Dodecylbenzene
Encyclopedia
Dodecylbenzene is an organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the formula C12H25C6H5. This colourless waxy solid consists of a dodecyl group (C12H25) attached to a phenyl group
Phenyl group
In organic chemistry, the phenyl group or phenyl ring is a cyclic group of atoms with the formula C6H5. Phenyl groups are closely related to benzene. Phenyl groups have six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the...

 (C6H5). Dodecylbenzene is a precursor to sodium dodecylbenzenesulfonate
Sodium dodecylbenzenesulfonate
Sodium dodecylbenzenesulfonate is a series of organic compounds with the formula C12H25C6H4SO3Na. It is a colourless salt with useful properties as a surfactant. It is usually produced as a mixture of related sulfonates...

, a surfactant
Surfactant
Surfactants are compounds that lower the surface tension of a liquid, the interfacial tension between two liquids, or that between a liquid and a solid...

 that is a key ingredient of household laundry detergent
Laundry detergent
Laundry detergent, or washing powder, is a substance that is a type of detergent that is added for cleaning laundry. In common usage, "detergent" refers to mixtures of chemical compounds including alkylbenzenesulfonates, which are similar to soap but are less affected by "hard water." In most...

s, such as Tide
Tide (detergent)
Tide is the brand-name of a popular laundry detergent manufactured by Procter & Gamble and first introduced to the United States consumer in 1946. It is also marketed in Canada, Saudi Arabia, Morocco, India and several other countries...

.

Production

Dodecylbenzene can exist as six isomers (ignoring optical isomers), depending on which carbon of the dodecyl group that is attached to the benzene ring. This compound and some related ones with the formulae C10+nH21+2nC6H5 (n = 0-6) are produced industrially by treating the corresponding alkenes C10+nH20+2n with an excess of benzene in the presence of hydrogen fluoride
Hydrogen fluoride
Hydrogen fluoride is a chemical compound with the formula HF. This colorless gas is the principal industrial source of fluorine, often in the aqueous form as hydrofluoric acid, and thus is the precursor to many important compounds including pharmaceuticals and polymers . HF is widely used in the...

 or related acid catalysts. The resulting alkylbenzene compounds are sulfonated to give the corresponding sulfonic acid
Sulfonic acid
Sulfonic acid usually refers to a member of the class of organosulfur compounds with the general formula RS2–OH, where R is an alkyl or aryl. The formal part of acid, HS2–OH, are formally derivatives of the "parent" inorganic compound with the formula HSO2.-Preparation:Sulfonic acid is...

s. This sulfonation can be highly specific to place the sulfonic acid group across the ring, in the 4-position. The resulting sulfonic acid is then neutralized with base to give sodium dodecylbenzenesulfonate, which is subsequently blended with other components to give various cleaning products.
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