Hydrochloric Acid → Nonanoyl chloride

HRID 1835626Notes

Reaction equation

HRID 1835626 reaction equation
CN(C)C=O.[C:6]([OH:16])(=O)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(Cl)([Cl:19])=O.Cl>>[C:6]([Cl:19])(=[O:16])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6228DimethylformamideHCID 6371Phosgene2×HCID 8158Nonanoic Acid

Product 1

HCID 69819Nonanoyl chloride

Procedure

100.5 g (1.38 mol) of N,N-dimethylformamide were added to 2.75 mol of pelargonic acid in a stirred apparatus. The reaction solution was brought to a temperature of from 20 to 30° C. with stirring, and a total of 2.78 mol of gaseous phosgene and simultaneously 1.92 mol of gaseous hydrogen chloride were introduced under atmospheric pressure. When the addition of phosgene and hydrogen chloride was complete, the two phases were separated from one another. The catalyst phase comprised a molar proportion of the catalyst adduct, based on the molar amount of N,N-dimethylformamide plus catalyst adduct, of 1%. The carbonyl chloride phase comprised 98.9% by weight of pelargonoyl chloride and 0.04% by weight of pelargonic anhydride. The color number was 18 APHA.

Workup

  1. customwas brought to a temperature of from 20 to 30° C.
  2. customthe two phases were separated from one another

Sources & evidence

ORD record
ord-11a31c5819d54f32add734095e3aecb1
Source dataset
uspto-grants-2004_08
Patent number
US06770783B1

Reaction notes

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