Lab Report 4

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Chemistry

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Jan 9, 2024

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Experiment #4 Separation of the Components of an Analgesic Tablet Date Preformed—March 1, 2023 Date Due—March 15, 2023 Experimental Objective Separate components of an Excedrin tablet using acid-base extraction. By separating the components of the tablet, we use recrystallization, extraction, and the TLC skills learnt in previous labs.
Reagents Used Aspirin Acetaminophen Caffeine MW 180.16 g/mol MW 151.16 g/mol MW 194.19 g/mol Procedure Separation of Components and Work-Up A Hirsch funnel and filter flask (25 mL) was set up for vacuum filtration. The chemical mixture was weighed out and added to a beaker (20 mL) then dichloromethane (8 mL) was added to the beaker and stirred. The mixture was then filtered through the Hirsch funnel and washed with additional dichloromethane. The solid on the filter paper was put into a test tube and the liquid was placed into a centrifuge tube. Acetaminophen Recrystallization Water (3 mL) was added to the test tube that contained the solid filtered out of the original mixture. The test tube was heated in a hot bath till the solid dissolved into the water, more water was added to our test tube so all solid could be dissolved. Once dissolved the solution was cooled to room temperature and then placed in an ice bath. Once cooled crystals were formed, the crystals were filtered out of the solution using vacuum filtration. Once the crystals had dried, they were weighed and set aside in a plastic plate. Caffeine Isolation 3M sodium hydroxide (4 mL) was added to the liquid in the centrifuge tube and the layers were mixed by pushing the liquid in and out of a Pasteur pipette. Once two layers reformed the first layer, the aqueous layer, was removed using a Pasteur pipette and placed into a clean test tube. Water (0.5 mL) was added to the centrifuge tube and mixed again. The top layer was collected a second time and placed into the same test tube, and the test tube was then set aside. The dichloromethane solution in the centrifuge tube was moved into a clean beaker (20 mL) and calcium chloride pellets were added to dry the solution. Once dry the dichloromethane was put into a test tube and set aside. Aspirin Precipitation The aqueous layers from the dichloromethane solution where the sodium salts of aspirin were. Concentrated hydrochloric acid was added using a dropper, after a few drops were added the solution was stirred with a boiling stick. Once the solution was cloudy and a solid had formed the leftover liquid was extracted via Pasteur pipette. Water (3 mL) was added, and the solution was heated to dissolve the solid. More water was added to fully dissolve the solid, once fully dissolved the aspirin was collected by vacuum filtration. The aspirin was weighed and set aside in a plastic plate. Thin Layer Chromatography A TLC plate was prepped, and 95% ethyl acetate 5% acetic acid was added to the bottom of a TLC jar. The caffeine was already dissolved in dichloromethane and was ready for TLC. Aspirin and acetaminophen (30 mg each) were both added to separate test tubes with ethanol (1 mL). With separate micropipettes for each test tube each mixture was spotted on the TLC plate and then set in the TLC jar to develop. Once developed a UV light was shone on the plate and it was marked where each mixture had traveled to. The R f values were calculated and compared to the R f values from lab 2.
Results I. Excedrin mass 0.566 g II. Final masses of aspirin and acetaminophen Aspirin: 0.061 g Acetaminophen: 0.188 g III. Theoretical yield for three constituents of Excedrin (values and calculations) Aspirin: 0.566 gof mixture 44.25% As 100 = 0.250 g Acetaminophen: 0.566 gof mixture 44.25% Ac 100 = 0.250 g Caffeine: 0.566 gof mixture 11.5 % Ca 100 = 0.066 g IV. Precent yield of aspirin and acetaminophen (values and calculations) Aspirin: 0.061 g 0.250 g 100% = 24.4% Acetaminophen: 0.188 g 0.250 g 100% = 75.2% V. TLC plate sketches From Lab 4 From Lab 2 VI. At least one example calculation for R f values. Include all R f values. Example: 1.6 cm 6.2 cm = 0.26 R f Values: R f Reference: 95:5 ethyl acetate: acetic acid 95:5 ethyl acetate: acetic acid Solvent Distance (cm): 6.2 cm Caffeine R f : 0.21 Caffeine Spot (cm): 1.6 cm Acetaminophen R f : 0.43 Caffeine R f : 0.26 Aspirin Spot #1 R f : 0.71 Acetaminophen Spot (cm): 3.1 cm Aspirin Spot #2 R f : 0.71 Acetaminophen R f : 0.5 Aspirin Spot #1 (cm): 4.6 cm Aspirin Spot #2 (cm): 4.6 cm Aspirin Spot #1 R f : 0.74
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Aspirin Spot #2 R f : 0.74 VII. Physical description of products Final aspirin: fine white powder Final acetaminophen: cream colored powder, thin prismatic texture Final caffeine: clear liquid VIII. Answers to questions in data sheet 1. What do the results of our TLC analysis indicate? a. The values are closely related which tells us we correctly extracted the components of the excedrin tablet. Conclusion The separation of the excedrin tablet components was successful, however there was a spill when the mixture and dichloromethane was added to the Hirsch funnel for filtration. Aspirin, acetaminophen, and caffeine were separated using vacuum-filtration and acid-base extraction. The final aspirin and acetaminophen products were both light powders, while the caffeine remained liquid. The aspirin and acetaminophen were obtained in a 24.4% and 75.2% yield. By using thin layer chromatography on the final three products, the TLC plate and R f values were compared to the TLC plate and R f values from lab two. The comparison showed the plates and values were closely related, confirming the components were successfully separated from the tablet. However, the spill in the beginning of the experiment could have caused the percent yield of the experiment to be lower than expected. References National Center for Biotechnology Information. PubChem Compound Summary for CID 2244, Aspirin. https://pubchem.ncbi.nlm.nih.gov/compound/Aspirin . Accessed Feb. 13, 2023. National Center for Biotechnology Information. PubChem Compound Summary for CID 1983, Acetaminophen. https://pubchem.ncbi.nlm.nih.gov/compound/Acetaminophen . Accessed Feb. 13, 2023. National Center for Biotechnology Information. PubChem Compound Summary for CID 2519, Caffeine. https://pubchem.ncbi.nlm.nih.gov/compound/Caffeine . Accessed Feb. 13, 2023.