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Volume No. 5

Issue No. 2

Volume No. 5 Issue No. 2 Date of Submission: October 30, 2015 Date of Acceptance: October

Date of Submission: October 30, 2015

Date of Acceptance: October 30, 2015

Application of Recrystallization Techniques in the Purification of Acetanilide Using Appropriate Solvent

Macatantan, Sedfrey L. 1 ; Gaviño, Patricia Anne L.; Lat, Dheya O.; Manalo, Jayvee Bien D.; Dr. De Castro- Cruz, Kathlia A. 2 Mapua Institute of Technology, Muralla Street, Intramuros, Manila, Metro Manila, Philippines

ABSTRACT

Solubility of a substance varies with the properties of the solute and solvent present. For solids, most have higher solubility at high temperatures and low solubility at low temperatures. In choosing the most appropriate solvent, the solute should also be considered. The solvent should be the one that is able to exclude impurities. Recrystallization is a method of purifying an impure solid in a solvent which results to an impurity-free product. The experiment aims for us to be able to choose the right solvent for a given compound that can be used for recrystallization; and to perform recrystallization techniques in the purification of solid samples. Each solid has a solvent that would be appropriate for it. Acetanilide is used in recrystallization together with water as a solvent. It is done by boiling, dissolving, filtering, cooling, and vacuum filtering the mixture. The product has been a pure acetanilide which is free from impurities. Keywords – solubility, solvent, temperature, recrystallization, impurities, purification

  • 1 Student, CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; sedfreymac@yahoo.com

  • 2 Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; kadecastro@mapua.edu.ph

1. INTRODUCTION substance will be dissolved in the solution and will be excluded as the solution

1.

INTRODUCTION

substance will be dissolved in the solution and will be excluded as the solution crystallizes which will then result to a pure solid (Petrucci, Harwood, Herring, & Madura, 2007).

To

have

an

effective

process

of

recrystallization, it should be noted that the impure solid and its impurities should not have the same solubility in the solvent that will be used. This now leads to the selection of the appropriate solvent that should be used in the application of recrystallization. In selecting the solvent to be use, the solubilities of the solute and the impurities should be considered. Given this, at a high temperature of the compound, the whole substance should be dissolved, and the opposite should happen at a low temperature (Baluyot & De Castro). This is because at lower temperatures, the heated solution tends to form crystals, and nothing will happen if it would dissolve at still low temperatures.

Solid substances could be soluble in for some solvents and also insoluble for some which is why properties of both the solute and solvent should also be considered for choosing the appropriate solvent. In the experiment, solubilities of different kinds of solid solutes are tested using different solvents – both hot and cold – so that appropriate solvents would be known for certain solutes, which is also a part of the recrystallization techniques.

  • 2. EXPERIMENTAL SECTION

Materials Used. Buchner funnel, Thomas-Hoover melting apparatus, hot plate, stemless funnel, funnel support, micro test tubes, test tube rack, Erlenmeyer flask, beaker, capillary tubes, oven

Purification of substances is the physical separation of the wanted substances from the unwanted ones. It is a vital process especially in dealing with sensitive experiments wherein pure substance is a must-use to have good and accurate results. In using pure substances, there would not be any hindrance or alterations in the process as the substance being used is free from any impurities or any other unwanted parts or substances. On the other hand, the use of impure substances is the opposite of what is with pure substances, as impurities and unwanted substances will be present and they will also come along in the experiments which would probably lead to inaccuracies and interferences in performing the processes and finding the results.

Given that idea, it is important to know some methods which can be used in purification of substances. Some are liquid-liquid extraction – where impurities are removed and wanted products are recovered by dissolving crude materials in a solvent were parts of the feed are soluble; centrifugation – where at high speed, light particles revolve using an electric motor so that the particles which do not settle at the bottom would finally settle down; and adsorption – where impurities that are soluble are removed by trapping them on the surface of a solid material which can now form a strong non-covalent bond with the impurity which then sticks to it (Barbour & Burl, 2015). These are just few of the many more purification methods that there are. Also, the choice of what method of purification to be used varies from experiment to experiment as it depends on the type of substances that one has for a solute and a solvent.

