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Tetraethylenepentamine → Tetraethylenepentamine

HRID 1603379
Notes
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Reaction equation

HRID 1603379 reaction equation
[CH:1](C1CC(=O)OC1=O)=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([CH:24]1[CH2:29][C:28](=[O:30])[NH:27][C:25]1=[O:26])=CCCCCCC.[NH2:31][CH2:32][CH2:33][NH:34][CH2:35][CH2:36][NH:37][CH2:38][CH2:39][NH:40][CH2:41][CH2:42][NH2:43]>O.C(O)(C)C>[CH:1]([N:27]1[C:28](=[O:30])[CH2:29][CH2:24][C:25]1=[O:26])=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[NH2:43][CH2:42][CH2:41][NH:40][CH2:39][CH2:38][NH:37][CH2:36][CH2:35][NH:34][CH2:33][CH2:32][NH2:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8197TetraethylenepentamineHCID 244423-Octenylsuccinic anhydrideHCID 695068213-(Oct-1-en-1-yl)pyrrolidine-2,5-dione

Product 2

HCID 8197TetraethylenepentamineHCID 702512701-(Oct-1-en-1-yl)pyrrolidine-2,5-dione

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
5×
HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

N-octenyl succinimide of tetraethylene pentamine was prepared by placing one mole of the amine in a reaction flask fitted with an addition funnel containing one mole of n-octenyl succinic anhydride, a water collector, a stirring and heating means and a reflux condenser. While the amine was stirred, the anhydride in the funnel was slowly added to the flask. Upon completion of the addition, the resulting reaction mixture was heated to about 142° C., whereupon water of reaction started to distill over. AT about 180° C., the resulting reaction product, viz., n-octenyl succinimide of tetraethylene pentamine, was a clear bright orange liquid. About one mole of water was collected in the collector, signifying that the imide-forming reaction was complete. The flask and its contents were then cooled to about 80° C., and sufficient isopropanol and distilled water were added to yield a solution which was 40 volume percent isopropanol, about 60 volume percent water and about 30 weight percent amide. Into this solution, based upon the total weight of the solution, about 1 weight percent mono-9-octadecenoate of poly (oxy-1,2-ethanediyl) sorbitol (about 20 ethanediyl groups) surfactant was added to facilitate effective dispersion of the imide agent when added to cooling water. The flask and its contents were maintained at about 80° C. with stirring until a clear solution resulted. The cooled solution was ready for use in accordance with the invention.

Workup

  1. customfitted with an addition funnel
  2. additionUpon completion of the addition
  3. customthe resulting reaction mixture
  4. distillationto distill over
  5. customAT about 180° C., the resulting reaction product, viz
  6. customforming
  7. customreaction
  8. distillationsufficient isopropanol and distilled water
  9. additionwere added
  10. customto yield a solution which
  11. additionwas added
  12. additionadded
  13. temperatureThe flask and its contents were maintained at about 80° C.
  14. customresulted

Sources & evidence

ORD record
ord-6ac7ebaa8b304c2cacb53b7c9f80e233
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05989322

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes