Potassium Succinate → Di(oleylmethyldihydroxyethylammonium) succinate

HRID 1461637Notes

Reaction equation

HRID 1461637 reaction equation
[Cl-].[CH2:2]([CH2:20][NH2+:21][CH2:22][CH:23]([OH:25])[OH:24])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[C:26]([O-:33])(=[O:32])[CH2:27][CH2:28][C:29]([O-:31])=[O:30].[K+].[K+]>C(O)C(C)C>[C:26]([O-:33])(=[O:32])[CH2:27][CH2:28][C:29]([O-:31])=[O:30].[CH2:2]([CH2:20][NH2+:21][CH2:22][CH:23]([OH:25])[OH:24])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[CH2:2]([CH2:20][NH2+:21][CH2:22][CH:23]([OH:25])[OH:24])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 164717Potassium SuccinateHCID 86745345Oleylmethyldihydroxyethylammonium chloride

Product 1

HCID 86745346Di(oleylmethyldihydroxyethylammonium) succinateYield 99.4%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

A four-necked flask fitted with stirrer and condenser means was charged with 81 g of oleylmethyldihydroxyethylammonium chloride, 20 g of potassium succinate and 200 g of isobutyl alcohol and the reaction was conducted at 40°-50° C. in an atmosphere of nitrogen gas introduced at a low flow rate for 6 hours. The precipitate was then collected by filtration and washed with 30 ml of isobutyl alcohol, and the filtrate and washings were combined and concentrated under reduced pressure. The residue was dissolved in 200 g of toluene and filtered and the filtrate was concentrated to give 82 g (theoretical yield 85.6 g) of di(oleylmethyldihydroxyethylammonium) succinate as a waxy product. The element analysis and IR data are shown below.

Workup

  1. customA four-necked flask fitted with stirrer and condenser means
  2. customwas conducted at 40°-50° C. in an atmosphere of nitrogen gas
  3. additionintroduced at a low flow rate for 6 hours
  4. filtrationThe precipitate was then collected by filtration
  5. washwashed with 30 ml of isobutyl alcohol
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in 200 g of toluene
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-65d25c045c694f3ca1bcfbd2b319c79d
Source dataset
uspto-grants-1991_12
Patent number
US05076828

Reaction notes

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