ACETANILIDE PURIFICATION BY RECRYSTALLIZATION

Kathleen Anne Francisco, Ma.Casey Louisse Garcia, Aimee Dianne Hermoso, Frances Geraldine Ibale, Rigel Larga Group IV, 2EPharmacy, Faculty of Pharmacy, University of Santo Tomas

ABSTRACT

Recrystallization is a purification process for organic substances that are solid at room temperature. In this experiment, acetanilide was synthesized by the acetylation of aniline with acetic anhydride. Using a water bath, the crude acetanilide was dissolved in the recystallizing solvent. After the crude acetanilide was completely dissolved, it is filtered using a fluted filter paper and cooled in an ice bath until crystals were formed. The crystals were then collected and washed with distilled water. Limiting reagent, theoretical yield and percentage yield were then calculated. The limiting reagent is aniline. The theoretical yield is 2.70g and the percentage yield of the reaction is 29.63%. This is the percentage of pure acetanilide obtained from the acetylation of aniline and acetic anhydride.

INTRODUCTION Organic compounds that are synthesized in the laboratory or isolated from natural resources can contain impurities. An impurity, according to the Tooling University is an unwanted substance that Recrystallization is a

purification process used to remove impurities from organic compounds that are solid at room temperature (Wigal, C.). It is a technique that is based on the difference in the solubilities of the desired compound and the impurity the (impurities) desired

reduces the quality of a material. Thus, a purification process is

needed for the elimination of these impurities.

contaminating

compound, as a function of varying

temperature (Cerritos Community College). Choosing the appropriate

insoluble

in

solution

at

temperature above the compounds melting point. As a result, the compound is deposited as oil, not as crystals (Wigal, C.). Aniline,phenylamine or

recrystallizing solvent is a significant step in the recrystallization process. This will result in the production of a higher percentage yield of the

aminobenzene, is a primary amine. It has an amino group (-NH2) directly attached to a benzene ring with a chemical formula of C6H5NH2.It is a colourless liquid but darkens upon exposure to light and air. It is denser and slightly soluble to in water.

product. These are some of the criteria in choosing the suitable solvent for the recrystallization

process: (1) the crude crystals should have low solubility in the chosen solvent at room temperature; (2) the crude crystals should have high solubility in the chosen solvent when heated to boiling; (3) The crude crystals should not react with the solvent; (4) the solvent should boil at temperature below the solid melting point; (5) the solvent should

According

Encyclopedia

Britannica, it was first obtained in 1826 by the destructive distillation of indigo. Thus, taking its name from the indigo-yielding plant

Indigoferaanil(Indigoferasuffruticos a). It is an organic based used to make dyes, drugs, explosives,

moderately be volatile so crystals dried readily and (6) the solvent should be non-toxic, non-flammable, and inexpensive (Dr.Pahlavan). The impurities in reverse should be dissolved in the solvent at high and low temperatures. compounds If the solvents point, the

plastics and photographic and rubber chemicals.

boiling point is higher than the melting

Figure 1. Chemical Structure of Aniline

compound will oil out. Oiling out occurs when a compound is

Acetic

anhydride

(chemicaland21.com, retrieved July 28, 2013).

(CH3CO)2O, also known asAcetyl ether is a clear, colourless, mobile (free-flowing)liquid with a sharp odour similar to that of acetic acid. It hydrolyses in water to yield acetic acid. It is used in the manufacture of cellulose acetate for films and plastic goods. They are also used in the manufacture of industrial chemicals, pharmaceuticals, perfumes, synthetic fibers and explosives (Prof.

Figure 3. Chemical Structure of Acetanilide

The

objectives

of

the

experiment are: (1) to synthesize acetanilide by the acetylation of

Shakhashiri).

aniline; (2) purify crude acetanilide product by recrystallization and (3) calculate the percentage yield of pure acetanilide.

Figure 2. Chemical Structure of Acetic Anhydride

MATERIALS AND METHODS Materials

Acetanilide

or

NThe researchers made use of chemical reagents hexane, methanol and water as the choices for selecting the appropriate recrystallization

phenylacetamide, C6H5NH(COCH3), varies from gray to white in color and may be in the form of flakes or powder. It is denser and slightly soluble in water. It is used to accelerate the reactions that produce rubbers as well as a plasticizer to increase the pliability of various plastics. It is soluble in alcohol, ether, chloroform, acetone, glycerol and benzene. It is the product of the acetylation of aniline and acetic anhydride

solvent. Pure acetanilide was also used.Aniline and Acetic anhydride were the chemicals used in the synthesizing of Acetanilide.

Activated charcoal was also used as a decolorizing agent.

