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Extraction is one of the most common methods of separating an organic product from a reaction mixture or a natural product from a plant.
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2. Liquid/Liquid extraction
3. Acid/Base extraction
1. Solid/Liquid extraction
Soxhlet extractor
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Steeping a cup of tea: the hot water dissolves the flavoring and caffeine from the tea bag or tea leaves.
2. Liquid/Liquid extraction
In liquid-liquid extraction, equilibrium concentrations of a solute are established between two immiscible solvents.
Extraction is commonly used to separate an organic product from a reaction mixture containing water-soluble impurities.
Distribution Coefficient 32
concentration in solvent2 K= concentration in solvent1 g compound per mL solvent2 g compound per mL solvent1
K=
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Table. Extraction solvents solvent Density (g/mL) Petroleum 40-60 0.64 ether hexane 69 0.66 Ethyl ether 35 0.71 BP
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BP 111o
109o
1.20
1.33
Methylene chloride 40
3. Acid/Base extraction
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Acid/Base extraction
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Acid/Base extraction
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Fig Flow diagram for the separation of a strong acid, a weak acid, a neutral compound, and a base-benzoic acid, phenol, naphthalene, and aniline
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Steps in extraction
1. Preparation of separatory funnel
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2. Adding the liquids Do not fill the s. f. more than three-quarters full
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Solvent density
2. Washing
3. Drying organic solution
4. Removing solvents
5. emulsion (next week)
K = 7.8 at 22 oC
2.0 g caffeine/200 mL tea water
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a/100 (2.0-a)/200
a = 1.59 g (79.5%)
50 mL CH2Cl2 (2X): 88.5 % 33.3 mL CH2Cl2 (3X): 94.5 %
50 mL CH2Cl2 (2x)
K= b/50 (2.0-b)/200
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b = 1.32g
c/50 K= (0.68-c)/200 c = 0.45 g
b + c = 1.77 g (88.5%)
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d=
(91.8%)
25 mL CH2Cl2 (4x)
e= (93.5%)
20 mL CH2Cl2 (5x)
f=
(94.5%)
1. Multiple extraction
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If the organic solvent is less dense than water, the organic solvent will be the top layer.
Drain the lower aqueous layer into a clean flask.
Pour the organic layer out of the top of the separatory funnel into a different clean flask.
If the organic solvent is more dense than water, the organic solvent will be the bottom layer. Drain the lower organic layer into a clean flask. Add fresh solvent to the aqueous layer remaining in the separatory funnel repeat the extraction procedure. Combine the organic extracts.
3. Using one of these methods to determine which layer is the organic layer and which layer is the aqueous layer:
a. Look up the densities of the solvents in the
4. Vent frequently, especially with very volatile solvents such diethyl ether or methylene chloride (CH2Cl2). 5. If the liquid is not draining evenly from the separatory funnel, check to make certain that the stopper has been removed 6. A Teflon stopcock should not be greased. Glass stoppers should not be greases.
7. If there is only one layer in the separatory funnel and there should be two, perhaps the wrong layer was used. Find the correct layer and repeat the extraction. 8. An emulsion is a suspension that prevents a sharp interface between the layers.
2. Washing
The term extraction and washing imply slightly different process, although the mechanics are the same. Extraction is the process of removing a compound of interest from a solution or a solid mixture. Washing, usually means removing impurities from the substance of interest.
2. Washing
Wash (extract with fresh water) to remove any water-soluble impurities. volume: 10 % of organic layer 5 % NaHCO3 or NaCl (Brine, saturated NaCl) Washing is accomplished by placing the organic soln in the S. F. along with the wash solution, then shaking and separating in the usual manner
procedure
Place the solution to be dried in an Erlenmeyer flask. Add a spatula-tip full of the drying agent to the solution. Swirl to suspend the particles.
In the presence of water, the small particles of the drying agent clump together. Continue adding small portions of the drying agent until the solution is completely clear or when additional drying agent is free flowing.
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Table. Common drying agents Drying Acidity Hydrated agent products Molecular neutral sieves MgSO4 neutral MgSO4H2O MgSO47H2O
Acidity neutral
basic
Efficiency Rate very high medium to high low fast fast slow
Rate
2. Exact amounts of drying agent are usually not specified in a procedure. The only way to know for sure how much drying agent to add is by careful addition and observation.
3. Do not add more drying agent than is necessary. The drying agent can adsorb the organic product as well as water.
4. Swirling the drying agent and the solution enhances the speed of the drying. 5. If a liquid dissolves the drying agent, that liquid is probably water. Check to see if the correct layer has been chosen following an extraction. 6. Be aware that different organic solvents absorb differing amounts of eater, so they will require different amounts of drying agent.
4 Acetanilide
H N O
mp:122-123;
mp:111-115
Procedure:
Dissolves with 20 mL EA
Transfer into s. f.
Extract with 10 mL
10% NaHCO3 (3X)
EA layer transfer into a clean and dry E. flask Add anhydrous MgSO4
1 Remove solvent by Rotary Evaporator weigh the RB flask (contain acetanilide) Aq. Soln cooled with ice bath Acidify with conc. HCl (pH < 3) Suction filtration (wash with cold water)
Home work: Search for the method now commonly used to extract caffeine from coffee to manufacture decaffeinated coffee.