Steam Distillation Lab Report/Page | of + NAME DATE LOCKER NO. STEAM DISTILLATION LAB REPORT PRE-LAB: FILL OUT THE TABLE OF PHYSICAL CONSTANTS FOR THE MIXTURE YOU WILL DISTILLING DURING THIS PROCEDURE: ‘Molecular Weight (MW) | Bolling Pole’ (BP) Density Compound g/mole deg Celsius (o/mt) Appecrance Limonene Woter 1. During this procedure, you will be collecting @ mixture of limonene ond water. Limonene and water are not miscible (00 soluble in each other), and so two loyers will form In your receiving flask. Using the Information Inthe table ‘above, which layer wil contain the limonene? 2. At what approximate perature will the limonene and water mixture begin to distil over? Read the procedure ond make o Ist of the glassware that you will be using: Instructor's IntiolsSteam Distillation Lab Report/Page 2 of + STEAM DISTILLATION LAB DATA auld Used Approximate Volume of Liquid Used: mi Temperature ot which first drops entered the receiving vessel: tc Dota Table 1. Temperature/Volume Eo Be ee eee Temp (°C) Volume of Total Disillote Recovered mu Estimated Volume of Limonene Recovered What did you observe when you added KMnO: to cyclohexANE? What did you observe when you added KMnOz to cyclohexENE? What did you observe when you added KMnOs to the Limonene that you collected? Is this what you expected to see? 1. Sketch « graph of your data (volume vs. temperature) Inthe space below:Steam Distillation Lab Report/Page 3 of + 3 isillation procedure? 3. Define Dalton’s Lew (describe, do not just write the equat n). 4. Explain the difference between simple, foctonal and steam distill 1 When is och employed? ‘5. The boiling point during steam ditilotion is usvelly less than 100°C. Why? What srucural group were you testing for when you reacted the limonene you collected with KMnO4? raw the general equation fr the reaction ofan alkene with KMnO4,x Steam Distillation Lab Report/Page + of + Indicate which distillation method (simple, Fectionel or steam) that you would use forthe following (assume al ig volatile and miscible, unless indicated otherwise) __seporoting methonel bp 65 deg C) and water (methanol is completely miscible with woter) __ seporoting p-dichloroberzene (bp 174 deg C) and water (p-dehlorobenzene fs insoluble Ia woter) separating acetone (bp 56 deg C) ond aniline (bp 184 deg C) separating butyl ccatote (bp 126 deg C) and butanol (bp 117 deg C) separating 1,2-cthanediol (bp 196 deg C) ond water (1,2-ethanediol i insoluble in water) determining the bolting point of an wknown quid (asuming the Bqud spore) separating cyclohexane (bp 81 deg C) and cycohexonal (op 161 deg C) separating hexone (bp 69 deg C ond tolvene (bp 111 deg C)‘Steam Distllation/Page 1 of 2 Chem 301 Summer 2016 STEAM DISTILLATION PROCEDURE 1. Construct the steam distillation apparatus as shown below. 2. Use a wide-stem funnel to add your pulp/water. Then move the funnel to your receiving flask (in this case, 0 graduated cylinder), 0 there will be some splashing of the boiling water/limonene mixture as the liquid drops into the receiving flask. 3. Add your pulp mixture to the 250-mL RBF (until a bit over half full) ~ then assemble the remainder of the apparatus 4. In this particular case, you do NOT need to add your magnetic stirrer. 5. Heat the mixture to o boil, intially heating ot “10.” Note: Attempt to control the rate of heating so that excessive foaming does not occur. 6. Make sure to observe the pulp mixture during the distillation. AAt high heat, the sugar in the pulp can begin to burn ~ if this happens, cleaning the round-bottom flask at the end of the procedure will be difficult and time-consuming. If the mixture looks like itis beginning to burn, you can add small amounts of additional water to dilute the mixture. 7. At the first drop of distillote, record temperature and volume of distillate collected (the first temperature reading will have a corresponding volume of 0). 8. Record the volume and temperature every 4 mL, until 28-32 ml of distillate has been collected. 9. Tur off the heat to stop the distillation. 10. The distillate should have two layers. The top layer Is the limonene oil and the bottom is aqueous. 11. Using « disposable pipet, transfer the oil toa clean, dry test tube. 12. Estimate the volume of the organic liquid (<1 mb, >1 ml). 13. Draw a Temperature vs. Volume graph and attach it to your lab report.Steam Distilation/Page 2 of 2 ‘Chem301 Summer 2016 Test for Unsaturation (multiple bonds between two carbon atoms) There are four types of hydrocarbons: alkanes, alkenes, alkynes, and aromatic compounds, each type with different chemical properties. These properties can be used to classify unknown compounds. Alkenes are considered the most reactive of the hydrocarbon classes. They can undergo a wide variety of addition and oxidation reactions. The pi bond electrons readily react with reagents which dare electron poor, such as electrophiles and oxidants. Chemical tests transform an unknown into c different compound with an accompanying change ‘appearance. These tests are often called classification tests because they identify the possible functional groups present. In this lab, you will perfom a simple test to confirm the presence of unsaturation (multiple bonds) in your limonene product. You will first test two knowns, an alkane and an alkene, and then your Product. The following reactions will occur ‘A positive test is @ color change from the purple color of aqueous potassium permanganate to the solid brown manganese (IV) oxide (MnO2. PROCEDURE. 