Chemistry of Diphenylmethane

Chemistry of Diphenylmethane

Diphenylmethane is an organic compound with the formula (C6H5)2CH2 or C13H12

The compound consists of methane wherein two hydrogen atoms are replaced by
two phenyl groups.

Diphenylmethane forms a common skeleton in organic chemistry; the

diphenylmethyl group is also known as benzhydryl.

Natural Occurring Sources -  1,1'-Methylenebisbenzene has been identified as a

component in crude oils

Synthesis

•       The Friedel-Craft reaction of benzyl chloride with benzene in the presence

of aluminum chloride is an important method for production of
diphenylmethane.

•        Other known catalysts of this process are elemental aluminum, iron(III)

chloride, antimony pentachloride, zinc chloride-hydrogen chloride and boron
fluoride dihydrate.

•       When sulfuric acid is used as a condensation agent diphenylmethane yields

are 83% and with polyphosphoric acid yields are over 90%.
 •        Condensation of benzene with formaldehyde in presence of 85% sulfuric
acid yields 79% diphenylmethane.

benzyl chloride                                     diphenylmethane

•       Prepared from methylene chloride and benzene with aluminum chloride as

catalyst.

Properties of Diphenylmethane:

Molecular Weight: 168.239 g/mol                    

Melting Point - 25.4 deg C         

Odor of oranges

Solubility - Freely soluble in alcohol, ether, chloroform, hexane, benzene; insoluble

in liquid ammonia

Summary

•       Diphenylmethane is an organic compound with the formula

(C6H5)2CH2 or C13H12

•       1,1'-Methylenebisbenzene has been identified as a component in crude oils

•       Synthesised through Friedel-Craft reaction