catalysts such as Nafion-HR (an ionomeric perfluoroalkane type sulfonic acid) are also being investigated. 

    Mechanistic Studies

    These studies involve generation of reactive electrophilic intermediates such as carbocations, carbodications, halonium ions, diazonium ions, oxonium ions, acylium ions, thioacylium ions, nitrenium ions, silicenium ions and selenonium ions in low nucleophilicity highly acidic solvent systems and their characterization using low temperature broad-band nuclear magnetic resonance spectroscopy (1H, 2H, 13C, 19F, 17O, 29Si, 77Se, 15N, 35Cl, etc.,). Other techniques such as infrared and X-ray photoelectron spectroscopy are also employed to characterize their structures. Using the above methods, a wide variety of trivalent (classical) and bridged (non-classical) carbocations have been characterized along with some new aromatic cationic systems. Several empirical correlations to relate positive charge density and chemical shifts were developed. Other reactive intermediates studied include carbanions, including trifluoromethanide anion, and oxonium ylides. In conjunction with these studies a wide array of two-dimensional NMR techniques and special pulse sequences are routinely employed. Solid-state 13C NMR spectra of carbocation salts are also obtained using cross polarization magic angle spinning techniques (CPMAS). In this area ab initio and DFT calculations are routinely employed to delineate structure and energetics of complex carbocation structures. The minimized structures are also used in NMR chemical shift calculations.

    Hydrocarbon and Energy Related Chemistry

    Utilization of saturated hydrocarbons including methane as raw materials to synthesize value added compounds. Use of hydrocarbons and oxygenated hydrocarbons (particularly methanol) as fuels in direct oxidation fuel cells. Hydrocarbon isomerization, functionalization (nitration, carbonylation, hydroxylation, sulfuration, etc.,) and synthesis of polycyclic cage hydrocarbons. Polymerization of ethylene and α-olefins to polyolefins by aluminum subhalide chemistry. Polymerization of unusual monomers. Proton conducting polymer electrolytes for fuel cells and lithium ion batteries. Superacid facilitated upgrading of fossil fuels (such as coal, methane, etc.) to industrially useful feedstocks. Electrochemical reduction of anthropogenic carbon dioxide to formic acid, methanol and related derivatives. Development of CO2 capture and carbon neutral energy cycles through the Methanol EconomyTM concept. Using methanol and formic acid as hydrogen storage media. Development of rechargeable aqueous batteries based on iron- nickel and organic redox flow materials. 

    • Conversion of carbon dioxide to methanol and/or dimethyl ether using bi-reforming of methane or natural gas, G. A. Olah and G. K. S. Prakash, U.S. Patent, 7,909,559, March 15, 2011.
    • Nanostructured solid regenerable absorbents for reversible absorption of carbon dioxide from gases, including air, G. A. Olah, A. Goeppert, S. Meth and G. K. S. Prakash, US Patent, 7,795,175, September 14, 2010.
    • US Patent: Selective Conversion of Carbon Dioxide to Methanol, Dimethyl Ether and Derived Products, G. A. Olah and G. K. S. Prakash, US Patent, 7,846,978, December 2010
    • US Patent: Efficient and Selective Chemical Recycling of Carbon Dioxide to Methanol, Dimethyl Ether and Derived Products, G. A. Olah and G. K. S. Prakash, US Patent, 7,608, 743, October, 27, 2009.
    • US Patent: Efficient and Selective Conversion of Carbon Dioxide to Methanol, Dimethyl Ether and Derived Products, G. A. Olah and G. K. S. Prakash, US Patent, 7,605, 293, October, 20, 2009.
    • US Patent: Electrolysis of carbon dioxide in aqueous media to carbon monoxide and hydrogen for production of methanol, G. A. Olah and G. K. S. Prakash, US Patent, 7,704,369, April 27, 2010
    • US Patent: Selective Oxidative Conversion of Methane to Methanol, Dimethyl Ether and Derived Products, G. A. Olah and G. K. S. Prakash, US Patent, 7,705,059, April 27, 2010.

  • Book Chapters

    • Reddy, V. P., Prakash, S. G. (2009). Recent Studies of Persistent Carbodications in Adv. Phys. Org. Chem. (Vol. 43) pp. 219-260. Academic Press.

