Aspirin Experiment

Abstract
An experiment was carried out in which salicylic acid was esterified on its hydroxyl group using acetic anhydride. The product was acetylsalicylic acid, or aspirin, and acetic acid. The esterification was carried out under reflux using concentrated sulphuric acid as catalyst. The product was crystallized and the yield determined to be just over 36%. The melting point of the prepared product was 0 114 C 0 which differed from the published melting point of 135 C 140 0 C. Aim The focal aim of the reaction produce acetylsalicylic acetylation of salicylic experiment will allow Introduction Esters are compounds formed by combination of an alcohol with an acid, with a molecule of water being taken out. An esterification is a reaction which achieves this. An example is the production of methyl benzoate from methanol and benzoic acid. A concentrated acid catalyst speeds up the esterification reaction. The converse, splitting an ester by reaction with water to form the alcohol and the acid, is a form of hydrolysis. Esterification is a reversible process, and will reach equilibrium; the equilibrium must be shifted as far to the right as possible. With the equilibrium as far to the right as possible, the mixture of the reactants and products that are present will be at its optimum rate. This is achieved when the conditions are reflux and when using a concentrated sulphuric acid catalyst. The esterification carried out in this investigation was that of which is originally used to produce the drug aspirin. Aspirin is a member of a family of chemicals called salicylates. In the 1700s, the scientist Reverend Edmund Stone wrote about the success of the bark and the willow in the cure of the "agues," or fevers with aches. Scientists found out that the experiment was to perform a chemical to acid (Aspirin). This was performed as an acid with anhydride. The results of this us to calculate the percentage yield.

part of willow bark that was bitter and good for fever and pain is a chemical known as salicin. This chemical can be converted by the body after it is eaten into another chemical, salicylic acid. salicylic acid (made from salicin), and close relatives were used at high doses to treat pain and swelling in diseases like arthritis and to treat fever in illnesses like influenza (flu). Felix Hoffmann was another scientist who reasoned that salicylic acid may be irritating because it is an acid, he put the compound through a couple of chemical reactions that covered up one of the acidic parts with an acetyl group, converting it to acetylsalicylic acid (ASA). He found that ASA not only could reduce fever and relieve pain and swelling, but he believed it was better for the stomach and worked even better than salicylic acid. Salicylic acid Aspirin is usually prepared by reacting salicylic acid with acetic anhydride in the presence of concentrated sulfuric acid as a catalyst.This reaction is known as an Ester Formation reaction. Hypothesis to be tested (Objective) Does the Aspirin produced in the laboratory have a different melting point and yield compared to that of Aspirin manufactured on a Commercial and Industrial scale? The hypothesis is to produce aspirin in the laboratory by subsequent in a simple set of instructions the melting point and yield of the product will be obtained. This shall be judged against to the melting and yield of aspirin achieved from the industrial specification and manufacture of the product.

Experimental Plan Before beginning any of the experiments it is critical that you read the COSHHE analysis sheets for each of the chemicals that are going to be used in the experiments. This is to minimise the chance of

chemical accidents that can occur during the experiment. 1. Measure and weigh 50grams of Salicylic acid on the measuring scale. 2. Measure and collect 80ml of Acetic anhydride. 3. Mix 50g Salicylic acid with 80ml of acetic anhydride in a suitable round-bottomed Quick-fit flask. 4. In both of the mixtures of Salicylic acid and acetic anhydride add some concentrated Sulphuric acid but not more than 0.5 ml 5. After mixing the chemicals together you are now required to carry out the main stage of the experiment. Firstly make sure that the Quick-fit flask is sealed safely together, or else apply a small amount of medium oil for better sealant. 6. Heat the solution gently for 30 minutes at not more than 70 0 C. 7. During the heating process it is essential to start mixing the mixtures inside the round-bottomed Quick-fit flask, as this can be achieved when the temperature has reached 70C, turn of the heating element and let mixture cool down to 50C and pour 750ml contents of cool water. 8. After adding water to the contents of the mixed solution, you are then required to filter the product by using the filter paper and a vacuumed container for improved filtration and to dry the product. 9. Weigh the product again and record the differences. 10. Calculate the yield of the product. 11. Measure the melting point of the substance by using the pipette and the apparatus required for the melting point. 12. And record the melting point takes place. Method A sample of mass 50g of salicylic acid was weighed out on a watch glass and then transferred to a 100cm 3 three neck round bottomed flask. The flask was clamped over a heating mantle and the thermometer was fitted into one of the necks of the flaks this was done using a thermometer adaptor. The height of the bulb was adjusted so that it was near the bottom of the flask then was able to be immersed

