Cruz, Heidy V. Group no.

12 3 ChEB Tuesday, 2:00- 5:00PM

Date Submitted: Feb 26, 2010

Experiment no. 3 Preparation of Aspirin and Determination of Its Melting Point
The experiment aimed to learn the preparation of aspirin in a laboratory setting and calculate the percentage yield of the reaction. It also aimed to determine the melting point of the substance; to apply the correct techniques in putting up a melting point assembly and assess the purity of the assessed aspirin through its melting point. The experiment involved three steps: synthesis of aspirin, isolation and purification and the estimation of purity of the final product. The synthesis involved the reaction of salicylic acid and acetic anhydride in the presence of a catalyst, phosphoric acid, H3PO4. When the aspirin was prepared, it was isolated and filtered. The percentage yield of the synthesis was calculated to be 97.66%. The experimental melting point range of aspirin was determined to be 110- 122°C. Due to its wide range, and lower value than that of the theoretical melting point of 136°C, it was assessed that the prepared aspirin was impure.


Introduction Aspirin, trade name for acetylsalicylic acid, is the most widely used drug for treating fever, pain, and inflammation. It is a salicylic acid derivative often called a wonder drug, and is now thought to have possible preventative effects against heart disease, stroke, forms of cancer, and other diseases and conditions [1].. Aspirin is thought to act by interfering with synthesis of prostaglandins, hormone-like chemicals in the body that have many functions. Prostaglandins are implicated in inflammation and fever. They also can induce pain and raise the sensitivity to pain, and they are responsible for making platelets stick together to

the mixture was filtered and was allowed to dry in the filter paper.0mL of acetic anhydride and about 20 to 25 drops of 85% H3PO4 were added to it.0g of salicylic acid was weighed then 3. and one of the several physical properties by which an organic compound is identified is its melting point. along with the Swedish researchers Sune Bergström and Bengt Samuelsson. In determining the melting point range of the aspirin. During the melting process. It was allowed to cool and was placed in an ice bath until the solution becomes cloudy. Using pre-weighed filter paper. 20 drops of distilled water was slowly added. or at least clearly enlarge its melting range [3]. British pharmacologist Sir John Vane. The melting point of a substance is the temperature at which the material changes from solid to a liquid state.form blood clots. 15mL of water was added then the solution was heated until it became clear. Pure crystalline substances have a clear. The mixture was warmed over a water bath for 5 minutes while stirring. shared the 1982 Nobel Prize in medicine for showing how aspirin works by blocking a particular enzyme needed to produce prostaglandins [2]. The capillary tube and a . a capillary tube (sealed at one end) was one-third-filled with the dried aspirin. all of the energy added to a substance is consumed as heat of fusion. II. and the temperature remains constant. After warming. This is because even small quantities of impurities change the melting point. Aspirin is an organic compound. sharply defined melting point. Determining the melting point is a simple and fast method used in many diverse areas of chemistry to obtain a first impression of the purity of a substance. Methodology 1.

Purification was necessary to remove any unreacted salicylic acid and acetic anhydride as well as the acetic product and phosphoric acid. The aspirin was insoluble in cold water and can be isolated by filtering the chilled reaction solution. The temperature at which the solid started to melt and the temperature when the entire sample was completely liquefied were recorded as the melting point temperature range. . H3PO4.thermometer were immersed in an oil bath. Figure 1 Actual Melting Point Range Setup III. as a catalyst: C7H6O3 + C4H603 H3PO4 C9H8O4 + C2H4O2 Once the aspirin was synthesized. Discussion of Results Aspirin was synthesized by reacting salicylic acid with acetic anhydride in the presence of phosphoric acid. it was allowed to crystallize by placing it to a cold bath.

Table 1 Preparation of Aspirin Mass of filter paper w/ aspirin Mass of Filter paper Experimental mass of aspirin Theoretical mass of aspirin Mass of salicylic acid %yield 2.Acetic acid and phosphoric acid are water soluble so they were removed by washing the aspirin with chilled water.4700g 1. It was then immersed in an oil bath and was heated. Since the boiling point of oil is higher than the expected melting point of aspirin.66% One way to know the purity of the aspirin was by determining its melting point. no bubbles would form yet inside the beaker.7438g 1. therefore making the .                   A high percentage yield means a successful synthesis [4] . Most of the reactants were converted to products and very minimal amount of the product was lost during purification. The experiment required a small amount of the sample to be firmly packed (to ensure efficient heat transfer) in a capillary tube. The theoretical yield of aspirin was determined by stoichiometry.2738g 1.0g 97. Table 1 shows the data obtained after the synthesis of aspirin.3043g 1.

" Microsoft® Student 2009 [DVD]. with a high percentage yield of 97. Synthesis of Aspirin. 2. Retrieved March 1 . Conclusion and Recommendation Aspirin was successfully synthesized from acetic anhydride and salicylic acid. References 1. 25. Mehta. A lower melting point and a melting point range of 5° or more indicates that a compound is impure [6] . 2008. This was due to the presence of impurities in the sample. The temperature range at which melting began and was completed is the melting point range. 2010. IV.chem. A. thermometer and an oil bath setup. In the experiment. (2005). The theoretical melting point of aspirin is 136 °C. Using a capillary tube. Redmond.latech.66%. which was caused by the contaminants during the preparation of the aspirin. the melting point obtained was 110-122 °C. from Louisiana Tech University: http://www. ( . 3. Aspirin.d.). "Aspirin.observations on the capillary tube easier [5] . Due to the encountered discrepancies in the obtained values. it is recommended that thorough cleanliness and accuracy must be observed when conducting the experiment to prevent further errors. It is because the presence of impurities or contaminants in a sample can lower the melting point and can broaden its melting point range. its melting point range of 110-122 °C was determined which was far to its actual melting point of 136°C. WA: Microsoft Corporation. Chemical Engineering News .

edu/index. 2010. 2010. from Worcester Polytechnic Institute : http://www. Determination of Melting Points. Retrieved March 1.4.).edu/home. 6. Laboratory Exercise 10: Melting Point and Boiling Point Determination.wpi.html 5.html .coloradomtn. (n.d. from Colorado Mountain College : http://www. Retrieved March 11. (n.). P. (2001. Retrieved March 1. Theoretical Yield and Useful Nomenclature.d. September 7). Jeschofnig. from CU Boulder Organic Chemistry Undergraduate Courses : http://orgchem.

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