6-Aminohexanoic Acid → hexanoic acid, 6-amino-, monosodium salt

Participants

Reaction Conditions

Reaction Steps

A jacketed 100 mL titration vessel was maintained at 15° C. by a circulating cooling bath. 6-Aminocaproic acid (10.416 g, 0.0794 mol, 2.1 equiv.) was dissolved in 20 mL of 14% aqueous NaOH (0.0794 mol, 2.1 equiv.) at 25° C. to form a solution of sodium 6-aminocaproate. The solution was placed into a 100 mL jacketed beaker which was maintained at 15° C. by a circulating cooling bath. Terephthaloyl chloride (7.674 g, 0.0378 mol, 1 equiv) was added in one portion and the reaction mixture stirred rapidly with a mechanical stirrer. The original pH of the solution was 12.8. As hydrochloric add was generated by the condensation of terephthaloyl chloride and sodium 6-aminocaproate, the pH began to fall. When the pH electrode in the solution sensed that the pH had dropped below the specified pH (in this case, pH=11.00), 14% NaOH was automatically titrated into the reaction to neutralize the hydrochloric acid. In this way the desired pH was maintained for the duration of the reaction. Completion of the reaction can be monitored visually by noting the disappearance of solid terephthaloyl chloride, or by uptake of sodium hydroxide with respect to the required theoretical amount. At the end of the reaction, the mixture was filtered through a bed of celite on a Buchner funnel to remove any unreacted terephthaloyl chloride. The product was precipitated by addition of 2.1 equivalents of 1 molar aqueous sulfuric acid isolated by filtration. The resulting white solid was washed with water to remove any residual NaCl, Na2SO4 or 6-aminocaproic acid. Typical yields: 90-93%.

Provenance & Evidence