FORMALDEHYDE SODIUM SULFOXYLATE
FORMALDEHYDE SODIUM SULFOXYLATE
Rongalite = Safolite = Hydroxymethanesulfinic acid monosodium salt dihydrate = Sodium formaldehyde sulfoxylate = SFS
CAS Number: 6035-47-8 / 149-44-0
EC Number: 205-739-4
Rongalite is a chemical compound with the molecular formula Na+HOCH2SO2−.
Formaldehyde Sodium Sulfoxylate has many additional names, including Rongalit, sodium hydroxymethylsulfinate, sodium formaldehyde sulfoxylate, and Bruggolite.
Formaldehyde Sodium Sulfoxylate is listed in the European Cosmetics Directive as sodium oxymethylene sulfoxylate (INCI).
Formaldehyde Sodium Sulfoxylate is water-soluble and generally sold as the dihydrate.
The compound and Formaldehyde Sodium Sulfoxylates derivatives are widely used in the dye industry.
Use os Formaldehyde Sodium Sulfoxylate:
The original use of Formaldehyde Sodium Sulfoxylate 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 Formaldehyde Sodium Sulfoxylates use as water conditioner for aquaria as it rapidly reduces chlorine and chloramine and reacts with ammonia to form the innocuous aminomethylsulfinate ion.
Formaldehyde Sodium Sulfoxylate is also used as an antioxidant in pharmaceutical formulation.
Formaldehyde Sodium Sulfoxylate has been used increasingly in commercial cosmetic hair dye colour removers despite the generation of formaldehyde, a known human carcinogen.
Formaldehyde Sodium Sulfoxylate has a variety of specialized applications in organic synthesis.
Formaldehyde Sodium Sulfoxylate is mainly used as a discharging agent, color-discharging agent, reductant in printing and dyeing industry, as an activating agent for production styrene-butadise rubber and synthetic resin, also be used to decolourize and bleach some organic matters, for example: as a bleaching agent in synthetic rubber, sugar-making, and food industries.
Formaldehyde Sodium Sulfoxylate may be substituted for the sodium hydrosulfite in some special conditions.
Sodium formaldehyde sulfoxylate main application is as industrial bleaching agent for textiles, molasses, and soaps and helps to de chlorinate water to use as a water conditioner also as an antioxidant.
Sodium Formaldehyde Sulfoxylate also called SFS is a white powder or granules with slight specific odor.
Formaldehyde Sodium Sulfoxylate contains Sodium Hydroxymethane Sulfinate as active ingredient and is used as reducing agent in initiator systems for the main or post polymerization of emulsion polymers.
Rongalite, also called Rongalit (registered trademark of BASF), is sodium hydroxymethylsulfinate, or Na+HOCH2SO2-.
Formaldehyde Sodium Sulfoxylate has many names, including also sodium formaldehyde sulfoxylate, and Bruggolite.
Formaldehyde Sodium Sulfoxylate is listed in the European Cosmetics Directive as sodium oxymethylene sulfoxylate (INCI).
Formaldehyde Sodium Sulfoxylate is water-soluble and generally sold as the dihydrate.
Soluble in water.
Provides a unique versatility of printing on both cotton and synthetics due to the exceptional stability over long periods and high compatibility with various print systems.
Excellent production due to strong reduction power.
Excellent definition of Discharge prints.
Synthesis and reactions
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 Rongalite, which is far less O2-sensitive and thus easier to handle.
The hydroxymethanesulfinate 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 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 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.
Sodium formaldehydesulfoxylate (SFS) is a long name for a rather small molecule.
Formaldehyde Sodium Sulfoxylate also goes by the name sodium hydroxymethanesulfinate or, most commonly, its trade name Rongalite.
Formaldehyde Sodium Sulfoxylate is usually marketed as the dihydrate.
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
Rongalite, also called Rongalit (registered trademark of BASF), is sodium hydroxymethylsulfinate, or Na+HOCH2SO2-.
