1. CONVERSION OF ACETONE
TO MESITYLENE USING AL2O3
CATALYST
Kathleen Brown
Elcriton Internship
Summer 2015

2. WHAT’S THE GOAL?
 Create the most efficient catalyst to yield the highest amount of
Mesitylene (at least 90%) via the following reaction
 Create a catalyst that breaks down as slowly as possible
3  3 +

3. WHAT IS MESITYLENE USED FOR?
 Precursor to 2,4,6- trimethylamine which is used in colorants
 Additive in some aviation gasoline blends
 Specialty solvent – used in electronics as a developer for
photopatternable silicones
 Ligand in organometallic chemistry

4. STEP 1:
 Create a calibration curve for Mesitylene in methanol
Area = 1464.8(wt% mesitylene)
R² = 0.9864
0.0
2000.0
4000.0
6000.0
8000.0
10000.0
12000.0
0 1 2 3 4 5 6 7 8
Area
Wt % mesitylene
Calibration Curve (Mesitylene in Methanol)

5. STEP 2
 Gather “baseline” data using a common, unmodified, store-
bought solid phase catalyst, Al2O3
 We predict that this catalyst will become less efficient over
time and will have a low conversion of acetone to
mesitylene

6. PROCEDURE
1. First, Acetone is sent through small plastic
tubing at 3 mL/min into metal piping past a
pressure gauge and into…
2. A heated reactor, full of the chosen catalyst.
The reactor is heated via “electrically
charged tape” at about 370 C
3. Once the acetone leaves the reactor, it is
sent through metal piping and down into a
250 mL rounded flask where the hot vapors
are condensed in the condenser which is
attached to a chiller set at 1 C
4. Any vapors that make it through the airtight
system can be seen escaping in the ( I don’t
know what its called)

7. RESULTS
Run 1
 The reaction produced a yellow solution with
two layers: water and organic material
 Organic layer consisted of 16.6% mesitylene
 Acetone converted to mesitylene: 11.6% (2.04
of 25.48 g)
 Unreacted acetone: 0.44 g
 5.9 g unaccounted for in mass balance
Run 2
 Reaction produced a brown solution with
two layers
 Organic layer consisted of 10.4% mesitylene
 Acetone converted to mesitylene: 8.4% (1.76
of 29.24 g)
 Unreacted acetone: 1.47 g
 4.0 g unaccounted for in mass balance
 This yield produced 40% less mesitylene in
the organic layer than Run 1

8. RESULTS
Run 3
 Reaction produced a brown solution with
two layers
 Organic layer consisted of 10.1% mesitylene
 Acetone converted to mesitylene: 9.9% (2.11
of 30.83 g)
 Unreacted acetone: 1.76 g
 3.3 g unaccounted for in mass balance
 This yield produced 3% less mesitylene in the
organic layer than Run 2
Run 4
 Reaction produced a dark brown solution
with two layers
 Organic layer consisted of 7.0 % mesitylene
 Acetone converted to mesitylene: 7.8%
(1.61of 30.11 g)
 Unreacted acetone: 1.34 g
 2.69 g unaccounted for in mass balance
 This yield produced 30% less mesitylene in
the organic layer than Run 3

9. 0.00%
2.00%
4.00%
6.00%
8.00%
10.00%
12.00%
14.00%
16.00%
18.00%
1 2 3 4
%Mesitylene
Run #
% Mesitylene in Organic Layer Over Time
0.00
2.00
4.00
6.00
8.00
10.00
12.00
14.00
1 2 3 4
%Conversion
Run #
% Acetone Converted to Mesitylene Over Time
0.00
0.50
1.00
1.50
2.00
0 0.5 1 1.5 2 2.5 3 3.5 4 4.5
WtAcetone(g)
Run #
Unreacted Acetone Over Time
RESULTS

10. STEP 3
Create a new modified catalyst
 93.20 g Al2O3 mixed with 55.93 g ethanol
+
 4.66 g Niobium V Chloride mixed in 45.80 g ethanol (Reaction takes place)
 Heat & flush with N2 until dry

11. RESULTS
Run 1
 Reaction produces a blue water layer and a
light brown, transparent organic layer
 10.7% of the acetone was converted to 2.02 g
mesitylene
 Only 0.066 g acetone was left over in the
organic layer
 Organic layer consists of 20.1% mesitylene

12. RESULTS
Run 2
 Reaction produces a light blue water
layer and a brown, transparent organic
layer
 9.6% of the acetone was converted to
2.04 g mesitylene
 0.607 g acetone was left over in the
organic layer
 Organic layer consists of 13.6%
mesitylene
 This is a 10.6% decrease in mesitylene
production from Run 1
Run 3
 Reaction produces a clear-yellow water
layer and a brown organic layer
 8.3% of the acetone was converted to
1.75 g mesitylene
 0.681 g acetone was left over in the
organic layer
 Organic layer consists of 10.54%
mesitylene
 This is a 13.9% decrease in mesitylene
production from Run 2

13. RESULTS
Run 4
 Reaction produces a clear-yellow water
layer and a brown organic layer
 6.4 % of the acetone was converted to
1.28 g mesitylene
 0.776 g acetone was left over in the
organic layer
 Organic layer consists of 6.78%
mesitylene
 This is a 22.7% decrease in mesitylene
from Run 3
Run 5
 Reaction produces a clear-yellow water
layer and a yellow-brown organic layer
 8.1% of the acetone was converted to
2.74 g mesitylene
 2.059 g acetone was left over in the
organic layer
 Organic layer consists of 8.64%
mesitylene
 This is a 27.1% increase in mesitylene
from Run 4

14. RESULTS
Run 6
 Reaction produces a clear-yellow water
layer and a brown organic layer
 6.7% of the acetone was converted to
2.74 g mesitylene
 1.575 g acetone was left over in the
organic layer
 Organic layer consists of 7.2%
mesitylene
 This is a 17.9% decrease in mesitylene
from Run 5
Run 7
 Reaction produces a clear-yellow water
layer and a brown organic layer
 6.0% of the acetone was converted to
1.30 g mesitylene
 1.94 g acetone was left over in the
organic layer
 Organic layer consists of 5.8%
mesitylene
 This is a 9.5% decrease in mesitylene
from Run 6

15. RESULTS
Run 8
 Reaction produces a clear-yellow water
layer and a brown organic layer
 6.6% of the acetone was converted to
1.32 g mesitylene
 1.68 g acetone was left over in the
organic layer
 Organic layer consists of 6.6%
mesitylene
 This is a 9.0% increase in mesitylene
from Run 7
0.00%
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15.00%
20.00%
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0 1 2 3 4 5 6 7 8 9
%mesitylene
Run #
% mesitylene in organic layer over time
0.00%
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0 1 2 3 4 5 6 7 8 9
% conversion of acetone to mesitylene