1. Optimization of Furfural Acetone July 25, 2011 Shang Kuan Tsai Chi PattharawadeeThanthranon

2. Some Clarifications What does the word ‘Optimization’ mean? According to Merriam Webster, optimization is a process of making something as effective as possible

3. Introduction With the number of people in the world increasing, the demands for oil also rise; this means that oil becomes a lot rarer and a lot more expensive. The experiment that is going to be done during the course of the internship is a reaction that changes sugar (furfural) into furfural acetone, a product that can then be further react to make fuel for cars.

4. Purpose Base Furfural + Acetone -----> Furfural Acetone The purpose of the experiment is to find the base that is the most efficient in changing sugar to furfural acetone (C8).

5. Hypothesis The hypothesis is that NaOH, a strong base, will produce the most furfural acetone when it is allowed to react with the reactants for a long time, because the stronger a base is, the better results it will produce.

6. Material List Lab coat 2-Furaldehyde (0.4145 mL/base) Acetone (0.3676 mL/base) Bases NaOH (0.02 g) KOH (0.028 g) Ca(OH)2 (0.037 g) Mg(OH)2 (0.029 g) Sr(OH)2 Ba(OH)2 (0.086 g) Hot plate and stirrer (2) Clamp (4) Stand (2) Bowl (2) Tap water Round-bottom flask 25 mL (2) Gas inlet (2) Cooling Ace (1) Condenser (2) Goggles

7. Material List Magnetic bar (2) Label stickers (6) Micro-pipette (1) Electronic balance (1) Weighing paper (6) Pestle (1) Spatula (2) Joint clip (2) Rubber Tube (1) Tips (12) Gas-Chromatography-Mass Spectrometer (GCMS) Dropper (4) Syringe (4) Vial (4) Sodium Sulfate Towels (2) BIBASE Rubber support rings (2) Syringe filers (4) (yellow and pink)

8. We will be doing 6 reactions (using 6 different bases) in this experiment, but because it will take some time to wait for all of the bases to react one at a time, we will be doing 2 at once. The following is the procedure…

9. Procedure Wrap up the 2 condensers with the towels Set up 2 sets of clamp and stand with 2 clamps per stand. Make sure the clamp is tightly clamped Place a hot plate and stirrer beneath the clamps. Add half bowl of tap water into the bowl. Put the bowl on the hot plate. This is to prevent a big change in temperature throughout the day, because water has a high specific heat.

10. Procedure Hold the wrapped up condenser tightly on the clamp. Make sure the 2 condensers are hold at the same height and position. Put a gas inlet on the top hole of the condensers. Hold the 2 tubes from the cooling ace. Plug the tube that pushes water in on the most bottom hole of one of the condenser, and the second tube from the cooling ace on the 2nd most top hole of the second condenser. This should be done tightly. Gas Inlet

11. Procedure Connect the remaining 2 holes on the condenser with a rubber tube. Set the cooling ace to about 15 degree Celsius Start pumping water from the cooling ace Put a magnetic bar into both round-bottom flasks. Put a label on the neck of both round-bottom flasks. Choose 2 bases to work with first (here we will be doing NaOH and KOH first). Cooling Ace

12. Procedure **The next 3 steps should only be done for bases that cone in small grains, not the ones that are powder (Step 17-19) Put the 2 bases on weighing paper; one base per paper. Fold the paper in half so that the bases are enclose inside Use a pestle to crush the bases into smaller pieces Measure the amount needed for the 2 bases (as written in the equipment list) using an electronic balance. Pestle

13. Procedure Put the bases into the 2 round-bottom flasks; one bases per flask. Measure 0.4145 mL (to the nearest thousandth) of 2- furaldehyde using a micropipette. Pour the furfural into one the round-bottom flasks Change the tip of the micropipette to prevent any contamination of the next chemical. Measure 0.3676 mL (to the nearest thousandth) of acetone using the micropipette. Pour the acetone into the same round-bottom flask

