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propylene oxide

Product name propylene oxide
Synonyms 2-epoxypropane
methyloxirane
1,2-propylene oxide
GOST 23001-88
CAS 75-56-9

Propylene oxide is a colorless, clear, volatile, flammable liquid with an ether-like odor. It is soluble in most organic solvents; boundedly soluble in water.

Propylene oxide molecule contains an asymmetrical carbon atom, so it is chiral compound which can exist in two enantiomer forms. Industrial propylene oxide is a racemic mixture of these isomers.

Oxirane structure provides easiness of addition reactions. Propylene oxide readily reacts with water to give propylene glycol. Reaction with phenols and alcohols results in propylene glycol esters. Propylene oxide can be isomerized into propionic aldehyde, allyl alcohol and acetone in the presence of SiO2, Al2O3 at 240-500°C. Lewis acids promote propylene oxide polymerization into polypropyleneoxide. Propylene oxide copolymers with ethylene oxide and propylene glycol have an industrial usage also.

Production.

There are two main routes to produce propylene oxide:

  • peroxide method - propylene oxidation with hydroperoxide of isobutane and ethylbenzene. A variety of this route is SM/PO process - styrene monomer/propylene oxide preparation. This process consists of three steps. At the first stage ethylbenzene is oxidized with oxygen of air at 130°C to form hydroperoxide. Then hydroperoxide reacts with propylene at 90-100°C and pressure 1.6-6.5 MPa in the presence of molibdenum catalyst to give propylene oxide and α-phenylethanol. After the separation of this mixture the phenylethanol is dehydrated to form styrene:

    C6H5CH2CH3 + O2 → C6H5CH(OOH)CH3

    C6H5CH(OOH)CH3 + CH3CH=CH2 → C6H5CH(OH)CH3 + CH3CHCH2O

    C6H5CH(OH)CH3 → C6H5CH=CH2 + H2O


  • chlorohydrin method (propylene --> propylene chlorohydrin --> propylene oxide);

    Uses.

  • as a starting material in making propylene glycol, propylene carbonate, isopropanolamines, propylene sulfide;
  • to make polyether polyols used for surfactants and oil demulsifiers;
  • as a raw material in synthesis of polypropyleneoxide itself and copolymers;
  • to synthesize ropylene glycol ethers;
  • as an intermediate in preparation of polyurethanes, polyester resins;

  • Manufacturer(s) JSC "Nizhnekamskneftekhim" Inc.
    Chemical structure of propylene oxide

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