Ammonia → Eicosenyl succinimide

HRID 848408Notes

Reaction equation

HRID 848408 reaction equation
[CH:1]([CH:21]1[CH2:26][C:25](=[O:27])O[C:22]1=[O:23])=[CH: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][CH2:18][CH2:19][CH3:20].[NH3:28]>>[CH:1]([CH:21]1[CH2:26][C:25](=[O:27])[NH:28][C:22]1=[O:23])=[CH: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][CH2:18][CH2:19][CH3:20]

Participants

3

Reactant 2

HCID 222Ammonia2×HCID 54069643Eicosenyl succinic anhydride

Product 1

HCID 70518590Eicosenyl succinimide

Conditions

Temperature
160 °C

Procedure

In another reaction vessel was placed 570 grams of the above isomerized eicosenyl succinic anhydride. This was heated to 160° C. and ammonia injection started. The temperature rose to 175° C. Ammonia injection was continued at 175° C. until the temperature dropped. Then 30" Hg vacuum was slowly applied to distill out water and ammonia. Additional ammonia was injected to be sure no anhydride remained. There was no further reaction so this ammonia was stripped out at 30" Hg vacuum at 170° C. yielding isomerized eicosenyl succinimide. This can then be reacted with formaldehyde as in Example 2 to form N-hydroxymethyl isomerized eicosenyl succinimide.

Workup

  1. customIn another reaction vessel was placed
  2. customrose to 175° C
  3. customwas continued at 175° C. until the temperature
  4. additiondropped
  5. distillationto distill out water and ammonia
  6. customno further reaction so this ammonia
  7. customwas stripped out at 30" Hg vacuum at 170° C.

Sources & evidence

ORD record
ord-3599de2c841a4a1483e1fe142982c437
Source dataset
uspto-grants-1981_10
Patent number
US04295983

Reaction notes

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