Diethyl malonate Chemical Properties
- Melting point:
- -50 °C
- Boiling point:
- 199 °C(lit.)
- 1.055 g/mL at 25 °C(lit.)
- vapor density
- 5.52 (vs air)
- vapor pressure
- 1 mm Hg ( 40 °C)
- 2375 | DIETHYL MALONATE
- refractive index
- Flash point:
- 212 °F
- storage temp.
- Store below +30°C.
- 20.8g/l (External MSDS)
- 13.5(at 25℃)
- explosive limit
- Water Solubility
- Miscible with ethyl alcohol, ether, chloroform and benzene. Slightly miscible with water.
- JECFA Number
- Stable. Combustible. Incompatible with strong oxidizing agents,
- CAS DataBase Reference
- 105-53-3(CAS DataBase Reference)
- NIST Chemistry Reference
- Propanedioic acid, diethyl ester(105-53-3)
- EPA Substance Registry System
- Diethyl malonate (105-53-3)
Diethyl malonate Usage And Synthesis
As an organic compound, diethyl malonate belongs to the diethyl ester of malonic acid, which is present naturally in guava fruits, melons, grapes, pineapples, blackberries and strawberries as a colorless liquid with an apple-like odor. It is a flavor ingredient commonly found in perfumes, artificial flavorings, alcoholic beverages, various wines and spirits due to its natural pleasant odor. It is also used as an essential intermediate in the syntheses of numerous pharmaceuticals, such as barbiturates, vitamins B1 and B6, non-steroidal anti-inflammatory agents. Besides, diethyl malonate is also involved in organic synthesis of other compounds, such as alpha-aryl malonates, mono-substituted and di-substituted acetic acid. And it can react with benzaldehyde for the production of diethyl benzylidenemalonate in Knoevenagel condensation reaction.
Diethyl malonate has a faint, pleasant, aromatic odor.
Reported found in pineapple, bilberry, Cape gooseberry, cognac, malt whiskey, apple brandy, grape brandy, port, cider, sherry and red, white, strawberry and bilberry wines.
Diethyl Malonate occurs naturally in grapes and strawberries. It is used in the preparation of barbiturates, artificial flavourings, vitamin B1, and vitamin B6 as well as in perfumes.
manufacture of barbiturates.
Reacting chloroacetic acid to cyanoacetic acid using sodium cyanide and subsequent saponification; malonic acid is finally esterified by azeotropic distillation with ethanol in benzene
Taste threshold values
Taste characteristics at 50 ppm: sweet and fruity with apple and pineapple nuances.
Mildly toxic by ingestion. A skin irritant. Combustible liquid when exposed to heat or flame; can react with oxidizing materials. To fight fire, use water to blanket fire, foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.
When the ester was fed to chicks at a level of 5% in the diet, 32% of the energy from diethyl malonate was available (Yoshida et al. 1970). Hydrolysis of diethyl malonate would produce ethanol and malonic acid, which is a relatively strong acid and acts as an inhibitor of enzymes, including succinic dehydrogenase (Fassett, 1963). Malonic acid injected into rats or rabbits is excreted largely unchanged, but also causes increased excretion of citric and a-ketoglutaric acids (Krebs, Salvin & Johnson, 1938). Some malonate may be metabolized through the tricarboxylic acid cycle, with decarboxylation to acetate followed by transformation to succinate, which has been detected in rat urine (Lee & Lifson, 1951). Diethyl malonate was hydrolysed by adipose-tissue lipase (Lynn & Perryman, 1960) and to the monoester by α-chymotrypsin (Cohen & Crossely, 1964). It was oxidized in 110 min to the extent of 34% by the homogenized mycelium of urethane-grown Streptomyces nitrifica (Schatz, Trelawny, Schatz & Mohan, 1957).
If too impure (IR, NMR) the ester (250g) is heated on a steam bath for 36hours with absolute EtOH (125mL) and conc H2SO4 (75mL), then fractionally distilled under reduced pressure. Otherwise fractionally distil it under reduced pressure and collect the steady boiling middle fraction. [Beilstein 2 IV 1881.]
Diethyl malonate Preparation Products And Raw materials
- Malonic acid
- Diethyl malonate
- Ethyl propionate
- ACETAMIDO DIETHYL MALONATE
- Diethyl ether
- Diethyl oxalate
- Diethyl fluoromalonate
- Diethyl ethylmalonate
- Ethylene glycol diethyl ether
- Ethyl formate
- Ethyl acetate