Diethylmalonat Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
Aussehen Eigenschaften
C7H12O4; Diethylmalonat, Ethylmalonat, Malonester. Farblose Flüssigkeit mit aromatischem Geruch.
Gefahren für Mensch und Umwelt
Brennbar.
Reizt die Augen und die Haut
LD
50 (oral, Ratte): 15000 mg/kg
Schutzmaßnahmen und Verhaltensregeln
Geeignete Schutzhandschuhe als kurzzeitiger Spritzschutz.
Verhalten im Gefahrfall
Mit flüssigkeitsbindendem Material, z.B. Rench Rapid aufnehmen. Der Entsorgung zuführen. Nachreinigen.
Kohlendioxid, Pulver, Schaum.
Brennbar.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 10 Minuten ausspülen. Augenarzt hinzuziehen.
Nach Einatmen: Frischluft.
Nach Verschlucken: Reichlich Wasser trinken lassen. Erbrechen auslösen. Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Als halogenfreie, organische Lösemittelabfälle.
Beschreibung
Diethyl malonate is a diester derivative of malonic acid, a dicarboxylic acid with two carboxyl groups (-COO-) separated by one methylene group (-CH2-). Diethyl malonate is formed by the replacement of the hydroxyl groups (-OH) of malonic acid with ethoxy groups (-OCH2CH3). The hydrogen atoms on the methylene carbon between the two carboxyl groups make this compound acidic. Because of its unique structure, diethyl malonate is reactive and functions as a reagent for organic synthesis and to make products such as barbiturates, pigments, and agrochemicals. Volatile esters are known to have fruity scents and are often used as fragrances and flavorings. Diethyl malonate is a volatile diester that occurs naturally in fruits such as grapes, strawberries, guava, melon, pineapple, and blackberries.
Chemische Eigenschaften
Diethyl malonate has a faint, pleasant, aromatic odor.
Occurrence
Reported found in pineapple, bilberry, Cape gooseberry, cognac, malt whiskey, apple brandy, grape brandy,
port, cider, sherry and red, white, strawberry and bilberry wines.
Verwenden
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.
synthetische
Reacting chloroacetic acid to cyanoacetic acid using sodium cyanide and subsequent saponification; malonic acid is
finally esterified by azeotropic distillation with ethanol in benzene
Allgemeine Beschreibung
Diethyl malonate is diethyl ester of malonic acid. Acylation of diethyl malonate using magnesium chloride and triethylamine is reported. K
2CO
3-catalyzed 1,4-addition reaction of diethyl malonate with various substituted 1,2-allenic ketones yields polyfunctionalized β,γ-unsaturated enones.
Sicherheitsprofil
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.
Stoffwechsel
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).
läuterung methode
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.]
Diethylmalonat Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
5-Nitropyridine-2-carboxylic acid
Ethyl-1,2,3,4-tetrahydro-2,4-dioxopyrimidin-5-carboxylat
4-Butyl-1,2-diphenyl-3,5-pyrazoli-dindion
3-CARBETHOXYUMBELIFERONE
5,7-BIS(TRIFLUOROMETHYL)-4-HYDROXYQUINOLINE
2-(TRIFLUOROMETHYL)-4-HYDROXYPYRIMIDINE-5-CARBOXYLIC ACID
Enoxacin
2-ETHOXY-MALONIC ACID DIETHYL ESTER
5-NITROBENZOFURAN-2-CARBOXYLIC ACID
Ethyl-2-oxopiperidin-3-carboxylat
2,4-Dihydroxypyrimidin-5-carbonsure
Diethylaminomalonat
5-CHLORO-BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER
2-Amino-6-hydroxypyrimidin-4(3H)-one ,97%
2-Mercapto-4,6-dimethoxypyrimidine
ETHYL 4-HYDROXY-6-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLATE
4-Chlor-7-(trifluormethyl)chinolin
Diethylbutylmalonat
5,7-BIS(TRIFLUOROMETHYL)-4-CHLOROQUINOLINE
2-Benzofurancarboxylic acid ethyl ester
ETHYL 2-(ETHYLTHIO)-4-HYDROXYPYRIMIDINE-5-CARBOXYLATE
Gliclazid
4-Chloro-6-methoxy-2-(methylthio)pyrimidine
ETHYL 7-METHOXYBENZOFURAN-2-CARBOXYLATE
4-CHLORO-2-METHANESULFONYL-6-METHOXY-PYRIMIDINE
Ethoxylated
Diethyl-(2-cyanethyl)malonat
2,4,5-Trifluorophenylacetic acid
4,6-Dichloro-2-(methylsulfonyl)pyrimidine
ETHYL 4-CHLORO-6-(TRIFLUOROMETHYL)-3-QUINOLINECARBOXYLATE
2-amino-6-chloropyrimidin-4(3H)-one
4-HYDROXY-5,7-BIS-TRIFLUOROMETHYL-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
2-MERCAPTOPYRIMIDINE-4,6-DIOL
Diethylchlormalonat
Triethylethan-1,1,2-tricarboxylat
4,6-Dihydroxy-2-methylpyrimidine
Sulfamonomethoxine
2-Hexyldecansure
cyclopentylessigsaeure
5,7-BIS(TRIFLUOROMETHYL)-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID
