Chemistry of Diphenylmethane

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

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