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CHM145L Organic Chemistry 1 Laboratory 1 s t Quarter, S.Y. 2015-2016

CHM145L Organic Chemistry 1 Laboratory 1 st Quarter, S.Y. 2015-2016

Simple and Steam Distillation

Castro, Ethan Zachary G., Pasia, Abraham Paul L., Pulido, Froileth S. 1

1 Professor Oliver Villaflores, School of Chemical Engineering, Chemistry, Biological Engineering and Materials

Science Engineering, Mapúa Institute of Technology; 2 Castro, Ethan Zachary G., Pasia, Abraham Paul L., Pulido, Froileth S., CHM145L-C11, School of Chemical Engineering, Chemistry, Biological Engineering and Materials Science Engineering, Mapúa Institute of Technology

ABSTRACT

One unique physical property that may distinguish the identities of substances, most especially liquids, is their boiling point, or the temperature where the vapor pressure they exert equals the pressure of the surroundings or the atmosphere. This characteristic of liquids also dictates another property called volatility, which is defined as the tendency of a liquid to evaporate quickly. Due to the vast combinations of intermolecular forces present in different liquid substances, and other factors as well, almost every substance has its own distinct boiling point, different from another, although there are theoretical situations where boiling points of various substances are equal (such as in vacuum, where there is no pressure). However, in real life, most liquids have their own boiling points: thus, they have varying volatilities as well. The difference in volatility of substances is what makes the process of separation and purification, called distillation, possible. In the first part of the experiment, simple distillation of impure toluene was demonstrated, by taking advantage of the difference in volatility of toluene and the impurity present. Toluene, which is more volatile, is converted to vapor as heat is provided to the distillation system via a hot plate. As the vapor form of toluene passes through the condenser, the difference in temperature between the vapor and the fresh water that is constantly flowing in that part of the set-up allows the toluene to condense back to its liquid form, thereby separating it from the impurity. The pure toluene was then collected in a graduated cylinder to measure the amount of toluene being distilled in a certain level of temperature. The toluene, as observed, began to boil at around 38°C and began condensing when the temperature was approximately 101°C. Of 15 milliliters of the impure sample, 12.5 milliliters of toluene were recovered. Moreover, the second part of the experiment dealt with steam distillation, which is utilized when the substance to be distilled is not exerting enough vapor pressure at high temperatures, such as para-dichlorobenzene, the substance analyzed in the experiment. Additional vapor pressure is added by the steam to the distillation system via steam generator, allowing the p- dichlorobenzene to boil even without reaching its boiling point yet. The distillate were collected in a flask and then cooled in a cold-water bath. After cooling, the mixture was filtered, immediately dried and weighed.

Keywords: boiling point, volatility, distillation

INTRODUCTION

Volatility can be defined as the tendency of a compound to vaporize. In a specific temperature, a compound that has a higher vapor pressure will vaporize more readily than a substance with a lower vapor pressure. To put it in other words, at a certain temperature, the more volatile the compound is, the higher will be

the pressure of the vapor in dynamic equilibrium with its vaporizing substance.

Vapor pressure can be described as the pressure at which the gaseous phase is in equilibrium with its liquid or solid phase. It can be a measure of the tendency of molecules and atoms to escape from a liquid or solid. In atmospheric pressures, an instance when the

CHM145L Organic Chemistry 1 Laboratory 1 s t Quarter, S.Y. 2015-2016

CHM145L Organic Chemistry 1 Laboratory 1 st Quarter, S.Y. 2015-2016

vapor pressure of a liquid increases with the temperature increases to the point at which it equals the atmospheric pressure, the liquid has attained the temperature at which the liquid changes its state from a liquid to a gas throughout its bulk, this can be referred as boiling point. It is commonly called as the liquid’s normal boiling point.

