Stearic Acid → Stearoyl chloride

HRID 611954Notes

Reaction equation

HRID 611954 reaction equation
[C:1]([OH:20])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(Cl)([Cl:23])=O>ClC1C=CC=CC=1>[C:1]([Cl:23])(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 5281Stearic AcidHCID 6371Phosgene

Product 1

HCID 8212Stearoyl chloride

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
25 °C

Procedure

170.4 g (0.6 mol) of stearic acid and 890 g of monochlorobenzene are introduced into the reactor and 594 g (6 mol) of phosgene are then added over about 30 minutes, while maintaining the temperature of the reaction medium at a maximum of 25° C. The set pressure is adjusted to 10.5 bar relative. The reaction medium is heated to 120° C. and is maintained at this temperature for 1 hour 30 minutes and is then heated to 150° C. and maintained at this new temperature for 1 hour. The level of residual acid is then about 1.4 mol %, the level of residual anhydride is zero and the level of stearoyl chloride obtained 98.6 mol %. The maximum pressure reached was 9 bar relative.

Workup

  1. additionare then added over about 30 minutes
  2. temperatureThe reaction medium is heated to 120° C.
  3. temperatureis maintained at this temperature for 1 hour 30 minutes
  4. temperatureis then heated to 150° C.
  5. temperaturemaintained at this new temperature for 1 hour

Sources & evidence

ORD record
ord-1dd2867247af4de08408e648e14a728f
Source dataset
uspto-grants-1999_12
Patent number
US06002043

Reaction notes

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