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BCM624L
csmadarang 2021
OBJECTIVES
1. Differentiate simple and multiple extraction
ALKALOID
ALKALOIDS
• “Natural Product” (secondary metabolite)
• N-containing heterocyclic compounds
• Very weakly polar/Hydrophobic
• Favors solubility in non-polar solvent
O O
HO
O N O O
O N
N N N
N
N
N H
O HO
caffeine nicotine cocaine morphine
CAFFEINE
• Natural Product
• Purine nucleotide metabolite O
• IUPAC Names
• 1,3,7-trimethylxanthine
N
N
• 1,3,7-trimethylpurine-2,6-dione
O
• Health Effects N
• CNS acting N
• Increase BP and RR
• Diuretic caffeine
METHYLXANTHINE FAMILY
O O
N
HN NH
N
O
O N
N
N
N
xanthine theophylline O
O
HN N
N
N
O O
N N
N
N
theobromine caffeine
SOLID – LIQUID EXTRACTION
Tea Leaves
cellulose, chlorophyll, tannins
(gallotannins), flavonoids,
alkaloids (caffeine)
CRUDE CAFFEINE
Chlorophyll, alkaloids (caffeine)
QUANTIFYING THE COMPOUND
KD (solubility coefficient) – ratio of solute in the two solvent
Xorg
Corg Vorg
KD = =
Caq Xaq
Vaq
K D Vorg
Xorg = X0
Vaq + K D Vorg
FORMULA FOR MULTIPLE EXTRACTION
i
Vaq
Xi = X0
K D Vorg + Vaq
Xi = amount left in aqueous layer
X0 = original amount in aqueous layer
Vaq = volume of aqueous layer
Vorg = volume of organic layer
i = number of extractions
100𝑚𝑔
Corg Caffeine was extracted from 10.0 grams of tea leaves
KD = = 2.5𝑚𝐿
Caq 100𝑚𝑙 (containing 0.5% caffeine) by solid-liquid extraction
20𝑚𝑙 using 100.0 ml of water and liquid-liquid extraction
8 (60)
using DCM. Initial tests on the solubility of the caffeine
Xorg =
100𝑚𝑙 + 8 (60)
50𝑚𝑔 on the two solvents require 2.5 ml of DCM and 20.0 ml
of distilled water to completely solubilize 100.0 mg of
caffeine.
2
100 1. Compute for KD
Xi = 50𝑚𝑔
8 (30) + 100 2. How much caffeine can be extracted by single
extraction using 60.0 ml of DCM?
Xi = amount left in aqueous layer 3. How much caffeine can be extracted by two
X0 = original amount in aqueous layer successive extraction using 30.0 ml of DCM per
Vaq = volume of aqueous layer extraction procedure?
Vorg = volume of organic layer
i = number of extractions
End