Experiment 2: Simple Distillation and Determination of an Unknown

Sample.

Juliana Marie Z. Gaballo

12A - MNO1

INTRODUCTION

Distillation is a process that aims to separate and purify compounds through

determination of its chemical properties. This process is based off of the difference in boiling

points of the compounds involved. A chemical property that can affect boiling points is the

presence of intermolecular forces in a compound, which determines the energy required to

break those bonds to transition to a higher energy state that affects its physical state (e.g., from

liquid to gas) (4). The technique used for this experiment is of the liquid-liquid simple

distillation. In general, the mixture is composed of two liquids, where one has a lower boiling

point than the other, which will make it easier to separate the two. The boiling point difference

must be significant enough between the two liquids for noticeable results.

The purity and identity of the sample obtained from distillation would also be

determined through boiling point determination by noting down the temperature of the distillate

during the process. If the distillation was correctly performed, the results would have reflected

a similar range of temperatures close to the boiling point of the sample to be obtained from the

mixture. The issue that can emerge from this technique would be when the distillation was

performed incorrectly and resulting in different temperatures from the assigned sample.
DATA AND OBSERVATIONS

Table 1: Observations of the Mixture Distillation.

Temperature/s (°C) Observation

The mixture was dyed with pink and smelled like rubbing alcohol.
0 °C [initial]
Its volume was 32 mL.

Only a small amount of forerun was collected (only 10 drops,

45 °C
0.5mL).

The temperature accelerated extremely quickly at this range. The

45 - 53 °C forerun was quickly transferred to a test tube to collect the first

distillate.

53 – 69 °C The rate of increasing temperature slightly slowed at this range.

Distillate was still being collected, but temperature slowed down to

69 – 81 °C changing only 1-2 degrees per mL. Only one distillate (21 mL) of

the mixture was collected.

The collected distillate was used for the boiling point determination.
After Distillation
Its washings had a faint wine-like smell.

Table 2: Boiling Point Determination of the Distillate.

Volume (mL) Temperature (°C) Volume (mL) Temperature (°C)

0 43 12 76.5

1 52 13 77

2 59 14 77.5

3 65 15 78
 4 69 16 78.3

5 71 17 78.5

6 72.3 18 79.5

7 73 19 80

8 73.5 20 81.5

9 74.5 21 82.5

10 75 22 83

11 76

Table 3: The Guessed Sample Compound and the Actual Sample Compound

Final Guess Ethanol

Actual Sample Isopropanol

DISCUSSION

There were five out of eight compounds that could have been the identity of the sample,

which were methanol, ethanol, isopropanol, hexane, and ethyl acetate as they had low boiling

points. With this, a water condenser was used. The mixture would be separated to its individual

compounds to obtain the sample through liquid-liquid distillation. Butanol and propanol were

ruled out because of their higher boiling points. Chloroform was also omitted from the possbile

identites of the sample due to the lack of its disposal container G703.
 (Figure 1. The Distillation Setup)

Boiling points were the chemical property of focus as the process concentrated on the

difference between the sample and the accompanying liquid for further determination. They

are affected by molecular interactions and molecular mass of their respective compounds. The

molecular interactions include intermolecular and intramolecular forces; however, they only

affect boiling points through intermolecular forces as they determine bond strength through

attractions and the difference of electronegativity (McMurry, 2016). The molecular mass of the

compound is also a factor due to the fact that a higher mass means more atoms involved hence

more intermolecular forces. Covalent bonds necessarily do not affect and not get affected

because they are not attractions but equally shared electrons, only needing to overcome the

intermolecular forces which are weak in nature, hence the reason for the low boiling points of

the organic samples of the experiment.

The mixture was heated in the round bottom (r.b.) flask with an initial volume of 32

mL and was dyed pink. Its smell was immediately noted to have a sharp odor that is present in

rubbing alcohol, which its main component is isopropanol and has a boiling point of 82 °C.
The forerun of the mixture during the distillation appeared at 43 °C, but the temperature

accelerated soon after to 53 °C, hence only 0.5 mL of it was collected before transferring it to

a test tube. The collection of the distillate continued until the temperature reached 81 deg

Celsius, where the stagnation of the temperature occurred at 69 °C until 81 °C. This was an

error due to the early collection of the distillate, where it was noted that the temperature started

to slow down at 53 °C but truly stagnated at 69 °C onwards. Only one batch of distillate was

collected, with a volume of 21 mL and a 65.6% recovery of the mixture. The washings of the

liquid left behind in the round bottom flask had a distinct but faint wine smell, which indicated

ethanol.

Vol (mL) Vs.Temp. (Deg Celsius) in Simple

Distillation
90
80
70
Temperature

60
50
40
30
20
10
0
-5 0 5 10 15 20 25
Vol (mL)

Figure 2. Scatter Plot Graph Between the Volume (mL) and Temperature (°C) in the

Simple Distillation.

The batch of distillate was then taken to boiling point determination through distillation

by observing temperatures per 1 mL fraction. Due to the previous mistake, it was assumed that

the distillate was not mostly of the pure sample. Overall, the distillation temperatures for the

boiling point determination of the distillate stagnated between the temperatures of 76.5 – 78.5

°C. The range included the boiling point of ethanol at around 78 °C, which was the final,
assumed identity of the sample as it seemed to align with the trends of the temperatures noted.

