Ethylene Oxide → N-(2-Hydroxyethyl)succinimide

HRID 1657685Notes

Reaction equation

HRID 1657685 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH2:3][CH2:2]1.[CH2:8]1[O:10][CH2:9]1>[Cr].CC(CC(C)C)=O>[OH:10][CH2:9][CH2:8][N:5]1[C:4](=[O:6])[CH2:3][CH2:2][C:1]1=[O:7]

Participants

5

Reactant 2

HCID 6354Ethylene OxideHCID 11439Succinimide

Product 1

HCID 236334N-(2-Hydroxyethyl)succinimide

Reagents, catalysts & solvents 2

HCID 23976ChromiumCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

N-2-Hydroxyethyl succinimide was prepared by reacting 49.5g (0.5 mole) of succinimide with 26.5g (0.60 mole) of ethylene oxide in the presence of 0.49g (1%) of active chromium III tri-2-ethylhexanoate and 400 ml of methylisobutyl ketone for 2 hours at 160° to 165°C in an autoclave. N-2-Hydroxyethyl succinimide was obtained by filtration in 87.5% yield. The reaction did not proceed in the absence of COT.

Workup

  1. customN-2-Hydroxyethyl succinimide was prepared
  2. customfor 2 hours
  3. customat 160° to 165°C

Sources & evidence

ORD record
ord-37c077a467a445cfbef090db9de37147
Source dataset
uspto-grants-1976_06
Patent number
US03962182

Reaction notes

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