Acrylonitrile → HCID 23466163, compound

HRID 1701592Notes

Reaction equation

HRID 1701592 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([CH2:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[OH:20])[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][CH3:16].[C:39](#[N:42])[CH:40]=[CH2:41].[OH-].[Na+].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[CH2:23]([O:22][CH2:21][CH:19]([CH2:18][O:17][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][CH3:16])[O:20][CH2:41][CH2:40][C:39]#[N:42])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

6

Reactant 4

HCID 7855Acrylonitrile2×HCID 14798Sodium Hydroxide2×HCID 845961,3-Bis(hexadecyloxy)propan-2-olHCID 2723671Tetrabutylammonium Hydroxide2×

Product 1

HCID 23466163HCID 23466163, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 1,3-di-O-(n-hexadecyl)-glycerol (80 g., 148 mmoles), acrylonitrile (1.49 kg., 28.1 moles) and aqueous 2 N sodium hydroxide (1.2 l.) was heated to 50° C. Tetrabutylammonium hydroxide (19.2 g. of 40 wt. % aqueous solution, 29.15 mmoles) was slowly added, causing the temperature of the exothermic reaction mixture to rise to about 80° to 90° C. The reaction mixture was then stirred for 20 minutes without any external heating, followed by cooling to 20° C. and addition of water (1.0 l.). A solid material, a mixture of unreacted and cyanoethylated 1,3-di-O-(n-hexadecyl)-glycerol, was isolated and treated again with fresh acrylonitrile (1.49 kg., 28.1 moles), aqueous 2 N sodium hydroxide (1.2 l.) and tetrabutylammonium hydroxide (19.2 g. of 40 wt. % aqueous solution, 29.15 mmoles) for 20 minutes with stirring at 50° C., followed by cooling and addition of water (1.0 l.). The resulting 1,3-di-O-(n-hexadecyl)-2-O-(2-cyanoethyl)-glycerol solids were filtered, washed consecutively with water, methanol and acetonitrile, and dried [82 g., 93% yield, m.p. 45°-46° C., ir (CHCl3) 2250 cm-1, n.m.r. (CDCl3) δ 3.92 (t, 2, NCCH2CH2O--), 3.33-3.67 (m, 9, --OCH[CH2OCH2C15H31 ]2), 2.62 (t, 2, NCCH2CH2O--) and 0.75-1.58 (m, 62, aliphatic protons)].

Workup

  1. customto rise to about 80° to 90° C
  2. temperatureby cooling to 20° C.
  3. customwas isolated
  4. stirringwith stirring at 50° C.
  5. temperatureby cooling
  6. filtrationThe resulting 1,3-di-O-(n-hexadecyl)-2-O-(2-cyanoethyl)-glycerol solids were filtered
  7. washwashed consecutively with water, methanol and acetonitrile
  8. customdried [82 g

Sources & evidence

ORD record
ord-f9f24bd64adc4126989ba04bf6ade074
Source dataset
uspto-grants-1980_03
Patent number
US04193999

Reaction notes

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