PREPARATION OF ACETYLSALICYLIC ACID ( ASPIRIN )

Abstract: Acetic anhydride and salicylic acid is reacted under high temperatures. However, simply increasing the reaction temperature isnt enough. A catalyst is also needed as salicylic acid is stabilized by its benzene ring, with lone pairs from the carbonyl group and the hydroxyl group delocalizing with the electrons of the aromatic ring. In this case, we utilized sulfuric acid (H2SO4) as the reaction catalyst. Salicylic acid can be easily synthesized via the hydrolysis of methyl salicylate or through the Kolbe-Schmitt reaction, which heats sodium phenoxide with CO2 under high temperature and pressure. It can also be extracted from willow bark. The other reagent in this reaction, acetic anhydride, is commonly produced via the carbonylation of methyl acetate.

Results: MW (g/mol) Salicylic acid Acetic anhydride Acetylsalicylic acid 138.1 102.1 180.2 Mass (g) 2.0040 5.4 0.3875 Volumes (mL) 5.0 Num. of moles 0.0145 0.0529 0.0160 Density (g/mL) 1.08 -

Melting point of acetylsalicylic acid = 129

- 134

Actual yield of acetylsalicylic acid = 0.3875g Percentage yield =

Purification test (1st) Reactant Water + Salicylic acid + Ferric chloride Observation Colourless solution turns to dark purple

Water + Acetylsalicylic acid + Ferric Colourless solution turns to light purple chloride Water + Ferric chloride Colourless solution turns to yellow

Purification test ( after recrystallization) Reactant Water + Salicylic acid + Ferric chloride Observation Colourless solution turns to dark purple

Water + Acetylsalicylic acid + Ferric Colourless solution turns to yellow chloride Water + Ferric chloride Colourless solution turns to yellow

Discussion: In the purification test, the result for test tube 1 (water + salicylic acid + ferric chloride) and test tube 2 (water + ferric chloride) are the same for both part of the test. Unlike for the remaining test tube, the result for before and after recrystallization is distinctive. For 1 st purification test, the presence of purple colour is obtained. This indicates that there is still some salicylic acid left in the product which also means that the reactants are not fully reacted. Thus, recrystallization is required. The first and third test tube is use to compare whether the product is purified of still contain the reactant. The low yield and purity that we obtained in this experiment are not only attributed to the experimental procedure and mechanism, but also to other experimental flaws. The low yields could be due to several factors, such as disturbance during crystallization, incomplete reaction and overheating. After all, crystal formation is highly dependent on critical temperature and the level of disturbance the saturated solution is subjected to. Similar to previous experiments, the usage of filter paper containing paper pulp reduced experimental yields as some product was left behind in the Buchner funnel and on the filter paper after suction filtration. Some were also stuck amongst the fibers of the filter paper that we utilized.

Experimental Procedure: Firstly, 2 grams of salicylic acid was added to a 125 mL Erlenmyer flask. This was followed by 5 mL of acetic anhydride and 5 drops of concentrated sulfuric acid (H2SO4). The flask was then swirled gently. Next, a condenser was fitted to the flask, with cold water flowing into the bottom of the condenser and warmed water flowing out from the top of the condenser. This continuous flow of cold water was generated by an electrical pump and helped to ensure that solvents and reagents remained in the reaction when undergoing reflux. The color of the reaction mixture is expected to change from white to colorless after much heating. When this finally happened, heating was stopped and the round-bottom flask was left at room temperature to cool. When the flask became cool to the touch, the condenser was removed and disconnected. The round-bottom flask was then cooled in an ice water bath till crystals stopped forming. After a substantial amount of time, only a minute amount of crystals were formed. Thus, we resorted to using a glass rod to scratch the sides of the flask. This enabled us to produce a larger amount of crystals. 50 mL of cold deionized water was then added to the round-bottom flask and stirred with a glass rod. Suction filtration was used to recover the white precipitate, and another 50 mL of cold deionized water was used to wash them. A mixed-solvent solution was made by mixing 8 mL of ethanol with 25 mL of water in a 100 mL conical flask. This was to recrystallize the white precipitate that we synthesized. However, contrary to the experimental protocol we did not use up all the solvent. After crystals stopped forming, they were filtered out under suction filtration and then left to dry under infra-red. The crystals were observed to be white and needle-like. Finally, the yield and melting point range were determined and recorded.

References: 1. Solomons and Fryhle. 10th Edition. Organic Chemistry. Wiley 2011 2. wwwchem.csustan.edu/consumer/aspirincons/aspirincons.htm 3. http://www.lahc.edu/classes/chemistry/arias/Exp%205%20-%20AspirinF11.pdf