Trifluoromethanesulfonic acid → Distearyl dimethyl ammonium trifluoromethyl sulfonate

HRID 1196451Notes

Reaction equation

HRID 1196451 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3]([OH:6])(=[O:5])=[O:4].COS([O-])(=O)=O.[CH2:15]([N+:33]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])([CH3:35])[CH3:34])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>O>[F:1][C:2]([S:3]([O-:6])(=[O:5])=[O:4])([F:8])[F:7].[CH2:36]([N+:33]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])([CH3:35])[CH3:34])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53]

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acid2×HCID 77450Dimethyldioctadecylammonium methyl sulfate

Product 1

HCID 18186058Distearyl dimethyl ammonium trifluoromethyl sulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 500 milliliters of water was cautiously added 43 milliliters (72.9 grams, 0.486 mol) of trifluoromethane sulfonic acid, CF3SO3H (3M Corporation, Fluorad FC-24, anhydrous). This solution was cooled to room temperature then added to a suspension of distearyl dimethyl ammonium methyl sulfate (DDAMS) (150 grams, 0.227 mol) in 600 milliliters water. The mixture was heated on a hot plate with stirring (80° to 90° C.) for 4 hours, cooled to room temperature and allowed to stand overnight (16 hours). The mixture had separated into a tan solid layer atop the aqueous layer. The solid layer was broken up and the aqueous phase removed by filtration under reduced pressure. The tan solid was washed with water then air dried for 1 hour. The crude material was recrystallized from acetone to afford 114.7 grams (0.164 mol, 72 percent theory), m.p. 90° C. (soften), 119° C. (liquid) of the above trifluoromethane sulfonate salt (DDATRIF), as an off-white powder. A second crop, 17 grams of a tan-yellow solid, was unacceptable for use without further extensive purification.

Workup

  1. temperatureThe mixture was heated on a hot plate
  2. temperaturecooled to room temperature
  3. waitto stand overnight
  4. custom(16 hours)
  5. customThe mixture had separated into a tan solid layer atop the aqueous layer
  6. customthe aqueous phase removed by filtration under reduced pressure
  7. washThe tan solid was washed with water
  8. customair dried for 1 hour
  9. customThe crude material was recrystallized from acetone

Sources & evidence

ORD record
ord-f2883ea9c3624f14ab451980f5d52ef5
Source dataset
uspto-grants-1992_05
Patent number
US05114821

Reaction notes

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