RECRYSTALLIZATION OF PURE ACETANILIDE

Pineda, Crissa Quiambao, Diane Quilinguen, Pamela Joy A. * Reyes, Kevin Bryan G. Reyes, Klevin Roger L.

Abstract
Recrystallization is a process in which a certain substance is purified through the difference of its solubility at certain temperatures. Aniline was mixed with acetic anhydride in order to produce acetanilide. This was then dissolved with a solvent in water bath. The solution was placed after in an ice bath to cool thus crystals are formed. Molecules of other compounds dissolved in the solution, as acetanilide crystallizes.

Introduction Organic compounds are usually purified through crystallization especially if they are solid at room temperature. Crystallization is the formation of solid crystals precipitating from a melt, solution, or even deposited directly from gas. It is essentially a solid-liquid separation technique. History tells us that crystallization is one of the pristine unit processes. It may be assumed that our ancestors used sodium chloride found in crevices of the surface rocks after drying caused by the sun: this process is still in use in modern solar ponds. Aside from its application as a purification method, crystallization is also used for crystal production. Some of these production methods are Ionic crystal production, covalent crystal production, thin film production, and Silicon crystal wafer production. 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. Because it is a precursor to many industrial chemicals, its main function is in the production of precursors to polyurethane. Like most volatile amines, it possesses the unpleasant odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds. Aniline is colorless, but it slowly oxidizes in air, giving a red-brown tint to aged samples. Acetic anhydride is the chemical compound with the formula (CH3CO)2O, abbreviated Ac2O, it is the simplest isolatable acid anhydride. Widely used as a reagent for organic synthesis, it is colorless and smells strongly of acetic acid, formed by its reaction with the moisture in the air. Acetanilide is an odorless solid chemical that resembles a flake-like appearance. It is also known as Nphenylacetamide, acetanil, oracetanilid, and was formerly known by the trade name Antifibrin. The goal of the experiment is to compute for the percent yield of the pure acetanilide by synthesizing first acetanilide from acetylation of aniline with acetic anhydride and to purify acetanilide from crude acetanilide by the process of recrystallization.

Methodology The different requirements for the experiment were test tubes, tripod, wire gauze, beakers, Bunsen burner, filter paper, aniline sample, hexane sample, acetic anhydride sample, and methanol sample. The group was to perform a recrystallization experiment of acetanilide. The group first did a solubility test of each solvent in order to know which the best solvent for the sample is. A corn grain amount of pure acetanilide was placed in three test tubes, each containing water, hexane, and methanol. Each test tube was to be observed before, during, and after shaking. They were then placed in a warm water bath of 40C for 1-5 minutes. All three test tubes were then allowed to cool. In a beaker, 2 ml of aniline sample was mixed with 20 ml distilled water; after which 3 ml of acetic anhydride was added. Allow to cool in an ice bath in order to hasten the crystallization process.
Figure 3. Filtration of pure acetanilide Figure 2. Heating mixture in hot water bath

When dissolved, immediately perform filtration through a fluted filter paper while the solution is still warm.

Allow filtrate to cool by placing the container in running water. Collect then let all the crystals settle. Finally, weigh and determine the melting point of the pure acetanilide. Results The group was able to determine the correct recrystallizing agent based on the the diagram below.

Figure 1. Cooling of solvent in ice bath

Afterwards, filter it through a damped filter paper. Dry and weigh the crude acetanilide. Then, 20 ml of the recrystallizing solvent was poured into the crude acetanilide. Heat this in a hot water bath until no solid particles are seen.

Before Heating Water Hexane Methanol insoluble insoluble soluble

During Heating soluble

After Heating Soluble

pure acetanilide. It was then weighed in an analytical balance, which yielded 0.3253g. In order for the percent yield to be computed, the following data were needed: Actual yield = 0.3253 g Theoretical yield = 2.96 g % yield = 0.3253 g x 100 = 10.99% 2.96 g Therefore, percent yield of 10.99% was obtained from 3 ml acetic anhydride and 2 ml aniline. The melting point was determined by putting crystals in a capillary tube then submerging it in an oil bath with a thermometer. The temperature obtained ranged from 113-123C. References 1. Geankoplis, C.J. (2003) "Transport Processes and Separation Process Principles". 4th Ed. Prentice-Hall Inc. 2.http://en.wikipedia.org/wiki/Crystallization# Crystal_size_distribution 3. http://en.wikipedia.org/wiki/Acetanilide 4. http://en.wikipedia.org/wiki/Aniline 5.http://en.wikipedia.org/wiki/Acetic_anhydri de

insoluble Insoluble soluble soluble

Table 1. Results of the test for the solvent As seen in the table, there were three different solvents tested; water, hexane, and methanol. Acetanilide in water was insoluble before heating, soluble during heating and soluble also after heating. Thus, water is the most ideal solvent for recrystallization to occur since it yielded the desired behavior needed of the pure acetanilide. Hexane was insoluble all throughout the test, thus recrystallization would not even occur. While Methanol was soluble throughout, thus acetanilide placed in this solvent cannot undergo recrystallization as well. Water is suitable for melting points of organic compounds starting from room temperature up to 70C in a hot water bath. Discussion Acetanilide exhibited exothermic reaction, most especially during cooling in ice bath. Ice bath method also increased the recrystallization process since it allowed the particles to decreased its solubility by releasing its heat from the system. Determination of the percent yield required the theoretical yield and actual yield. Since the theoretical yield was already given, which is 2.96 grams, a procedure was done in order to obtain the actual yield. This was done right after cooling the solution. Afterwards, 20 ml was added then put to a water bath. After induction and filtration, crystals were finally obtained. These are the