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Epoxide
In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile.
A compound containing the epoxide functional group can be called an epoxy, epoxide, oxirane, and ethoxyline. Simple epoxides are often referred to as oxides. Thus, the epoxide of ethylene (C2H4) is ethylene oxide (C2H4O). Many compounds have trivial names; for instance, ethylene oxide is called "oxirane". Some names emphasize the presence of the epoxide functional group, as in the compound 1,2-epoxyheptane, which can also be called 1,2-heptene oxide.
A polymer formed from epoxide precursors is called an epoxy. However, few if any of the epoxy groups in the resin survive the curing process.
The dominant epoxides industrially are ethylene oxide and propylene oxide, which are produced respectively on the scales of approximately 15 and 3 million tonnes/year.
Aside from ethylene oxide, most epoxides are generated when peroxidized reagents donate a single oxygen atom to an alkene. Safety considerations weigh on these reactions because organic peroxides are prone to spontaneous decomposition or even combustion.
Both t-butyl hydroperoxide and ethylbenzene hydroperoxide can be used as oxygen sources during propylene oxidation (although a catalyst is required as well, and most industrial producers use dehydrochlorination instead).
The ethylene oxide industry generates its product from reaction of ethylene and oxygen. Modified heterogeneous silver catalysts are typically employed. According to a reaction mechanism suggested in 1974 at least one ethylene molecule is totally oxidized for every six that are converted to ethylene oxide:
![{\displaystyle {7\,\mathrm {H} {\vphantom {A}}_{\smash[{t}]{2}}\mathrm {C} {=}\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{2}}{}+{}6\,\mathrm {O} {\vphantom {A}}_{\smash[{t}]{2}}{}\mathrel {\longrightarrow } {}6\,\mathrm {C} {\vphantom {A}}_{\smash[{t}]{2}}\mathrm {H} {\vphantom {A}}_{\smash[{t}]{4}}\mathrm {O} {}+{}2\,\mathrm {CO} {\vphantom {A}}_{\smash[{t}]{2}}{}+{}2\,\mathrm {H} {\vphantom {A}}_{\smash[{t}]{2}}\mathrm {O} }}](https://wikimedia.org/api/rest_v1/media/math/render/svg/e02023bbe610060e15acf92840575950f8cd1c5d)
Only ethylene produces an epoxide during incomplete combustion. Other alkenes fail to react usefully, even propylene, though TS-1 supported Au catalysts can selectively epoxidize propylene.
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Epoxide
In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile.
A compound containing the epoxide functional group can be called an epoxy, epoxide, oxirane, and ethoxyline. Simple epoxides are often referred to as oxides. Thus, the epoxide of ethylene (C2H4) is ethylene oxide (C2H4O). Many compounds have trivial names; for instance, ethylene oxide is called "oxirane". Some names emphasize the presence of the epoxide functional group, as in the compound 1,2-epoxyheptane, which can also be called 1,2-heptene oxide.
A polymer formed from epoxide precursors is called an epoxy. However, few if any of the epoxy groups in the resin survive the curing process.
The dominant epoxides industrially are ethylene oxide and propylene oxide, which are produced respectively on the scales of approximately 15 and 3 million tonnes/year.
Aside from ethylene oxide, most epoxides are generated when peroxidized reagents donate a single oxygen atom to an alkene. Safety considerations weigh on these reactions because organic peroxides are prone to spontaneous decomposition or even combustion.
Both t-butyl hydroperoxide and ethylbenzene hydroperoxide can be used as oxygen sources during propylene oxidation (although a catalyst is required as well, and most industrial producers use dehydrochlorination instead).
The ethylene oxide industry generates its product from reaction of ethylene and oxygen. Modified heterogeneous silver catalysts are typically employed. According to a reaction mechanism suggested in 1974 at least one ethylene molecule is totally oxidized for every six that are converted to ethylene oxide:
Only ethylene produces an epoxide during incomplete combustion. Other alkenes fail to react usefully, even propylene, though TS-1 supported Au catalysts can selectively epoxidize propylene.