MOHAWK COLLEGE OF APPLIED ARTS AND TECHNOLOGY CHEMICAL AND ENVIRONMENTAL TECHNOLOGY DEPARTMENT. Lab Report ROOM NO: FE E309

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1 MOHAWK COLLEGE OF APPLIED ARTS AND TECHNOLOGY CHEMICAL AND ENVIRONMENTAL TECHNOLOGY DEPARTMENT Lab Report ROOM NO: FE E309 EXPERIMENT NO : 10 TITLE : Synthesis of Acetylsalicylic Acid Submitted by Class Partners Instructor : Lyndsay Grover : BIOL lab. : Awatif Hagelamin : Farag Soliman Date lab performed : February 17 th, 2011 Date of submission : February 24 th, 2011 FENNELL CAMPUS HAMILTON, ONTARIO 1/6

2 Purpose: The purpose of this experiment was to synthesize acetylsalicylic acid and recover the solid product by vacuum filtration. Also to test the purity of the crude product via comparison to other forms of ASA and its components and to purify the product via recrystallization. This experiment is a great introduction to students of biotechnology about the work involved in the pharmaceuticals industry. Apparatus: - 125mL Erlenmeyer flask - stirring rod - 10mL graduated cylinder - Buchner flash vacuum system - steam bath - ice bath - filter paper - test tubes - Reagents: Salicylic acid, acetic anhydride, sulfuric acid. Safety Guidelines: Use precaution when handling salicylic acid as it may be slight skin irritant. Use precaution and keep distance when using acetic anhydride as eve the fumes can be an eye irritant, also skin irritant. Procedure: Synthesis of ASA 1. Clean glass ware and dry in oven at 110 C for a few minutes. In the meantime set up and plug in steam bath, assure that there is constant water flow so as to prevent the steam bath from drying out during experiment. Also set up a vacuum trap, Buchner flask and a Buchner funnel with filter paper and adapter. 2. Weigh out 3.0 +/- 0.1g of salicylic acid in a weighing boat. Weigh the boat to the nearest 1mg, Add the solid to the dry 125mL Erlenmeyer flask. Reweigh the boat. Record all weighing in Table A. 3. Measure out 6mL of acetic anhydride into graduated cylinder and carefully add to flask. If possible pour the liquid down the walls of the flask and the solid salicylic acid down the flask. Mix reactants with stirring rod, do not remove stirring rod. 4. Using the Pasteur pipet add three drops of concentrated sulfuric acid to the mixture and stir again. Place flask on the steam bath for 15 minutes, stirring every few minutes. 5. Remove from steam bath and cool using an ice-water bath. At the same time cool 50mL of distilled water in the wash bottle for washing the product. Stir continuously until a thick, semi-solid mass is present. Add 50mL of distilled water using graduated cylinder. Stir and continue to cool. A thin paste of the product solid should be present. 6. Allow solid to settle. Decant the liquid off through the Buchner filtration apparatus. Add about 10mL of ice-cold water to the flask, stir to wash the solid, then allow to settle. Decant through filter. Add a second 10mL portion of ice water, stir and pour the solid down the stirring rod onto filter. Use several small portions of ice-water from wash bottle to complete the transfer of solid to the filter paper. 7. Draw air through the solid to help dry the crystals, after a few minutes of drying, release the vacuum trap and turn off the suction. 2/6

3 8. Pre-weigh a larger piece of filter paper. Transfer the crud ASA onto this paper and allow to dry in air for several minutes. Weight the filter paper plus product. Record weighing in Table A. 9. Calculate theoretical yield and the percentage of ASA from your measurements. Product Testing 1. Aging of ASA: Take 300mg of pure ASA and divide the sample into two parts. Put one part into a small open vial and place it in the oven at 110 C for 30 minutes. Remove sample vial and allow to cool. 2. Odour Test: Carefully test the pure ASA, the aged ASA, the salicylic acid and the crude ASA for any odour. Record observations and conclusions in Table B. 3. Phenol Test: In test tubes place a few small crystals of salicylic acid and 2-3mL of distilled water. Ass one drop of FeCl 3 solution and mix well. Repeat with pure ASA, aged ASA and crude ASA. Record observation and conclusions in Table B. Calculations: Balanced Chemical Equation of Reaction: (HO)C 6 H 4 COOH + (CH 3 CO) 2 O [H + ] (CH 3 COO)C 6 H 4 COOH + CH 3 COOH Theoretical Yield of ASA: g Salicylic Acid x 1 molsa x 1 molasa x gASA = 3.777g ASA gSA 1 mol SA 1 mol ASA Percent Yield (%w/w) of ASA: = g/3.777g x 100 = 130.4%w/w Data: Table A: Synthesis of Acetylsalicylic Acid Weighing of Salicylic Acid Boat + Solid (g) Boat Alone (g) Solid (g) Weighing of Crude ASA Paper Alone (g) Paper + Product (g) Product (g) Test Substance Pure ASA Aged ASA Salicylic Acid Crude ASA Table B: Product Testing Observations and Conclusions Odour Test Observations/Conclusions No Smell No acetic acid present Slight smell of acetic acid Acetic acid present No odour No acetic acid present Smells strongly of acetic acid Acetic acid present Phenol Test Observations/Conclusions Clear No salicylic acid present Clear No salicylic acid present Purple colour Salicylic acid present Clear No salicylic acid present 3/6

