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Encyclopedia Britannica



BENZOPHENONE (DIPIENYL KETONE)

This article appears in Volume V03, Page 757 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: BEC-BER
BENZOPHENONE (DIPIENYL KETONE) , C6H5'COC6H5, the simplest representative of the true aromatic ketones. It may be prepared by distilling
calcium
  benzoate; by condensing benzene with benzoyl chloride in the presence of anhydrous
aluminium
  chloride; by the action of mercury
diphenyl
  on benzoyl chloride, or by oxidizing diphenylmethane with chromic acid. It is a dimorphous substance existing in two enantiotropic forms, one melting at 26 C. and the other at 48 C: (Th. Zincke,Berichte,1871, 4, p. 576). It boils at 306.1 C., under a pressure of 76o.3 2 mm. It is reduced by sodium amalgam to benzhydrol or
diphenyl
  carbinol C6H5CHOHCsH5; a stronger reducing agent, such as hydriodic acid in the presence of amorphous phosphorus converts it into diphenylmethane (C6H5)2.CH2. Potash fusion converts it into benzene and benzoic acid. With phenylhydrazine it forms a hydrazone, and with
hydroxylamine
  an oxime, which exists in one form only; if, however, one of the phenyl groups in the oxime be substituted in any way then two stereo-isomeric
oximes
  are produced (cf. STEREO-
ISOMERISM
 ) ; thus parachlorbenzophenone oxime exists in two different forms (V. Meyer and K. F. Auwers, Berichte, 189o, 23, p. 2403). Many derivatives are known, thus ortho-amino-benzophenone, melting at 1o6 C., can be obtained by reduction of the corresponding nitro compound; it condenses under the
influence
  of heated lead monoxide to an acridine derivative and with
acetone
  in presence of
caustic
  soda it gives a
quinoline
 . Tetramethyl-diamido-benzophenone or Michler's ketone, CO[CsH4N(CH3)2)2, melting at 173, is of technical importance, as by condensation with various substances it can be made to yield dye-stuffs. It is prepared by the action of carbonyl chloride on dimethyl aniline in the presence of
aluminium
  chloride: COC122C6H5N(CH3)2=2HC1+CO[C6H4N(CH3)2]2.


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