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Industrial production of propylene oxide starts from propylene. [8] Two general approaches are employed, one involving hydrochlorination and the other involving oxidation . [ 9 ] In 2005, about half of the world production was through chlorohydrin technology and one half via oxidation routes.
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 to propylene oxide fail. Instead only combustion predominates. The problems are attributed to the sensitivity of allylic C-H bonds.
Cumene hydroperoxide is involved as an organic peroxide in the production of propylene oxide by the oxidation of propene. This technology was commercialized by Sumitomo Chemical. [6] The oxidation by cumene hydroperoxide of propene affords propylene oxide and the byproduct 2-phenylpropan-2-ol. The reaction follows this stoichiometry: CH 3 CHCH ...
Propylene is also used to produce isopropyl alcohol (propan-2-ol), acrylonitrile, propylene oxide, and epichlorohydrin. [18] The industrial production of acrylic acid involves the catalytic partial oxidation of propylene. [19] Propylene is an intermediate in the oxidation to acrylic acid.
This process converts two relatively cheap starting materials, benzene and propylene, into two more valuable ones, phenol and acetone. Other reactants required are oxygen from air and small amounts of a radical initiator. Most of the worldwide production of phenol and acetone is now based on this method.
Hexafluoropropylene oxide (HFPO) is an intermediate used in industrial organofluorine chemistry; specifically it is a monomer for fluoropolymers.This colourless gas is the epoxide of hexafluoropropylene, which is a fluorinated analog of propylene oxide, HFPO is produced by Chemours and 3M and as a precursor to the lubricant Krytox and related materials.
Acrylonitrile is produced by catalytic ammoxidation of propylene, also known as the SOHIO process. In 2002, world production capacity was estimated at 5 million tonnes per year, [5] [8] rising to about 6 million tonnes by 2017. [9] Acetonitrile and hydrogen cyanide are significant byproducts that are recovered for sale. [5]
Allyl alcohol can also be made by the rearrangement of propylene oxide, a reaction that is catalyzed by potassium alum at high temperature. The advantage of this method relative to the allyl chloride route is that it does not generate salt. Also avoiding chloride-containing intermediates is the "acetoxylation" of propylene to allyl acetate: