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BENZOPHENONE (DIPIENYL KETONE)

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Originally appearing in Volume V03, Page 757 of the 1911 Encyclopedia Britannica.
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BENZOPHENONE (DIPIENYL KETONE) , See also:C6H5'CO•C6H5, the simplest representative of the true aromatic See also:ketones. It may be prepared by distilling See also:calcium benzoate; by condensing See also:benzene with benzoyl chloride in the presence of anhydrous See also:aluminium chloride; by the See also:action of See also:mercury See also:diphenyl on benzoyl chloride, or by oxidizing diphenylmethane with chromic See also: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 See also:sodium See also:amalgam to benzhydrol or diphenyl carbinol C6H5•CHOH•CsH5; a stronger reducing See also:agent, such as hydriodic acid in the presence of amorphous See also:phosphorus converts it into diphenylmethane (C6H5)2.See also:CH2. Potash See also:fusion converts it into benzene and benzoic acid. With phenylhydrazine it forms a See also:hydrazone, and with See also:hydroxylamine an oxime, which exists in one See also:form only; if, however, one of the phenyl See also:groups in the oxime be substituted in any way then two stereo-isomeric See also:oximes are produced (cf. STEREO-See also:ISOMERISM) ; thus parachlorbenzophenone oxime exists in two different forms (V. See also: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 See also:

compound; it condenses under the See also:influence of heated See also:lead monoxide to an See also:acridine derivative and with See also:acetone in presence of See also:caustic soda it gives a See also:quinoline. Tetramethyl-diamido-benzophenone or Michler's ketone, CO[CsH4N•(See also: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 See also:aniline in the presence of aluminium chloride: COC12±2C6H5N(CH3)2=2HC1+CO[C6H4N(CH3)2]2.

End of Article: BENZOPHENONE (DIPIENYL KETONE)

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