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Orange Oil

Ryan Kirdahy
SCH 121 02
March 30, 2016
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I. Title: Orange Oil Report

II. Introduction:

Simple, fractional, and steam are three forms of distillation that can be used to purify

compound due to a difference in boiling point. In simple distillation it is important to have a

difference in boiling point of at least 25 degrees Celsius (77 degrees Fahrenheit) in order to

have a successful separation. The compound that has the lower boiling point is known as the

more volatile compound. The mixture is heated to the lower of the two boiling points. Once the

boiling point of the more volatile compound is reached, the more volatile compound will turn

into vapor. That vapor will be condensed back into a liquid as it is collected. Simple distillation is

commonly used in the process of distilling alcoholic beverages. The ethanol has a lower boiling

point than the rest of the fermented solution, so the ethanol can be separated easily.

Fractional distillation is a very similar process when compared to simple distillation.

Fractional distillation uses a fractionating column that is filled with glass or plastic beads. The

fractionating column allows for better separation because the beads allow the compound to

repeat the process of condensing, re-evaporating, and condensing. This basically repeats the

distillation process multiple times. Fractional distillation results in a purer substance, but takes

much longer to perform and requires more energy when compared to simple distillation.

Another advantage is that more complex mixtures can be distilled using fractional distillation

over simple distillation. Another difference between fraction distillation and simple distillation

is that simple distillation requires a large range in boiling points, while fractional distillation

does not require as large of a range. (Distillation Guide). The process of fractional distillation
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can be used to separate water from salt. This helps purify water from salt or other impurities

into clean, drinking water.

Steam distillation is also very similar to these processes. Steam distillation is commonly

used to separate essential or fragrant oils from compounds. These types of oils can typically be

derived from plants such as the orange oil being obtained in this experiment. The essential or

fragrant oils also typically have a very high boiling point which can make it hard to separate

with simple or fraction distillation. A compound boils when the pressure of the liquid is equal to

the pressure of the atmosphere (gas) pushing down on the compound. Water is added to the

mixture and this lowers the overall boiling point of the oils significantly. This makes it possible

to distill product at a lower temperature. The steam that is formed is collected. Steam

distillation utilizes the concept that the oils are hydrophobic which means the two compounds

obtained will be immiscible and result in two layers. This allows for easy separation of the water

from the desired oil. The objective was to extract orange oil from an orange peel solution

through steam distillation.

To determine the structure and composition of the orange oil several tests can be run.

The bromine test is able to help determine if the compound is saturated or unsaturated. Based

on the reaction following the addition of bromine, it is possible to make a prediction of whether

the compound has only single bonds or has any double or triple bonds. If the orange oil solution

remains clear after the addition of bromine that means that the orange oil solution reacted

with the bromine and has multiple bonds and is not a saturated solution. If the orange oil

solution changes color that means that the orange oil solution was completely saturated and

only had single bonds and did not react with the bromine.
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Infrared light is nonvisible light that has a longer wavelength than visible light. It is on

the opposite side of the spectrum of ultraviolet light. Infrared spectroscopy is used to

determine a molecule, the structure of a molecule, or the purity of a molecule by how the

infrared light interacts with the molecule (IR Spectroscopy Tutorial). To operate the infrared

spectrometer, the test sample must be added first to a clean salt plate. Another clean salt plate

will be added on top of the first one. The two salt plates with the test sample in between will be

added to the IR cell holder. The cell holder will be added to the instrument for testing. The test

is performed by shinning infrared light through the test sample. The structure of the compound

will determine what part of the infrared spectrum is absorbed. This is recorded on a graph that

helps map points that give clues as to the makeup of the molecule.

Gas chromatography is used to determine the purity of a compound and structure as

well as the amount of the sample. The instrument separates the compounds by boiling point

and polarity. The sample is injected and turned into vapor. An inert gas mobile phase carries

the sample through the instrument. The sample interacts with the stationary phase based on

polarity. The objective of these tests were to characterize the colorless liquid that was isolated

by the steam distillation.

III. Procedure: Lab #1

The orange peel needed to be cut into shreds. The shreds of orange peel were weighed at

72.77 g. The orange peel shreds were added along with 225 mL of distilled water to the

blender. The mixture was blended until it was a thick, orange liquid that was uniform in

consistency. Added the blended orange peel solution to the 500 mL round-bottom flask.

Assembled the apparatus and connected hoses for water and gas.
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Condenser

Thermometer

Vacuum adapter
Three way adaptor

Claisen adapter

Collection tube
Round bottom flask

Water in tube
Water out tube

Figure 1: Orange Oil Apparatus

Turned on the water and adjusted until the flow was correct. Turned on gas and lit the

Bunsen burner. Closed fume hood and waited for the solution to begin to boil. Several layers

seemed to start to form in the solution. There was a liquid layer on the bottom, thicker middle

layer, and foam forming on top. Added ice to bowl around the graduated cylinder. Collection

tube has mostly water, but thin layer of oil on top. The oil is a transparent, off-white solution.

