Aspirin Lab By Maya Parks Partner: Ben Seufert 6/5/15, 6/8/15

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1 Aspirin Lab By Maya Parks Partner: Ben Seufert 6/5/15, 6/8/15 Abstract: This lab was performed to synthesize acetyl salicylic acid or aspirin from a carboxylic acid and an alcohol. We had learned in class about esterification in class and this lab demonstrated that process. Although we only had a 54% yield, our aspirin was 98% pure. This could be do to perhaps boiling off some the ester, or not precipitating out the crystals. This lab was very successful in demonstrating how esters are created and giving an application of organic chemistry. Aspirin is very common drug, and being able to synthesize it is very important. In addition to being a useful application of organic chemistry, this lab helped us develop better lab techniques. Purpose: We will be synthesizing acetyl salicylic acid or aspirin in this lab. This will serve to demonstrate how a carboxylic acid and an alcohol combine to form an ester. The process of esterification is quite intricate; we heated the solution so as to push it to create more products, but not too much so as not to boil off the ester, and we then promptly cooled it in an ice bath to precipitate out the crystals. We were able to practice good lab techniques as well as demonstrate organic chemistry which we had previously learned in class. Materials: 50 ml Erlenmeyer flask Solid salicylic acid Two 10 ml graduated cylinders Concentrated sulfuric acid solution, H 2 SO 4 25 ml graduated cylinder liquid acetic anhydride funnel, and filter paper distilled water spoon, spatula, or rubber policeman cold distilled water Ice bath small rubber band

2 Hot plate plastic Beral pipet or eyedropper fume hood Balance Part II Colorimeter Test Materials Vernier computer interface Computer Vernier Colorimeter solid salicylic acid aspirin crystals 95% ethanol plastic cuvette with lid M iron (III) nitrate solution, Fe(NO 3 ) ml beaker distilled water 100 ml beaker 100 ml volumetric flask 50 ml graduated cylinder 250 ml volumetric flask PROCEDURE Part I: Synthesize Aspirin 1. Obtain and wear goggles. 2. Measure out 2.0 grams of salicylic acid into a 50 ml Erlenmeyer flask. 3. This Step should be done in the Chemical Fume Hood. Add 5.0 ml of acetic anhydride and 5 drops of concentrated sulfuric acid solution. Swirl the mixture. If necessary, use a sparingly small amount of distilled water to rinse down any bits of solid that may be on the inner walls of the flask. CAUTION: Handle the sulfuric acid and acetic anhydride with care. Both substances can cause painful burns if they come in contact with the skin. 4. Heat the mixture on a hot plate, at 75 C-85 C, for 15 minutes, or when the mixture ceases releasing vapors. Stir the mixture occasionally during heating. After about 10 minutes, add 2 ml of distilled water to the flask. 5. When you are confident that the reaction has reached completion (no vapors appearing), carefully remove the flask from the hot plate and add 20 ml of distilled water. Allow the mixture to cool to near room temperature. Transfer the flask to an ice bath for about five minutes. As the mixture cools, crystals of aspirin should form in the flask. 6. Set up a funnel and filter flask so that you are ready to filter the reaction mixture after it has cooled.

