The Reaction of Carbon-14-Labeled Reagents with Coal

  • Clair J. Collins
  • Vernon F. Raaen
  • Cherie Hilborn
  • W. Howard Roark
  • Paul H. Maupin


The reasons for carrying out the research presented here were threefold: 1) to allow carbon-14-labeled reagents to react with coal and with coal-derived materials at low temperatures and thus to estimate a) the reagents1 value in determining which functions are present in the original coal or b) have been added or removed during coal reactions; 2) to allow carbon-14-labeled compounds (containing structures similar to those known to be present in coal) to react with coal at or above 400°, then to determine the fates of these compounds using the carbon-14 as a tracer. In this way it was hoped conclusions could be drawn as to how the same kind of moiety behaves in the coal structure; and 3) to elucidate the mechanisms of the thermal reactions of the above-mentioned labeled compounds with coal.


Ball Mill Carbon Capture Bituminous Coal Sulfonyl Chloride Benzene Sulfonyl 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    W. Fuchs and W. Stengel, Hydroxyl and Carboxyl Groups in Humic Acids, Brennst.-Chem. 10:303 (1929); W. Fuchs and A. G. Sandhoff, Investigations Concerning Hydroxycarboxylic Acids from Bituminous Coals, FUEL 19: 45 (1940).Google Scholar
  2. 2.
    L. Blom, L. Edelhausen, and D. W. van Krevelen, Chemical Structure and Properties of Coal XVII. Oxygen Groups in Coal and Related Products, FUEL 36: 135 (1957).Google Scholar
  3. 3.
    P. H. Given, The Reactivity of Coal in Organic Chemical Reactions, Brennst.-Chem. S. Bd 39: 14 (1958).Google Scholar
  4. 4.
    T. L. Gilchrist and C. W. Rees, “Carbenes, Nitrenes and Arynes,”Meredeth Corporation, New York (1969).Google Scholar
  5. 5.
    W. Kirmse, “Carbene Chemistry,” Academic Press, New York (1964), 2d Edition (1971).Google Scholar
  6. 6.
    J. Hine, “Divalent Carbon,” Ronald Press, New York (1964).Google Scholar
  7. 7.
    D. Seyferth, Phenyl(trihalomethyl)mercury Compounds: Exceptionally Versatile Dihalocarbene Precursors, Acc. Chem. Res. 5: 65 (1972).CrossRefGoogle Scholar
  8. 8.
    D. W. van Krevelen, Coal as Plant Debris and Functional Group Analysis in “Coal,” Elsevier, Amsterdam (1972).Google Scholar
  9. 9.
    B. M. Benjamin, E. W. Hagaman, V. F. Raaen, and C. J. Collins, Pyrolysis of Tetralin, FUEL 58: 386 (1979).CrossRefGoogle Scholar
  10. 10.
    B. M. Benjamin, V. F. Raaen, P. H. Maupin, L. L. Brown, and C. J. Collins, Thermal Cleavage of Chemical Bonds in Selected Coal-Related Structures, FUEL 57: 269 (1978).CrossRefGoogle Scholar
  11. 11.
    C. J. Collins, V. F. Raaen, B. M. Benjamin, P. H. Maupin, Coal Chemistry. Reactions of Tetralin with Coal and with Some Carbon-14-Containing Compounds, J. Amer. Chem. Soc. 101: 5009 (1979).CrossRefGoogle Scholar
  12. 12.
    R. D. H. Heard, J. R. Jamieson, and S. Salomon, The Synthesis of Methylamine-1C and Diazomethane-14C, J. Amer. Chem. Soc. 73: 4985 (1951).CrossRefGoogle Scholar
  13. 13.
    C. H. Shuford, Jr., D. L. West, and H. W. Davis, Allylic Rearrangement of Hexachloropropene-1-14C, J. Amer. Chem. Soc. 76: 5803 (1954).CrossRefGoogle Scholar
  14. 14.
    C. J. Collins, Carbon-14 Synthetic Studies. 2-Methyl-l,4-Naphthoquinone-8-14C, J. Amer. Chem. Soc. 73: 1038 (1951).CrossRefGoogle Scholar
  15. 15.
    D. F. Othmer, J. J. Jacobs, Jr., and W. J. Bushmann, Sulfonation of Naphthalene, Ind. Eng. Chem. 35: 326 (1943).CrossRefGoogle Scholar
  16. 16.
    C. E. May, Beta Naphthol, J. Amer. Chem. Soc. 44: 650 (1922).Google Scholar
  17. 17.
    F. Wilson and K. H. Meyer, Die Überführung aromatischer Sulfosäuren in Phenole, F. Wilson, K. H. Meyer, Ber der deutsch. Chem. Ges. 47: 3160 (1914).CrossRefGoogle Scholar
  18. 18.
    H. T. Clark, G. C. Babcock and T. F. Murray, Benzene Sulfonyl Chloride, in “Organic Syntheses,” Collective Volume I, p. 85, H. Gilman, Ed. J. Wiley & Sons, Inc., New York (1941).Google Scholar
  19. 19.
    H. S. Turner and R. J. Warne, Benzene-14C in “Organic Syntheses with Isotopes,” p. 820, Part I, A. Murray III and D. L. Williams, Eds., Interscience Publishers, Inc., New York (1958).Google Scholar
  20. 20.
    R. Adams and C. S. Marvel, Thiophenol, in “Organic Syntheses,”Collective Volume I, p. 504, H. Gilman, Ed., J. Wiley & Sons, New York (1958).Google Scholar
  21. 21.
    V. F. Raaen, G. A. Ropp, and H. P. Raaen, Carbon-14, McGraw-Hill Book Co., New York, page 240 (1968).Google Scholar

Copyright information

© Plenum Press, New York 1982

Authors and Affiliations

  • Clair J. Collins
    • 1
  • Vernon F. Raaen
    • 1
  • Cherie Hilborn
    • 1
  • W. Howard Roark
    • 1
  • Paul H. Maupin
    • 1
  1. 1.Chemistry DivisionOak Ridge National LaboratoryOak RidgeUSA

Personalised recommendations