The normal boiling point of a liquid will be at a lower temperature the greater is the susceptibility of its molecules to escape from the liquid, specifically, the higher the vapor pressure. In other words, the higher the vapor pressure of a liquid, the higher is the volatility and the lower is the normal boiling point of the liquid, therefore, a direct relationship can be deduced between the vapor pressure and the volatility.

be deduced between the vapor pressure and the volatility. Figure 1. A common vapor pressure chart

Figure 1. A common vapor pressure chart for several liquids

Different compounds will exert different vapor pressures at a given temperature because of variations in the intermolecular forces of attraction working in these different compounds. In terms of intermolecular forces, the boiling point acts as the temperature at which the liquid molecules hold enough kinetic energy to surmount the several intermolecular attractions binding molecules to each other within the liquid. Hence, the boiling point is also an indicator of the strength of those intermolecular attractive forces. The stronger the intermolecular attractive forces are, the more difficult it is for molecules to escape from the liquid and therefore, a lower vapor pressure of the liquid. Through this, an indirect relationship can be established, for instance, the lower the liquid’s vapor pressure, the higher the temperature must be to initiate boiling and then, resulting to a direct relationship between intermolecular attractive forces and the normal boiling point.

Through the aforementioned discussed concepts, it is therefore possible to separate compounds from each other in a mixture based on volatility differences. More volatile compounds have higher possibility to be converted into vapor earlier than with low volatilities, this process is known as distillation. Distillation is a widely used method for separating mixtures based on the differences in the conditions (boiling point, volatility, etc.) required to change the phase of the components of the solution. To perform this process, the liquid must be heated to transform the components into vapor (Again, this process is feasible since compounds with higher volatilities vaporize earlier.) then, the vapor will be condensed back into liquid form and collected in a receiving container. Usually, distillation can help the researchers to determine the boiling point and to purify compounds (repeating the describe process can make the compound purer).

CHM145L Organic Chemistry 1 Laboratory 1 s t Quarter, S.Y. 2015-2016

CHM145L Organic Chemistry 1 Laboratory 1 st Quarter, S.Y. 2015-2016

In this experiment, two types of distillation were performed, simple and steam distillation.

Simple distillation is a procedure in which a volatile compound is separated to a nonvolatile compound or separating compounds with different boiling points through application of heat. This can be used to virtually separate liquids that have at least fifty degrees difference in their boiling point, or to separate highly volatile compound from a lowly volatile compound. As the liquid being distilled is heated, the vapors that form are the richest in the component that boils at the lower temperature and highly volatile. As the process progresses, the vapors of the volatile compound goes to the distilling flask through a sidearm and then reaches the condenser, which should be surrounded by fresh water at all times. The difference between the temperature of the fresh water and the vapor in the condenser forces the vapor to change back into liquid form which is then collected in another flask. It is also important to take note of the following in order for simple distillation to be successful:

1. The substances to be separated must have a large volatility difference. Often, this translates to a boiling point difference of around 80°C to 100°C. Otherwise, both compounds may be distilled off and will not be separated from each other.

2. Gently supply the heat to the distilling flask.

3. The thermometer bulb used to measure the boiling of the distilling liquid must be at the level of the sidearm.

4. The distilling flask must be in an upright position at all times.

5. Glass beads or ceramic material must always be present inside the distilling flask prior to heating of the mixture.

6. Fresh cooled water must always fill the condenser, therefore, running water should be applied to the condenser.

therefore, running water should be applied to the condenser. Figure 2. A typical simple distillation set-up

Figure 2. A typical simple distillation set-up

When a solution or mixture of two nearly immiscible liquids is heated while being discomposed to display the surface of one liquid to the vapor phase, each of the component independently wields its own vapor pressure as a function of temperature as if the other component were not present. Resulting to the increase of the vapor pressure of the whole system. Take note that boiling starts when the sum of the vapor pressures of the two immiscible liquids just predominates the atmospheric pressure. In such way, several organic compounds insoluble in water may be purified at a specific temperature well below the point at which decomposition occurs. Typically, water is introduced into the distillation apparatus to provide additional vapor pressure to help a nonvolatile organic compound to boil off and be distilled at a temperature much lower than its normal boiling point. The water vapor bears the small amounts of the vaporized compound to the condensation flask, where the

CHM145L Organic Chemistry 1 Laboratory 1 s t Quarter, S.Y. 2015-2016

CHM145L Organic Chemistry 1 Laboratory 1 st Quarter, S.Y. 2015-2016

separation of the condensed liquids phase happens, allowing then for easy collection. This concept effectively allows for distillation at lower temperatures, reducing the decomposition or deterioration of the desired products. After distillation, the vapors, again, are condensed suitably. Usually, the immediate product is a two- phase system of water and the organic distillated, this can be separated by decantation, partitioning or other appropriate methods. In this experiment, the water in the distillate is separated through a separatory funnel.

