Summary
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1.
The thermal transformations of trichloroethylene at high pressures we investigated. Under the conditions studied the main products of the process were 1,1,2,4,4-pentachloro-l,3-butadiene and, in a smaller amount, 1,1,1,3-tetrachloroethane.
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2.
The thermal transformations of trichloroethylene are greatly accelerated by pressure. At a pressure of 25,000 atm reaction at 190° becomes self-accelerating and leads to partial carbonization of the material. The temperature at which self-acceleration of the reaction occurs rises as the pressure is lowered.
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3.
A possible radical-chain scheme is discussed for the dimerization of trichloroethylene under the conditions studied.
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Literature cited
O. Nicodemus, J. prakt. Chem. 83, 312 (1911).
C. E. Frank and A. U. Blackham, J. Amer. Chem. Soc. 72, 3283 (1950).
O. Simamura and N. Inamoto, Bull. Chem. Soc. Japan 27, 152 (1954).
French Pat. 814423, 1937; Chem. Abstrs. 32, 957 (1938).
British Pat, 473644, 1937; Chem. Abstrs. 32, 2958 (1938).
Röhm and Haas, French Pat. 841728, 1939. Chem. Abstrs. 34, 4395 (1940).
German Pat. 718057, 1942; Chem. Abstrs. 38, 2343 (1944).
German Pat. 736232, 1943; Chem. Abstrs. 38, 2972 (1944).
H. Mugdan and I. Wimmer, U. S. Pat. 2338297, 1944; Chem. Abstrs. 38, 3668 (1944).
K. H. Klaassens and I. H. Gisolf, J. Polymer, Sci. 10, 149 (1953).
M. G. Gonikberg, V. M. Zhulin and V. P. Butuzov, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1956, 730.
M. G. Gonikberg and V. M. Zhulin, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1957, 510.
I. H. Mathews, J. Amer. Chem. Soc. 48, 569 (1926).
J. Timmermans, Physicochemical constants of pure organic compounds, N. Y., 1950.
A. Roedig, Liebigs, Ann. Chem. 574, 122 (1951).
E. Erdmann, J. prakt. Chem. 85, 78 (1912).
F. Kaufler, Liebigs Ann. Chem. 433, 48 (1923).
J. Y. Krynitzky and H. W. Carhart, J. Amer. Chem. Soc. 71, 816 (1949).
O. Fruhwirth, Ber. 74, 1700 (1941).
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Gonikberg, M.G., Zhulin, V.M. Thermal transformations of trichloroeth ylene at high pressures. Russ Chem Bull 8, 882–887 (1959). https://doi.org/10.1007/BF00915920
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DOI: https://doi.org/10.1007/BF00915920