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Nice Chemistry

Composition, structure, properties and reactions of everything

Scientific and Technical Publications

James D. Burrington

https://orcid.org/0009-0006-1233-5184

 

  1. Selective Oxidation and Ammoxidation Catalysis Mechanisms, resulting in improved understanding of heterogeneous oxidation and ammoxidation systems for a broad range of catalyst systems, including molybdates, antimonates, and tellurates.  Dr. Burrington and colleagues over a 30-year period made significant contributions to the understanding and development this commercially significant technology.  Dr. Burrington’s contributions are represented in a series of papers on the mechanism of oxidation and ammoxidation of hydrocarbons over heterogeneous catalysts, still regarded as the most detailed molecular description to date of the key chemisorption, reaction and catalyst regeneration steps of the process.  Representative examples include:
    • J. D. Burrington, “Selective Oxidation Catalysis: An Organic Chemist’s View of Mechanism,” in Computational Materials, Chemistry and Biochemistry: From Bold Initiatives to the Last Mile, Springer Series in Material Science, vol 284, Sadasivan Shankar, Richard Muller, Thom Dunning, Guan Hua, Chen, eds., pp 733-742 (2021). https://doi.org/10.1007/978-3-030-18778-1.
    • Robert K. Grasselli, C.G. Lugmair, A. F. Volpe Jr., A, Anderddon and J. D. Burrington, “Enhancement of acrylic acid yields in propane and propylene oxidation by selective P doping of MoV(Nb)TeO-based M1 and M2 catalysts.” Catalysis Today 157 (2010) 33-38.
    • Robert K. Grasselli, James D. Burrington, “Oxidation of Low Molecular Weight Hydrocarbons”, in Handbook of Heterogeneous Catalysis, G. Ertl, H. Knozinger, F. Schuth and J. Weittkamp, eds., Ch 14.11.8, pp 3479-3489 (2006).
    • Robert K. Grasselli, Douglas J. Buttrey, James D. Burrington, Arne Andersson, Johan Holmberg, Wataru Ueda, J. Kubo, Claus G. Lugmair and Anthony F.Volpe Jr., “Active Centers, catalytic Behavior,Symbiosis and Redox Properties of MoV(Nb,Ta)TeO Ammoxidation Catalysts”, Topics in Catalysis, 38 (1-3), 7-16, December 2006
    • Robert K. Grasselli *, James D. Burrington , Douglas J. Buttrey, Peter DeSanto J, Claus G. Lugmair, Anthony F. Volpe Jr. and Thomas Weingand.  “Multifunctionality of Active Centers in (Amm)oxidation Catalysts:From Bi-Mo-Ox to Mo-V-Nb-(Te,Sb)-Ox”, Topics in Catalysis, 23 (1-4), August, 2003.
    • Grasselli, R.K., Burrington, J.D., DiCosimo, R., Friedrich, M.S., and Suresh, D.D., “Functionalization of Substituted Aromatic and Heteroaromatic Hydrocarbons by Heterogeneous Catalysis,”  Heterogeneous Catalysis and Fine Chemicals, 1988, 317-326.
    • Robert K. Grasselli and James D. Burrington, “Ammoxidation” (Section 4.6.6) and “Oxidation of Low Molecular Weight Hydrocarbons” (Section 14.11.8) in Handbook  of  Heterogeneous  Catalysis,  2nd  Edition, G.  Ertl,  H.  Knözinger,  F.  Schüth  and  J.  Weitkamp,  Editors.
