Combustion of Pentanol and Cyclohexane in Different Ratios

Aim:

To investigate the effect of different mixtures of cyclohexane to pentanol ratios (1:4, 1:3, 1:1.4 and 0:1) in
a total of 60 mL solution, on their efficiency when combusting them as fuels, after measuring the
difference in mass produced by burning them up in a spirit burner, in order to increase the temperature of
60 cm3 of water by 10⁰C, then calculating the enthalpy of combustion for each of the ratios.

Hypothesis:

I hypothesize that the larger the volume of cyclohexane measured within the ratio, the lower the enthalpy
of combustion, so there will be a larger decrease in the mass of the pentanol and cyclohexane solution,
after increasing the temperature of the 60mL of water by 10 ⁰C. Hence, the ratio 0:1 of cyclohexane to
pentanol will have the highest enthalpy of combustion, after that 1:4 ratio will have the second highest
enthalpy which is followed by the 1:2 ratio, and lastly the 1:1 ratio, that will have the lowest enthalpy of
combustion, this is due to cyclohexane being the most stable cycloalkane, and thus needing a higher
energy to break its bonds and combust it, which decreases the enthalpy of combustion.

Scientific Background:

Alcohols are a homologous series of organic compounds, that have the functional group of –OH.
Alcohols are extremely efficient fuels, and are commonly combusted, as they have high burning
velocities, and can produce a huge amount of energy, which is why alcohols are frequently used in
internal combustion engines. Also, environmentally, a lower volume of greenhouse gasses is emitted from
alcohols, so they do not have a high negative effect on the Earth’s atmosphere and the ozone layer,
keeping it healthier for the environment, when compared to the petroleum-based fuels, which produce
various greenhouse gasses like carbon dioxide, that harms the ozone layer and effects the planet
negatively, mainly causing global warming. Also, alcohols are renewable, for example, ethanol is made
up of several plant materials, so it can be renewed, and it will not end soon. These days, alcohols are used
as replacements, for petroleum-based fuels, that are harmful for the environment and are non-renewable,
meaning they will end one day.  

Looking at cyclohexane C6H12 and pentanol C5H12O we could see that; cyclohexane has 6 C-C
bonds with an energy of 80 kcal/mole and 12 C-H bonds with a bond energy of 98 kcal/mole which
makes the total energy of the bonds 1656 kcal/mole. On the other hand, pentanol has 4 C-C bonds, 11 C-
H bonds, 1 C-O bond with an energy of 78 kcal/mole, and 1 O-H bond with an energy of 110 kcal/mole
which makes a total of 1586 kcal/mole. Therefore, when looking at the total bond energies of both
 compounds we can see that upon combustion cyclohexane should exert the higher amount of energy,
however, cyclohexane is considered more stable than chain alkanes due to Baeyer strain and ring strain,
therefore breaking the C-C and C-H bonds may be harder than the C-C and C-H bonds in pentanol, which
then contributes to decreasing the efficiency of it as a fuel.

Variables:

Independent: changing the ratio of cyclohexane to pentanol (0:1, 1:4, 1:3 and 1:1.4)

Dependent: Measuring the efficiency of combustion as fuels by measuring the change in mass then the
enthalpy of combustion

Controlled:

 Total volume of cyclohexane and pentanol (60 ml)

 Volume of water (60 cm3)
 Distance between alcohol and water (10cm)

Manipulation of Variables:

Variable Why its controlled How its controlled

IV: changing the ratio of The ratio of alkanes to alcohol in By accurately measuring the volume
cyclohexane to pentanol (0:1, 1:4, fuels can affect the rate of of the alcohol pentanol and the
1:3 1:1.4) combustion, as cyclohexane has a alkane, cyclohexane using the
stable structure, so it’s expected to measuring cylinder from the bottom
decrease the rate of combustion meniscus, after calculating the ratio
in mL of each of the fuels used.
DV: measuring the efficiency of the The efficiency of fuels combustion is Through measuring the difference in
alcohol pentanol in combustion, measured to determine if alkanes can the mass of the alcohol before and
through measuring the difference in enhance fuel properties or vice versa. after their combustion, and after
the mass of the alcohol before and calculating their enthalpy of
after their combustion, and after combustion.
calculating their enthalpy of
combustion.

CV1: Total volume of cyclohexane The total volume of the mixture can The total volume is controlled by
to pentanol 60mL affect the results, as the larger the accurately measuring the volume of
volume, the larger the mass of the alcohol pentanol and the alkane,
 alcohol will remain.
CV2: Total volume of water 60mL The larger the volume of water, the
more time is needed to heat it up, and
thus the more alcohol is needed.
CV3: Distance between alcohol The larger the distance between the
mixture and water, which is 10cm alcohol and water, the longer the
time needed for it to heat, and so
more alcohol will be used up.
cyclohexane using the measuring
cylinder from the bottom meniscus,
and ensure that the total is 60mL
The total volume is controlled by
accurately measuring the volume of
water, using the measuring cylinder
from the bottom meniscus
It will be measured by a ruler to
ensure that the distance between the
alcohol mixture and water, is exactly
10cm

Materials:

 280 cm3 of tap water ±0.1mL

 178 mL of (pentanol)
 62 mL of ( cyclohexane)
 A Thermometer ±0.5ºC
 A spirit burner
 5 conical flasks ±0.1mL
 A clamp stand
 A measuring stick / ruler ±0.1cm
 A measuring balance ±0.02g
 A measuring cylinder ±0.1mL
 A lighter

Method:

1. Wear a lab coat and goggles

2. Measure 60mL of pentanol for the first ratio to cyclohexane (1:0) into a measuring cylinder, and
read the measurement from the lower meniscus, to measure exactly 60mL without parallax errors
3. Pour the measured pentanol into the spirit burner
4. Place the wick in the spirit burner
5. Place the lid of the spirit burner on
 6. Put the spirit burner on the measuring balance, to measure the alcohol and spirit burner’s mass
before combustion
7. Record the mass of the spirit burner before combustion using a pen and paper in an organized
table
8. Fill the conical flaks with 70mL of cold, fresh, tap water, and measure the 70mL’s from the lower
meniscus at eye level
9. Place a thermometer in the water to measure its initial temperature, and record it in an organized
table
10. Place the conical flask with the water on the clamp stand and tighten it, for the flask to stay stable
and not falling from being too lose, nor too tight for it to shatter
11. Use the ruler to measure 15cm between the spirit burner and the conical flask
12. Place a thermometer in the conical flask, to keep an eye on the temperature rise in the water
13. Light up 1 fire match and use it to light the spirit burner up after removing its lid
14. Keep the spirit burner lit until the temperature of the water reaches 30°C, then put its lid on
15. Record the temperature of the water after it gets heated, in an organized table
16. Measure the mass of the spirit burner after the water is heated, using a measuring balance
17. Record its mass after combustion in a table
18. Subtract the initial mass from the final mass of the alcohol and record in the table
19. Subtract the final temperature from the initial temperature of the water and record it in the table
20. Repeat steps 2-19 for all the other remaining ratios of pentanol to cyclohexane (4:1, 3:1 and
1.4:1)
21. Return all the materials back to their places
22. Take off the lab coat and the goggles

Safety precautions:

Risk Damage Prevention

Pentanol is irritating to the eyes, skin and
respiratory tract, and its exposure at
high levels could cause lowering of
consciousness.
Cyclohexane can cause Irritation and burns as
well as, dizziness, light-headedness.
Fire / flame Skin burns and damage
Handle with care and wear gloves,
wear lab coat and goggles to prevent
direct contact of substance with skin
Handle with care and wear gloves
wear lab coat and goggles to prevent
direct contact of substance with skin
Handle with care, wear lab coat and
 goggles to prevent direct contact of
flame with skin, a close wash station
should be nearby

Ethical precautions: there are no living things used, thus there are no ethical precautions.

Environmental precautions: not disposing the warm alcohol solutions through the sink, rather disposing
them in bags to avoid environmental damage, and minimal quantities to minimize wastage.

Raw Data Table:

Volume of Volume of Mass of Initial Final Initial Final Mass of

pentanol cyclohexane Water temperature temperature mass of mass of the
±0.1g ±0.5ºC ±0.5ºC solution solution solution
±0.02g ±0.02g consumed
±0.02g
60 0 60.0 22.5 32.5 237.75 231.91 5.84

50 10 60.0 19.5 29.5 235.47 229.53 5.94

45 15 60.0 20.3 30.3 220.44 214.37 6.07

35 25 60.0 19.0 29.0 216.81 210.5 6.31

Processed data table (Rama):

Calculations:

∆T (controlled): 10°C

0(cyclohexane):1(Pentan-1-ol)

Mass of fuel used= 237.75-231.91= 5.84 grams

Q= 60*4.18*10= 2508/1000= 2.508 kJ

Moles of Pentan-1-ol= 5.84/88= 0.06636

∆H= 2.508/0.06636= 37.79 kJmol-1

1(cyclohexane):5(Pentan-1-ol)
Mass of fuel used= 235.47-229.53= 5.94 grams

Moles of Pentan-1-ol= 5.94/88= 0.0675

Moles of cyclohexane= 5.94/84.16= 0.0705

∆H (Pentan-1-ol)= 2.508/0.0675= 37.16

∆H (cyclohexane) = 2.508/ 0.0705= 35.57

37.16*83.3%= 30.95428

35.57* 16.7%= 5.94019

∆H 1(cyclohexane):5(Pentan-1-ol)=

30.95428+5.94019= 36.89 kJmol-1

1(cyclohexane):3(Pentan-1-ol)

