Hydrogen Peroxide → Azelaic Acid

HRID 861669Notes

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.[OH2:43]>[Co](Cl)Cl>[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:43].[C:21]([OH:40])(=[O:39])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

Conditions

Temperature: 70 °C

Procedure

Using the same apparatus as in Example 1, 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. The crude reaction product so obtained is charged into an stirred 500 ml autoclave containing 150 ml of water and 1.0 g of hydrous cobalt chloride. The autoclave is then pressurised with 65 atm of air and the temperature is raised to 70° C. The reaction mixture is treated according to the way described in example 1 obtaining 42 g of azelaic acid (yield=70%) and 30.9 g of pelargonic acid (yield=69%).

Workup

additionis added
customis brought to 60°-65° C.
temperatureto maintain the temperature between 65°-75° C
customThe crude reaction product
customso obtained
additionis charged into an stirred 500 ml autoclave
additionThe reaction mixture is treated

Sources & evidence

ORD record: ord-abb9eac2712f41f7bad0a8b5acc023cc
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05714623

Reaction notes

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