Synthesis of Adipic Acid Essay example

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Experiment 8: Synthesis of Adipic Acid

Performed November 8th & 10th
Jennifer Seitz

Organic Chemistry 344
Section 803
Fall 2011

Objective: The purpose of this experiment was to synthesize adipic acid from cyclohexanol via an oxidation reaction that was catalyzed by sulfuric acid. Purity of the product was assessed by measuring the melting point.

Physical Properties/Structures:

Name | Formula | Molecular Weight (g/mol) | Boiling Point (0C) | Melting Point(0C) | Density(g/mL) | Hazards | Sodium Dichromate Dihydrate | Na2Cr2O7 . 2H2O | 297.98 | 400.0 | 357.0 | 2.35 | -Eye/skin irritant-Affects Respiratory System | Water | H2O | 18.02 | 100.0 | 0.0 | 1.00 | N/A | Sulfuric Acid (98%) | H2SO4 | 98.08 | 337.0 |
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The oxidation reaction between cyclohexanol and sulfuric acid was successful in that it did in fact yield the adipic acid product but unsuccessful in the amount that was yielded, with a percent yield of only 35.0%. This yield may have been low due to both experimental and technical errors. One of the major causes of the low yield most likely had to do with the fact that the temperature went below 55.00C and above 65.00C during certain points of the reaction. When the reaction temperature goes above 65.00C, it causes the yield of adipic acid to be lower due to further oxidation. When the reaction temperature goes below 55.00C, it causes the yield of adipic acid to be lower due to the fact that the amount of energy is not high enough to activate oxidation of the reaction. Some of the product also most likely was lost during both the crystallization and recrystallization process. Since adipic acid is somewhat water soluble, some of the product most likely moved with the water that was used to rinse it through the filter out of the Buchner funnel during vacuum filtration. This error could have been reduced had the
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