Methyloxirane propene oxide

Chemical Designations - Synonyms 1,2-Epoxypropane Methyloxirane propene oxide Chemical Formula CH3CHCH2O. 

Turning to current work employing gold catalysts, the reaction that has attracted most attention is the oxidation of propene to methyloxirane (propene oxide or 1,2-epoxypropane).2 While silver catalysts work very well for epoxidising ethene, they fail utterly with propene, because the selective intermediate is more reactive than the reactant, and carbon dioxide alone... 

Current commercial production of methyloxirane (propene oxide), used extensively in the production of polyurethanes, is usually based on a chloro-hydrin process. However, the direct gas-phase synthesis of methyloxirane... 

The major products from methyloxirane (propene oxide) are C2H5CHO, CH3COCH3 and CH2=CHCH20H [90], Similarly, isobutyraldehyde is the dominant product from isobutene oxide. Oxetanes are known to undergo homolysis through ring splitting, so that isobutene and HCHO are major products from 3,3-dimethyloxetane. 

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

SYNONYMS 1,2-epoxypropane, methyloxirane, propene oxide, propylene epoxide. 

Synonyms/Trade Names 1.2-Epoxy propane Methyl ethylene oxide Methyloxirane Propene oxide 1.2-Propylene oxide ... 

Synonyms 1,2-Epoxypropane Methyloxirane propene oxide Chemical Formula CHjCHCHjO (ii) Observable Characteristics — Physical State (as normally shipped) Liquid Color Colorless Odor Ethereal characteristic sweet, alcoholyc like namral gas (iii) Physical and Chemical Properties — Physical State at 15 °C and 1 atm Liquid Molecular Weight 58.08 Boiling Point at I atm 93.7, 34.3, 307.5 Freezing Point -169.4, -11.9, 16i.3 Critical Temperature 408.4, 209.1 482.3 Critical P-essure 714, 48.6, 4.92 Specific Gravity 0.830 at 20°C Vapor (Gas) Density 2.0 Ratio of Specific Heats of Vapor (Gas) 1.133 Im-tent Heat of Vaporization 205, 114, 4.77 Heat of Combustion -13.CKX), -7.221, -302.3 Heat of Decomposition Not pertinent (iv) Health Hazards Information... 

Recently (79MI50500) Sharpless and coworkers have shown that r-butyl hydroperoxide (TBHP) epoxidations, catalyzed by molybdenum or vanadium compounds, offer advantages over peroxy acids with regard to safety, cost and, sometimes, selectivity, e.g. Scheme 73, although this is not always the case (Scheme 74). The oxidation of propene by 1-phenylethyl hydroperoxide is an important industrial route to methyloxirane (propylene oxide) (79MI5501). 

The manufacture and uses of oxiranes are reviewed in (B-80MI50500, B-80MI50501). The industrially most important oxiranes are oxirane itself (ethylene oxide), which is made by catalyzed air-oxidation of ethylene (cf. Section 5.05.4.2.2(f)), and methyloxirane (propylene oxide), which is made by /3-elimination of hydrogen chloride from propene-derived 1-chloro-2-propanol (cf. Section 5.05.4.2.1) and by epoxidation of propene with 1-phenylethyl hydroperoxide cf. Section 5.05.4.2.2(f)) (79MI50501). 

Synonyms AI3-07541 BRN 0079763 Caswell No. 713A CCRIS 540 EINECS 200-879-2 EPA pesticide chemical code 042501 Epoxypropane 1,2-Epoxypropane Methyl ethylene oxide Methyloxirane NC1-C50099 Propene oxide 1,2-Propylene oxide UN 1280. 

Synonyms 1,2-Epoxypropane propene oxide methyloxirane propylene epoxide... 

Methyloxirane (propylene oxide) is a colourless, water-miscible liquid, bp 35°C. It is produced commercially from propene and tert-hMtyX hydroperoxide in the presence of molybdenum acetylacetonate [8]. 

Propene oxide (PO, lUPAC nomenclature 2-methyloxirane) is an important chemical feedstock, having a world annual production capacity of about 7 mUhon tons [1]. It is processed into the major products, polyurethane polyols and propylene glycol [2]. The former are used in the manufacture of polyurethane foams and the latter for antifreeze (safer than ethylene glycol), drugs, cosmetics etc. 

Synonyms Epoxypropane 1,2-Epoxypropane 2,3-Epoxypropane Methyl ethylene oxide Methyloxacyclopropane Methyloxirane S(-)-Methyloxlrane Propane, 1,2-epoxy- Propene oxide Propylene epoxide 1,2-Propylene oxide Empirical CsHeO... 

One method for the preparation of epoxides from alkenes involves (1) treating the alkene with chlorine or bromine in water to form a chlorohydrin (or bromohydrin) followed by (2) treating the halohydrin with a base to bring about intramolecular displacement of Cl . These steps convert propene first to l-chloro-2-propanol and then to methyloxirane (propylene oxide). 

Propene oxide (methyl oxirane) is used on a large scale for the production of polyurethanes and is usually made using a chlorohydrin process. A greener alternative would be to use the direct gas-phase synthesis of methyloxirane from propene, using molecular oxygen in the presence of... 

Further advantages are the small holdup and the short contact time. Klemm et al. [99] applied microstructured film contactors for the evaporation of hydrogen peroxide that was then used for the partial oxidation of propene to methyloxirane. 

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