Propylene Oxide 1,2-Epoxypropane

There are two important methods for the manufacture of propylene oxide, each accounting for one half the total amount produced. The older method involves chlorohydrin formation from the reaction of propylene with chlorine water. Before 1969 this was the exclusive method. Unlike the analogous procedure for making ethylene oxide from ethylene, which now is obsolete, this method for propylene oxide is still economically competitive. Many old ethylene oxide plants have been converted to propylene oxide synthesis. 

The mechanism in the first step involves an attack of the electrophilic chlorine on the double bond of propylene to form a chloronium ion, which is attacked by a hydroxide ion to complete the first reaction. The dilute 

A new variation of the chlorohydrin process uses t-butyl hypochlorite as chlorinating agent. The waste brine solution can be converted back to chlorine and caustic by a special electrolytic cell to avoid the waste of chlorine. 

The second manufacturing method for propylene oxide is via peroxidation of propylene, called the Halcon process after the company that invented it. Oxygen is first used to oxidize isobutane to r-butyl hydroperoxide (BHP) over a molybdenum naphthenate catalyst at 90°C and 450 psi. This oxidation occurs at the preferred tertiary carbon because a tertiary alkyl radical intermediate can be formed easily. 

The BHP is then used to oxidize propylene to the oxide. This reaction is ionic and its mechanism follows. The yield of propylene oxide from propylene is 90%. 

---

Propylene oxide 1,2-Epoxypropane 2-Methyloxirane 2-Methyloxacyclopropane Cyclohexene oxide 1,2-Epoxycyclohexane 7-Oxabicyclo[4.1.0]heptane ... 

Propylene Oxide (1,2-Epoxypropane, Methyl-oxirane or Prepene Oxide). 

Propylox [Propylene oxidation] A process for epoxidizing propylene to propylene oxide (1,2-epoxypropane),... 

Synonyms 1,2-Propylene oxide 1,2-Epoxypropane Methyloxacyclopropane Methyloxirane Methyl ethylene Oxide... 

Propylene Oxide 1,2-Epoxypropane Methyloxirane Propene Oxide ... 

Propylene oxide n. CH3CH(0)CH2 (1,2 -propylene oxide, 1,2 epoxypropane). A low boiling, liquid epoxide compound derived from the intermediate propylene chlorohy-drin, which is itself produced by reacting propylene with chlorine and water. Propylene oxide is an important intermediate for the manufacture of polyglycols used for polyurethane foams and resins, and polyester resins. 

Propylene oxide (1,2-epoxypropane) Dehydrator, diluent for epoxy resin 1% Ethanol 75-56-9 C3H60... 

Propylene oxide 1,2-epoxypropane, 1, 2-propylene oxide, methyl oxirane, methyl ethylene oxide, propileno oxido (Spanish), oxyde de propylene (French)... 

---