Sulfuric Acid → Azelaic Acid

HRID 363201

Reaction equation

HRID 363201 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])#N.[OH-:13].[Na+].S(=O)(=O)(O)[OH:16]>C(O)CO.COC.O>[C:10]([OH:12])(=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:1]([OH:16])=[O:13]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 110843008-Cyano-octanoic acid

Product 1

HCID 2266Azelaic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21863332Dimethyl ether ethylene glycolSolvent

Procedure

83.5 g of 8-cyanooctanoic acid dissolved in 300 ml of dimethyl ether ethylene glycol are heated to 130° C. for 4 hours in the presence of 50g of 40% caustic soda. After cooling, the reaction mixture is diluted with water, then acidified to pH 5 with diluted sulfuric acid, and then the precipitated solid is filtered. After drying, 92 g of azelaic acid with a m.p. of 107° C. are obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated solid is filtered
  3. customAfter drying

Sources & evidence

ORD record
ord-106c0db6ab624e2f871a05c8c526b87c
Source dataset
uspto-grants-1999_02
Patent number
US05872267

Linked notes

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