Dimethylformamide → Nonanoyl chloride

HRID 1835625Notes

Reaction equation

HRID 1835625 reaction equation
CN(C=O)C.[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>>[C:6]([Cl:19])(=[O:16])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 3

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 were introduced under atmospheric pressure. After the addition of phosgene 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 <0.05. The carbonyl chloride phase comprised 97.1 area % of pelargonoyl. chloride and 1.9 area % of pelargonic anhydride. The color number was 16 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-17e690c902b84e86a3bbb19904380f94
Source dataset
uspto-grants-2004_08
Patent number
US06770783B1

Reaction notes

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