Experiment 2: Preparation of the Artificial Sweetener Dulcin

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1 Experiment 2: Preparation of the Artificial Sweetener Dulcin Organic compounds known as sugars are carbohydrates that occur widely in nature. For example, sucrose (aka table sugar) is found in sugar can, and fructose is one of the several sugars found in honey. Many people wish to control their intake of sugar, either for health or medical reasons, there is a great demand for artificial sweeteners. Although several different artificial sweeteners are commercially available (e.g. aspartame, saccharin and sucralose), others have been gradually phased out due to undesirable health consequences (e.g. sodium cyclamate). One such artificial sweetener is Dulcin, which is 250 times sweeter than sucrose and whose use is currently phased out in Europe. In this experiment, you will prepare Dulcin [(4-ethoxyphenylurea)] from phenetidine (4- ethoxyaniline) and potassium cyanate (KOCN) in the presence of water and acetic acid (C 3 ), as shown by Equation 1. Under the reaction conditions, potassium cyanate reacts with acetic acid to form the unstable compound isocyanic acid (NCO), as shown in Equation 1a. Because NCO is unstable, it is formed in the reaction mixture (i.e in situ ) and used immediately in the next step. The NCO reacts with phenetidine to give Dulcin (Equation 1b). The acetic acid and water serve an additional role as solvents to dissolve the phenetidine and potassium cyanate. 3 C 2 CO N 2 KOCN, C 3 2 O N N 2 O 1 KOCN + C 3 NCO + C 3 K potassium acetic acid isocyanic potassium 1a cyanate acid acetate N 2 + NCO N N 2 O 1b phenetidine Dulcin

2 Pertinent information about the chemicals you are using: Reagents MW (g/mol) MP (ºC) BP (ºC) Density (g/ml) phenetidine acetic acid potassium cyanate N/A N/A Water Product Dulcin Procedure: 1. Clean the crystallizing dish provided (this is not in your locker and must be returned at the end of the lab period), fill it about half full with hot tap water, and add several boiling stones. Place the crystallizing dish in the center of the hot plate, heat setting to 4. The water must be boiling before being used in Steps 5 and 6, and it may be necessary to increase the hot plate setting to ensure the water is boiling. 2. Add approximately 100 ml of water to a clean 250 ml Erlenmeyer flask and place it on the hot plate next to the crystallization dish. Proceed to begin heating the water to boiling. This water will be used for your recrystallization later in the procedure. 3. To a clean 50 ml Erlenmeyer flask, add 0.5 g of potassium cyanate and 5 ml of hot tap water. 4. Take a clean, dry 125 ml Erlenmeyer flask, place it on the balance and tare it to zero. Using the Pasteur pipette in the reagent bottle, add phenetidine dropwise to the flask to get as close as possible to 0.7 g. In your notebook, record the actual mass of phenetidine used. Then add 10 ml of hot tap water and 1 ml of acetic acid, along with a magnetic stir bar. Swirl to dissolve the phenetidine. Why are we using the quantities listed in these steps? The amount of product we want depends on what we intend to do with it. In this laboratory course, we want to produce enough to be convenient to handle. Clearly, one must set goals with due consideration for the equipment available. The synthesis of extremely large or small quantities requires different equipment. Cost may be a factor; if reagents are particularly expensive, we may opt for a smaller scale. When first trying a reaction, one must not be surprised if the yield is low. There are always a variety of factors and manipulations that are not anticipated so the results of a first try may be disappointing. If, for example, you wanted 0.8 g of product and assumed a 50% yield then you would start with quantities appropriate for a theoretical yield of 1.6 g. With some luck you may get more the 0.8 g, but if things go poorly, a yield of only 25% will still give you 0.4 g. If you repeat a synthesis, presumably things will go better since you are familiar with the procedure and there will be fewer or no surprises.

