Sodium hydroxymethanesulphinate

Description

Sodium formaldehydesulfoxylate (SFS) is a long name for a rather small molecule. It also goes by the name sodium hydroxymethanesulfinate or, most commonly, its trade name Rongalite. It is usually marketed as the dihydrate.
SFS has a long history:
Today SFS is manufactured from sodium dithionite (Na2S2O4) and formaldehyde. It was originally developed as a treatment for mercury poisoning (hence its pharmaceutical origin), but that was of limited value. Its 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 Rongalite as its Reagent of the Month. The article focuses on the uses of the reagent in organic chemical synthesis.
1. Upjohn is now part of Pfizer. In the May 1949 issue of an Upjohn house publication, Heyl was referred to as “the Father of Upjohn Research”.
2. Later based in West Norfolk, VA. See a 1949 ad in an ACS journal.

Chemical properties

white solid; used as stripping and discharge agent for textiles [HAW93]

Chemical properties

When freshly prepared, sodium formaldehyde sulfoxylate occurs as white, odorless crystals, which quickly develop a characteristic garlic odor on standing.

The Uses of Sodium hydroxymethanesulphinate

Pharmaceutic aid (preservative).

The Uses of Sodium hydroxymethanesulphinate

Sodium Hydroxymethanesulfinate Hydrate is the hydrated version of Sodium Hydroxymethanesulfinate (S634950), which is an organic reductant that is stable in alkaline enviroments but readily decomposes in acidic medium to produce a number of products, one of them being sulfur dioxide. Sodium hydroxymethanesulfinate is also used in conjunction with substituted anilines (e.g. p-Anisidine [A673505]) to synthesize anilinomethanesulfonates.

Production Methods

Sodium formaldehyde sulfoxylate is manufactured from sodium dithionate and formaldehyde in water.

Flammability and Explosibility

Non flammable

Pharmaceutical Applications

Sodium formaldehyde sulfoxylate is a water-soluble antioxidant and is generally used as the dihydrate. It is used in the formulation of injection products at a level of up to 0.1% w/v in the final preparation administered to the patient.

Safety

The toxicological properties of sodium formaldehyde sulfoxylate have not been fully investigated. However, it is used in the formulation of injection products at a level to 0.1% w/v in the final preparation administered to the patient.
Sodium formaldehyde sulfoxylate is moderately toxic by ingestion, and when heated to decomposition it emits toxic fumes of sulfur dioxide and sodium oxide.
LD50 (mouse, oral): 4 g/kg
LD50 (rat, IP): >2 g/kg
LD50 (rat, oral): >2 g/kg

storage

Store in well-closed, light-resistant containers at controlled room temperature (15–30℃).

Purification Methods

It crystallises from H2O as the dihydrate and decomposes at higher temperatures. Store it in a closed container in a cool place. It is insoluble in EtOH and Et2O and is a good reducing agent. [X-ray structure: Tuter J Chem Soc 3064 1955.] Note that this compound {HOCH2SO2Na} should not be confused with formaldehyde sodium bisulfite adduct {HOCH2SO3Na} from which it is prepared by reduction with Zn. [Beilstein 1 IV 3052.]

Incompatibilities

Sodium formaldehyde sulfoxylate is incompatible with strong oxidizing agents; it is decomposed by dilute acid.

Regulatory Status

Included in the FDA Inactive Ingredients Database (parenteral products up to 0.1% via the IM, IV, and SC routes). Included in the Canadian List of Acceptable Non-medicinal Ingredients.