CHEM 331-Lab

Organic Chemistry

Experiment 1

Distillation: Simple and Fractional

Department of Chemistry - Faculty of Science

Beirut Arab University
Fall 2020-2021
 Aim of the Experiment

Separate a solution of two miscible liquids in

order to obtain a pure solvent by using a
simple distillation technique.

Distillation: Simple and Fractional | Fall 2020-2021 2

 Separation technique

 Many different methods for separation of a mixture, such as:

 filtration,

 extraction,

 distillation,

 centrifugation,….etc.

 Distillation is one of the topic to study in this Lab session.

 Just as recrystallization is used to purify an organic solid, distillation is used to

purify an organic liquid compound.

Distillation: Simple and Fractional | Fall 2020-2021 3

 Purity of a Compound
 A Pure element or compound contains only one substance,
with no other substances mixed in. while, Impure materials
may be mixtures of elements, mixtures of compounds, or
mixtures of elements and compounds.
 Pure liquid compound will have sharp and narrow boiling
point, while Impure liquid compound has a broad and
depressed boiling point because the impurities decrease the
ability of water molecules to become vaporized during boiling,
so, greater amount of heat should be applied, which can be
purified by distillation.
Distillation: Simple and Fractional | Fall 2020-2021 4
 Distillation
Three types of distillation:

Simple Distillation Fractional Distillation Steam Distillation

Both are methods used for separation of

Process which purifies
mixture of a components based on their
temperature-sensitive
boiling point.
materials, such as natural
• For fractional distillation: b.p between
aromatic compounds in
liquids should be less than 25 °C.
the presence of water.
• While Simple distillation: b.p between
liquids should be greater than 25 °C.

Distillation: Simple and Fractional | Fall 2020-2021 5

 Simple Distillation
 Simple distillation is used to separate and retain the solvent from a solution, is based on the principle that the
solvent which is more volatile evaporates first (volatile measures the tendency to vaporize, having the lower boiling
point)
 The solvent that remains in the flask is called the residue.
 The distilled product is called the distillate.
 During the process as heat is applied, the solvent needed to be purified began to boil off and became water vapor
which rose up to the top of the flask.
 The water vapor entered the condenser where cold water from the inlet caused the water to condense and run off
into the receiving flask.

Distillation: Simple and Fractional | Fall 2020-2021 6

 Fractional distillation
 Is used in industrial scale in the separation of liquid air and the refining of crude oil.
 Separation of two liquids based on the principle that one of the liquids is more volatile than the other (has a lower
boiling point and vaporizes first). For example, the boiling point of ethanol is 78° and pure water is 100°. So, As
the mixture of liquids was heated, the vapors rose up the fractionating column and continually condensed and
vaporized, with the lower boiling point liquid (the more volatile one), rising to the higher part of the column, this
liquid condensed first and was collected as the first fraction, the fractionating column is formed of small glass
beads each one will act as simple distillation . The thermometer measures the temperature of the vapor at the top
of the column and indicated what liquid is driven off. When the temperature reaches the boiling point of the
second liquid, that is then distilled into another container.

Distillation: Simple and Fractional | Fall 2020-2021 7

 Applications

 Separation of volatile oil.

 Purification of organic solvent.
 Refining of petroleum products.
 Separation of drug obtained from plant and animal.
 Purification of drug from animal source.
 Separation of crude oil.

Distillation: Simple and Fractional | Fall 2020-2021 8

 Boiling point

 Boiling point is the temperature at which vapor pressure of the

liquid is equals to the atmospheric pressure. That is when liquid
and vapor are in equilibrium (liquids changes to vapor).
 Thus if decreasing atmospheric pressure by evacuating the
system, the boiling point of the liquid increases.
 Similarly when pressurizing the system, the boiling point will
increase.

Distillation: Simple and Fractional | Fall 2020-2021 9

 Distillation steps

 There are three steps involved in the distillation:

1. 2. 3.

