LESSON 4: EXTRACTION

Extraction

common separation technique in organic chemistry which is directed at separating the components of a mixture

like dissolves like

Extraction is generally based on the solubility of a particular substance present in a given sample to a specific solvent. Meaning, it follows the concept ______________

Extraction

the transfer of specific solutes from one phase (i.e., solid phase) to another one (i.e., liquid phase)

mixture

PROCESS OF EXTRACTION:

1. There is a __________ of component 1 and component 2.

2. A second solvent is added which is ___________ while water is on the bottom, making an immiscible mixture.

3. The combination is _______________.

4. Allow the mixture to ______________ until 2 layers were formed.

5. Nonpolar component is dissolved in nonpolar solvent while a polar component is dissolved in a polar solvent, proving the concept of ______________.

1 = ?

nonpolar

PROCESS OF EXTRACTION:

1. There is a __________ of component 1 and component 2.

2. A second solvent is added which is ___________ while water is on the bottom, making an immiscible mixture.

3. The combination is _______________.

4. Allow the mixture to ______________ until 2 layers were formed.

5. Nonpolar component is dissolved in nonpolar solvent while a polar component is dissolved in a polar solvent, proving the concept of ______________.

2 = ?

shaken

PROCESS OF EXTRACTION:

1. There is a __________ of component 1 and component 2.

2. A second solvent is added which is ___________ while water is on the bottom, making an immiscible mixture.

3. The combination is _______________.

4. Allow the mixture to ______________ until 2 layers were formed.

5. Nonpolar component is dissolved in nonpolar solvent while a polar component is dissolved in a polar solvent, proving the concept of ______________.

3 = ?

stand

PROCESS OF EXTRACTION:

1. There is a __________ of component 1 and component 2.

2. A second solvent is added which is ___________ while water is on the bottom, making an immiscible mixture.

3. The combination is _______________.

4. Allow the mixture to ______________ until 2 layers were formed.

5. Nonpolar component is dissolved in nonpolar solvent while a polar component is dissolved in a polar solvent, proving the concept of ______________.

4 = ?

like dissolves like

PROCESS OF EXTRACTION:

1. There is a __________ of component 1 and component 2.

2. A second solvent is added which is ___________ while water is on the bottom, making an immiscible mixture.

3. The combination is _______________.

4. Allow the mixture to ______________ until 2 layers were formed.

5. Nonpolar component is dissolved in nonpolar solvent while a polar component is dissolved in a polar solvent, proving the concept of ______________.

5 = ?

functional groups

In extraction, the presence of ________________ aids in the separation process as these groups offers an insight on the polarity of a substance.

hydroxyl, carboxyl, formyl, carbonyl, amino

examples of polar functional groups

Ethanol

semipolar; has polar end (hydroxyl) that makes ethanol soluble in water but it also nonpolar (hydrocarbon part) and soluble in nonpolar substances

less soluble

Longer hydrocarbon chain for alcohol = ?

insoluble

soluble or insoluble in water: octanol

soluble

soluble or insoluble in water: ethanol

soluble

soluble or insoluble in water: methanol

soluble

soluble or insoluble in water: propanol

Simple Extraction

CLASSIFICATION OF EXTRACTION BASED ON NUMBER OF EXTRACTION:

• One-time extraction process using a single solvent to separate components within a given time

Multiple/Repeated Extraction

CLASSIFICATION OF EXTRACTION BASED ON NUMBER OF EXTRACTION:

• Repetitive extraction process where a single solvent is used multiple times to extract more amount of a particular solute. It can also use multiple solvents which enables the process to extract multiple components from a given sample mixture

Solid-Liquid Extraction

CLASSIFICATION OF EXTRACTION BASED ON PHASE:

• Transfer of target solute from a solid phase to a liquid phase

Liquid-Liquid Extraction

CLASSIFICATION OF EXTRACTION BASED ON PHASE:

• A sample mixture is dissolved into two immiscible liquid phases

• Performed in a separator funnel to allow the denser liquid to settle at the bottom part. Components dissolve into the liquid where it has more affinity for.