Formaldehyde Sodium Sulfoxylate has many names, including also sodium formaldehyde sulfoxylate, and Bruggolite.
Formaldehyde Sodium Sulfoxylate is listed in the European Cosmetics Directive as sodium oxymethylene sulfoxylate (INCI).
Formaldehyde Sodium Sulfoxylate is water-soluble and generally sold as the dihydrate.
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.
Formaldehyde Sodium Sulfoxylate is listed in the European Cosmetics Directive as sodium oxymethylene sulfoxylate (INCI).
Formaldehyde Sodium Sulfoxylate is water-soluble and generally sold as the dihydrate.
The compound and its derivatives are widely used in the dye industry.
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.
Systematic Name:
Methanesulfinic acid, 1-hydroxy-, sodium salt (1:1)
CAS Number:
149-44-0
EPA Registry Name:
Sodium sulfoxylate formaldehyde (anhydrous)
Molecular Weight:
119.1
Molecular Formula:
CH4O3S.Na
Density 1.8 g/cm3 (20 °C)
Melting Point: 63 °C
pH value: 9.5 – 10.5 (100 g/l, H₂O, 20 °C)
Vapor pressure: 2.68 hPa (20 °C)
Bulk density: 950 kg/m3
Solubility: 600 g/l
Sodium formaldehyde-sulfoxylate
Molecular formula: Na2S2O4 Appearance: white free-flow crystal powders Packing: 15kg, 25kg, 50kg or 100kg net in iron drums with double inner polybags.
Formaldehyde Sodium Sulfoxylate Widely used in textile industry for vat dyeing, reduction cleaning, printing and stripping, textile textile bleaching.
Formaldehyde Sodium Sulfoxylate is also used in bleaching paper pulps, especially mechanical pulps, it`s the most fitable bleaching agent in pulps.
Formaldehyde Sodium Sulfoxylate is used in bleaching kaolin clay, fur bleaching and reductive whitening, bleaching of bamboo products and straw products.
Formaldehyde Sodium Sulfoxylate is used in mineral, the compound of thiourea and other sulphides.
Formaldehyde Sodium Sulfoxylate is used as reducing agent in chemical industry.
Sodium hydrosulfite food additive grade is used in foodstuffs, as bleaching agent and preservative in dried fruits, dried vegetable, vermicelli, glucose, sugar, rock sugar, caramel, candy, liquid glucose, bamboo shoots, mushrooms and canned mushrooms.
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 to synthesize anilinomethanesulfonates.
Chemical Properties:
white crystalline powder
Chemical Properties:
When freshly prepared, sodium formaldehyde sulfoxylate occurs as white, odorless crystals, which quickly develop a characteristic garlic odor on standing.
Uses:
Pharmaceutic aid (preservative).
Production Methods:
Sodium formaldehyde sulfoxylate is manufactured from sodium dithionate and formaldehyde in water.
Pharmaceutical Applications:
Sodium formaldehyde sulfoxylate is a water-soluble antioxidant and is generally used as the dihydrate.
Formaldehyde Sodium Sulfoxylate 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.
Sodium formaldehyde sulphoxylate is shown to be an inexpensive, efficient reagent for the dehalogenation of phenacyl halides and other α-haloketones.
Some possible mechanisms for the reduction are discussed.
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
Sodium formaldehyde sulfoxylate is a white solid chemical, soluble in water.
Sodium formaldehyde sulfoxylate is generally used as an industrial bleaching agent for textiles, molasses, and soaps.
Formaldehyde Sodium Sulfoxylate also has a niche use as a water conditioner, reducing the amount of chlorine, and in pharmaceuticals as an antioxidant.
storage:
Store in well-closed, light-resistant containers at controlled room temperature (15–30℃).
Incompatibilities:
Sodium formaldehyde sulfoxylate is incompatible with strong oxidizing agents; it is decomposed by dilute acid.
Melting point:64-68 °C(lit.)
Density 1.8 g/cm3 (20℃)
vapor pressure 2.68 hPa (20 °C)
storage temp. Store below +30°C.
solubility alcohol: slightly soluble(lit.)
