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Alysson D.L. Bonsol, Margaret T. Caligayahan, Lauren C. Cancio, Claire Anne E. Caringal, Ayla L. Castillo Group 2 2B Medical Technology Organic Chemistry Laboratory

Recrystallization is a technique of purifying organic solids based on solubility. This experiment was performed to attain the following objectives which are to synthesize acetanilide by the acetylation of aniline and to purify crude acetanilide product by recrystallization. In this experiment, we mixed 2 mL of aniline, 20 mL of distilled water and 3 mL acetic anhydride and put it on an ice bath for the formation of the crude acetanilide. The crude acetanilide weighing 6.1 g was dissolved in a beaker containing the recrystallizing solvent which is, water. Water is used as the recrystallizing solvent because it passed the criteria for choosing the recrystallization solvent. After adding the recrystallization solvent we heated the mixture in a water bath and we waited for the acetanilide to dissolve. The solution was colored so we added activated charcoal for it to absorb the colored impurities present. Once dissolved we placed it quickly in a filter setup while hot. The filtrate collected must be cooled in an ice bath then collect the crystals, let it dry and weigh it. We computed the percentage yield and we attained an answer of 18.03 %.

Recrystallization is a process of dissolving the solid to be crystallized in a hot solvent or solvent mixture and then cooling the solution slowly. The dissolved solid has a decreased solubility at lower temperatures and separates from the solution slowly. A small seed crystal is formed initially, and it then grows layer by layer. It aims to synthesize acetanilide by the acetylation of aniline and to purify crude acetanilide product by recrystallization. Crystallization of a solid is not the same as precipitation of a solid. In crystallization, there is a slow, selective formation of the crystal framework resulting in a pure compound. In precipitation, there is a rapid formation of a solid from a solution that usually produces an amorphous solid containing many trapped impurities within the solid's crystal framework. For this reason, experimental procedures that produce a solid product by precipitation always include a final recrystallization step to give the pure compound. Solubility refers to the degree of substance in which the solute is to be dissolved in solvent. It was the main factor that affects crystallization. Identifying the recrystallizing solvent was very important in crystallization process. The substance to be crystallized must exhibit ideal solubility behavior in the chosen solvent. Purification of substances could take place when both the desired substance and the impurities have similar solubility at its boiling point temperature; and the impurities correspond to only a small portion of the total solid. The desired compound will crystallize in cooling temperature while impurities will not.

The compound or samples used in this experiment are aniline, acetic anhydride and acetanilide.

Figure 1. Structure of Aniline Aniline (C6H5NH2) also known as aminobenzene or benzenamine 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. Its IUPAC name is phenlyamine, has a density of 1.0217 g/ml and a molecular weight of 93.13 g/mol. Aniline is a clear to slightly yellow liquid with a characteristic odor. It does not readily evaporate at room temperature. Aniline is slightly soluble in water, 3.6g/100mL at 20C, and mixes readily with most organic solvents. It is used to make a wide variety of products such as polyurethane foam, agricultural chemicals, synthetic dyes, antioxidants, stabilizers for the rubber industry, herbicides, varnishes and explosives. When exposed to light and air, it slowly changes it color and darkens because of atmospheric oxidation of an impurity usually present in the benzene from which the aniline was prepared. Aniline is acetylated by warming a mixture of aniline and acetic anhydride, forming N-phenylacetamide, which is more commonly known as acetanilide.

EXPERIMENTAL A. Compounds tested

Figure 2. Structure of Acetic anhydride

Acetic Anhydride (C4H6O3) or Acetyl Ether or Acetyl Oxide is a clear, colorless liquid with a very pungent, penetrating, vinegar-like odor that combines with water to form acetic acid. It is soluble in ether, chloroform and benzene. It has a density of 1.082 g/ml and a molecular weight of 102.09 g/mol. Its boiling point is at 140C while its melting point is at 73C. Acetic anhydride is used in the manufacture of cellulose acetate having the application as a base for magnetic tape and in the manufacture of textile fibers. Also, it is heated with salicylic acid to produce acetylsalicylic acid (aspirin). It is also used in the manufacture of pigments, dyes, cellulose and pesticides etc. Most importantly, it plays an important role in the acetylation of aniline to form acetanilide.

