Sodium nonanoyloxybenzenesulfonate

Sodium nonanoyloxybenzenesulfonate
Names
	Preferred IUPAC name Sodium 4-(nonanoyloxy)benzene-1-sulfonate
	Other names 4-Sulfophenyl nonanoate sodium salt; Sodium p-nonanoyloxybenzenesulfonate; p-(Nonanoyloxy)benzenesulfonic acid sodium salt; p-Sodiosulfophenyl nonanoate
Identifiers
CAS Number	89740-11-4 ;
3D model (JSmol)	Interactive image;
Abbreviations	NOBS
ChemSpider	152449 ;
PubChem CID	174822;
UNII	642JLH7JVI ;
CompTox Dashboard (EPA)	DTXSID4029064 ;
	InChI InChI=1S/C15H22O5S.Na/c1-2-3-4-5-6-7-12-15(16)20-13-10-8-9-11-14(13)21(17,18)19;/h8-11H,2-7,12H2,1H3,(H,17,18,19);/q;+1/p-1 Key: QSKQNALVHFTOQX-UHFFFAOYSA-M ; InChI=1/C15H22O5S.Na/c1-2-3-4-5-6-7-12-15(16)20-13-10-8-9-11-14(13)21(17,18)19;/h8-11H,2-7,12H2,1H3,(H,17,18,19);/q;+1/p-1 Key: QSKQNALVHFTOQX-REWHXWOFAO;
	SMILES [Na+].O=C(Oc1ccccc1S([O-])(=O)=O)CCCCCCCC;
Properties
Chemical formula	C15H21NaO5S
Molar mass	336.38 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	(what is ?)
	Infobox references

Sodium nonanoyloxybenzenesulfonate (NOBS) is an important component of laundry detergents and bleaches. It is known as a bleach activator for active oxygen sources, allowing formulas containing hydrogen peroxide releasing chemicals (specifically sodium perborate, sodium percarbonate, , sodium persulfate, and urea peroxide) to effect bleaching at lower temperatures.^[1]

Synthesis[]

NOBS is formed by the reaction of nonanoic acid (or its esters) with phenol followed by aromatic sulfonation using SO₃ to form a sulfonic acid at the para-position.

Bleach activation[]

NOBS was developed by Procter & Gamble in 1983^[2] and was first used in American laundry detergents in 1988.^[3] NOBS is the main bleach activator used in the U.S.A. and Japan.^[4] Compared to TAED, which is the predominant bleach activator used in Europe, NOBS is efficient at much lower temperatures. At 20 °C NOBS is 100 times more soluble than TAED in water.^[5] When attacked by the perhydroxyl anion (from hydrogen peroxide), NOBS forms the peroxy acid peroxynonanoic acid and releases the leaving group sodium 4-hydroxybenzene sulfonate, which is an inert by-product.

References[]

^ Kuzel, P.; Lieser, T. (1990). "Bleach systems". Tenside, Surfactants, Detergents. 27 (1): 23–8.
^ Chung, S. Y.; Spadini, G. L. (1983). US4412934.
^ Arno Cahn (30 January 1994). Proceedings of the 3rd World Conference on Detergents: Global Perspectives. The American Oil Chemists Society. pp. 64–70. ISBN 978-0-935315-52-3.
^ Hirschen, M. (2005). Handbook of Detergents Part C: Analysis. Marcel Dekker. pp. 439–470. ISBN 9780824703516.
^ Reinhardt, G.; Borchers, G. (2009). Handbook of Detergents, Part E: Applications. CRC Press. ISBN 9781574447576.

[1] Kuzel, P.; Lieser, T. (1990). "Bleach systems". Tenside, Surfactants, Detergents. 27 (1): 23–8.

[2] Chung, S. Y.; Spadini, G. L. (1983). US4412934.

[Cahn1994-3] Arno Cahn (30 January 1994). Proceedings of the 3rd World Conference on Detergents: Global Perspectives. The American Oil Chemists Society. pp. 64–70. ISBN 978-0-935315-52-3.

[Hirschen-4] Hirschen, M. (2005). Handbook of Detergents Part C: Analysis. Marcel Dekker. pp. 439–470. ISBN 9780824703516.

[Reinhardt1-5] Reinhardt, G.; Borchers, G. (2009). Handbook of Detergents, Part E: Applications. CRC Press. ISBN 9781574447576.

[1]

[2]

[3]

[4]

[5]