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Sodium nitrite

Sodium nitrite
Sodium nitrite
The nitrite anion (space-filling model)
The sodium cation
Identifiers
 Y
ATC code V03
ChEBI  N
ChEMBL  Y
ChemSpider  Y
EC number 231-555-9
Jmol-3D images Image
PubChem
RTECS number RA1225000
UNII  Y
UN number 1500
Properties
NaNO2
Molar mass 68.9953 g/mol
Appearance white or slightly yellowish solid
Density 2.168 g/cm3
Melting point 271 °C (520 °F; 544 K) (decomposes at 320° C)
71.4 g/100 mL (0 °C)
84.8 g/100 mL (25 °C)
160 g/100 mL (100 °C)
Solubility soluble in methanol (4.4 g/100 mL)
ethanol
slightly soluble in diethyl ether (0.3 g/100 mL)
very soluble in ammonia
Acidity (pKa) ~9
1.65
Structure
Trigonal
Thermochemistry
106 J/mol K
−359 kJ·mol−1[1]
-295 kJ/mol
Hazards
Safety data sheet External MSDS
Oxidizing Agent O Toxic T Dangerous for the Environment (Nature) N
R-phrases R50
S-phrases (S1/2), S45, S61
NFPA 704
0
3
1
OX
489 °C (912 °F; 762 K)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)
180 mg/kg (rats, oral)
Related compounds
Other anions
Lithium nitrite
Sodium nitrate
Other cations
Potassium nitrite
Ammonium nitrite
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: Y/N?)

Sodium nitrite is the botulism.

It is on the health system.[2]

Contents

  • Uses 1
    • Industrial chemistry 1.1
    • Medicine 1.2
    • Food additive 1.3
      • Inhibition of microbial growth 1.3.1
      • Taste and color 1.3.2
      • Inhibition of lipid oxidation 1.3.3
  • Toxicity 2
    • Humane toxin for feral hogs/wild boar control 2.1
    • Nitrosamines 2.2
  • Mechanism of action 3
  • Production 4
  • Chemical reactions 5
  • References 6
  • External links 7

Uses

Industrial chemistry

The main use of sodium nitrite is for the industrial production of organonitrogen compounds. It is a reagent for conversion of amines into diazo compounds, which are key precursors to many dyes, such as diazo dyes. Nitroso compounds are produced from nitrites. These are used in the rubber industry.[3]

Other applications include uses in photography. It may also be used as an electrolyte in electrochemical grinding manufacturing processes, typically diluted to about 10% concentration in water. It is used in a variety of metallurgical applications, for phosphatizing and detinning.

Sodium nitrite is an effective corrosion inhibitor and is used as an additive in industrial greases,[4] as an aqueous solution in closed loop cooling systems, and in a molten state as a heat transfer medium.[5]

Medicine

Sodium nitrite can be used as part of an intravenous mixture with sodium thiosulfate to treat cyanide poisoning.

It is on the health system.[6]

There is also research to investigate its applicability towards treatments for heart attacks, brain aneurysms, pulmonary hypertension in infants, and Pseudomonas aeruginosa infections.[7][8]

Food additive

In the early 1900s, irregular

  • ATSDR - Case Studies in Environmental Medicine - Nitrate/Nitrite Toxicity U.S. Department of Health and Human Services (public domain)
  • International Chemical Safety Card 1120.
  • National Center for Home Food Preservation Nitrates and Nitrites.
  • Mice1TR-495: Toxicology and Carcinogenesis Studies of Sodium Nitrite (CAS NO. 7632-00-0) Drinking Water Studies in F344/N Rats and B6C3F.
  • Nitrite in Meat

