The Unconventional Production of Ethanol Austin Heeren and Dr. David Oostendorp Loras College

1. The Unconventional Production of EthanolAustin Heeren and Dr. David OostendorpLoras College 1. Lithium Aluminum Hydride A B C Product 2. Hydrochloric Acid Introduction Methods Results/Conclusion • Ethanol is a chemical substance that has applications in the consumer alcohol market, as well as in the industrial production of many other chemicals such as akyl halides, esters, and diethyl ether, a common solvent. • Ethanol is generally produced for the beverage industry by the microbial fermentation of starch and cellulose (plants). • The most notorious chemical production of ethanol is from the hydration of ethene. Ethene is an unsaturated hydrocarbon that reacts with steam to form ethanol. While this method is effective, it uses steam, is done at high temperatures, and only has a 5% yield at equilibrium. • The reaction with acetic acid produced nothing but the reactants. The acetaldehyde intermediate may not have been formed or may have escaped as a gas. • The reaction with acetaldehyde indicated similar results. There was a noticeable smell from the reaction of lithium aluminum hydride and acetaldehyde, suggesting that acetaldehyde was lost. • In the third set of reactions, with ethyl acetate, the distillate had considerable product in the 65-80 °C range. The median boiling was 72 °C, suggesting the product was a mixture of THF and ethanol. • The amount of product increased as the amount of solvent was increased, suggesting that the product contains solvent and the solvent is vital to the reaction. • The reactions with acetic acid and acetaldehyde would have benefited from more accurate temperature monitoring and an apparatus better suited for gases. • This data suggests that the most effective to produce ethanol in this study is using ethyl acetate. This evidence does not conclusively prove that their are alternative routes of ethanol synthesis, but rather identified favorable conditions to be expanded upon. • Measure: 3 portions of .03 mol (about 2 grams) acetic acid and place into separate vials; 3 equivalents or .09 mol lithium aluminum hydride, and place in a beaker; 1:1, 2:1, and 3:1 mole ratio of solvent to the main reactant (03 mol, .06 mol, and .09 mol portions of THF • Set up an apparatus for reflux under the hood. Carefully add the lithium aluminum hydride to a 100 ml round bottom flask. • Mix combine the first portion of acetic and solvent; with the condenser running add the mixture from the previous step . Add heat as needed to start the reaction. • After reaction slows, remove heat and add 12M HCl. • After reaction is complete, remove the condenser, and set up a simple distillation. Separate distillate into beakers for three ranges: 64 °C, 65-80 °C, and 81+ °C • Repeat Steps, for the 2nd and 3rd portion; then repeat the whole process, for acetaldehyde and ethyl acetate. • Take an infrared spectra of suspected products. Purpose • Our objective was to find multiple ways to synthesize ethanol in the lab. We also what to understand what conditions are best suited for the production of ethanol. The effect of temperature, concentration, and solvent on the production of ethanol will be the main conditions of the experiment. • There are many common chemicals in lab, that theoretically can cause the unconventional production ethanol. This study focused on the hydride addition of lithium aluminum hydride to these different common chemicals. • Lithium aluminum hydride is an advantageous reactant because it can be fully recovered from the reaction; so only the main chemicals would need to be replaced. Simple Distillation Reflux Apparatus IR of distillate and pure ethanol Properties Table References Pure Ethanol Davalian, D.; Garratt, P.; Riguera, R. Metal hydride reduction of bicyclo[2.2.2]octa-2-ones. Preparation and stereochemistry of 5-substituted bicyclo[2.2.2]octan-2-ols. J. Org. Chem. 1977, 42 (2), pp 368-369. Jin, H.; Liu, Q.; Wu, Y. On the Susceptibility of Organic Peroxy Bonds to Hydride Reduction. J. Org. Chem. 2005 70 (11), pp 4240-4247. Hunt, Ian. Carboxylic Acid Derivatives. Nucleophilic Acyl Substitution. http:/www.chem.ucalgary.ca/courses/350/Carey5th/Ch20/ch20-3-3-2.html (accessed 3/10/2012). Calgary: Alberta. Smith, K.; Beauvais, R.; Holman, R. Selectivity versus reactivity: The safe, efficient metal hydride reduction of a bifunctional organic. J. Chem. Educ. 1993, 70 (4), pp A94. Ethanol + THFDistillate