This experiment aimed to synthesize benzaldehyde through catalytic oxidation of benzyl alcohol using manganese oxide. Manganese oxide was first synthesized by oxidizing potassium permanganate and ferrocene in sulfuric acid. Benzyl alcohol, toluene, and manganese oxide were then heated to perform the catalytic oxidation. X-ray diffraction testing found the manganese oxide was in an amorphous phase. Gas chromatography was used to analyze the products and found the amorphous phase manganese oxide had higher conversion of benzyl alcohol to benzaldehyde than the gamma phase. In conclusion, the experiment successfully synthesized benzaldehyde through catalytic oxidation using manganese oxide as hypothesized.

1. By Joseph and Bam Manganese Oxide for Catalytic Oxidation of Benzyl Alcohol

2. The Lab Team

4. Outline of the Experiment KMnO4 + H2SO4 MnO2 Part 1 MnO2 + Toluene + Benzyl Alcohol Part 2 Benzaldehyde!!!

5. Purpose The purpose of this experiment is to perform catalytic oxidation reaction in order to get a product of Benzaldehyde with high selectivity. The oxidation of alcohols to the corresponding carbonyl compounds is a key reaction in organic synthesis. Hypothesis We hypothesized that the Benzaldehyde can be synthesize through a series of oxidation reaction. The reason for making such Hypothesis is based on my Chemistry class understanding on chemical reactions and filtration.

7. KMnO4 (0.1 M)

8. Fe(C5H5)2 (20 mg)

9. H2SO4 (0.5 ml)

10. Water

11. Round Bottom Flask

12. Pipette

13. Filter paper

14. Funnel

15. Benzyl alcohol (0.1034 l)

16. Toluene (10 ml)

17. Condenser

19. Results and Analysis

20. Formation of the Manganese (IV) Oxide KMnO4 + H2SO4 MnO2 The manganese oxide was synthesized by the oxidation of manganese sulfate with potassium permanganate in an acidic medium at room temperature. This was formed by 0.3951 grams of potassium permanganate, 20 mg of ferrocene, and 0.5 ml of sulfuric acid, and 25 ml of water. First, we added the sulfuric acid to the ferrocene. The solution turned from orange to green color. After adding water to it, the color becomes purple. Then, we carefully added potassium permanganate into the solution. We waited for the KMnO4 solution to evaporate as it stirred constantly and placed under a hot plate. The color eventually changed from purple to brown. After that, we filtered the solution with the filtering apparatus.

21. OxidizingBenzyl Alcohol The catalytic oxidation of benzyl alcohol was carried out in a round-bottom flask with a condenser and magnetic stirrer. In the round-bottom flask are benzyl alcohol (0.1034 g), toluene (10 g), and the manganese oxide we previously filtered (100mg). As seen in the pictures, the condenser is connected to a cooling aid to prevent the solution from evaporating. Also, tissues are used to cover around the tube to prevent water from going in. After waiting for approximately 3 hours, we took the flask for a cool down under ice water and filtered the solution. During the filtration, we added sodium sulfate to absorb the water. The filtration process continues as the solution is being filtered with a micro-optic filter paper. Benzyl Alcohol + Toluene + MnO2

22. X-ray diffraction (XRD) is a versatile, non-destructive technique that reveals detailed information about the chemical composition and crystallographic structure of the solution. It is widely used in chemistry and biochemistry to determine the structures of molecules. This test was performed to find out what phase our MnO2 solution is in. To start the test, we first have to place the solution onto a glass piece. After that, we place the piece onto the holder which is located in the middle. Laser beams then shoot out at many angles. During this test, the indicator is set from 20-80 degree with increment of 1.7. In conclusion to the test, we found out that the solution is in its amorphous phase. We will later compare the efficiency between the amorphous phase and the gamma phase with the gas chromatography test. X-Ray Diffraction

23. Pictures: X-Ray Diffraction

24. Tests: Gas Chromatography First, we inject the gamma phase solution into the entrance of the column. The carrier gas carries the sample molecules through the column. The detector monitors the outlet stream from the column, and thus the time at which each component reaches the outlet and the amount of that component can be determined. First we injected only the toluene to find out that it appears at about 1.73 min. Later, we injected toluene and benzyl alcohol to see the peak height/area. We found out that it appears around 4.3 min (Graph 1). Soon, we measured the peak of the benzyl aldehyde and found out the detention time was on 3.3 min (Graph 2).

25. Tests: Gas Chromatography << Toluene + Benzyl Alcohol << Toluene + Aldehyde

26. Tests: Gas Chromatography % of Conversion = Ap/ As+Ap * 100 Peak Height After performing this on the gamma phase solution, we decided to run all the same test again but on the amorphous phase solution. We found out that the amorphous phase solution was more efficient by the conversion formula. Peak Area

27. From the results of the experiment, the hypothesis was correct. We were able to perform the catalytic oxidation of benzyl alcohol and obtain the filter solution Benzaldehyde. Some of the errors we might have made during the experiment was during the filtration process and measuring the mass. By not filtering the solution perfectly, we might have left some traces of Benzaldehyde in the filter paper. This could have cause a decrease in mass. To prevent this mistake from happening again we would use more accurate instruments to filter the solution throughout. Another mistake we might have made during the experiment was not obtaining the mass of the solution accurately. During the experiment, we might have lost some of the mass accidentally during the process of massing the solution with a balance. This cause a reduce in mass of the solution. To prevent this mistake from happening again, we would be precise in placing all the solution completely on top of the balance. Conclusion

28. By: Joseph and Bam Thank You & We Hope You Enjoy Our Presentation