Synthesis of Aspirin from Salicylic Acid

Joe Julian CH:221:12 Tuesday, 1-4 PM September 14, 2004

The purity of the synthesized aspirin was measured by determining its melting point. which is the acetyl derivative of salicylic acid1. This aspirin derivative greatly reduced. He synthesized acetylsalicylic acid. salicylic acid. and swelling1. a safer derivative of aspirin was discovered by a German chemist named Felix Hoffman1. The product had a low percent yield and was found to be impure due to its low melting point. a pure sample of aspirin with a high percent yield would have been obtained. If the experiment went as expected. Fortunately. the melting point of aspirin was then measured using a Thomas-Hoover UniMelt device. In this experiment.Abstract Aspirin (acetylsalicylic acid) is a derivative of salicylic acid with the same medicinal values but fewer side effects. aspirin was synthesized from salicylic acid and acetic anhydride. In this experiment. which is aspirin poisoning2. Introduction The active ingredient in willow bark. Soluble impurities increase the range over which a compound melts and often decreases its overall melting point temperature4. Some of these side effects include stomach ulcers and salicylism. the side effects of salicylic acid. The amount of each compound should be the same because there is a 1:1 ratio between them (see Equation 1). but not entirely eliminated. To determine the product’s purity. acetylsalicylic acid was synthesized from the acidification of salicylic acid and acetic anhydride (see Figure 1). It is used widely as a pain killer and anti-inflammatory. The objective was to convert a specific amount of salicylic acid into the same amount of aspirin that was high in purity. 2 . is known to have medicinal values for alleviating pain. fever. salicylic acid can have potentially serious side effects in certain people1. Unfortunately.

0g of salicylic acid. (Equation 1) Experimental Procedure In a 50mL Erlenmeyer flask. The esterification of salicylic acid by acetic anhydride3. and 2 drops of concentrated sulfuric acid were added. the solution was allowed to heat for an additional 10 minutes. Once the dissolution of the salicylic acid occurred. 2mL of acetic anhydride. The solution was then allowed to cool until crystals began forming. The exact amount of salicylic acid used was recorded. The mixture was thoroughly mixed with a glass rod. To the solution. 1.Figure 1. 15mL of cold distilled water was added and a glass rod was used to break-up any lumps that had 3 . The mixture was warmed in a water bath that was kept inbetween 50°-60°C and was stirred until the salicylic acid dissolved.

formed. The percent yield was then calculated. The crystals were washed with cold distilled water until only the crystals remained. The theoretical yield of acetylsalicylic acid based on the amount of salicylic acid used for the reaction. The solution was swirled to mix and then cooled slowly to room temperature. The solution was cooled in an ice bath until it was completely crystallized then the crystals were collected via vacuum filtration.5mL for a total of 10. The aspirin was then collected via vacuum filtration and washed with cold distilled water until only the aspirin crystals remained. Results The following tables showing percent yield and purity of the synthesized aspirin were the data used to determine the success of the experiment. The aspirin was dissolved in 10mL of boiling 95% ethanol. The ethanol-aspirin mixture was reheated when the ethanol stopped boiling upon being added to the aspirin in order to dissolve the aspirin. Compound Acetylsalicylic 1. then adding another 0. The solution was placed on ice and the bottom of the glass was scratched with a glass rod to induce crystallization. weighed. The product was weighed and dried.76g 72% acid Table 1. and then transferred to a 125mL Erlenmeyer flask. The melting point of the synthesized aspirin was found by using a Thomas-Hoover UniMelt device.5mL of ethanol used. Theoretical Yield (g) Actual Yield (g) Percent Yield 4 . Twice the volume of cold water (21mL) was added to the mixture while the ethanol was still boiling. Two trials were done to confirm the temperature.06g 0. All results were then tabulated. The product (aspirin) was dried.

Further analysis of the product will have to be done to determine exactly how pure the product actually was.73g = 2. Calculation of mass of crude product before recrystallization of aspirin: Mass of 125mL Erlenmeyer flask = 91.p.06g of salicylic acid was used.76g of the product was acetylsalicylic acid.73g Mass of flask w/ crude product = 93. Since there is a 1:1 ratio between the two. When dissolving the initial amount of salicylic acid in the solution of acetic anhydride and concentrated sulfuric acid.76g of acetylsalicylic acid was harvested when 1. This could have some effect on the purity.p.12g crude product Observed m.Compound Acetylsalicylic 120-121 138 acid Table 2. (°C) ° Literature m. it is highly likely that less than 0. As Table 1 shows. There were several problems that could have contributed to the low purity or mediocre percent yield. this is not the case. for 0. it did not completely dissolve into the solution. The observed melting point of acetylsalicylic acid compared to its literature melting point. for the melting point of the harvested acetylsalicylic acid was not close to the literature melting point (see Table 2).85g (Mass of flask w/ crude product) – (Mass of flask) = Mass of crude product 93. then the amount of salicylic acid used should be equal to the amount of acetylsalicylic acid recovered at the end of the experiment. Since the final product was determined not to be very pure.85g – 91. (C) Discussion Table 1 shows how much acetylsalicylic acid was synthesized compared to how much salicylic acid was used. even 5 .

when it was heated. Carman. Bell. The iron (III) chloride test also could have been ran to determine if any of the aspirin degraded to salicylic acid or never converted from salicylic acid. Accessed 15. University of Nevada. Joe Jeffers. Ronald J.. 2. Diana. Frederick A. Sept.G. Wikholm. The purity of the aspirin was not very high. Moses Lee. http://tooldoc. http://www. Susquehanna University. Benzaia. Accessed 18. 2004. 2004. 2003. Jan William Simek. To determine if this affected the synthesis of aspirin at all. 3. Jr. Landesberg. 2002. Dr. 4. Henry. Carl T. The reaction yielded only 72% of its expected product. Wigal. Joseph M. Loffredo. Charles E. 2003. Dr.. Hospital for Special Surgery. Joseph W. Synthesis of acetylsalicylic acid (aspirin).hss. Thomson Learning: Ohio. Conclusion The experiment did not go completely as expected.nevada. Bettelheim. Wade. This could have a slight impact on the results of the overall yield of aspirin because it was possible that not all of the salicylic acid was synthesized. 6 . References 1.wncc. 2004. Liotta. Geneive.htm. which is evident by the low melting point when compared to the literature value. Taber. Louis J. the experiment should have been ran a second time to see if the same thing occurred.T. A.. Sept. LeFevre. Clark. and William M. Allen K. Jerry Manion. Organic Chemistry Laboratory Manual: Susquehanna University. Douglass F. Rowland.

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