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Malonic acid reacts as a typical carboxylic acid forming amide, ester, and chloride derivatives. [13] Malonic anhydride can be used as an intermediate to mono-ester or amide derivatives, while malonyl chloride is most useful to obtain diesters or diamides. In a well-known reaction, malonic acid condenses with urea to form barbituric acid.
In forming diethyl malonate from malonic acid, the hydroxyl group (−OH) on both of the carboxyl groups is replaced by an ethoxy group (−OEt; −OCH 2 CH 3). The methylene group (−CH 2 −) in the middle of the malonic part of the diethyl malonate molecule is neighboured by two carbonyl groups (−C(=O)−). [4]
In this reaction the carbonyl group is an aldehyde or a ketone. The catalyst is usually a weakly basic amine. The active hydrogen component has the forms: [3] Z−CH 2 −Z or Z−CHR−Z for instance diethyl malonate, Meldrum's acid, ethyl acetoacetate or malonic acid, or cyanoacetic acid. [1] Z−CHRR', for instance nitromethane.
The malonic ester synthesis is a chemical reaction where diethyl malonate or another ester of malonic acid is alkylated at the carbon alpha (directly adjacent) to both carbonyl groups, and then converted to a substituted acetic acid. [2] Reaction formula
Dimethyl malonate is a diester derivative of malonic acid. It is a common reagent for organic synthesis used, for example, as a precursor for barbituric acid. It is also used in the malonic ester synthesis. It can be synthesized from dimethoxymethane and carbon monoxide. [2]
Disodium malonate is a sodium salt of malonic acid with the chemical formula CH 2 (COONa) 2. It is a white crystal soluble in water but not in alcohols, esters or benzene. It can be prepared from the reaction of sodium hydroxide and malonic acid: CH 2 (COOH) 2 + 2 NaOH → CH 2 (COONa) 2 + 2 H 2 O
Malic acid is an organic compound with the molecular formula HO 2 CCH(OH)CH 2 CO 2 H. It is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive. Malic acid has two stereoisomeric forms (L- and D-enantiomers), though only the L-isomer exists naturally.
Maleic acid has a heat of combustion of -1,355 kJ/mol., [6] 22.7 kJ/mol higher than that of fumaric acid. Maleic acid is more soluble in water than fumaric acid. The melting point of maleic acid (135 °C) is also much lower than that of fumaric acid (287 °C). As confirmed by X-ray crystallography, maleic acid is planar.