Recrystallization Techniques

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1 Adapted from: Recrystallization Techniques The Purity and Purification of Solids, CHEM 337M Laboratory Manual; Portland State University, Portland, OR, Prelab Assignment Read Ch. 13 (all) in your Survival Guide Write your lab notebook prelab. Find and draw the structure of adipic acid, and determine the molecular weight. Look up physical data for adipic acid and your recrystallization solvent(s). Also, give any disposal or hazard information as necessary. Be sure to cite your sources for any physical data. As this experiment does not involve the direct synthesis of any molecule, you will not need to determine the number of moles of the reagents or the theoretical yield. When finally determining your recovery yield, assume that the adipic acid mixture that you were given was 85% pure (e.g. if you start with g of the mixture, 0.85 g was adipic acid). Introduction You have now encountered the use of melting behavior as an indicator of purity of a solid. If you find that your solid is impure by melting point, how can you rectify this? This lab will show you an important technique for purifying solids that are not pure, called recrystallization. You will routinely recrystallize any solid product obtained in the labs that your perform this year. Your goal for this lab is to learn the technique so that you can use it whenever you need it without a specific set of directions. An effective crystallization is one in which: 1) a high degree of purity is achieved and 2) a maximum amount of compound is recovered. Recrystallization has a basic limitation in that it is generally effective if substances are mostly pure, meaning that there is one primary component. A mixture containing several major components can t be purified by recrystallization, but there are other techniques for those separations to which you will be introduced later in the year. The Basic Technique This method relies on the fact that most solids are more soluble in a hot solvent than they are in the same amount of solvent at a lower temperature. The following outlines the basic procedure: 1. The solid sample is placed in a container, generally an Erlenmeyer flask (not a beaker!) because it contains hot vapors more effectively, prevents surface cooling of the solution, and can be swirled without splashing the sample. Enough unheated solvent is added to the solid to make a slurry. It is not necessary to note the exact amount of solvent used. At this stage you do not want your compound to dissolve! You want much less solvent than eventually needed to dissolve the compound hot. 2. The slurry is placed on a hot plate and the solvent is brought to a boil with continuous swirling. Typically, some solid will remain undissolved because not enough solvent is present at this stage. You should also begin to heat a small amount (5-10 ml max) of pure recrystallization solvent in a separate erlenmeyer flask, which you will need in future steps. 3. Small portions of the solvent are then added to the hot mixture while the solution is swirled and kept boiling. Addition of small portions of solvent is continued until all of the solid dissolves, giving a little time between addition to allow for the dissolution process to take place. This procedure creates a hot saturated solution of the sample. Recrystallization Techniques Fall 2007 Page 1 of 5

2 4. The solution is set aside to cool slowly. At lower temperatures, the solvent can no longer dissolve as much sample, so the solid begins to crystallize. The solid crystallizes as a pure compound; the impurities remain soluble in the solvent as they are at a much smaller concentration. 5. The crystals of the pure substance are separated from the supernatant solution (also called the mother liquor ) by vacuum filtration, washed with a little cold solvent, and then allowed to dry. The impurities are carried off in the mother liquor, which is now called the filtrate. Add solvent to make a slurry Heat to boiling O X O OO OO X X O O O O X O = desired compound X = impurity Some solid still present Small amounts of solvent are added Continue heating O O Cool Most/all of the solid has dissolved pure crystals O O O To vacuum filtrate (should include impurities) filter and wash Pure crystals form, impurities stay dissolved OOO OOOO To summarize, a hot saturated solution of the sample is prepare as indicated above by using only enough solvent to dissolve the sample at the boiling point of the solution. When the solution is cooled the pure major component separates as crystals because it is not as soluble at lower temperatures. Impurities do not crystallize because they are present in relatively small amounts to begin with. Note that a small amount of the desired sample will still be soluble in the cold solvent, so that some sample loss is inevitable. To minimize this, we often chill the recrystallization mixture on ice before filtration. Variations Sometimes the overall process involves additional steps as needed. They are only carried out when necessary because they usually lead to further material losses. Insoluble Impurities Hot Gravity Filtration If the sample contains debris or other extremely insoluble material, such as insoluble salts, bits of paper, boiling chips, (sometimes called mechanical impurities) these have to be separated from the hot solution or it will recontaminate the recrystallized sample. Insoluble impurities are removed by filtering the hot solution through fluted filter paper such that the contact between the filter paper and walls of the funnel is minimized and filtration is rapid. Rapid filtration is necessary to prevent the desired product from crystallizing prematurely. The filtered solution is then set aside to cool and form crystals as before. A hot filtration is performed only if insoluble impurities are present, and the solution cannot be readily decanted away from the impurities. Recrystallization Techniques Fall 2007 Page 2 of 5

3 Colored Impurities Trace amounts of highly colored substance are frequently observed to contaminate organic substances. These impurities are not totally removed in an ordinary recrystallization, but they can often be removed by adding activated charcoal to the hot solution, followed by a hot filtration to remove the charcoal. The activated charcoal absorbs organic compounds on to its surface, and they are removed with the charcoal. This leads to removing the colored impurities, but also to product loss, so the use of activated charcoal is used only when highly-colored impurities are present. The amount of charcoal used should be about 1 5% of the weight of the sample being recrystallized. Recrystallization Techniques Fall 2007 Page 3 of 5

