urbaf2

(Michael S) #1

470 CHEMISTRY AND TECHNOLOGY OF EXPLOSIVES


NITRO DERIVATIVES OF FLUOROBENZENE


The most important nitro derivatives of fluorobenzene are:


m. p. 27°C m. p. 25.8°C m. p. 35°C

The nitration of fluorobenzene was studied by a number of authors. Most of
the earlier work was devoted to mononitration (Wallach [44], Hollernan [45],


Swarts [46]).


Dinitration to obtain 1,2,4-fluorodinitrobenzene was described by Holleman


and Beekman [47] who nitrated p- fluoronitrobenzene. Zahn and A. Würz [48]


prepared the same dinitrocompound by nitrating fluorobenzene. 1,2,4,6-Fluorotrini-


trobenzene (picryl fluoride) was prepared by Olah, Pavlath, J. Kuhn and Varsanyi


[49] by acting on 1,2,4-fluorodinitrobenzene with a nitrating mixture composed


of fuming nitric acid and 60% oleum. The yield was 36% of theoretical.


LITERATURE


  1. F. SANGER, Biochem. J. 44, 126; 45, 563 (1949).

  2. C. K. INGOLD and M. L. BIRD, J. Chem. Soc. 1938, 918.

  3. R. B. SANDIN and J. R. L. WILLIAMS, J. Am. Chem. Soc. 69, 2747 (1947).
    3a. J. D. ROBERTS, J. K. SANFORD, F. L. J. SIXMA, H. CERFONTAIN and R. ZAGT, J. Am.
    Chem. Soc. 76, 4525 (1954).

  4. A. LAPWORTH and R. ROBINSON, Mem. Proc. Manchester Lit. and Phil. Soc. 72, 43 (1928).

  5. C. K. INGOLD in E. H. RODD (Ed.), Chemistry of Carbon Compounds, Vol. III A, p. 36,
    Elsevier, Amsterdam, 1954.

  6. A. RICHE, Ann. 121, 358 (1862).

  7. N. SOKOLOV, Jahresber. 1866, 551.

  8. A. F. HOLLEMAN and B. R. de BRUYN, Rec. trav. chim. 19, 95, 189 (1900).

  9. JUNGFLEISCH, Ann. Chim. [4], 15, 231 (1868).

  10. A. LAUBERHEIMER, Ber. 7, 1765 (1874); 8, 1623 (1875); 9, 760 (1876).

  11. I. I. OSTROMYSLENSKII, J. prakt. Chem. 2, 78, 261 (1908).

  12. Griesheim Chemische Fabrik, Ger. Pat. 78309 (1894).

  13. H. MCCORMACK, Ind. Eng. Chem. 19, 1333 (1927).

  14. B. B. DEY et al., J. Sci. Ind. Res. (India) 3, 95 (1944).

  15. H. H. BIEBER and W. F. SCHURIG, Ind. Eng. Chem. 49, 832 (1957).

  16. N. V. LAZAREV, Khimicheskiye vrednyye veshchestva, Goskhimiidat, Moskva-Leningrad, 1951.

  17. R. MULLER, Z. physik. Chem. 86, 223 (1914).

  18. L. DESVERGNES, Mém. poudres. 19, 217, 269 (1918-1922); 25, 3, 291, 507, 1271 (1931); Chimie
    et industrie 25, 3, 291 (1931).

Free download pdf