Separation of a Mixture by Extraction: Crystallization

Objectives

Separation of a mixture containing acidic and a neutral compounds extraction. Purification of the solid component crystallization. Identify those components from its spectrum and its melting point.

an by by
IR

Terms

Separation Extraction Crystallization

Separation
Why we need to separate mixture?? To isolate or concentrate components from a mixture. To separate a components from other species that would interfere in the analysis

Methods of Separation

Extraction Crystallization Distillation Chromatography

Extraction

Extraction: Transfer of a solute from one phase to another.

Types of Extraction

Can use most any combination of phases (solid, liquid, gas, supercritical fluid). Solid Liquid - Useful for the isolation and purification of naturally occurring sources.

Extraction

Making coffee is an example for extraction.

Extraction

Liquid Liquid - More common method - Depend on solubility properties of components.

Like dissolves like

So ideally, the extracting solvent should be similar to the solute.

Extraction

We will use two immiscible liquids. - Typically aqueous / organic solvent combos

Extraction

Organic solvents less dense than water. - Diethyl ether, Toluene, Hexane Organic solvents more dense than water. - Dichloromethane, Chloroform and Carbon tetrachloride.

Qualities of the Solvent

Immiscible with other solvent. It should readily dissolve the compound to be extracted. It should dissolve little or none of the unwanted compounds / impurities. Easily separated from the compound. Should not undergo any reaction with the compounds.

Extraction

Extraction

Equilibrium constant for this partitioning is K (partition coefficient or distribution coefficient)

[S]2 K= [S]1

Extraction

Chemically Inert Extraction. Chemically Active Extraction.

Chemically Active Extraction

A reagent that reacts chemically with the substance to be extracted. Solubility property changes after the reaction.

Chemically Active Extraction

COOH

10 % NaOH

Soluble in Diethyl ether & Insoluble in Water

10 % NaOH

COONa

No Reaction & Stay in ether layer

Soluble in Water & Stay in aqueous layer

Chemically Active Extraction

CH2NH2 NO2

10 % HCl

Soluble in Diethyl ether & Insoluble in Water

10 % HCl

CH2NH3+

No Reaction & Stay in ether layer

Soluble in Water & Stay in aqueous layer

Procedure for Todays Lab

Get your unknown mixture. Transfer all your unknown into a 100 mL beaker and find the mass of your unknown. Add 30 mL of diethyl ether, stir slowly to dissolve the mixture. Add 15 mL more of diethyl ether and rinse the beaker.

Procedure for Todays Lab

Add 15 mL of 5 % sodium bicarbonate to the ether solution. Swirl the separatory funnel first and shake gently. Separate the two layers. Repeat these steps two times using fresh 5 % sodium bicarbonate solution. Pool all the aqueous layers i.e. sodium bicarbonate solution

Recovery of Acidic Compound

Cool all the aqueous extracts for about 5 minutes in an ice water bath. Add 3 mL of concentrated hydrochloric acid. Test the acidity of this solution with blue litmus paper (TURN RED). If it is not acidic enough; add 1 mL of acid more.

Recovery of Neutral Compound

Place a small piece of cotton in a dry glass funnel. Keep a fresh and dry Erlenmeyer Flask under the funnel. Add 5g. of anhydrous sodium sulfate over the cotton plug and transfer all the ether layer carefully through the neck.

Recovery of Neutral Compound

Rinse the separatory funnel with 5 mL of ether pour into drying agent. Add few boiling chips and keep on a steam bath. Cork the flask tightly once all the ether has gone.

Recrystallization

Its a technique to purify the solid organic compounds. 1. Slow evaporation 2. Slow cooling 3. Liquid diffusion 4. Use of seed crystal

Recrystallization

Compound to be purified:
1. Moderate or high solubility in hot solvent 2. Low in cold solvent

Impurities: 1. Insoluble in hot solvent or high soluble in

cold solvent.

Easily removed after crystallization. Should not react with substance being purified.

Procedure for Recrystallization

Dissolve all the acidic compound in minimum amount of hot solvent. Filter the solution when it is hot. Slowly cool the solution to room temperature; then keep on ice bath. Filter the crystals, wash it with minimum amount of cold solvent. Allow to dry on its own.

Characterization

Neutral Compound 1. Find the amount of neutral compound you recovered from the mixture. 2. Obtain its IR spectrum. Acidic Compound 1. Calculate the % of recovery. 2. Find its melting point.

Changes

Use Blue Litmus instead of Congo Red.

Notes

Do not forget to add the boiling chips when you evaporate diethyl ether. Vent the separatory funnel very often to relieve the developed pressure.

Caution
NO FLAMES IN LAB TODAY