RECRYSTALLIZATION OF ACETANILIDE

Carmina Pea, Martin Lorenzo Pineda, Jan Marc Punongbayan, Maria Mediatrix Saraos, Nympha Elisa Sia, Bito Solima Jr. Group 8 2C Medical Technology Organic Chemistry Laboratory

ABSTRACT
Recrystallization was performed in the experiment. Recrystallization is a process of purifying organic substances through the difference in solubility at different temperatures. The general objective of this experiment is to produce acetanilide by the acetylation of aniline with acetic anhydride. Solubility test was performed to determine the recrystallizing solvent. The solution of distilled water, aniline, and acetic anhydride was placed in an Erlenmeyer flask. Then the solution was place in an ice bath and was filtered. The residue which was the crude acetanilide was dried and weighed afterwards. The crude acetanilide was dissolved in the recrystallizing solvent which is water and was placed in the heating water bath. After that, the solution was placed in an ice bath as crystals formed out again. Molecules of other compounds were excluded from growing crystal lattice, thus yielding pure acetanilide which is 4.04 %.

INTRODUCTION
Recrystallization is a process that involves the dissolution of the solid in an appropriate solvent at elevated temperature and the subsequent reformation of the crystals upon cooling. It is a method in which two crystallization processes is performed and also a method of purifying organic solids based on their solubility. Solubility is the property of solid, liquid, or gas called solute to be dissolved in a solvent to form a homogenous solution. It is a main factor that really affects recrystallization. Thats why, identifying a recrystallizing solvent is important. In fact, if we use inappropriate solvent, recrystallization may not be successful.

Figure 1. Structural formula of Aniline Aniline is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Aniline is a colorless, oily, poisonous liquid that boils at 182C when pure. The density of aniline is 1.0217 g/ml and its molecular weight is 93.13 g/mol. On air and light, it gradually darkens in color because of the oxidation due to atmospheric oxidation of an impurity present in benzene from which the aniline was prepared. Acetylation is a reaction which acetyl functional group is introduced in an organic compound. It is acetylated by warming mixture of aniline with acetic anhydride or even glacial acetic acid forming acetanilide.

C6H5NH2 + (CH3CO)2O C6H5NHCOCH3 + CH3COOH

Equation 1. Acetylation of Aniline with Acetic Anhydride to produe Acetanilide and Acetic Acid

Figure 2. Structural formula of Acetic anhydride

Acetic anhydride is a colorless liquid that produces a pungent vinegar-like odor when it reacts with water forming acetic acid. Its boiling point is 140C and the melting point is -73C. In liquid state, its density is 1.08 g/ml and its molecular weight is 102.09 g/mol. It plays an important role in the acetylation of aniline to form acetanilide.

Figure 3. Structural formula of Acetanilide Acetanilide is the product of the acetylation of aniline with acetic anhydride at low temperature. It is a white odorless flake solid that boils at 304C and melts at a range of 113-115C. Its density is 1.219 g/ml. This experiment aims to purify the crude acetanilide produced in the recrystallization and to calculate the percentage yield of pure acetanilide.

EXPERIMENTAL
A. SAMPLES USED aniline, acetic anhydride, pure acetanilide, distilled water, hexane, methanol, test tubes, beaker, filtration set-up (filter paper, funnel, tripod, receiving flask) B. PROCEDURE 1. Solubility Test A corn-grain amount of pure acetanilide was placed into each of the three test tubes. The first test tube contained 1 ml of distilled water. The test tube was shaken and placed n a warm water bath (37-40 C) for 1-5 minutes. Then it was cooled in an ice bath. The results of the solubility of pure acetanilide were recorded. The same procedure was done for methanol and hexane. 2. Recrystallization Process A 20 ml of distilled water and 2 ml aniline was placed in a dry Erlenmeyer flask. 3 ml of acetic anhydride was added slowly in the solution. All the changes were noted. After that, it was placed in an ice bath to hasten crystallization then it was filtered in a wet filter paper. The filtrate was discarded while the residue, which is the crude acetanilide, was dried and weighed using the analytical balance. A 20 ml recrystallizing solvent (water) was poured in the crude acetanilide then it was place in a hot plate until all solids were dissolved. Small amount of activated charcoal was added to remove colored impurities from the solution. The solution was quickly subjected to filtration using fluted filter paper while still hot. The filtrate was placed in a receiver containing cold water to hasten recrystallization. The crystals were washed using cold distilled water. Then, the collected crystals were dried by pressing-in between filter paper. The pure acetanilide was weighed using the analytical balance.