The steam distillation apparatus are constituted of three main parts:

Steam Generator

This part supplies sufficient steam to add to the vapor pressure of the organic compound.

Sample Flask

This flask contains the compound to be distilled with water, and heat sources for both the steam generator and the sample flask.

Collecting Flask

Guides the collection of distillate.

It is also important to take not of the following to successfully perform steam distillation:

1. Boiling chips must be present both in the steam generator and the sample flask before heating is started.

2. Gently apply heat to the steam generator and the sample flask.

3. The condenser must always be filled with fresh water during the entire process.

4. No reactions should happen between the compound being steam distilled and with water.

between the compound being steam distilled and with water. Figure 3. A typical steam distillation set-up

Figure 3. A typical steam distillation set-up

METHODOLOGY

The experiment are divided into two parts, the first part is the simple distillation and the second part is the steam distillation.

In the first part of the experiment, the researchers must assemble the set-up shown in the figure in their laboratory manual (Figure 3.1, page 19). Transfer 15 milliliters of impure carbon tetrachloride into the pear-shaped flask using a pipette (the flask should contain only 1/3 of its total volume). Then, turn on the hot plate and switch on the heat regulator to number 6. As it progresses, collect the distillate at different temperatures at the rate of 1 drop per second. Measure, then, the volume of the distillate obtained at different temperatures. Continue the distillation until about 1 to 2 milliliters of distillate is left in the flask. After this, plot the temperature against the volume of distillate collected. Also, record the temperature at which most of the liquid distills as the boiling point.

Obtain a 2 grams-sample of impure p- dichlorobenzene from the instructor and determine the melting point range of the mixture. Assemble the set-up like in Figure 3.2, page 19 of the laboratory manual, the researchers should make sure that there is no leak in the set-up.

CHM145L Organic Chemistry 1 Laboratory 1 s t Quarter, S.Y. 2015-2016

CHM145L Organic Chemistry 1 Laboratory 1 st Quarter, S.Y. 2015-2016

Boil slightly a hundred milliliters of water in the Erlenmeyer flask before connecting it to the set-up, this will serve as the steam generator. As the researchers heat the water, put the sample inside the pear-shaped with arm flask and partly dissolve it in 5 milliliters of water by gently applying heat in the mixture. After which, connect all the apparatus and heat the steam generator before proceeding with the distillation. Continue the process until all the p- dichlorobenzene has distilled, this should take about 10 to 15 minutes. Before disconnecting the apparatus, cool the mixture in the receiving tube. Then, filter the p-dichlorobenzene with suction and air dry the compound, the researchers should not allow it to stand in the open for a longer period since it will evaporate. Weigh the dried material, obtain its melting point and compute the percentage recovery.

RESULTS AND DISCUSSION

For the first part of the experiment in which simple distillation was used, the impure toluene was purified. After boiling the substance in the distilland for about 10-15 minutes, the first drop was collected at the temperature of 102°C and the distillation stopped at the temperature of 123°C. The boiling point range of toluene was therefore concluded to be 102-123 °C. The graph below illustrates the temperature plotted against the volume of the distillate. At the end, 83.33 percent of the 15 milliliters of toluene was recovered. Also, the recovered substance is clear. Theoretically, simple distillation, is only successful when the difference between the boiling points of the components of the mixture is very large but compared to other types of distillation, it has a simpler set up and it consumes less energy. In simple distillation, the more volatile component of the mixture, which is toluene, is being removed by turning it to vapors

and condensing it into another flask. It was observed that as the temperature rises the volume of the liquid in the receiving flask is also increasing. On the other hand, the less volatile component of the mixture is left in the distilland. Through slow distillation via controlled heating, both the components can be separated by changing the receiving flask. This explains the significance of the addition of glass beads. The borosilicate glass beads provide surface area for the condensation-evaporation process, this prevents bumping or the rapid boiling which could ruin the setup. Heating rate is also controlled to prevent superheating which also results into bumping.

