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Extraction
A Separation and Isolation Technique

Introduction
Extraction is a physical process by which a substance is transferred from one phase to another, usually from a liquid or a solid to another liquid. The substance is removed from one phase by adding to it an immiscible solvent in which the substance is more soluble.  Solid-liquid extraction is the extraction of a substance from a solid phase (e.g. isolation of caffeine from tea leaves by hot water).  Liquid-liquid extraction is the extraction of a substance from a liquid phase.  Extraction is one of the most common methods of separating: 1- an organic product from a reaction mixture 2- a natural product from a plant.

Liquid-liquid Extraction
Liquid-liquid extraction involves the distribution of a substance between two immiscible liquid phases. The two liquid phases are usually, but not always, an aqueous solution and an organic solvent. Most extraction operations in the organic laboratory are carried out in separatory funnel (Figure 1).

Figure 1: extraction using separatory funnel.

If this is not feasible. Table 1 below shows some organic solvents used in extraction. 3) has a relatively low boiling point so as to be easily removed from the compound after extraction. readily available. 2) be immiscible with the other solvent (usually water). doing multiple extractions can increase the amount of compound extracted. . the organic compound is distributed between two different liquid phases: the organic solvent and water. If a compound has a low KD for a given extraction. 4) extract little or none of the impurities and other compounds present in the mixture.38 • Distribution Coefficient One of the most important properties of the solvent is its solubility for a particular organic compound. 5) be nontoxic. the more efficient the extraction. General Experimental Considerations • Choice of Extraction Solvent Although water is almost always one of the liquids in the liquid-liquid extraction process. The efficiency of extraction will depend upon the solubility of the compound in the two solvents. and inexpensive. The magnitude of KD is an indication of the efficiency of extraction: The larger the value of KD. A good extraction solvent needs five essential features: 1) has high solubility for the organic compound. In an extraction. Table 1: Some common extraction solvents. The ratio of solubilities is called the distribution coefficient (KD). the choice of organic solvent is quite wide. it is better to search for a different organic solvent in which the compound is more soluble in order to do liquid-liquid extraction. nonreactive.

This is particularly useful in breaking up emulsions. it is advisable to saturate the aqueous phase with a salt such as NaCl or Na2CO3.7H2O Important Tips: 1. The stopcock and stopper of the separatory funnel should be greased before use. thus improving their separation. 2) Decreases the solubility of the organic and aqueous phases in each other. or Na2SO4 are some common drying agents. • Drying Agents Since the organic solution has been extracted or washed with aqueous solutions. they form an emulsion. page 1) to release excess pressure which builds up inside.39 • Salting-out To improve the extraction of organic compounds from aqueous mixtures. If the solution is clear and only one layer exists. the hydrated salt is removed from the organic solutions by filtration. 2. If 2 layers appear or if the mixture appears cloudy. Do not vent the separatory funnel towards another person. 3. Anhydrous CaCl 2. 2) Saturating the aqueous layer with a salt. 3) Centrifugation. . the layer is organic. the layer is aqueous. 4. The last traces of water have to be removed by treatment with a drying agent.g. At the end of the drying process. b) Put 1-2 drops from one of the layers onto a watch glass or in a small vial and add several drops of water. The funnel is shaken gently at the beginning and vented periodically through the stopcock (as shown in Figure 1. MgSO4. the two immiscible phases do not separate cleanly into two distinct layers. it will contain some water. If an emulsion still forms one can often break it by: 1) Stirring the mixture gently with a glass rod. Common drying agents are anhydrous inorganic salts which readily take up water to become hydrated (as shown in the equation below). the organic phase becomes clear. MgSO4 + H2O  MgSO4. when alkaline aqueous solutions are extracted with chloroform or dichloromethane). It is advisable to prevent its formation by avoiding vigorous shaking of the layers whenever an emulsion is expected to form (e. 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.. usually the denser solvent will be on the bottom. Never discard any layer until the experiment has been completed! 5. • Emulsion In certain cases. This phenomenon which is called saltingout has the following effects: 1) Decreases the solubility of organic compounds in the saturated aqueous phase. When dry. instead.