1. Place one drop of cyclohexAne in a depression of a white spot plate and add 1 drop of KMnOx ‘A purple color should be observed, There is no reaction. ‘Stir the solution with a stirring rod and spot the solution onto a piece of filter paper. A purple spot should be visible on the filter paper. 2. Place one drop of cyclohexEne in a depression of a white spot plate ond add 1 drop of KMnO, ‘A.red-brown color should form. Sti the solution with a stirring rod and spot the solution onto a piece of filter paper. A brown spot should be visible on the filter paper. 3. Place one drop of your distilled oil in another depression of a white spot plate, and add 1 drop. KMnO., A red-brown color should form. Stir the solution with a stirring rod and spot the solution onto a piece of filter paper. A brown spot should be visible on the filter paper. 4. At the end of the procedure, wipe out the liquid remaining in the depressions of the white spot plate, and dispose of the towel in the organic paper waste container at the front of the lab. Do NOT simply throw the towel in the regular trash can, DISPOSAL 1. Pour your remaining product (limonene) into the recovery bottle at the front of the lab. 2. Pour the contents of your round-bottom flask (remaining citrus pulp) into the large Buchner funnel set Up nearest to your lab bench. Rinse your flask with a small amount of water, and swirl/brush to remove the remaining residue off the sides of the flask, and pour this into the funnel as well.Steam Distillation Lecture Notes/Page | of 3 STEAM DISTILLATION LECTURE NOTES. Review of Simple and Fractional Distillation ‘Simple ond Fractional Distillations are used when a mixture is miscible (two or more compounds mix together, or are soluble in each other) ‘+ Simple distillation can be used to determine a pure compound's boll ‘compounds whose boiling points differ by more than 70°C. * Fractional distillation is used to separate two compounds whose boiling points differ by less than 70°C. 19 Point, or to separate two Steam Distillation ‘+ Steam distillation isthe distillation of a mixture of water (steam) and a volatile organic compound. ‘© The organic compound must be insoluble (immiscible) in water. ‘+ The mixture will distill over at a temperature below thot of its lowest bolling component. The apparatus for a steam distillation is the same as that of a simple distillation, but the physics is considerably different, as your compound is “distilled” as a minor component of an aqueous mixture, but at a much lower and less destructive temperature than distiling the compound directly. In today’s procedure, we will be using steam distillation to isolate on essential oll, imoner eels. Most oils have constituents that have high boiling points ~ these compounds will decompose under the high heat needed to bring them to a boll. Steam distillation is a much gentler method of ‘achieving this same end. Steam distillotion works because the oil and water are immiscible (are not soluble in each other). from citrus ‘The components of on immiscible mixture boil at a lower temperature than the boiling points of any of its components. Therefore, a mixture of high-boiling point organic compounds and water can be distilled at a temperature less thon 100°C. Last week, we used a mixture of two miscible liquids (liquids that are soluble with each other). The total vapor pressure for such a mixture is equal to the sum of the partial vapor pressures of the ‘components (Raoult’s Law). The boiling behavior of immiscible liquids is different. The total vapor pressure is the sum of the vapor pressures of the pure individual components (Dalton’s Law]. Prom = Pat Ps Note that there are no mole fraction terms in the equation. This means that if you have lots of water or just a little, it will make the same contribution to the vapor pressure. What will happen when you distll€ The mixture will heat up and eventually boil. Since water is the lowest boiling component, the mixture will always boil at a temperature lower than the boiling point of water. Throughout the heating process, water and the organic compound molecules will escape in proportion to their respective vapor pressures at the distling temperature. Since water has a significantly lower boiling point than the organic compound, a much greater proportion of water molecules will be vaporizing at any time during the distillation. Even though the components of the organic compound have @ low vapor pressure, they are volatile enough to vaporize to a small extent, and a small amount will lift off with the water molecules. Since the water and organic compound are not interacting with ‘each other, no enrichment occurs and they will co-distll at a single temperature. Normally, steamSteam Distillation Lecture Notes/Page 2 of 3 istllations are carried out with a large excess of water. When all of the organic compound has distilled over, pure water begins to distil. Since the organic compound is not soluble in water, at the ‘end of the distillation you will have two distinct layers in your receiving flask. ‘Steam Distillation Procedure Notes In this experiment, we will be separating the organic compound, limonene, from the citrus peels. that you brought to class. * A.blender will be avoilable in lab, so if you were not able to blend your pulp at home, you may do so before setting up your apparatus. * When you add the pulp to your round-bottom flask, use wide-stem funnel, * Add enough pulp so that your 250-ml round-bottom flask is just over half-full. * You do not need to add a magnetic stir bar, for this procedure only. Set your