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Sodium Formaldehyde Sulfoxylate is a chemical compound with the molecular formula Na+HOCH2SO2−.
Sodium Formaldehyde Sulfoxylate has many additional names, including Rongalit, sodium hydroxymethylsulfinate, sodium formaldehyde sulfoxylate, and Bruggolite.
CAS Number: 149-44-0
EC Number : 205-739-4
IUPAC Name: Sodium hydroxymethanesulfinate
Chemical Formula: CH3NaO3S
Other names: Aldanil, Discolite, Formopan, Hydrolit, Leptacid, Leptacit, Rodite, Bleachit D, Rongalit C, Rongalite C, Superlite C, Hydrosulfite AWC, Redol C, Sodium methanalsulfoxylate, Natrium hydroxymethansulfinat, Natrium formaldehydesulfoxylat, Oxymethansulfinsaeuren natrium, Formaldehyde sodium sulfoxylate, Sodium sulfoxylate formaldehyde, Sodium (hydroxymethyl)sulfinate, SODIUM FORMALDEHYDESULFOXYLATE, Hydroxymethansulfinsaeure, natriumsalz, Formaldehydesulfoxylic acid sodium salt, 149-44-0, Hydroxymethanesulfinic acid sodium salt, Rongalit, Rongalite, SCHEMBL30017140
Sodium hydroxymethylsulfinate is listed in the European Cosmetics Directive as sodium oxymethylene sulfoxylate (INCI).
Sodium hydroxymethylsulfinate is water-soluble and generally sold as the dihydrate.
Sodium hydroxymethylsulfinate compound and its derivatives are widely used in the dye industry.
Although available commercially, the salt can be prepared from sodium dithionite and formaldehyde:
Na2S2O4 + 2 CH2O + H2O → HO-CH2-SO3Na + HO-CH2-SO2Na
This reaction proceeds quantitatively, such that dithionite can be determined by its conversion to Sodium Formaldehyde Sulfoxylate, which is far less O2-sensitive and thus easier to handle.
The Sodium Formaldehyde Sulfoxylate ion is unstable in solution towards decomposition to formaldehyde and sulfite.
Addition of at least one equivalent of formaldehyde pushes the equilibrium towards the side of the adduct and reacts further to give the bis-(hydroxymethyl)sulfone.
Such solutions are shelf-stable indefinitely.
Sodium Formaldehyde Sulfoxylate was originally developed in the early 20th century for the textile industry as a shelf-stable source of sulfoxylate ion, where the latter can be generated at will.
Sodium hydroxymethylsulfinate In use, when Sodium Formaldehyde Sulfoxylate is made acidic, the reducing sulfoxylate ion and formaldehyde are released in equimolar amounts.
For safety reasons the generation of formaldehyde must be taken into consideration when used industrially.
Sodium Formaldehyde Sulfoxylate can essentially be considered to be a source of SO22−.
As such it is used both as a reducing agent and as a reagent to introduce SO2 groups into organic molecules.
Treatment of elemental Se and Te with NaHOCH2SO2 gives solutions containing the corresponding Na2Sex and Na2Tex, where x is approximately 2.
As a nucleophile, NaHOCH2SO2 reacts with alkylating agents to give sulfones.
HO-CH2-SO2Na + 2 C6H5CH2Br → [C6H5CH2]2SO2 + NaBr + CH2O + HBr
Occasionally, alkylation will occur also at oxygen, thus α,α'-dibromoxylene gives both the sulfone and the isomeric sulfinate ester.
Use
The original use of the compound was as industrial bleaching agent and as a reducing agent for vat dyeing.
Another large-scale use is as a reducing agent in redox-initiator systems for emulsion polymerization.
One of the typical redox pair examples is t-butyl peroxide.
A niche use is its use as water conditioner for aquaria as it rapidly reduces chlorine and chloramine and reacts with ammonia to form the innocuous aminomethylsulfinate ion.
Sodium hydroxymethylsulfinate is also used as an antioxidant in pharmaceutical formulation.
The compound has been used increasingly in commercial cosmetic hair dye colour removers despite the generation of formaldehyde, a known human carcinogen.
Sodium hydroxymethylsulfinate has a variety of specialized applications in organic synthesis.
Related compounds
Sodium hydroxymethylsulfinate zinc complex Zn(HOCH2SO2)2 is marketed under the trademarks Decroline, Decolin, and Safolin. This compound is an additive in polymers and textiles.[5]
Sodium Formaldehyde Sulfoxylate is called Sodium Formaldehyde Sulfoxylate C. Calcium Sodium Formaldehyde Sulfoxylate is called Sodium Formaldehyde Sulfoxylate H.
Sodium Formaldehyde Sulfoxylate, also called Rongalit (registered trademark of BASF), is sodium hydroxymethylsulfinate, or Na+HOCH2SO2-.
The salt has many names, including also sodium formaldehyde sulfoxylate, and Bruggolite.
Sodium hydroxymethylsulfinate is listed in the European Cosmetics Directive as sodium oxymethylene sulfoxylate (INCI).
Sodium hydroxymethylsulfinate is water-soluble and generally sold as the dihydrate.
Sodium formaldehydesulfoxylate (SFS) is a long name for a rather small molecule.
Sodium hydroxymethylsulfinate also goes by the name Sodium Formaldehyde Sulfoxylate or, most commonly, its trade name Sodium Formaldehyde Sulfoxylate.
Sodium hydroxymethylsulfinate is usually marketed as the dihydrate.
SFS has a long history:
Sodium hydroxymethylsulfinate In a short 1908 US patent assigned to Heyden Chemical Works (New York), Bruno R. Seifert and Otto W. Meves reduced formaldehyde and sulfur dioxide with zinc dust to a paste containing a zinc formaldehydesulfoxylate that could be converted to the sodium salt with sodium hydroxide or carbonate.
In a 1922 article, Frederick W. Heyl and Frank E. Greer of Upjohn1 (Kalamazoo, MI) reported an improved synthesis of a method described in a 1913 German patent.
Sodium hydroxymethylsulfinate mixture of formaldehyde and sodium hydrogen sulfite is treated with a mixture of zinc dust and zinc oxide.
Sodium hydroxymethylsulfinate convoluted purification process leads to acceptably pure SFS.
A 1935 patent by Frederick W. Binns at the Virginia Smelting Co.2 (Portland, ME) describes a similar synthesis that starts from zinc, sulfur dioxide, and formaldehyde.
Today SFS is manufactured from sodium dithionite (Na2S2O4) and formaldehyde.
Sodium hydroxymethylsulfinate was originally developed as a treatment for mercury poisoning (hence its pharmaceutical origin), but that was of limited value.
Sodium hydroxymethylsulfinate current uses are in vat dyeing as a reducing agent, in redox polymerization initiator systems, and for aquarium water conditioning.
Earlier this month, Scientific Update, a Mayfield, UK–based firm that holds conferences and training courses for industrial chemists and chemical engineers, featured Sodium Formaldehyde Sulfoxylate as its Reagent of the Month. The article focuses on the uses of the reagent in organic chemical synthesis.
Use: Sodium formaldehyde sulfoxylate is generally used as an industrial bleaching agent for textiles, molasses, and soaps.
Sodium hydroxymethylsulfinate also has a niche use as a water conditioner, reducing the amount of chlorine, and in pharmaceuticals as an antioxidant.
