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Synthesis of E,E-dibenzalacetone (E,E-DBA)
Afra ALMashari
5/18/2017
Abstract
The preparation of E,E-dibenzalacetone (Scheme 1), from benzaldehyde and acetone in the presence of ethanol and Ethanolic sodium hydroxide, is described. E,E-dibenzalacetone was purified by recrystallization, E,E-dibenzalacetone was recrystallized from. E,E-dibenzalacetone was obtained in 67.1% yield. The crude and purified products were characterized by melting point determination.
Introduction
The purpose of this experiment was to employ a based-catalyzed aldol condensation in the synthesize of E,E-dibenzalacetone and to characterize the crude and purified samples of E,E-dibenzalacetone by melting point determination. As shown in Scheme 1 this involved allowing benzaldehyde to react with acetone in the presence of ethanol and Ethanolic sodium hydroxide.
../Desktop/lab%20report/Unit%205%20reaction%20scheme.gif Scheme 1
Results
The results of the synthesis of E,E-dibenzalacetone are summarized in Table 1.
Compound
molar
mass (g/mol)
volume/mass moles
yield
Melting point (C)
benzaldehyde (density 1.043 g/mL)
106.2 g/mole
0.25 ml
0.26 g
0.002 mole
N/A
N/A
acetone (density 0.788 g/mL)
580.08 g/mole
0.1 ml
0.07 g
0.001 mole
N/A
N/A
E,E-DBA
(a yellow solid)
234.24 g/mole
N/A
Theoretical
0.234 g
0.001 mole
Literature value
110-111oC
E,E-DBA
(a yellow solid)
234.24 g/mole
N/A
Actual
crude*
0.645 g
63.7%
purified**
0.14 g
67.1
Actual
Crude
109-110 Oc
purified
110-111 Oc
* a yellow solid ** a yellow crystals solid
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