Tartronic acid

Structural formula
General
Surname	Tartronic acid
other names	Hydroxymalonic acid; 2-hydroxypropanedioic acid;
Molecular formula	C 3 H 4 O 5
Brief description	colorless prisms
External identifiers / databases
EC number	201-301-1
ECHA InfoCard	100.001.184
PubChem	45
Wikidata	Q425473
properties
Molar mass	120.06 g mol −1
Physical state	firmly
Melting point	158-160 ° C (dec.)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tartronic acid ( hydroxymalonic acid ) is the simplest hydroxy dicarboxylic acid . It does not occur in nature because of its sensitivity to oxidation.

It can be produced on a laboratory scale by hydrolysis of bromomalonic acid with silver hydroxide . Acetobacter acetosum forms 2-ketogluconic acid in a glucose medium , which is broken down into tartronic acid in a subsequent reaction.

It crystallizes in colorless prisms, which melt at 158–160 ° C with decomposition ( decarboxylation to glycolic acid ). It can be oxidized to mesoxalic acid by catalytic oxidation on platinum-bismuth catalysts with air .

Individual evidence

↑ ^a ^b Beyer / Walter : Textbook of Organic Chemistry , 19th edition, S. Hirzel Verlag, Stuttgart 1981, ISBN 3-7776-0356-2 , p. 319.
↑ ^a ^b ^c data sheet Tartronic acid from Sigma-Aldrich , accessed on May 15, 2017 ( PDF ).
↑ AN Hall, D. Kulka, TK Walker: Formation of Arabinose, Ribulose and Tartronic Acid from 2- Keto - D- gluconic Acid , in: Biochem J. , 1955 , 60 (2), pp. 271-274; PMC 1215693 (free full text); PMID 14389236 .
↑ P. Fordham, M. Besson, P. Gallezot: Catalytic oxidation with air of tartronic acid to mesoxalic acid on bismuth-promoted platinum , in: Catal. Lett. , 1997 , 46 (3-4), pp. 195-199; doi : 10.1023 / A: 1019082905366 .

Web links

US patent 4319045: "Process for production of a tartronic acid solution", max 20% by-product in addition to other dicarboxylic acids
US patent 5750037: Use of tartronic acid as an oxygen scavenger
Literature review on synthesis

[BEYER_WALTER_19-1] Beyer / Walter : Textbook of Organic Chemistry , 19th edition, S. Hirzel Verlag, Stuttgart 1981, ISBN 3-7776-0356-2 , p. 319.

[Sigma-2] ta sheet Tartronic acid from Sigma-Aldrich , accessed on May 15, 2017 ( PDF ).

[3] AN Hall, D. Kulka, TK Walker: Formation of Arabinose, Ribulose and Tartronic Acid from 2- Keto - D- gluconic Acid , in: Biochem J. , 1955 , 60 (2), pp. 271-274; PMC 1215693 (free full text); PMID 14389236 .

[4] P. Fordham, M. Besson, P. Gallezot: Catalytic oxidation with air of tartronic acid to mesoxalic acid on bismuth-promoted platinum , in: Catal. Lett. , 1997 , 46 (3-4), pp. 195-199; doi : 10.1023 / A: 1019082905366 .