EXPERIMENT 3

Objectives
- isolate and purify caffeine from tea leaves

Extraction of Caffeine From Tea Leaves

A. R. M. Salcedo

- characterize the caffeine extracted from tea leaves

- calculate the percent yield of caffeine

A. R. M. Salcedo

Highlighted Concepts
Tea Leaves
Genus: Camellia Species: C. sinensis Binomial name: Camellia sinensis - a small shrub about 3 to 6 feet tall - flowers with small white blossoms that have a delightful scent during fall - likes well-drained, sandy soil that is on the acidic side

Highlighted Concepts
Types of Tea

Green tea

Black tea

Oolong tea
A. R. M. Salcedo A. R. M. Salcedo

White tea

Highlighted Concepts
Components of Tea Leaves

Highlighted Concepts
Caffeine
- is an alkaloid belonging to methylxanthine family
O O

Cellulose the major structural material of all plants Caffeine one of the major water-soluble substances present in tea leaves Tannins high molecular weight, water-soluble compounds that are responsible for the color of tea Flavonoid pigments a naturally occurring water-soluble phenolic compound belonging to a large group that includes many plant pigments Chlorophyll the green pigment in plants that captures the light energy required for photosynthesis

HO

O N N

N N
N N nicotine

O
O N

N
HO H morphine

O caffeine

cocaine

Structures of common alkaloids Structures of common alkaloids

A. R. M. Salcedo

A. R. M. Salcedo

Highlighted Concepts
Caffeine
- is an alkaloid belonging to methylxanthine family
O N N

Highlighted Concepts
Caffeine
Systematic name: 1,3,7-trimethyl-1H- purine2,6(3H,7H)-dione
O HN
NH O N

Other name: 1,3,7-trimethylxanthine 1,3,7-trimethyl-2,6-dioxopurine

N

O HN O N N N

O N N

O
N N

Molecular formula: C8H10N4O2 Molecular mass: 191.19 g/mol Melting point: 237C Boiling point: 178C

N N

xanthine

caffeine

theophylline

theobromine

Xanthine and its Derivatives Xanthine and its Derivatives

A. R. M. Salcedo

Solubility in water: slightly soluble

A. R. M. Salcedo

Highlighted Concepts
Caffeine
- increases the blood pressure - stimulates the central nervous system - promotes urine formation - stimulates the action of the heart and lungs

Methodology
Materials and Apparatus
separatory funnel separatory funnel bunsen burner bunsen burner beaker beaker tripod tripod wire gauze wire gauze cold finger set up cold finger set up vial vial

Reagents
tea leaves tea leaves CH2Cl2 CH2Cl2 NaOH NaOH anhydrous Na2SO4 anhydrous Na2SO4

Uses:
- treats migraine - increases the potency of analgesics - relieves asthma attacks
A. R. M. Salcedo

A. R. M. Salcedo

Methodology
Solid- Liquid Extraction

Methodology
Liquid-Liquid Extraction
Upper layer Upper layer Upper layer Upper layer Upper layer Upper layer

+ 20 mL + hot H2O filter CH2Cl2

+ 20 mL CH2Cl2

+ 20 mL CH2Cl2

Lower layer Lower layer Residue Residue Filtrate Filtrate For liquid-liquid liquidextraction
A. R. M. Salcedo A. R. M. Salcedo

Lower layer Lower layer

Lower layer Lower layer

Lower layer

Methodology
Washing & Drying
Lower layer
Anhydrous Na2SO4

Methodology
Sublimation

Lower layer

+ 15 mL NaOH decant

Crude Caffeine

Upper layer

Hydrated Na2SO4

Dried DCM layer

Evaporate to dryness

Crude Caffeine
A. R. M. Salcedo A. R. M. Salcedo

Methodology
Sublimation
Cork/stopper Rubber bulb

Data and Results

NOTES: NOTES: make sure that the cork is properly make sure that the cork is properly installed installed avoid opening the sublimation tube avoid opening the sublimation tube so as to maintain the pressure inside so as to maintain the pressure inside
Brand of tea leaves Weight of tea leaves Volume of DCM Weight of vial Weight of vial + sublimate