PH9.5-10.5 (100g/l, H2O, 20℃)
Appearance:white solid (est)
Assay:95.00 to 100.00
Food Chemicals Codex Listed:No
Melting Point:63.00 °C. @ 760.00 mm Hg (est)
Flash Point:32.00 °F. TCC ( 0.00 °C. )
Molecular Formula CH7NaO5S
Molar Mass 154.118 g/mol
Melting Point 63-64℃
Boling Point 446.4°C at 760 mmHg
Flash Point 223.8°C
Vapor Presure 7.6E-10mmHg at 25°C
In the early 20th century, sodium formaldehyde sulfoxylate was identified as an antidote for acute mercury poisoning (e.g. a one time ingestion of a bunch of corrosive mercuric chloride).
An intense treatment regimen from 1942 called for immediately swallowing a bunch of it, injecting it into a vein, irrigating the colon with it twice daily, swallowing and injecting a bunch more of it twice a day for two days, and rising the mouth out with it.
Even with this effort, the antidote was eventually determined to only be effective if administered immediately (i.e. within minutes) after mercury exposure, which isn’t at all practical in most poisoning cases.
Presumably Formaldehyde Sodium Sulfoxylate worked by adding electrons to mercury cations in the stomach and intestines, reducing them to the less harmful elemental form of the metal.
In the 1930s, sodium formaldehyde sulfoxylate was demonstrated to be capable of curing mice intentionally infected with disease-causing bacteria.
Formaldehyde Sodium Sulfoxylate’s unstable in water or aqueous solutions (like, say, body fluids), decomposing to produce formaldehyde and a bunch of sulfur compounds (sodium sulfite, sodium sulfide, sulfur dioxide, and hydrogen sulfide).
Formaldehyde is really good at killing things, so at first glance it appears to be responsible for the curative effect.
However, sodium formaldehyde sulfoxylate only ended up working against one of the thirty two types of bacteria tested, so there was probably something else going on.
Sodium formaldehyde sulfoxylate has also seen use as a photographic developer and as a relatively environmentally friendly reagent for adding sulfur+oxygen groups to various organic molecules and doing other useful chemical synthesis stuff.
Use: In vat color printing pastes: Borstelmann, Fordemwalt, US 2597281 (1952 to Am. Cyanamid). In polymerization of ethylenic compds: GB 816252; GB 852593 (1959 to Hercules Powder; 1960 to Air Reduction). In manuf of arsphenamines: Krumwiede, J. Am. Pharm. Assoc. 8, 795 (1919); Heyl, Miller, ibid. 11, 432 (1922).
Therap-Cat: Treatment of mercury poisoning.
SFS is a concentrated reducing agent used as a redox catalyst in emulsion polymerization of many types of synthetic rubber.
SFS is also widely used in the reductive clearing of disperse dyed synthetic fiber.
Assay (as SO₂, calc. on dried substance): 45.5 – 54.5 %
Appearance: white,finecrystalline powder
Identity (A (metallic mirror)) passes test
Identity (B (color reaction)) passes test
Appearance of solution (50 g/l; water) clear and colorless
Alkalinity (20 g/l, water): passes test
pH (20 g/l, water): 9.5 – 10.5
Iron (Fe): ≤ 25 ppm
Fe (Iron) (ICP) ≤ 25 ppm
Hg (Mercury)*: ≤ 0.3 ppm
Pd (Palladium)* ≤ 1 ppm
Zn (Zinc)*: ≤ 10 ppm
Sodium sulfite (Na₂SO₃) (calculated on dried substance) ≤ 5.0 %
Sulfide (S): passes test
Residual solvents (ICH (Q3C)): excluded by manufacturing process
Loss on drying (105 °C; 3 h):≤ 27.0 %
Sodium Formaldehyde Sulfoxylate contains an amount of CH3NaO3Sequivalent to not less than 45.5percent and not more than 54.5 percent of SO2,calculated on the dried basis.