extraction of caffeine from dried tea leaves into a solution of boiling water

example of solid-liquid extraction

extraction of caffeine by using DCM and water

example of liquid-liquid extraction

High solubility, Non-reactive, Immiscible, Volatile, Non-Toxic

Characteristics of a Good Extracting Solvent

4.4-g anhydrous sodium carbonate

SOLID-LIQUID EXTRACTION PROCESS:

1. Boil tea leaves and ground coffee for 10 min in a previously boiled solution of ________________________ in 100 mL water.

2. After boiling, we have __________________________________.

1 = ?

aqueous extract and separated solid matter

SOLID-LIQUID EXTRACTION PROCESS:

1. Boil tea leaves and ground coffee for 10 min in a previously boiled solution of ________________________ in 100 mL water.

2. After boiling, we have __________________________________.

2 = ?

Anhydrous sodium carbonate

deprotonator of caffeine

Deprotonation

removal of a proton from the structure of caffeine

to make it unionized and more soluble in a non-polar solvent (DCM)

Why was the charge removed from caffeine?

Chlorophyll, Tannins, Gallic acid, Flavonoids, and Alkaloids

components of aqueous extract after the solid-liquid extraction

Cellulose

components of residue after the solid-liquid extraction

aqueous extract

Do aqueous extract or residue proceed to liquid-liquid extract?

beaker as receiver

USING A SEPARATORY FUNNEL DURING LIQUID-LIQUID EXTRACTION:

1. In filling a separatory funnel, the stopcock must be closed and a clean _________ placed under the funnel before any liquids are added to the funnel in case the stopcock leaks or is not completely closed.

specific manner

USING A SEPARATORY FUNNEL DURING LIQUID-LIQUID EXTRACTION:

2. Holding and Using Separatory Funnels. If the contents of the funnel are to be shaken, it is held in a ______________.

intimately as possible; vented

USING A SEPARATORY FUNNEL DURING LIQUID-LIQUID EXTRACTION:

3. Shaking Separatory Funnels. A separatory funnel and its contents should be shaken to mix the immiscible liquids as ________________. The funnel must be __________ every few seconds to avoid the buildup of pressure within the funnel.

Venting

accomplished by inverting the funnel with the stopcock pointing upward and away from you and your neighbors and slowly opening it to release any pressure

aqueous

USING A SEPARATORY FUNNEL DURING LIQUID-LIQUID EXTRACTION:

4. To identify which of the two layers are aqueous and which is organic, add a drop of water and where it goes is the __________ layer.

small traces of water

USING A SEPARATORY FUNNEL DURING LIQUID-LIQUID EXTRACTION:

5. In order to remove these ________________, drying agents or desiccants are used.

REQUIREMENTS FOR DRYING AGENTS (DESICCANTS):

1. neither it nor its hydrolysis product may react __________ with the organic liquid being dried

2. must be _________________ from the dry liquid

3. _________ so that the water is removed in a reasonably short period of time

STEP 5 = ?

chemically

USING A SEPARATORY FUNNEL DURING LIQUID-LIQUID EXTRACTION:

5. In order to remove these ________________, drying agents or desiccants are used.

REQUIREMENTS FOR DRYING AGENTS (DESICCANTS):

1. neither it nor its hydrolysis product may react __________ with the organic liquid being dried

2. must be _________________ from the dry liquid

3. _________ so that the water is removed in a reasonably short period of time

1 = ?

completely and easily removed

USING A SEPARATORY FUNNEL DURING LIQUID-LIQUID EXTRACTION:

5. In order to remove these ________________, drying agents or desiccants are used.

REQUIREMENTS FOR DRYING AGENTS (DESICCANTS):

1. neither it nor its hydrolysis product may react __________ with the organic liquid being dried

2. must be _________________ from the dry liquid

3. _________ so that the water is removed in a reasonably short period of time

2 = ?

efficient

USING A SEPARATORY FUNNEL DURING LIQUID-LIQUID EXTRACTION:

5. In order to remove these ________________, drying agents or desiccants are used.

REQUIREMENTS FOR DRYING AGENTS (DESICCANTS):

1. neither it nor its hydrolysis product may react __________ with the organic liquid being dried

2. must be _________________ from the dry liquid

3. _________ so that the water is removed in a reasonably short period of time

3 = ?

