Synthesis of Adipic Acid

Experiment 8: Synthesis of Adipic Acid

Performed November 8th & 10th
By
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 | 10.0 | 1.84 | -Eye/skin irritant-Affects Respiratory System-Produces large amounts of heat-Corrosive | Cyclohexanol | C6H12O | 100.16 | 160.84 | 25.93 | 0.96 | -Eye/skin irritant-Affects Respiratory System-Ingestion Hazard-May be combustible at high temperatures | Chromic Acid | H2CrO4 | 118.01 | 250.0 | 197.0 | 1.20 | -Eye/skin irritant-Affects Respiratory System-Corrosive | Adipic Acid | C6H10O4 | 146.14 | 337.5 | 152.1 | 1.36 | -Eye/skin irritant-Affects Respiratory System-May be combustible at high temperatures | Chromium (III) Salts | CrCl3 | 266.48 | 1300.0 | 83.0 | 1.76 | -Eye/skin irritant-Affects Respiratory System | Alumina | Al2O3 | 101.96 | 2977.0 | 2072.0 | 3.95 | -Eye/skin irritant-Affects Respiratory System |
Source: Material Safety Data Sheet (2008).

Equations:

Procedure:

Part I: Sodium dichromate dehydrate (14.99g) was placed in a 100 mL beaker and dissolved in 30.0 mL of water where it was observed to turn a neon orange color. The solution was cooled in an ice-water bath and 8.0 mL of sulfuric acid was slowly added to it in 1.0 mL portions. The chromic acid solution was then mixed until homogeneous and cooled to 10.00C in an ice-water bath. While the solution was cooling, 9.0 mL of sulfuric