1,1′-Dimethyl 2,2′-(1,2-diazenediyl)bis[2-methylpropanoate]

200 g of wet 2, 2'-hydrazobisisobutyronitrile (1 mol) are added to 750 g of chlorobenzene while heating at approximately 30 C. to obtain dissolution of the hydrazobisisobutyronitrile. The upper aqueous phase, i.e. 30 g, is separated by settling. The water dissolved in the chlorobenzene is removed by azeotropic entrainment under vacuum. 76.8 g of methanol (2.4 mol) and 0.2 g of sodium bromide are added. 74.6 g of chlorine (1.05 mol, which results in the in situ formation of 2.0 mol of HCl) are added while cooling at approximately 15 C., followed by 21.9 g of hydrochloric acid (0.6 mol). The reaction mixture is stirred for 18 hours at approximately 20 C. The mixture is subsequently run into 600 g of water over approximately 1 hour; the temperature is allowed to reach approximately 30 C. and then cooling is applied in order for the temperature not to exceed this value. The mixture is subsequently stirred at approximately 30 C. for 1 hour in order to obtain clear aqueous and organic phases. The chlorobenzene is removed by azeotropic entrainment under vacuum at a temperature of 35 C. The upper organic phase is separated by settling. The azoester yield thus obtained is 92percent.General procedure: Hydrazodicarboxamide (1.0 mmol), cerium (III) ammonium nitrate tetrahydrate (0.1 mmol) was added to a glass test tube (15 ml) equipped with a screw, And acetic acid (2 mL) were added, and the system was closed by installing a rubber balloon filled with air at atmospheric pressure.After stirring at room temperature for 12 hours, the resultant product was filtered, Washed with water to obtain yellow crystals. By high-performance liquid chromatography analysis using an internal standard substance, azodicarboxamide was produced at a yield of 88percent. Separately, this yield was confirmed also by a method in which potassium iodide was allowed to act on the aqueous dispersion of this material and titrated with sodium thiosulfate as the released iodine.;When oxidation reaction, post-treatment and analysis were carried out in the same manner as in except that cupric bromide (0.1 mmol) was newly added as a raw material in Example 1, Azodicarboxamide was produced at a yield of 99percentIn a 500 ml three-necked flask with a stirring and reflux device, 41.8 g of 98% 2, 2?-azobisisobutyronitrile (0.25 mol) and 200 g of dichloroethanePut 33.6 g of 99.9% methanol (1.05 mol), start stirring, Start cooling to 15 deg.] C was slowly added dropwise 66.1 g of 99% thionyl chloride (0.55mol), The dropping rate of sulfoxide was 16 g / hour.Then the temperature of the material was controlled at 32 C, and the temperature was maintained for 6 hours.After the reaction was completed, 104.5 g of cold water at 7 C was added dropwise to carry out the hydrolysis reaction.After 1 hour of reaction, the layers were separated. The organic phase is washed with an appropriate amount of water and separated into layers.The organic phase is distilled under reduced pressure until all dichloroethane is recovered by distillation.This gave liquid dimethyl azobisisobutyrate. Dimethyl azobis isobutyrate liquid cryogenic cooling to obtain a white solid product dimethyl azobis isobutyrate.The yield (based on 2, 2'-azobisisobutyronitrile) was 94.9%. Product content (HPLC) 99.8%.A method for preparing azobisisobutyrate, the preparation method mainly comprises the following steps:The azobisisobutyronitrile, methanol, toluene, strong acid cation exchange resin was added to the reactor;Among them, the amount of methanol is 2.05 times the molar amount of azobisisobutyronitrile; and the amount of strongly acidic cation exchange resin is 5% of the mass of azobisisobutyronitrile. After stirring for 10 hours at 30 C, the strongly acidic cation exchange resin was removed by filtration; the filtrate was concentrated and the solvent was removed by distillation under reduced pressure to give the product dimethyl azobisisobutyrate.In a 500 ml three-necked flask equipped with a stirring and refluxing apparatus, 41.8 g of 98% 2, 2'-azobisisobutyronitrile (0.25 mol) and 200 g of toluene were charged, and 17.6 g of 99.9% methanol (0.55 mol) was charged. The stirring was turned on, and 20.3 g of 99% hydrogen chloride gas (0.55 mol) was slowly introduced into the cooling at 15 C, wherein the hydrogen chloride gas introduction rate was 40 g / hr. Then, the temperature of the material was controlled at 20 C and held for 38 hours. After the completion of the reaction, the reaction solution was dropped into water at a rate of 100 g/hr to carry out a hydrolysis reaction for 1 hour, and after the completion of the hydrolysis, the layers were separated, and 22 g of methanol was added to the organic phase, and the mixture was distilled under reduced pressure for 4 hours, and the distillation pressure under reduced pressure was -0.01 MPa. After the end of the distillation, the organic phase was added dropwise to a mixed solution of 30.6 g of a 30% sodium methoxide solution (sodium methoxide 0.17 mol) and 32.7 g of 98% monoethanolamine (0.525 mol) at 100 g/hr, and kept at a temperature of 40 C for 3 hours. After the end of the heat preservation, the solid liquid is separated by a centrifuge, the solid is further washed with water, crystallized to a dryness, and the material is placed in a desiccator for drying. After drying, the material is cooled to room temperature to obtain 2, 2'-azobis(2-methyl-N-(2-hydroxyethyl)propionamide) product, The yield (calculated as 2, 2'-azobisisobutyronitrile) was 74.9%, Product content (HPLC) 99.5%.

Molecular Weight:230.26
XLogP3:1.6
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:6
Exact Mass:230.12665706
Monoisotopic Mass:230.12665706
Topological Polar Surface Area:77.3
Heavy Atom Count:16
Complexity:278
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes