Diethyl malonate is an organic substance with the chemical formula C7H12O4. Colorless aromatic liquid; melting point -50°C, boiling point 199.3°C; relative density 1.0551 (20/4°C); insoluble in water, soluble in alcohols, ethers and other organic solvents.
Application of Diethyl malonate CAS#105-53-3
【Use I】 Used as intermediates of pharmaceutical weekly effect sulfonamide and barbitur, also intermediates of spices and dyes
【Use 2】 GB 2760 a 96 stipulates that it is allowed to be used as edible flavor. Mainly used in the preparation of pears, apples, grapes, cherries and other fruit-type flavors.
【Use 3】 Diethyl malonate is an important intermediate for the preparation of 2-amino-4,6-dimethoxypyrimidine, which can be used to prepare sulfonylurea herbicides, such as bensulfuron, pyrimethanesulfuron, nicosulfuron, etc. It is also used as an intermediate for sulfonamide and barbiturate in medicine.
【Use4】Diethyl malonate is an intermediate of organic synthesis. Diethyl malonate is widely used in the production of dyes, fragrances, sulfonylurea herbicides, etc. Diethyl malonate is mainly used to produce ethoxymethoxylate, barbiturate, diethyl alkylmalonate, which is then used to synthesize pharmaceuticals such as norfloxacin, romifloxacin, chloroquine, pautazone, etc. and synthetic dyes and pigments such as benzimidazolone organic pigments. Overseas diethyl malonate is mainly used to produce ethoxymethoxylate, barbiturate and diethyl malonate alkylates.
【Use 5】 To check ammonia and potassium. Gas chromatography stationary solution (maximum use temperature 40 ℃, the solvent is benzene, chloroform, ethanol). Used as a solvent for resin and nitrocellulose, plasticizer. Organic synthesis.
Chemical characteristics of Diethyl malonate
Ethyl ester can undergo nitration reaction and further reduce the principle to produce diethyl aminomalonate, which is an important intermediate in the synthesis of amino acids. It generates the commonly used sleeping drug barbiturate. Diethyl malonate is easily substituted by halogens to produce diethyl halogenated malonate; it can also be oxidized by dinitrogen trioxide to diethyl oxomalonate. Diethyl malonate can be made from sodium chloroacetate, which first interacts with sodium cyanide to form sodium cyanoacetate, and then is esterified with ethanol. Diethyl malonate is an important chemical material and organic synthesis reagent, widely used in the synthesis of drugs and dyes.
Related reactions of Diethyl malonate
The methylene group of diethyl malonate is influenced by two carbonyl groups and is highly reactive. It interacts with sodium ethanol to form sodium salts, which subsequently react with halogenated hydrocarbons to produce diethyl malonate substituted with mono- or dianionic hydrocarbon groups. They are all important intermediates in organic synthesis and can be further hydrolyzed and decarboxylated to form carboxylic acids, for example:
where R and R′ are hydrocarbon groups. Diethyl malonate can be nitrosated and further reduced to produce diethyl aminomalonate, which is an important intermediate for the synthesis of amino acids. Diethyl malonate is condensed with carbonyl compounds to produce the unsaturated compound RCH=C(COOC2H5)2. Hydrocarbon-substituted diethyl malonate is condensed with urea to produce barbiturates, which are commonly used as sleeping pills: diethyl malonate is readily substituted with halogens to produce diethyl halogenated malonate, which can also be oxidized by dinitrogen trioxide to oxomalonic acid ester O=C(COOC2H5)2. compounds are of theoretical and synthetic interest.
Diethyl malonate is produced from sodium chloroacetate by first interacting with sodium cyanide to produce sodium cyanoacetate and then esterifying it with ethanol. Diethyl malonate is an important chemical raw material and reagent for organic synthesis, widely used in the synthesis of drugs and dyes.
Production method of Diethyl malonate
Diethyl malonate is mainly produced by cyanide esterification and catalytic carbonylation methods, and the traditional cyanide esterification method is still commonly used in industry. It is obtained from chloroacetic acid by neutralization, cyanidation, hydrolysis and esterification. Chloroacetic acid is neutralized with sodium carbonate at 30°C to produce sodium chloroacetate, cyanidized with sodium cyanide at 92-95°C, and then hydrolyzed with alkali to produce sodium malonate. Sodium malonate is dried and esterified with ethanol at 70-72°C in the presence of sulfuric acid. The esterification product is washed and distilled to produce diethyl malonate. Raw material consumption quotas: chloroacetic acid (95%) 650kg/t, sodium cyanide (95%) 340kg/t, ethanol (95%) 910kg/t. The new process developed abroad is mainly based on catalytic carbonylation, i.e. the synthesis of diethyl malonate in one step reaction with chloroacetate, carbon monoxide and ethanol as raw materials and in the presence of catalyst. In contrast, the catalytic carbonylation method works in addition to the sodium cyanoacetate method, which is obtained by the direct esterification of cyanoacetic acid with ethanol.
Storage and transportation characteristics of Diethyl malonate
Packed in iron drums or galvanized iron drums, specification 200kg, stored and transported according to the regulations of combustible chemicals.
Conclusion
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