CaCl2, Na2SO4, MgSO4

commonly used drying agents

decantation

USING A SEPARATORY FUNNEL DURING LIQUID-LIQUID EXTRACTION:

6. After the use of a desiccant, separate the liquid portion through ____________.

aqueous extract

LIQUID-LIQUID EXTRACTION PROCESS:

1. Transfer the _____________________ in a separatory funnel.

2. Add ______ (2nd solvent).

3. 2 layers will be formed: aqueous extract that contains ____________________ and the non polar solvent which is DCM.

4. Since ___________ is denser, it is at the bottom.

5. Shaking is done _____ times.

6. After shaking, return it to the setup and allow it to stand for several minutes until it has __________ again.

7. After letting it stand, the aqueous layer contains a._________________ while the organic layer contains b.___________________.

8. Product:______________________

1 = ?

Dicholoromethane

LIQUID-LIQUID EXTRACTION PROCESS:

1. Transfer the _____________________ in a separatory funnel.

2. Add ______ (2nd solvent).

3. 2 layers will be formed: aqueous extract that contains ____________________ and the non polar solvent which is DCM.

4. Since ___________ is denser, it is at the bottom.

5. Shaking is done _____ times.

6. After shaking, return it to the setup and allow it to stand for several minutes until it has __________ again.

7. After letting it stand, the aqueous layer contains a._________________ while the organic layer contains b.___________________.

8. Product:______________________

2 = ?

water and components from samples (tea leaves/ground coffee)

LIQUID-LIQUID EXTRACTION PROCESS:

1. Transfer the _____________________ in a separatory funnel.

2. Add ______ (2nd solvent).

3. 2 layers will be formed: aqueous extract that contains ____________________ and the non polar solvent which is DCM.

4. Since ___________ is denser, it is at the bottom.

5. Shaking is done _____ times.

6. After shaking, return it to the setup and allow it to stand for several minutes until it has __________ again.

7. After letting it stand, the aqueous layer contains a._________________ while the organic layer contains b.___________________.

8. Product:______________________

3 = ?

Dichloromethane

LIQUID-LIQUID EXTRACTION PROCESS:

1. Transfer the _____________________ in a separatory funnel.

2. Add ______ (2nd solvent).

3. 2 layers will be formed: aqueous extract that contains ____________________ and the non polar solvent which is DCM.

4. Since ___________ is denser, it is at the bottom.

5. Shaking is done _____ times.

6. After shaking, return it to the setup and allow it to stand for several minutes until it has __________ again.

7. After letting it stand, the aqueous layer contains a._________________ while the organic layer contains b.___________________.

8. Product:______________________

4 = ?

three

LIQUID-LIQUID EXTRACTION PROCESS:

1. Transfer the _____________________ in a separatory funnel.

2. Add ______ (2nd solvent).

3. 2 layers will be formed: aqueous extract that contains ____________________ and the non polar solvent which is DCM.

4. Since ___________ is denser, it is at the bottom.

5. Shaking is done _____ times.

6. After shaking, return it to the setup and allow it to stand for several minutes until it has __________ again.

7. After letting it stand, the aqueous layer contains a._________________ while the organic layer contains b.___________________.

8. Product:______________________

5 = ?

two layers

LIQUID-LIQUID EXTRACTION PROCESS:

1. Transfer the _____________________ in a separatory funnel.

2. Add ______ (2nd solvent).

3. 2 layers will be formed: aqueous extract that contains ____________________ and the non polar solvent which is DCM.