    Journal Article

    • Prakash, S. G., Ganesh, S. K., Jones, J., Kulkarni, A., Masood, K., Swabeck, J. K., Olah, G. A. (2012). Difluoromethylation of Aryl (Heteroaryl) Iodides and ß-Styrenyl Halides using Copper Mediated Tributyl(difluoromethyl)stannane. Angew. Che. Int. Ed.. Vol. 51, pp. 12090-12094.
    • Prakash, S. G., Mathew, T., Olah, G. A. (2012). Gallium(III) Triflate: An Efficient Lewis Acid Catalyst for Organic Synthetic Transformations. Accounts of Chemical Research. Vol. 45, pp. 565-577.
    • Prakash, S. G., Wang, F., Rahm, M., Shen, J., Ni, C., Haiges, R., Olah, G. A. (2011). On the Nature of C-H—F-C Interactions in Hindered CF3-C(sp3) Bond Rotations. Angew. Chem. Int. Ed.. Vol. 50, pp. 11761-11764.
    • Olah, G. A., Prakash, S. G., Goeppert, A. (2011). Anthropogenic Chemical Carbon Cycle for a Sustainable Future. J. Am. Chem. Soc. Vol. 133, pp. 12881-12898.
    • Prakash, S. G., Jog, P. V., Krishnan, H. S., Olah, G. A. (2011). A Novel Domino Approach (Hydrolysis/ Dehydrohalogenation/ Heck Coupling) for the Synthesis of Styrene Sulfonate Salts. J. Am. Chem. Soc. Vol. 133, pp. 2140-2143.
    • Prakash, S. G., Ni, C., Wang, F., Hu, J., Olah, G. A. (2011). From Difluoromethyl 2-Pyridyl Sulfone to Difluorinated Sulfonates: A Unique Protocol for Nucleophilic Difluoro(sulfonato)methylation. Angew. Chem. Int. Ed.. Vol. 50, pp. 2559-2563.
    • Goeppert, A., Meth, S., Prakash, S. G., Olah, G. A. (2010). Nano Structured Silica as a support for regenerable high capacity organo-amine based CO2 sorbents. Energy & Environmental Science. Vol. 3 (12), pp. 1949-1960.
    • Prakash, S. G., Zibinsky, M., Upton, T. G., Kashemirov, B. A., McKenna, C. E., Goodman, M. F., Batra, V. K., Pederson, L. C., Shock, D. D., Beard, W. A., Wilson, S. H., Olah, G. A. (2010). Synthesis and biological evaluation of fluorinated deoxynucleotide analogs based on bis-(difluoromethylene)triphosphoric acid. Proc. Natl. Acad. Sci. USA. Vol. 107 (36), pp. 15693-15698.
    • West, W. C., Shevade, A., Soler, J., Kulleck, J., Smart, M. C., Ratnakumar, B. V., Moron, M., Haiges, R., Christe, K. O., Prakash, S. G. (2010). Sulfuryl and Thionyl Halide- Based Ultralow Temperature Primary Batteries. J. Electrochem. Soc.. Vol. 157, pp. A571-A577.
    • Prakash, S. G., Wang, F., Shao, N., Mathew, T., Rasul, G., Haiges, R., Stewart, T., Olah, G. A. (2009). A Persistent alpha-Fluorocarbanion and Its Analogues: Preparation, Characterization, and Computational Study. Angw. Chem. Int. Ed.. Vol. 48, pp. 5358-5362.
    • Prakash, S. G., Wang, F., Stewart, T., Mathew, T., Olah, G. A. (2009). a-Fluoro- a-nitro(phenylsulfonyl)methane as a fluoromethyl pronucleophile: Efficient stereoselective Michael addition to chalcones. Proc. Natl. Acad. Sci. USA. Vol. 106, pp. 4090-4094.
    • Olah, G. A., Goeppert, A., Prakash, S. G. (2009). Chemical Recycling of Carbon Dioxide to Methanol and Dimethyl Ether: From Greenhouse Gas to Renewable, Environmentally Carbon Neutral Fuels and Synthetic Hydrocarbons. J. Org. Chem. Vol. 74, pp. 487-498.
    • US Patent, Electrolysis of carbon dioxide in aqueous media to carbon monoxide and hydrogen for production of methanol, G. A. Olah and G. K. S. Prakash, U.S. Patent, 8,138,380, March 20, 2012, 2011-2012
    • US Patent, Conversion of carbon dioxide to dimethyl ether using bi-reforming of methane or natural gas, G. A. Olah and G. K. S. Prakash, U.S. Patent, 8,133,926, March 20, 2012., 2011-2012
    • US Patent, Efficient and selective chemical recycling of carbon dioxide to methanol, dimethyl ether and derived products, G. A. Olah and G. K. S. Prakash, U.S. Patent, 8,212,088, July 3, 2012., 2011-2012
    • American Association for the Advancement of Science Fellow, Fellow, 2005
    • USC Endowed Chair, George A. and Judith A. Olah Nobel Laureate Chair in Hydrocarbon Chemistry, 1997/01/01-2024/08/15
    • Daneshy International Award for Best Invention on Energy Transition, E-CET, Viterbi School of Engineering, University of Southern California, 2022-2023
    • American Chemical Society Arthur C. Cope Late Career Scholar Award, 2017-2018
    • Prix Henri Moissan Prize for Excellence in Fluorine Chemistry, 2014-2015
    • ASEI Scientist of the Year, Chemistry & Chemical Engineering, American Association of Engineers of Indian Origin, 2013-2014
    • Elected Fellow of the American Chemical Society (ACS Fellow), 2013-2014
    • The National Academy of Sciences, India (NASI) Fellow, 2013
    • Fellow (or Equivalent) of National Society in Discipline, Fellow of the European Academy of Sciences, 2011-2012
    • USC Raubenheimer Outstanding Senior Faculty Award, For Exemplary Contributions in the Areas of Teaching, Research and Service , 2011-2012
    • Burgenstock Lecturer, 2010, 2009-2010
    • CRSI Medal, Chemical Research Society of India, 2009-2010
    • Professor K. Venkataraman Lecturer, 2008-2009, University Department of Chemical Technolgy, University of Mubai, India., 2008-2009
    • Distinguished Alumnus Award, Indian Institute of Technology, Madras, India, 2006-2007
    • George A. Olah Annual Lecturer, 2006-2007
    • Richard C. Tolman Award, Southern California Section of American Chemical Society, 2006-2007
    • American Chemical Society George A. Olah National Award in Hydrocarbon or Petroleum Chemistry, 2005-2006
    • Fellow of the American Association of Advancement of Science , 2005-2006
    • NASA Space Act Board Award, New Fuels For Direct Oxidation Fuel Cells, 2004-2005
    • American Chemical Society National Award for Creative Work in Fluorine Chemistry, 2003-2004
    • USC Associates Award For Creativity In Research And Scholarship, 2000
    • JPL/TAP Group Achievement Award for Low Crossover Membranes for Methanol Fuel Cells, 1998-1999
    • Phi Kappa Phi Faculty Recognition Award for Research and Scholarship, 1983-1984

  • Administrative Appointments

    • Director, Loker Hydrocarbon Research Institute, 2010 – 2015
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