However, the actual identity was isopropanol, which could not have been tested for due to

volume constraints.

Temp. (°C ) Vs. Volume (mL) of the Distillate for

Boiling Point Determination
90
80
70
Temperature (°C )

60
50
40
Temp. (Deg Celsius)
30
20
10
0
0 5 10 15 20 25
Distillate Vol. (mL)

Figure 3. Temperature (°C) Vs. Volume (mL) during Boiling Point Determination.

This indicated a problem on which the liquids were distilled at a lower temperature

below the expected boiling point. This must have been a limitation on the apparatus, because

as seen from Figure 1, the temperature of the vapors boiled could not be measured accurately

due to the closeness of the still head to the water condenser. The vaporized mixture would

immediately go through the water condenser while still being measured by the thermometer,

which the water condenser could have cooled down the vapors and lowered their temperatures.

Another possibility was that the mixture contained miscible liquids that provided only a narrow

difference of boiling points, which could have affected the temperatures measured as the

mixtures vaporized. As both ethanol and isopropanol were indicated, the assumed boiling point

difference was only 5 °C, from 78 °C to 82 °C. This might have also been the reason for the

previous mistake as the difference was insignificant and should be more than 20 °C (Simple
distillation, n.d., Jove), making it unable to highlight noticeable results through temperature

changes (e.g., rises and stagnation in temperature) that could have also been shown through the

graphs as one vaporizes while the other presumably should have still been a liquid.

It should also be noted that temperatures also remain constant during phase changes

after reaching the required temperature to overcome intermolecular forces that retain certain

physical states. This is the reason why the temperature recorded by the thermometer remained

somewhat constant while the temperature of the liquid still increased as it only detected the

temperature of the vapor. Unless fully condensed by the apparatus, or vaporized, the

temperatures would reach a plateau as the vapors reached closer and detected by the

thermometer than the liquid below it. The temperature in vaporization remains constant until

the phase change is compete by one compound in the mixture or it was immediately transferred

to another phase and container (Tec-Science, 2022). This might have also caused the error in

the experiment as while the phase change was still occuring for one compound in the mixture

(from liquid to solid), the other compound might have already formed vapors as its temperature

was still rising due to the contact to the Bunsen burner, again assuming if the mixture of the

sample did not have a significant difference of boiling points and containing only ethanol and

isopropanol.

Overall, the sample of isopropanol was incorrectly guessed to be ethanol due to the

liquid distilling at lower temperatures as the data supported its boiling point. However, the

smell indicated the sample as it was like rubbing alcohol. The errors in this experiment were

that the distillate collected from the first distillation was not of the pure sample due to the wrong

collection of forerun and distillate, however the limitations of the apparatus also added for the

wrongful determination of the sample during the boiling point determination, as well as the

narrow difference of boiling points in the mixture of ethanol and isopropanol. Simple liquid-

liquid distillation was not an appropriate process for the experiment to determine the sample in
a narrow difference of boiling points and requires more complex processes such as azeotropic

distillation.

SAMPLE CALCULATIONS

𝐶𝑜𝑙𝑙𝑒𝑐𝑡𝑒𝑑 𝐷𝑖𝑠𝑡𝑖𝑙𝑙𝑎𝑡𝑒 𝑣𝑜𝑙.(𝑚𝐿)

1. Theoretical Percent Yield (%) = ( 𝑋 100)
𝐼𝑛𝑖𝑡𝑖𝑎𝑙 𝑚𝑖𝑥𝑡𝑢𝑟𝑒 𝑣𝑜𝑙. (𝑚𝐿)

SUPPLEMENTAL QUESTIONS

1a. Which has a higher boiling point?

1-Butanol or n-pentane

- Butanol has the higher boiling point because of the difference in electronegativity

present in the compound.

1 – Butanal or 1 – butanol

- Butanal has the higher boiling point because the double bond of C=O, which

requires more energy to break.

Neopentane or n-pentane

- N-pentane has a higher boiling point because of its higher surface area than

neopentane, which has a lower surface area due to its branches making it look

more spherical,

Methanol or butanol

- Butanol has a higher boiling point because of its higher surface area to methanol.

1b.) Ranking from Lowest to Highest Boiling Point in a Molecular Level:

- Chloroform: Has polar bonds that can quickly be broken down due to

intermolecular forces present in its 3 C-Cl bonds.

- Methanol: Has polar covalent bonding but also contains a hydroxyl group. Has

low surface area as well due to small number of atoms.

 - Hexane: A covalent compound that has high molecular mass due to more carbons

but has weaker intermolecular forces due to its covalent bonding that leads to

faster evaporation.

- Ethyl Acetate: Lacks hydrogen bonding – the strongest intermolecular force

- Ethanol: A polar compound that also has hydrogen bonding from hydroxyl group

- Isopropanol: Lower boiling point than propanol due to branching.

- Propanol: Has high surface area due to its 3 carbons and hydroxyl group that

accounts for hydrogen bonding, only beaten by butanol because it has 4 carbons.

- Butanol: Highest number of carbons than the other compounds (except hexane),

and also has a hydroxyl group, leading to hydrogen bonding that requires more

energy which leads to highest boiling point

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