4. Since ___________ is denser, it is at the bottom.

5. Shaking is done _____ times.

6. After shaking, return it to the setup and allow it to stand for several minutes until it has __________ again.

7. After letting it stand, the aqueous layer contains a._________________ while the organic layer contains b.___________________.

8. Product:______________________

6 = ?

major impurities

LIQUID-LIQUID EXTRACTION PROCESS:

1. Transfer the _____________________ in a separatory funnel.

2. Add ______ (2nd solvent).

3. 2 layers will be formed: aqueous extract that contains ____________________ and the non polar solvent which is DCM.

4. Since ___________ is denser, it is at the bottom.

5. Shaking is done _____ times.

6. After shaking, return it to the setup and allow it to stand for several minutes until it has __________ again.

7. After letting it stand, the aqueous layer contains a._________________ while the organic layer contains b.___________________.

8. Product:______________________

7.a = ?

alkaloid (caffiene)

LIQUID-LIQUID EXTRACTION PROCESS:

1. Transfer the _____________________ in a separatory funnel.

2. Add ______ (2nd solvent).

3. 2 layers will be formed: aqueous extract that contains ____________________ and the non polar solvent which is DCM.

4. Since ___________ is denser, it is at the bottom.

5. Shaking is done _____ times.

6. After shaking, return it to the setup and allow it to stand for several minutes until it has __________ again.

7. After letting it stand, the aqueous layer contains a._________________ while the organic layer contains b.___________________.

8. Product:______________________

7.b = ?

2 extracts of DCM with caffeine

LIQUID-LIQUID EXTRACTION PROCESS:

1. Transfer the _____________________ in a separatory funnel.

2. Add ______ (2nd solvent).

3. 2 layers will be formed: aqueous extract that contains ____________________ and the non polar solvent which is DCM.

4. Since ___________ is denser, it is at the bottom.

5. Shaking is done _____ times.

6. After shaking, return it to the setup and allow it to stand for several minutes until it has __________ again.

7. After letting it stand, the aqueous layer contains a._________________ while the organic layer contains b.___________________.

8. Product:______________________ which will proceed to drying and weighing.

8 = ?

anhydrous sodium sulfate

DRYING AND WEIGHING PROCESS:

1. Add __________________ which is a desiccant/dehydrating/drying agent to remove excess water and remove impurities.

2. To separate drying agent, ____________ the extract in evaporating dish

3. _____________________ until all the DCM evaporated.

4. Collected caffeine will be ___________ to compute the percentage yield.

5. Final product: _______________________ which will be divided into 3 portions for analysis.

1 = ?

decant

DRYING AND WEIGHING PROCESS:

1. Add __________________ which is a desiccant/dehydrating/drying agent to remove excess water and remove impurities.

2. To separate drying agent, ____________ the extract in evaporating dish

3. _____________________ until all the DCM evaporated.

4. Collected caffeine will be ___________ to compute the percentage yield.

5. Final product: _______________________ which will be divided into 3 portions for analysis.

2 = ?

evaporate to dryness

DRYING AND WEIGHING PROCESS:

1. Add __________________ which is a desiccant/dehydrating/drying agent to remove excess water and remove impurities.

2. To separate drying agent, ____________ the extract in evaporating dish

3. _____________________ until all the DCM evaporated.

4. Collected caffeine will be ___________ to compute the percentage yield.

5. Final product: _______________________ which will be divided into 3 portions for analysis.

3 = ?

weighed

DRYING AND WEIGHING PROCESS:

1. Add __________________ which is a desiccant/dehydrating/drying agent to remove excess water and remove impurities.

2. To separate drying agent, ____________ the extract in evaporating dish

3. _____________________ until all the DCM evaporated.

4. Collected caffeine will be ___________ to compute the percentage yield.

5. Final product: _______________________ which will be divided into 3 portions for analysis.

4 = ?

crude extract of caffeine

DRYING AND WEIGHING PROCESS:

1. Add __________________ which is a desiccant/dehydrating/drying agent to remove excess water and remove impurities.

2. To separate drying agent, ____________ the extract in evaporating dish

3. _____________________ until all the DCM evaporated.

