Synthesis of Dibenzalacetone

Escobar, Camille
I. Introduction

Dibenzalacetone is an organic molecule with the formula C17H14O that is also known as
dibenzylideneacetone. This yellow crystalline solid substance is utilized as a catalyst. However,
it is extensively used in sunscreens since it absorbs UV light. Dibenzalacetone is a conjugated
ketone and alkene that absorbs UV radiation well. Claisen-Schmidt condensation can be used
to manufacture dibenzalacetone because this molecule contains a ketone. Claisen-Schmidt
condensation is a reaction between an aldehyde or ketone with aliphatic hydrogen and a
carbonyl molecule, specifically an aromatic compound without aliphatic hydrogen. This is a
condensation reaction that produces beta-hydroxy carbonyl molecules. This reaction occurs
when a base catalyzes a cross aldol condensation between an aromatic aldehyde and an
aliphatic ketone. In contrast, aldol condensation is a reaction between an enol or enolate ion
and a carbonyl molecule. This reaction is followed by dehydration and recrystallization. This
experiment requires acetone, benzaldehyde, and sodium hydroxide to perform the reaction. The
reactions occur when an aromatic aldehyde reacts with an alkali by condensation with an
aliphatic hydrogen-containing ketone. The elimination of the water molecule results in the
condensation of aldehydes with the ketone. In accordance with this, benzaldehyde condenses
with acetaldehyde and acetone to produce the desired product, dibenzalacetone. The reaction
for the synthesis of dibenzalacetone is shown below:

The purpose of this study is to synthesize dibenzalacetone via Claisen-Schmidt

condensation and cross aldol condensation using benzaldehyde and acetone in the presence of
sodium hydroxide.

II. Materials used

Table 1. List of Apparatus

Apparatus Quantity

Beaker, 100 mL 1

Beaker, 50 mL 3

Evaporating dish 1

Glass rod 1

Pipette 1

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 Thermometer 1

Erlenmeyer flask 1

Funnel 1

Filter paper 1

Tissue paper 1

Table 2. List of Chemicals and Reagents

Chemical/Reagents Quantity

Benzaldehyde 3.2 mL

Acetone 2.3 mL

Sodium hydroxide 3.15 g

Ethanol 25 mL

Distilled water 30 mL

Ice cubes -

III. Procedure in paragraph form

To start with the synthesis, 3.15g of sodium hydroxide (NaOH) was measured and
placed in a beaker. The beaker containing the NaOH was placed in an ice bath. 25-mL of ethyl
alcohol was added to the beaker, followed by the addition of 30-mL distilled water. After adding
the ethyl alcohol and the distilled water with NaOH, it was mixed until the NaOH was dissolved.
After this, 3.2-mL benzaldehyde was transferred to another beaker through the use of a pipette,
then 3.2-mL acetone was added and mixed using a glass rod. Half of the mixture was
transferred slowly into the NaOH solution with the use of a pipette and was also mixed
vigorously. Upon transferring the mixture, the temperature was recorded to make sure it is below
20C. Transfer of the mixture was continued and was mixed for 1-2 minutes. A white precipitate
was formed and was continued to be stirred for another 15 minutes. The other half of the
mixture was added to the solution with gentle stirring and after 30 minutes of stirring, the
solution was filtered through the gravity filtration method. When the filtration was completed, the
precipitate compound was washed with ice-cold water and was transferred to a tissue paper in
order to dry. Lastly, the precipitate was purified through the recrystallization process.

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IV. Procedure in a schematic diagram

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 V. Discussion

In the experiment, procedures such as the ice bath, temperature monitoring, and
washing with ice-cold water were applied. This study includes a brief explanation of this topic in
order to facilitate a deeper understanding of the various processes. First, an ice bath is used to
maintain the low temperature of a solution or mixture; in this experiment, the low temperature of
the NaOH solution was maintained. This is due to the fact that NaOH is capable of gaining a
great deal of heat energy, which can cause the solution to be hot or be at a high temperature. In
addition, vigorous stirring was required for efficient mixing and constant contact between the
components. In addition, ice-cold water was utilized during the washing process to preserve the
precipitate's form. Ice-cold water prevents precipitation from melting or altering its shape. In
addition, the final step of the experiment was recrystallization. This was done in order to purify
the precipitate and reconstruct the crystals.

