Chem 334

Figure 1 Figure 2

Expt. #3 Simple and Fractional Distillation; Analysis of Distillation Fractions by GC

What factors affect the boiling point of a compound?

Experiment #3 compounds
EA = ethyl acetate

CH3CO2CH2CH3
b.p. = 77oC

EP = ethyl propionate CH3CH2CO2CH2CH3

b.p. = 99oC

Where would you expect the boiling point of a mixture of ethyl acetate and ethyl propionate?

See Techniques 2 and 3

Where would you expect the boiling point of a mixture of ethyl acetate and ethyl propionate?

Boiling Point - Composition for a Liquid-Liquid Mixture

Raoults Law

mixture of two liquids will have a b.p. that is between the b.ps. of the pure liquids
PX = PoXNX where PX is the partial pressure of X PoX is vapor pressure of pure X NX is the mole fraction of X in mixture
(Exception: Azeotropes)

Assume a mixture of

x moles of EA and y moles of EP

What would be the mole ratio?

What would be the mole fraction of EA in the mixture?

Boiling Point - Composition for EA - EP mixture

Total vapor pressure of mixture Ptotal is the sum of the partial pressures due to EA and EP. Ptotal = PEA + PEP If Ptotal is equal to the external pressure,
boiling occurs.

Your experiment:
We will do two distillations: A simple distillation and a fractional distillation.

Work in teams of two: One student sets up the simple distillation and the other student sets up the fractional distillation glassware.

Table for Simple (Fractional) Distillation

Temp oC # drops 1 Record your data: Temp. & # drops

4
8 Also collect data for Fractional Distillation

12

70 etc.

Simple Distillation Set-up

Thermometer position

collect the 1st two drops here, in a receiving vial.

Label!
*

Figure 1

Add boiling chip

Continue recording your data

Fractional Distillation Set-up

Micro-column & steel sponge

Be careful not to cut your hand with the steel sponge when packing the column. *

Do not stuff the column too tightly

Figure 2

Simple & Fractional Distillation

Plot Both Curves on one Graph

Temperature 98 oC
oC
oC oC

Plot both S1 and F1 curves on the same graph

8 12 16 20 24 28 ..etc. Volume of distillate (# drops)

Part C. Analysis of Distillation Fractions by GC

HP 5890 Gas Chromatograph

Flow Diagram for a Capillary GC

Sample

Injector Carrier Gas

vent

GC Detector

Open Tubular Capillary Column

Gas Chromatography
A separation method for volatile compounds A chromatography method: Stationary phase and moving phase Separation is based on

1) physical & chemical properties of each compound

2) different interaction with the stationary phase

A true microscale method!

Each peak (in a good separation) represents one compound.

Retention time Injection point

Each peak (in a good separation) represents one compound. The area under each peak corresponds to moles of the compound

Gas chromatogram of a 50:50 (v:v) EA/EP mixture

In diethyl ether

EA
EP

Remember: Diethyl ether Petroleum ether !!!

Next time:
Gas chromatography (conclusion) Steam distillation: Isolation of eugenol from cloves