Surya Prakash

George A. and Judith A. Olah Nobel Laureate Chair in Hydrocarbon Chemistry and Professor of Chemistry and Chemical Engineering and Materials Science
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.

Biography

Professor G. K. Surya Prakash, Ph.D., was born in 1953 in Bangalore, India. He earned a B.Sc (Hons) in chemistry from Bangalore University and an M.S. in chemistry from the Indian Institute of Technology, Madras. Prakash came to US in 1974 and joined Professor George Olah’s group at Case Western Reserve University, Cleveland, Ohio to pursue graduate work. He moved with Professor Olah to the University of Southern California (USC) in 1977 to help establish the Loker Hydrocarbon Research Institute and obtained his Ph.D. in physical organic chemistry at USC in 1978. He joined the faculty of USC in 1981 and he is currently a Professor and the holder of the George A. and Judith A. Olah Nobel Laureate Chair in Hydrocarbon Chemistry at the Loker Hydrocarbon Research Institute and Department of Chemistry. He also serves as the Director of the Institute. His primary research interests are in superacid, hydrocarbon, synthetic organic & organofluorine chemistry, with particular emphasis in the areas of energy and catalysis. He is a co-inventor of the proton exchange membrane based direct oxidation methanol fuel cell and a co-proponent (with Professor Olah) of the Methanol Economy concept. Professor Prakash is a prolific author with more than 630 peer-reviewed scientific publications and holds 30 patents. He has also co-authored or edited 10 books. He has received many awards and accolades including two American Chemical Society National Awards: in 2004 for his achievements in the area of fluorine chemistry and in 2006 for his contributions to hydrocarbon chemistry. He also received the 2006 Richard C. Tolman Award from the Southern California section of the American Chemical Society for his scientific contributions to Southern California. He is the recipient of the 2007 Distinguished Alumni Award from his alma mater, Indian Institute of Technology, Madras and the 2010 CRSI Medal from the Chemical Research Society of India. He is a fellow of the American Association of Advancement of Science and a Member of the European Academy of Arts, Sciences and Humanities. He also sits on several Editorial Boards of Chemical Journals.

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 Chemistry:
    We mainly emphasize the development new reactions and reagents, which greatly benefit practicing synthetic organic chemists. Although our goal is not target molecule synthesis oriented, development of single step selective and stereoselective transformations is of immense value in general organic synthesis. Preparation of selectively fluorinated organic compounds is of importance in medicinal chemistry. We have developed many fluorination protocols based on pyridinium polyhydrogen fluorides (ionic liquids) as a room temperature nucleophilic fluorinating agent. Many of the methods replace the use of highly toxic HF and elemental fluorine. Selective fluoroalkylations were also achieved by the use trifluoromethyl- and perfluoroalkyltrialkylsilanes. Related perfluoroalkylations using sulfur-based reagents have shown great promise. A number of silicon reagents such as trialkylsilanes, trimethylsilyl nitrile and azide have been developed as useful synthons. A new ionic hydrogenation methods using trialkylsilanes as reducing agent has resulted in general ether synthesis method. Increasingly superacids serve as excellent high acidity medium for electrophilic reactions (superelectrophilic activation). Using CF3SO3H 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) and gallium triflate (a recyclable strong Lewis acid) are also being investigated. New polymer bead chemistry at nanoscale (nanochemistry) has been ongoing. The nanometer scale polymer spheres with pendant surface functionalities serve as hosts for metal nanoparticles, which can be used as catalysts.

    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 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 routinely 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, Energy and 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 alfa-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 methanol and related derivatives. Development of the Methanol economy conceptR.

    • 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 Chapter

    • 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
    • Fellow, 2005
    • George A. and Judith A. Olah Nobel Laureate Chair in Hydrocarbon Chemistry, 1997/01/01-2024/08/15
    • 2013 Sheila and Eric Samson Prime Minister’s Prize for Alternative Fuels to Transportation from the State of Israel, 2013-2014
    • The National Academy of Sciences, India (NASI) Fellow, 2013
    • Fellow of the European Academy of Sciences, 2011-2012
    • 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