    • DiCosimo, R., Burrington, J.D., and Grasselli, R.K., "Oxidative Dehydrodimerization of Propylene over a Bi203La203 Oxide Ion Conducting Catalyst," J._Catalysis, 102, 1986, 234.
    • Graasselli, R.K., Brazdil, J.F., and Burrington, J.D., "Fe-Se Tellurates as Ammoxidation  
    • Anderson, A.B., Ewing, D.W., Kim, Y., Grasselli, R.K., Burrington, J.D., and Brazdil, J.F., "Mechanism for Propylene Oxidation to Acrolein on B12MO3012: A Quantum Chemical Study," Journal of Catalysis, 1985, 96, 222.
    • Burrington, J.D., Grasselli, R.K., and Brazdil, J.F., "Solid State and Surface Mechanisms n Selective Oxidation and Ammoxidation Catalysis," Proceedings, 8th Int. Cong. Catal., West Berlin, July 2-6, 1984.
    • Burrington, J.D. and Grasselli, R.K., "Molecular Probes for the Mechanism of Selective Oxidate and Ammoxidation Catalysis," I. & E. Chem., 1984, 23, 393.
    • Burrington, J.D., Kartisek, C.T., and Grasselli, R.K., "Surface Intermediates in Selective Propylene Oxidation and Ammoxidation over Heterogeneous Molybdate and Antimonate Catalysts," J. Catal., 1984, 87, 363.
    • “Iron Selenium Tellurium Oxide Catalysis”, US Pat 4,473,468, JF. Brazdil, R. K. Grasselli and J. D. Burrington , Sept 25, 1984.
    • Burington, J.D., Kartisek, C.T., and Grasselli, R.K., "Mechanism of Nitrogen Insertion in Ammoxidation Catalysis," J. Catal.81, 489-498 (1983).
    • Burrington, J.D., Kartisek, C.T., and Grasselli, R.K., "Surface Intermediates in Selective Olefin Oxidation and Ammoxidation," ACS Petrol. Div. Preprints, 1983, 28, (No. 2), P. 515, Seattle, WA, March 20-25, 1983.
    • Grasselli, R.K., Burrington, J.D., "Selective Oxidation and Ammoxidation of Propylene by Heterogeneous Catalysis," Adv. Catal., Academic Press, Inc., H. Pines ed., Vol. 30, p. 133-163.
    • Burrington, J.D., Kartisek, C.T., and Grasselli, R.K., "Substituent Effect in the Catalytic Oxidation of Propylene," J. Catal. 69, 495
    • Burrington, J.D., Kartisek, C.T., and Grasselli, R.K., "Aspects of Selective Oxidation and Ammoxidation Mechanisms Over Bismuth Molybdate Catalysts.  IV.  The Selective Oxidation of 1,1-d2 Allylamine," J. Catal., 1982, 75, 225
    • Grasselli, R.K., Burrington, J.D., Brazdil, J.F., "Mechanistic Features of Selective Oxidation and Ammoxidation Catalysis," J. Chem. Soc. Faraday Discussion, 1982, 72, 203.
    • Burrington, J.D., Kartisek, C.T., and Grasselli, R.K., "Selective Oxidation and Ammoxidation Mechanisms Over Bismuth Molybdate Catalysts," Division of Petroleum Chemistry on Selective Oxidation and Aromatic Chemistry, American Chemical Society, Washington, D.C., Vol. 24, 1034.
    • Burrington, J.D., Kartisek, C.T., and Grasselli, R.K., "Aspects of Selective Oxidation and Ammoxidation Mechanisms Over Bismuth Molybdate Catalysts.  II.  Allyl Alcohol as a Probe for the Allylic Intermediate," J._Catal.  63, 235.
    • Burrington, J.D. and Grasselli, R.K., "Aspects of Selective Oxidation and Ammoxidation Mechanisms Over Bismuth Molybdate Catalysts," J. Catal. 59, 79 (1979).

