The document describes experiments to develop an efficient catalyst for converting acetone to mesitylene. Initial experiments used an unmodified Al2O3 catalyst, which became less effective over time, producing decreasing yields of mesitylene from 11.6% to 7.8%. A modified catalyst was then created by adding niobium chloride to Al2O3. This catalyst had varying effectiveness over 8 runs, with mesitylene yields ranging from 20.1% to 5.8% and decreasing over time as the catalyst broke down. The goal was to create a catalyst that yields at least 90% mesitylene and breaks down slowly over multiple conversions.

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
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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%
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18.00%
1 2 3 4
%Mesitylene
Run #
% Mesitylene in Organic Layer Over Time
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%Conversion
Run #
% Acetone Converted to Mesitylene Over Time
0.00
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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
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%mesitylene
Run #
% mesitylene in organic layer over time
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% conversion of acetone to mesitylene