CHEM 2203

Experiment 4- Distillation

Zhiqiao Xiao
101083582
Date performed: 23 May 2022
Lab partner: Haoyang Wang
Results and calculations

Table1. The recorded temperature(C) of 6 test tubes including at 1st drop, 2.5 ml and at
5.0 ml.
Test Tube # Temperature at 1st Temperature at Temperature at
drop (C) 2.5 ml (C) 5.0 ml (C)
1 64.5 66.0 67.5
2 65.5 68.6 68.6
3 67.1 68.0 69.5
4 69.0 70.5 72.0
5 72.0 73.0 74.0
6 74.0 74.9 75.0

Table2. Solubility, Refractive Index (RI), alcohol test and physical observations of test tube
#2 and #5.
Test Tube # Solubility Refractive Alcohol Test Physical
Index (RI) Observations
2 Soluble in water 1.3442 Red, ROH Transparent
present liquid
5 Soluble in water 1.3635 Red, ROH Transparent,
present colorless

The temperature increased from that of 1 st drop in the beaker to at 2.5 ml and at 5.0 ml. For
example, for test tube #1 the starting temperature at 1 st drop appeared to be 64.5 C, increased to
66.0 C and at 67.5 when at 5.0 ml. Yet, there was exception of test tube # 2, the temperature at
2.5 ml were the same as at 5.0 ml, with temperature of 68.6 C. The Boling point also increased
from test tube #1 to test tube #6, ranging from 64.5C to 75C.
The chemical test for test tube #2 and test tube #5 were similar, they were all soluble in water,
appeared to be red when mixing with ceric ammonium nitrate due to the presence of alcohol
group (OH), they were appeared to be transparent and colorless. Yet the Refractive Index (RI) of
the 2 test tubes were slightly different from each other, with test tube #2 of 1.3442 and test tube #
5 of 1.3635

The identification of the mixture were Methanol and Ethanol, based on their boiling point,
Refractive Index test as well as the alcohol test. Since both mixtures were appeared to be red
when mixing with ceric ammonium nitrate. as well as the RI values were close to that of the
literature values, methanol of 1.3286 and Ethanol of 1.3609.

Calculation of theoretic boiling point and Refractive Index

Methanol
Literature boiling point of methanol (1): 64.7C at 760 mmHg. The lab room pressure was
recoded to be 758 mmHg. Thus, theoretic boiling point = 64.7C – [ 0.037C/mmHg ×
(760mmHg – 758mmHg)] = 64.63C.
Literature RI of methanol: 1.3288 at 760mmHg. The theoretic RI = 1.3288 + [0.00045C
-1
× (20C – 20.4C)] = 1.3286.

Ethanol
Literature boiling point of ethanol: 78.5C at 760 mmHg. Lab room pressure of 758
mmHg. Theoretic boiling point = 78.7C – [ 0.037C/mmHg × (760mmHg – 758mmHg)] =
78.63C.
Literature RI of ethanol: 1.3611 at 760mmHg. The theoretic RI = 1.3611 + [0.00045C -1
× (20C – 20.4C)] = 1.3609
Discussion

The purpose of this experiment is to separate a mixture of two unknown liquid compounds with
fractional distillation. As well as to identify the unknown compounds based on the solubility,
boiling point, reaction with ceric ammonium nitrate as well as their Refractive Index (RI).

Fractional distillation is the separation of mixture with different components into the state of
fractions, this can be applied through by heating component to a specific temperature at which
the fraction of the compound vaporizes. (2) The use of fractionalization column is important in
this experiment since it separate two different compounds based on the differences of their
volatility.
The boiling point of a liquid is at which its vapor pressure equals to one atmosphere (760
mmHg).
The fraction #2 and # 5 are the purest among all the fractions.

Ceric ammonium nitrate test is used to determine if the alcohol group are present in the solution:

(NH4)2[Ce (NO3)6] + 3 ROH >> [Ce (NO3)4(ROH)3] + 2NH4NO3

The presence of [Ce (NO3)4(ROH)3] is a red complex, thus, if the compound reacts with Ceric
ammonium nitrate and the color change in red, there is alcohol group present in the solution. (3)

(4)
Refractive index (RI) defines as ratio of speed of light travel to that in a compound. By
comparing the literature RI to that of the experimental one, the compound can be identified. The
theoretic RI was calculated because the vapor pressure of the lab was different than that of the
temperature of the literature values. The theoretic RI of methanol and ethanol were calculated to
be 1.3286 and 1.3609. The experimental RI of methanol and ethanol were 1.3442 and 1.3635.
According to the data, the two mixtures can be determined by comparing their experimental RI
and the theoretic RI.
The water solubility test can be conducive to distinguish polar and non-polar compounds.
Hexane is non-polar, and water is polar. According to the rule of “like dissolves like”, hexane is
not soluble in water. Based on the results of the experiment, both mixture #2 and #5 were soluble
in water. Thus, the possibility of hexane can be eliminated. Methanol and Ethanol are considered
as polar, and they are soluble in water. Based on this information, it is beneficial to determine the
unknow compounds.

Source of error occurred in this experiment include the air in the fractional column, this also
cause the boiling point of the substance different than that of the literature values. RI values
different than that of the literature due to the difference of the vapor pressure in the lab room.

Distillation is the effective analytical technique used to separation liquids when they have
different volatilities and boiling point. Through fractional distillation, one liquid can become
fraction when heat is being applied in the column. Therefore, distillation is being favored when
the mixture has different boiling point and volatilities.

One technique can be applied to identify the compound after distillation, Desorption
Atmospheric Pressure Chemical Ionisation Mass Spectrometry (DAPCI-MS). In industry of
whiskies, this analytical method is being used to distinguish authentic whiskies and counterfeit
ones after the process of distillation. (5)
Conclusion

The purpose of this experiment is to separate two components by fractional distillation. To

determine the unknow compounds based on their boiling point, solubility, reaction with ceric
ammonium nitrate as well as the Refractive Index. The boiling point of the purest test tubes were
68.6C for test tube 22 and 78.3 for test tube #5. The Refractive Index (RI) for test tube # 2 was
appeared to be 1.3442 and for test tube #5 of 1.3635. Both test tube #2 and #5 were soluble in
water and they turned red when mixing with ceric ammonium nitrate, which indicated the
presence of the alcohol groups in these two compounds. According to the results, the two
unknow mixture #5 were successfully to be determined, the mixture were methanol and ethanol.
Future direction to identify the separation of the compounds can be through test of polarity and
by determine their miscibility in water.
References

(1) White, C.A.; Buchanan, G.W. Distillation. CHEM 2203/2204- Organic Chemistry
Laboratory Manual 2022-2023. pp.1-5.

(2) Young S. Fractional distillation. 1903. Macmillan and Company, limited.

(3) Goswami, P.; Chowdhury, P. Ceric ammonium nitrate (CAN)—a useful catalyst for the
rapid and high-yield esterification of carboxylic acids and alcohols with special reference
to steroid and other multi-functional natural products. 2000. New Journal of Chemistry.
pp.955-957.

(4) Shrivastava, A. 3-Plastic Properties and Testing. 2018. Introduction to Plastic

Engineering. pp. 49-110. https://doi.org/10.1016/B978-0-323-39500-7.00003-4

(5) Aylott, R.; MacKenzie, W. M.Analytical Strategies to Confirm the Generic Authenticity
of Scotch Whisky.2010. Journal of the Institute of Brewing, 116(3), 215–229.
DOI:10.1002/j.2050-0416.2010.tb00424.x