RECRYSTALLIZATION Maria Janine B. Abarientos, Kuia B. Allarde, Aliana Keshia P. Andino Mary Viadelle E.

Andrada and Nina Marian Robelea G. Ang Group 1 2C Pharmacy Organic Chemistry Laboratory ABSTRACT
Recrystallization was used as the method in purifying crude acetanilide (organic compound) through the difference in solubility. In this experiment, the crude acetanilide was dissolved in a recrystallizing solvent in a water bath and the solution gained, was cooled in an ice bath as crystals form out. As the compound crystallizes from the solution, the other compounds molecules dissolved and are excluded from growing crystals, yielding pure acetanilide.

INTRODUCTION
This experiment aims to make the students capable of synthesizing acetanilide by the acetylation of aniline. This experiment also aims for the students to purify crude acetanilide product by using the method, recrystallization. Organic compounds, that are solid at room temperature are usually purified by using the method of crystallization. Crystallization is the deposition of crystals from a solution. During the process when the crystal are starting to form, a molecule have the tendency to be attached to a growing crystal composed with the same type of molecules because of a better fit in a crystal lattice of a molecule of the same structure than for other molecule. Solubility is the degree of substance, which is the solute to be dissolved in solvent. It is the main factor that affects crystallization. Before performing crystallization, identifying the best recrystallizing solvent is significant. Recrystallization is a procedure that is often used to 'purify' organic compounds that are obtained in an impure state from a chemical reaction or extraction process. The compound to be purified, a solid at room temperature, is dissolved in a hot solvent, filtered (usually by gravity) and allowed to cool. The purified compound will then crystallize out of the solution. Separation of the purified compound from the 'mother liquor' is achieved by filtration (usually by vacuum) followed by air drying. Typically purity is 90% after one recrystallization step (99%, 99.9% after two and three recrystallizations respectively).

B. Procedure 1. Selecting The Best Recrystallizing Solvent

In the process of recrystallization, the best recrystallizing solvent should be chosen first. One member placed a corn-rain amount of pure acetanilide in each of three test tubes. To the first test tube, and added 1mL of water. The test tube was then shaken and placed in warm water bath, the temperature preferably 37-40oC, for 15 minutes. Table 1. Structure of selecting the best solvent compounds used in

Compound methanol

hexane

The solution was allowed to cool and observations were recorded. The same process was done to the second and third test tubes using methanol and hexane respectively.

2.

Recrystallization

EXPERIMENTAL A. Compounds Tested

- Crude Acetanilide, Aniline - Water, Methanol, Hexane

In the recrystallization process, the members of the group mixed 2ML of aniline and 20mL of distilled water in an Erlenmeyer flask. Then, 3mL of acetic anhydride was slowly added.

Figure 1. Structural Formula of Aniline

all system. This shows these solvents are not the best recrystallizing solvents. However, distilled water exhibits different result; rather, it shows the desired solubility behavior of an ideal recrystallizing solvent for acetanilide. At room temperature it was insoluble; during heating it was soluble; and when placed upon cooling it was insoluble. Result shows that water is the best recrystallizing solvent. Crude acetanilide was taken from the filtered mixture of 2mL aniline and 20mL of distilled water and measured for the later part of the computations. The weight of the crude acetanilide is 2.97g. Absorption of heat is exhibited when acetanilide is placed in a hot water bath, thus, the solute dissolves in the solvent, and was filtered while hot while in an ice bath. Filtering is most effective way to remove solid impurities. The solution in the flask should be kept in its boiling point temperatures to prevent premature crystallization. Premature crystallization may contain some of the impurities from the solvent. After cooling crystals were formed. Hastening crystallization is done through ice bath. The crystals were collected and filtered again Acetanilide crystals were dried by pressing-in of crystals with filter paper. During the process, some of the residue was not weighed because the particles were attached to some part of the filter paper. The weight of the pure acetanilide was reduced to 1.9091g. Table 3. The actual yield of crude and pure acetanilide, and the percent yield of pure acetanilide
Weight of acetanilide the crude pure 2.97 g 1.9091 g 64.28%

Figure 2. Structural formula of Acetic Anhydride All changes in the solutions were noted. The solution was then cooled in an ice bath to hasten crystallization. After, cooling the solution was filtered through a wet filter paper. Then, crude acetanilide was dried and weighed.

Figure 2. Structural formula of Acetanilde After the chemical was weighed, 20mL of recrystallizing was poured into the crude acetanilide. Next, it was heated in a hot water bath until all of the solid particles dissolved. The solution was quickly filtered while containing tap water. Afterwards, the crystals were collected and washed with distilled water. One of the group members pressed in-between the filter paper for it to dry. Pure acetanilide was weighed and its melting point was determined.

RESULTS AND DISCUSSION

The primary step for recrytallization, Identification of the best recrystallizing agent was needed. In choosing the recrystallizing solvent it should be (1) Insoluble at room temperature, (2) Soluble during heating and (3) Insoluble upon heating. Table 2. Solubility of pure acetanilide in various substances
water methanol hexane At room temp. insoluble soluble soluble During heating soluble soluble insoluble Upon cooling insoluble soluble insoluble

Weight of acetanilide Percentage Yield

To calculate the percentage yield, the limiting reagent and theoretical yield should be identified. Limiting reagent is the reactant that is used up first in a reaction. Theoretical yield is the maximum yield of pure crystals that could be obtained by cooling or evaporating a given solution. This refers to the quantity of pure crystals taken from the solution.

On Table 2, there were three solvents that was tested, distilled water, methanol and hexane. Methanol is soluble while hexane is insoluble in

The following chemical reaction was used for computing the limiting reagent and the theoretical yield:

[5]Pavia, D. L., Lampman, G. M., Kriz, G. S., & Engel, R. G. (1999). Organic Laboratory Techniques: A Microscale Approarch (3rd Ed.). Harcourt College Publiser. Pg. 558-576 [6]Recrystallization http://en.wikipedia.org/wiki/Recrystallization_(ch emistry) AUGUST 17,2011 [7]Synthesis of Recrystallization of Acetanilide http://www.csub.edu/chemistry/331/ExampleLab .pdf AUGUST 17, 2011

The following equation shows how to compute the limiting reagent: 2mL aniline x 1.02g 1 mL 2mL acetic x 1.08g anhydride 1 mL Computing acetanilide x x 1n 93g 1n 102g yield (TY) of = 0.032 n = 0.022 n

for the theoretical 1n acetanilide x 1n aniline = 2.97 g acetanilide

0.022n aniline x

135 g 1n acetanlide

The following equation is used to compute the percentage yield (%yield): %yield= actual yield (g) theoretical yield (g) %yield = 0.5g 10g = 64.28% X 100% X 100%

REFERENCES
[1]ACETIC ANHYDRIDE (ACETYL ETHER). (n.d.)http://chemicalland21.com/petrochemical/A CETIC%20ANHYDRIDE.htm AUGUST 17, 2011 [2]ACETANILIDE (N-PHENYLACETAMIDE). (n.d.)http://chemicalland21.com/lifescience/phar /ACETANILIDE.htm AUGUST 17,2011 [3]Bayquen A. et.al.(2009).Laboratory Manual in Organic Chemistry.Quezon City: C&E Publishing Inc. [4]Pastro, D. J., John, C. R., & Miller, M. S. (1998). Experiment and Techniques in Organic Chemistry. New Jersey: Prentice Hall. Pg. 43-46