Abstract
Benzene was discovered by Faraday in 1825 in compressed oil-gas, but it was not until 1848 that A. W. Hofmann and Mansfield were able to obtain large quantities of it from coal-tar. Just as in the manufacture of coke from coal, it is also formed during numerous other pyrogenic processes, such as for example the destructive distillation of lignite-tar or of petroleum. Of theoretical importance are the formation of benzene by pyrolysis of acetylene according to Berthelot, and the benzene synthesis from pimelic acid by Willstiitter and Hatt.1 Where small quantities of very pure benzene are required even today, the method of choice is that discovered by Mitscherlich in 1833, consisting in the distillation of benzoic acid with lime.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
Reference
Willstätter, R. and Hatt, D., Ber. dtsch. chem. Ges. 45, 1464 (1912).
Gibson, G. E., Blake, N. and Kalm, M., J. chem. Phys. 21, 1000 (1953).
Angus, H. J. F., McDonald Blair, J. and Bryce-Smith, D., J. chem. Soc. 2003 (1960).
Anderton, E. J., Chilton, H. T. J. and Porter, G., Proc. chem. Soc. 352 (1960).
E. I. du Pont de Nemours 000 Co. (Ch. B. Wooster), Amer. Patent 2182242 (1938); Wibant, J. P. and Haak, F. A., Rec. tray. chim. 67, 85 (1948).
Robinson, R. E., Sauve, D. M. and Thomas, O. H., J. Amer. chem. Soc. 76, 631 (1954).
Harries, C. and Weiss, V., Ber. dtsch. chem. Ges. 37, 3431 (1904).
Buchner, E. and Curtius, T., Ber. dtsch. them. Ges. 18, 2377 (1885); Buchner, E. Ber. dtsch. them. Ges. 29, 106 (1896).
Carius, L., Liebigs Ann. 136, 324 (1865).
Steinkopf, W., and Kiihnel, M., Ber. dtsch. chem. Ges. 75, 1323 (1942).
Calingaert, G., Chem. Engng News 29, 3968 (1951); Calingaert, G., Griffing, M. E., Kerr, E. R., Kolka, A. J. and Orloff, H. D., J. Amer. them. Soc. 73, 5224 (1951); J. Amer. them. Soc. 75, 4243 (1953).
Closs, G. L. and Closs, L. E., Tetrahedron Letters 10 (1960).
Doering, W. von E. and Knox, L. H., J. Amer. them. Soc. 72, 2305 (1951).
Angus, H. J. F. and Brice-Smith, D., Proc. chem. Soc. 326 (1959); J. chem. Soc. 479 (1960).
Schenk, G. O. and Steinmetz, R., Tetrahedron Letters 21, 1 (1960).
Bigelow, L. A. and Fukuhara, N., J. Amer. chem. Soc. 63, 2792 (1941).
Wibaut, J. P., van de Lande, L. M. F. and Wallagh, G., Rec. tray. shim. 52, 794 (1933); 56, 65 (1937).
Kekulé, A., Liebigs Ann. 137, 162 (1866).
Friedel, C. and Crafts, J. M., Ann. Chim. (6) 1, 510 (1884).
Clar, E. and John, F., Ber. dtsch. them. Ges. 62, 3021 (1929).
Burton, H. and Frail, U. P. F. G., J. them. Soc. 827 (1953).
Janz, G. J., J. Amer. them. Soc. 74, 4529 (1952).
Profft, E., Drechsler, G. and Oberender, H., Liebigs Ann. 634, 105 (1960).
Bryce-Smith, D. and Turner, E. E., J. chem. Soc. 861 (1953).
Fischer, E. O. and Grubert, H., Z. Naturforsch. 10b, 665 (1955); Fischer, E. O. and Sens, D., Chem. Ber. 89, 1809 (1956); Fischer, E. O. and Stahl, H. O. Chem. Ber. 89, 1805 (1956); Fischer, E. O., Scherer, F. and Stahl, H. O., Chem. Ber. 93, 2065.
Ingold, C. K., Raisin, C. G. and Wilson, C. L., J. chem. Soc. 912 (1936).
Weldon, L. H. and Wilson, C. L., J. chem. Soc. 235 (1946).
Best, A. P. and Wilson, C. L., J. chem. Soc. 239 (1946).
Doering, W. von E., Saunders, M., Boyton, H. G., Earhart, H. W., Wadley, E. F., Edwards, W. R. and Laber, G., Tetrahedron 4, 178 (1958).
van Tamelen, E. E. and Pappas, S. P., J. Amer. chem. Soc. 84, 3789 (1962).
Wittig, G. and Pohner, L., Chem. Ber. 89, 1334 (1956).
Wittig, G. and Benz, E., Tetrahedron 10, 37 (1960).
Berry, R. S., Spokes, G. N. and Stiles, R. M., J. Amer. chem. Soc. 82, 5240 (1960); Friedman, L. and Logullo, F. M., J. Amer. chem. Soc. 85, 1549 (1963).
Wittig, G., Z. Angew. Chem. 69, 245 (1957).
Hopf, H. and Wick, A. K., He shim. Acta 43, 1473 (1960); 44, 19 (1961); Weltin, E., Gerson, F., Murrell, J. N. and Heilbronner, E., Hely. chim. Acta 44, 1400 (1961).
Cook, J. W. and Sehoental, R., J. chem. Soc. 47 (1950).
Emerson, W. S., Lucas, V. E. and Heimsch, R. A., J. Amer. chem. Soc. 71, 1742 (1942).
Willstätter, R. and Pfannenstiel, A., Ber. dtsch. chem. Ges. 37, 4744 (1904).
Nietzki, R. and Benckiser, T., Ber. dtsch. chem. Ges. 18, 504 (1885); Bergel, F., Ber. dtsch. chem. Ges. 62, 490 (1929).
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 1964 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Clar, E. (1964). Benzene. In: Polycyclic Hydrocarbons. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-01665-7_20
Download citation
DOI: https://doi.org/10.1007/978-3-662-01665-7_20
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-662-01667-1
Online ISBN: 978-3-662-01665-7
eBook Packages: Springer Book Archive