Ullmann`s:
Acetonedicarboxylic AcidAcetonedicarboxylic acid [542-05-2] , 3-oxoglutaric acid, b-ketoglutaric acid, 3-oxopentane dicarboxylic acid, HOOC–CH2–CO–CH2–COOH, Mr 146.10, was first isolated and described by V. PECHMANN [48] , [49].
Physical Properties. Acetonedicarboxylic acid forms colorless crystals that are readily soluble in water and ethanol, and sparingly soluble in trichloromethane and diethyl ether. It melts with decomposition at 138 °C. The dissociation constants (in 0.01 M solution) are K125= 4.68×10–4 and K225= 5.37×10–5 [50].
Chemical Properties. On heating above its melting point, acetonedicarboxylic acid decomposes into carbon dioxide and acetone [49]. When acetonedicarboxylic acid is warmed in water, a two-step decomposition occurs with acetoacetic acid [541-50-4] as an intermediate that decomposes further to acetone and carbon dioxide [50]. The decomposition is catalyzed by metal ions and protons [51]. Phenols react with acetonedicarboxylic acid in the presence of dehydrating agents to form coumarin derivatives [52][53][54].
Production. Acetonedicarboxylic acid is produced from citric acid [77-92-9] by many industrial processes that differ only slightly [55],[56]. Citric acid is treated with oleum and reacts to yield acetonedicarboxylic acid via decarbonylation and dehydration.
Other possible production methods include reaction of acetone with carbon dioxide [57] , [58] , oxidation of citric acid with chlorosulfuric acid [59] , or reaction of ketene with phosgene [60].
Uses. Acetonedicarboxylic acid is an important starting material in the production of pharmaceutically active alkaloids [61][62][63]. It is also suitable as a stabilizer for natural fats and oils [64] , [65].
Storage and Quality Specifications. Large quantities of acetonedicarboxylic acid can be stored for short periods in tightly closed polyethylene containers in refrigerated areas. The acid must not be stored in metal containers. Laboratory-scale quantities of the pure substance can be kept for longer periods over phosphorus pentoxide in a desiccator [66]. The commercial product has a concentration of ca. 98 %; the purity is determined by titration.
Toxicology. Acetonedicarboxylic acid can cause irritation and acid burns to the eyes, respiratory passages, and skin.
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