Hydrogen Peroxide → Azelaic Acid

HRID 861668Notes

Reaction equation

HRID 861668 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=C\CCCCCCCC.[C:21]([OH:40])(=[O:39])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=C\C/C=C\CCCCC.OO.O=O.[OH2:45]>C([O-])(=O)C.[Co+2].C([O-])(=O)C>[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:39])=[O:45].[C:21]([OH:40])(=[O:39])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

8

Reactant 5

HCID 784Hydrogen Peroxide3×HCID 962WaterHCID 977OxygenHCID 445639Oleic AcidHCID 5280450Linoleic Acid

Product 2

HCID 2266Azelaic AcidYield 70.9%HCID 8158Nonanoic AcidYield 70%

Reagents, catalysts & solvents 1

HCID 6277Cobalt diacetateCatalyst

Conditions

Temperature
70 °C

Procedure

Into a 500 ml round bottomed flask equipped with a mechanical stirrer, thermometer, dropping funnel, gas influx tube and a condenser, 100 g of crude oleic acid (80% purity) containing 9% linoleic acid and 0.75 g of H2WO4 is added. The stirred mixture is brought to 60°-65° C. and 28 g of 60% w/w H2O2 is added. The H2O2 is gradually added over about 30 mins in order to maintain the temperature between 65°-75° C. Once the addition of H2O2 is completed the mixture is left at that temperature for 1.5 hours. Then, 200 ml of water and 1 g of hydrous cobalt acetate is added to the mixture. The temperature is raised to 70° C. by passing an oxygen stream through the reactor bottom for 4 hours. At the end of the reaction, the reaction products are recovered by the process as described in example 1, obtaining 42.5 g of azelaic acid (yield=70.9%) and 31.3 g of pelargonic acid (yield=70%).

Workup

  1. customInto a 500 ml round bottomed flask equipped with a mechanical stirrer
  2. additionis added
  3. customis brought to 60°-65° C.
  4. temperatureto maintain the temperature between 65°-75° C
  5. custombottom for 4 hours
  6. customAt the end of the reaction
  7. customthe reaction products are recovered by the process

Sources & evidence

ORD record
ord-28db4b605d4f49c9be6cc669c688945b
Source dataset
uspto-grants-1998_02
Patent number
US05714623

Reaction notes

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