CH3 F NH2

-O S SO3- O OH
O N N 3 H
NN NH H
CH3
N N + O-
+ N + O
+ HO O H
+ O
Al3+ O HO H H OH
O CH3
FD&C yellow #6 aluminum lake
O
HN N N
H + H OH OH n

Caffeine
Carnauba Wax Dexterose (glucose) Polyethylene glycol
O
S Al3+
O
D&C yellow #10 aluminum lake Extraction (60 mL DI water + 8 g Na2CO3)
Filtration through glass wool

Aqueous Phase Organic Phase, filtered out

by glass wool

O
CH3 NaO
FD&C yellow #6 aluminum lake H O
O N N H ONa
O H
CH3
N N
+ + + Na
O
n
NaO + ONa
ONa HNaO NaO
+ +
D&C yellow #10 aluminum lake H ONa
O CH3
Trace Amounts of Carnauba Wax

Extraction (7mL dichloromethane)

Organic Phase Aqueous Phase

CH3 Trace Amount Water

O N N CH3 NaO
+ + O N N
FD&C yellow #6 aluminum lake
O
H
H
O H
+ + ONa
CH3
N N Impurities
CH3
N N
+ + + Na
n
NaO
+ ONa
ONa HNaO NaO ONa
O CH3 D&C yellow #10 aluminum lake H
O CH3 Trace Amounts of Carnauba Wax

Trace Amounts of Caffeine

Extraction (7mL dichloromethane)

Organic Phase Aqueous Phase

CH3 CH3 FD&C yellow #6 aluminum lake H NaO ONa

O N N HO
O N N
+
Trace Amount Water

+ CH3 N N
+ + + Na O n
NaO + ONa H
ONa HNaONaO
+ +
N O CH3 H ONa
CH3 N Impurities D&C yellow #10 aluminum lake
O CH3 Trace Amounts Trace Amounts

Extraction (7mL dichloromethane)

Organic Phase Aqueous Phase

CH3 FD&C yellow #6 aluminum lake H NaO ONa

HO
O N N
+ Trace Amount Water
+ + Na O
NaO + ONa H + +
CH3
N N +
Impurities
D&C yellow #10 aluminum lake
n ONa HNaONaO
H ONa
O CH3 Trace Amounts

Drain/Combine Organic Layers Together

CH3
O N N
N
+ Trace Amount Water
+ Impurities

CH3 N
O CH3
Drying Agent (sufficient amount of sodium sulfate or magnesium sulfate)

Filtration via Drying Agent

CH3
O N N

CH3
N N
+ Impurities

O CH3

Evaporation

CH3
O N N
N N
CH3
O CH3

Crude Caffeine (solid)

Recrystallization (12-15 mL acetone + sufficient drops of petroleum ether)

CH3
O N N
N N
CH3
O CH3

Purified Caffeine (solid)