The -OH in acetic acid is not a very good leaving group so converting it to an ester is more complicated unlike acetic anhydride which is easier to do so.
The balanced equation for the reaction between salicylic acid and acetic anhydride to form aspirin (acetylsalicylic acid) is: salicylic acid + acetic anhydride → aspirin + acetic acid.
The ingredients needed to produce aspirin are salicylic acid and acetic anhydride. Acetic acid is also produced as a byproduct during the chemical reaction.
37.16% is the expected yield in the reaction of salicylic acid and acetic anhydride used to form aspirin.
It is not recommended to prepare acetic anhydride at home due to its hazardous nature. Acetic anhydride is a highly reactive and flammable chemical that should only be handled by professionals in a controlled laboratory setting. Producing it at home can be extremely dangerous and is illegal in many locations.
Aspirin is generally produced by the following mechanism (starting from basic materials) Phenol --(NaOH, CO2, heat)--> Sodium Salicylate (+para isomer) --(H2SO4)--> Salicylic acid --(acetic anhydride)--> acetylsalicylic acid (Aspirin) Due to the myriad of organic reactions, there are multiple possibilities at each stage. However, the above is the most efficient and common way of synthesizing Aspirin. For example, the last reaction (esterification) may be accomplished by using an acyl halide instead of an anhydride (e.g. ethanoyl/acetic chloride instead of acetic anhydride). However, the acyl halide is more costly to synthesize and more unstable to handle.
The reaction between salicylic acid and acetic anhydride involves the substitution of a hydroxyl group in salicylic acid with an acetyl group from acetic anhydride. This reaction is catalyzed by an acid, typically sulfuric acid, and results in the formation of aspirin and acetic acid as byproducts.
Dehydration of acetic acid to prepare acetic anhydride occur at 8oo oC.
The reaction is: (CH3CO)2O + H2O = 2 CH3COOH
The chemical reaction between acetic anhydride and salicylic acid is called esterification. This reaction forms acetylsalicylic acid, which is commonly known as aspirin.
Aspirin is made when salicylic acid and acetic anhydride is reacted in the presence of an acid catalyst such as H2SO4. Acetylsalicylic acid (aspirin) and acetic acid is formed. The reaction is an esterification reaction.
Acetanilide can also be synthesized by reacting aniline with acetic anhydride, instead of acetyl chloride. This is known as the Acetic Anhydride Method.
The main impurties are probably the unreacted reactants. i.e salicylic acid and some acetic anhydride (ethanoic anhydride)