4 EXPERIMENTAL PROCEDURE Note: The procedure below contains an unrealistic feature of most recrystallizations the amount of solvent is specified. Normally, you would use an unspecified minimal amount as described in the introduction. However, when you are first learning the technique, some assistance is good! Your goal for this experiment is to learn the recrystallization technique. You and your partner will perform two different trials, one using activated charcoal and one without. With each recrystallization, try to obtain the maximum yield of recovered product with the highest purity, as shown through a narrow melting point range. The general procedure will be listed first, in its entirety, and then specific instructions for the two recrystallizations will be given. General Recrystallization Procedure 1. Be prepared! Assemble solvents, glassware, charcoal and equipment needed through the hot filtration step. You do not want your sample either cooking on the hot plate or cooling on the countertop while you are assembling materials. 2. Place the impure solid in an Erlenmeyer flask. Add solvent to cover the solid and to make a slurry. If you anticipate a hot filtration, you may add a few boiling chips. 3. On a hot plate, heat to a gentle boil with swirling and stirring. 4. With continued heating, add small amounts of hot solvent until all of the sample is dissolved. Swirl the sample frequently during this operation. Once it has dissolved, add a little (< 1 ml) extra solvent. 5. Remove the flask from the heat and swirl until the solution is a little below its boiling point. Cautiously add a little charcoal and swirl again. If there is no frothing, add the rest of the charcoal and swirl thoroughly. Keep the mixture at or near its boiling point for 2 3 minutes, with swirling. 6. If you need to do a hot filtration, filter the hot liquid through fluted filter paper using a preheated stemless or powder funnel, into a second Erlenmeyer flask. To preheat the set-up, run some hot solvent (1-2 ml) down the filter paper, funnel and flask before performing the filtration. Support the set-up with an iron ring so it does not tip over. 7. Rinse the original flask with some additional hot solvent and run through the filter. 8. Bring the solution back to a gentle boil, with swirling. Heat for a few minutes to evaporate some solvent and concentrate the solution. 9. Set the flask aside to cool to room temperature. During this cooling, initiate crystal formation by scratching the glass in the solution with a spatula, or by adding a seed crystal, if available. 10. Once the mixture has cooled, chill it thoroughly in an ice bath. Also, chill a small amount (~10 ml) fresh solvent in the ice bath to use in later steps. 11. Vacuum filter your crystals, using the cold filtrate to help transfer crystals from the Erlenmeyer flask to the filter. 12. Rinse the flask and wash the crystals with a small portion of the chilled fresh solvent. Use your spatula to spread the crystals out and push solvent out of the crystals. Draw air through the filter cake to dry the crystals. 13. Transfer the crystals (and filter paper, if using a Büchner funnel) to a pre-weighed watch glass, and spread them out to let them dry (usually, overnight). 14. Record the mass of your crystals. Recrystallization Techniques Fall 2007 Page 4 of 5

5 Specific Procedure Without Charcoal: Recrystallize 1.0 g of impure adipic acid from water, starting from step 1 of the General Procedure. Use boiling chips! Use a 50-mL or 125-mL Erlenmeyer flask and a total of 8 ml of solvent by the end of step 4. Omit the charcoal (step 5) and proceed to the hot filtration (step 6). Continue as indicated. Begin the second recrystallization while the first sample is cooling. Use no more than a total of 2 ml of additional solvent for the wash step. With Charcoal Recrystallize a second 1.0 g sample of impure adipic acid as above, using activated charcoal as appropriate. Use about g of charcoal. Do not weigh this out! You can eyeball this small amount on the end of a spatula. Charcoal can work slowly, especially if it is in pellets, so give it time! Determine the yields of both recrystallizations once the samples are completely dry. To determine the % recovery, assume your samples were 85% adipic acid initially. Determine the melting points of both samples. Turn in both samples in sample vials, labeled according to the directions in the syllabus. Clean-up and Waste Disposal All materials used in this experiment are non-hazardous. Liquids can be flushed down the drain with water, and solids can be placed in a waste basket. Clean the funnel by running solvent through it. Clean all glassware with detergent and do a final rinse with distilled water. For your report 1. Organize the data (yours and your partners ) into a results section! Brief tables (one for each recrystallization) that include sample weights, purified sample weights, percent recovery, mp of pure sample, lit. value for the mp, and product descriptions should be included. 2. Write a discussion of the experiment. Be sure to include a discussion of the differences between the two recrystallization techniques which technique resulted in a greater yield of compound? Was this expected? Which technique resulted in a higher purity of compound? How do you know? 3. Answer the questions below. Questions Answer these questions and attach them to the end of your lab report. 1. Suggest why recrystallization is not an effective purification method for a solid that is highly impure (40-50% impurity). 2. Usually the recrystallization mixture is chilled on ice just before vacuum filtration. Why is this advantageous? Can you think of a reason that this may be detrimental? 3. You need to perform a recrystallization using a mixed-solvent system. Which of the following solvents could not be used as solvent pairs for such a crystallization? Explain your selection. a. Hexanes and water b. Chloroform and diethyl ether c. Acetone and methanol 4. Give reasons for each of the following experimental techniques used in crystallization. a. A hot crystallization is not filtered unless absolutely necessary. b. An Erlenmeyer flask containing a hot solution is not tightly stoppered to prevent solvent loss while cooling. c. The suction of a vacuum filtration apparatus is broken before the vacuum is turned off. Recrystallization Techniques Fall 2007 Page 5 of 5

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