1. Synthesis and Strength Test of Aspirin Ian Fucci

2. What Is Aspirin? • Aspirin (or Acetylsalicylic Acid) is part of a group of drugs called salycilates. • It is used to treat pain in the body by lowering amounts of substances that cause pain. Synthesis and Strength Test of Aspirin

3. Where Did Aspirin Come From? • Aspirin was first derived from the bark of a willow tree. • The earliest known use of aspirin was traced back to the Greeks in the 400s B.C. Hippocrates described it as a bitter powder that reduced fevers. • The next step in aspirin development was the isolation of Salicin in 1829. Unfortunately, it was very acidic and irritated the stomach of people who ingested it. Synthesis and Strength Test of Aspirin

4. Modern Aspirin • The aspirin that we are used to appeared in 1897 when German chemist Felix Hoffman first synthesized acetylsalicylic aspirin. • In 1899, Bayer patented the drug and began (what is thought to be) the first pharmaceutical company • It was not until about 1970 when we first understood how aspirin worked. Synthesis and Strength Test of Aspirin

5. How Does it Work? • Aspirin is known to block production of compounds called prostaglandins. They are hormone-like substances that control various bodily functions. • Prostaglandins cause inflammation and swelling in response to some disease, but they also control vital functions. Synthesis and Strength Test of Aspirin

6. Chemical Makeup • Aspirin is also known as ASA or Acetylsalicylic Acid. • The official IUPAC name is 2-acetoxybenzoicacid • Its molecular formula is C9H8O4 StructuralFormula Synthesis and Strength Test of Aspirin

7. Synthesis Sulfuric Acid Salicylic Acid + Acetic Acid Acetylsalicylic Acid + Water Synthesis and Strength Test of Aspirin

8. In a Commercial Lab… • Aspirin is synthesized with either an organic halide (commonly acetyl chloride) that contains a acetyl group or acetic acid (or acetic anhydride) and salicylic acid. • The two ingredients are heated in a water bath, mixed, and then filtered and washed. • Buffers are later added to decrease acidity and reduce the chance of stomach irritation. Synthesis and Strength Test of Aspirin

9. In-Class Lab Purpose Materials Procedure Results Conclusion

10. Purpose • Part I: Synthesis of Aspirin • Purpose: Create aspirin from acetic and salicylic acid. • Part II: Strength Test of Aspirin • Purpose: Test the lab made aspirin’s strength against that of commercially made aspirin. Synthesis and Strength Test of Aspirin

11. Materials (Part I) • Ring Stand • Ring • Wire Gauze • Bunsen Burner • 600mL Beaker x2 • 200mL Beaker • Thermometer • tongs • stirring rods • Erlenmeyer Flask • Funnel • Filter Paper • Salicylic Acid • Acetic Acid • Sulfuric Acid • Ice Synthesis and Strength Test of Aspirin

12. Chemicals Acetic Acid Sulfuric Acid Salicylic Acid Synthesis and Strength Test of Aspirin

13. Procedure (Part I) • Place 7g of salicylic acid in a 200mL beaker. Under a hood, carefully add 14mL (15g) of acetic acid. • Add 8-10 drops of sulfuric acid to acidify the mixture. Stir. • Place beaker in warm water bath for 10-15 minutes. Do not permit the temperature of the mixture to go above 50 degrees Celsius. • Remove the beaker with tongs and cool in an ice bath. Stir until crystals appear. • Slowly add 100mL of water to remove any excess acid. Stir. • Filter using funnel and filter paper. • Wash crystals with a little ice water. • Remove crystals and let dry for at least 24 hours. Synthesis and Strength Test of Aspirin

14. Procedure Pictures Synthesis and Strength Test of Aspirin

15. Results (Part I) • The lab was a success in forming aspirin crystals. • Crystals were small, white granules. Synthesis and Strength Test of Aspirin

16. Materials (Part II) • Ring Stand • Buret and Buret Clamp • Erlenmeyer Flask • Lab-Made Aspirin • Western Family Aspirin • Bayer Aspirin • 0.1 N NaOH • Phenolphthalein Synthesis and Strength Test of Aspirin

17. Procedure (Part II) • Find weight of aspirin tablets • Dissolve tablets in 50 mL of distilled water. • Add several drops of phenolphthalein • Titrate with standardized 0.1 N NaOH solution until endpoint is reached. • Record volume of base • Calculate concentration of acetylsalicylic acid. Synthesis and Strength Test of Aspirin

18. Calculations Bayer: Western Family: Lab-Made: Synthesis and Strength Test of Aspirin

19. Results (Part II) • Bayer was the most concentrated solution in 50mL of water, followed by the lab-made aspirin, and then Western Family • Results may have been skewed due to buffer found in commercially produced aspirin, and aspirin’s low solubility in water. Synthesis and Strength Test of Aspirin

20. Conclusion The lab was successful in producing aspiring and testing its strength. As expected Bayer was the strongest, but the lab-made aspirin was second instead of the other commercial brand, which was the third most concentrated. The results, however, may have been skewed due to the buffer found in commercial grade aspirin and acetylsalicylic acid’s low solubility in water. Synthesis and Strength Test of Aspirin