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Sodium Cumenesulfonate
"Descrizione"
by A_Partyns (12876 pt)
2023-Jul-20 12:19

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Sodium Cumenesulfonate is a chemical compound.

The name describes the structure of the molecule:

  • Sodium is the sodium ion (Na+), a metal that readily forms positive ions (cations).
  • Cumene is the common name for isopropylbenzene, an organic compound consisting of a benzene ring replaced by an isopropyl group.
  • sulfonate or sulfonate group (-SO3-) is a sulphur atom bonded to three oxygen atoms and one carbon atom of cumene. The sulphonate group is a strongly acidic group and is often found in detergents and surfactants.

Description of the raw materials used in its production:

Cumenesulfonic Acid - Cumenesulfonic acid is an organic compound derived from cumene (isopropylbenzene). It can be obtained through the sulfonation of cumene using sulfuric acid.

Sodium Hydroxide - Sodium hydroxide (NaOH) is an inorganic compound commonly used in the production of sodium salts. It is used in the neutralization reaction to convert cumenesulfonic acid into sodium cumenesulfonate.

The synthesis process takes place in different steps:

  • Production of cumene. The first step is the production of cumene, a compound obtained from benzene and propylene. This process is alkylation, in which benzene and propylene are mixed in the presence of an acid catalyst.
  • Sulphonation. Cumene is treated with sulphuric acid in a process called sulphonation, which introduces a sulphonic acid group into the cumene molecule, creating cumenesulphonic acid.
  • Neutralisation. Cumenesulphonic acid is neutralised with a base, usually sodium hydroxide (NaOH). This replaces the hydrogen in the sulphonic acid group with a sodium ion, creating sodium coumenesulphonate.

What it is for and where

Cosmetics

Sodium Cumenesulfonate is a surfactant (removes dirt particles) and acts with the following INCI functions:

  • Surfactant - Hydrotrope (solubilizing agents).  It has the property of facilitating the miscibility of other compounds that are poorly soluble in water and does not form micelles in the solubilisation process, even with a chemical reaction of complexation or molecular aggregation. The two fundamental solubilisation factors are the hydrotropic-solute association mediated by the depression of water activity and ionic dissociation.
  • Surfactant - Cleansing agent. Cosmetic products used to cleanse the skin utilise the surface-active action that produces a lowering of the surface tension of the stratum corneum, facilitating the removal of dirt and impurities. 

Studies

Hydrotropes are mild surface active amphiphilic organic salts with hydrophobic part comparatively smaller than in the case of conventional surfactant. Hydrotropes exhibit a higher and often more selective ability to solubilization of organic compounds in water. The self-aggregation of the hydrotropes has been considered to be a pre-requisite for a number of applications in various fields such as drugs solubilization (Yalkowsky 1981), chemical reactions (Khadilkar et al. 1995), and separation of organic compounds (Gaikar and Phatak 1999). Hydrotropes are among over 5,000 high production volume chemical substances listed by the Organization for Economic Cooperation and Development (OECD). The consumption of these substances in 2005 reaches ca. 29,000 metric tons in the USA, 17,000 in Europe, and 1,100 in Australia. These compounds are used as additives for household cleaners such as laundry powders and liquids, laundry bleach, dishwashing liquid, toilet cleaners and liquid, powder, gel, and spray surface cleaners. The use of hydrotropes in household laundry and cleaning products raises no safety concerns for the consumers. They are also used as corrosion inhibitors, components of electroplating baths, and as a support for an extraction process (Stanton et al. 2010). The studies carried out on individual hydrotropes or surfactant-hydrotrope mixtures support the fact that hydrotropes are able to form self-aggregates in aqueous solutions known as minimum hydrotrope concentration (MHC), analogous to critical micelle concentration (CMC) for surfactants (Bhat and Gaikar 1999; Bhat and Gaikar 2000) (1).

Delivery of hydrophobic griseofulvin drug via hydrotrope sodium cumene sulfonate (SCS) cluster (2).

  • Molecular Formula C9H11NaO3S
  • Molecular Weight  222.24 g/mol
  • CAS     32073-22-6    28348-53-0
  • UNII   AZ696V2810
  • EC number   250-913-5  248-983-7

Synonyms :

  • sodium p-cumenesulfonate
  • Sodium 4-isopropylbenzenesulfonate
  • sodium;4-propan-2-ylbenzenesulfonate
  • Sodium cumene sulfonate
  • p-Cumenesulfonic acid sodium salt

References_____________________________________________________________________

(1) Lidia Osiewała,Adam Socha, Aleksandra Perek, Marek Socha, Jacek Rynkowski -  Electrochemical, Photochemical, and Photoelectrochemical Treatment of Sodium p-Cumenesulfonate   Water Air Soil Pollut. 2013; 224(9): 1657. Published online 2013 Aug 13. doi:  10.1007/s11270-013-1657-3

(2) Das S, Paul S. Exploring the binding sites and binding mechanism for hydrotrope encapsulated griseofulvin drug on γ-tubulin protein. PLoS One. 2018 Jan 11;13(1):e0190209. doi: 10.1371/journal.pone.0190209. eCollection 2018.

 

 

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