4. Collected caffeine will be ___________ to compute the percentage yield.

5. Final product: _______________________ which will be divided into 3 portions for analysis.

5 = ?

khromatos

means color

recording or description

means graphia

principle of chromatography

degree of attractive interaction (affinity) of the dissolved molecules to either the mobile phase or stationary phase used for the separation

Partition Chromatography

• solvent is mobile phase and paper is stationary phase

• Affinity of dissolved molecules (either to solvent or paper) is different, that’s why they’re separated

• Their distance from their point of origin, what they traveled from across the paper, was measured

Chromatography

allows a sample to run through a separation matrix and gravity pulls on the sample downward where it can be separated by size, shape, or charge depending on the resin used

polarity, hydrophobic, ionic interactions, hydrogen bonding, particle size and structure, complementarity

Factors affecting the separation of molecules

resin beads

In column chromatography:

1. The _________ are at the top portion and the sample is on top of this.

2. Upper portion is solvent system which is the _______________.

3. Resin beads are the _________________.

4. Running of sample across the resin beads depends on _____________ of sample with either stationary/mobile phase.

1 = ?

mobile phase

In column chromatography:

1. The _________ are at the top portion and the sample is on top of this.

2. Upper portion is solvent system which is the _______________.

3. Resin beads are the _________________.

4. Running of sample across the resin beads depends on _____________ of sample with either stationary/mobile phase.

2 = ?

stationary phase

In column chromatography:

1. The _________ are at the top portion and the sample is on top of this.

2. Upper portion is solvent system which is the _______________.

3. Resin beads are the _________________.

4. Running of sample across the resin beads depends on _____________ of sample with either stationary/mobile phase.

3 = ?

affinity

In column chromatography:

1. The _________ are at the top portion and the sample is on top of this.

2. Upper portion is solvent system which is the _______________.

3. Resin beads are the _________________.

4. Running of sample across the resin beads depends on _____________ of sample with either stationary/mobile phase.

4 = ?

Stationary Phase

• a layer or coating on the supporting medium (column or planar surface) which interacts with the analytes

• can be solid or liquid

Mobile Phase

• part of the chromatographic system that carries the solutes across the stationary phase

• can be liquid or gas

Normal Phase

TYPES OF CHROMATOGRAPHY BASED ON THE NATURE OF MOBILE/STATIONARY PHASE:

• Stationary phase is POLAR

• Mobile phase is NON-POLAR.

Reverse Phase

TYPES OF CHROMATOGRAPHY BASED ON THE NATURE OF MOBILE/STATIONARY PHASE:

• Stationary phase is NON-POLAR

• Mobile phase is POLAR.

Ascending

TYPES OF CHROMATOGRAPHY BASED ON MOVEMENT DIRECTION OF THE SOLVENT SYSTEM:

• Movement via capillary action of the solvent system

Descending

TYPES OF CHROMATOGRAPHY BASED ON MOVEMENT DIRECTION OF THE SOLVENT SYSTEM:

• Movement is due to the gravitational pull on the solvent system

Isocratic

TYPES OF CHROMATOGRAPHY BASED ON SOLVENT CONCENTRATION:

• Mobile phase has a constant concentration

Gradient

TYPES OF CHROMATOGRAPHY BASED ON SOLVENT CONCENTRATION:

• Mobile phase has a varying concentration

Planar

TYPES OF CHROMATOGRAPHY BASED ON TYPE OF SUPPORT:

• The stationary phase of the process take place on a plane

• e.g., paper and TLC

Column

TYPES OF CHROMATOGRAPHY BASED ON TYPE OF SUPPORT:

• The stationary phase takes place inside a tube like a packed column filled with the entire substance.

Partition

TYPES OF CHROMATOGRAPHY BASED ON MECHANISM OF SEPARATION:

• Particles are separated between liquid mobile and stationary phases

• e.g., paper chromatography

Absorption

TYPES OF CHROMATOGRAPHY BASED ON MECHANISM OF SEPARATION:

• Involves the separation of the components in a mixture based on the interaction of the adsorbate with the adsorbent.

