EPOXYPROPANE

Both of these chlorohydrins are converted to 1,2-dihydroxypropane by heating with solutions of sodium hydrogen carbonate when heated with solid sodium hydroxide they give 1,2-epoxypropane. U.S. production 1976 4400 tonnes. 

Figure Bl.16.16. TREPR spectrum of TEMPO radicals in 1,2-epoxypropane solution with benzophenone, 1 ps after 308 inn laser flash. Reprinted from [45],...

Substitutive lUPAC nomenclature names epoxides as epoxy derivatives of alkanes According to this system ethylene oxide becomes epoxyethane and propylene oxide becomes 1 2 epoxypropane The prefix epoxy always immediately precedes the alkane ending it is not listed m alphabetical order like other substituents... 

A carbon atom in a ring can be a chirality center if it bears two different sub stituents and the path traced around the ring from that carbon m one direction is differ ent from that traced m the other The carbon atom that bears the methyl group m 1 2 epoxypropane for example is a chirality center The sequence of groups is O—CH2 as one proceeds clockwise around the ring from that atom but is CH2—O m the counter clockwise direction Similarly C 4 is a chirality center m limonene... 

Figure 7 7 shows why equal amounts of (R) and (5) 1 2 epoxypropane are formed m the epoxidation of propene There is no difference between the top face of the dou ble bond and the bottom face Peroxyacetic acid can transfer oxygen to either face with equal facility the rates of formation of the R and S enantiomers of the product are the same and the product is racemic... 

FIGURE 7 7 Epoxida tion of propene produces equal amounts of (/ ) and (S) 1 2 epoxypropane... 

About 2 X 10 Ib/year of 1 2 epoxypropane is produced in the United States as an intermediate in the preparation of various polymeric materials including polyurethane plastics and foams and polyester resins A large fraction of the 1 2 epoxypropane is made from propene by way of its chlorohydrm... 

Use Learning By Modeling to compare the C—O bond distances in 1 2 epoxypropane and Its protonated form... 

How do the bond distances of 1 2 epoxypropane change on protonation of the nng oxygen" Assum ing that the longer C—O bond is the weaker of the two do the bond distances in the protonated form correlate with the regioselectivity of acid catalyzed ring opening ... 

Reaction of phenol with 1 2 epoxypropane in aqueous sodium hydroxide at 150°C gives a single product C9H12O2 m 90% yield Suggest a rea sonable structure for this compound... 

Propylene oxide [75-56-9] (methyloxirane, 1,2-epoxypropane) is a significant organic chemical used primarily as a reaction intermediate for production of polyether polyols, propylene glycol, alkanolamines (qv), glycol ethers, and many other useful products (see Glycols). Propylene oxide was first prepared in 1861 by Oser and first polymerized by Levene and Walti in 1927 (1). Propylene oxide is manufactured by two basic processes the traditional chlorohydrin process (see Chlorohydrins) and the hydroperoxide process, where either / fZ-butanol (see Butyl alcohols) or styrene (qv) is a co-product. Research continues in an effort to develop a direct oxidation process to be used commercially. 

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

Epoxypropane, see Propylene oxide 2.3- Epoxy-l-propanol, see Glycidol ... 

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

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