14. Procedure Repeat step 22-26 again but this time put the 2-furaldehyde and acetone into the other round-bottom flask. Take both round-bottom flasks underneath the condensers held on the clamps. Use a joint clip to hold both flasks to their condenser; one clip per flask. Turn on the stirrer to 300 rpm. Wait for the reaction to happen for the next 3 hours. Stop the cooling ace Hot plate and Stirer Magnetic Bar Spinning in a Flask

15. Procedure Stop the stirrer Remove the joint clips and the round-bottom flasks Using a dropper, suck out the entire crude product that is in the flasks into syringes with yellow filters. Carefully, squeeze the crude product in the yellow syringes into 2 vials. Syringe Filter

16. Procedure Sodium Sulfate 36. Add Sodium Sulfate into the 2 vials to remove any water in there. Make sure to add until the sodium sulfate will slightly move when we shake the vials. 37. Using new droppers, suck out the liquid portion from the vials, and squeeze them into new syringes with pink filters. 38. Carefully, squeeze the liquid into new vials. 39. Close the cap of the vials. 40. Repeat all steps again for 2 more times, but change the bases to the next 2 Mi shaking the solution

17. After finishing all the steps, we also did a shorter version of the experiment just to test and compare the results that we got. This time we did the experiment exactly the same way, but instead of waiting for 3 hours, we waited only 1. ** After each experiments, don’t forget to wash everything with acetone!

18. Data & Results Data 1: 3 hours

20. Gas-Chromatography-Mass Spectrometer (GCMS) Results: NaOH The peaks at about 8.8 to 9.5 (time) indicate amount of Furfural Acetone produced The peaks at about 18.3 (time) indicate amount of C13 produced

21. Gas-Chromatography-Mass Spectrometer (GCMS) Results: KOH The peaks at about 3.5 to 5.5 (time) are the amount of initial reactants left unreacted.

22. Gas-Chromatography-Mass Spectrometer (GCMS) Results: Ca(OH)2

23. Gas-Chromatography-Mass Spectrometer (GCMS) Results: Mg(OH)2

24. Gas-Chromatography-Mass Spectrometer (GCMS) Results: Sr(OH)2

25. Gas-Chromatography-Mass Spectrometer (GCMS) Results: Ba(OH)2

26. Data 2: 1 hour

28. Gas-Chromatography-Mass Spectrometer (GCMS) Results: NaOH

29. Gas-Chromatography-Mass Spectrometer (GCMS) Results: KOH

30. Gas-Chromatography-Mass Spectrometer (GCMS) Results: Ca(OH)2

31. Gas-Chromatography-Mass Spectrometer (GCMS) Results: Mg(OH)2

32. Gas-Chromatography-Mass Spectrometer (GCMS) Results: Sr(OH)2

33. Gas-Chromatography-Mass Spectrometer (GCMS) Results: Ba(OH)2

34. Analysis -3

35. Conclusion The results (graph) show that my hypothesis was correct because stronger bases did indeed produce better results! Secondly, the set of reaction that was done 3 hours also proved that the hypothesis was correct because it got better results than the set that was done in 1 hour. The reasons are because stronger bases make the reaction possible and by waiting for a longer time, we are allowing more furfural and acetone to react, thus producing more furfural acetone. That’s why the reaction was incomplete when we used weaker bases (alkaline earth hydroxides). However, there was a partial mistake in my hypothesis. This is because when bases get too strong, they might cause further reactions among furfural acetone and the reactants, forming C13. This is why NaOH also produced a large amount of C13 in addition to C8. If we were to do another set of experiment but for 24 hours, there might be some C21 because the products may start to react with each other more often. So in conclusion, KOH should the best base for my experiment, because its basic strength is just right. But as the graph implies, KOH didn’t produce the best results, which means that we must have done something wrong during the process, making the reactants unable to react with each other properly.

36. Conclusion: Error Analysis There may have been some errors, both human and measurement errors, throughout the experiment, causing slight mistakes in our data and result. Some of the errors might have been inaccurately measured the mass of the base used, not reacting all the bases that were added to the flask, not setting the micropipette to the appropriate value, and not enough sodium sulfate was added. Next time, we would be more careful as so to be more accurate in our results.

37. THE END 

38. Big Thanks To…  Dr.EkasithSomsook P’AmonwanSayasiri(P’Baitong)  And everyone else in Mahidol