Chemical Properties
1,3-Diphenyl-2-propanone has a sweet, faint, fruity odor reminiscent of bitter almond
Physical properties
White crystals or colorless crystalline mass. M.P. 40°C. B.P. 331°C.
1,3-Diphenylacetone is almost insoluble in water, soluble in alcohol
and oils, poorly in Propylent glycol.
Sweet, but rathtr faint, fruity-almondy odor
of considerable tenacity.
Uses
1,3-Diphenylacetone is used in the aldol condensation reaction with benzil (a dicarbonyl) and base to create tetraphenylcyclopentadienone.
Preparation
By heating α,?α’-phenyl benzyl ethylene glycol or α,?α’-phenyl benzyl ethylene oxide in the presence of diluted H2SO4
or ZnCl2; also by dry distillation of phenylacetate and magnesium chloride (C6H5CH2COOMgCl) or other salts of phenylacetic acid.
Application
1,3-Diphenylacetone is occasionally used as a trace ingredient in
floral perfums compositions, Fougere types,
New Mown Hay, etc. wh:re it can act as a
modifier for Coumarin, making its odor softer.
Used in fruit flavor compositions, and in
imitation Honey, Nut, etc. - mostly in tracss
only.
Definition
ChEBI: 1,3-Diphenyl-2-propanone is an aromatic compound.
Aroma threshold values
Aroma characteristics at 10% in ethanol. Sweet, powdery, and honey with floral rose nuances
Taste threshold values
Taste characteristics at 30 ppm: bitter with floral, rose and honey notes.
Synthesis Reference(s)
The Journal of Organic Chemistry, 33, p. 869, 1968
DOI: 10.1021/jo01266a094
Purification Methods
Fractionally crystallise it from its melt, then crystallise it from pet ether. Store it in the dark. [Beilstein 7 IV 1420.]
