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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 402591152 |
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| Watchedfields = changed |
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| Name = Rongalite |
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| verifiedrevid = 464383513 |
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| ImageFile = Rongalite.png |
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| Name = Rongalite |
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| ImageFile = Rongalite.svg |
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| ImageSize = 150px |
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| ImageSize = 150px |
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| ImageName = Rongalite |
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| ImageName = Rongalite |
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| IUPACName = Sodium hydroxymethanesulfinate |
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| IUPACName = Sodium hydroxymethanesulfinate |
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| OtherNames = Rongalite<br />Sodium formaldehydesulfoxylate |
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| OtherNames = Sodium formaldehydesulfoxylate, sodium oxymethylene sulfoxylate, Brüggolit |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| SMILES = .S(=O)CO |
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| SMILES = .S(=O)CO |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8649 |
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| ChemSpiderID = 8649 |
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| PubChem = 8999 |
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| PubChem = 23689980 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = X4ZGP7K714 |
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| UNII = X4ZGP7K714 |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = SQ4705447D |
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| UNII1_Comment = (dihydrate) |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 2107242 |
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| InChI = 1/CH4O3S.Na/c2-1-5(3)4;/h2H,1H2,(H,3,4);/q;+1/p-1 |
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| InChI = 1/CH4O3S.Na/c2-1-5(3)4;/h2H,1H2,(H,3,4);/q;+1/p-1 |
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| InChIKey = XWGJFPHUCFXLBL-REWHXWOFAH |
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| InChIKey = XWGJFPHUCFXLBL-REWHXWOFAH |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 149-44-0 |
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| CASNo = 149-44-0 |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| CASOther = </br>, dihydrate |
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| RTECS = PB0380000 |
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| CASNo2 = 6035-47-8 |
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| CASNo2_Comment = (dihydrate) |
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| RTECS = PB0380000 |
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| EC_number = 205-739-4 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = CH<sub>3</sub>NaO<sub>3</sub>S |
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| Formula = CH<sub>3</sub>NaO<sub>3</sub>S |
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| MolarMass = 118.10 g/mol</br> 154.14 g/mol, dihydrate |
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| MolarMass = 118.10 g/mol<br> 154.14 g/mol, dihydrate |
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| Appearance = colorless crystals |
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| Appearance = colorless crystals |
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| Density = 1.75 g/cm<sup>3</sup>, dihydrate |
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| Density = 1.75 g/cm<sup>3</sup>, dihydrate |
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| Solubility = 600 g/L, dihydrate (approximate) |
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| Solubility = 600 g/L, dihydrate (approximate) |
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| MeltingPt = 64.5 °C, dihydrate |
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| MeltingPtC = 64.5 |
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| MeltingPt_notes = dihydrate |
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| pKa = decomp. at low pH |
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| pKa = decomposes at low pH |
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| Section3 = {{Chembox Structure |
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|Section3={{Chembox Structure |
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| MolShape = pyramidal at S |
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| MolShape = pyramidal at S |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| MainHazards = non-toxic |
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| MainHazards = |
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| GHSPictograms = {{GHS08}} |
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| RSPhrases = ]: 36/37/38 ]:26-36 |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|341}} |
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| PPhrases = {{P-phrases|201|202|281|308+313|405|501}} |
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}} |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| Function = compounds |
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| OtherFunction_label = compounds |
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| OtherFunctn = ], ] |
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| OtherFunction = ], ] |