Mass of fuel used= 220.44-214.37= 6.07 grams

Moles of Pentan-1-ol= 6.07/88= 0.0690

Moles of cyclohexane= 6.07/84.16= 0.0721

∆H (Pentan-1-ol)= 2.508/0.0690= 36.36

∆H (cyclohexane) = 2.508/ 0.0721= 34.77

36.36*75%= 27.27

34.77*25%= 8.69

1(cyclohexane):3(Pentan-1-ol)=

27.27+8.69= 35.96 kJmol-1

1(cyclohexane):1.4(Pentan-1-ol)

Mass of fuel used= 216.81-210.5= 6.31 grams

Moles of Pentan-1-ol= 6.31/88= 0.071

Moles of cyclohexane= 6.31/84.16= 0.075

∆H (Pentan-1-ol)= 2.508/0.071= 34.977

∆H (cyclohexane) = 2.508/ 0.075= 33.45

34.977*58.3%= 20.39

33.45*41.7%= 13.95

20.39+13.95= 34.34 kJmol-1

Conclusion + Data Analysis:

From the results, its clear that as the ratio of cyclohexane to pentanol increases, (1:1, 1:2, 1:4 and 0:1), the
enthalpy of combustion decreases, so the larger the volume of cyclohexane in the ratio, the larger the
decrease in mass of the alcohol solution that is needed to increase the temperature of 60mL of water by
10⁰C. Hence, the larger the volume of propanol used in the ratio, the larger the enthalpy of combustion.
This is due to the fact that cyclohexane is the most stable ring that is strain-free, and since the Strain
Energy (KJ/mol) of cyclohexane is 0, then it has a similar relative stability as long chain alkanes that are
not cyclic.

Moreover, the angle of strain occurs when the sp3 hybridized carbons in cycloalkanes do not have the
expected ideal bond angle of 109.5⁰, causing an increase in the potential energy. However, due to the
carbon-carbon ring bonds being capable of bonding angles at approximately 111 ⁰, which is close to the
optimal tetrahedral 109.5⁰ so angle strain has been eliminated, thus there will be no increase in potential
energy, and hence it will not increase the enthalpy of combustion. (LibreTexts)

To begin with, in the ratio 0:1, the enthalpy of combustion was 37.79 kJmol -1 which is the highest. Even
though pentanol has a lower enthalpy of combustion than cyclohexane (ΔcH° liquid (kJ/mol) = -3330.91
± 0.28, meanwhile cyclohexane, has an enthalpy of combustion = -3918.0 ± 0.75. However,
cyclohexane’s stable structure needs more energy to break its bonds, making pentanol more efficient as a
fuel. (National Institute for Standards and Technology)

Furthermore, the 1:4 ratio, had an enthalpy of 36.89 kJmol-1, which is lower than that of pentanol alone
being combusted, but larger than that of the ratio of cyclohexane to alcohol of 1:2, which is 35.96 kJmol-
1, since it contains a larger volume of cyclohexane, that will decrease the enthalpy with its stable
structure.

Evaluation:

Weaknesses:

- Soaking the cotton wick in the alcohol solution: soaking the wick in the alcohol solution will
decrease the total solutions’ volume, creating a systematic error in the experiment, as the total
volume of pentanol and cyclohexane will not have a total of 60mL. Moreover, having wicks of
different lengths and widths will create random errors, as some wicks will absorb more of the
solution than others, hence leading to various volumes of the solution combusted.
 - Alcohols are volatile, so keeping the pentanol open in the tube before combusting could have led
to its evaporation and hence decreasing its mass, specially since the tubes were open for different
times, so it leads to different rates of evaporation, and leading to random errors in the experiment.
- Heat losses from the flame resulting from the combustion of the alcohols’ solution are lost to the
surrounding air, hence not all the heat is used to increase the temperature of water, and this leads
to systematic errors.

Improvements:

- A thermal insulation technique should be used to minimize heat losses from the flame resulting
from the combustion of the alcohols’ solution to the surrounding air, in order to achieve a higher
thermal efficiency to the water.
- Soaking the cotton wick in a specific amount of alcohol (such as 10mL other than the one in the
spirit burner) after ensuring that all wicks are of the same length and width to have a fair test.

Strengths:

- Reading all measurements from the bottom meniscus of measuring cylinders in order to avoid
parallax errors and ensure accuracy in the measurements.
- Using the fume hood to measure the enthalpy of combustion for the ratios containing
cyclohexane

Work Cited

“3.4: Stability of Cycloalkanes - Ring Strain”. Chem LibreTexts, August 28, 2019,
chem.libretexts.org/Courses/Siena_Heights_University/SHU_Organic_Chemistry_I/
3%3A_Chapter_3_Conformations_and_Cycloalkanes/3.04%3A_Stability_of_Cycloalkanes_-
_Ring_Strain

“1-Pentanol - the NIST WebBook”. National Institute for Standards and Technology,
webbook.nist.gov/cgi/cbook.cgi?ID=C71410&Mask=2