For the experiment, the method that we have used is recrystallization. Here, a solution will be created by having an impure solid compound dissolved in a solvent. Filtration will then be done and as the solution cools down, the compound will now crystallize from the solution. As this happens, the molecules of the unwanted parts of the original

Reagents Used. Acetamide, acetanilide, aspirin, benzene, benzoic acid, crude acetanilide, distilled water, ethanol, ethyl acetate, naphthalene, sucrose

Choosing Appropriate Solvent. 0.10 g of the solute to be used is put on a micro test tube. It will then be dissolved in 2 mL of the solvent. If the solute does

  • 1 Student, CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; ishy.gavino@yahoo.com.ph

  • 2 Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; kadecastro@mapua.edu.ph

not dissolve, then the mixture will be boiled or put into a warm water bath. All

not dissolve, then the mixture will be boiled or put into a warm water bath. All solutes will be used for all solvents. Solubilities in both hot and cold temperature will then be observed.

solvents) while the nonpolar ones are naphthalene and benzene for the solute and solvent, respectively.

Table 1. Solubility of acetamide in different solvents

Recrystallization of Impure Acetanilide. 100 mL of water is heated. From our sample, 3.50 g of crude acetanilide is weighed and it is dissolved in 30 mL of water. The mixture is then boiled on the hot plate. As it boils, 2 mL of the previously heated water will be added while stirring until the white solid from the mixture is completely dissolved. Using the hot gravity filtration set-up, the solution will now be poured into the stemless funnel covered by the fluted filter paper. The filtrate will ran down and it should be colorless. For our part, the residue crystallized immediately so we added more heated water and we simply evaporated the excess water after all of the solution passed through the fluted filter paper. The filtrate is then cooled down and placed in an ice bath while being shook. After crystals are formed, it is then poured into the Buchner funnel and washed with cold water. For a while, the wet crystals are dried and when it is already dry, it is then weighed.

 

Solvent

Acetamide

Cold

Hot

Water

Soluble

Soluble

Ethanol

Soluble

Soluble

Benzene

Insoluble

Soluble

Ethyl Acetate

Insoluble

Soluble

Previously, it is said that an ideal solvent is the one that dissolves the solute completely at high temperature and does not have much effect on the solute at a low temperature. From Table 1, two solvents satisfy this description – benzene and ethyl acetate. Based on the fact that “like dissolves like”, acetamide and ethyl acetate are polar compounds while benzene is a nonpolar compound, this proves that benzene would be the best solvent for acetamide as they are “unlike”, meaning that it would be more impossible for a benzene to dissolve acetamide (already seeing that all the solvents dissolve acetamide at high temperatures).

Table 2. Solubility of acetanilide in different solvents

  • 3. RESULTS AND DISCUSSION

In the experiment, we have determined the solubility of different solutes in different solvents (both hot and cold). Basing on the properties of the substances used, particularly the intermolecular forces, we can at least have an idea of what will happen after trying to dissolve a certain solute in a certain solvent. If we can remember, there is a principle which is “like dissolves like” which pertains to the fact that polar molecules can dissolve polar molecules, and nonpolar molecules dissolve nonpolar molecules (Yoder, 2015). By keeping this in mind, we would be able to study more the solubility of the given solutes in the given solvents. For the substances used, the polar ones are acetamide, acetanilide, aspirin, benzoic acid, sucrose (for the solutes), water, ethanol, and ethyl acetate (for the

 

Solvent

Acetanilide

Cold

Hot

Water

Insoluble

Soluble

Ethanol

Insoluble

Insoluble

Benzene

Insoluble

Soluble

Ethyl Acetate

Soluble

Soluble

Table 2 shows the solubility of acetanilide in different solvents. The solvent that fits the description for the most appropriate solvent to be used is water. It is because it shows that acetanilide would be soluble only at high temperature and insoluble at low temperature, meaning that the acetanilide would require high temperature for it to be dissolved completely and as it does not dissolve at low temperature, it would simply crystallize once it passes through the filter and cooled down, as the impurities would also be filtered easily.

