Today: Conclusion of Distillation/GC Introduction to Exp.4: Steam Distillation. IR
GC conditions for your EA and EP Analysis:
Sample injection volume: 0.5 mL
GC column: 15 m x 0.53 mm (I.D.) PhMe-silicone stationary phase, Rtx-50 columnInitial oven temperature = 35oC
Initial time = 0.75 min
Temperature ramp = 35oC/min
Final Temperature = 70oC
Final time = 1.0 min
Column head pressure = 20 psi or more (He as Mobile Phase)
Injector Temperature = 225oC
Detector Temperature = 250oC
Detector: thermal conductivity (TCD)
RT Area Type Width Area%
(min)
.210 333265 12.35
.506 1103207 40.88
1.061 1261972 46.77
EA
EP
solventGC Chromatogram
AEA/ AEP = nEA/nEP
Area ratio = mole ratio
Task:
Determine the amount of EA as mole % EA in sample S1 and also in sample F1
Step 1: analyze the standard mixture (50:50 v/v) of EA and EP for calibration of the GC instrument
AEA = nEA x C
AEP nEP
where k = 1C
A = GC peak Area
n = molescalculate
Step 2: Calculate the mole ratio of your sample
using the correction factor obtained from the standard
for samples S1 and F1 nEA
nEP
k x AEA
AEP
=nEA
nEP
Mole ratio → mole fraction → mole %
Exp. 4: Isolation of a Natural Product
EugenolCH2CH CH2
HO
CH3O
CH3
H2C
CH3
CH3
CH2CH CH2
CH3C-O
CH3O
O
Caryophyllene
Eugenol Acetate
A “phenolic”.
Steam Distillation 1. What types of mixtures can be separated
by steam distillation?
2. The vapor pressure of water at 99oC is 733 torr. What is the vapor pressure of eugenol that codistills at this temperature?
3. During a steam distillation the mole ratio of two immiscible liquids is equal to the ratio of ...... ?
n1/n2 = Po1/Po
2
Steam Distillation
Dalton’s Law:P1V1 = n1RT1 and P2V2 = n2RT2
V1 = V2 and T1 = T2 n = moles,
P1V1 = n1RT1 therefore n1 = P1
P2V2 n2RT2 n2 P2
where 1= water and 2 =compound steam-distilled
Steam Distillation
n1/n2 = Po1/Po
2
(mass1/MW1) / (mass2/MW2) = Po1/Po
2
Steam distillation problem:
Benzene and water mixture boils at 69oC. The MW of benzene is 78.11. MW of water is 18.01
How many grams of water are required to steam distil 1 gram of benzene?
Steam Distillation Which of the following boiling points
are EQUAL TO 100 degrees C, which are BELOW, and which are ABOVE ?
1. A water - eugenol mixture
2. A water- acetic acid mixture (bp. of pure acetic acid: 120 degrees C; it is miscible with water)
3. A sand-water mixture
4. A solution of NaCl in water
Direct Steam Distillation Set-up
water
150 mL water & 7g Clove buds H2O
Ice bath
Use a lab-jackBunsen burner
Separatory Funnel
ThermometerMacro-scale
Liquid-Liquid Extractionof steam distillate with methylene chloride
Which layer is methylene chloride (CH2Cl2)?
Which layer is going to contain the eugenol?
CH2Cl2
Aqu. layer
Liquid-Liquid Extraction
Plug of cotton
Anhydrous Na2SO4
“Tare” 50-mL E-flask with
one boiling chip**
Collect both MeCl layers, then boil off solvent
Infrared Spectroscopy (IR)1) What is the approximate range of wavelengths
visible to humans? And where would you find the range of IR light? How about its energy compared to visible light?
2) What are the "wavenumbers", commonly used in IR to define absorptions?
3) What type of information do we obtain from an IR
spectrum?
4) How can we identify a compound from its IR, e.g. how can we know that we obtained eugenol?
5) How will your IR tell you if your eugenol sample contains impurities?