Cyanuric chloride → N,N',N''-trioctadecyl-1,3,5-triazine-2,4,6-triamine

HRID 498898

Reaktionsgleichung

Reaktionsgleichung von HRID 498898
[CH2:1]([NH2:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].COCCCO[CH2:26][CH2:27][CH2:28]OC.[C:31]([O-])(=O)[CH3:32].[Na+].[N:36]1[C:43](Cl)=[N:42][C:40](Cl)=[N:39][C:37]=1Cl>CC(O)C.C(O)(=O)C>[CH2:1]([NH:19][C:37]1[N:39]=[C:40]([NH:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[N:42]=[C:43]([NH:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:31][CH2:32][CH2:28][CH2:27][CH3:26])[N:36]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Komponenten

7

Edukt 4

HCID 7954Cyanuric chlorideHCID 15793OctadecylamineHCID 863021-Methoxy-3-(3-methoxypropoxy)propaneHCID 517045Sodium Acetate

Produkt 1

HCID 21758268N,N',N''-trioctadecyl-1,3,5-triazine-2,4,6-triamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Under a nitrogen atmosphere, a mixture of octadecylamine (389 grams, 1.44 mol), di(propylene glycol) dimethyl ether (1.50 liters), sodium acetate (134 grams, 1.63 mol), and cyanuric chloride (88.4 grams, 0.479 mol) was stirred for thirty minutes and then heated to 85° C. for two hours. The reaction mixture was heated to 155° C. at which temperature acetic acid was allowed to reflux out of the reaction mixture. The reaction mixture was heated to 170° C. for sixteen hours. 2-Propanol (1.60 liters) was added to the reaction mixture when it had cooled to 80° C. The precipitate was filtered at room temperature and washed with excess 2-propanol. The solid was stirred in refluxing water (2.00 liters) for two hours, filtered, and washed with excess water. The solid was stirred in refluxing 2-propanol (2.00 liters), filtered, and washed with excess 2-propanol to yield 377 grams of N,N′,N″-trioctadecyl-1,3,5-triazine-2,4,6-triamine as a white solid.

Aufarbeitung

  1. temperatureto reflux out of the reaction mixture
  2. temperatureThe reaction mixture was heated to 170° C. for sixteen hours
  3. temperaturehad cooled to 80° C
  4. filtrationThe precipitate was filtered at room temperature
  5. washwashed with excess 2-propanol
  6. stirringThe solid was stirred
  7. temperaturein refluxing water (2.00 liters) for two hours
  8. filtrationfiltered
  9. washwashed with excess water
  10. stirringThe solid was stirred
  11. temperaturein refluxing 2-propanol (2.00 liters)
  12. filtrationfiltered
  13. washwashed with excess 2-propanol

Quellen und Nachweise

ORD-Eintrag
ord-bf7af8a743ed4c7cba15bc741b3b5637
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07765698B2

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