Experiment 5

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Chemistry

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Feb 20, 2024

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Experiment 5: Isolation of Trimyristin from Nutmeg and Preparation of Myristic Acid from Trimyristin by Hydrolysis and Preparation of Myristic Acid from Trimyristin by Hydrolysis Chase Morris 3/3/2023 CHM2210L-29 Heng Liu
Introduction: The isolation of an organic compound entails separating the a compound from other compounds in a mixture. There are various different ways to isolate an organic compound such as extraction, distillation, chromatography and crystallization. In this lab we will perform a hydrolysis of esters which can be done through acid-catalyzed and base-catalyzed hydrolysis, in this experiment base-catalyzed will be performed. Hydrolysis is the process of cleaving an ester bond by the addition of water, and in the presence of an acid or base the esters can be hydrolyzed to produce a carboxylic acid and an alcohol. In base-catalyzed hydrolysis the ester is reacted with a strong base, the strong base deprotonates the water molecule making it nucleophilic and able to attack the ester. The mixed melting point concept is the same as the melting point constant, it is used to test the purity of a compound, if the melting point of a compound is lower than expected it is due to an impurity of the compound. The mechanism used to hydrolyze myristic acid from trimyristin is a four step process. First the base-catalyzed hydrolysis will produce myristic acid and glycerol, then the solution is neutralized to counter the byproduct from the base-catalyzed hydrolysis. After it is neutralized myristic acid can be extracted from the solution by separating the layers and then drying the myristic acid. Finally the myristic acid needs to purified by recrystallization. There are different ways that an unwanted byproduct can be formed during this reaction whether it be saponification, acid-catalyzed dehydration, and isomerization.
Procedure: A 50mL Erlenmyer Flask 2g ground nutmeg 20mL diethel ether mix 20 mins Pasteur Pipet 2mm sand 1cm anhydrous sodium sulfate Place over 25mL vacuum flask with rubber septum clamp New Pipet Transfer content form erlenmyer flask Let flow through to vacuum flask Rinse packing material with .5 ml ether 25mL vacuum flask Cool in ice bath Dissolve with 1mL acetone over steam bath Hirsh Funnel Wet filter paper and rince with acetone Transfer solid sample to preweighted vial
B Chemicals Used: Trimyristin o Physical Properties Melting point: 56-57 c Boiling point: 311 c Molar mass: 723.16 g/mol o Chemical Properties Chemical formula: C45H86O6 5mL Vial 200mg trimyristin 2mL ethanol 2mL 10% NaOH Boiling stones Run for 1 hour 50mL beaker Cold 10mL HCl Add mixture from vial check pH Dilute with 5mL cold water Vacuum filtrate Save crude Test tube 5mL petroleum ether Crude mixture Filter pipet 1in celite Myristic acid solution Gently force through with bulb Test tube Filtered myristic acid solution Evaporate solvent using steam bath Cool
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