KULLIYYAH OF PHARMACY, IIUM

PHMM 1214 ORGANIC CHEMISTRY

PRACTICAL 2&3

PURIFICATION OF CRUDE DRUG (ASPIRIN) THROUGH

RECRYSTALLIZATION TECHNIQUE AND CONFIRMATION OF ITS
PURITY THROUGH MELTING POINT DETERMINATION

LECTURER : ASSOC. PROF. DR. QAMAR UDDIN AHMED

GROUP/ SECTION : GROUP 3/ SECTION 2

DATE OF EXPERIMENT : 24TH APRIL 2018

ISMAIL BIN MAT ZALI 1711497

MUHAMMAD ZULKIFLI BIN RAZAK 1711559

NOOR SYAZANANI BINTI AMRAN 1710844

SITI NURUL FARAH FARHANI BINTI NOWAWI 1719468

NUR AFIQAH BINTI MOHD ZAKI 1710962

TABLE OF CONTENTS

ASPECTS PAGE NO
1.0 Introduction 1-2

2.0 Objectives 2

3.0 Apparatus and Materials 3

4.0 Methodology 3-4

5.0 Results 5

6.0 Discussion 6-9

7.0 Precautions 9

8.0 Conclusion 10

9.0 Islamization 11

10.0 References 12
ACKNOWLEDGEMENT

The completion of this lab practical and its report could not been possible without the

participation and also assistance from the lecturers and lab assistants. Therefore, we sincerely

thank Assoc. Prof. Dr. Qamar Uddin Ahmed and Asst. Prof. Dr. Zalikha Binti Ibrahim for the

guidance throughout this experiment. We also appreciate the help of the lab assistants for preparing

materials and apparatus of the experiment. Lastly, this practical and its report cannot be completed

within limited time frame without the effort and cooperation from the group members.
1.0 INTRODUCTION

A pure compound is a substance that contain only of molecules same structure or in other

word it can be called homogenous sample. However, it is believed that the substances which only

consist of small amount of contaminants can be regarded as pure sample. This includes the

formation of side products during reaction, unreacted starting materials, inorganic materials, and

solvents. In chemistry, recrystallization is a purification technique and the principle based on the

amount of solute that can be dissolved by a solvent increases with temperature. The substance is

dissolved in a minimum amount of hot solvent or the solution need to be heated near to the boiling

point. At this high temperature, the solute has a greatly increased solubility in the solvent, so a

much smaller quantity of hot solvent is needed than when the solvent is at room temperature. In

fact, the process of recrystallization only works when suitable solvent is used. The solute must be

relatively insoluble in the solvent at room temperature but much more soluble in the solvent at

higher temperature. At the same time, impurities that are present must either be soluble in the

solvent at room temperature or insoluble in the solvent at a high temperature. So, insoluble

impurities can be filtered away while the solution is hot and soluble impurities stay in the solvent

and do not crystallize because there is not enough to saturate the solution. The pure compound can

be collected after being cooled by the cooled solvent. The slower the rate of cooling, the bigger

the crystal formed.

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 In this experiment, melting point is determined by using the crystal. Melting point is where

the temperature at which solid changes to the liquid. The physical properties usually are used to

determine the purity of a substance, identify a compound and characterization of a compound. As

heat is applied to a solid, its temperature will increase until the melting point is reached. More heat

then will convert the solid into a liquid with no temperature change. When the entire solid has

melted, additional heat will raise the temperature of the liquid. Furthermore, the compound used

to be determined its melting point is Aspirin. Aspirin is the prototypical analgesic used in the

treatment of mild to moderate pain. The molecular formula is C9H8O4. It can be dissolved in the

solvent such as ethanol in order to form a crystal.

Aspirin

2.0 OBJECTIVES

1. To learn the technique of recrystallization

2. To determine the melting points of aspirin and other medicinal compounds

3. To find the melting points of various organic compounds and

4. To use melting point to identify the compound

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3.0 APPARATUS AND MATERIALS

Apparatus:

Melting point apparatus Mortar and pestle Glass funnel

Capillary tubes Conical flask Dropper

Filter papers Measuring cylinder Buchner flask and funnel

Chemicals:

Aspirin sample Paracetamol

Aspirin tablets Ethanol 95 %

4.0 METHODOLOGY

Part 1: Recrystallization of Commercial Aspirin

1. Three weighed tablets of aspirin with a few drops of 95% ethanol were dissolved in a conical

flask, and then the alcohol was warmed in a water bath to affect the dissolution.

