Cyclohexene oxide is a cycloaliphatic epoxide. It can react in

cationic polymerization In chemistry, cationic polymerization is a type of chain growth polymerization in which a cationic initiator transfers charge to a monomer which then becomes reactive. This reactive monomer goes on to react similarly with other monomers to form a p ...

to poly(cyclohexene oxide). As

cyclohexene Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkene is a colorless liquid with a sharp smell. It is an intermediate in various industrial processes. Cyclohexene is not very stable upon long term storage with exposure to light an ...

is monovalent, poly(cyclohexene oxide) is a

thermoplastic A thermoplastic, or thermosoft plastic, is any plastic polymer material that becomes pliable or moldable at a certain elevated temperature and solidifies upon cooling. Most thermoplastics have a high molecular weight. The polymer chains associate ...

Production

Cyclohexene oxide is produced in

epoxidation In organic chemistry, an epoxide is a cyclic ether () with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale for ...

reaction from cyclohexene. The epoxidation can take place either in a homogeneous reaction by

peracid A peroxy acid (often spelled as one word, peroxyacid, and sometimes called peracid) is an acid which contains an acidic –OOH group. The two main classes are those derived from conventional mineral acids, especially sulfuric acid, and the peroxy ...

s or heterogeneous catalysis (e.g. silver and molecular

oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as wel ...

). :

250px 5 (five) is a number, numeral and digit. It is the natural number, and cardinal number, following 4 and preceding 6, and is a prime number. It has attained significance throughout history in part because typical humans have five digits on eac ...

In industrial production the heterogeneously catalyzed synthesis is preferred because of better

atom economy Atom economy (atom efficiency/percentage) is the conversion efficiency of a chemical process in terms of all atoms involved and the desired products produced. The simplest definition was introduced by Barry Trost in 1991 and is equal to the ratio ...

, a simpler separation of the product and easier recycling of catalyst. A short overview and an investigation of the oxidation of cyclohexene by

hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3%� ...

is given in the literature. In recent times the catalytic oxidation of cyclohexene by (immobilized) metalloporphyrin complexes has been found to be an efficient way. In laboratory, cyclohexene oxide can also be prepared by reacting

with

magnesium monoperoxyphthalate Magnesium monoperoxyphthalate (MMPP) is a water-soluble peroxy acid used as an oxidant in organic synthesis. Its main areas of use are the conversion of ketones to esters ( Baeyer-Villiger oxidation), epoxidation of alkenes (Prilezhaev reaction), ...

(MMPP) in a mixture of

isopropanol Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable organic compound with a pungent alcoholic odor. As an isopropyl group linked to a hydroxyl group (chemical formula ) it is the simple ...

and

water Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as a ...

as solvent at room temperature. : Synthesis of cyclohexene oxide

With this method, good yields up to 85 % can be reached.

Properties and reactions

Cyclohexene has been studied extensively by analytical methods. Cyclohexene oxide can be polymerized in solution, catalyzed by a solid acid catalyst.

Application

One of the known uses is in the synthesis of

bromadoline Bromadoline (U-47931E) is an opioid analgesic selective for the μ-opioid receptor developed by the Upjohn company in the 1970s. The drug has a potency lying between that of codeine and morphine, being slightly stronger than pentazocine. Broma ...

References

{{reflist, 30em Epoxides Cyclic compounds