Dodecylbenzene

Dodecylbenzene is an organic compound with the formula C
12H
25C
6H
5. Dodecylbenzene is a colorless liquid with a weak oily odor that floats on water.

Dodecylbenzene
Names
Preferred IUPAC name
Dodecylbenzene
Other names
1-Phenyldodecane, Phenyldodecane, n-Dodecylbenzene, Laurylbenzene
Identifiers
3D model (JSmol)
1909107
ChemSpider
ECHA InfoCard 100.004.175
EC Number
  • 204-591-8
RTECS number
  • CZ9540000
UNII
  • InChI=1S/C18H30/c1-2-3-4-5-6-7-8-9-10-12-15-18-16-13-11-14-17-18/h11,13-14,16-17H,2-10,12,15H2,1H3 checkY
    Key: KWKXNDCHNDYVRT-UHFFFAOYSA-N checkY
  • InChI=1/C18H30/c1-2-3-4-5-6-7-8-9-10-12-15-18-16-13-11-14-17-18/h11,13-14,16-17H,2-10,12,15H2,1H3
    Key: KWKXNDCHNDYVRT-UHFFFAOYAI
  • c1ccccc1CCCCCCCCCCCC
Properties
C18H30
Molar mass 246.43 g·mol−1
Appearance colourless liquid
Density 0.856 g·cm−3
Melting point 3 °C (37 °F; 276 K)
Boiling point 328 °C (622 °F; 601 K)
insoluble
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H315, H410, H413
P264, P273, P280, P302+P352, P321, P332+P313, P362, P391, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
1
1
0
Flash point 135 °C (275 °F; 408 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

This colourless waxy solid consists of a dodecyl group (C
12H
25) attached to a phenyl group (C
6H
5). Dodecylbenzene is a precursor to sodium dodecylbenzenesulfonate, a surfactant that is a key ingredient of household laundry detergents, such as detergent powder.[1]

Production

This compound and some related alkylbenzenes are produced industrially by alkylation of benzene with the corresponding alkenes in the presence of hydrogen fluoride or related acid catalysts. The resulting linear alkylbenzene compounds are sulfonated to give the corresponding sulfonic acids. 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 alkylbenzenesulfonate, which is subsequently blended with other components to give various cleaning products.[1]

Dodecylbenzene (and its isomers) are precursors to linear alkylbenzene sulfonate detergents.[2]

References
  1. Kurt Kosswig,"Surfactants" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2005, Weinheim. doi:10.1002/14356007.a25_747
  2. Bipin V. Vora; Joseph A. Kocal; Paul T. Barger; Robert J. Schmidt; James A. Johnson (2003). "Alkylation". Kirk‐Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0112112508011313.a01.pub2. ISBN 0-471-23896-1.
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