40 Objective Extract Caffeine from a soft drink. tea. i. i.e. Consult your TA or instructor if you have any doubts. its ability to be protonated by an acid. and their preferred solubility at each stage. Overview Caffeine (1) is a naturally occurring stimulant that has come to play an important role in Western culture: it is present in significant quantities in coffee. an ionic compound with high solubility in water. and a variety of pharmaceuticals. The extraction process exploits the basicity of caffeine. removes the proton and the neutral caffeine will then dissolve in an organic solvent. to achieve separation. soft drinks.e. Once protonated the caffeine core becomes polar (i. Since these two materials have very different polarities it is possible to isolate them in relatively pure form by a series of extractions. Extract Caffeine from tea. The sodium salt of benzoic acid (2) is used as a preservative in foodstuffs. including soft drinks. Such treatment generates the sodium salt. Benzoic acid is soluble in organic solvents when in its neutral form but becomes water soluble when treated with a base. the forms that they can adopt when treated with various reagents.e. treatment with a base. charged) and water soluble. Reversal of the treatment. The purity of the isolated materials can be checked by TLC analysis against pure samples of each of the substances. O H3C O N N CH3 1: Caffeine 2: Sodium salt of Benzoic Acid CH3 N H N O O Na + . A flowchart is given overleaf that details these compounds. Check the flowchart very carefully before beginning the experiment to ensure that you know where you expect the two materials to be at the various stages of the experiment.

41 .

 Transfer 200 mL of a soft drink to a large Erlenmeyer flask and test its pH with one of the papers provided. DCM) has a higher density than water and will form the lower layer in your extraction. Put the aqueous layer to one side. Pour the now basic solution into a large separatory funnel and add 50 mL of DCM. Now gently swirl the two layers for around 5 minutes in the funnel (care! if shaken too vigorously an emulsion can form. Figure 2: Rotatory evaporator . According to your TA assignment.e. Na2CO3 solution until the pH is basic (i. The solvent will now be removed using a rotary evaporator to leave the caffeine (Figure 2). The organic extracts are now "dried" with anhydrous sodium sulfate (Na2SO4). Return the (upper) aqueous layer to the funnel and extract it with an additional 50 mL of DCM using the same swirling procedure. Let the flask stand for a few minutes. Record the weight obtained by subtracting the weight of the caffeine filled flask from that of the empty flask.42 The Experiment Note: Methylene chloride (or dichloromethane. Weigh an empty dry round bottom flask then decant the DCM into it. Collect the two layers in separate Erlenmeyer flasks. The drying agent is added as a solid to the organic solution in an Erlenmeyer flask and the contents swirled with continued addition of the drying agent until the solution is clear. Separate the two layers and combine the organic layers from the two extractions. Add the aq. you have to conduct one of the following experiments. >7). a special piece of equipment that your instructor or TA will demonstrate. Na2CO3 solution dropwise at first to keep any frothing under control—as the neutralization reaction progresses it should be possible to add it a few mLs at a time. Add small portions of 5% aq. which takes a very long time to separate). Return the separatory funnel to the stand and allow the two layers to separate.

Weigh an empty dry round bottom flask then decant the DCM into it. The solvent will now be removed using a rotary evaporator to leave the caffeine (Figure 2). Dry the combined organic extracts with anhydrous sodium sulfate (Na2SO4) until the solution is clear. Transfer the dark solution to a separatory funnel and extract twice with 25 mL portions of DCM. a special piece of equipment that your instructor or TA will demonstrate. Place them in a 600 mL beaker.43  You will be provided with 4 tea bags. After each extraction drain the denser DCM layer into a small flask. Avoid vigorous shaking of the funnel since emulsions may form readily. and boil the mixture gently for about 20 minutes. add about 10 g of sodium carbonate (Na2CO3) and 150 mL of water. rock the funnel gently several times. Record the weight obtained by subtracting the weight of the caffeine filled flask from that of the empty flask. instead. . Cool the dark brown aqueous solution to room temperature and squeeze the tea bags to extract the liquid fully before discarding the bags.

44 Extraction Report Sheet  Isolation of Caffeine from Soft Drink: Volume of soft drink: Mass of extracted caffeine: Amount of caffeine in soft drink (g/mL):  Isolation of Caffeine from Tea Leaves: Mass of tea leaves: Mass of extracted caffeine: Percentage of caffeine in tea leaves: Name: ------------------------- Questions: 1. What property of an organic solvent determines the position of the immiscible layer it forms with water? B). CH2Cl2.Dichloromethane. 2. A). 3.Hexane.Diethyl ether. When the following solvents are used for extracting an organic compound from an aqueous solution. will the organic solution form the upper or lower layer: 1. ------------------------------------------------------------- .

. What is the role of each of the following the extraction process? 1) 12NaCl 2) Anhydrous Na2SO4 3. 50 mL diethyl ether. A solute of A has a distribution coefficient (KD)= 2 between diethyl ether and water. II. If 5.0 g of A are dissolved in 100 mL of water. Twice with 25 mL diethyl ether for each one.45 2. calculate the mass of A extracted with: I.

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