Hydrochloric Acid → Dodecanoyl chloride

HRID 714008Notes

Reaction equation

HRID 714008 reaction equation
[C:1]([OH:14])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].S(Cl)([Cl:17])=O.Cl.S(=O)=O>>[C:1]([Cl:17])(=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 3893Lauric AcidHCID 24386Thionyl Chloride

Product 1

HCID 8166Dodecanoyl chlorideYield 97.1%

Procedure

To a stirred mass of lauric acid (200 g, 0.999 gmol) and sodium N-lauroyl, N-methyl taurate (0.6 g, 0.0017 gmol) at 25° C. under nitrogen blanket, thionyl chloride (123 g, 1.03 gmol) was added slowly at 25° C. and atmospheric pressure over a period of 2 hours maintaining temperature below 25° C. The hydrochloric acid and sulfur dioxide generated during the process was continuously scrubbed in a gas scrubber containing caustic lye. The reaction mixture was stirred for additional 4 hours at the reaction temperature. The progress of reaction in the last phase was monitored by measuring alkanoyl chloride formation. Nitrogen gas was purged through the reaction mass for 3 hours to remove the residual traces of sulfur dioxide, hydrogen chloride gas and unreacted thionyl chloride. At the end of this procedure lauroyl chloride (212 g, 97%) was obtained as practically colorless product. The detailed analysis is given in the Table 13.

Workup

  1. temperatureatmospheric pressure over a period of 2 hours maintaining temperature below 25° C
  2. additioncontaining caustic lye
  3. customThe progress of reaction in the last phase
  4. customNitrogen gas was purged through the reaction mass for 3 hours
  5. customto remove the residual traces of sulfur dioxide, hydrogen chloride gas and unreacted thionyl chloride

Sources & evidence

ORD record
ord-fa57391c33474d98b9003a55e1b38279
Source dataset
uspto-grants-2015_11
Patent number
US09187407B2

Reaction notes

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