Olefin

olefin, also called alkene, compound made up of hydrogen and carbon that contains one or more pairs of carbon atoms linked by a double bond. Olefins are examples of unsaturated hydrocarbons (compounds that contain only hydrogen and carbon and at least one double or triple bond). They are classified in either or both of the following ways: (1) as cyclic or acyclic (aliphatic) olefins, in which the double bond is located between carbon atoms forming part of a cyclic (closed-ring) or of an open-chain grouping, respectively, and (2) as monoolefins, diolefins, triolefins, etc., in which the number of double bonds per molecule is, respectively, one, two, three, or some other number.

Acyclic monoolefins have the general formula C_nH_2n, C being a carbon atom, H a hydrogen atom, and n an integer. They are rare in nature but can be formed in large quantities through industrial processing. One of the first processes used to produce them, developed in the early 20th century, was thermal cracking (breaking down of large molecules) of petroleum oils to gasoline. Olefins later were also produced via fluid catalytic cracking, steam cracking, and hydrocracking.

Beginning in the 1970s, so-called linear alpha olefins (LAOs; distinguished by the double bond occurring on the first, or alpha, carbon atom in the unbranched chain) were produced through polymerization (specifically, oligomerization) and olefin metathesis, which together formed the basis of the Shell higher olefin process (SHOP). In olefin oligomerization, the compounds are grown by combining lower-molecular-weight monoolefins, particularly ethylene, which is the simplest olefin. Olefin metathesis involves the exchange of chemical substituents with subsequent re-formation of double bonds. LAOs produced via oligomerization and olefin metathesis are used as starting materials for plastics (e.g., polyethylene), detergents, adhesives, and other products. Hence, lower monoolefins (other examples of which include propylene and butylene) are the basis for an extensive petrochemicals industry. Both ethylene and propylene, which are used as chemical feedstocks (to fuel large chemical reactions), occur naturally in the environment.

Acyclic diolefins, also known as acyclic dialkenes, or acyclic dienes, with the general formula C_nH_2n-2, contain two double bonds; they undergo reactions similar to the monoolefins. The best-known dienes are butadiene and isoprene, used in the manufacture of synthetic rubber.

Olefins containing two to four carbon atoms per molecule are gaseous at ordinary temperatures and pressure; those containing five or more carbon atoms are usually liquid at ordinary temperatures. Olefins are only slightly soluble in water.