Acetone - Mesitylene Al2O3 catalyst

1. Conversion of Acetone to Mesitylene Using Al 2 O 3 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

5. Step 2 Gather “baseline” data using a common, unmodified, store-bought solid phase catalyst , Al 2 O 3 We predict that this catalyst will become less efficient over time and will have a low conversion of acetone to mesitylene

6. Procedure First, Acetone is sent through small plastic tubing at 3 mL/min into metal piping past a pressure gauge and into… A heated reactor, full of the chosen catalyst. The reactor is heated via “electrically charged tape” at about 370 C 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 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 A cetone 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. RESULTS

10. Step 3 Create a new modified catalyst 93.20 g Al 2 O 3 mixed with 55.93 g ethanol + 4.66 g Niobium V Chloride mixed in 45.80 g ethanol (Reaction takes place) Heat & flush with N 2 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