Once 40 mL of solution had been distilled, the collection tube was removed. The 40 mL oil and

water solution was placed into a separatory funnel so that the water could be removed.
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Transferred the remaining part of the solution by pipette into a tarred vial. Removed as much

water as possible from the tarred vial. Added 12 CaCl2 tablets. The solution stayed

clear/transparent. Measured the vial at 5.50 g. Transferred remaining oil to vial with pipette

and reweighed the vial. Mass obtained was 6.16 g. The masses were subtracted for a total mass

of 0.66 g of orange oil.

IV. Procedure: Lab #2

Bromine Test

Cleaned a dried a test tube with distilled water. Added four drops of the orange oil to

the test tube. Carefully added one drop of bromine to the test tube. This test can be used to

help determine the structure of the orange oil compound. The orange oil remained clear, that

means it is a structure with multiple bonds.

Infrared Spectrum Test

Cleaned both sides and pieces of salt plate with hexane. Added 1 drop of orange oil to

the plate. Placed other plate on top. Added the salt plates with orange oil to the IR instrument

and ran the test. Printed results.

Gas Chromatography

Set up instrument. Added syringe to orange oil, pumped syringe, pulled syringe out with

plug down to keep very little orange oil on the syringe. Added syringe with orange oil on it to

the instrument. Collected data. Printed results.

V. Results:

The original mass of the orange peel was 72.77 g. Before blending the orange peels, 225 mL

were added. Once 40 mL of solution had been collected the collection tube was removed and
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the heating element was turned off. The 40 mL solution was a mixture of the desired orange oil

and water. The oil is hydrophobic, so it is completely immiscible with water. This allowed two

separate layers to form in the collection tube. The mixture of the two liquids was transferred

from the collection tube to a separatory funnel. The orange oil formed the top layer and the

water formed the bottom layer because the oil was less dense than the water. The purpose was

to filter out the water from the oil. The rest was transferred by pipette into a tarred vial. The

remaining water was removed from the tarred vial. The oil stayed transparent/clear. Once all

the water was removed, the remaining oil was transferred to a vial. The empty vial was

weighed and had a mass of 5.50 g. Once adding the orange oil the mass increased to 6.16 g. By

subtracting those two values a total mass of 0.66 g is the final mass of the orange oil collected.

This means that after starting with 72.77 g only 0.66 grams were actually obtained in the form

of orange oil. If the final mass of 0.66 g is divided by the initial mass of 72.77 g the quotient

represents the percent of the oil obtained from the initial solution. The percent of oil obtained

was 0.91% of the initial solution.

The bromine test is used to determine whether a compound is completely saturated or

unsaturated. If a compound is saturated, it will contain only single bonds. If it is unsaturated, it

will contain single bonds along with double or triple bonds. The bromine will not react with a

saturated solution because it is stable. If it remains clear it is because bromine reacted with the

compound. The bromine is able to react with the compound by breaking the multiple bonds.

The orange oil solution used in this lab remained clear which means it was an unsaturated

solution and did not react with the bromine.

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The gas chromatogram shows that there were a total of three compounds in the solution.

Two of the three were impurities that could not be removed from the orange oil. The first

impurity made up 0.013% of the total solution. The second impurity was 0.273% of the total

solution. This means that 0.286% of the solution was impure. Pure orange oil made up the

other 99.715% of the solution.

Table 1: Peak Table

Peak # Ret. Time Area Area%

1 0.565 88716 0.013

2 0.792 1923210 0.273

3 1.474 703357069 99.715

Total 705368995 100.000

The infrared test uses infrared light to help determine what functional groups can be found

in a compound, the bond/appearance, signal intensities, the percent transmittance, and the

absorbance. All absorbances recorded above 1250 cm were added to Table 1. For further

results, refer to the Infrared graph attached separately.

Table 2: Infrared Chart

Absorbance Percent Signal Bond/Appearance Functional group

cm-1 transmittance intensities

3084.23 35% Strong, CH stretch/ Aromatics/Alkenes

Medium =CH stretch

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3072.66 36% Strong, CH stretch/ Aromatics/Alkenes

Medium =CH stretch

3046.62 47% Strong, CH stretch/ Aromatics/Alkenes

Medium =CH stretch

3010.93 30% Strong, CH stretch/ Aromatics/Alkenes

Medium =CH stretch

2964.64 5% Medium CH stretch Alkanes

2918.35 2% Medium CH stretch Alkanes

2856.63 7% Medium CH stretch Alkanes

2834.44 8% Medium HC=O: CH Aldehyde

stretch

1644.34 20% Medium C=C stretch Alkenes

1452.42 18% Medium CH bend/ Alkane/Aromatics

CC stretch (in
ring)
1436.03 10% Medium CC stretch (in Aromatic

ring)

1376.23 25% Medium CH rock Alkane

The essential oil that was distilled was from the orange peel solution was Limonene. This

was proven from the multiple tests that were performed. The bromine test proved that it was

an unsaturated solution. The gas chromatography proved that the solution was 99.715% pure.
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Finally, after comparing Limonene to the Infrared test, it is possible to see that the functional

groups match up as seen in the figure below.