Vaporization of liquid Condensation of vapors Collection of distillate

Involves two steps:
1. Evaporation Process of
liquid transforming from
liquid state to gaseous
state due to the increase in
temperature or pressure.
2. Boiling Occurring when
liquid heated to its boiling
point.
Vapors start to condense due to
the low temperature at the
condensation zone. So all the
vapors are converted into liquid
again by cooling, away from the
distillation flask. The temperature
remain constant until all the
molecules of a first liquid
converted into vapors and moves
into the condenser.
When vapors are cooled in a
condenser and change back
into liquid, a pure liquid is
collected which is called the
distillate and is collected in a
new, clean, and dry flask.

Distillation: Simple and Fractional | Fall 2020-2021 10

 Such example
 If an open container is used
Molecules of vapors escape to the atmosphere to be replaced by molecules escaping from liquid.
This process is called evaporation which take place below the boiling point of the liquid.

 If the container is closed system

An equilibrium is reached in which air space above the liquid is saturated with the molecules of the
vapor, the pressure is called vapor pressure (V.p), which is constant at a given temperature and not
affected by atmospheric pressure. We will illustrate two cases:

1. If the liquid have higher V.p at particular temperature, molecules are escaping easily, where the
intermolecular forces between molecules are weak, so, we should not have to supply so much
heat to break them and boil the liquid. So, liquid with higher V.p has lower boiling point.
2. If a liquid has lower V.p, molecules are not escaping easily, strong intermolecular forces, so, we
need to supply much heat. So, liquid with lower V.p has higher boiling point.

Distillation: Simple and Fractional | Fall 2020-2021 11

 Ideal Solution and Raoult’s Law
 Ideal Solution
When two liquids are mixed together it is known as binary mixture. Ideal Solution is binary mixture of liquid
components and there is no change in properties of other substance. Heat is nether evolved nor absorbed
during mixture formation.

 Raoult’s Law
Raoult’s law states that, "the partial vapour pressure of each volatile constituent in an ideal mixture is equal to
vapour pressure of pure constituents multiplied by its mole fraction"

Compound A : PA = P0 A . XA

Partial vapor pressure of a liquid, Vapor pressure of pure  Mole fraction of

which is the pressure of that gas if it substance substance, which is equal
is alone occupied the entire volume to number of mole of
of the original mixture at the same compound A over number
temperature of mole of total
compounds in a mixture.
XA =

Distillation: Simple and Fractional | Fall 2020-2021 12

 Dalton’s Law

 Dalton’s law states that, the total pressure exerted by mixture of

ideal gas may be considered as sum of partial vapour pressure of

each gas (if alone were present and occupied same volume).

P T = PA + P B

PT = P0 A.XA + P0 B.XB

Distillation: Simple and Fractional | Fall 2020-2021 13

 Application of Law

 Application of Law is for component having higher vapour

pressure (lighter component) will be distilled first.

 This principle is used in simple distillation, separation of

volatile liquid from non-volatile liquid. While fractional

distillation used for a mixture of volatile liquids.

Distillation: Simple and Fractional | Fall 2020-2021 14

 Safety Precautions

As in all laboratory exercises:

• Safety glasses, mask, and gloves must be worn at all
times.
• Avoid skin and eye contact with any chemical reagent.
• In case of skin contact, rinse the area with water for
several minutes.
• For eye contact, flush eyes with water and seek
immediate medical advice.

Distillation: Simple and Fractional | Fall 2020-2021 15

 Procedure

Heat gently When the first drop falls into the

receiver record the temperature
(b.p (ethanol) = 78 °C)

25 mL of 96% ethanol + 10 1. Continue heating with rate of 2

mL water + boiling stones drops/min, until all pure ethanol is
(used to regulate collected.
2. Record the volume of pure ethanol
temperature and prevent Attach the apparatus carefully by using a cylinder, should be
bumping) approximately the same used at the
beginning.
3. Record the volume of residue in the
round bottom flask which is related
to water.

Distillation: Simple and Fractional | Fall 2020-2021 16

 Calculation

96 % ethanol is used , which means that:

96 mL ethanol 100 mL
Volume (ethanol) /25 mL solution
??? 25 mL
And,
4 mL water 100 mL
??? 25 mL Total Volume (water) /25 mL solution
+ 10 mL water is added to the mixture.
So, The calculated value should be approximately the same of that
obtained.

Distillation: Simple and Fractional | Fall 2020-2021 17

Distillation: Simple and Fractional | Fall 2020-2021 18