Lab 1: Purification of Acetone by Simple Distillation Pre-Lab Assignment: 1.

Before coming to lab, read the following sections from Zubricks The Organic Chemistry Lab Survival Manual: Chapter 1 Safety First, Last and Always Chapters 4-6 Jointware, Microscale Jointware, and Other Interesting Equipment Chapter 19 Clamps and Clamping Chapter 20 Distillation Chapter 36 Theory of Distillation 2. Prepare your notebook (see syllabus and Zubrick Chapter 2 Keeping a Notebook) so that you are ready to perform the experiment. While performing the experiment, use your notebook to record all data and observations. Specific Objectives: 1. 2. 3. 4. Upon completion of this experiment, you will: Know how to prepare and maintain an organic laboratory notebook. Become familiar with the glassware and equipment in your lab drawer and cabinet. Be able to set up and perform a simple distillation. Become familiar with the theory of distillation.

Background: The temperature of a liquid increases with heating until it reaches a certain temperature known as the boiling point. Further heating causes the liquid to vaporize and vigorously bubble. The process of heating a substance until it vaporizes, cooling the vapors, and collecting the condensed vapors as liquid, is known as distillation. Distillation is one of the fundamental techniques used to purify organic compounds. Organic liquids containing small amounts of impurities, non-volatile substances, or very high boiling substances, are easily purified by simple distillation. A typical simple distillation apparatus is shown in Figure 1. It consists of a flask (distillation or pot flask) containing the material to be distilled, a distillation adapter that connects the distillation flask to a water-cooled condenser (West condenser) as well as a thermometer adapter, and a flask (receiving or collection flask) used for collecting the distilled liquid. The distillation flask is a round bottom flask filled 1/2 to 2/3 of its capacity. Boiling chips or a magnetic stir bar are added to the flask before the liquid is heated to promote even heating. Boiling chips provide sites for bubbles of vapor to form and the magnetic stir bar agitates the liquid as it is being heated. Both

Keck clip

Keck clip Clamp flask to ring stand HERE

H2O out at the top Use 250 mL round bottom flask as the distillation flask H2O in at the bottom

Keck clip

Use 100 mL round bottom flask as the receiving flask

Figure 1. Apparatus for Simple Distillation prevent the liquid from becoming superheated, which can lead to bumping and sudden, explosive episodes of violent boiling. The distillation adapter, often referred to as a distillation head or still head, connects the distillation flask, the condenser, and the thermometer. The ground glass joints must be greased and joined tightly and securely with the other pieces of glassware using Keck clips to avoid leakage of the vaporized liquid during distillation. Leaking vapor will result in loss of some of the liquid. The thermometer probe should be position so that the last 1 cm of the probe tip is below the curve of the side arm that connects to the condenser. In order to obtain accurate temperature readings during the distillation, the vapors of the heated liquid must completely engulf and contact the last 1 cm of the thermometer probe

tip. If the probe tip is not lowered enough into the vapors, the measured vapor temperature will be lower than the actual vapor temperature. The condenser (West condenser) cools the vapor causing it to condense and liquefy on the interior surface of the glassware directing the liquid into the receiving flask. A West condenser is a water-jacketed type of condenser. Water lines are attached from a faucet in the hood to the condenser such that water flows in through the lower hose connection (farthest from the pot flask) and out through the upper hose connection into a sink or drain. The water flow should be adjusted so there is a slow, constant flow of cold water through the condenser. The receiving flask collects the liquefied vapor. It may be a round bottom flask, an Erlenmeyer flask, a bottle, or a graduated cylinder. The receiving flask is connected to the condenser with a vacuum adapter, which allows the system to remain open to the atmosphere. It is good practice to submerge the receiving flask in a cold-water or ice water bath to prevent low boiling liquids from evaporating out of the vacuum adapter into the atmosphere. The process of distillation begins by slowly heating the distillation flask. The amount of heat applied is determined by the eventual rate of distillation (drops of liquid collected in the receiving flask per minute). The liquid in the distillation flask should begin to gently boil and vaporize. As vapor forms and travels upwards, it will fill the distillation flask and most of the distillation adapter. The vapor will heat the glassware it comes into contact with, condense, and drip back into the distillation flask. It is important to insulate areas heated by the vapor to prevent them from condensing and dripping back into the distillation flask. Eventually, the vapor condenses in the condenser and drips into the receiving flask. The rate at which the liquid drips should be 10 to 20 drops per minute (or 1 drop every 3 to 6 seconds). If the rate of distillation exceeds 20 drops per minute, the heat applied to the distillation flask must be decreased. With too rapid a distillation rate, the measured boiling point is likely to be inaccurate and the purity of the distilled liquid will be compromised. The behavior of the observed vapor temperature during the course of a simple distillation depends upon the identity of the liquid(s) in the distillation flask. As the liquid vaporizes and vapor comes into contact with the thermometer, the observed temperature will increase. The observed temperature will stabilize at the boiling point of the liquid being distilled. When all of the liquid has been distilled off the temperature will decrease. Typically, some liquid will distill and be collected before the observed vapor temperature stabilizes around the boiling point of the distilled liquid. The liquid that is collected is called the forerun. This will contain any low boiling impurities and should be discarded. The liquid collected after the temperature stabilizes is the purified substance. Usually, the temperature of a distilling liquid will stabilize slightly below the literature value for its boiling point and slowly increase over the course of the distillation to that value. The distillation is halted when the observed vapor temperature begins to decrease. This is achieved by removing the heat from the distillation flask. The boiling point temperature of the collected liquid is actually the temperature range over which it distilled, not a single temperature.

