Ammonia → Glycine

Temperature

45 °C

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##

1. customequipped with a stirrer
2. temperaturea thermometer and a dropping funnel, and heated
3. stirringwhile stirring
4. additionDuring the dropwise addition
5. additionAfter the completion of the dropwise addition
6. stirringthe reaction mixture was stirred at 50° C. for 1 hour
7. customwas lowered to room temperature
8. customthus obtained
9. stirringover a period of 1 hour while stirring
10. temperaturethe reaction system was maintained at a pH of from 9 to 11
11. temperaturewas maintained at 5 to 30° C
12. additionAfter the completion of the dropwise addition
13. stirringthe reaction mixture was stirred at room temperature for 1 hour
14. additionthat previously added for pH adjustment
15. stirringThereafter, the reaction solution was stirred at 90° C. for 3 hours
16. waitDuring this period
17. temperatureThereafter, the reaction solution was cooled to room temperature
18. customA formed white precipitate was separated by filtration
19. washwashed with water
20. customdried

ORD record

ord-a69ba2f05e634d22b6b49df41ca69d36

Source dataset

uspto-grants-2000_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06121470