Organic Chemistry Laboratory: Report 6: Reflux Reaction

International University, Vietnam National University - HCMC
School of Biotechnology
Department of Biochemistry
ORGANIC CHEMISTRY LABORATORY

REPORT 6: REFLUX REACTION
INSTRUCTOR: PhD. Hoàng Lê Sơn
TEACHING ASSISTANT: Nguyễn Thanh Phong
DATE OF SUBMISSION: 16-07-2019
Group member:
1. Trương Thị Ngọc Hằng - BTBCIU16041
2. Võ Minh Hạnh - BTBCIU16083
3. Nguyễn Hồng Anh Phương - BTBCIU16015
4. Nguyễn Tấn Phú - BTBCIU16057
Organic Chemistry Laboratory 1

I. Abstract
The target of this experiment is familiar with the techniques of reflux through isolating fatty
acids and lipids from coconut. The reflux reaction allows the reaction to be carried out at the
boiling point of the solvent and yet it prevents loss of the solvent or reagent due to
evaporation. The reactants for reflux experiments could be solid and liquid, or both liquids. As
the result of experiment, two spots at Rf value of 0.82 and 0.59 was shown from product
collected before and after removing solvent respectively. To remove solvent, rotatory
evaporator is used under specific temperature and pressure.
II. Introduction
Reflux is a technique involving the condensation of vapors and the return of this
condensate to the system from which it originated. It is used in industrial and laboratory
distillations. It is also used in chemistry to supply energy to reactions over a long period of
time. Some organic reactions are slow and can need an extended period of time to collect
result, so heating under refluxing is often used to increase the rate of reaction in a long time
without reagents escaping. A typical set up for reflux includes heating mechanism, a round
flask containing solvent and sample, and a condenser. As vapor from the boiling solvent
rises into inside of the condenser, it is cooled by the cool water on the outside and
condenses then fall back into the flask. In this way, a reaction can be maintained at the
boiling point of the solvent indefinitely.
* Structure of fatty acids and lipids:
Fatty acid, in biochemistry, is a hydrocarbon chains from C4 to C36 that end with -COOH
group
R represents for long hydrocarbon chain or aliphatic group, which is either saturated (un-
branched chain and all single bond) or unsaturated (more than 1 double bonds). Most
naturally occurring fatty acids have an un-branched chain of an even number of carbon
atoms, from 4 to 28. Fatty acids are known as non-polar molecules because of non-polar
hydrocarbon chains.
Lipid in biology and biochemistry is a biomolecule that is soluble in nonpolar solvents.
Non-polar solvents are typically hydrocarbons used to dissolve other naturally occurring
hydrocarbon lipid molecules that do not (or do not easily) dissolve in water, including fatty
acids, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E, and K), monoglycerides,
diglycerides, triglycerides, and phospholipids. Lipid is a triglyceride made up of ne glycerol
molecule and three fatty acid molecules. Depend on each type of lipid, the 3 rd- C links with
specific group or by specific linkages.
III. Materials and chemicals

Material
The materials used through this experiment were reflux apparatus with thermometer,
stand, heating mantle and water pump. The others were one 100 mL round- bottom flask,
four glass pipets, one cylinder (100 mL), two vials used to collect sample, one Erlenmeyer
flask and funnel served the function of filtration. The sample used in this experiment was
coconut flake. Besides, TLC plate, capillary, forceps, aluminum fold was used to set up TLC.
Method
First step was setting up the apparatus as the following picture.
Figure 1: Reflux apparatus

The second step was heating up the mixture of 15g of flake coconut and 100ml petroleum
ether in the round-flask under the reflux for one hour. It is important to note that boiling
chips were also added the flask in order to absorb, prevent eliminating.
The following stages were cooling down, and filter the mixture by filter paper and funnel.
After that, a small amount was save to run TLC later, the remained sample was
concentrated by rotary evaporation at 60 degree Celsius in 15 to 20 minutes until only oil
remaining.
Figure 2: Rotary evaporation

Finally, TLC was prepared by mixing petroleum ether, diethyl ether, glacial acetic acid with
the ratio 80:20:1, and introducing 2 dot of sample after filtration, after concentrating. The
solvent font was marked right after taking TLC plate out of beaker, and result was
observed, marked under UV light.

