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{{Chembox {{Chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 401060155
| Watchedfields = changed
⚫ | verifiedrevid = 464402661
| ImageFile = Sodium nonanoyloxybenzenesulfonate.png | ImageFile = Sodium nonanoyloxybenzenesulfonate.png
| ImageSize = 200px | ImageSize = 200px
| IUPACName = Sodium 4-nonanoyloxybenzenesulfonate | PIN = Sodium 4-(nonanoyloxy)benzene-1-sulfonate
| OtherNames = 4-Sulfophenyl nonanoate sodium salt; Sodium ''p''-nonanoyloxybenzenesulfonate; ''p''-(Nonanoyloxy)benzenesulfonic acid sodium salt; ''p''-Sodiosulfophenyl nonanoate | OtherNames = 4-Sulfophenyl nonanoate sodium salt; Sodium ''p''-nonanoyloxybenzenesulfonate; ''p''-(Nonanoyloxy)benzenesulfonic acid sodium salt; ''p''-Sodiosulfophenyl nonanoate
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| Abbreviations = NOBS | Abbreviations = NOBS
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QSKQNALVHFTOQX-UHFFFAOYSA-M | StdInChIKey = QSKQNALVHFTOQX-UHFFFAOYSA-M
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 89740-11-4 | CASNo = 89740-11-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 642JLH7JVI
| PubChem = 174822 | PubChem = 174822
| SMILES = .O=C(Oc1ccccc1S()(=O)=O)CCCCCCCC | SMILES = .O=C(Oc1ccccc1S()(=O)=O)CCCCCCCC
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=15|H=21|Na=1|O=5|S=1 | C=15 | H=21 | Na=1 | O=5 | S=1
| Appearance = | Appearance =
| Density = | Density =
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| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility = }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt = }}
}} }}


'''Sodium nonanoyloxybenzenesulfonate''' ('''NOBS''') is an important component of ]s and ]es. It is known as a ] for ] sources, allowing formulas containing ] releasing chemicals (specifically the ], ], ], ], and ].<ref>{{cite journal | author = Kuzel, P.; Lieser, T. | title = Bleach systems | journal = Tenside, Surfactants, Detergents | year = 1990 | volume = 27 | issue = 1 | pages = 23–8}}</ref> Unlike ], NOBS can be used in a much lower temperature. '''Sodium nonanoyloxybenzenesulfonate''' ('''NOBS''') is an important component of ]s and ]es. It is known as a ] for ] sources, allowing formulas containing ] releasing chemicals (specifically ], ], ], ], and ]) to effect bleaching at lower temperatures.<ref>{{cite journal |author1=Kuzel, P. |author2=Lieser, T. | title = Bleach systems | journal = Tenside, Surfactants, Detergents | year = 1990 | volume = 27 | issue = 1 | pages = 23–8|doi=10.1515/tsd-1990-270109 |s2cid=235325050 }}</ref>

==Synthesis==
NOBS is formed by the reaction of ] (or its ]s) with ] followed by ] using ] to form a ] at the para-position.

==Bleach activation==
NOBS was developed by ] in 1983<ref>{{cite book|last1=Chung|first1=S. Y.|last2=Spadini|first2=G. L.|title=US4412934|date=1983}}</ref> and was first used in American laundry detergents in 1988.<ref name="Cahn1994">{{cite book|author=Arno Cahn|title=Proceedings of the 3rd World Conference on Detergents: Global Perspectives|url=https://books.google.com/books?id=Pbr2HJ1X_DkC&pg=PA64|date=30 January 1994|publisher=The American Oil Chemists Society|isbn=978-0-935315-52-3|pages=64–70}}</ref> NOBS is the main bleach activator used in the U.S.A. and Japan.<ref name=Hirschen>{{cite book|last1=Hirschen|first1=M.|title=Handbook of Detergents Part C: Analysis|date=2005|publisher=Marcel Dekker|isbn=9780824703516|pages=439–470}}</ref> Compared to ], which is the predominant bleach activator used in Europe, NOBS is efficient at much lower temperatures. At 20&nbsp;°C NOBS is 100 times more soluble than TAED in water.<ref name=Reinhardt1>{{cite book|last1=Reinhardt|first1=G.|last2=Borchers|first2=G.|title=Handbook of Detergents, Part E: Applications|date=2009|publisher=CRC Press|isbn=9781574447576}}</ref>
When attacked by the perhydroxyl anion (from hydrogen peroxide), NOBS forms ] (a ]) and releases the leaving group sodium 4-hydroxybenzene sulfonate, which is an inert by-product.


==References== ==References==
{{reflist}} {{reflist}}



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Latest revision as of 19:35, 28 July 2024

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
3D model (JSmol)
Abbreviations NOBS
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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-1Key: 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-1Key: QSKQNALVHFTOQX-REWHXWOFAO
SMILES
  • .O=C(Oc1ccccc1S()(=O)=O)CCCCCCCC
Properties
Chemical formula C15H21NaO5S
Molar mass 336.38 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 perphosphate, sodium persulfate, and urea peroxide) to effect bleaching at lower temperatures.

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 and was first used in American laundry detergents in 1988. NOBS is the main bleach activator used in the U.S.A. and Japan. 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. When attacked by the perhydroxyl anion (from hydrogen peroxide), NOBS forms peroxynonanoic acid (a peroxy acid) and releases the leaving group sodium 4-hydroxybenzene sulfonate, which is an inert by-product.

References

  1. Kuzel, P.; Lieser, T. (1990). "Bleach systems". Tenside, Surfactants, Detergents. 27 (1): 23–8. doi:10.1515/tsd-1990-270109. S2CID 235325050.
  2. Chung, S. Y.; Spadini, G. L. (1983). US4412934.
  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.
  4. Hirschen, M. (2005). Handbook of Detergents Part C: Analysis. Marcel Dekker. pp. 439–470. ISBN 9780824703516.
  5. Reinhardt, G.; Borchers, G. (2009). Handbook of Detergents, Part E: Applications. CRC Press. ISBN 9781574447576.
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