in the reaction mixture. A condenser was fitted into one of the other necks of the flask and third outlet of the flask was stoppered. Then the of acetic anhydride was added to the salicylic acid and not more than 0.5 ml concentrated sulphuric acid were added to mixture using Pasteur pipette. The flask was heated to 70 0C for 30 minutes. It was ensured that the reagents in the flaks were allowed to cool to 50 0C and the contents of the reaction mixture were poured into 750ml cold water. The precipitate formed, which was collected by suction filtration. Product was washed on the filter paper using tow sets 10cm 3 of cold water and then product was allowed to dry on the filter paper for 10 minutes under suction. The mass of the damp product was weighed, and recrystallised using the minimum amount of hot water. The recrystallised product was collected by suction filtration. The crystals were washed in situ using tow sets of 10cm3 of cold water. The crystals were let to dry for a week and the mass was recorded. This value was used to calculate the percentage yield of the acetylation reaction. Hazard and Risk Analysis COSHHE Analysis for the chemicals With all experiments the main precautions that are taken are head, eye (Goggles) and clothes protection. Gloves were also worn to protect the hands when handling equipment. Extra precaution was taken when pouring the product into the mould due to the hazardous and corrosive properties of the reactants. Apparatus 3- Neck flask

Beaker glass

Ring stand and clamp

Round bottom quick fit glass

Thermometer

Watch glass

Micro pipette

Heater element apparatus

Plastic beakers

Data Mass of aspirin = 215.0400g Melting of aspirin 114.3 0C Melting of aspirin 116.4 0C Melting point published 135 0C -140 0C Mass of watch glass = 185.5367g Dried Aspirin = 209.176 Results When water was added to the beaker a gradual colour change was observed from colourless to brown. Following washing the yield was recorded on the balance and found to be 36.19%. The crystals appeared to be pure white in colour at this stage. Calculations

1 mole salicylic acid 138g 1 mole of Aspirin = 180g 138g of salicylic acid ,180g Aspirin there for 50g of salicylic acid will react to give theoretical yield. 50 x 180 ---------- = 65, 21 = Theoretical yield. 138

To calculate the percentage yield formula used = mass obtained divided mass expected x 100 Mass obtained / mass expected x 100 = yield %

185.5367 209.1765 = mass obtained 23.60 ------ X 100 = 36.19 65.21 Discussion and interpretation The experiment worked, in that pure white crystals were obtained and Aspirin in its pure form is a white crystalline solid. The yield obtained 23.60g. It is never possible in any experiment to get a perfect 100% yield. This is due to factors, such as the reagents used are not themselves totally pure and also that, due to kinetic theory of chemical reactions, all of the reagents will never fully react. In addition the esterification process is an equilibrium reaction, and there a 100% yield is never possible en under ideal conditions. In order to calculate the maximum possible yield, the value Kc the equilibrium constant, under these conditions would be required kc is the ratio of products to reactants at equilibrium. This reason is why; often one reagent is added in excess. This uses Le Chataliers principle, which in effect means that when one of the reactants is in excess, the equilibrium will be shifted more favourable towards the

products. Also there will be inevitable errors in mass readings from the balance, losses on transferring materials and losses on filtration and washing. These later losses are always a compromise in that the more it is washed the purer it will be, but the more that will be lost. Overall the percentage yield of 36.19 is fairly good for a first time attempt at the experiment. MLA Citation:
"Aspirin Experiment." 123HelpMe.com. 25 Des 2013 <http://www.123HelpMe.com/view.asp?id=148144>.