IV. Result
Figure 3: Filtered coconut solution into Figure 4: The final essential coconut
rotary evaporator to concentrate. oil after reflux reaction (on the right).
Figure 5: Observation of essential of coconut oil on the TLC plate after observing under
UV light.
Retention factor was calculated following:
Distance traveled by subtance 6.38
Rf oil ( before separated )= = =0.82
Distancetraveled by solvent front 7.78
Distance traveled by subtance 4.62

Rf of oil (after separated) = = =0.59
Distancetraveled by solvent front 7.78
V. Discussion
In this experiment, Petroleum ether is a solvent that can be readily vaporized when using
ordinary heat (oil ether boiling point ranges from 42˚C to 65˚C). That's why the reflux
method in this experiment is very essential. This method has a heat-free feature without
loss of fluid parts. Therefore, to isolate fatty acid and lipids from coconut, the appropriate
heat was conducted for solution and the liquid remained. Note that they could be explosive
if there are more gases in the system than liquid (too much heat).
When gas was heated and cooled down to be fluid again, most of the non-polar pair would
be vapor in the reflux phase. This could make the polar-non-polar solvent separation. In
this study, the non-polar solvent was oil–fatty acids and coconut water–lipids was the polar
solvent. To sum up, when the scheme was finished, only a small amount of the solvent–
petroleum ether–was lost and we succeeded in isolating coconut fatty acids and lipids,
which is oil and coconut water.
If the solution acquired is concentrated under decreased stress. The solvent, or petroleum
ether, would be separated from the solution and came out, so only oil and coconut water
was isolated: oil was above and coconut water was below. Reducing pressure only helped
vaporize the solvent (oil ether vapor pressure in 20C was 31 kPa). Finally, there were two
solutions used to compare by the TLC techniques.
In the TLC phase, the differences between the two sample was noted, with the solvent
included petroleum ether: diethyl ether: glacial acetic acid with a ratio of 80:20:1 after
heating through the UV chamber. As we knew before, the Rf value is based on polarity and
the less polar the molecule is as far as it moves on the plate. From the solvent's Rf before
concentration is 0.82 and the other's Rf is 0.59, this stated that the solution after
concentrating is more polar than before concentrating.
Reflux helps to finish the response and the pure liquid can be collected as this method will
proceed with a loop until the most volatile components in the liquid feed boil out of the
blend. This process also performs on its own, and is a closed system until the liquid feed
boils out of the mixture. Simple distillation is distinct because only solid or residue liquid
can be taken from it. It also has a scheme that laboratorians have to do more than reflux by
our side because the vapor is channeled to condenser and the residue has to be transferred
to other flasks. This method can also create a liquid that is not pure because there is only
the liquid that was set up at the initial with only temperature.

In case of separating a liquid from strong and residue, Reflux can also be used for simple
distillation, and in this situation two techniques can be interchanged. But if reflux is
required in the event of separating two or three liquids, it will offer a pure in any liquid.
Simple distillation, on the other hand, can't assist to have a pure liquid like reflux and it also
takes a lot of time because it require to do two or three times. So these two techniques can
be used to substitute one another in this situation.
VI. Conclusion
Reflux is a technique involving the condensation of vapors and the return of this
condensate to the system from which it originated. It is used in industrial and laboratory
distillation. It is also used in chemistry to supply energy to reaction over a long period of
time.
VII. Reference
 1. Organic Chemistry Laboratory Manual of the experiment 6. Ho Chi Minh:
International University, HCMC, 2017.
 2. Wikipedia. Reflux. Date Accessed October 17,
2017 https://en.wikipedia.org/wiki/Reflux
 3. "What is the purpose of reflux in chemistry?" Reference. N.p., n.d. Web.

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International University, Vietnam National University - HCMC

ORGANIC CHEMISTRY LABORATORY

TEACHING ASSISTANT: Nguyễn Thanh Phong

DATE OF SUBMISSION: 16-07-2019

1. Trương Thị Ngọc Hằng - BTBCIU16041

2. Võ Minh Hạnh - BTBCIU16083

3. Nguyễn Hồng Anh Phương - BTBCIU16015

4. Nguyễn Tấn Phú - BTBCIU16057

Organic Chemistry Laboratory 1

III. Materials and chemicals

Figure 1: Reflux apparatus

Organic Chemistry Laboratory 3

Figure 2: Rotary evaporation

Organic Chemistry Laboratory 4

Distance traveled by subtance 4.62

Organic Chemistry Laboratory 6

Organic Chemistry Laboratory 7

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