Figure 2: Limonene

The sample contained 88.16% carbon and 11.85% hydrogen. These values can be used to

find the empirical formula. The percentages must be assumed as the mass. Then both carbon

and hydrogen must be converted to moles. There are less moles of carbon (7.34 moles) than

hydrogen (11.76 moles). Divide each value by the lowest number of moles. That leaves carbon

at 1.0 and hydrogen at 1.6. Both must be whole numbers so they are both multiplied by 5. The

empirical formula ends up being C5H8 at a mass of 68 g/mol. It was discovered that the

molecular weight of limonene is 136 g/m. This mass is double the mass of the mass used for the

empirical formula. In conclusion, molecular formula for limonene is C10H16.

VI. Discussion:

Steam distillation is the most reasonable choice for extracting essential oils for several

reasons. By using steam distillation, the pressure in the flask is lowered, which lowers the

boiling point of the essential oil that is being distilled. This is beneficial because that way not as

much heat is needed. A second advantage relates to the first. Organic compounds can
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decompose when exposed to heat. If high amounts of heat were needed, the organic

compounds would have a better possibility of decomposing and being destroyed. Fortunately,

since the operation can be run at a lower temperature, the organic compounds are not at as

high of a risk. The disadvantage is there is not a high yield amount from this process. The yield

was very pure, however, less than 1% was recovered from the initial mass.

The tapered test tube played an important role in the final extraction of water. The basic

concept of the tapered test tube is that has a normal diameter at the top, but tapers down to a

smaller diameter at the bottom. When the mixture of oil and water was added to the tapered

test tube, the water was denser, so it went to the bottom and the oil stayed on top. The water

was in the in the tapered portion of the test tube which allowed for a more accurate extraction

of the water. This allows for much greater accuracy than using solely the separatory funnel.

The calcium chloride(CaCl2) was added as a drying agent. The calcium chloride was

added after the water was extracted from the tapered test tube. At that point there should

have been very little water left in the tapered test tube. The calcium chloride was added to

remove any remaining water. Once it absorbed the water, it was removed from the remaining

oil. This step is very important when it comes to the purity of the substance.

There are four different functional groups indicated by analyzing the infrared spectrum.

In the range of 3084.23 cm-1-3010.93 cm-1 the functional groups aromatics (CH stretch) and

alkenes (=CH stretch) are present. The next range marked on the graph was 2964.64 cm-1-

2856.63 cm-1. The functional group in this range is known as alkanes (CH stretch). The

following range is at 2834.44 cm-1 and represents aldehydes (HC=O: CH stretch). After that

range is 1644.34 cm-1. This range also falls under the alkane range (C=C stretch). Next on the
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list is 1452.42 cm-1 which falls under two function groups. These groups are alkane (CH bend)

and aromatic (CC stretch (inring)). The following functional group is aromatic (CC stretch

(inring)) and is at 1436.03 cm-1. The last measurement above the 1250 cm-1 mark is 1376.23

cm-1 and represents the function group alkane (CH rock).

The empirical formula was possible to determine through elemental analysis. The

essential oil was comprised of 88.16% carbon and 11.84% hydrogen. These values can be used

to determine the empirical formula. Refer to paragraph six of results to find the calculation of

the empirical formula. The empirical formula can be useful, but cannot always be a true

indicator of the molecular formula. The mass spectroscopy is what was used to determine the

mass of the molecule of limonene. The mass was 136 g which is double the mass of the mass

found from the empirical formula. This means that the molecular formula is double the

empirical formula. The empirical formula was C5H8 and the molecular formula is C10H16. Refer to

paragraph six of results to find the calculations for the molecular formula.

Conclusion:

Steam distillation was the optimal type of distillation to use for this lab because the

objective was to extract orange oil. It is the best choice because it can operate at a lower

temperature so the chance of decomposing the organic material is decreased. The lab started

with 72.77 g of orange peels. After the extraction, 40.0 mL of a water/oil mixture was obtained.

This mixture was separated through several techniques such as using a separatory funnel and a

tapered test tube. The final mass of oil obtained was 0.66 g. This was 0.91% of the initial mass.

Through gas chromatography it was possible to test the purity and the orange oil was 97.715%

pure. The bromine test proved that the solution was not saturated and contained double or
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triple bonds. Elemental analysis made it possible to calculate the empirical formula which was

found to be C5H8. Mass spectroscopy gave access to the molecular weight of the orange oil

which was 136 g/mol. This made it possible to determine the molecular formula which was

double the empirical formula (C10H16). Infrared spectroscopy helped determine which

functional groups were present in the molecule. It was found that four different functional

groups were found. These functional groups were alkanes, alkenes, aromatics and aldehydes.

By combining all of these tests it was determined that the orange oil molecule was limonene.
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Work Cited

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<http://orgchem.colorado.edu/Spectroscopy/irtutor/tutorial.html>.

"Laboratory Help! Distillation." Laboratory Help! Distillation. N.p., n.d. Web. 03 Apr. 2016.

<http://www.chemhelper.com/distillation.html>.

"What Is Gas Chromatography." What Is Gas Chromatography. N.p., n.d. Web. 03 Apr. 2016.

<https://www.chem.agilent.com/cag/cabu/whatisgc.htm>.