Rongalite

Rongalite

Names
IUPAC name Sodium hydroxymethanesulfinate
Other names Sodium formaldehydesulfoxylate, sodium oxymethylene sulfoxylate, Brüggolit
Identifiers
CAS Number	149-44-0 Y 6035-47-8 (dihydrate) N
ChemSpider	8649 Y
Jmol 3D model	Interactive image
PubChem	8999
RTECS number	PB0380000
UNII	X4ZGP7K714 Y
InChI InChI=1S/CH4O3S.Na/c2-1-5(3)4;/h2H,1H2,(H,3,4);/q;+1/p-1 Y Key: XWGJFPHUCFXLBL-UHFFFAOYSA-M Y InChI=1/CH4O3S.Na/c2-1-5(3)4;/h2H,1H2,(H,3,4);/q;+1/p-1 Key: XWGJFPHUCFXLBL-REWHXWOFAH
SMILES [Na+].[O-]S(=O)CO
Properties
Chemical formula	CH3NaO3S
Molar mass	118.10 g/mol 154.14 g/mol, dihydrate
Appearance	colorless crystals
Density	1.75 g/cm3, dihydrate
Melting point	64.5 °C (148.1 °F; 337.6 K) dihydrate
Solubility in water	600 g/L, dihydrate (approximate)
Acidity (pKa)	decomposes at low pH
Structure
Molecular shape	pyramidal at S
Vapor pressure	{{{value}}}
Related compounds
Related compounds	SO32−, CH2O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Rongalite, 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. It is listed in the European Cosmetics Directive as sodium oxymethylene sulfoxylate (INCI). It is water-soluble and generally sold as the dihydrate. The compound and its derivatives are widely used in the dye industry.

Synthesis and reactions

This salt is 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 Rongalite, which is far less O₂-sensitive and thus easier to handle.

The hydroxymethanesulfinate ion is unstable in solution towards decomposition to formaldehyde and sulfoxylate ion. 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 hydroxymethanesulfinate 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. In use, when sodium hydroxymethanesulfinate 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.

NaHOCH₂SO₂ 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 Na₂Se_x and Na₂Te_x, 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. It is also used as an antioxidant in pharmaceutical formulation.

The compound has, in recent years, been used increasingly in commercial cosmetic hair dye colour removers despite the generation of formaldehyde, a known human carcinogen.

Related compounds

The zinc complex Zn(HOCH₂SO₂)₂ is marketed under the trademarks Decroline, Decolin, and Safolin. This compound is an additive in polymers and textiles.

Sodium hydroxymethanesulfinate is called Rongalite C. Calcium hydroxymethanesulfinate is called Rongalite H.