3 7. Transfer the contents of the cooled flask to a Funnel assembly. When most of the liquid has been drawn through the funnel wash the crystals with 5 ml of cold, distilled water. Wash the crystals with cold, distilled water twice more in this manner. 8. Store the aspirin crystals in a safe place and prepare to test their purity. Part II Test the Colorimetric Absorbance of an Aspirin Sample Your synthesis converted most, but not all, of the salicylic acid into acetylsalicylic acid. You will mix iron (III) nitrate with salicylic acid and your aspirin sample to complex the salicylic acid, which is a bluish-purple color. You will analyze several samples to determine the amount of salicylic acid in your synthesized aspirin. You can use this information to calculate the purity of your aspirin sample. Follow Steps to prepare a set of salicylic acid standard solutions and conduct testing to develop your own Beer s law plot of the standards. If your instructor supplies you with the Beer s law standard data, start at Step Quantitatively prepare the stock salicylic acid solution. a. Measure out about 0.20 g of salicylic acid. Record the precise mass that you use. b. Transfer the salicylic acid to a 250 ml beaker and add 10 ml of 95% ethanol. Swirl the beaker to dissolve the solid. c. Add 150 ml of distilled water to the beaker. Mix the solution. d. Quantitatively transfer the solution from the beaker to a 250 ml volumetric flask. Thoroughly rinse the beaker with several portions of distilled water, and transfer the rinse water to the volumetric flask. Add distilled water, as needed, to fill the flask to the 250 ml mark. Mix the solution thoroughly. Calculate the precise molar concentration of your stock solution and record it in your data table. 2. Prepare four standard solutions of varying concentrations of salicylic acid. a. To prepare 100 ml of you first standard solution, quantitatively transfer precisely 10 ml of the stock salicylic acid solution to a 100 ml volumetric flask. b. Add M Fe(NO 3 ) 3 solution to the flask to make precisely 100 ml. c. Calculate the precise molar concentration of your first stock solution and record it in your data table.

4 d. Prepare the remaining three salicylic acid standard solutions by diluting the stock solution that you prepared in Part a of this step. Decide on a suitable set of dilutions for your Beer s law plot. e. Calculate the precise molar concentration of each dilution and record it in your data table. 3. Connect a Colorimeter to Channel 1 of the Vernier computer interface. Connect the interface to your computer using the proper cable. 4. Open the file Exp 22 Aspirin Color from the Advanced Chemistry with Vernier folder. 5. Calibrate the Colorimeter. a. Prepare a blank by filling an empty cuvette ¾ full with distilled water. Place the blank in the cuvette slot of the Colorimeter and close the lid. b. If your Colorimeter has a CAL button, set the wavelength on the Colorimeter to 565 nm, press the CAL button, and proceed directly to Step 20. If your Colorimeter does not have a CAL button, continue with this step to calibrate your Colorimeter. c. Choose Calibrate CH1: Colorimeter from the Experiment menu, then click. d. Turn the wavelength knob on the Colorimeter to the 0% T position. e. Type 0 in the edit box. f. When the displayed voltage reading for Input 1 stabilizes, click. g. Turn the knob of the Colorimeter to the Green LED position (565 nm). h. Type 100 in the edit box. i. When the voltage reading for Input 2 stabilizes, click, and then click. 6. You are now ready to collect absorbance-concentration data for the four standard solutions. a. Click. b. Remove the cuvette from your Colorimeter and pour out the water. Using the solution in the first 100 ml volumetric flask of salicylic acid, rinse the cuvette twice with ~1 ml amounts and then fill it ¾ full. Wipe the outside with a tissue, place it in the Colorimeter, and close the lid. c. After closing the lid, wait for the absorbance value displayed on the monitor to stabilize, then click, type the molar concentration in the edit box, and press the ENTER key. The data pair should now be plotted on the graph.

5 d. Discard the cuvette contents as directed by your instructor. Using the solution in the second 100 ml volumetric flask, rinse the cuvette twice with ~1 ml amounts, and then fill it ¾ full. Wipe the outside, place it in the Colorimeter, and close the lid. When the absorbance value stabilizes, click, type the molar concentration in the edit box, and press the ENTER key. e. Repeat the procedure for the remaining salicylic acid solutions that you prepared. f. When you have finished with the last salicylic acid solution, click. Record the absorbance and concentration data pairs for the standard solutions in your data table. g. Examine the graph of absorbance vs. concentration. To calculate the best-fit line equation, click the Linear Regression button,. Record this equation in your data table. 7. Prepare the aspirin sample for testing. Complete this step quickly. a. Measure out about 0.20 gram of aspirin and transfer it to the 250 ml beaker. Record the precise mass of aspirin that you use. b. Add 10 ml of 95% ethanol to the beaker of aspirin sample. Swirl the mixture to dissolve the solid. c. Add 150 ml of distilled water to the beaker. Mix the solution. d. Quantitatively transfer the solution from the beaker to a 250 ml volumetric flask. Thoroughly rinse the beaker with several portions of distilled water, and transfer the rinse water to the volumetric flask. Add distilled water, as needed, to fill the flask to the 250 ml mark. Mix the solution thoroughly. e. Transfer 5 ml of the aspirin solution from the 250 ml volumetric flask to a clean and dry 100 ml volumetric flask. Add M Fe(NO 3 ) 3 solution to the flask to make precisely 100 ml. Mix the solution thoroughly. 8. Measure and record the absorbance of the treated aspirin sample. This must be done within 5 minutes of completing Step 21. a. Transfer about 1 ml of the treated aspirin sample to a clean and dry plastic cuvette. b. Rinse and fill the cuvette ¾ full with the sample. Cap the cuvette and place it in the Colorimeter. c. If the absorbance value falls within the range of the salicylic acid standard solutions, record it in your data table. If it does not, repeat Step 21d with a more dilute, or more concentrated sample.