4 Observations: Description of Crude Product Solid: Appearance: chunky, white powder, clumping, forms solid mass, light, loose. Odour: Smells strongly of acetic acid. Experiment Observations: - salicylic acid: white fine powder -acetic anhydride: liquid, clear, eye irritant - solution at start: cloudy, some remaining white solid at bottom -solution after 5 minutes of being heated: clear with some remaining white solid at bottom -solution after 10 minutes of being heated: clear solution, no solid present -solution after full 15 minutes of being heated: clear liquid, no solid present - solution after being added to ice bath and stirred: became thick paste, solid formed -after allowed to settle: clear liquid on top, white solid on bottom Discussion: This experiment is a great introduction for Biotechnology students some of the work we will be doing in later semesters in relation to our pharmacology and bio-pharmaceuticals courses. It is all the first synthesis of a product that we know in our daily lives and gives us a greater understanding of how our various medications are made and the process to synthesize them is rather simple. This is also an important experiment in terms of experience of employment later on. We can show that we have synthesized a simple form of medication and also performed our own simple form of quality assurance on our results to ensure that they are accurate and safe. While working on this lab it was interesting to few the various forms our solution took until it ended in the crude ASA. As well as finally filtering out the solid mass and observing its consistency and relating it to the ASA we know and how while further purification it would indeed take on the form we know. Sources of Error: Possible Sources of Human Error: Improper measurements of salicylic acid and acetic anhydride. Failure to include sulfuric acid. Incorrect heating time and temperature. Failure to dry through vacuum filtration or air drying. Loss of product during filtration or transfer. In testing failure to add ferrous solution. Possible Sources of Equipment Error: Balance reading incorrect. Steam bath unstable temperature. Vacuum filtration not working to maximum capacity. Possible Sources of Experiment Error: Improper concentrations of salicylic acid, acetic anhydride, sulfuric acid, and ferrous solution. Contaminated samples of Pure ASA and Aged ASA. Post Laboratory Questions: 1. One place where loss of product can occur is during filtration, product can remain in the flask and be unable to be washed out or can slip underneath the filter paper and be filtered into the flask. During weighing, it is possible to lose some product in all the movement of weighing and also some product will remain on the filter paper. 4/6

5 2. This falsely increase the percentage yield calculated of the product. Since water is contained in the product still as it is weighed it will increase the weight. So there isn t as much product as the weighing reads and thus will falsely increase the percentage yield calculated. 3. Filtering all the air out for longer through the vacuum filtration system then drying it on the oven at 110 C for a measure of time to dry out any of the water that still may be present. 4. Yes my crude ASA is free salicylic acid, this is proven by the phenol test in which a positive result for salicylic acid was not achieved. 5. Commercial ASA has an expiry date because after a while it breaks downs into acetic acid and salicylic acid. Salicylic acid is lethal in rats in doses of mg/kg, considering the average tablet of ASA is 500mg it is safe to assume that the salicylic acid present in the tablet could cause some considerable harm. Conclusion: After reviewing the observations from the phenol test in addition to observing the final product of our crude ASA I am certain we successfully synthesized ASA. Although it did smell strongly of acetic acid it did not contain any salicylic acid which was the determining factor for the ASA. The smell of the acetic acid could have been a byproduct of the reactions and would have disappeared once the ASA was purified. When looking at the percent yield calculated it is clear that we synthesized more ASA than should have. This leads me to believe that measurements may have been wrong in the weight of the salicylic acid or in the weighing of the final product. The weighing of the final product is more the case considering we had some difficulty in getting a consistent number from the balance while weighing the final product. Despite the errors in measurement I am still confident in our results since they are proven through the phenol test. 5/6

6 References: Biotechnology, An Introduction S.R. Barnum, 2 nd Edition, Biotechnology 1, Laboratory Manual. Mohawk College, Custom Courseware, /6

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