 

2. New Catalytic Process for Fine and Specialty Chemicals including catalytic acrylic dimerization, catalytic amino-carbonylation to amino acid derivatives, novel aromatic catalytic oxidation and catalytic oxidative dehydrogenation.  Representative contibutions include:

  • “Making Optically Active Alph-Hydroxy Acids or Precursors,” M.C. Cesa, R. A. Dubbert and J. D. Burrington, US Pat 5,324,856, June 28, 1994.
  • Ammoxidation of Methyl Subsituted Hetereoaromatics To Make Heteraromatic Nitriled, U. S. Pat 5,028,713, April2, 1991, R. K. Grasselli and Robert DiCosimo.
  • “3-Pentenamides from 1,3-Butadiene,” J. D. Burrington, US Pat 4,937,380, June 26, 1990.
  • “Process for Making an Optically Active Mixture of an N-Acyl Amino Ester Containing at least Two Chiral Centers,” M.Cesa, R.Dubbert and J. Burrington. US Pat 4,929,755, May 29, 1990.
  • “Process for making 3-cyanopyridine,” US Pat 4,876,348, Oct 4, 1989, J. D. Burrington.
  • “1,6-Hexanediamides from 3-penteneamides,” J. D. Burrington, US Pat 4,847,411, July 11, 1989.
  • "a-Amino Acids through Catalytic Reaction of CO and a Hydroxyl Compound with Enamides,” M.C.Cesa and J.D. Burrington.  US Pat 4,749,786, June 7, 1988.
  • “Method of Making a Diastereomeric Mixture Containing Two Diasterioner a-Acyloxy Acid Esters,” J. D Burrington, US Pat 4,749,811, June 7, 1988.
  • “Synthesis of Methionine Hydoxy Analog or Derivatives, and Esters Thereof; Synthesis of 1-Acyloxy 4-hydrocarbylthiopropene and Products,” M.C.Cesa and J. D. Burrington.  US Pat 4,782,173, Nov 1, 1988.
  • “Enantio Selective Hydrolysis of N-acylamine Acid Esters Using a Combined Enzyme System,” M.J.King, M.C.Cesa and J. D. Burrington, US Pat 4,670,395, June 2, 1987.
  • “Method of Making a Diastereomeric Mixture Containing Two Diastereomeric N-acyl Amino Acid Esters,” M.C.Cesa, R.A.Dubbert and J. D Burrington, US Pat 4,721,803, Sept 2, 1987.
  • "a-Amino Acids through Catalytic Reaction of CO and a Hydroxyl Compound with Enamels,” M.C.Cesa and J. D. Burrington, US Pat 4,710,574, July 21, 1987.
  • “Oxidative cyclization of 2-methylglutaronitrile to 3-cyanopyridiene,” US Pat 4,721,789, Sept 21, 1987, R. DiCosimo, R.K. Grasselli and J. D. Burrington.
  • “Method of Producing Adiponitrile,” US Pat 4,681, 968, July 21, 1987, M. W. Blachman, D. T. Tsou and J. D. Burrington.
  • “Preparation of Indenes”, US Pat 4,568,782, M. Pagnotta, M. C. Cesa, and J. D. Burrington, Feb 4, 1986.
  • “Process for Effective Oxidative Dehydrogenation,” R. DiCosimo, R. K. Grasselli and J. D. Burrington, US Pat 4,571,443, Feb 18, 1986
  • “Conversion of a Mixture of 3-Methylpryridene and 3-methylpeperidine to 3-cyanopyridine”, US 4,603,207, July 29, 1986, D. Suresh, R. DiCosimo and J. D. Burrington.
  • “Process for Making Adiponitrile precursors,” US Pat 4,604,244, Aug 5, 1986, R. K. Grasselli, C. T. Kartisek and J. D. Burrington.
  • “Catalytic Dimerization of Acrylonitrile,” M. W. Blachman and J. D. Burrington, U. S. Pat 4,500,468, Feb 18, 1985.
  • “Leach Resistant Catalysts Useful for the Dimerization of Acrylic Compounds,” F.A. Pesa, E.A. Maher, R.K. Grassell and J. D. Burrington, US Pat 4,519,965, May 28, 1985.
  • “Ru-Containing Catalyst Composition Useful for Process For The Dimerization of Acrylic Compounds,” D.T. Tsou, E.A. Maher, R.K. Grasselli and J. D. Burrington, US Pat 4,526,884, June 2, 1985
  • “Method of Making Tri-(B-Cyanoethyl) Amine,” D.T. Tsou and J. D. Burrington, US Pat 4,552,705. Nov 12, 1985.
  • “Improved Process For Making Dimerization Catalysts,” R.K. Grasselli, F.A. Pesa,, E.A. Maher, U. A. Pat 4,560,730, Dec 24, 1985.
  • “Indene Production from Aromatic Olefins”, US 4,374,293, R. K. Grasselli, C. T. Kartisek and J. D. Burrington, Feb 15, 1983.
  • “Acrylic Dimerization Using Supported Catalysts,” R.K.Grasselli, F. A. Pesa, H. F. Hardman and J. D. Burrington, US Pat 4,422,980, Dec 28, 1983.

