Sodium dodecylbenzenesulfonate

Sodium dodecylbenzenesulfonate
Identifiers
CAS number [http://www.commonchemistry.org/ChemicalDetail.aspx?ref=25155-30-0, [68081-81-2 (mixture mainly C10-C16), 68411-

30-3 (mixture mainly C10-C13) 25155-30-0, [68081-81-2 (mixture mainly C10-C16), 68411- 30-3 (mixture mainly C10-C13)] YesY

Properties
Molecular formula C18H29NaO3S
Molar mass 348.48 g/mol
Solubility in water 20%
 YesY dodecylbenzenesulfonate (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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. It is a major component of laundry detergent.[1]

Contents

Alkylbenzenesulfonates

Most sodium dodecylbenzenesulfonates are a member of the linear alkylbenzenesulfonates, meaning that the dodecyl group (C12H25) is unbranched. This dodecyl chain is attached at the 4-position of the benzenesulfonate group. Linear dodecyl-4-benzenesulfonate anions can exist in six isomers (ignoring optical isomers), depending on the carbon of the dodecyl group that is attached to the benzene ring. The isomer shown to the right is 4-(5-dodecyl)benzenesulfonate (4 indicating the position of the benzene ring, 5 indicating the position on the dodecane chain). Branched isomers, e.g. those derived from tetramerized propylene, are also known (see figure to left) but are not as widely used because they biodegrade too slowly.

A branched dodecylbenzenesulfonate, which has been phased out in developed countries.

Further complicating the description of the commercial materials, sodium dodecylbenzenesulfonate is but one component of a mixture of compounds that feature variable alkyl chain lengths aside from C12, mainly ranging from C10-C16. Dodecylbenzenesulfonate is considered representative of the entire class of compounds, since the mean number of alkyl carbon atoms in the alkylbenzenesulfonates is 12.

Production

Billions of kilograms are produced annually. Given the large scale of the application, the alkylbenzenesulfonates have been prepared by many methods.[2] In the most common route, benzene is alkylated by long chain monoalkenes (e.g. dodecene) using hydrogen fluoride as a catalyst. The purified dodecylbenzenes (and related derivatives) are then sulfonated with sulfur trioxide to give the sulfonic acid. The sulfonic acid is subsequently neutralized with sodium hydroxide.[1]

Environmental considerations

The salt has an LD50 of 2.3 mg/liter for fish, about 4x more toxic than the branched tetrapropylenebenzenesulfonate. It is however biodegraded more rapidly. Oxidative degradation initiates at the alkyl chain.[1]

References

  1. ^ a b c Kurt Kosswig,"Surfactants" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2005, Weinheim. doi:10.1002/14356007.a25_747
  2. ^ "5th World Conference on Detergents" Arno Cahn, ed., 2003. ISBN 1-893997-40-5.

Wikimedia Foundation. 2010.

Look at other dictionaries:

  • Detergent — For the band, see The Detergents. Detergents A detergent is a surfactant or a mixture of surfactants with cleaning properties in dilute solutions. [1] In common usage, detergent refers to alkylbenzenesulfonates, a family of compounds that are… …   Wikipedia

  • Dodecylbenzene — IUPAC name Dodecylbenzene …   Wikipedia

  • Сульфонол — Сульфонол …   Википедия

  • Sulfonic acid — General structure of sulfonic acid. R can also be equal to H. Sulfonic acid (or sulphonic acid) usually refers to a member of the class of organosulfur compounds with the general formula RS(=O)2–OH, where R is an alkyl or aryl.[1] The formal part …   Wikipedia

  • Natriumdodecylbenzolsulfonat — Strukturformel Allgemeines Name Natriumdodecylbenzylsulfonat, (Isomerengemisch) …   Deutsch Wikipedia


Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”

We are using cookies for the best presentation of our site. Continuing to use this site, you agree with this.