Paper Chromatography

technique used for the separation of compounds based on the differential solubility in the stationary phase and mobile phase (solvent)

Normal

PAPER CHROMATOGRAPHY:

1. Nature of Stationary / Mobile Phase = ?

2. Movement Direction of Solvent System = ?

3. Concentration of Solvent = ?

4. Support = ?

5. Mechanism of Separation = ?

1 = ?

Ascending

PAPER CHROMATOGRAPHY:

1. Nature of Stationary / Mobile Phase = ?

2. Movement Direction of Solvent System = ?

3. Concentration of Solvent = ?

4. Support = ?

5. Mechanism of Separation = ?

2 = ?

Isocratic

PAPER CHROMATOGRAPHY:

1. Nature of Stationary / Mobile Phase = ?

2. Movement Direction of Solvent System = ?

3. Concentration of Solvent = ?

4. Support = ?

5. Mechanism of Separation = ?

3 = ?

Planar

PAPER CHROMATOGRAPHY:

1. Nature of Stationary / Mobile Phase = ?

2. Movement Direction of Solvent System = ?

3. Concentration of Solvent = ?

4. Support = ?

5. Mechanism of Separation = ?

4 = ?

Partition

PAPER CHROMATOGRAPHY:

1. Nature of Stationary / Mobile Phase = ?

2. Movement Direction of Solvent System = ?

3. Concentration of Solvent = ?

4. Support = ?

5. Mechanism of Separation = ?

5 = ?

Stationary phase of paper chromatography

water in the cellulose support (paper)— polar

Mobile phase of paper chromatography

uses different liquid solvents— non-polar

less polar

In paper chromatography, the separation of components is based on their affinity between stationary and mobile phases. With the __________ being the farthest from the origin.

Retention Factor

used to quantify the affinity of a substance to the mobile phase whose values range from 0 to 1.

d spot (distance traveled by solute) / d solvent (distance traveled by solvent)

Rf = ?

Column Chromatography

technique used for the separation of compounds based on the differential partitioning between stationary phase and mobile phase (solvent)

Normal

COLUMN CHROMATOGRAPHY:

1. Nature of Stationary / Mobile Phase = ?

2. Movement Direction of Solvent System = ?

3. Concentration of Solvent = ?

4. Support = ?

5. Mechanism of Separation = ?

1 = ?

descending

COLUMN CHROMATOGRAPHY:

1. Nature of Stationary / Mobile Phase = ?

2. Movement Direction of Solvent System = ?

3. Concentration of Solvent = ?

4. Support = ?

5. Mechanism of Separation = ?

2 = ?

isocratic

COLUMN CHROMATOGRAPHY:

1. Nature of Stationary / Mobile Phase = ?

2. Movement Direction of Solvent System = ?

3. Concentration of Solvent = ?

4. Support = ?

5. Mechanism of Separation = ?

3 = ?

column

COLUMN CHROMATOGRAPHY:

1. Nature of Stationary / Mobile Phase = ?

2. Movement Direction of Solvent System = ?

3. Concentration of Solvent = ?

4. Support = ?

5. Mechanism of Separation = ?

4 = ?

partition

COLUMN CHROMATOGRAPHY:

1. Nature of Stationary / Mobile Phase = ?

2. Movement Direction of Solvent System = ?

3. Concentration of Solvent = ?

4. Support = ?

5. Mechanism of Separation = ?

5 = ?

stationary phase of column chromatography

solid silica in the columnar support— polar

mobile phase of column chromatography

uses different liquid solvents— non-polar

least polar

In column chromatography, the separation of components is based on their affinity between stationary and mobile phases. With the _______ being eluted first.

elute

the process of removing, extracting, or washing the molecule from the stationary phase

eluent

refers to the mobile phase that is used to elute the different components from a sample substance