heat at a setting of 10. Keep an eye on your pulp mixture, as the sugar in the citrus peels can begin to burn at higher temperatures. If this begins to happen, you can small amounts of additional water to your distilling flask. * The distillate will consist of two layers: the top layer will be the organic layer, containing the limonene; the bottom layer will be aqueous. (You should be able to predict this ahead of time. The density of limonene is 0.8411 g/ml; the density of water is 1.0 g/ml.) * Collect the distillate in a graduated cylinder, so that you can measure the amount of limonene oll that you collect (measure the amount of water that comes over as welll. * Transfer the limonene oil to a clean, dry test-tube. * Add a few granules of anhydrous calcium chloride. This is a drying agent, and will absorb any residual water that was transferred over with the limonene oil * You always want to decant your final product off of the drying agent. The drying agent can be discarded into the sinks, while flushing with water.Steam Distillation Lecture Notes/Page 3 of 3 whiteboard notes k= — EE simple fractional ‘steam Y miscible 7 miscible 7 immiscible in water Y more than 70 deg diff | less than 70 deg diff |v’ boils above 100 deg, and Y volatile ¥ volatile ¥ decomposes at or near its BP ¥_must have at least some volatility Purpose of Today's Procedure Lamonche Tsolate limonene from citrus peels by steam distillation (same set-up as for simple distillation). + Record temperature vs volume, and graph data. deh 0.24 + Perform a classification test to confirm our product, by checking for unsaturation (the BP 140°C presence of C:C bonds). Limonene boils at 176 deg Celsius, but at that temperature it will decompose. Steam distillation allows us to distill it over at a temperature that is below 100 deg Celsius. Tnaheterogeneous mixture, the vapor pressure of each component is independent of the other: ‘the vapor pressures are not linked to their concentrations. Instead, each component exerts a partial pressure against the external pressure, and when the sum of these partial pressures equals atmospheric pressure, the mixture boils. This mixture will therefore boil below the lowest boiling point component, in this case water, and so the mixture boils below 100 deg C. Tiss deserted by baltors Lowe in ee Hee Wmonene ol den 0.84- wakr = dent.co Testing for the Alkene Functional Group There ore a number of tests that can be used to test for different funcional groups. Today, we will be using a potassium permanganate solution to test for the carbon-carbon double bond (unsaturation) that is present in limonene. First, you will test a known alkAne (no multiple bonds between carbon atoms), and a known alkéne multiple bonds between two carbon atoms}. You will observe the results, and then perform the same test on your limonene product.Alkene Classification Tests/Page | of 2 Chem 501 Summer 2016 ALKENE CLASSIFICATION TESTS ‘Two common types of unsaturated compounds are alkenes and alkynes, characterized by the carbon-carbon double and triple bond, respectively, as the functional group. Two common Qualitative tests for unsaturation are the reaction of the compounds with bromine in carbon tetrachloride and with potassium permanganate. In both cases a positive test is denoted by decolorization of the reagent. Potassium Permanganate (Baeyer Test) ‘One qualitative test for unsaturation, the Boeyer test, depends on the ability of potassium permanganate to oxidize the carbon-carbon double bond to give alkanediols or the carbon- carbon triple bond to give carboxylic acids 7 Ho Ce Ma 7 Purple + Mog Ee RCo + COR + MnO: a Brown Ppt The permanganate is destroyed in the reaction, and a brown precipitate of MnO> is produced. The disappearance of the characteristic color of the permanganate ion is a positive test for unsaturation. However, care must be taken, since compounds containing certain other types of functional groups (for example, aldehydes, containing the -CH=O group) also decolorize permanganate ion. PROCEDURE 1. Place one drop of cyclohexANE in a depression of a white spot plate and add 1 drop of KMnO« A purple color should be observed, indicating no reaction. Stir the solution with a loss stirring rod and spot the solution onto a piece of filter paper. A purple spot should be le on the filter paper. 2. Place one drop of cyclohexENE in a depression of a white spot plate and add 1 drop of KMnOx. A red-brown color should form indicating @ positive reaction. Stir the solution with a glass stirring rod and spot the solution onto a piece of filter paper. A brown spot should be Visible on the filter paper. 3. Place one drop of your product in another depression of a white spot plate, ond add 1 drop KMnO. ‘A red-brown color should form indicating a positive reaction. Stir the solution with o stirring rod and spot the solution onto a piece of filter paper. A brown spot should be visible (on the filter paper.Alkene Classification Tests/Page 2 of 2 Chem 301 Summer 2016 Bromine in Carbon Tetrachloride Bromine will add to the carbon-carbon double bond of alkenes to produce dibromoalkanes and. with alkynes to produce tetrabromoalkanes. When this reaction occurs, molecular bromine consumed, and its characteristic dark red-brown color disappears if bromine is not added in ‘excess. The ropid disappearance of the bromine color Is @ positive test for unsaturation. cc Alkyne Red-Brown You will not be performing this test in lab as the reagent has a distinct ond unpleasant odor, but you should be familiar with the test.