VI. MSDS of chemicals

Material Safety Data Sheets

PHYSICO-CHEMICAL CHARACTERISTICS, HAZARDS, PRECAUTIONARY MEASURES, AND WASTE

DISPOSAL METHODS OF CHEMICAL/REAGENTS

Table 1: Synthesis of dibenzalacetone

Chemical Physical Chemical Hazards Precautionary Waste

Name Characteristics Characteristics Measures Disposal
Methods

Benzaldehyde Yellow, liquid, Chemical Combustible Use proper Dispose of

bitter-almond Stability: Stable. liquid and personal material in
odor, vapor. protective accordance
Boiling Point: Harmful if equipment. with all
178 deg C, swallowed. Avoid runoff applicable
Freezing/Meltin Causes into storm local, state, and
g Point: -56 deg digestive and sewers and federal
C respiratory ditches which regulations.
tract irritation. lead to
Causes eye waterways.
and skin Use water
irritation. It spray to
may cause disperse the
central gas/vapor.
nervous Remove all
system sources of
depression. It ignition.
may cause
kidney
damage.

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Acetone Liquid, clear, Stable at room Extremely Use proper Dispose of
colorless, temperature in flammable personal material in
sweetish odor, closed liquid and protective accordance
Boiling Point: containers vapor. Vapor equipment. with all
56.5 deg C, under normal may cause void runoff into applicable
Freezing/Meltin storage and flash fire. storm sewers local, state, and
g Point:-94 deg handling Causes eye and ditches federal
C conditions. irritation. which lead to regulations.
Breathing waterways.
vapors may Wear
cause appropriate
drowsiness protective
and dizziness. clothing to
Causes minimize
respiratory contact with
tract irritation. skin. Remove
Aspiration all sources of
hazard if ignition.
swallowed. Provide
Can enter ventilation. A
lungs and vapor
cause suppressing
damage. foam may be
Prolonged or used to reduce
repeated vapors.
contact may Wash
dry the skin thoroughly after
and cause handling.
irritation.

Sodium Solid, white, Stable at room Causes eye Use proper Dispose of
hydroxide odorless, temperature in and skin personal material in
Boiling Point: closed burns. Causes protective accordance
1390 deg C @ containers digestive and equipment. with all
760 mmHg, under normal respiratory Vacuum or applicable
Freezing/Meltin storage and tract burns. sweep up local, state, and
g Point:318 deg handling Hygroscopic material and federal
C conditions. (absorbs place it into a regulations.
moisture from suitable
the air). disposal
container.
Avoid runoff
into storm
sewers and
ditches which
lead to
waterways.
Clean up spills
immediately,

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 observing
precautions in
the Protective
Equipment
section. Avoid
generating
dusty
conditions.
Provide
ventilation. Do
not get water
on spilled
substances or
inside
containers.

Ethanol Clear liquid, Stable under Causes Use proper Dispose of

colorless, Mild, normal severe eye personal material in
rather pleasant, temperatures irritation. protective accordance
like wine or and pressures. Flammable equipment. with all
whis, liquid and Remove all applicable
Boiling Point: 78 vapor. Causes sources of local, state, and
deg C, respiratory ignition. Use a federal
Freezing/Meltin tract irritation. spark-proof regulations.
g Point:-114.1 This tool. Provide
deg C substance has ventilation. A
to caused vapor
adverse suppressing
reproductive the foam may
and fetal be used to
effects in reduce vapors.
humans. may
cause central
nervous
system
depression.
May cause
liver, kidney
and heart
damage.
Causes
moderate skin
irritation.

Water, H₂O Colorless liquid, Stable at room This material Keep container Dispose of
clear, odorless, temperatures in is not closed. material in
Boiling Point: closed hazardous Protective accordance
100 deg C, containers under normal gloves and with all
Melting point: under normal handling and apron are applicable

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 0ºC (32ºF) and storage recommended. local, state, and
recommended conditions. federal
storage and use When heated regulations.
conditions to boiling,
steam and
liquid contact
can cause
burns to skin
and mucous
membranes.

VII. References

Acetone; MSDS No. 00140 [Online]; Fisher Scientific, 2008.

https://fscimage.fishersci.com/msds/00140.htm

Benzaldehyde; MSDS No. 02590 [Online]; Fisher Scientific, 2003.

https://fscimage.fishersci.com/msds/02590.htm

Ethanol; MSDS No. 89308 [Online]; Fisher Scientific, 2003.

https://fscimage.fishersci.com/msds/89308.htm

LabChem. (2020, June 26). Water. Retrieved from

http://www.labchem.com/tools/msds/msds/LC26750.pdf

Sodium hydroxide; MSDS No. 21300 [Online]; Fisher Scientific, 2008.

https://fscimage.fishersci.com/msds/21300.htm

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