Table 3. Solubility of aspirin in different solvents

  • 1 Student, CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; ishy.gavino@yahoo.com.ph

  • 2 Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; kadecastro@mapua.edu.ph

Solvent Aspirin Cold Hot Water Insoluble Soluble Ethanol Soluble Soluble Benzene Insoluble Soluble Ethyl Acetate Insoluble
Solvent
Aspirin
Cold
Hot
Water
Insoluble
Soluble
Ethanol
Soluble
Soluble
Benzene
Insoluble
Soluble
Ethyl Acetate
Insoluble
Soluble

once the solution is filtered.

Table 5 shows the solubility of naphthalene

in different solvents. It can be said that ethanol is the

most appropriate solvent for naphthalene. It is

because naphthalene only partially dissolves in

ethanol. Therefore, impurities will immediately hang

For the most appropriate solvent for aspirin,

it can be said from Table 3 that benzene is the most appropriate solvent. Three from the four compounds show that they can dissolve aspirin at high

temperature

but

cannot

at

low temperature. The

reason why benzene is the most appropriate is

because

in

water, aspirin

only dissolves

a

little.

Moreover, ethyl

acetate is proved

to polar while

Table 6. Solubility of sucrose in different solvents

 

Solvent

Sucrose

Cold

Hot

Water

Soluble

Soluble

Ethanol

Insoluble

Soluble

Benzene

Insoluble

Soluble

Ethyl Acetate

Insoluble

Soluble

benzene is nonpolar. As the aspirin is polar, it is less

From Table 6, it can be said that ethanol is

likely to be dissolved by benzene, much more in lower temperatures, which makes it a more appropriate choice.

the most appropriate solvent for sucrose. Sucrose is only slightly soluble in ethanol. Much less will be dissolved when sucrose is tested in cold ethanol. This is why after heating, the impurities can be easily

Table

4.

Solubility

of

benzoic

acid

in

different

filtered because it is only partially soluble at high

solvents

temperature and not at all at a low temperature.

 

Solvent

Benzoic Acid

Cold

Hot

Water

Insoluble

Insoluble

Ethanol

Soluble

Soluble

Benzene

Soluble

Soluble

Ethyl Acetate

Soluble

Soluble

Table 4 shows the solubility of benzoic acid in different solvents. As can be seen, water is the most appropriate solvent to be used. It is because benzoic acid is insoluble in both low and high temperatures of water which means the impurities can be easily filtered once the solution is heated and cooled down.

Table

5.

Solubility

of

naphthalene

in

different

solvents

 

Solvent

 

Napthalene

 

Cold

 

Hot

Water

 

Insoluble

 

Insoluble

Ethanol

 

Soluble

 

Soluble

Benzene

 

Soluble

 

Soluble

Ethyl Acetate

 

Soluble

 

Soluble

For the recrystallization part, we know that

recrystallization can be used in separating or

removing impurities of solid substances. The solute

that we have used is 3.50 g crude acetanilide. From

the results listed above, it is known that the best solvent to be used in this type of recrystallization is water for the reason that we would want to get as much crystallized products as we can. Acetanilide is soluble-enough in water and much more on the other compounds. Given that, it is because we would want to use the solvent where the compound will have the least solubility so once it is filtered out, and cooled, then impurities would be clinging up in the residue and the filtrate would just contain the desired crystals when furtherly cooled. Now, during the heating of the

mixture of water and crude acetanilide, some water

would evaporate which is why heated water is

continuously added. This is also to make sure that the

wanted solids in the solution would be dissolved

completely so that it can pass through the filter paper.

Once the solution is filtered, it would then be cooled

to room temperature and not directly on the ice bath,

  • 1 Student, CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; ishy.gavino@yahoo.com.ph

  • 2 Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; kadecastro@mapua.edu.ph

6.
6.

so that the immediate form of crystals would be prevented because it would cause impurities due to the fact that formation of crystal lattice would be unsuccessful because it is performed faster than it should have been. The resulting crystals from the ice bath will then be vacuum filtered so that the solid product which is the crystal would be separated from the liquid ones which are still clinging to the crystals. Now, from the 3.51 g that we started with the crude acetanilide, the weight of pure acetanilide that we got is 1.21 which gives us a percent recovery of 34.57% which is pretty reasonable given the resulting product that we have. Melting point is measured and it is seen to be 113C.