2. The solution was filtered using filter paper to remove undissolved material remained.

3. A small quantity of cold water was dropped wisely to the clear alcohol solution.

4. The flask was set aside and observed carefully.

5. The flask was cool when crystals start to form by surrounding it with ice.

6. The crystals were collected by vacuum filtration using Buchner funnel

7. The crystals were allowed to dry.

8. The melting point of aspirin was recorded.

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Part 2: Determination of Melting Point

1. A capillary melting point tube and aspirin samples were obtained.

2. A small amount of the aspirin sample was placed on the clean surface. The open end of the

tube was pushed into the aspirin sample. Some of the sample will be in the top of the tube

when inverted.

3. The closed end of the capillary tube was held over the dropping tube. The dropping tube

should be perpendicular to the table and the couple of inches above the table surface. The

capillary tube was dropped into the dropping tube. The capillary tube will be bounced on the

table packing the powder into the bottom between 4-6mm.

4. The capillary melting point tube was placed in the melting point apparatus chamber. A

setting of minimum and maximum was started; the temperature was slowly rise. The sample

was observed continuously, so that the melting point of the sample was not missed. Heat

slowly to acquire the most accurate results.

5. The melting point were recorded, which began when the sample was start melted and ended

when the sample was completely melted.

6. Step 1 until step 5 were repeated by replacing aspirin with paracetamol sample.

7. Aspirin sample from part 1 was obtained and the melting range was determined. The sample

was identified by comparing the data of the samples in part 2 had obtained.

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5.0 RESULT AND CALCULATION

Part 1:

 Weight of three tablets of aspirin = 1.0956g

 Weight of filter paper = 0.343g

 Weight of filter paper and recrystallized aspirin = 0.4677g

 Weight of recrystallized aspirin

= Weight of filter paper and crystallize aspirin – weight of filter paper

= 0.1565g

Compound Melting point (°C) Range of melting

Start End point

Recrystallized 138 147 9

Aspirin

Part 2:

Compound Melting point (°C) Range of melting

Start End point

Aspirin 136 145 9

Paracetamol 171 178 7

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6.0 DISCUSSION

PART A

Three tablets of aspirin was dissolved in a few drop of 95% ethanol. 95% ethanol was used

because aspirin was insoluble in water. Aspirin or acetyl salicylic acid has a bulky benzene ring

(hydrophobic), a benzoic acid group (hydrophilic) and a methylester group which is polar.

Figure 1: Chemical structure of aspirin (acetyl salicylic acid)

Water can only dissolve the carboxylic acid and polar portion of aspirin that is methylester,

however the methylester may not be adequately dissolved. In ethanol, the alcohol group can form

hydrogen binds with carboxylic acid and dipole interactions with ester group. The ethyl side chain

of ethanol, which is a hydrocarbon side chain can form Wan der Waals forces with hydrophobic

benzene of acetyl salicylic acid. In hot ethanol, aspirin will be more soluble whereas in cold

ethanol, aspirin will form crystal.

An aspirin tablet may contains impurities such as starch that act as binder and sometimes

other ingredients like caffeine and buffers. During recrystallization, the impurities will remain in

the solvent and pure aspirin will be obtained through recrystallization. Recrystallization

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technique relies on the fact that solubility increases as temperature increases. An impure (crude)

aspirin is dissolved in hot ethanol. As this solution is cooled, the pure product crystallizes out

and the impurities stay dissolved in the solvent. The pure crystal is collected by vacuum

filtration. Based on the result, the weight of recrystallized aspirin is 0.1565g. Three tablets of

aspirin that weight of 1.0956g were used initially in this experiment. Some of the recrystallized

aspirin may lost during filtration as it stays on the filter paper. Besides, the impurities such as

binder may contribute to the lost of weight of aspirin as it dissolved in the ethanol.

Melting point is a property of a solid at which temperature it turns to a liquid. It is

reported in the lab as a melting point range. Melting point can be used determine the purity of

substance and also to identify of an unknown substance by comparing the melting point with

known melting point. The melting point of the recrystallizes aspirin obtained by using melting

point apparatus is in range of 138 °C to 147 °C. The theoretical value of melting point of aspirin

is 135°C. The result obtained is slightly deviated from the theoretical value in terms of, the value

is higher than the theoretical value and it has broader melting range which is 9. If the sample

obtained has sharp melting point which has narrow melting point between 0.5°C to 1°C, it can be

concluded that the recrystallized aspirin obtained is pure. The deviation may due to some reasons

such as the apparatus was not calibrated properly, there is still solvent trapped in the crystal and

also still contains impurities that has higher melting point.

