Sodium bisulfite

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Sodium bisulfite
Sodium bisulfite.png
Ball-and-stick model of a bisulfite anion (left) and a sodium cation (right)
Identifiers
CAS number 7631-90-5 YesY
PubChem 23665763
ChemSpider 571016 YesY
ChEBI CHEBI:26709 YesY
ChEMBL CHEMBL1689285 N
RTECS number VZ2000000
Jmol-3D images Image 1
Properties
Molecular formula NaHSO3
Molar mass 104.061 g/mol
Appearance White solid
Odor slight sulfurous odor
Density 1.48 g/cm3
Melting point 150 °C (302 °F; 423 K)
Boiling point 315 °C (599 °F; 588 K)
Solubility in water 42 g/100 mL
Refractive index (nD) 1.526
Hazards
EU Index 016-064-00-8
EU classification Harmful (Xn)
R-phrases R22 R31
S-phrases (S2), S25, S46
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point Non-flammable
LD50 2340 mg/kg (oral, rat)[1]
Related compounds
Other anions Sodium sulfite
Sodium metabisulfite
Other cations Potassium bisulfite
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Sodium bisulfite (sodium hydrogen sulfite) is a chemical compound with the chemical formula NaHSO3. Sodium bisulfite is a food additive with E number E222. This salt of bisulfite can be prepared by bubbling sulfur dioxide in a solution of sodium carbonate in water. Sodium bisulfite in contact with chlorine bleach (aqueous solution of sodium hypochlorite) will generate heat and form sodium bisulfate and sodium chloride.

Uses in chemistry[edit]

In organic chemistry sodium bisulfite has several uses. It forms a bisulfite adduct with aldehyde groups and with certain cyclic ketones to a sulfonic acid.[2]

Bisulfite reaction

This reaction has limited synthetic value(s) but it is used in purification procedures. Contaminated aldehydes in a solution precipitate as the bisulfite adduct which can be isolated by filtration. The reverse reaction takes place in presence of a base such as sodium bicarbonate or sodium hydroxide and the bisulfite is liberated as sulfur dioxide.[3]

Bisulfite adduct

Examples of such procedures are described for benzaldehyde,[4] 2-tetralone,[5] citral,[6] the ethyl ester of pyruvic acid[7] and glyoxal.[8] In the ring-expansion reaction of cyclohexanone with diazald, the bisulfite reaction is reported to be able to differentiate between the primary reaction product cycloheptanone and the main contaminant cyclooctanone.[9]

The other main use of sodium bisulfite is as a mild reducing agent in organic synthesis in particular in purification procedures. It can efficiently remove traces or excess amounts of chlorine, bromine, iodine, hypochlorite salts, osmate esters, chromium trioxide and potassium permanganate.

A third use of sodium bisulfite is as a decoloration agent in purification procedures because it can reduce strongly coloured oxidizing agents, conjugated alkenes and carbonyl compounds.

Sodium bisulfite is also the key ingredient in the Bucherer reaction. In this reaction an aromatic hydroxyl group is replaced by an aromatic amine group and vice versa because it is a reversible reaction. The first step in this reaction is an addition reaction of sodium bisulfite to an aromatic double bond. The Bucherer carbazole synthesis is a related organic reaction that uses sodium bisulfite as a reagent.

Uses in food[edit]

While the related compound, sodium metabisulfite, is used in almost all commercial wines to prevent oxidation and preserve flavor, sodium bisulfite is sold by some home winemaking suppliers for the same purpose.[10] In fruit canning, sodium bisulfite is used to prevent browning (caused by oxidation) and to kill microbes.

In the case of wine making, sodium bisulfite releases sulfur dioxide gas when added to water or products containing water. The sulfur dioxide kills yeasts, fungi, and bacteria in the grape juice before fermentation. When the sulfur dioxide levels have subsided (about 24 hours), fresh yeast is added for fermentation.

It is later added to bottled wine to prevent the formation of vinegar if bacteria are present, and to protect the color, aroma and flavor of the wine from oxidation, which causes browning and other chemical changes. The sulfur dioxide quickly reacts with oxidation by-products and prevents them from causing further deterioration.

