Cyclohexene
Encyclopedia
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 and air because it forms peroxides
.
of benzene
, a process developed by Asahi Chemical Company. It is converted to cyclohexanol
, which is dehydrogenated
to give cyclohexanone
, a precursor to caprolactam
. Cyclohexene is also a precursor to adipic acid
, maleic acid
, dicyclohexyladipate, and cyclohexeneoxide. Furthermore, it is used as a solvent
.
students is the acid
catalyzed dehydration
of cyclohexanol
with distillative
removal of the resulting cyclohexene from the reaction mixture:
Hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls....
with the formula C6H10. This cycloalkene
Cycloalkene
A cycloalkene or cycloolefin is a type of alkene hydrocarbon which contains a closed ring of carbon atoms, but has no aromatic character. Some cycloalkenes, such as cyclobutene and cyclopentene, can be used as monomers to produce polymer chains. Unless the rings are very large, cycloalkenes are...
is a colorless liquid
Liquid
Liquid is one of the three classical states of matter . Like a gas, a liquid is able to flow and take the shape of a container. Some liquids resist compression, while others can be compressed. Unlike a gas, a liquid does not disperse to fill every space of a container, and maintains a fairly...
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 and air because it forms peroxides
Organic peroxide
Organic peroxides are organic compounds containing the peroxide functional group . If the R' is hydrogen, the compound is called an organic hydroperoxide. Peresters have general structure RCOOR. The O-O bond easily breaks and forms free radicals of the form RO·...
.
Production and uses
Cyclohexene is produced by the partial hydrogenationHydrogenation
Hydrogenation, to treat with hydrogen, also a form of chemical reduction, is a chemical reaction between molecular hydrogen and another compound or element, usually in the presence of a catalyst. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically...
of benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
, a process developed by Asahi Chemical Company. It is converted to cyclohexanol
Cyclohexanol
Cyclohexanol is the organic compound with the formula 5CHOH. The molecule is related to cyclohexane ring by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid, which, when very pure, melts near room temperature...
, which is dehydrogenated
Dehydrogenation
Dehydrogenation is a chemical reaction that involves the elimination of hydrogen . It is the reverse process of hydrogenation. Dehydrogenation reactions may be either large scale industrial processes or smaller scale laboratory procedures....
to give cyclohexanone
Cyclohexanone
Cyclohexanone is the organic compound with the formula 5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oil has an odor reminiscent of peardrop sweets as well as acetone. Over time, samples assume a yellow color due to oxidation...
, a precursor to caprolactam
Caprolactam
Caprolactam is an organic compound with the formula 5CNH. This colourless solid is a lactam or a cyclic amide of caproic acid. Approximately 2 billion kilograms are produced annually...
. Cyclohexene is also a precursor to adipic acid
Adipic acid
Adipic acid is the organic compound with the formula 42. From the industrial perspective, it is the most important dicarboxylic acid: About 2.5 billion kilograms of this white crystalline powder are produced annually, mainly as a precursor for the production of nylon...
, maleic acid
Maleic acid
Maleic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. Maleic acid is the cis-isomer of butenedioic acid, whereas fumaric acid is the trans-isomer...
, dicyclohexyladipate, and cyclohexeneoxide. Furthermore, it is used as a solvent
Solvent
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...
.
Laboratory experiments
A common experiment for beginning organic chemistryOrganic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...
students is the acid
Acid
An acid is a substance which reacts with a base. Commonly, acids can be identified as tasting sour, reacting with metals such as calcium, and bases like sodium carbonate. Aqueous acids have a pH of less than 7, where an acid of lower pH is typically stronger, and turn blue litmus paper red...
catalyzed dehydration
Dehydration reaction
In chemistry and the biological sciences, a dehydration reaction is usually defined as a chemical reaction that involves the loss of water from the reacting molecule. Dehydration reactions are a subset of elimination reactions...
of cyclohexanol
Cyclohexanol
Cyclohexanol is the organic compound with the formula 5CHOH. The molecule is related to cyclohexane ring by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid, which, when very pure, melts near room temperature...
with distillative
Distillation
Distillation is a method of separating mixtures based on differences in volatilities of components in a boiling liquid mixture. Distillation is a unit operation, or a physical separation process, and not a chemical reaction....
removal of the resulting cyclohexene from the reaction mixture:
- Critical temperature: 287.2 °C (560.4 K)
- 1,3-Cyclohexadiene1,3-Cyclohexadiene1,3-Cyclohexadiene is a highly flammable cycloalkene that occurs as a colorless clear liquid. Its refractive index is 1.475 .It can be used as a hydrogen donor in transfer hydrogenation, since its conversion to benzene + hydrogen is in fact exothermic .Despite this apparent instability with respect...
- 1,4-Cyclohexadiene1,4-Cyclohexadiene1,4-Cyclohexadiene is a highly flammable cycloalkene that occurs as a colorless clear liquid.1,4-Cyclohexadiene and related compounds may be prepared from benzene using lithium or sodium in liquid ammonia, this process being known as a Birch reduction. However 1,4-cyclohexadiene is easily oxidised...