말론산 디에틸 C화학적 특성, 용도, 생산
물성
무색 투명 액체로서 향기로운 냄새가있다. 융점은 -50 ° C입니다. 끓는점은 198-199 ℃ (95 ℃ /2.67kPa)이다. 밀도는 1.055-1.056입니다. 굴절률은 1.4143입니다. 물에 약간 용해되며 에탄올, 에테르, 클로로포름 및 벤젠에 용해된다. 에틸 말로 네이트는 산과 알칼리의 반응에서 말 론산과 에탄올을 생산합니다.
용도
그것은 주로 고급 유기 합성에 사용되며 제조 아세트산을 대체합니다. 제약 산업에서 chloroquine, phenylbutazonein, barbital 및 기타 의약품을 합성합니다. 게다가, 그것은 또한 살충제, 페인트, 향신료 및 기타 산업에서 사용할 수 있습니다.
개요
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.
화학적 성질
Diethyl malonate has a faint, pleasant, aromatic odor.
출처
Reported found in pineapple, bilberry, Cape gooseberry, cognac, malt whiskey, apple brandy, grape brandy,
port, cider, sherry and red, white, strawberry and bilberry wines.
용도
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.
제조 방법
Reacting chloroacetic acid to cyanoacetic acid using sodium cyanide and subsequent saponification; malonic acid is
finally esterified by azeotropic distillation with ethanol in benzene
일반 설명
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.
Safety Profile
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.
신진 대사
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).
Purification Methods
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.]
말론산 디에틸 준비 용품 및 원자재
원자재
준비 용품
5-Nitropyridine-2-carboxylic acid
5-CARBETHOXYURACIL
페닐부타존
3-CARBETHOXYUMBELIFERONE
5,7-BIS(TRIFLUOROMETHYL)-4-HYDROXYQUINOLINE
2-(TRIFLUOROMETHYL)-4-HYDROXYPYRIMIDINE-5-CARBOXYLIC ACID
엔옥사신
2-ETHOXY-MALONIC ACID DIETHYL ESTER
5-NITROBENZOFURAN-2-CARBOXYLIC ACID
3-CARBETHOXY-2-PIPERIDONE
2,4-Dihydroxypyrimidine-5-carboxylic acid
2-AMINODIETHYLMALONATE
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-Chloro-7-(trifluoromethyl)quinoline
Diethyl butylmalonate
5,7-BIS(TRIFLUOROMETHYL)-4-CHLOROQUINOLINE
2-Benzofurancarboxylic acid ethyl ester
ETHYL 2-(ETHYLTHIO)-4-HYDROXYPYRIMIDINE-5-CARBOXYLATE
글리클라지드
4-Chloro-6-methoxy-2-(methylthio)pyrimidine
ETHYL 7-METHOXYBENZOFURAN-2-CARBOXYLATE
4-CHLORO-2-METHANESULFONYL-6-METHOXY-PYRIMIDINE
Ethoxylated
DIETHYL 2-(2-CYANOETHYL)MALONATE
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
Diethyl chloromalonate
TRIETHYL 1,1,2-ETHANETRICARBOXYLATE
4,6-Dihydroxy-2-methylpyrimidine
설파모노메타진
헥실데카논산
시클로펜틸아세트산
5,7-BIS(TRIFLUOROMETHYL)-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID
