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4-Recrystallization of An Impure Acetanilide Sample

This document describes an experiment on recrystallizing an impure sample of acetanilide. It discusses recrystallization as a method for purification of organic solids using differential solubility. The experiment involves testing the solubility of acetanilide in different solvents to identify the best one for recrystallization. The impure sample is dissolved in hot solvent, filtered, and allowed to crystallize as it cools to purify the acetanilide. Detailed procedures are provided on performing the recrystallization and testing the purity of the purified sample.
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0% found this document useful (0 votes)
285 views8 pages

4-Recrystallization of An Impure Acetanilide Sample

This document describes an experiment on recrystallizing an impure sample of acetanilide. It discusses recrystallization as a method for purification of organic solids using differential solubility. The experiment involves testing the solubility of acetanilide in different solvents to identify the best one for recrystallization. The impure sample is dissolved in hot solvent, filtered, and allowed to crystallize as it cools to purify the acetanilide. Detailed procedures are provided on performing the recrystallization and testing the purity of the purified sample.
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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Experiments in Organic Chemistry

Experiment No. 4

RECRYSTALLIZATION OF AN IMPURE ACETANILIDE SAMPLE

DISCUSSION

Recrystallization is the preferred method for purification of organic solids at room


temperature. The technique can be used for macro, semi-micro or microscale setting,
and it is usually very effective and efficient. The essence of purification by recrystallization
is the deposition of crystals from a solution (crystallization). In the discussions by Brunnelle
et.al., in reference to Figure 1 below:

Figure 4.1. An impure solid in: (A) cold solvent in which it has low solubility, (B)
solvent that has been warmed up to dissolve all of the solid, and (C) solvent that
has cooled down to the original temperature. The crystallized solid is now pure,
while the impurities remain in solution.

If a solid material (impure) is placed in a solvent of low solubility, the solid will dissolve but
the rest will ‘sit there’. However, it doesn’t just ‘sit there’ since equilibrium is in effect. In
order for the entire solid to dissolve, heat must be introduced equal or near to its solvent
boiling point until the entire solid goes into the solution. Then, if the solution is cooled at
some temperature, the concentration of solute will exceed its solubility, and the solid will
start to come back out of a solution- it will crystallize. Now during the process of crystal
formation, a molecule will tend to attached to a growing crystal composed of the same
type of molecules because of a better fit in a crystal lattice of the same structure than for
the other molecules (impurities), which remain soluble into the solution. Finally, by the
time when the initial temperature is reached, all of the original material has formed
crystals, which can be filtered from the solvent.

Evidently, the most significant aspect of recrystallization technique is the selection


of the solvent. Several solvents are commonly used; among these are water, ethanol,
ether, hexane, etc. Ideally, selecting a solvent is based on the desired solubility of the
material to be crystallized. Wherein, the material should be sparingly soluble at room
temperature and yet quite soluble at the boiling point of the solvent selected (Pavia,
1995). The solubility of both the solvent and the solute depends on their polarities and as
it applies “like dissolves like”. In addition a selected recrystallization solvent must me the
following characteristics: (1) it must have high differential solubility; (2) it should dissolve
the impurities at all temperatures; (3) it must remain unreacted with the substance to be
purified; (4) it must be practically volatile and (5) it should be cheap, non-toxic and non-
flammable. With this distinctiveness, printed or online handbooks are needed.

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Experiments in Organic Chemistry

The process does not only begin on selecting a good solvent and end on the
performing recrystallization but it must consider the rate of forming the crystals and the
percentage recovery of the pure solid. To handle this scratching the walls of the
container (It must be an Erlenmeyer flask!) with a glass rod to hasten the rate of crystal
nucleation or the solution can be ‘seeded’ (adding tiny crystals of the substance). If
none of these work consider vaporizing the solution because of too much solvent or work
out for a new solvent. There are other problems such as colored contaminants and
insoluble impurities. This is best remedied by adding activated charcoal and hot filtration.
The filter paper must be fluted and stemless funnel must be used to filter rapidly and
avoid crystallization. The residue and the flask must be washed with hot solvent. The
collected filtrate in the flask begins to form crystals as it reaches room temperature. The
best way to obtain a purer crystal is through slow cooling without agitating the solution.
The flask can be covered by a beaker but not stoppers. Ice-bath cooling is not
encouraged because it causes additional crystallization. The beauty of the crystals
formed in slower phase will compensate your patience rather than the crystals formed in
a speedy process.

Once crystal formation is complete, the product is isolated by vacuum filtration.


This is done with a filtering flask connected to a vacuum source. The Bucher funnel with
carefully laid filter paper completes the set-up. The filtration is followed by washing with
the used solvent and then carefully dried in an air or in an oven.

Here are the summarized steps of recrystallization:


1. Dissolve the crude material in a minimum amount of hot solvent.
2. Treat with decolorizing charcoal.
3. Filter hot solution to remove charcoal and other insoluble impurities.
4. Cool to effect crystallization.
5. Filter crystals, wash to remove adhering mother liquor.
6. Dry crystals to remove last traces of solvent.

In this experiment, five different solvents ranging in polarity will be utilized to determine
the good solvent for the recrystallization of acetanilide. After the proper solvent is chosen
for recrystallization of the impure sample, recovery of the pure acetanilide follows
together with the test for its purity.

TIME ALLOTMENT

• This activity will take three (3) hours to perform.

MATERIALS
NChemicals/Reagents:
pure acetanilide, impure acetanilide, ice, activated charcoal, solvents:
distilled water, ethanol, acetone, toluene,

! Glasswares/Equipment:
hot plate, 5 test tubes (small), testube rack, testube holder, 1 mL pipet for
each solvents, 500 mL beaker, 250 mL, beaker, 100 mL beaker, 125 mL
Erlenmeyer flask (2), stirring rod, filtering funnel, filter papers, basin, Petri dish,
vacuum pump, Buchner funnel, sciccors

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Experiments in Organic Chemistry

PRECAUTIONS
• Always wear your laboratory gown and safety goggles.
• Keep volatile & flammable liquids (e.g. ethanol, acetone) away from flame.
• Acetanilide is harmful if swallowed.
• Cool hot glasswares before washing.
• Do not weigh hot substances.
• Dispose organic wastes into its respective waste bottle.

PROCEDURE

A. Determination of a Good Solvent for Recrystallizing Acetanilide

Perform the succeeding procedure in testing the solubility of acetanilide in


distilled water, ethanol, acetone and toluene. Determine which solvent is most suitable
for recrystallizing acetanilide.

Place approximately 25 mg (about a heap on the tip of a ballpen cap) of


acetanilide into a test tube containing 1 mL of water. Shake the tube and observe. If the
substance fails to dissolve, heat (do not boil) the tube gently under a hot water bath. Do
not heat longer than necessary to undue evaporation of the solvent. If undissolved solid
still remains, add 1 mL more water and warm. Shake the test tube and observe for the
dissolution of pure acetanilide. Test for the solubility of acetanilide in ethanol, acetone
and toluene following the same procedure.

Cool the contents of four test tubes in an ice bath and observe for any
reappearance of the crystals. If crystals do not appear in any of the test tubes, add a pin
head size of acetanilide crystal into the solution or scratch the inside wall of the test tubes
beneath the solvent surface with a stirring rod. Identify the solvent that is best in
recrystallizing an impure acetanilide mixture. Report your finding to your instructor.

B. Recrystallizing Impure Acetanilide

Accurately “weigh about 2 g” of impure acetanilide in a


watch glass using the analytical balance. Place it in a 100 mL beaker
and add 50 mL of the solvent that was observed to be suitable for
recrystallizing the compound. Heat the mixture using the hot plate,
stirring it uniformly until it almost boils. If the solution is colored, add a
pinch of activated charcoal and continue heating to almost boiling.
Check if the suspension is still colored by spotting a drop of the mixture
on filter paper. If the color of the mixture is still evident, add more
activated charcoal if necessary. Meanwhile, prepare to filter the hot
suspension.

Prepare a filtration set-up (see Fig.4.2) by folding a fluted filter


paper and placing it on a funnel. Use a 125-mL Erlenmeyer flask as the
receiver. Pre-heat the set-up just prior to use by pouring hot solvent
Fig.4.2: Filtration Set-up for
into the filter paper. Empty the flask and filter the hot suspension. It is Recrystallization

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Experiments in Organic Chemistry

essential that this operation be completed as quickly as possible in order that cooling is
minimized. It is also advisable to place only few mL of the hot solution into the funnel,
keeping the remainder of the solution in the flask hot by heating on a hot plate until it is
transferred to the funnel. If the filtrate remains to be colored, add a pinch of activated
charcoal, heat and refilter.

Allow the filtrate to cool slowly to room temperature undisturbed. Observe the
appearance of crystals. To induce the crystallization of more acetanilide, chill the flask in
an ice-water bath and scratch the walls of the flask in contact with the solution.

