Halcon process
In chemistry, the Halcon process refers to technology for the production of propylene oxide by oxidation of propylene with tert-butyl hydroperoxide. The reaction requires metal catalysts, which are typically contain molybdenum:[1]
- (CH3)3COOH + CH2=CHCH3 → (CH3)3COH + CH2OCHCH3
The byproduct tert-butanol is recycled or converted to other useful compounds.
The lighter analogue of propylene oxide, ethylene oxide, is produced by silver-catalyzed reaction of ethylene with oxygen. Attempts to implement this relatively simple technology to the conversion of propylene oxide to propylene oxide fail. Instead only combustion predominates. The problems are attributed to the sensitivity of allylic C-H bonds.
Mechanism
The oxidation is thought to proceed by formation of Mo(η2-O2-tert-Bu) complexes. The peroxy O center is rendered highly electrophilic, leading to attack on the alkene.[2]
References
- ^ Roger A. Sheldon (1983). Patai, Saul (ed.). Syntheses and Uses of Hydroperoxides and Dialkylperoxides. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. doi:10.1002/9780470771730.ch6.
- ^ Mimoun, Hubert (1987). "Do metal peroxides as homolytic and heterolytic oxidative reagents. Mechanism of the Halcon Epoxidation Process". Catalysis Today. 1 (3): 281–295. doi:10.1016/0920-5861(87)80012-3.