Lauryl alcohol ethylene oxide → Oleylmethyldihydroxyethylammonium laurylethoxyethyl phosphate

HRID 1461645Notes

Reaction equation

HRID 1461645 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].[P:26]([O-:47])([O-:46])([O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[O:27].[K+].[K+].C(O)CCCCCCCCCCC.C1OC1>C(O)(C)C>[CH2:34]([CH2:33][CH2:32][O:31][CH2:30][CH2:29][O:28][P:26]([O-:47])([O-:46])=[O:27])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45].[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

5

Reactant 3

HCID 14122790Lauryl alcohol ethylene oxideHCID 86745345Oleylmethyldihydroxyethylammonium chlorideHCID 87761845Potassium monolaurylethoxyethyl phosphate

Product 1

HCID 131717135Oleylmethyldihydroxyethylammonium laurylethoxyethyl phosphateYield 96.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A four-necked flask fitted with stirrer and condenser means was charged with 40.5 g of oleylmethyldihydroxyethylammonium chloride, 21.5 g of potassium monolaurylethoxyethyl phosphate prepared from lauryl alcohol-ethylene oxide (2 mol) adduct and 150 g of isopropyl alcohol and the reaction was conducted at 75°-80° C. in an atmosphere of nitrogen gas introduced at a low flow rate for 8 hours. The precipitate was then collected by filtration and washed with 50 ml of isopropyl alcohol. The filtrate and the washings were combined and concentrated under reduced pressure and the residue was dissolved in 200 g of benzene and filtered. The filtrate was then concentrated to give 51.27 g (theoretical yield 54.55 g) of oleylmethyldihydroxyethylammonium laurylethoxyethyl phosphate as a waxy product. The elemental analysis is shown below.

Workup

  1. customA four-necked flask fitted with stirrer and condenser means
  2. customwas conducted at 75°-80° C. in an atmosphere of nitrogen gas
  3. additionintroduced at a low flow rate for 8 hours
  4. filtrationThe precipitate was then collected by filtration
  5. washwashed with 50 ml of isopropyl alcohol
  6. concentrationconcentrated under reduced pressure
  7. dissolutionthe residue was dissolved in 200 g of benzene
  8. filtrationfiltered
  9. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-80658ef5b4b94f20a7ce708a1c44e382
Source dataset
uspto-grants-1991_12
Patent number
US05076828

Reaction notes

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