External links

  1. ^ Zumdahl, Steven S. (2009). Chemical Principles 6th Ed. Houghton Mifflin Company. p. A23.  
  2. ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014. 
  3. ^ a b Wolfgang Laue, Michael Thiemann, Erich Scheibler, Karl Wilhelm Wiegand "Nitrates and Nitrites" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim.doi:10.1002/14356007.a17_265. Article Online Posting Date: 15 June 2000
  4. ^ Krakhmalev, S. I.; Vorotnikova, V. A.; Ten, N. V.; Taranova, N. V. (1984). "Determination of sodium nitrite in complex sodium grease". Chemistry And Technology Of Fuels And Oils 20 (12): 612–613.  
  5. ^ "Sodium Nitrite". General Chemical. Retrieved 2012-09-28. 
  6. ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 28 April 2014. 
  7. ^ "Hot dog preservative could be disease cure". USA Today. Associated Press. Sep 5, 2005. 
  8. ^ Roxanne Khamsi (27 January 2006). "Food preservative fights cystic fibrosis complication". NewScientist.com. 
  9. ^ a b c d e f g h Sindelar, Jeffrey; Andrew Milkowski (March 2012). "Human safety controversies surrounding nitrate and nitrite in the diet". Nitric Oxide 26: 259–266.  
  10. ^ UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 27 October 2011. 
  11. ^ http://ec.europa.eu/food/fs/sc/scf/reports/scf_reports_38.pdf
  12. ^ US Food and Drug Administration: "Listing of Food Additives Status Part II". Retrieved 27 October 2011. 
  13. ^ Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". Retrieved 27 October 2011. 
  14. ^ a b Milkowski, Andrew; Harsha Garg; James Couglin; Nathan Bryan (January 2010). "Nutritional epidemiology in the context of nitric oxide biology: Risk-Benefit evaluation for dietary nitrite and nitrate". Nitric Oxide 22 (2): 110–119.  
  15. ^ a b c d e f g h i j k l Sindelar, Jeffrey; Andrew Milkowski (November 2011). "Sodium Nitrite in Processed Meat and Poultry Meats: A Review of Curing and Examining the Risk/Benefit of Its Use". American Meat Science Association 3: 1–14. 
  16. ^ http://msds.chem.ox.ac.uk/SO/sodium_nitrite.html
  17. ^ a b Dennis, M J; Wilson, L A (2003). "Nitrates and Nitrites". Encyclopedia of Food Sciences and Nutrition. p. 4136.  
  18. ^ a b Leszczyńska, Teresa; Filipiak-Florkiewicz, Agnieszka; Cieślik, Ewa; Sikora, ElżBieta; Pisulewski, Paweł M. (2009). "Effects of some processing methods on nitrate and nitrite changes in cruciferous vegetables". Journal of Food Composition and Analysis 22 (4): 315–321.  
  19. ^ Correia, Manuela; Barroso, ÂNgela; Barroso, M. FáTima; Soares, DéBora; Oliveira, M.B.P.P.; Delerue-Matos, Cristina (2010). "Contribution of different vegetable types to exogenous nitrate and nitrite exposure". Food Chemistry 120 (4): 960–966.  
  20. ^ Meulemans, A.; Delsenne, F. (1994). "Measurement of nitrite and nitrate levels in biological samples by capillary electrophoresis". Journal of Chromatography B 660 (2): 401–404.  
  21. ^ Southan, G; Srinivasan, A (1998). "Nitrogen Oxides and Hydroxyguanidines: Formation of Donors of Nitric and Nitrous Oxides and Possible Relevance to Nitrous Oxide Formation by Nitric Oxide Synthase". Nitric Oxide 2 (4): 270–86.  
  22. ^ Lapidge, Steven; J. Wishart; M. Smith; L. Staples (2009). "Is America Ready for a Humane Feral Pig Toxicant?". Proceedings of the 13th Wildlife Damage Management Conference: 49–59. 
  23. ^ Cowled, BD; SJ Lapidge; S. Humphrys; L Staples (2008). "Nitrite Salts as Poisons in Baits for Omnivores". International Patent WO/2008/104028. 
  24. ^ S. Porter & T. Kuchel (2010). Assessing the humaness and efficacy of a new feral pig bait in domestic pigs. Study PC0409 (PDF). Canberra, South Australia: Veterinary Services Division, Institute of Medical and Veterinary Science. p. 11. 
  25. ^ https://www.youtube.com/watch?v=GigpxLNbgeg&spfreload=1
  26. ^ "The epidemiological enigma of gastric cancer rates in the US: was grandmother's sausage the cause?", International Journal of Epidemiology (2000) accessdate 2000-08-01
  27. ^ C.W. Mackerness, S.A. Leach, M.H. Thompson and M.J. Hill (1989). "The inhibition of bacterially mediated N-nitrosation by vitamin C: relevance to the inhibition of endogenous N-nitrosation in the achlorhydric stomach". Carcinogenesis 10 (2): 397–9.  
  28. ^ Nitrosamines and Cancer by Richard A. Scanlan, Ph.D.
  29. ^ Cancer Res. 1983 May;43(5 Suppl):2435s-2440s.
  30. ^ Nollet, Toldra, D (2015). Handbook of Food Analysis, Third Edition - Two Volume Set. p. 290.  
  31. ^ Williams, D (2004). "Reagents effecting nitrosation". Nitrosation Reactions and the Chemistry of Nitric Oxide. p. 1.  
  32. ^ "Heading Off Migraine Pain". FDA Consumer magazine.  
  33. ^ Miranda Hitti (17 April 2007). "Study: Cured Meats, COPD May Be Linked". WebMD Medical News. 
  34. ^ Jiang, R.; Paik, D. C.; Hankinson, J. L.; Barr, R. G. (2007). "Cured Meat Consumption, Lung Function, and Chronic Obstructive Pulmonary Disease among United States Adults". American Journal of Respiratory and Critical Care Medicine 175 (8): 798–804.  
  35. ^ Najm, Issam; Trussell, R. Rhodes (February 2001). "NDMA Formation in Water and Wastewater". Journal AWWA 93 (2): 92–99. 
  36. ^ Donald D. Bills, Kjell I. Hildrum, Richard A. Scanlan, Leonard M. Libbey (May 1973). "Potential precursors of N-nitrosopyrrolidine in bacon and other fried foods". J. Agric. Food Chem. 21 (5): 876–7.  
  37. ^ "Sodium Azide". Hazardous Waste Management.  
  38. ^ Committee on Prudent Practices for Handling, Storage, and Disposal of Chemicals in Laboratories, Board on Chemical Sciences and Technology, Commission on Physical Sciences, Mathematics, and Applications, National Research Council. (1995). Prudent practices in the laboratory: handling and disposal of chemicals. Washington, D.C.:  
  39. ^ Stern, Kurt H. (1972). "High Temperature Properties and Decomposition of Inorganic Salts; Part 3. Nitrates and Nitrites" (PDF). J. Phys. Chem. (US Naval Research Laboratory) 1 (3): 750–751.  

