Synthesizing Acetylsalicylic Acid From Salicylic Acid Essay example

1086 Words Apr 10th, 2016 5 Pages
Synthesizing Acetylsalicylic Acid from Salicylic Acid

Shultz, Joshua T.

Chemistry 2210L


Figure 1. Esterification of Salicylic Acid to Yield Acetylsalicylic Acid

Figure 2. Acetyl Group Table 1. Reference Data, Experimental Volumes, Yields, and Melting Points
Melting Point of Salicylic Acid 158° C
Melting Point of Acetylsalicylic Acid 138° C - 140° C
Initial Mass of Salicylic Acid 0.510 g
Theoretical Yield of Acetylsalicylic Acid 0.665 g
Experimental Yield of Acetylsalicylic Acid 0.524 g
Percent Yield 78.8%
Melting Point of Initial Salicylic Acid 158° C - 160° C
Melting Point of Recovered Acetylsalicylic Acid 139° C - 146° C

Calculation 1. Theoretical Yield of Acetylsalicylic Acid with Salicylic Acid as the Limiting Reagent
0.510 "g C7H6O3"×(1 "mol C7H6O3 " )/(138.118 "g C7H6O3" )×(1 "mol C9H8O4 " )/(1 "mol C7H6O3 " )×(180.154 "g C9H8O4" )/(1 "mol C9H8O4 " )≈0.6652178 "g C7H6O3"

Calculation 2. Percent Yield of Acetylsalicylic Acid
"Yield (%) =" "Experimental Yield" /"Theoretical Yield" ×100=(0.5239 "g C9H8O4" )/(0.6652178 "g C9H8O4" )×100=78.8 %

To synthesize acetylsalicylic acid (i.e. aspirin), the experimenters combined 0.51 g of previously recovered salicylic acid with 1.25 mL of acetic anhydride and approximately 3 drops of concentrated sulfuric acid in a 50 mL Erlenmeyer flask with a spin bar. After swirling to dissolve the salicylic acid, the experimenters warmed the mixture for 10 minutes on a heat block with the spin bar stirring.…

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