Formaldehyde Sodium Sulfoxylate may contain a suitable stabilizer,such as sodium carbonate.
Packaging and storage— Preserve in well-closed,light-resistant containers,and store at controlled room temperature.
Clarity and color of solution— Dissolve 1g in 20mLof water,and transfer 10mLto a 20-×150-mm test tube.Compare with water in a similar test tube:the liquids are equally clear and,when viewed transversely by transmitted light,exhibit no apparent difference in color.
Rongalite (Sodium Formaldehyde Sulfoxylate) preparation
Is anyone familar with Formaldehyde Sodium Sulfoxylate? Apparently Formaldehyde Sodium Sulfoxylate is made by reacting formaldehyde with sodium dithionite:
Na2S2O4 + 2 CH2O + H2O –> NaHOCH2SO3 + NaHOCH2SO2
Apparently, the reaction quantitative , so this a way of titrating dithionite (wikipedia).
Apparently Formaldehyde Sodium Sulfoxylate decomposes at 80°C, emmiting H2S, formates, sulfites and methanol
Sodium formaldehyde sulfoxylate
Hydroxymethanesulfinic acid monosodium salt dihydrate
NCGC00166400-01
DSSTox_CID_28956
DSSTox_RID_83221
DSSTox_GSID_49030
CHEMBL3188745
DTXSID4049030
sodium;sulfinomethanolate;dihydrate
Tox21_113558
CAS-6035-47-8
Sodium formaldehydesulfoxylate
Sodium sulfoxylate formaldehyde (anhydrous)[USAN]
Bleachit D
Discolite
Formaldehyde sodium bisulfite adduct
Formaldehyde sodium sulfoxylate
Formaldehydesulfoxylic acid sodium salt
Formapon; Formopan; Hydrolit
Hydrosulfite AWC
Hydroxymethanesulfinic acid sodium salt
Hydroxymethansulfinsaeure, natriumsalz
Leptacid
Leptacit
Natrium formaldehydesulfoxylat
Natrium hydroxymethansulfinat
Oxymethansulfinsaeuren natrium
Redol C
Rodite
Rongalit
Rongalit C
Rongalite; Rongalite C
Sodium (hydroxymethyl)sulfinate
Sodium formaldehyde sulfoxylate
Sodium formaldehydesulfoxylate
Sodium hydroxymethanesulfinate
Sodium methanalsulfoxylate
Sodium formaldehyde sulfoxylate, a small sulfur-containing molecule with a propensity to give away its electrons (i.e. a strong reducing agent), has many names and many uses. One of its aliases, rongalite, comes from “rongeage”, a French word meaning discharge.
Formaldehyde Sodium Sulfoxylate refers to the industrial use of the molecule as a bleaching agent to remove colour from textiles (e.g. to create a white design on a dyed background) and other materials (e.g. to clear up discoloured sugar juice squeezed from plants).
Due to Formaldehyde Sodium Sulfoxylates bleaching ability, sodium formaldehyde sulfoxylate is also found in commercial products for removing or correcting hair dye colour.
Monograph Number: 0008620
Title: Sodium Formaldehydesulfoxylate
CAS Registry Number: 149-44-0
CAS Name: Hydroxymethanesulfinic acid sodium salt
Additional Names: formaldehyde sodium sulfoxylate; formaldehydesulfoxylic acid sodium salt; sodium hydroxymethanesulfinate; sodium methanalsulfoxylate
Trademarks: Aldanil; Rongalite; Rongalite C
Molecular Formula: CH3NaO3S
Molecular Weight: 118.09
Percent Composition: C 10.17%, H 2.56%, Na 19.47%, O 40.65%, S 27.15%
Line Formula: Na[HOCH2SO2]
The first chemical contrast of thiols and sulfides with alcohols and ethers is acidity which is important in organic reactions.
Thiols are stronger acids than relevant alcohols and phenols.
Thiolate conjugate bases are easily formed, and are excellent nucleophiles in SN2 reactions of alkyl halides and tosylates.