2. Preparing the crude acetanilide In an Erlenmeyer flask, 2mL of aniline, 20 mL of distilled water and 3mL of acetic anhydride were mixed. The solution was placed in an ice bath to hasten crystallization, filtered through a wet filter paper, dried and weighed.

Figure 3. Structure of Acetanilide Acetanilide (C6H5NH(COCH3)) which has a IUPAC name of N-Phenylacetamide is the product of acetylation of aniline with acetic anhydride at low temperature. It is an odorless, white flake solid or crystalline powder. Acetanilide is soluble in hot water, alcohol, ether, chloroform, acetone, glycerol, and benzene. It melts at a range of 114-116C and boils at 304C. It can undergo self-ignite at 545C, but is otherwise stable under most conditions. Acetanilide is used as an inhibitor of peroxides and stabilizer for cellulose ester varnishes. It is also used as an intermediate for the synthesis of rubber accelerators, dyes and dye intermediate and camphor. It is used as a precursor in penicillin synthesis and other pharmaceuticals including painkillers and intermediates. Phenylacetamide structure shows analgesic and antipyretic effects; however, acetanilide is not used directly for it may cause methemoglobinemia, the presence of excessive methemoglobin which does not function reversibly as an oxygen carrier in the blood.

Figure 4. Process of Recrystallization

3. Heating the acetanilide

A 20 ml of the recrystallizing solvent was poured into the crude acetanilide. It was heated in a water bath until all the solid dissolves. A colored solution was produced after it was heated so we removed it from the bath and added an activated charcoal to absorb the colored impurities and heat it again.

Figure 5. Addition of activated charcoal 4. Recrystallization After heating, the solution was filtered using a fluted filter paper. We allowed the filtrate to cool by placing the receiver in a water bath. The crystals were collected and washed using distilled water, dried by pressing in-between filter papers, and weighed. It was placed inside the locker until the next meeting. The pure acetanilide was

B. Procedure 1. Choosing the recrystallizing solvent

A corn-grain amount of pure acetanilide and 1 mL of water are placed into each of three test tubes. The test tubes were shook and placed in a warm water bath (37-40C) for 1-5 minutes. Allow it to cool. The observations upon the given criteria were recorded.

weighted and determined.






acetanilide, which is used in the recrystallization process. This reaction has produced both solid and liquid product which is more preferable because we can determine the melting point and it can be recrystallized.
Percentage yield=

x100 x100 18.03%

= =

Figure 6. Filtration setup

The percentage yield of acetanilide was as computed by getting the quotient of the weight of pure acetanilide and weight of crude acetanilide and dividing the result to one hundred. We have computed that the percentage yield was 18.03%. The percentage yield of pure acetanilide was 18.03% which means there was only a minimum amount of acetanilide lost and the experiment was a success. The pure acetanilide that was collected was colored white. REFERENCES From Books University of Santo Tomas. Faculty of Pharmacy. Organic Chemistry Group. (2013). Laboratory Manual in Organic Chemistry. Quezon City: C&E Publishing Inc. From websites ACETANILIDE (N-PHENYLACETAMIDE). (n.d.). Retrieved August 10, 2013 from ANILIDE.htm ACETIC ANHYDRIDE (ACETYL ETHER). (n.d.). Retrieved August 10, 2013, from C%20ANHYDRIDE.htm PURIFYING ACETANILIDE BY RECRYSTALLIZATION. Retrieved August 10, 2013,from 3X.pdf RECRYSTALLIZATION.Retrieved August 10, 2013, from and crystallization.htm

Fiugre 7. Cooling of solution at ice bath RESULTS AND DISCUSSION We have determined that water is the best recrystallizing solvent where the acetanilide is insoluble at room temperature and upon cooling, and soluble during heating among methanol, and hexane. It can be noticed that the structure of water is polar, while acetanilide is non-polar, this explains that the solute will dissolve in boiling solvent but crystallize when the solvent is cooled down.
Water Methanol Hexane At room temp Insoluble Soluble Insoluble During heating Soluble Soluble Insoluble Upon cooling Insoluble Soluble Insoluble

Table 1. Solubility of pure acetanilide in various solvents.

When aniline and acetic anhydride is added together it will produce acetic acid and