Methods
DETERMINATION OF THE

RECRYSTALLIZATION PROCESS

The dried crude acetanilide was poured with 20 mililiters of the recrystallizing solvent. It was heated in a water bath until the entire solid (crude acetanilide) was dissolved. Activated charcoal was then added to decolorize the mixture. While the mixture was hot, it was filtered using a fluted filter paper. After filtration, it was cooled in an ice bath to allow the formation of crystals. The

RECRYSTALLIZING SOLVENT

A corn-grain amount of pure acetanilide was placed into each of the three test tubes. The first test tube was added with one milliliter of distilled water. It was shaken and placed in a warm water bath 37-40 degrees Celsius for one to five minutes. It was then allowed to cool and observations were recorded. The procedure was repeated in the second and third test tubes but using hexane and methanol, respectively.

crystals formed were collected and washed with distilled water.

After the collection and washing of crystals, it were then dried and weighed. Theoretical and percentage

ACETANILIDE PRODUCTION

yield were computed.

Two mililiters of aniline and 20 mililiters of distilled water were mixed in an Erlenmeyer flask. Three mililiters of acetic anhydride was then slowly added to the solution. It was cooled in an ice bath to hasten crystallization. After which, the
Figure 4. Folding of Fluted Filter Paper

solution was filtered using a wet filter paper. The filter paper Using a fluted filter paper increases the surface area inside the funnel, thus speeds up the filtering process.

containing the crude acetanilide was dried and weighed. Observations and results were recorded.

RESULTS AND DISCUSSION Choosing the appropriate

room

temperature

and

lower

temperatures but soluble at elevated temperatures. This fits the criteria for choosing recrystallizing acetanilide water. will the appropriate solvent. Thus, in

recrystallizing solvent is a vital step in the recrystallization process. It aids in the purification of the product. Ideally, the recrystallizing solvent should dissolve the

recrystallize of

Purification

crude

compound of interest at elevated temperatures but insoluble at lower temperatures. In contrast, the

acetanilide will also take place.

Addition

of

activated

impurities should be soluble at room temperature but insoluble during heating (Wigal, C.).

charcoal decolorizes the solution. It adsorbs the impurities because it has a large surface area and it can remove impurities more effectively.

SOLVENT

AT ROOM TEMPERATURE

UPON HEATING Soluble Soluble Insoluble

UPON COOLING Insoluble Soluble Insoluble

However,

too

much

activated

Water Methanol Hexane

Insoluble Soluble Insoluble

charcoal used will not only adsorb the impurities but also the desired product (Pastro, etc., 1998).

Table 1. Solubility of Pure Acetanilide in Different Solvents at Different Temperatures

Table 1 shows the solubility of pure acetanilide in different solvents: water, methanol and hexane, at different temperatures: room The crude and pure acetanilide were weighed.
Weight of Crude 3.0g Acetanilide Weight of Pure 0.8g Figure 5. Synthesis of Acetanilide

temperature, elevated and lower temperatures. In all the temperatures, pure acetanilide is soluble in

methanol while it is insoluble in hexane. Thus, acetanilide will not

recrystallize in these solvents. For water, pure acetanilide is insoluble at

Acetanilide

After process,

the

recrystallization yield were

COMPUTING FOR THEORETICAL YIELD

percentage

computed. To compute for the percentage yield, theoretical and limiting reagent should be known. The limiting reagent is the reactant involved in the reaction that is used up first (Chang, 2008). Theoretical yield is the amount of a product formed when the limiting reactant is completely 2012).
DETERMINATION REAGENT Aniline: OF LIMITING CALCULATION OF PERCENTAGE YIELD

consumed

(Zumdahl,

Thus, the percentage yield of the reaction is 29.63%. This is the pure acetanilide mililiters of obtained aniline from and two three

mililiters of acetic anhydride.

Acetic anhydride: REFERENCES : BOOKS Chang, R. (2008). General Chemistry : The ed.). Essential Concepts (5th New York :

Thus, the limiting reagent is aniline because it will be the first one to be used up.

McGraw-Hill. Pg. 81-85

Pastro, D.J., John, C.R., & Miller, M.S. (1998). Experiment Techniques in and Organic

ONLINE ENCYCLOPEDIA Aniline. In Encyclopdia Britannica

Chemistry. New Jersey: Prentice Hall. Pg. 43-46

online. Retrieved

from

http://global.britannica.com/E checke /topic/25473/aniline

Zumdahl, S. (2012). Chemistry An Atoms First Approach.

Retrieved on

August 3, 2013

United States of America : Brooks/Cole. Pg. 404-405 ONLINE http://www.toolingu.com/definition500150-15780-impurities.html Retrieved July 30, 2013 Cerritos Community College. Purification of Impure Acetanilide (Recrystallization). Organic Chemistry 211 Laboratory. Retrieved from http://web.cerritos.edu/jbrad ury/Sit Pages/Chem.%20211%20lab/2 1%20L b/recrystallization.pdf Retrieved on August 3, 2013 Wigal, C. (2004). Purifying Acetanilide by Recrystallization. Laboratory in Chemistry. from

Modular Program Retrieved

http://www.chm.uri.edu/bdeb ef/ch 292/rextallization.pdf on July

Retrieved 30,2013