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Varying The amount of sulfuric acid in the synthesis of aspirin

By: Jess Withey and Dr. David Oostendorp, Ph.D. Varying The amount of sulfuric acid in the synthesis of aspirin. 1. Introduction. Aspirin is a true wonder drug. Used mostly as a pain reducer and fever fighter. Reduces the incidence of heart disease, strokes, and certain cancers.

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Varying The amount of sulfuric acid in the synthesis of aspirin

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  1. By: Jess Withey and Dr. David Oostendorp, Ph.D. Varying The amount of sulfuric acid in the synthesis of aspirin

  2. 1. Introduction • Aspirin is a true wonder drug. • Used mostly as a pain reducer and fever fighter. • Reduces the incidence of heart disease, strokes, and certain cancers. • Improves brain function in people who have suffered small strokes, prevents cataracts, and reduces the occurrences of gallstones.

  3. 2. Objective • Use infrared (IR) spectroscopy to observe the effect of acid catalyst (sulfuric acid) in the synthesis of aspirin • IRs are analytical techniques used to identify functional groups in a molecule based on their absorption of electromagnetic radiation in the infrared region. • Calculate and compare percent yields

  4. 3. Reaction

  5. 4. Chemical List • 30mL distilled water • 15.0mmol salicyclic acid • 5.0mL acetic anhydride • Concentrated sulfuric acid (0.0-0.4mL) • Ice

  6. 5. Methods: REACTION PROCESS: • Mix 15.0 mmol (about 2.0g) acetic anhydride and 5.0 mL salicyclic acid in Erlenmeyer flask. • Concentrated sulfuric acid was added with stirring. • Mixture was heated for 6 minutes at 45-50 degrees Celcius. • Mixture was set out to cool and crystallization occurred. • 30.0mL of water was added; clumps were broke apart using a stirring rod. • Mixture was placed in ice for a couple minutes to become solid-like.

  7. SEPARATION PROCESS: • Mixture was separated using vacuum filtration • Mixture was washed with cold water • Product was saved and dried

  8. 6. Results • Experiment was performed 15 times. • Three total trials for each amount of H2SO4. • The amount of H2SO4 added ranged from 0 to 0.4mL. • Products were similar in color, amounts and texture varied.

  9. Figure 1:Below shows the percent yields in comparison to the amount of sulfuric acid that was added to the reaction.

  10. Crystallization Process • 0.0mL-sugar, water mixture whole time • 0.1mL-clear right away, 5 minutes • 0.2mL-6 minutes • 0.3mL-during reaction, 3 minutes • 0.4mL-clear right away, 5 minutes

  11. Figure 2:Below is the infrared spectroscopy of Aspirin as a result of the experiment for 0.1mL.

  12. Figure 3: Below is the actual infrared spectroscopy of Aspirin.

  13. Figure 4: Below is the infrared spectroscopy of Aspirin as a result of the experiment for 0.2mL (actual experiment).

  14. 7. Conclusion • Results indicate that there is a general trend that the percent yield increases with the addition of sulfuric acid. • Time varied to crystallize in reaction process. • The experiment’s infrared spectroscopy is verified to be Aspirin.

  15. 8. References • Oostendorp, Dr. David. The Prentice Hall Custom Laboratory Program for Chemistry; Pearson Learning Solutions: Boston, MA, 2010; pp173-180. • Smith, Janice Gorzynski. Organic Chemistry, 3rded.; McGraw-Hill: New York, 2008; pp 476-477.

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