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Extraction

Liquid-Liquid
Finding the Distribution Coefficient

EXTRACTION Not this painful – Really! .

Purpose • Learn standard extraction techniques • Calculate distribution coefficients • Evaluate extraction efficiency .

Types of Extraction • Solid – Liquid – Very common in every day life • Liquid – Liquid – Very common in organic chemistry lab .

Extraction The Goal – to separate a mixture into its components The Method – differential solubility .

Theory of Liquid – Liquid Extraction • Liquids (solvents) must be immiscible. • Extraction efficiency depends on differential solubility in the two immiscible solvents. density organic product impurity .

Theory of Liquid – Liquid Extraction • Distribution Coefficient solubility in organic solvent (g/100mL) KD = solubility in water (g/100mL) ¾ KD < 1 The substance is mostly in H2O ¾ KD = 1 The substance is mostly in Both ¾ KD > 1 The substance is mostly in Organic .

available. CH3CH2OCH2CH3 ƒ hexane. inexpensive ¾ Density determines top and bottom layer ƒ How can you determine which layer you have if you are confused? ¾ Common extraction solvents ƒ methylene chloride. nonreactive. C6H14 ƒ ethyl acetate. CH2Cl2 ƒ diethyl ether. CH3CO2CH2CH3 .Theory of Liquid – Liquid Extraction ¾ Properties of extraction solvents ƒ high solubility of the organic compound ƒ immiscible with water ƒ relatively low boiling point ƒ nontoxic.

multiple extractions!! . should you use all the solvent in one portion. or should you go with two or three smaller portions? Use smaller.Theory of Liquid – Liquid Extraction • If you have a limited amount of solvent with which to do the extraction and you want to get the maximum amount of product.

¾Separating layers Always remove bottom layer through the bottom Allow time to separate Drain some. ¾ Remove solvent – Isolate extracted compound.Extraction Mechanics ¾Shaking Establish equilibrium concentration of solute between the two immiscible solvents. repeat to get all of the solvent ¾Drying Remove traces of water from organic solvent. ¾Venting Release pressure build-up. .

• Compare the extraction efficiency of smaller and larger volumes given the same total volume Benzoic acid .The Particulars • Determine the distribution coefficient of benzoic acid in methylene chloride.

cool. Let it cool. Reheat. water Let stand Shake water (X) Compound X organic (X) organic water. we'll use an organic solvent that is more dense than water. Use pipet to transfer organic layer organic layer plus drying agent xxxx 5 4 6 xxxx 5 7 4 6 7 3 8 3 8 2 9 2 9 1 11 1 10 dry Erlenmeyer . and reweigh if time allows. organic and X mixed Conical vial Evaporate solvent (low heat) Erlenmeyer + boiling chip (dry and tared) pipet xxxx This is amount of X that originally dissolved in the organic solvent.In this example. So it will be the bottom layer. then weigh it.

059g=0.097g-0.KD Sample Calculation methylene chloride/H2O Initial mass of unknown 0.059g/1.059g Mass of unknown in water 0.9 7mL KD = = 1.6 0.038g/2.97mL Water volume 2.0 5mL .05mL Mass of unknown in solvent 0.097g Solvent volume 1.038g 0.

.0 mmol of benzoic acid to start 1 extraction: 0.Sample Calculation of Kd Suppose you had 5.88 mmol of benzoic acid remained in aqueous layer after extracting 50 mL of benzoic acid aqueous solution with 20 mL of CH2Cl2 .

12 mmol of benzoic acid in CH2Cl2 / 20 mL 0.Sample Calculation of Kd con’t Kd = 4.88 mmol of benzoic acid in water / 50 mL Kd = 11.7 .

Double Extraction Suppose you had 5. .0 mmol of benzoic acid to start 2 extractions: 0. .88 mmol of benzoic acid remained in aqueous layer after extracting 50 mL of benzoic acid aqueous solution with 20 mL of CH2Cl2 in two 10-mL extractions.

55 mmol in CH2Cl2 by both extractions 4.50 .X) mmol in water / 50 mL X = 3.Double Extraction con’t Kd = 11.05 mmol in CH2Cl2 (by 2nd extraction) X + X' = 4.X') mmol in water / 50 mL X' = 1.7 = X mmol in CH2Cl2 / 10 mL (5.0 .50 mmol in CH2Cl2 (end of 1st extraction) Kd = 11.55 mmol in CH2Cl2 compared to 4.7 = X' mmol in CH2Cl2 / 10 mL (1.12 mmol in CH2Cl2 .