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'''Rongalite''' is a chemical compound with the molecular formula Na<sup>+</sup>HOCH<sub>2</sub>SO<sub>2</sub><sup>−</sup>. This ] has many additional names, including '''Rongalit''', '''sodium hydroxymethylsulfinate''', '''sodium formaldehyde sulfoxylate''', and '''Bruggolite'''. It is listed in the European Cosmetics Directive as '''sodium oxymethylene sulfoxylate''' (]). It is water-soluble and generally sold as the dihydrate. The compound and its ] are widely used in the dye industry.<ref name=Ull>D. Schubart "Sulfinic Acids and Derivatives" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2012, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a25_461}}</ref> The structure of this salt has been confirmed by ].<ref>{{cite journal |doi=10.1039/JR9620003400|title=671. A Detailed Refinement of the Crystal Structure of Sodium Hydroxymethanesulphinate Dihydrate (Rongalite) |year=1962 |last1=Truter |first1=Mary R. |journal=Journal of the Chemical Society (Resumed) |page=3400 }}</ref> |
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==Synthesis and reactions== |
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Although available commercially, the salt can be prepared from ] and ]: |
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:Na<sub>2</sub>S<sub>2</sub>O<sub>4</sub> + 2 CH<sub>2</sub>O + H<sub>2</sub>O → HO-CH<sub>2</sub>-SO<sub>3</sub>Na + HO-CH<sub>2</sub>-SO<sub>2</sub>Na |
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This reaction proceeds quantitatively, such that dithionite can be determined by its conversion to Rongalite, which is far less O<sub>2</sub>-sensitive and thus easier to handle. |
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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. |
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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. |
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NaHOCH<sub>2</sub>SO<sub>2</sub> can essentially be considered to be a source of SO<sub>2</sub><sup>2−</sup>. As such it is used both as a reducing agent and as a reagent to introduce SO<sub>2</sub> groups into organic molecules. Treatment of elemental Se and Te with NaHOCH<sub>2</sub>SO<sub>2</sub> gives solutions containing the corresponding Na<sub>2</sub>Se<sub>x</sub> and Na<sub>2</sub>Te<sub>x</sub>, where x is approximately 2. As a nucleophile, NaHOCH<sub>2</sub>SO<sub>2</sub> reacts with alkylating agents to give ]s. |
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::HO-CH<sub>2</sub>-SO<sub>2</sub>Na + 2 C<sub>6</sub>H<sub>5</sub>CH<sub>2</sub>Br → <sub>2</sub>SO<sub>2</sub> + NaBr + CH<sub>2</sub>O + HBr |
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Occasionally, alkylation will occur also at oxygen, thus ] gives both the sulfone and the isomeric ] ester. |
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==Use== |
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The original use of the compound was as industrial bleaching agent and as a reducing agent for ]ing.<ref name=Ull/> 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 ] for aquaria as it rapidly reduces ] and ] and reacts with ] to form the innocuous aminomethylsulfinate ion.<ref>{{ cite patent | country = EP | number = 0278515 | status = patent | title = Chloramine removing means | inventor = Günter Ritter | gdate = 1988-08-17 | assign1 = ] }}</ref> |
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It is also used as an antioxidant in pharmaceutical formulation. |
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The compound has been used increasingly in commercial cosmetic hair dye colour removers despite the generation of ], a known human ]. |
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It has a variety of specialized applications in ].<ref>Dittmer, Donald C "Sodium Hydroxymethanesulfinate" e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001. {{doi|10.1002/047084289X.rs083}}</ref><ref>{{cite journal | doi = 10.1021/cr100175t| pmid = 22107104| title = Rongalite: A Useful Green Reagent in Organic Synthesis| journal = Chemical Reviews| volume = 112| issue = 3| pages = 1650–1680| year = 2011| last1 = Kotha| first1 = Sambasivarao| last2 = Khedkar| first2 = Priti}}</ref> |
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==Related compounds== |
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The zinc complex Zn(HOCH<sub>2</sub>SO<sub>2</sub>)<sub>2</sub> is marketed under the trademarks Decroline, Decolin, and Safolin. This compound is an additive in polymers and textiles.<ref>{{ cite journal |author1=Masciocchi, N. |author2=Rigamonti, C. |author3=Maspero, A. | title = Poly | journal = ] | year = 2005 | volume = 61 | issue = 12 | pages = m2683–m2685 | doi = 10.1107/S1600536805038237 }}</ref> |
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Sodium hydroxymethanesulfinate is called Rongalite C. |
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Calcium hydroxymethanesulfinate is called Rongalite H. |
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==References== |
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{{reflist|2}} |
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==Further reading== |
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*{{ cite book |author1=Holleman, A. F. |author2=Wiberg, E. | title = Inorganic Chemistry | publisher = Academic Press | location = San Diego | year = 2001 | isbn = 978-0-12-352651-9 }} |
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*{{ cite journal | authorlink1 = Lev Aleksandrovich Chugaev | author1 = Tschugaeff, L. | author2 = Chlopin, W. | title = Beiträge zur Kenntnis des Reduktionsvermögens der schwefligen Säure. I. Einwirkung von Natriumhydrosulfit auf Tellur und Selen | journal = ] | year = 1914 | volume = 47 | issue = 1 | pages = 1269–1275 | doi = 10.1002/cber.191404701202 | url = https://zenodo.org/record/1426545 }} |
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*{{ cite journal |author1=Steudel, R. |author2=Münchow, V. | title = Sulphur compounds: CLIX. Determination of Dithionite (S<sub>2</sub>O<sub>4</sub><sup>2−</sup>) and Hydroxymethanesulphinate (HOCH<sub>2</sub>SO<sub>2</sub><sup>−</sup>; Rongalite) by Ion-Pair Chromatography | journal = ] | year = 1992 | volume = 623 | issue = 1 | pages = 174–177 | doi = 10.1016/0021-9673(92)85314-J }} |
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