 

3, Lubricant Additive Chemistries;

  • “Computational Screening of Lewis Acid Catalysts for the Ene Reaction between Maleic Anhydride and Polyisobutylene,” Cristian A. Morales-Rivera, Nico Proust, James, Burrington, and Giannis Mpourmpakis, Ind. Eng. Chem. Res. , 2021, 60, 1, 154–16. https://doi.org/10.1021/acs.iecr.0c04860.
  • James D. Burrington, John Pudelski and James P. Roski, “Challenges in Detergent and Dispersants for Engine Oils.”, in Practical Advances in Petroleum Processing, vol 2, Hsu, Chang S. and Robinson, Paul R., eds., Springer + Business Media, Inc, New York, NY., 2006.
  • “Dispersants Prepared from High Polydispersity Olefin Polymers,” J.R. Johnson, C. J. Kolp, J K Pudelski, Jeffrey G. Dietz, Gregory R. McCullough, Charles K. Baumanis,, Carlos L. Certa de Groote and J. D. Burrington, US Pat 6,500,898, Dec 31, 2002.
  • “Dispersants Prepared from High Polydispersity Olefin Polymers,” J.R. Johnson, J K Pudelski and J. D. Burrington, US Pat 6,407,170, June 18, 2002.
  • Stuart L. Bartley and James D. Burrington, “Domino’ Diels-Alder/Ene reactions for Multifunctionalization of Allylic Aromatics,” Preprints, Division of Petroleum Chemistry, American Chemical Society, vol. 44, no. 3,  pp. 342-344 (July, 1999).

 

 

 

4,   Solid Acid Catalysis for production of lubricant additive products and raw materials, including olefin polymerization, alkylation, and olefin isomerization/regeneration.  These include heteropolyacid-catalyzed reactions for:

  • polymerization of isobutylene to high reactivity polyisobutylene, a key raw material for production of ashless dispersant lubricant additives,
  • alkylation of aromatics including for the production of phenolic and aminic antioxidants, and
  • Production of N-Hydrocarbyl-Substituted Amides, used as specialty commercial surfactants, by Ritter Reaction Using Solid Heteropolyacid Catalysts.

 

Examples of contributions to scientific and patent literature are listed below:

 

  • James D. Burrington, John R. Johnson and John K. Pudelski, “Cationic polymerization using heteropolyacid salt catalysis”, Topics in Catalysis, 23 (1-4), 175-181, August, 2003.
  • “Ammonium Heteropolyacid Catalyzed Polymerization of Olefins,” J.R. Johnson and J.D. Burrington, US Pat 6,346,585, Feb 20, 2002.
  • James D. Burrington, John R. Johnson (both of Lubrizol) and Ronald Mentz (Engelhard Corp.), “Solid Acid atalysis”, Abstracts, American Chemical Society National Meeting, August 21, 22, 2000, Washington, DC
  • James D. Burrington, John R. Johnson and Paul A. Lewis, “Catlytic Isomerization and Dechlorination of Nenes.”  Applied Catalysis A: General, 210 (2001) 192-206.
  • “Catalytic Process for Making High Reactivity Alkylating Agents and Products Resulting Therefrom,” S. L. Bartley, P. A. Lewis, M. B. DeTar, A.L. Kliever, F. A. Del Greco, L. T. Novak and J. D. Burrington, US Pat 5,986,155, Nov 16, 1999.
  • “Heteropolyacid Catalyzed Polymerization of Olefins,” J. R. Johnson and J. D. Burrington, US Pat 5,710,225, Jan 29, 1998.
  • “Process for the Preparation of N-Hydrocarbyl-Substituted Amides Such As Tert-Butylacrylamide Via the Ritter Reaction Using Solid Heteropolyacid Catalysts,” D. C. Rhubright, C. E. Ramey and J. D. Burrington, US Pat 5,712,413, Jan 27, 1998.
  • “Alkylation of Aromatic Amines Using a Heteropolyacid Catalyst,” D. C. Rhubright, P. Y. Zhu and J. D. Burrington, US Pat 5,817,831, Oct 6, 1998.

 

5. Controlled Release (CR) Additive Gel and Microencapsulation Technology.  As the principal discoverer and inventor of this new enabling additive technology, Dr. Burrington established a fundamental working understanding of lubricant additive component gelation and its use as a matrix for controlled release of additives as a means to enhance performance.   (US Patents 6,843,916; 7,000,655; 7,384,896; 7,417,012; 7,534,747and 7,744,660.)  Highlights of Dr. Burrington’s contributions include:

  • “Slow Release Lubricant Additives Gel,” Bruce H. Grasser, Herman F. George, John R. Martin, John K. Pudelski, Barbara L. Soukup, Melinda Bartlett and J. D. Burrington,  US Pat 6,843,916, Jan 18, 2005.
  • “Fluid additive delivery systems,” Gary Garvin and JD Burrington, US Pat 7,000,655, Feb 21, 2006.
  • “Controlled release of additive gel(s) for functional fluids,” Herman F. George, John K. Pudelski, James P. Roski, John R. Martin,  Jennifer M. Ineman,  Gary A. Garvin,  Frank M. van Lier,  David A. McCaughey and J. D. Burrington, US Pat 7,384,896, July 10, 2008.
  • “Slow Release Lubricant Additives Gel,” Bruce H. Grasser, Herman F. George, John R. Martin, John K. Pudelski, Barbara L. Soukup, Melinda Bartlett and J D Burrington, US Pat 7,417,012, Aug 26, 2008.
  • “Gel that Reduce Soot And/Or Emissions from Engines,” Herman F. George, John R. Martin, Ralph E. Kornbrekke and JD Burrington, US Pat 7,534,747, May 190, 2009.
  • “Gel Additives for Fuel the Reduce Soot And/Or Emissions from Engines,” Daniel T. Daly, Herman F. George and JD Burrington, US Pat 7,744,660, June 29, 2010.
  • “Slow Release Lubricant Additives Gel,” Bruce H. Grasser, Herman F. George, John R. Martin, John K. Pudelski, Barbara L. Soukup, Melinda Bartlett and JD Burrington, US Pat 7,799,754, Sept 21, 2010.
  • “Viscosity modifiers in controlled release lubricant additive,” B. Leffel and J.D. Burrington, US Pat 7,833,955, Nov 16, 2010.
  • “Stabilized Blends containing Friction Modifiers”, US Pats 9,175,241 (2015), 9,528,067 (2016), 9,540,581 (2017), 9.631,160 (2017).

 

  1. Textbook and Course. “Industrial Catalysis: Chemistry and Mechanism”:  Dr. Burrington Wrote a catalysis chemistry text for special topics undergraduate and graduate chemistry courses (3-4 credit hours/semester) with this title.  This Textbook presents a chemistry-perspective on the major industrial catalytic processes, including catalyst structure, catalyst preparation reaction chemistries, and catalytic reaction mechanism.   He taught this course at John Carroll University (2002, 2005 and 2013), Case-Western Reserve University (2003-2004), and University of Akron (2004-2005).    The textbook has been published by World Scientific/Imperial College Press, © 2016.