RECRYSTALLIZATION: PURIFICATION OF ACETANILIDE

Chiquete Mariel Manzano, Anselm John Marcelo, Jerel Marquez, Hanz Christian Mendez, Lea Ramona Mercado

ABSTRACT
The purpose of this experiment is to determine the amount of pure acetanilide from the crude acetanilide, it is synthesize by means of recrystallization, whereas we dissolve the crude (solid) acetanilide to be crystallized in a hot solvent mixture and slowly cooled to obtain Crystals, this process is based on the premise that the solubility of a compound in a solvent increases with the temperature. Conversely, the solubility of the compound decreases as the solution cools. Polar solvents should be used in order to remove polar impurities and solubilized polar compounds; use nonpolar substances to remove nonpolar likewise. At the end of this experiment it is expected to obtain pure acetanilide from the crude acetanilide.

INTRODUCTION
Selecting an appropriate recrystallizing solvent to use is a difficult step in performing recrystallization. This is essential in order to effectively obtain pure acetanilide; usually there are several solvents that are used to test the solubility. In this experiment methanol hexane and water are the solvents that are going to be used. Recrystallization is a simple process whereas separation of pure substance from the crude ones. In this experiment we use organic substances which are easier to purify than inorganic substances, these came from the nature. There are 3 types of recrystallization process namely single solvent recrystallization, multi solvent recrystallization and hot filtration recrystallization. Acetanilide is an odorless solid chemical of leaf or flake like appearances. It is also known as N-phenylacetamide, acetanil or as the common name acetanilide and formerly known as antifebrin. It is also used as an inhibitor for peroxides. In the field of pharmaceutical it is used as a precursor in penicillin synthesis and some pain killers. Phenylacetamide structure shows analgesic and antipyretic effects; however it may cause methemoglobinema. Aniline is a Primary amine in which the amino group is directly attached to the benzene ring and the final product of the reduction of most nitrogen derivatives of benzene. It is slightly soluble in water and almost readily mixes with most organic solvents, it has a density of 1.0217g/mol and a molecular weight of 93.13g/mol. In the industry it is used to make polyurethane foams, farm chemicals and herbicides. Acetic anhydride or acetyl ether is a clear colorless liquid which has vinegar like smell and has a very strong scent. It combines with water to form acetic acid. It is soluble in both ether and chloroform. In the industry it is used to

manufacture pigments, dyes, cellulose and pestcides likewise. Acetic anhydrides main purpose in the experiment is to form acetylation of aniline or formation of acetanilide.

Figure 1: The Chemical Reaction forming Acetanilide.

. The experiment aims to synthesize acetanilide by acetylation, purification of the crude acetanilide bye recrystallization and calculation of the needed datas.

PROCEDURES 1. Materials needed:

Erlenmeyer flask, test tubes, Bunsen burner, tripod, wire gauze beaker, filter paper, aniline, hexane, acetic anhydride, methanol.

Figure 2: Erlenmeyer Containing the Crude acetanilide

2. Methodology:
A corn-grain amount of acetanilide was placed into each of the three test tubes, in the first test tube, warm water is used, about 1 ml; shake the test tube and put in a warm bath (37-40C), allow this to cool. The same procedure is done for both hexane and methanol respectively. note that This procedure is done in order to determine what solvent will be used in the recrystallization process.

After checking if the solids are dissolved and if the solution is slightly colored, add small amounts of charcoal to absorb the colored impurities. However if the solution is colorless, it must be quickly filtered while still hot; a fluted filter paper is used. The filtrate is allowed to cool. The crystals were then collected to be washed by distilled water and to be measured in a analytical balance.

Figure 5: Filtration of the Crude acetanilide Figure 3: The End product.

3.

In forming the crude acetanilide, 2ml of aniline and 20 ml distilled water were mixed in a Erlenmeyer flask. A 3 ml acetic anhydride was then added slowly in the solution. All the changes were noted. It is then placed in ice bath and filter through a wet filter paper, the crude acetanilide was dried and weigh using a analytical balance. Pour 20 ml recrystallizing solvent into the crude acetanilide; to be placed in a hot bath until the solids are dissolved.

Results and Discussion: The first step for recrystallization is to choose the solvent that is suitable solvent, it also must show the desired solubility behavior for the substance to be crystallized; identifying the solvent is a must, this is vital for the purification process. It also must (1) has to be soluble in hot temperatures (2) it must not be readily soluble in room temperature (3) must not be soluble in cold temperatures.
SOLVENT ROOM TEMPERATU RE INSOLUBLE SOLUBLE INSOLUBLE HEATED TEMPERATU RE SOLUBLE SOLUBLE INSOLUBLE COOL TEMPERATU RE INSOLUBLE SOLUBLE IN SOLUBLE

WATER METHAN OL HEXANE

Figure 4: Cold Bath for the Crystallization process.

Three solvents (above chart) were tested for solubility. In room temperatures, water and hexane showed to be insoluble, while methanol was readily soluble. In heated temperatures both water and methanol were soluble while hexane was still not. In cooled temperatures both water and hexane were insoluble and methanol to be the only soluble; therefore based on the results, methanol is not the ideal solvent: it shows to be soluble in room and heated temperatures but not in cool temperatures; which we need not to be soluble in order to form crystals, hexane on the other hand were insoluble in all of the needed categories, while water appears to be insoluble in room temperature, but it is soluble in

heated temperatures; which is need to separate the impurities and in turn insoluble in cool temperatures which is needed to form crystals in the cooling process.

Figure 6: Pure Acetanilide

Figure 8: Steps in Heating the Acetanilide.

Weigh of pure acetanilide: 1.4g Weigh of crude acetanilide: 2.9g %yield=actual yield/ theoretical yield x 100 1.4g/2.9gx100=48.27%

REFERENCES:
Books: Bayquen, A., Cruz, C. et.al. (2009). Laboratory Manual in Organic Chemistry. Philippines: C & E Publishing, Inc. Pg. 474 Hornback, J., Introduction to organic chemistry, brooks-cole publishing. Mcmurry, john, Fundamentals of organic chemistry, brooks-cole publishing. Websites: http://darwin.chem.villanova.edu/~bausch/CHM_2201/Fa10/Acetan ilide_Prep_Recryst.pdf http://www.chem.uiuc.edu/chem233smith/smithsyllabus/chem234r ecrystlab.html http://www.utdallas.edu/~scortes/ochem/OChem_Lab1/recit_notes /guide_to_lab_reports_08.pdf http://www.cerlabs.com/experiments/1087540703X.pdf http://www.villanovaorgo.com/labs/chm2201/fall-semester/week2preparation-recrystallization-acetanilide http://science.herograw.net/rob/chem12a-expt4.1.pdf http://www.chm.uri.edu/bdeboef/chm292/rextallization.pdf http://www.neiu.edu/~rdpurtuc/iSchool/chem/orgchem1/Org-Lab03.pdf http://www.neiu.edu/~jpgabrai/Lab%20703/lab703.htm http://www.chem.siu.edu/chem341/c341lectures/c341recrystallizat ion.pdf http://nsac.ca/envsci/staff/jhoyle/cs110/chem%202000/expt2.htm

Figure 7: Comparison of the Crude and the Pure Acetanilide.

The percentage yield is 48.27% based on the experiment. It is the pure acetanilide present on the crude acetanilide. The melting point of the pure acetanilide is 130C-132C based on this data, the acetanilide obtained was not totally pure, because the melting point of pure acetanilide ranges from 113C-114C. further purification or addition of activated charcoal is advised to be added in order to remove the impurities.