IV. DATA Table 11.1. Description of the samples.

SAMPLE Salicyclic acid Acetic anhydride 85% Phosphoric acid 95% ethanol Distilled water FeCl3 KMnO4 Iodine solution Crude aspirin Synthesized aspirin Commercial aspirin

OBSERVATIONS White powder Clear, colorless liquid Clear, colorless liquid Clear, colorless liquid Clear, colorless liquid

Red-orange liquid Small, white crystals Small, fine white crystals

Table 11.2. Observations on the preparation of acetylsalicyclic acid. SAMPLE OBSERVATIONS Salicyclic acid + Acetic anhydride + Phosphoric acid Cloudy, colorless liquid After heating Clear, faint yellow liquid + Distilled water Evolution of gas, rancid odor + Ice-cold distilled water Formation of white precipitates After suction filtration Filtrate is clear colorless liquid, residue are white small crystals Final appearance of crystals Small, white crystals

Table 11.3. Mass and percentage yield of synthesized acetylsalicyclic acid. Mass of watchglass + filter paper 42.57 g Mass of watchglass + filter paper + crude aspirin 46.87 g Mass of crude aspirin 4.30 g Theoretical yield 2.6 g % yield of crude aspirin 170%

Table 11.4. Observations on the recrystallization of acetylsalicyclic acid. SAMPLE OBSERVATIONS Crude aspirin + 95% ethanol Crude aspirin was dissolved, clear liquid + Distilled water Solution became cloudy In ice bath Formation of crystals After suction filtration Filtrate is clear, colorless liquid, residue is fine white crystals Final appearance of product Fine white crystals

Table 11.5. Mass and percentage recovery of recrystallized acetylsalicyclic acid. Mass of watchglass + filter paper 42.65 g Mass of watchglass + filter paper + recrystallized acetylsalicyclic acid 44.37 g Mass of recrystallized acetylsalicyclic acid 1.72 g % recovery of recrystallized acetylsalicyclic acid 40%

Table 11.6. Melting points of crude and recrystallized acetylsalicyclic acid. CONDITIONS CRUDE SAMPLE RECRYSTALLIZED SAMPLE Literature value of melting point of aspirin 138C Temperature when melting starts (C) Temperature when melting completes (C) Melting point range (C)

Table 11.7. Observations on the characterization of aspirin and starting materials. SAMPLE TESTS AND OBSERVATIONS Solubility in H2O (+/-) FeCl3 (+/-) KMnO4 Salicyclic acid Cloudy solution Purple-colored + Disappearance liquid of purple color, formation of black precipitates Acetic anhydride Homogeneous, + Yellow-orange Purple-colored clear colorless liquid liquid liquid Acetylsalicyclic acid Crystals settled Light brown Purple-colored at bottom liquid liquid

(+/-) +

Table 11.8. Differentiation of synthesized aspirin and commercial aspirin. SAMPLE OBSERVATIONS Synthesized aspirin Black liquid Commercial aspirin Formation of black precipitates

(+/-) +

V. SAMPLE CALCULATIONS Determination of limiting reagent: C7H6O3 + C4H6O3 2 g C7H6O3 5 mL C4H6O3 = 5 g C4H6O3 # of moles of C7H6O3 = 2 g C7H6O3 (1 mol C7H6O3/138.12 g) = 0.014 mol C7H6O3 # of moles of C4H6O3 = 5 g C4H6O3 (1 mol C4H6O3/102.02 g) = 0.043 mol C4H6O3 0.014 mol C7H6O3 (1 mol C9H8O4/1 mol C7H6O3) = 0.014 mol C9H8O4 Limiting Reagent 0.043 mol C4H6O3 (1 mol C9H8O4/1 mol C4H6O3) = 0.043 mol C9H8O4 C9H8O4 + CH3COOH

Theoretical yield 2 g C7H6O3 (1 mol C7H6O3/138g)(1 mol C9H8O4/1 mol C7H6O3)(180 g/1 mol C9H8O4) =2.6 g C9H8O4

% yield for crude aspirin = (actual yield/theoretical yield) x 100 = (4.30 g/2.6 g) x 100 =170%

% recovery of recrystallized aspirin = (amount of recrystallized aspirin/amount of crude aspirin) x 100 = (1.72 g/4.30 g) x 100 =40%

VI. RESULTS AND DISCUSSION The reaction to produce aspirin is an example of an organic synthesis called esterification. It involves the acid-catalyzed reaction of a carbonyl (-COOH) group and a hydroxyl (-OH) group of an alcohol or phenol to produce a carboxylate ester. In the synthesis of aspirin, the hydroxyl group is the phenolic OH group attached to the ring of salicylic acid. The acetyl group (-COCH3) comes from acetic anhydride. In the preparation of acetylsalicyclic acid, the starting materials are salicyclic acid and acetic anhydride. The phosphoric acid acts as catalyst, since esterification is an acid-catalyzed reation. The resulting mixture was swirled and heated to aid in the dissolution of salicyclic acid. After heating, distilled water was added to convert remaining acetic anhydride to acetic acid. A vigorous reaction will be observed. This is due to the exothermic reaction of the breaking of bonds of the acetic anhydride. Ice-cold distilled water was added to hasten the crystallization process. Afterwards, suction filtration was used to separate the crystals from the liquid. The residue was washed with cold distilled water to remove impurities. The residue was then weighed, and the percent yield was calculated. The filtrate was a clear, colorless liquid, and the residue was small, white crystals. The residue is the synthesized crude aspirin. Recrystallization of the aspirin is then performed, to purify the product. The crude aspirin was dissolved in 95% ethanol instead of diethyl ether.