6 d. Repeat Parts a-c of this step twice with new aliquots of the treated aspirin sample. 9. Discard all solutions as directed. Data: Grams of salicylic acid 1.94g Volume of acetic anhydride 10.0mL Weight of filter papers (2) both 2.31g, 2.31g Mass of aspirin (2) 3.56g, 2.46g Mass of salicylic acid used for conc. 1 and 2.218g Absorbance Absorbance Mass of salicylic acid used for conc. 3 and 4.205g Absorbance 3.425g Absorbance Absorbance with no salicylic acid.006 Calculations: 1. Take grams of sal. Acid divide by molar mass and multiply by molar ratio (1:1) and multiply by the molar mass of acetyl salicylic acid a. 2. Based on the results of the absorbance testing with the Colorimeter, what is the percent purity of your sample of aspirin? a. Find line using points and then solve for molarity using absorbance of sample of aspirin, and calculate masses of each and subtract calculated molarity from theoretical molarity and divide by theoretical molarity

7 Absorbency b. M 2 = x 10-4 M c. M 3 = x 10-4 M d. M 4 = x 10-5 M e. M 5 = 0.00 Purity y = x Molarity.023=2003.3x =2003.3x x= 8.49 x 10-6 M 3. Use your percent purity calculations to determine the percent yield of your synthesis of aspirin.

8 = = = 1.4g.98 x 1.4g= 1.372g Error Analysis: 1. We didn t have time to let all the crystals form and so much of the solution was dumped down the drain. If we had let it freeze for a bit longer, it might have created more aspirin crystals. Also, when heating the solution, it was always closer to 85 C and once went over. This would cause the ester to be boiled off, and the percent yield decreased. 2. Online, in the synthesis portion, there were additional steps to purify the aspirin. One such step was recrystallization. This is where you dissolve the aspirin in warm ethanol and it pulls out the extra salicylic acid, then place it in an ice bath and the aspirin crystallizes, while the salicylic acid and ethanol do not. Additionally, it would be helpful to have a rough surface for the crystals to form on as the smooth glass is very difficult for the crystals to form on. 3. I would have the points for the line found either as a class average or by each group individually, as the other group had weird points as the factors were supposed to be directly proportional, and their points showed an inverse proportion. If a class average, the points would be more accurate, and if individual, then the points would be more consistent. Secondly, this lab only tests for salicylic acid in the solution. There are a number of other compounds that could be causing the aspirin to be impure. Only testing for one impurity would be an inaccurate calculation of purity. Another method for testing aspirin purity would be titrating it with a strong base as it is an organic acid. Both methods could be employed in the testing.

9 Conclusions: 1. (Acetic Anhydride has a density of 1.08g/mL) 1.94g of salicylic acid creates 2.53g of aspirin Salicylic acid is the limiting reactant. The amount of acetic anhydride we used could have created about 19g of aspirin, whereas the salicylic acid only creates 2.53 grams of aspirin. 2. You want to freeze the aspirin crystals and take them out, by having them precipitate out of the solution due to the temperature. 3. Very impure, as the solution turns purple in the presence of salicylic acid. This means there must be a large amount of salicylic acid in the mixture, and this means the aspirin is very impure.

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