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Figure 4. Plot of temperature against the volume of the distillate

In the second part of the experiment, para-dichlorobenzene was purified using steam distillation. Simple distillation is not applied in purifying this compound because boiling it will only cause the compound to decompose so, steam distillation is executed instead. Steam distillation is used in purifying temperature- sensitive material such as para-dichlorobenzene

CHM145L Organic Chemistry 1 Laboratory 1 s t Quarter, S.Y. 2015-2016

CHM145L Organic Chemistry 1 Laboratory 1 st Quarter, S.Y. 2015-2016

which is a hydrocarbon aromatic compound. Steam is added to the distillation apparatus to lower the boiling point of para-dichlorobenzene and prevents its decomposition. A hundred milliliter water was boiled which will act as a steam generator while heating the slightly dissolved test compound. Cloudiness was observed as the test compound was transferred to the pear-shaped flask. Before the distillation started, a safety tube was connected to the cork of the steam generator to allow the water to escape when the pressure is too high. The distillation lasted until all the p-dichlorobenzene has been distilled. The liquid in the receiving flask was cooled, filtered and air dried. At the end, 95.2 percent of the 2.00 grams of para- dichlorobenzene was extracted.

CONCLUSION AND RECOMMENDATIONS

The researchers were able to apply the technique of distillation in both simple and steam distillation. In the former, it is known that in order to be able to accomplish a successful experiment, the substances in question must have large differences in volatility. Without this in consideration, both constituents may be distilled off together and result in an unsuccessful experiment. In the latter, steam distillation is often used when the vapor pressure of a dissolved organic compound still remains low even at high temperature levels. Steam distillation is effective due to its means of addition of vapor pressure through a steam generator. This addition of vapor pressure results in the mixture attaining atmospheric pressure at lower temperatures. This is significantly important because, sometimes, organic compounds will decompose faster than it will take for it to boil. A decomposition of the desired product will result in a very fruitless distillation experiment.

Simple distillation is effective in terms of its setup and the time it takes to distill a liquid. Compared to the steam distillation, simple distillation required less apparatus to be used and required less time to finish its distillation process. Simple distillation however, is limited to mixtures that have large differences in boiling points. If simple distillation is done on a mixture that had fairly close (<80C) boiling points, this would not be a very effective means of separation of constituents.

Steam distillation is most useful in trying to avoid decomposition of organic compounds. By providing additional vapor pressure, the researchers lowered the required heat needed to boil the liquid. This prevented the organic material from decomposing before being distilled off and separated from the original mixture. Steam distillation however, requires more equipment in comparison to simple distillation.

It is recommended for researchers to absolutely make sure that your setup is properly assembled and has no leaks where steam or gas might escape. This is crucial for distillation relies heavily on the gas evolved from the heated mixture that is then cooled to be turned into a liquid. It is also recommended that researchers try different organic compounds to thoroughly see the effects of volatilities in distillation setups.

References

Baluyut, J. G., & De Castro, K. A. (2001). Organic Chemistry Laboratory Manual for Chemistry Students Part 1. Intramuros, Manila: Mapua Institute of Technology.

Beychok, M. (2012, January 1). Volatility (chemistry). Retrieved from The Encyclopedia of Earth:

http://www.eoearth.org/view/article/172247/

CHM145L Organic Chemistry 1 Laboratory 1 s t Quarter, S.Y. 2015-2016

CHM145L Organic Chemistry 1 Laboratory 1 st Quarter, S.Y. 2015-2016

Klein, D. (2012). Organic Chemistry. In D. Klein, Organic Chemistry (p. 41). New Jersey: John Wiley and Sons, Inc.

Samal. (2015). Department of Chemistry. Retrieved from Univeristy of Massachusetts:

http://www.chem.umass.edu/~samal/269/cry

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