Boiling Point, Refractive Index:

ID of a Petroleum Hydrocarbon
Katie LaMontagne
9/23/2020
Organic Chemistry 1 Lab CHM 2210L
Fall 2020
Experiment 4

Introduction

Gasoline, a mixture of chemicals, is synthetically blended to produce a fuel with desired

characteristics. All fuel types are derived from petroleum which must be refined before it can

be a useable product. The refining process includes a simple separation and purification

which involves it to go through physical and chemical changes.

In the first step, petroleum is fractioned in a distillation tower (Hickman still) where it is

purified and the liquid separates according to their boiling-point ranges. One of the major

purposes of refining petroleum is to convert low-octane components of petroleum into higher-

octane compounds.

The purpose of this experiment is to attempt to identify an unknown hydrocarbon from a

1:1 mixture of n-Hexane and Toluene through the process of collecting fractions via simple

distillations, compare boiling point ranges, refractive indices, and density. In addition, other

kinds of evidence such as the appearance of a precipitate with a test reagent and spectral

evidence can theoretically help identify an unknown. The density of the liquid is determined

by measuring its volume accurately.

 
Table of Relevant Properties

Chemical Molecular Boiling Density Vapor Refractive Octane Hazardous

Name Weight Point g/mL at Pressure Index at No. Characteristics
( C)
o
25 C
0
at 20 C
0

20 C
0

n-Hexane 86.18 g/mol 69 C 0

0.659   1.3749 26 Flammable, can irritate
CH
6 14 g/mL at 120 mmHg skin and eyes, and
25 C
0
hazardous if inhaled.

Toluene 92.14 g/mol 110.6 C o

0. 865   1.4967 104 Flammable, can irritate
CH
7 8 g/mL at 22 mmHg skin and eyes, and
  25ºC hazardous if inhaled.

Prelab Calculations

Refractive Index:
nD20 = nDT + 0.00045 (T -200C)

Boiling Point Correction:

100°C=BPobs - (600mmHg-760 mmHg) x 0.045°C /mmHg

Percent Composition:

Measured nD = x*(nD of n-Hexane) + (1-x) * (nD of Toluene)

Materials

Chemica Supplie Equipment

l s
 n-Hexane Labels Hot plate
Toluene Pen Corning dish
Manual Sand
Abbe refractometer
Digital refractometer
Automatic pipette
Hickman-Hinkle still
Conical vial
Boiling chip
Capillary tube
Thermometer
Data Tables

Simulated Data: Standard Scale 

Purification and Boiling-Point Determination 

Total Volume of hydrocarbons (μL) (from video) ____2000 μL_____ 
Boiling point range (fraction 1) ___71.3oC – 78.3oC_____ 
Boiling point range (fraction 2) ___78.4oC – 84.6oC_____
Boiling point range (fraction 3) ___85.6oC – 110.1oC____

Refractive Index Measurement 

Hexane Refractive Index (analog) ___1.3783______
Hexane Refractive Index (digital) ____1.37959_____
Toluene Refractive Index (analog) ____1.4954_____
Toluene Refractive Index (digital) _____1.49671____
Fraction 1 Refractive index (analog) ___1.3933_____ 
Fraction 1 Refractive index (digital) ____1.39530____ 
Fraction 2 Refractive Index (analog) ___1.4040_____
Fraction 2 Refractive Index (digital) ____1.40504____
Fraction 3 Refractive Index (analog) ___1.4759_____
Fraction 3 Refractive Index (digital) ____1.47843____ 

Composition of fraction 1 __87% Hexane; 13% Toluene___ 

Composition of fraction 2 __78% Hexane; 22% Toluene__
Composition of fraction 3 __17% Hexane; 83% Toluene___

Observations

The experiment was conducted using the Hickman-Hinkle still head for distillation

where two hydrocarbons n-Hexane and Toluene were placed in the vial and separated as the

boiling points varied between the two. According to literature, n-Hexane has a boiling point of
690C and Toluene is 110.60C. After collecting the boiling point ranges of our three fractions

we measured the refractive index by using both the Abbe refractometer and Atago RX 5000i

and recorded our results. This is then used to calculate the percent compositions of our three

fractions. The temperature of the chemistry lab was 22.10C so aluminum foil was used to

partially insulate the setup.

