# Halcon process

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In [chemistry](/source/chemistry), the '''Halcon process''' refers to technology for the production of [propylene oxide](/source/propylene_oxide) by oxidation of [propylene](/source/propylene) with  [tert-butyl hydroperoxide](/source/tert-butyl_hydroperoxide).  The reaction requires metal [catalyst](/source/catalyst)s, which typically contain [molybdenum](/source/molybdenum):<ref name=Patai />
:(CH<sub>3</sub>)<sub>3</sub>COOH  +  CH<sub>2</sub>=CHCH<sub>3</sub>  → (CH<sub>3</sub>)<sub>3</sub>COH  +  CH<sub>2</sub>OCHCH<sub>3</sub> 
The byproduct [tert-butanol](/source/tert-butanol) is recycled or converted to other useful compounds.  The process once operated at the scale of >2 billion kg/y.

The lighter analogue of propylene oxide, [ethylene oxide](/source/ethylene_oxide), is produced by silver-catalyzed reaction of [ethylene](/source/ethylene) with [oxygen](/source/oxygen).  Attempts to implement this relatively simple technology to the conversion of [propylene](/source/propylene) to [propylene oxide](/source/propylene_oxide) fail.  Instead only combustion predominates.  The problems are attributed to the sensitivity of [allylic](/source/allylic) C-H bonds.

==Mechanism==
The oxidation is thought to proceed by formation of Mo(η<sup>2</sup>-O<sub>2</sub>-tert-Bu) complexes.  The peroxy O center is rendered highly electrophilic, leading to attack on the alkene.<ref name=Mechanism />

==History==
The Halcon process was developed by [Halcon International](/source/Halcon_International).<ref name=Society />

==References==
<references>
<ref name=Society>{{cite journal |doi=10.1021/cen-v059n007.p016|title=Ralph Landau wins 1981 Perkin Medal|year=1981|last1=Fallwell|first1=William|journal=Chemical & Engineering News Archive|volume=59|issue=7|page=16}}</ref>
<ref name=Mechanism>{{cite journal |doi=10.1016/0920-5861(87)80012-3|title=D<sup>0</sup> [''sic''] metal peroxides as homolytic and heterolytic oxidative reagents. Mechanism of the Halcon Epoxidation Process|year=1987|last1=Mimoun|first1=Hubert|journal=Catalysis Today|volume=1|issue=3|pages=281–295}}</ref>
<ref name=Patai>{{cite book |title=Peroxides|chapter= Syntheses and Uses of Hydroperoxides and Dialkylperoxides |editor1-first= Saul |editor1-last= Patai | first= Roger&nbsp;A. |last=Sheldon |year= 1983 |publisher= John Wiley & Sons |doi= 10.1002/9780470771730.ch6|series=Chemistry of Functional Groups}}</ref>
</references>

Category:Catalysis

{{Catalysis-stub}}

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