3 Why such a big flask for so little volume of reaction mixture? The reaction could be carried out very conveniently in a 50 ml Erlenmeyer flask, but looking ahead, we are going to crystallize the product and need a larger volume of solvent and a larger flask. ence the reaction is done in a 125 ml Erlenmeyer flask. Looking ahead is a good habit to get into. Many students concentrate exclusively on each step as they come to it. If you look over the whole procedure, you will often find situations that can be made more convenient by anticipating the future need. 5. Using a three-finger clamp, clamp the 125 ml Erlenmeyer flask containing the phenetidine (Step 4) in the hot water bath and make sure the bottom of the flask is touching the bottom of the crystallizing dish. Set the magnetic stirrer to a setting of 5 or 6. While the solution of phenetidine is heating and stirring, use a Pasteur pipette to add the solution of potassium cyanate (Step 3) drop-wise until solid starts to form. If no solid forms, remove the Erlenmeyer flask and swirl it gently until solid forms, then replace it in the hot water bath. Add the remaining potassium cyanate solution all at once. Why do we start the addition slowly, and then finish it all at once? Once crystallization has started, there are seed crystals available to encourage the crystallization process and it can go quickly. If the cyanate was added all at once initially, there is the likelihood of very fast precipitation with concomitant co-precipitation of impurities such as solvent, cyanate ion, and unreacted phenetidine with Dulcin. 6. Remove the flask containing the suspension of the Dulcin from the hot water bath and add powdered charcoal to it (use the equivalent of 3 inches placed on the scoopula). Using a graduated cylinder, measure about 75 ml of hot water from the 250 ml Erlenmeyer flask and add this to the 125 ml Erlenmeyer flask containing the reaction mixture. Place the flask directly on the hotplate (set to 4). Continue magnetic stirring, and heat the mixture until it is boiling. This is sufficient solvent to dissolve all the Dulcin (you may not see that it all has dissolved because of the charcoal). If necessary, increase the hot plate setting to 5, until the solution boils. Boil the mixture no more than about 5 minutes. Why the charcoal? ow much charcoal? Pure Dulcin is a snow-white crystalline solid. The phenetidine we started with was distinctly colored, a condition quite common with amines. By adding the charcoal, we adsorb much of the colored material, thus allowing the Dulcin to crystallize without colored impurities. Adding too much charcoal causes loss of product through adsorption, and adding too little leaves colored impurities in the product. The amount to be added is only learned by experience. 7. Take a clean 125 ml Erlenmeyer flask and place an appropriately sized piece of filter paper on a clean wide mouth plastic funnel resting on top of the flask. Clamp the flask to the bench top.

4 8. When the Dulcin has completely dissolved, pour the hot solution from Step 6 into the funnel/filter paper, and allow it to drain into the Erlenmeyer flask. 9. Allow the filtrate from Step 8 to cool somewhat by occasionally swirling the flask at room temperature and then place the flask in an ice-water bath. While it is cooling, prepare a clean filter flask and a clean Büchner funnel fitted with an appropriately sized filter paper for use in the next step. Attach the vacuum hose and clamp the filter flask to the bench top. 10. When the solution is cold, turn on the vacuum, seat the filter paper with a couple milliliters of ice-cold water, and press the funnel down on the filter flask. Swirl the contents of the crystallizing flask to suspend the crystals and then pour the mixture as quickly as possible onto the filter funnel. 11. Rinse the product remaining in the crystallization flask with several milliliters of ice cold water from the ice bath and pour it onto the product in the Büchner funnel. Solid stuck on the sides of the flask may be loosened with a clean glass, stirring rod. 12. When most of the solvent has been removed from the crystals, wash the product in the Buchner funnel with 3 or 4 portions (approximately 2 ml each) of ice water from the ice water bath to remove water-soluble contaminants. ow many rinses? We are in a classic dilemma here. The more washes that are performed, the purer the product will be (at least conceptually). In fact, after two or at most three washings, it is doubtful that any more purification is taking place. At the same time, remember that solvent of any temperature, even cold, will slightly dissolve a solid compound. Additional washings will dissolve more material and reduce the yield so we want to use the minimum number of washes. Unless particular circumstances dictate otherwise, purity is more desirable than quantity. After all, you can usually run the reaction again if you need more material. If increased purity is really important, it is better to re-suspend the material in clean wash liquid (ice water in this case) and re-filter. A reasonable compromise for this course allows us to wash the product contained in the Büchner funnel. ow much water in each wash? Several washings with smaller volumes gives better results than one washing with a larger volume. Each washing should be large enough that the entire solid is exposed to the wash liquid but small enough so that when we are done the total volume is conveniently contained in the filter flask. 13. Allow the material to dry somewhat by pulling air through the product on the Büchner funnel for a few minutes. In the meantime, wash all glassware and clean your work area. Carefully place the top of the Büchner funnel containing Dulcin in your drawer, uncovered, to dry until the next lab period.

5 14. At the next lab period, carefully transfer the Dulcin to a pre-weighed sample vial and obtain a weight on your product, and determine its melting point. Record all data in your notebook. Label the vial and turn in to your instructor. Waste Disposal: a. Plate filter paper in the trash. b. Wash the filtrate from the filter flask down the drain of the sink. c. Clean all glassware and equipment, and return or place it in your locker. Wash and dry your work area. Calculations: 1. Determine how many moles of phenetidine you used. 2. Determine how many moles of potassium cyanate you used. 3. These react in a 1:1 mole ratio. Based on this information, determine which was the limiting reagent in this reaction. 4. Calculate the theoretical yield for your reaction, based on your limiting reagent. 5. Calculate the percent yield for your preparation of Dulcin.

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