References

2NO
2
+ H
2
O
HNO
3
+ HNO
2

The nitrogen dioxide of the prior decomposition is then routed through a condensor or fractional distillation apparatus to react with water and yield nitric acid:

2HNO
2
NO
2
+ NO + H
2
O

The nitrous acid then, under normal conditions, decomposes:

2NaNO
2
+ H
2
SO
4
→ 2HNO
2
+ Na
2
SO
4

Sodium nitrite can also be used in the production of nitrous acid via sulfuric acid. This reaction first yields nitrous acid and sodium sulfate:

2 NaNO2 → Na2O + NO + NO2

Above 330 °C sodium nitrite decomposes (in air) to sodium oxide, nitrogen(II) oxide and nitrogen dioxide.[39]

2 NaN3 + 2 Na NO2 + 2 H+ → 3 N2 + 2 NO + 2 Na+ + 2 H2O

In the laboratory, sodium nitrite can be used to destroy excess sodium azide.[37][38]

Chemical reactions

In former times, sodium nitrite was prepared by reduction of sodium nitrate with various metals.[3]

The conversion is sensitive to the presence of oxygen, which can lead to varying amounts of sodium nitrate.

2 NaOH + NO2 + NO → 2 NaNO2 + H2O

The salt is prepared by treating sodium hydroxide with mixtures of nitrogen dioxide and nitric oxide:

Production

If this nucleophilic substitution reaction occurs at a crucial site in a biomolecule, it can disrupt normal cell functions, leading to cancer or cell death.

R-N2+ (diazonium ion) → R+ (carbocation) + N2 (leaving group) + :Nu (biological nucleophiles) → R-Nu

Certain nitrosamines such as N-nitrosodimethylamine[35] and N-nitrosopyrrolidine[36] form carbocations that react with biological nucleophiles (such as DNA or an enzyme) in the cell.

R2N-N=O (nitrosamine) + (acid or heat) → R-N2+ (diazonium ion)

In the presence of acid (such as in the stomach) or heat (such as via cooking), nitrosamines are converted to diazonium ions.

R2NH (amines) + NaNO2 (sodium nitrite) → R2N-N=O (nitrosamine)

Carcinogenic nitrosamines are formed when amines that occur naturally in food react with sodium nitrite found in cured meat products.

Mechanism of action

One study has found a correlation between highly frequent ingestion of meats cured with pink salt and the COPD form of lung disease. The study's researchers suggest that the high amount of nitrites in the meats was responsible; however, the team did not prove the nitrite theory. Additionally, the study does not prove that nitrites or cured meat caused higher rates of COPD, merely a link. The researchers did adjust for many of COPD's risk factors, but they commented they cannot rule out all possible unmeasurable causes or risks for COPD.[33][34]

Sodium nitrite consumption has also been linked to the triggering of migraines in individuals who already suffer from them.[32]

A principal concern about sodium nitrite is the formation of carcinogenic nitrosamines in meats containing sodium nitrite when meat is charred or overcooked. Such carcinogenic nitrosamines can also be formed from the reaction of nitrite with secondary amines under acidic conditions (such as occurs in the human stomach) as well as during the curing process used to preserve meats. Dietary sources of nitrosamines include US cured meats preserved with sodium nitrite as well as the dried salted fish eaten in Japan. In the 1920s, a significant change in US meat curing practices resulted in a 69% decrease in average nitrite content. This event preceded the beginning of a dramatic decline in gastric cancer mortality.[26] About 1970, it was found that ascorbic acid (vitamin C), an antioxidant, inhibits nitrosamine formation.[27] Consequently, the addition of at least 550 ppm of ascorbic acid is required in meats manufactured in the United States. Manufacturers sometimes instead use erythorbic acid, a cheaper but equally effective isomer of ascorbic acid. Additionally, manufacturers may include alpha-tocopherol (vitamin E) to further inhibit nitrosamine production. Alpha-tocopherol, ascorbic acid, and erythorbic acid all inhibit nitrosamine production by their oxidation-reduction properties. Ascorbic acid, for example, forms dehydroascorbic acid when oxidized, which when in the presence of nitrosonium, a potent nitrosating agent formed from sodium nitrite, reduces the nitrosonium into nitric oxide.[28] The nitrosonium ion formed in acidic nitrite solutions is commonly[29][30] mislabeled nitrous anhydride, an unstable nitrogen oxide that cannot not exist in vitro.[31]

