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elvis ansu

UBN: 12010190 |


Table of Contents

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Aspirin was first discovered 110 years ago, but the natural form, salicylic acid, found in plants) has been used for thousands of years. As early as 3000 BC, the ancient Egyptians used willow bark and myrtle to reduce pain and fever. (Monash University, 2010). In 1853, scientist Charles Fredric Gerhardt was the first to prepare of aspirin by the addition of an acetyl chemical to natural salicylic acid, however this form was said to be unstable. In 1897, Felix Hoffmann made aspirin in a chemically pure form, stable and more palatable independently. Hoffman's used aspirin on his father for rheumatic pains (Monash University, 2010). Two years later, on March 6, 1899, aspirin was made commercial use. In this days aspirin is use in over 80 countries and it was one of the very first drugs to be made available in tablet-form. Aspirin has been regarded as the most successful non-prescription medicine of all time and it is now a standard worldwide remedy for pain, inflammation and fever. (Monash University, 2010)

Weigh 2.50g of salicylic acid (C7H6O3) into 100 cm3 conical flask. Obtain a thermometer suitable for stirring and take it with the flask and contents to a fume cupboard. Cautiously add 3.5cm3 of acetic Anhydride (C4H6O3) to the salicylic acid swirling gently to mix the reagents. Use a Pasteur pipette to add 5 drops of concentrated sulphuric acid to the mixture rotating the flask slowly to ensure through mixing. Stir the mixture with the thermometer and heat the flask in the water bath until the temperature reaches 50-60C.Mantain the
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temperature between these limits for 10-15, stirring with the thermometer. [Remove the flask from the water bath if the temperature exceeds 60 C and swirl the contents to bring the temperature back to require range]. During this period, a white precipitate should begin to form and stirring may become increasingly difficult as the solid separates. Allow the mixture to cool the room temperature, stirring occasionally, and then add deionised water (40cm 3). The reminder of the experiment may be done on the open bench (i.e., outside the fume cupboard). Collect the crude solid product by filtration in a Bucher funnel. Recrystallise by first dissolving the product in hot ethanol (8cm3) and then pour this solution into 20 cm3 warm (about 50C) deionized water into a 50 or 100 cm 3 conical flask. If a solid separates at this point, heat the mixture in the water bath or on a hotplate until it dissolves. Allow the clear solution to cool slowly, whereupon crystals should appear. If no crystals appear, add a seed crystals of acetylsalicylic acid to initiate crystallization. Collect the recrystallized product by filtration at the pump; dry the crystals between filter papers, measure the melting point, determine the yield of product and calculate the percentage yield.

Actual crude yield: 4.74 gms. Recovery pure yield: 1.85 gms.

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Calculate the percentage yield Weight of Salicylic acid: 2.50 gms. RMM of Salicylic acid: 138 g/mol Number of moles of Salicylic acid = 2.50/138 = 0.018mol Volume of acetic Anhydride: 3.50 cm3 Density of acetic Anhydride: 1.08g/mol Weight of acetic Anhydride = 3.50*1.08 = 3.78 gms. RMM of acetic Anhydride: 102g/mol Number of moles of acetic Anhydride = 3.78/102 = 0.037mol RMM of Aspirin: 180g/mol Theoretical yield = 0.018*180 =3.24 gms Recovery pure yield: 1.85 gms. Percentage yield = (1.85/3.24)*100 = 57.10% During this experiment the product of Actual crude yield was 4.74gms and the recovery yield product was 1.85 gms. The percentage yield obtain was 57.10%. The melting point of Aspirin was between 126-128C. The actual melting point of Aspirin is 136C.

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Acetic Anhydride is very corrosive, flammable, and toxic and react violently with water. Acetic Anhydride was added drop-wise inside a fumed chamber.

Gloves, safety goggles and lab coat were worn during the lab session.

Sulphuric acid s toxic, dangerous for the environment and very corrosive for the skin. Sulphuric acid was added drop-wise. Gloves, safety goggles and lab coat were worn during the lab session.

Salicylic acid is toxic and very corrosive for the skin. Gloves, safety goggles and lab coat were worn during the lab session.

Ethanol is flammable, toxic, and dangerous for the environment and may be fatal if swallowed. During the lab session the ethanol was gently warmed in a water bath.

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Reaction Mechanisms.

Figure.1 reaction mechanisms of Acetylsalicylic Acid

C7H6O3(s) + C4H6O3 (aq) C9H8O4(s) + C2H4O2 (aq)

Monash University, D. o. E. a. P. M., 2010. history of aspirin. [Online] Available at: http://www.aspree.org/AUS/aspree-content/aspirin/history-aspirin.aspx [Accessed 29 April 2013].

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