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Preparation of Aspirin By Name Presented to Instructors Name Course Institution January 9, 2014

Preparation of Aspirin Introduction The process in which a desired organic substance or compound is prepared from commercially available materials is referred to as organic synthesis (Rick, 2013). This process is used in development of biofuels, drugs, and wood chemicals among others (Organic Synthesis, 2012). This process organic synthesis is aimed at designing very simple routes in creation of a molecule. Aspirin which has a chemical name of acetylsalicylic acid is a drug which is widely used as an antipyretic agent i.e. to reduce fever. It is prepared from commercially available raw materials. The drug is also used as a pain killer. Acetylsalicylic acid derived from a compound known as salicylic acid. It has a crystalline white weakly acidic substance which has a melting point of 135 degrees Celsius. Aspirin is an ester chemically. Esters are defined as substances resulting from the reaction of alcohols with acids (Otera, 2006) as in the equations below. R C OH
ACID

R OH

R C O R
ESTER

H2O

ALCOHOL

WATER

Aspirin is made as;

The structure of the reagents and products are as below Reagents Salicylic acid Structure

Acetic anhydride Structure

Products Aspirin structure

Acetic acid Structure

In this process, the reaction between salicylic acid and acetyl anhydride results in a reaction that turns hydroxyl group in salicylic acid to an acetyl group (California State University Stanislaus, 2010). A catalyst has to be used to be used for this reaction to occur, in this case phosphoric acid. Percentage yield of aspirin is calculated as;

This experiment is aimed at introducing the concepts of organic synthesis, synthesizing aspirin from salicylic acid by substitution, and to differentiate salicylic acid from acetylsalicylic acid using simple tests (Oklahoma State University, 2011). Methodology 3.0g of salicylic acid were measure and poured in a 250 ml Erlenmeyer flask. 6.0 grams of acetic anhydride was then measured and added to the Erlenmeyer flask which was then placed in the hood. While wearing safety goggles, ten drops of 85% phosphoric acid were then carefully added and the flask swirl to thoroughly mix the solution. The mixture was then heated in the hood in a beaker of warm water for ten minutes. After heating, 20 drops of distilled water were then cautiously added to the mixture. 20 ml were then added and the mixture cooled in an ice bath. The solution of aspirin was the filtered by a pre weighed paper using Buchner funnel and the aspirator. The crystals were then washed 3 ml of distilled water. A watch glass was then pre-weighed and a filter paper and the product placed in it. The weight of the aspirin was then obtained. This product contained impurities of water and salicylic acid, therefore recrystallization process was necessary. A small amount of the impure aspirin was placed in a labeled beaker and covered in a tissue. The remainder of the impure aspirin was transferred to 100 ml beaker. 10 ml of 95 % was added to the beaker and a water bath used to warm the mixture until the crystals dissolved. When the crystals were fully dissolved, 20 ml of warm water was added and the

beaker covered with a watch glass to let it cool slowly. This resulted in formation of crystals of aspirin. The recrystallization was then completed by cooling the product in an ice bath. The purified aspirin was then collected by filtration. The crystals were then dried by pulling air through them for fifteen minutes. The melting points of the products were then measured and recorded. Results and Discussion When ice cold water as added the solution, the solution became cloudy with precipitates that were white in color. This addition of water aided in the purification and isolation of aspirin crystals due to the fact that aspirin is insoluble in cold water. This purification is essential since any salicylic acid and anhydride that had not reacted is completely removed from the product. After weighing the weight of the crude aspirin, its mass was 4.02 grams. Comparing this value with the theoretical value, its evident that there is a small difference that exists between the product and the theoretical value since the product still contains some impurities. To calculate the percentage recovery yield, this value is used. In the recrystallization process, addition of 95 % ethanol was used to dissolve aspirin along with other impurities which included salicylic acid. Cold water was used to recrystallize aspirin only and the impurities left behind. The weight of the sample that was recovered was 2.18 grams. Therefore, the percentage yield was 105.32%. This implies that there was a slight error the process of preparation of the aspirin. This could be due to weighing errors e.g. weighing the sample when it was still wet. The melting point range of the pure aspirin was 130 131 degrees

Celsius. When this value is compared to the theoretical value which is 1350C, it is clear that there is a difference between the two. Conclusion The preparation of aspirin was by mixing acetic anhydride and salicylic acid. To facilitate the reaction to take place a catalyst was used and in this scenario, phosphoric acid was used as a catalyst. When water was added, there was formation of acetic acid and this made it easy to eliminate it. Impurities such salicylic acid was eliminated by recrystallization. Comparing the melting point of the purified aspirin and the crude aspirin showed that the two were close to each other.

Works Cited California State University Stanislaus, 2010. The Synthesis of Aspirin. [Online] Available at: http://wwwchem.csustan.edu/consumer/aspirincons/aspirincons.htm [Accessed 29 March 2013]. Oklahoma State University, 2011. Synthesis of Aspirin. [Online] Available at: http://intro.chem.okstate.edu/chemsource/medicine/lab1.htm [Accessed 29 March 2013]. Organic Synthesis, 2012. Oganic Synthesis. [Online] Available at: http://www.organicsynthesis.co.za/ [Accessed 29 March 2013]. Otera, J., 2006. Esterification: Methods, Reactions, and Applications. New York: John Wiley & Sons. Rick, D., 2013. Organic Synthesis. [Online] Available at: http://www.orgsyn.org/ [Accessed 29 March 2013].