Nitrosamines

Because of sodium nitrite's high level of toxicity to swine (Sus scrofa) it is now being developed in Australia to control feral pigs and wild boar.[22][23] The sodium nitrite induces methemoglobinemia in swine, i.e., it reduces the amount of oxygen that is released from hemoglobin, so the animal will feel faint and pass out, and then die in a humane manner after first being rendered unconscious.[24] The Texas Parks and Wildlife Department operates a research facility at Kerr Wildlife Management Area, where they examine feral pig feeding preferences and bait tactics to administer Sodium nitrite.[25]

Humane toxin for feral hogs/wild boar control

While this chemical will prevent the growth of bacteria, it can be toxic in high amounts for animals and humans. Sodium nitrite's LD50 in rats is 180 mg/kg and its human LDLo is 71 mg/kg, meaning a 65 kg person would likely have to consume at least 4.6 g to result in death.[16] To prevent toxicity, sodium nitrite (blended with salt) sold as a food additive is dyed bright pink to avoid mistaking it for plain salt or sugar. Nitrites are not naturally occurring in vegetables in significant quantities.[17] However, nitrites are found in commercially available vegetables and a study in an intensive agricultural area in northern Portugal found residual nitrite levels in 34 vegetable samples, including different varieties of cabbage, lettuce, spinach, parsley and turnips ranged between 1.1 and 57 mg/kg, e.g. white cauliflower (3.49 mg/kg) and green cauliflower (1.47 mg/kg).[18][19] Boiling vegetables lowers nitrate but not nitrite.[18] Fresh meat contains 0.4-0.5 mg/kg nitrite and 4–7 mg/kg of nitrate (10–30 mg/kg nitrate in cured meats).[17] The presence of nitrite in animal tissue is a consequence of metabolism of nitric oxide, an important neurotransmitter.[20] Nitric oxide can be created de novo from nitric oxide synthase utilizing arginine or from ingested nitrate or nitrite.[21]

Toxicity

Sodium nitrite is also able to effectively delay the development of oxidative rancidity.[15] Lipid oxidation is considered to be a major reason for the deterioration of quality of meat products (rancidity and unappetizing flavors).[15] Sodium nitrite acts as an antioxidant in a mechanism similar to the one responsible for the coloring affect.[15] Nitrite reacts with heme proteins and metal ions, neutralizing free radicals by nitric oxide (one of its byproducts).[15] Neutralization of these free radicals terminates the cycle of lipid oxidation that leads to rancidity.[15]

Inhibition of lipid oxidation

The appearance and taste of meat is an important component of consumer acceptance.[9] Sodium nitrite is responsible for the desirable red color (or shaded pink) of meat.[9] Very little nitrite is needed to induce this change.[9] It has been reported that as little as 2 to 14 parts per million (ppm) is needed to induce this desirable color change.[15] However, to extend the life-span of this color change, significantly higher levels are needed.[15] The mechanism responsible for this color change is the formation of nitrosylating agents by nitrite, which has the ability to transfer nitric oxide that subsequently reacts with myoglobin to produce the cured meat color.[15] The unique taste associated with cured meat is also affected by the addition of sodium nitrite.[9] However, the mechanism underlying this change in taste is still not fully understood.[15]

Taste and color

[15].Escherichia coli and Salmonella enteric pathogens such as gram-negative It is generally agreed upon that sodium nitrite is not considered effective for controlling [15] also affects sodium nitrites effectiveness.bacteria Furthermore, the type of [15] content.iron, salt concentration, reductants present and pH Even though the inhibitory mechanisms for sodium nitrite are not well known, its effectiveness depends on several factors including residual nitrite level, [9] Sodium nitrite is well known for its role in inhibiting the growth of

Inhibition of microbial growth

[13] and Australia and New Zealand.[12] USA[11][10],EU (E249) is used in the same way. It is approved for usage in the Potassium nitrite E250. E number In the European Union it may be used only as a mixture with salt containing at most 0.0625% sodium nitrite. It has the [9], extended storage life and improving desirable color/taste.food safety with improved meat The ability of sodium nitrite to address the above-mentioned issues has led to production of [9]

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