ExtractionLab1

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University Of Georgia *

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2212

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Chemistry

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Feb 20, 2024

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Extraction of Trimyristin from Nutmeg Lab --------------------------------------------------------------------------------------------------------------------- Introduction: Extraction is a process where a single compound is removed from a mixture. An example of this is extracting caffeine from coffee beans. There are two types of extraction, solid-liquid extraction and liquid-liquid extraction. Solid-liquid is when a compound is extracted from a solid mixture with a liquid solvent. The separation is based on the compound’s solubility in the solvent. Liquid-liquid extraction is the separation is based on the relative solubilities of the two liquids. Reflux is the process of boiling the reactants while cooling the vapor and returning it back into the flask. A condenser with water is used for this. Refluxing is used to heat mixtures for extractions and to heat something for an extended period of time. Suction filtration is used to remove moisture and leave the substance on top of the filter dry. In this lab, solid-liquid extraction is used to isolate trimyristin from nutmeg. Nutmeg has about 20-25% trimyristin. Trimyristin is made of myristic acid and glycerol. Methyl chloride is the solvent used in the distillation. The acetone is used to remove impurities in the trimyristin crystals that are extracted. The purpose of this lab is to extract trimyristin from nutmeg using reflux and distillation. The resulting trimyristin crystals are compared to true trimyristin to analyze the effectiveness of the extraction. Percent yield is calculated for the amount of trimyristin extracted and the percent error for the melting point of the crystals. These are used to compare the results of the extraction. Table of Reagents: Name Molecular Structure Molecular Boiling Melting Density
Weight point Point Acetone 58.08 56℃ - 784 kg/m 3 Methylene Chloride 84.93 39.6℃ - 1.33 g/cm 3 Trimyristin 723.18 311℃ 56 885 kg/m 3 Safety Information: General Safety: The dress code is to wear a lab coat, safety glasses, closed toed shoes, full pants and a shirt. Snorkels are put on top of the table and the experiment. Waste that has touched chemicals goes in the hazardous waste bin and liquid waste goes in the liquid hazardous waste bottle. Boiling chips should be added before heating and hot glassware should not be touched. Chemical safety: - Acetone is flammable and can cause eye irritations. It can also affect the nervous system and the respiratory system. - Methylene chloride is a carcinogen that can affect the liver and cause eye and skin irritations. Experimental Procedure: Solid/Liquid Extraction
1. 4.5 grams of nutmeg and boiling chips are put into a 100mL round-bottom flask. 45mL of methylene chloride is added to the flask 2. The flask is clamped to a ring stand and a water-cooled condenser is added to the top. A heating mantle is attached to the bottom. 3. The heat is turned on and the reflux timer starts once the solution boils 4. After 30 minutes, the heat is turned off. Once the system has cooled, it is disassembled 5. The solution is filtered into another 100mL round bottom flask using a funnel and filter paper Simple Distillation and Filtration 1. A hot plate is heated to 40 and the solution is transferred to a 400mL beaker placed on top of the hot plate. The snorkel is put directly above the beaker. 2. The distillation is done until there are a few milliliters of solution left in the flask and there is no smell of methylene chloride. 3. The remaining solution in the beaker is cooled in an ice water bath. 10mL of acetone is also added to an ice bath before being added to the solution in the beaker. A glass rod is used to break up the clumps of crystals. 4. The crystals are collected with suction filtration and transferred to a 100mL beaker to get washed with 10mL acetone again. It is then suction filtered again. 5. Once the crystals are dry, they are weighed and the melting point is determined. Data and Observations: Starting weight of Nutmeg 4.501g Volume of methylene chloride 45mL
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Mass of trimyristin 0.481g Measured melting point of trimyristin 55.8 Nutmeg is light brown in color. Methylene chloride is clear and has a smell. The solution in the flask after suction filtration is light yellow. The solution was dark yellow during distillation. The trimyristin crystals are a white powder. Results: Temperature Percent Error: 56-55.8/56*100= 0.357% Calculated theoretical amount of trimyristin: 4.501g*0.20=0.900 grams Percent Yield: 0.481g/0.900g*100= 53.4% Discussion/Conclusion: Extraction can be used to isolate a compound from a mixture. Reflux can also be used to heat a mixture for a long time without losing the solvent. Distillation of the methylene chloride and trimyristin was done in a beaker on a hot plate because methylene chloride’s boiling point is much lower than trimyristin. The percent yield of trimyristin was 53.4%. The percent yield was low because a lot of the original mass was lost while transferring into other glassware. Not all of the trimyristin was transferred from the suction filtrations. This could be improved by using less glassware so there are fewer transfers and taking more time to fully get all of the trimyristin crystals. The percent error for the melting point was 0.357%. This shows that the substance extracted is mostly pure trimyristin since the melting points are very close.
Post-Lab Questions 1. Hypothetical scenario: during your experiment, you recovered 3.21g of pure trimyristin from a 20.15g sample of finely ground nutmeg, what is the experimental recovery in mols of trimyristin from this solid/liquid extraction? Show your work below: 20.15g*0.2= 4.03g theoretical yield 3.21g/4.03g*100= 79.7% experimental recovery 2. Define/explain the organic chemistry laboratory technique of reflux. What was its role in this experiment and how was it implemented (apparatus/setup)? Be detailed in your answer: Reflux is the technique of heating a solution without losing the solvent. The role of reflux in this experiment was to heat the nutmeg and dissolve it so the trimyristin can be extracted without boiling all the methylene chloride away. A round bottom flask is placed on top of the heat source and has a water-cooled condenser on top of it. The lower opening on the condenser is attached to the sink and the upper opening goes to the drain. 3. What is the purpose of performing a simple distillation in this experiment? What role did it serve? What was the distillate collected in the receiving flask (identity/composition)? Simple distillation was used to remove methylene chloride and to isolate the trimyristin. The distillate collected was methylene chloride. Trimyristin remained in the beaker because it has much higher boiling point compared to methylene chloride