RESULTS AND DISCUSSION

Table 1 shows that three solvents namely: water, methanol, and hexane was tested. Methanol was soluble while hexane was insoluble in all the systems. This shows that acetanilide that will be place in this solvent cannot undergo recrystallization. On the other hand, water exhibited different results. It was insoluble at room temperature, soluble during heating, and insoluble upon cooling. Thus, water showed the desired solubility behavior of an ideal recrystallizing solvent for acetanilide. To support that, based on research, a recrystallizing solvent for acetanilide must be insoluble at room temperature. While heating, it should be soluble and upon cooling it must be insoluble. The applied amount of heat should not go beyond the melting point of the substance to be crystallized. The solid may melt in the solvent if the boilng point of the solvent is high. In that case, oiling may occur. It usually occurs when the solid substance melts and forms a liquid that is insoluble in the solvent. Upon cooling, the liquid refuses to crystallize, rather it becomes oil. Table 2. Weight of Crude Acetanilide, Pure Acetanilide and Percent Yield of Pure Acetanilide Wt. of crude acetanilide Wt. of pure acetanilide Percent Yield 2.2753 g 0.1201 g 4.04%

Table 2 shows the weight of crude acetanilide is 2.2753 g, weight of pure acetanilide is 0.1201 g, and percent yield is 4.04%.

The weight of the crude acetanilide is 2.2753 g. Acetylation of aniline and acetic anhydride contains small amount of impurities that may affect the weight of the substance from crystallization. During the recrystallization process, the solution was placed in a hot water bath. At that time, there were impurities that made the solution colored. Small amount of activated charcoal was added to the solution because it has a large surface area and it can remove impurities more effectively. Too much activated charcoal will not only adsorb the impurities but also the desired product thats why only small amount was added. When the acetanilide was dissolved, the solution was filtered immediately because filtering is the most effective way to remove solid impurities. The solution in the flask was kept in its boiling point to prevent premature crystallization. Washing of the crystals with cold water was done to help reduce the amount of solution remained in the crystals. Distilled water was used because its the recrystallizing solvent. However, during filtration, some part of the solution was lost that resulted to the reduction of the yielded pure acetanilide. Acetanilide crystals were dried by pressing-in of crystals with filter paper. The weight of the pure acetanilide is 0.1201 g. To calculate the percentage yield, the following should be identified: limiting reagent, actual yield, and theoretical yield. Limiting reagent is the reactant that is completely consumed in a chemical reaction. Actual yield is the amount of product that actually yielded. Theoretical yield is the quantity of product that is calculated to form when all the limiting reactant is consumed in a reaction. To calculate for the limiting reagent: Aniline= amount of sample used x density x molar mass = 2ml x (1.0217g/ml) x (mole/93.13g) = 0.0219 moles Acetic anhydride = amount of sample used x density x molar mass = 3ml x (1.08g/ml) x (mole/102.09 g) = 0.0317 moles Thus, aniline is the limiting reagent. To calculate for the theoretical yield: TY= mol LR x (mol acetanilide/mol aniline) x MW of acetanilide = 0.0219 n x (1 acetanilide/1 aniline) x (135.17g/mole) = 2.970 g To calculate for the % yield: % yield = (AY/TY) x 100 = (0.1201 g/2.970 g) x 100 = 4.04 % Therefore, this experiment, recrystallization, is a successful one because the researchers were able to attain the objectives. They were able to use the correct recrystallizing solvent. Thus, recrystallization took place. Their percentage yield is 4.04 %. This is the pure acetanilide obtained from the 2 ml aniline and 3 ml acetic anhydride.

REFERENCES
From book Bayquen, A., Cruz, C., de Guia, R., Lampa F., Pena G., Sarile, A., Torres, P., (2009). Laboratory Manual in Organic Chemistry. Philippines: C&E Publishing, Inc. p. 47

From the internet Blaber, M. Stoichiometry: Chemical Formulas and Equations http://www.mikeblaber.org/oldwine/chm1045/notes/Stoich/Limiting/Stoich07.htm 08/13/11 Guinne, R. Recrystallization of Acetanilide http://science.herograw.net/rob/chem12a-expt4.1.pdf 08/13/11 Wigal, C. Purifying Acetanilide by Recrystallization

http://www.cerlabs.com/experiments/1087540703X.pdf 08/13/11
ACETANILIDE http://chemicalland21.com/lifescience/phar/ACETANILIDE.htm 08/13/11 ACETIC ANHYDRIDE http://chemicalland21.com/petrochemical/acetic%20anhydride.htm 08/13/11