Experiment: You will obtain a sample of acetone containing a small amount of impurity and purify it using simple distillation. Reagents and Properties Table: Reagents Acetone Procedure: Check-in: Before beginning this experiment, please see the instructor for your check-in sheet and assigned lab drawer and hood number. Begin familiarizing yourself with all of the glassware in the drawer and the macroscale and microscale glassware cases as you check them in (see Zubrick Chapters 4-6 for descriptions and figures). Safety quiz: Your instructor or TA will administer a safety quiz so that you know where to find the showers, eyewash stations, fire extinguishers, etc. When you are finished, you may begin the experiment. Purification of Acetone by Simple Distillation: 1. Obtain 100 mL of crude wash acetone in an Erlenmeyer flask. 2. Assemble a simple distillation apparatus as shown in Figure 1. a. Add 5 boiling stones to a 250 mL round bottom flask (distillation flask) and securely clamp it around the neck of the flask to a ring stand. Make sure the clamp is secure and clamped below the lip of the neck of the distillation flask. b. Transfer the crude acetone into the distillation flask. c. Make certain that your ground glassware joints are properly greased before you begin assembly of the apparatus. d. Secure specified glassware joint connections with Keck clips. e. Connect water hoses from the cold-water tap to the West condenser as indicated in Figure 1. f. Insulate the top of the distillation flask and distillation adapter by loosely wrapping both with either aluminum foil or glass wool. Leave a small window so that you can observe the interior of the distillation flask. 3. You will use a heating mantle to heat your distillation flask. Lower the pot flask into the heating well. Leave a 0.5-1 cm gap between the surface of the flask and the surface of the heating well. Do not allow the flask to come into direct contact with the heating well. a. NOTE: be sure that water is gently flowing through the condenser before you begin heating. MF C3H6O MW 58.08 g/mol Density 0.7925 g/cm3 BP 56.5C Amount 100 mL

4. Begin slowly heating the distillation flask. Start heating with your powermite set to 30% power. 5. When the appropriate temperature has been achieved, the crude acetone will begin to boil, distill, and pure acetone will collect in the distillate flask. Record the temperature range at which the acetone distills. a. NOTE: discard the forerun if any liquid is collected before the observed vapor temperature stabilizes. 6. When about 10 mL of impure liquid remains in the distillation flask, lift the flask up and out of the heating mantle and allow it to cool. DO NOT DISTILL TO DRYNESS!!! 7. Disassemble the distillation apparatus and return the glassware and equipment to your lab drawer or macroscale glassware case. a. NOTE: usually you will need to clean your distillation apparatus glassware. In this case, it is not necessary because you have distilled acetone through out the entire apparatus. Only the distillation flask needs to be cleaned. 8. Discard what remains in the distillation flask in an appropriate waste container and rinse the flask with some of the clean acetone you just distilled. Transfer the remaining distilled acetone into your acetone wash bottle in your fume hood. 9. Clean up your bench, make sure everything is put away in its proper storage container, and have your instructor or TA check your area and sign your notebook pages. Turn in your notebook carbon copies.