  • 4. CONCLUSION

In the experiment, we have dealt with the determination of the appropriate solvents for given solutes. It can be said that in choosing for the most appropriate solvent, we should also consider the properties of the solutes and solvents as they will also play a part in deciding which to use. “Like dissolves like” principle could help in the determination. Polar substances would dissolve polar substance; nonpolar substances would dissolve nonpolar substances. An appropriate solvent is the one that could exclude all unwanted impurities while still able to retain the wanted parts of the original substance.

Baluyot, J. Y., & De Castro, K. A. (n.d.).

Organic Chemistry Laboratory Manual for Chemical Engineering Students Part 1.

Barbour, P., & Burl, J. (2015, August 31). Recrystallization. Retrieved from Organic Chemistry at CU Border:

http://orgchem.colorado.edu/Tec hnique/Procedures/Crystallizatio n/Crystallization.html Petrucci, Harwood, Herring, & Madura. (2007). General Chemistry:

Principles & Modern Applications, Ninth Edition.

Pearson Education, Inc. Yoder, C. (2015). Chemistry. Retrieved from Wired Chemist:

http://www.wiredchemist.com/c

hemistry/instructional/laborator

y-tutorials/recrystallization

7.

SUPPORTING INFORMATION

For the recrystallization, we should take into account the solvent that would dissolve in high temperature so that none of it would crystallize immediately, and also the one that does not have much effect when the temperature is low. In this case of crude acetanilide, water is used. This is so the solution would require more heat to be dissolved, and would simply crystallize when subjected to low temperature. In terms of practical works, when pouring the dissolve mixture in the filter paper, it should be done very fast so that it would not crystallize immediately when it experience loss of heat.

  • 5. REFERENCES

Table 7. Data on Recrystallization of Impure Acetanilide

Weight of crude acetanilide

  • (g) 3.51

Weight of filter paper + crystals (g)

2.32

Weight of Filter Paper

  • (g) 1.11

Weight of pure acetanilide

  • (g) 1.21

Volume of water used (mL)

90

Melting point of pure acetanilide (°C)

113

% recovery

34.57%

  • 1 Student, CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; ishy.gavino@yahoo.com.ph

  • 2 Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; kadecastro@mapua.edu.ph

Figure 1. Fluted Filter Paper Figure 2. Hot Gravity Filtration Set-up Figure 3. Vacuum Filtration Set-up
Figure 1. Fluted Filter Paper Figure 2. Hot Gravity Filtration Set-up Figure 3. Vacuum Filtration Set-up

Figure 1. Fluted Filter Paper

Figure 1. Fluted Filter Paper Figure 2. Hot Gravity Filtration Set-up Figure 3. Vacuum Filtration Set-up

Figure 2. Hot Gravity Filtration Set-up

Figure 1. Fluted Filter Paper Figure 2. Hot Gravity Filtration Set-up Figure 3. Vacuum Filtration Set-up

Figure 3. Vacuum Filtration Set-up

Figure 1. Fluted Filter Paper Figure 2. Hot Gravity Filtration Set-up Figure 3. Vacuum Filtration Set-up

Figure 4. Product (Pure Acetanilide)

  • 1 Student, CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; ishy.gavino@yahoo.com.ph

  • 2 Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; kadecastro@mapua.edu.ph

Figure 5. Thomas-Hooover Melting Point Apparatus Figure 6. Turnitit Similarity Index Student, CHM142L/B21, School of Chemical

Figure 5. Thomas-Hooover Melting Point Apparatus

Figure 5. Thomas-Hooover Melting Point Apparatus Figure 6. Turnitit Similarity Index Student, CHM142L/B21, School of Chemical

Figure 6. Turnitit Similarity Index

  • 1 Student, CHM142L/B21, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; ishy.gavino@yahoo.com.ph

  • 2 Professor, School of Chemical Engineering, Chemistry and Biotechnology, Mapua Institute of Technology; kadecastro@mapua.edu.ph