Calculations
Results, Analysis & Discussion

In this lab we observed a simple distillation procedure by heating compounds, recording

the boiling point range, and collecting the fractions to determine their refractive indices. After
the mixture reached the average boiling point for the first compound, which was mostly n-

Hexane, we collected it as fraction one. N-Hexane was the first liquid to distill because it is

the lower boiling solvent. Next, once the temperature was in-between the boiling points of n-

Hexane and Toluene our second fraction was collected. When the mixed solutions boil n-

Hexane will evaporate off first into the still-head.

The distillate was collected in three fractions with boiling point ranges of: 71.3oC –

78.3oC, 78.4oC – 84.6oC, and 85.6oC – 110.1oC respectively.

The refractive index of each fraction was measured by using two different devices: the

Abbe refractometer (analogue) and the Atago RX 5000i (digital). The values of the analogue

fractions were 1.3933, 1.4040, and 1.4759 respectively. The values of the digital fractions

were 1.39530, 1.40504, and 1.47843 respectively. The percent composition of n-hexane for

both analogue and digital measurements were calculated by applying the following formula:

Measured nD =  x*(nD of n-hexane) + (1-x) * (nD of toluene)

According to our calculations the percent composition of n-hexane in our fractions were

roughly 87%, 78%, and 17% respectively. Therefore, we can assume that these results do

not appear to be purely hexane nor toluene. However, when we compare the data from our

experiment to that of literary review we can conclude that their boiling point and refractive

indices are very close indicating a successful experiment.

Post-Lab Questions
1. The range of the pipette to measure the hydrocarbon is 100-1000 μL, which is a

maximum of 1mL for the automatic pipette.

2. n-Hexane is the liquid that distilled off first because it’s the lower boiling solvent.
3. The Hickman-Hinkle still-head was used for the distillation.

4. The purpose of using the aluminum foil was to partially insulate the setup because of

the cold room temperature of the lab and also because of the high boiling point of

fraction 3 which is mostly toluene.

5. You can measure the refractive index by using the Abbe refractometer (analogue) or

(digital) which was the Atago RX 5000i.

6. It is 589 nanometers; the wavelength of light that will pass through the liquid to

measure the refractive index.  When the light passes through the liquid it will be

refracted or bent.

7. The analog instrument reads 5 significant digits.

8. The digital instrument reads 6 significant digits.

9. Corrected refractive index = 1.3816; corrected boiling point is 90.60C; density is equal

to 0.665 g/mL which according to our calculations our unknown is likely to be 2,3

dimethylpentane.
Conclusion

In conclusion, chemical fuels can be blended to achieve desired characteristics. A

mixture of hexane and toluene was distilled to separate the compounds from each other.

Hexane typically has a boiling point around 690C and toluene has a boiling point around

1100C. Due to the difference between the two, hexane will boil first leaving toluene behind

and the mixture of these two solvents will have a boiling point range between that of pure

hexane and pure toluene. Due to the limitations of this experiment we were unable to retrieve

the density of our unknown compound.

References

1.   Wade, L. G. (2017). Organic Chemistry, Books a la Carte Edition (9th ed.). Pearson.

2.  North Campus, B. (n.d.). Organic Chemistry Laboratory Manual CHM2210L (Vol. 2).

Pearson.

3. Hexane. (n.d.). Retrieved September 26, 2020, from

https://pubchem.ncbi.nlm.nih.gov/compound/8058

4.  Toluene. (n.d.). Retrieved September 26, 2020, from

https://pubchem.ncbi.nlm.nih.gov/compound/1140