Hydrochloric Acid → 2,3-Dihydroxypropyloctyldimethylammonium chloride

HRID 522247

Reaction equation

HRID 522247 reaction equation
[Cl:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[CH3:7][N:8]([CH3:17])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[OH-].[Na+].Cl.CN(C)C>>[Cl-:1].[OH:6][CH:3]([CH2:4][OH:5])[CH2:2][N+:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])([CH3:7])[CH3:17]

Participants

6

Reactant 5

HCID 313Hydrochloric Acid3×HCID 1146TrimethylamineHCID 72903-Chloro-1,2-propanediolHCID 14798Sodium Hydroxide2×HCID 16224Dimethyloctylamine

Product 1

HCID 900247032,3-Dihydroxypropyloctyldimethylammonium chloride

Conditions

Temperature
30 °C

Procedure

In a 2 L reactor system 358.81 g of 3-chloro-1,2-dihydroxypropane (99.3%, 3.22 moles) is added to 734.20 g distilled water. The solution is heated to 30° C. and 496.29 g dimethyloctylamine (98.5%, 3.11 moles) is added over 60 minutes while the reaction solution is being mixed with a mechanical stirrer. The pH is 8.9 and 3.83 g sodium hydroxide (50%) is added to increase the pH to 9.9. The reaction solution is mixed for one hour and then the temperature is increased to 50° C. After another hour the reaction solution is a “milky white” and the pH is 8.3. 19.6 g sodium hydroxide (50%) is added to increase the pH to 9.5. After four additional hours of mixing at 50° C. the pH is 11.7; 11.97 g concentrated hydrochloric acid is added to decrease the pH to 9.0. Thirty minutes later 3.30 g of concentrated hydrochloric acid is added to decrease the pH to 8.9. The solution is allowed to stir for 16 hours at 50° C. The reaction solution pH is 10.7 and 2.58 g concentrated hydrochloric acid is added to reduce the pH to 8.0. The temperature is reduced to 20° C. and 24.23 g trimethylamine (43.6%) is added and allowed to mix at room temperature for five hours. The temperature is increased to 40° C. and the pH is increased to 9.5 and the reaction solution is purged with nitrogen overnight. The solution is pH adjusted to 6.5 with concentrated hydrochloric acid. The isolated product has the following structure:

Workup

  1. distillationdistilled water
  2. additionis being mixed with a mechanical stirrer
  3. temperatureto increase the pH to 9.9
  4. additionThe reaction solution is mixed for one hour
  5. temperaturethe temperature is increased to 50° C
  6. waitAfter another hour the reaction solution is
  7. temperatureto increase the pH to 9.5
  8. additionAfter four additional hours of mixing at 50° C. the pH is 11.7
  9. customis reduced to 20° C.
  10. additionto mix at room temperature for five hours
  11. temperatureThe temperature is increased to 40° C.
  12. temperaturethe pH is increased to 9.5
  13. customthe reaction solution is purged with nitrogen overnight

Sources & evidence

ORD record
ord-4c09b81d47124a5fb53fd37dc6c728b5
Source dataset
uspto-grants-2016_05
Patent number
US09328279B2

Linked notes

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