Ammonia → Glycine

Participants

Reaction Conditions

Reaction Steps

50.01 g (0.6662 mol) of glycine and 100 ml of an aqueous solution of 26.68 g (0.667 mol) of NaOH were fed into a 2Λ four-necked flask equipped with a stirrer, a thermometer and a dropping funnel, and heated while stirring. Then, 37.23 g (0.7017 mol) of acrylonitrile was dropwise added to this solution over a period of about 20 minutes while stirring. During the dropwise addition, the reaction system was maintained at a temperature of from 40 to 50° C. After the completion of the dropwise addition, the reaction mixture was stirred at 50° C. for 1 hour, and the temperature was lowered to room temperature. Subsequently, 200 ml of water and 120 ml of acetone were added to the reaction solution thus obtained, and 164.91 g (0.6681 mol) of tetradecanoyl chloride was dropwise added thereto over a period of 1 hour while stirring. During the dropwise addition of the tetradecanoyl chloride, the reaction system was maintained at a pH of from 9 to 11 by dropwise adding a 30% aqueous solution of NaOH while the temperature was maintained at 5 to 30° C. After the completion of the dropwise addition, the reaction mixture was stirred at room temperature for 1 hour. Then, 50 ml of ethanol and a 30% aqueous solution of NaOH were added thereto. The 30% aqueous solution of NaOH was added in an amount such that the sum of the amount of NaOH and that previously added for pH adjustment was 75.67 g (1.892 mol). Thereafter, the reaction solution was stirred at 90° C. for 3 hours. During this period, nitrogen gas was blown into the reaction solution, thereby continuously eliminating generated ammonia gas from the system. Thereafter, the reaction solution was cooled to room temperature, and the pH thereof was adjusted to 1.0 with concentrated hydrochloric acid. A formed white precipitate was separated by filtration, washed with water and dried. Thus, 229.16 g (yield from glycine: 96.2%) of a white powder of N-carboxyethyl-N-tetradecanoylglycine represented by the following formula was obtained. ##STR29##

Provenance & Evidence