Diethyl Malonate CAS 105-53-3

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  • Appearance: Colorless liquid
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: Diethyl Malonate Supplement
105-53-3

Basic Info of Diethyl Malonate

What is Diethyl Malonate?

Malonate is a very beneficial reagent in natural synthesis, which can hydrolyze as well as decarboxylate. At the same time, methylene is very easy to develop carbon anion and acylation, alkylation, aldehyde alcohol reaction as well as Michael response happen.

As a natural substance, diethyl malonate belongs to diethyl malonate, which normally exists in guava fruits, melons, grapes, pineapples, blackberries and also strawberries. It is an anemic fluid with apple flavor. Because of its all-natural and pleasurable smell, it is a taste ingredient generally discovered in perfume, synthetic flavors, alcohols, numerous red wines and spirits. It is likewise used as an essential intermediate for the synthesis of lots of drugs, such as barbiturates, vitamins B1 as well as B6, as well as non steroidal anti-inflammatory representatives. On top of that, diethyl malonate is likewise associated with the organic synthesis of various other compounds, such as α- Aryl malonate, monosubstituted and disubstituted acetic acid. In Knoevenagel condensation response with benzaldehyde, diethyl benzylidene malonate was formed.

Malonic acid and its by-products are commonly made use of in pharmaceutical, spices, food additives, polyester and also various other sectors. They are essential fine chemical resources and also intermediates. Particularly in pharmaceutical intermediates, diethyl malonate is widely used in the synthesis of barbituric acid, amino acids, vitamins B1, B2 as well as B6, sleeping medications, phenylbutazone and also various other medicines.

Diethyl Malonate Uses

  1. Diethyl malonate is an important great chemical raw material. Since the methylene hydrogen in its molecule is easily changed by a variety of teams, and then generates a range of vital by-products, it is extensively used in various chemical production. Fields, consisting of food, medication, chemicals, industrial dyes, liquid crystal materials and other sectors.
  2. GB 2760-96 states that the edible flavors are allowed to be utilized. Generally used for the preparation of pear, apple, grape, cherry and other fruit tastes.
  3. Diethyl malonate is a crucial intermediate in the preparation of 2-amino-4,6-dimethoxypyrimidine as well as can be used in the prep work of sulfonylurea herbicides, such as bensulfuron, pyrazosulfuron, nicosulfuron It is likewise an intermediate for sulfa drugs and barbiturates in medicine.
  4. Diethyl malonate is an intermediate in organic synthesis. Widely used in the production of dyes, fragrances, sulfonylurea herbicides, and so on. Diethyl malonate is primarily utilized to produce ethoxymethylidene, barbituric acid, diethyl alkyl malonate, and after that to manufacture medicines such as norfloxa Star, romefloxacin, chloroquine, phenylbutazone, and so on and synthetic dyes and pigments such as benzimidazolone natural pigments. Diethyl malonate abroad is primarily made use of to create ethoxymethylidene, barbituric acid and also diethyl malonate alkylate.
  5. Check for ammonia and potassium. Gas chromatography fixed service (maximum operating temperature is 40 ° C, solvent is benzene, chloroform, ethanol). Solvent, plasticizer for materials and also nitrocellulose. Organic Synthesis.

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Preparation of Diethyl Malonate

  • The oxoesterification reaction was carried out in a 25 ml stainless steel autoclave lined with a glass sleeve. (Cp*RhCI) of 2.1 × 10-2mmol, 0.2ml (1.87mmol) ClCH COOC H , 0.27ml (1.94mmol) Et N, 0.12ml (2.0mmol) EtOH, 20mg (0.12mmol) KI, 5ml toluene are added to the reactor , mix well. Tighten the lid of the kettle, charge the kettle with 1.0MPa carbon monoxide for 5 times, and then charge the kettle with 2.0MPa carbon monoxide. The reaction kettle was placed in a constant temperature oil bath to react at 115°C with electromagnetic stirring. After reacting for 48 hours, the reaction kettle was taken out and cooled to room temperature naturally. The product was analyzed by gas chromatography and the reaction results were as follows: the conversion rate was 96.5%, the selection rate was 76.6%, and the yield was 73.9%.

  • In a stainless steel autoclave, add ethyl chloroacetate (1mol), magnetic silica gel-supported cobalt metal complex acetate (5g), ammonia water (1.1mol), ethanol (2mol), mix well, and replace the air in the autoclave with carbon monoxide 4 times, and then charged with carbon monoxide to maintain the pressure at 1.0 MPa, heated to 60 °C, and stirred for 2 hours. The product was separated by cooling and filtration and the catalyst was recovered, and the filtrate was rectified to obtain the product diethyl malonate with a yield of 82%. The results of GC-MS analysis showed that the purity of diethyl malonate was 96.8%.

The Purification Method of Diethyl Malonate

In a 250ml four-necked flask, add 80g (93.5%) of diethyl malonate with an impurity content of 0.51%, 144.0g of n-hexane [diethyl malonate: n-hexane=1: 1.8 (w/w)], activated carbon 4g, heated to 30°C. After filtration, the filtrate was cooled to -10~-5°C, and a large amount of white solid was precipitated, stirred for 45 minutes, and filtered to obtain 77 g of crude product. The solvent was evaporated under reduced pressure at 60°C/0.8MPa to obtain 71.6 g of a colorless transparent liquid with a purity of 97.3%, an impurity content of 0.092% and a solvent residue of less than 0.1%. Yield 93.1%.

In a 250ml four-necked beaker, add 70 g (97.3%) of diethyl malonate with an impurity content of 0.092% and 126.0 g of n-hexane [diethyl malonate: n-hexane = 1: 1.8 (w/w)], heat up to 30°C and stirred for 30 minutes. It was cooled to -10°C to -5°C, a large amount of white solid was precipitated, stirred for 30 minutes, and filtered to obtain 74 g of crude product. The solvent was evaporated under reduced pressure at 80°C/0.8MPa to obtain 67 g of a colorless transparent liquid with a purity of 99.6%, an impurity content of 0.03% and a solvent residue of less than 0.1%. Yield 98.0%.

Reference

  1. Diethyl malonate – PubChem
  2. Lu Yalin, & Song Weihong. (2004). Catalyzed carbonylation for synthesis of diethyl malonates. Journal of Nanjing University of Science and Technology (Natural Science Edition)

Quality Control of Diethyl Malonate

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