PART 2

Melting points obtained for the given aspirin and paracetamol are 136°C to 145°C and

171°C to 178°C respectively. Besides for aspirin and paracetamol, they both have broader melting

point range which are 9 and 7 respectively. From the results, it can be deduced that the given

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samples of aspirin and paracetamol contain impurities that has higher melting point. The

theoretical value of melting point for paracetamol is 169.1°C.

QUESTIONS

1. Define the ‘melting point’ of a substance.

A melting point of a substance is a point at which the sample or substance start

converting from solid to liquid. It is used to determine the pure compound and identify

the compound.

2. What is the purpose of determining melting point?

The melting point have to be determined in order for the substance to be recognized. The

experimental value of melting point will be compared with the theoretical value and this is

how the unknown will be identified. As an example, unknown substance has a melting

point of 156⁰C and the value is same as Citric acid so it can be concluded that the unknown

substance is Citric acid. Melting point determination also can be used to measure the purity

of the intended compound.

3. Why is this method not to be used for finding the melting points of inorganic compounds?

It is because inorganic compounds have extremely high melting points thus it is not suitable

to determine the melting point by using this method.

4. Why would the rate of heating influence the melting point?

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 If the rate of heating was too high, the substance may melt before the thermometer has the

chance to register the actual temperature. The melting point will appear to be lower that

the actual value.

7.0 PRECAUTIONS

In order to avoid the errors from occurring, there are some precaution steps that need to be

taken when conducting the experiment. Firstly, the ethanol used as the solvent should be handled

carefully as it is highly inflammable. Therefore, the process of warming the ethanol should be done

with a water bath and not with an open flame. Besides, when the sample is loaded into the capillary

tube, the sample should be packed in the bottom of the tube. This step is necessary to avoid any

air gaps between the solid particles, which can disturb the melting point of the sample. Apart from

that, the sample also should be loaded into the capillary tube sufficiently. This is because, if the

capillary tube is overfilled with the sample, the sample will require more heat to melt, resulting in

wider melting point range.

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8.0 CONCLUSION

In conclusion, the main purpose of the experiment was to correctly identify the melting

points of various organic compounds in order for the unknown to be identified. One of the

organic compounds is commercial aspirin that have been through a process of crystallization. In

this experiment, students will be able to learn the technique of crystallization. Recrystallization

process aims to remove impurities in order to gain a completely pure compound. The melting

point of a substance will be inaccurate if there are impurities such as excipient in the compound.

By knowing the melting point of the unknown compounds, the identity of it can be determined

by comparing the experimental melting point with the theoretical one. The known compounds

used in the experiment are paracetamol and aspirin. In brief, the objectives are fulfilled including

determination of melting points of recrystallized aspirin, given aspirin and paracetamol. The

melting point of recrystallized aspirin, given aspirin and paracetamol are in range of 138 °C to

147 °C, 136°C to 145°C and 171°C to 178°C respectively.

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9.0 ISLAMIZATION

Recrystallization process aims to remove impurities from the compound. This concept can

be applied into daily life especially our intention. In order to obtain the result that is desired, the

intention must be free from anything negative such as arrogance and greed. There has been a hadith

regarding intention that is narrated by Amir al-Mu’minin, Umar bin al-Khattab that said: I heard

the Messenger of Allah (peace be upon him), say:

"Actions are according to intentions, and everyone will get what was intended. Whoever

migrates with an intention for Allah and His messenger, the migration will be for the sake of

Allah and his Messenger. And whoever migrates for worldly gain or to marry a woman, then his

migration will be for the sake of whatever he migrated for."

Hadith from Bukhari & Muslim

In order to get accurate result in the experiment, the compound used must be free from

impurities so that there will be no error. In life, doing good deed with impure intention is an action

that Allah despised. Allah will only reward those that do good deed without expecting worldly

benefits such as richness since this is the concept of ikhlas in Islam.

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10.0 REFERENCES

Britannica, T. E. (2016, March 28). Melting point. Retrieved May 1, 2018, from

https://www.britannica.com/science/melting-point

Libretexts. (2016, July 21). Recrystallization. Retrieved May 1, 2018, from

https://chem.libretexts.org/Core/Physical_and_Theoretical_Chemistry/Physical_Properties_

of_Matter/Solutions_and_Mixtures/Case_Studies/RECRYSTALLIZATION

Bhanot, D. (2014). What Essential Precautions Should Be Taken in Melting Point Determination?

Retrieved April, 30, 2018, from http://lab-training.com/2014/07/18/melting-point-

determination/

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