The nucleophilicity of sulfur is much greater than that of oxygen, resulting in a number of useful electrophilic substitution reaction that are rare by oxygen.
For example, sulfides form (with alkyl halides) ternary sulfonium salts, in the same alkylattion of tert-amines quaternary ammonium salts, whereas ternary oxonium salts are prepared only under extream conditions.
Without exception, sulfoxides, sulfinate salts and sulfite anion also alkylate on sulfur, despite of the partial negative formal charge on oxygen and partial positive charge on sulfur.
The second character is the oxidation states of sulfur.
Oxygen has only two oxidation states, whereas sulfur covers from –2 to +6 as follows:
-2: Hydrogen Sulfide (H2S), sulfides, sulfonium ions
-1: disulfides
0: S elemental, sulfoxides, sulfenic acids
+2: sulfones, sulfinic acids
+4: sulfonic acids, sulfite esters
+6: sulfate esters
One more sulfur compound’s contrast with oxygen analog is in oxidation chemistry.
Oxidation of sulfur compounds changes the oxidation state of sulfur rather than carbon, whereas, oxidation of alcohols to aldehydes and ketones changes the oxidation state of carbon not oxygen.
Thiols is oxidized to S-S single bond (disufide) which is stronger than O–O bond in peroxide.
Disufide forms sulfenyl chlorides (with chlorine in mild condition) or sulfonic acids under harder condition.
Oxidation of sulfides with hydrogen peroxide (or peracids) yields sulfoxides and then to sulfones.
A certain sulfoxide compound such as dimethyl sulfoxide can be used as an effective oxygen source in the oxidation reaction of primary and secondary alcohols to aldehydes and ketones.
DMSO easily is reduced to dimethyl sulfide and water is taken up by the electrophile. oxidation procedure is very mild and tolerates a variety of other functional groups, including those having oxidizable nitrogen and sulfur atoms.
Sulfinic acid is an organic compound containing -SO2H group which is bonded to a carbon atom.
Hydroxy methanesulfinic acid is used as a strong discharge medium of dyes and pigments.
Formaldehyde Sodium Sulfoxylate is a strong reduction agent for textile printing.
Formaldehyde Sodium Sulfoxylate is used in emulsion polymerisation process.
Textile:
Formaldehyde Sodium Sulfoxylate Used as a discharge printing agent on cotton and synthetic fibers
Formaldehyde Sodium Sulfoxylate Used as a discharge printing agent on cotton and synthetic fibers
Polymer:
Formaldehyde Sodium Sulfoxylate Used as a redox catalyst in emulsion polymerisation process for manufacturing ABS, SBR, X-SBR, NBR, CR, PVC-latices, PVA, EVCL, vinyl acrylate, and styrene acetate.
Pharmaceuticals:
Formaldehyde Sodium Sulfoxylate Used as a stabilizer / antioxidant in a wide range of drug formulations
A mixture of sodium formaldehyde sulfoxylate (I), Fe3+ and a hydroperoxide is an excellent system for initiation of free radical polymerization of vinyl monomers at low temperatures, such as the polymerization of vinyl chloride at -15 °C.
However, the kinetics and mechanism of the reaction in this system have not been studied in detail.
CAS Number:
149-44-0
6035-47-8 (dihydrate)
ChEMBL: ChEMBL2107242 ☒
ChemSpider: 8649
EC Number: 205-739-4
PubChem CID: 23689980
RTECS number: PB0380000
UNII:
X4ZGP7K714
SQ4705447D (dihydrate)
CompTox Dashboard (EPA): DTXSID7027120
CAS Number:
149-44-0
6035-47-8 (dihydrate)
ChEMBL: ChEMBL2107242 ☒
ChemSpider: 8649
EC Number: 205-739-4
PubChem CID: 23689980
RTECS number: PB0380000
UNII:
X4ZGP7K714
SQ4705447D (dihydrate)
CompTox Dashboard (EPA): DTXSID7027120