Sodium nonanoyloxybenzenesulfonate

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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
3D model (
JSmol
)
Abbreviations NOBS
ChemSpider
UNII
  • 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 checkY
    Key: QSKQNALVHFTOQX-UHFFFAOYSA-M checkY
  • 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
  • [Na+].O=C(Oc1ccccc1S([O-])(=O)=O)CCCCCCCC
Properties
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).
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Sodium nonanoyloxybenzenesulfonate (NOBS) is an important component of

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

  1. S2CID 235325050
    .
  2. ^ Chung, S. Y.; Spadini, G. L. (1983). US4412934.
  3. ISBN 978-0-935315-52-3
    .
  4. ISBN 9780824703516
    .
  5. ISBN 9781574447576
    .
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