Get the weight of the tea leaves Get the weight of the purified
caffeine

Compute the percent caffeine in the

sample tea leaves Weight of sublimate

Test tube filled with ice (cold finger)

avoid melting the solid during avoid melting the solid during heating heating cold finger should always be cold cold finger should always be cold stop when the sample become stop when the sample become brown or black brown or black

Weight of sublimate Percent caffeine Appearance of caffeine crude pure

A. R. M. Salcedo

% caffeine =

Weight of tea leaves

X 100

Sample

be careful in removing the cold be careful in removing the cold finger (crystals formed on the test finger (crystals formed on the test tube can be easily knocked off) tube can be easily knocked off)

A. R. M. Salcedo

Discussion
Extraction
- the method of separating a substance from a mixture by dissolving
one or more of the components in a solvent

Discussion
Flow chart of separation of caffeine from tea leaves
cellulose caffeine chlorophyll tannins flavonoids Extraction with H2O (100C)

Types: Types:
Liquid-Liquid Liquid-Liquid Solid-Liquid Solid-Liquid

Solvents for extraction: Solvents for extraction:

H2O insoluble Extracted leaves cellulose

H2O soluble Aqueous tea solution

Non-toxic Non-toxic Easily removed Easily removed Desired constituent is soluble Desired constituent is soluble Non-reactive Non-reactive

caffeine chlorophyll tannins flavonoids

A. R. M. Salcedo

A. R. M. Salcedo

Discussion
Flow chart of extraction of caffeine from tea leaves
caffeine chlorophyll tannins flavonoids
Extraction with CH2Cl2 CH2Cl2 solution Aqueous solution chlorophyll tannins flavonoids

Discussion
Liquid-Liquid Extraction
is use for separation of complex mixtures by selective partitioning between two phases, between two immiscible liquids.

AQUEOUS EXTRACT Hydolyzable tannins Non-hydrolyzable tannins Flavonoids Chlorophyll

DCM EXTRACT Caffeine Impurities of chlorophylls and tannins

caffeine
impurities of tannins and chlorophyll

caffeine
Evaporate CH2Cl2
A. R. M. Salcedo

impurities of tannins and chlorophyll

A. R. M. Salcedo

Discussion
Distribution Coefficient
- ratio of the concentrations of the solute in each solvent at a particular temperature

Discussion
Distribution Coefficient
Co = x Vo
Where x is the amount of solute extracted by the extracting solvent Vo is the volume of the organic solvent

- it is independent of the total concentration and the actual amounts of the two solvents mixed KD = Co Cw

KD =

Co Cw G -x Vw
Where G is the original amount of solute Vw is the volume of water

Cw =

where Co is the concentration of solute in the extracted solvent (organic) Cw is the concentration of solute in the original solvent (aqueous)

A. R. M. Salcedo

A. R. M. Salcedo

EXPERIMENT 1
Sample Problem
An average content of caffeine in each tea bag of a commercial tea is about 0.5 g. Supposed 3 tea bags were boiled in 100 mL distilled water. How much caffeine will be extracted from the tea extract using 60 mL dichloromethane (DCM)? The distribution coefficient of caffeine between DCM and water is 5.

Discussion
Sublimation
SOLID VAPOR
- used as method for purification if the vapor pressure of the impurities in a solid are significantly lower than that of a solid sample - compounds with high vapor pressure can be sublime at normal atmospheric pressure - compounds that have Pvap 1 mm Hg at room temperature sublime slowly - can be achieved when pressure is reduced - compounds with nonpolar symmetrical structures that have high m.p. but also high Pvap sublime readily

A. R. M. Salcedo

A. R. M. Salcedo

Highlighted Concepts
Sublimation
Advantages:
- no solvent used - removes occluded materials - often faster than recrystallization

EXPERIMENT 1

Disadvantage:
- if imputirties have similar Pvap as sample, separation will be poor

THE END
A. R. M. Salcedo

A. R. M. Salcedo