Chemistry:Tartronic acid

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Tartronic acid
Tartronic acid.svg
Names
Preferred IUPAC name
Hydroxypropanedioic acid
Other names
tartronic acid,
2-tartronic acid,
hydroxymalonic acid,
2-hydroxymalonic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 201-301-1
KEGG
UNII
Properties
C3H4O5
Molar mass 120.06 g/mol
Appearance white solid
Density 1.849 g/cm3
Melting point 159 °C (318 °F; 432 K) (decomposes)
Hazards
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
0
2
0
Related compounds
Tartaric acid
Malic acid
Mesoxalic acid
Lactic acid
3-Hydroxypropionic acid
Malonic acid
Propionic acid
Oxalic acid
Related compounds
Glyceric acid
Glyceraldehyde
Tartonaldehyde
Glycerol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tartronic acid or 2-hydroxymalonic acid is an organic compound with the structural formula of HOHC(CO2H)2. This dicarboxylic acid is related to malonic acid. It is a white solid. It is produced by oxidation of glycerol:

HOCH
2
CH(OH)CH
2
OH + 2 O
2
→ HO
2
CCH(OH)CO
2
H + 2 H
2
O

Glyceric acid HOCH
2
CH(OH)CO
2
H
is an intermediate.[1][2]

Its derivative, 2-methyltartronic acid, is isomalic acid.[3]

Uses

Oxidation of tartronic acid gives the ketone mesoxalic acid, the simplest oxodicarboxylic acid.[4]

References

  1. Habe, Hiroshi; Fukuoka, Tokuma; Kitamoto, Dai; Sakaki, Keiji (2009). "Biotechnological production of d-glyceric acid and its application". Applied Microbiology and Biotechnology 84 (3): 445–452. doi:10.1007/s00253-009-2124-3. PMID 19621222. 
  2. Yang, Lihua; Li, Xuewen; Chen, Ping; Hou, Zhaoyin (2019). "Selective oxidation of glycerol in a base-free aqueous solution: A short review". Chinese Journal of Catalysis 40 (7): 1020–1034. doi:10.1016/S1872-2067(19)63301-2. 
  3. Roelofsen, G.; Kanters, J. A.; Kroon, J.; Doesburg, H. M.; Koops, T. (1978). "Order–disorder phenomena in structures of carboxylic acids: The structures of fluoromalonic acid and hydroxymalonic acid at 20 and –150°C". Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry 34 (8): 2565–2570. doi:10.1107/S0567740878008596. 
  4. Fordham P.; Besson M.; Gallezot P. (1997). "Catalytic oxidation with air of tartronic acid to mesoxalic acid on bismuth-promoted platinum". Catal. Lett. 46 (3–4): 195–199(5). doi:10.1023/A:1019082905366. https://doi.org/10.1023%2FA%3A1019082905366. Retrieved 2007-07-06. 

External links