While waiting for most of the acetanilide to recrystallize,


assemble a suction filtration apparatus (if available) as follows: cut a
circular piece of filter paper of such diameter that it exactly covers
the flat surface of the perforated portion of Buchner funnel filter plate.
Determine the weight of this filter paper and place it in the Buchner
funnel. Fit the Buchner funnel to a suction flask. (If not available make
use of gravity filtration set up with a stemless or short stem funnel.)

When the filtration apparatus has been set-up, moisten the


filter paper in the funnel with a few drops of the solvent. Now, filter the
crystals out of the solution by pouring it in the funnel and the solvent
will eventually be drawn inside the flask. Fig 4.3: Vacuum Filtration Set-up

Dry the crystals transfer the crystals together with the filter paper into a Petri dish,
and place in an oven preheated to 105 oC. Keep it in the locker until the next laboratory
period. Weigh the dried crystals and filter paper to the nearest 0.0001 gram. Determine
the percentage of the pure crystals recovered from the impure sample. Determine the
melting point of the purified acetanilide in experiment #7.

REFERENCE

Organic Chemistry Experiments (Unpublished 2004). Department of Chemistry. De La


Salle University. Manila.

Pavia, Donald L. (1995). Introduction to Organic Laboratory Techniques: A Microscale


Approach. Saunders College Publishing. Washington. pp. 601-620.

Pasto, Daniel J. et.al. (1992). Experiments and Techniques in Organic Chemistry. Prentice-
Hall Inc. New Jersey.pp 43 –46 and 391-392.

CRC Handbook of Chemistry & Physics 84th Edition 2003-2004.

Brunnelle, W.H. et.al.October 2, 2004.


www.chem.missouri.edu/Harmata/Chem212/212Exp1V2.pdf

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Experiments in Organic Chemistry

REPORT SHEET
Experiment No. 4

Name Score

Year and Section Group Number


Content Performance Presentation TOTAL

Date Performed Date Submitted Name of Professor

Experiment Title

DATA AND RESULTS

Table 4.1: Solvent Identification for Acetanilide

Solubility @ a Given Temperature Reappearance Good Solvent


Solvent, (bpt, oC)
Room High of Crystals (Yes or No)
Water, 100

Ethanol, 78.5

Acetone, 56.2

Toluene, 110.6

Legend: (+) soluble, (-) insoluble, (±) slightly soluble


Solvent Chosen: __________________________

Table 4.2: Observations on the Recrystallization Process

System Description/Observation
Impure solid sample
Impure solid sample after the addition of
solvent
Dissolved mixture after the addition of
activated charcoal
Filtrate in the receiver

Residue in the Filtering funnel

Solids recovered after recrystallization

Pure acetanilide

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Experiments in Organic Chemistry

Table 4.3 Percent of Pure Acetanilide Recovered

Details Mass (g)


Mass of container
Mass of Impure acetanilide & Container
Mass of Impure Acetanilide
Mass of filter paper
Mass of filter paper and Crystal recovered
Mass of crystals Recovered (Pure)
% of pure crystals Recovered
= mass of crystals recovered x 100
mass of impure acetanilide

Table 4.4: Physical Characterization of Recrystallized Acetanilide*

Observation/Quantity
Color
State
Melting Approximate _______
point (oC) Mpt Range: ________
True value: _________
Density
Structure

*To be completed are the Experiment #7

GUIDE QUESTIONS

Write your answer on the space provided for the following questions.

1. Under what circumstances is it wise to use a mixture of solvents to carry out


crystallization?

2. How are impurities removed in a recrystallization?

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Experiments in Organic Chemistry

3. Compare the melting ranges for the pure and impure acetanilide samples. What
can you tell from these? Describe the requirements for a good Recrystallization
solvent.

4. Compare the melting point of your purified acetanilide with that listed in the
literature. Discuss any discrepancies. Are they significant?

5. Determine the percent recovery of pure acetanilide. Discuss possible losses of


material during the recrystallization operation. Are there places you know that
you lost a significant amount of material? What changes would you recommend
to minimize such losses?

6. The solubility of compound A in ethanol is 0.8 g per 100 mL at 0oC and 5.0 g per
100 mL at 78oC. What is the minimum amount of ethanol needed to recrystallize
12.0 g sample of compound A? How much would be lost in the recrystallization?

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Experiments in Organic Chemistry

CONCLUSIONS & RECOMMENDATIONS

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