Dodecylbenzene

1-Dodecylbenzene

Names
Preferred IUPAC name Dodecylbenzene
Other names 1-Phenyldodecane, Phenyldodecane, n-Dodecylbenzene, Laurylbenzene
Identifiers
CAS Number	29986-57-0 Y 123-01-3 Y
3D model (JSmol)	Interactive image
Abbreviations	PhDo DoPh
Beilstein Reference	1909107
ChemSpider	28977 Y
ECHA InfoCard	100.004.175
EC Number	204-591-8
PubChem CID	31237
RTECS number	CZ9540000
UNII	A2AX003680 Y
CompTox Dashboard (EPA)	DTXSID7026994
InChI 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 Y Key: KWKXNDCHNDYVRT-UHFFFAOYSA-N Y 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
SMILES c1ccccc1CCCCCCCCCCCC
Properties
Chemical formula	C18H30
Molar mass	246.438 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)
Solubility in water	insoluble
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H410, H413
Precautionary statements	P264, P273, P280, P302+P352, P321, P332+P313, P362, P391, P501
NFPA 704 (fire diamond)	1 1 0
Flash point	135 °C (275 °F; 408 K)
Safety data sheet (SDS)	https://www.sigmaaldrich.com/US/en/sds/aldrich/113239
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Dodecylbenzene is an organic compound with the molecular formula C₁₈H₃₀ (structurally C₁₂H₂₅C₆H₅). Dodecylbenzene is a colorless liquid with a weak odor and floats on water.

Dodecylbenzene is a linear alkylbenzene consisting of a dodecyl group (C₁₂H₂₅−) attached to a phenyl group (−C₆H₅). Dodecylbenzene is a precursor to sodium dodecylbenzenesulfonate, a surfactant that is a key ingredient of household laundry detergents, such as detergent powder.

Production

This compound and some related linear alkylbenzenes are produced industrially by alkylation of benzene with the corresponding terminal alkenes in the presence of hydrogen fluoride, aluminium trichloride, or related acids used as the catalyst:

R−CH=CH₂ + C₆H₆ → R−CH₂−CH₂−C₆H₅

The resulting linear alkylbenzene compounds are sulfonated on the benzene ring to give the corresponding sulfonic acids. The sulfonation for dodecylbenzene:

C₁₂H₂₅C₆H₅ + SO₃ → C₁₂H₂₅C₆H₄SO₃H

This sulfonation can be highly specific to place the sulfonic acid group across the ring, in the 4-position (para to the alkyl group). The resulting sulfonic acid is then neutralized with base to give the corresponding linear alkylbenzenesulfonate salt. The dodecylbenzenesulfonic acid reaction with the base sodium hydroxide:

C₁₂H₂₅C₆H₄SO₃H + OH⁻ → C₁₂H₂₅C₆H₄SO₃⁻ + H₂O

Subsequently, the finished product is blended with other components for the manufacturing of cleaning products.

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