Simple Distillation

Objectives: 1. Define the boiling point of a pure liquid and discuss why and how it is influenced by atmospheric pressure. 2. Experimentally determine the boiling point of a pure liquid by the method of distillation. Background: Liquid molecules are held together by attractive forces. A liquid in an open container slowly evaporates because some of the molecules have enough energy to break these attractive forces and leave the surface. Most of them migrate so far from the surface that they never return. A liquid placed in an empty closed container will evaporate for awhile, but eventually some of the lost molecules do return to the surface to condense and rejoin the liquid itself. After a period of time, the evaporation and condensation will be occurring at the same rate and the liquid level will no longer change. The pressure exerted by the molecules in the gas phase is called the vapor pressure of the liquid, and increasing the temperature will cause an increase in the vapor pressure (a greater number of molecules have enough energy to break the attractive forces). The presence of other different molecules in the space above the liquid has no effect on vapor pressure (as long as they dont condense), and therefore a given liquid at a given temperature will have a given vapor pressure. Liquids with high vapor pressures at room temperature are called volatile and those with low vapor pressures at room temperature are called nonvolatile. Examples of vapor pressures at 25 C are: water = 23.8 torr, methyl alcohol = 122 torr, and diethyl ether = 470 torr. Boiling is different from evaporation. In boiling, molecules throughout the liquid (not just those near the surface) are breaking the attractive forces. Bubbles of vapor form anywhere within the liquid and rise to the surface. For boiling to occur, the liquid has to be hot enough so that its vapor pressure equals the atmospheric pressure (760 torr at sea level on an average day). If the liquid is not hot enough, the bubble of vapor will not have enough pressure to form and rise to the surface. As you can tell by the room-temperature vapor pressures in the paragraph above, ether does not have to be heated very much to increase its vapor pressure to 760 torr. Therefore, it has a low boiling point (35 C). Water, on the other hand, needs to be heated to 100 C to boil at normal atmospheric pressure. Also note that if the atmospheric pressure changes, the boiling point of a substance changes. Thus, if you are in the mountains, the atmospheric pressure is lower, and so is waters boiling point. A pressure cooker increases the atmospheric pressure inside it and the boiling water will be hotter than 100 C. Phoenix is slightly above sea level, and boiling points determined here can be 1-2 degrees below the literature value. Boiling points can be determined by the process of simple distillation (boiling followed by condensation of the pure vapors, leaving solid impurities behind). If a pure liquid is used, the temperature of the rising vapor will remain at the boiling point until it reaches the water-cooled condenser. A pure liquids boiling point (corrected to sea

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level) is a good indicator of its identity. However, it is not a good indicator of its purity if the impurities are other liquids or gases. Mixtures of liquids may have boiling points above, below or the same as an individual component. Some, but not all, liquid mixtures may be separated by a process of fractional distillation (next lab). You will receive a pure liquid as an unknown, and you are to distill it and carefully record its boiling point. Then you will identify it by comparing boiling points with the list below. Your unknown is one of the following: Liquid pentane dichloromethane 1-chloropropane acetone hexane 1-chlorobutane cyclohexene 2-iodopropane water Boiling point in C at 760 torr 36.1 40.0 46.6 56.5 68.7 78.4 83.0 89.5 100

Procedure: Obtain an unknown and record its number. Assume your unknown is moderately flammable and toxic. Do not breathe the vapors unnecessarily. Use heating mantles and controllers. Do not light Bunsen burners! Important: Preheat the mantle at a setting of 60 volts for 10 minutes before placing the round bottom flask in it. Place the heating mantle under the flask and adjust the apparatus until the flask rests in the mantle. (Flask must be touching the bottom of the mantle.) Unscrew the round-bottom flask and add a couple of boiling stones and all of your liquid unknown (use a funnel). Wipe any unknown off the neck of the flask and reconnect it. Attach the apparatus to the ring stand at the still head with a micro clamp. Connect the hoses on the condenser so that water enters the lower connection and leaves from the upper connection and adjust the water to a very slow steady flow rate. Be sure that the end of the water hose is directed towards the bottom of the cup sink. (If you dont, we may have a flood!) Check the thermometer position and all connections, and place a small beaker under the condenser to collect the liquid. See the diagram and picture for details of the setup. Your instructor must check your setup before you begin! Note: Do not shake down the thermometer. If you are not sure how to read the thermometer, ask your instructor. (divisions may be I or 2 C). Carefully control the heat and distill the liquid. Record the temperature when the first drop is collected (may be low due to dissolved gases), and at five-drop intervals. Do not heat the flask to dryness. When you are finished, turn off the controller and allow the apparatus to cool before attempting to clean it. Plot the data on the graph provided in the lab report. The temperature range over which most of the liquid distills 2/6

(the distillation temperature) is considered by organic chemists to be the boiling point. Boiling points, like melting points, are always reported as ranges.

Waste Handling: Any unused portion of your unknown should be emptied in the waste container in the hood before returning the empty vial to the supply cart. When finished with the distillation, dispose of the unknown in the waste container in the hood.

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Report: Simple distillation

Name: __________________________ Section #: ______________ Unknown # ____________

Volume, drops 1 5 10 15 20 25 30 35 40

Temp. C

Volume, drops 45 50 55 60 65 70 75 80 85

Temp. C

Graph your results, and mark on the graph the beginning and the end of the boiling point range of your unknown (ignore the 1st drop). Experimental boiling point range ___________ Identification of unknown __________________________. If there is more than one possibility, explain.

Questions: 1. Why are boiling chips added to the liquid before heating is begun?

2. Why is the boiling point of a compound not as useful to an organic chemist as the melting point of a compound?

3. If a vacuum pump is hooked up to the arm of a stoppered filter flask containing a little water, the water will boil at room temperature. Explain.

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