Sodium bisulfite is also added to leafy green vegetables in salad bars and elsewhere, to preserve apparent freshness, under names like LeafGreen. The concentration is sometimes high enough to cause severe allergic reactions.[11]

Industrial uses[edit]

Sodium bisulfite is a common reducing agent in the chemical industries. As it readily reacts with dissolved oxygen:

2 NaHSO3 + O2 → 2 NaHSO4

It is usually added to large piping systems to prevent oxidative corrosion. In biochemical engineering applications, it is helpful to maintain anaerobic conditions within a reactor. Sodium bisulfite should not be confused with sodium bisulfate which is used as a pH lowering chemical for swimming pools.

In drinking water treatment, sodium bisulfite is often added after super chlorination, to reduce the residual chlorine. Before discharging to the service reservoir.

Bisulfite DNA sequencing[edit]

Further information: Bisulfite sequencing
The chemical reaction that underlies the bisulfite-mediated conversion of cytosine to uracil.

Sodium bisulfite is used in the analysis of methylation status of cytosines in DNA.

In this technique, sodium bisulfite deaminates cytosine into uracil, but does not affect 5-methylcytosine, a methylated form of cytosine with a methyl group attached to carbon 5.

When the bisulfite-treated DNA is amplified via polymerase chain reaction, the uracil is amplified as thymine and the methylated cytosines are amplified as cytosine. DNA sequencing techniques are then used to read the sequence of the bisulfite-treated DNA. Those cytosines that are read as cytosines after sequencing represent methylated cytosines, while those that are read as thymines represent unmethylated cytosines in the genomic DNA.[12]

See also[edit]

References[edit]

  1. ^ http://chem.sis.nlm.nih.gov/chemidplus/rn/7646-93-7
  2. ^ Steven D. Young, Charles T. Buse, and Clayton H. Heathcock (1990), 2-Methyl-2-(Trimethylsiloxy)pentan-3-one, Org. Synth. ; Coll. Vol. 7: 381 
  3. ^ S. A. Buntin and Richard F. Heck (1990), 2-Methyl-3-phenylpropanal, Org. Synth. ; Coll. Vol. 7: 361 
  4. ^ Harold M. Taylor and Charles R. Hauser (1973), α-(N,N-Dimethylamino)phenylacetonitrile, Org. Synth. ; Coll. Vol. 5: 437 
  5. ^ M. D. Soffer, M. P. Bellis, Hilda E. Gellerson, and Roberta A. Stewart (1963), β-Tetralone, Org. Synth. ; Coll. Vol. 4: 903 
  6. ^ Alfred Russell and R. L. Kenyon (1955), Pseudoionone, Org. Synth. ; Coll. Vol. 3: 747 
  7. ^ J. W. Cornforth (1963), Ethyl Pyruvate, Org. Synth. ; Coll. Vol. 4: 467 
  8. ^ Anthony R. Ronzio and T. D. Waugh (1955), Glyoxal Bisulfite, Org. Synth. ; Coll. Vol. 3: 438 
  9. ^ Hyp J. Dauben, Jr., Howard J. Ringold, Robert H. Wade, David L. Pearson, and Arthur G. Anderson, Jr., Cycloheptanone, Org. Synth. ; Coll. Vol. 4: 221 
  10. ^ The Many Uses Of Sodium Bisulfite
  11. ^ Albertson, Timothy Eugene (2006). Bronchial Asthma: A Guide for Practical Understanding and Treatment (Current Clinical Practice) (fifth ed.). Totowa, NJ: Humana Press. pp. 260–266. ISBN 1-58829-872-8. Retrieved 2011-11-11. 
  12. ^ Frommer, M.; McDonald, L. E.; Millar, D. S.; Collis, C.M.; Watt, F.; Grigg, G.W.; Molloy P.L.; Paul, C.L. (1992). "A genomic sequencing protocol that yields a positive display of 5-methylcytosine residues in individual DNA strands" (free full text). PNAS 89 (5): 1827–31. doi:10.1073/pnas.89.5.1827. PMC 48546. PMID 1542678.