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Myeeka Hammond
May 22,2017

Title: Recrystallization

Purpose: The main purpose of this experiment is to practice doing the recrystallization to successfully

purify a solid.

Introduction: In chemistry, recrystallization is a technique used to purify chemicals. By dissolving both

impurities and a compound in an appropriate solvent, either the desired compound or the impurities

can be removed from the solution, leaving the other behind. Choosing the appropriate solvent is the

most critical step in the process of recrystallization since the correct solvent must be selected to form

high purity and a good recovery percentage. When looking for a solvent, one looks for a solvent in which

the major compound dissolves when the solute is hot and recrystallizes once cooled. Some other

characteristics the one can look for are either (1) it dissolves the major component but not the

contaminant and (2) it dissolves the contaminant but not the major compound. This process includes

heating a solution containing the compound and then cooling it, slowly, so that precipitate can form.

Part 1: Preparation and purification of Acetanilide

Material: The materials that were used are (1) 4 ml of aniline, (2) 250 Erlenmeyer flask. (3) 145 ml of

deionized water, (4) 5 ml of acetic anhydride, (6) a few boiling chips, (7) an ice bath, (8) vacuum filtration

system, (9) a thermometer, (10) a Mel-temp apparatus, and (11) a few capillary tubes.

Procedure: After obtaining a 250 mL Erlenmeyer flask 4mL of aniline was added along with 30mL of

deionized water while we swirled the flask vigorously we added 5mL of acetic anhydride slowly and in

small portions. Once we saw some form of crystallization we added 100 mL of deionized water, put the

flash on a hot plate and added a few boiling chips, it boiled until everything was completely dissolved.

Once everything was dissolved we removed the flask from the heat and allowed it to sit until cooled to

room temperature. After reaching room temperature we sat it in an ice bath for about 10 minutes.
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Myeeka Hammond
May 22,2017

While sitting in the ice bath, we set up the vacuum filtration. Once the solution was cooled we poured it

into the funnel and let the liquid and solid separate to obtain crystals od Acetanilide. After completely

drying the precipitate with paper towels, took the melting point by using the Mel-temp apparatus that

we learned to use in the previous lab.

Results and Discussion: To start out with we were given the mass of Aniline which is 93.1 grams per

mole. The first thing that I noticed when I mixed the aniline and the water is that one is polar, the water,

and the other is non-polar, the aniline. The color of the solution once completely boiled it turned to a

yellowish-brownish solution and once it started to cool down the solution turned to a light pinkish color

and crystals started to form. Once in the ice water the solution became mainly precipitate and now it

was more of a white solid rather than the pink solution. Once the procedure was completed, we ended

up with 7.022 grams of acetanilide and could calculate the percentage yield which is 68.84 percent.

Another property that we calculated is the melting point, by using the Mel-temp apparatus, which

resulting in a range of 112-114C after a few attempts. The first couple of tries it would start melting at

80C. We eventually figured out that it was because the crystals were not completely dried so it was

affecting the melting point.

Calculation
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Myeeka Hammond
May 22,2017

Part 2: Isolation and purification of Acetylsalicylic Acid:

Materials: The materials used for this experiment are (1) a short- stemmed funnel, (2) a 125 mL

Erlenmeyer flask, (3) five aspirin tablets, (4) 10 ml of ethanol, (5) a hot plate, (6) hot water bath, (7) extra

10 ml of heated ethanol, (9) vacuum filtration and (10) a Mel-temp apparatus.

Procedure: The procedure for this experiment is similar to the first part but has a few different steps.

The very first thing that was done is weighing five aspirin tablets and then we crushed them and added

them to a 125 ml Erlenmeyer flask along with 10 ml of ethanol and heated the mixture. Also, we heated

about 10 ml of extra ethanol to use as a wash for the filtration. In this part, we filtered the hot solution

using the pure ethanol as a hot rinse and then added water as an anti-solvent, which starts the

crystallization of the acetylsalicylic acid. We then allowed the solution to cool and discarded the

precipitate in the trash. While cooling, we had set up a vacuum filtration to separate the crystals from

the liquid and allow them to dry completely. Once they were dried we took a small sample and found

the melting point range of the compound.

Results and discussion: Now you might be wondering why we crushed the aspirin tablet instead of

leaving them whole. Well, it makes it easier for the tablets to dissolve once adding the ethanol and

heating it. But before we crushed those pills, we did find the mass which is 1.625 grams. Everything

went smoothly in the first half of our experiment, but when we got the part of washing he solution with

only a little of the ethanol we accidentally added a little more than required. Because of this when it

came to the formation of precipitate it took a longer time, and we added a little more than the required

amount of water, since water is what is supposed to form the crystals. At first, we did not think we were

going to get any results but eventually we got something and it turned out to be approximately 1.205

grams of Acetylsalicylic acid. Based on those numbers we were able to calculate the weight of the
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Myeeka Hammond
May 22,2017

impurities, which was 0.42 grams, simply by subtracting. Another calculation that was made is the

percentage of the compound that was recovered, which is 74.15 percent.

Calculation

Overall conclusion: So far, this experiment is my favorite. It entailed a little more than the last and we

got the chance to get familiar with more equipments and techniques. This experiment helps you to

further understand solubility, at least for me it did, and it also teaches you how to figure out the purity

of a substance by simply recrystallizing the compound using two different techniques, the hot and the

cold way. The main thing that my group members and I need improvement on in the lab us learning the

names of all the materials that are in the lab and how to pour liquids in small amounts at a time.

Post Lab Questions:

1) What is the purpose of a boiling stone or chip?

They promote smooth boiling for the solution

2) When doing recrystallization, what observations would prompt you to perform a hot

filtration?

3) What problems might arise if a hot solution is filtered by vacuum filtration?

A rapid decrease or pressure resulting in expansion in gaseous state

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Myeeka Hammond
May 22,2017

4) What is meant when aniline id referred to as the limiting reagent in the reaction with acetic

anhydride?

The moles of aniline is less than the moles of acetic anhydride and the limiting moles of aniline

will react with the moles of acetic anhydride.

5) Under what circumstances would you use mixed solvents in a recrystallization?

When a suitable solvent for the given compound is no there then two miscible solvents that

together provide the appropriate solubility properties are used.

6) Why do we keep the volume of the rinses small in the recrystallization procedure?

So, we have a higher yield, less waste, and a more efficient process overall.