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ChemicalBook CAS DataBase List 1,2-Dimethylimidazole
1739-84-0

1,2-Dimethylimidazole synthesis

10synthesis methods
1,2-Ethenediylbis(oxy) (9CI)

131543-46-9

Acetaldehyde

75-07-0

Methylamine

74-89-5

1-Methylimidazole

616-47-7

1,2-Dimethylimidazole

1739-84-0

2-Methylimidazole

693-98-1

A high-pressure microreactor equipped with three micro-mixers was used for the synthesis. It was operated as follows: an aqueous methylamine solution (0.33 mol/L) was fed from tank 1 via pump 1 at a flow rate of 0.68 mL/min; an aqueous acetaldehyde solution (0.33 mol/L) was fed from tank 3 via pump 3A at a flow rate of 63 mL/min while nearby water (0.33 mol/L) flowed at a flow rate of 1.13 mL/min; an aqueous glyoxal solution ( 0.33 mol/L) was fed from tank 4 via pump 4 at a flow rate of 0.56 mL/min. The reaction pressure was set to 30 MPa and the final flow rate was 8.0 mL/min. The temperature of the first micro-mixer and the 2.4 m reaction tube was controlled at 25 °C by the thermostat chamber 1 , under which the mixing and reaction of methylamine with acetaldehyde was carried out. Subsequently, in the second micro-mixer, the reaction mixture was mixed with ammonia and kept at 25 °C in the constant temperature chamber 2, and the reaction was fully mixed and reacted in the 0.1 m reaction tube. Next, glyoxal was added to the reaction system and fully reacted in a 0 m reaction tube. Subsequently, the temperature of the reaction zone was raised to 70 °C and the reaction was continued in a 25 μm reaction tube. Finally, the reaction mixture was cooled to 5 °C by a heat exchanger, depressurized to atmospheric pressure by a pressure reducing valve, and the aqueous solution obtained under cooling in ice water (0 °C to 4 °C) was collected. The residence time of the reaction part was 37 seconds throughout the reaction. For analysis, the product was diluted 10-fold with ice water, if necessary, and analyzed immediately using a gas chromatograph. The reaction tube was made of stainless steel (SUS316) with an inner diameter of 0.5 mm. the yield of the product 1,2-dimethylimidazole was 85.1%. The quantitative analysis was performed on an Agilent gas chromatograph (GC 6890, hydrogen flame ionization detector) with an HP-INNOWAX column (inner diameter 0.32 mm, film thickness 0.25 μm, length 30 m) manufactured by J & W Co. The yield of each product (1,2-dimethylimidazole, 1-methylimidazole, 2-methylimidazole, and imidazole) was determined by preparing standard curves for each product. The yield of each product was calculated based on the concentration obtained by conversion of the standard curve as follows: 1,2-dimethylimidazole 85.1%, 1-methylimidazole 6.27%, 2-methylimidazole 6.59%, and imidazole 2.06%.

-

Yield:1739-84-0 85%

Reaction Conditions:

in N,N-dimethyl-formamide at 120 - 145;Solvent;Temperature;

Steps:

2 Example 2
To 500 ml of the input three-mouth flask in 128g of 2 - methyl imidazole and 100 ml of DMF, oil bath heated to 120 °C, the temperature next adds by drops 280g dimethyl carbonate, control temperature at 135 - 140 °C, dropping time control in 5 - 6h, after dropping in the 145 °C preserving 2h, thermal insulation after the completion of the, gas chromatographic analysis of 2 - methyl imidazole conversion 98%. In 4.0KPa, 90 °C conditions under reduced pressure distillation, evaporate the solvent. The use of the rectifying device, in 4.0KPa under vacuum, collecting 100 - 110 °C of distillate, high purity can be obtained of the 1, 2 - dimethyl imidazole of the finished product, yield 85%, gas chromatographic analysis of the content of 99.5%.

References:

Jiangsu Leisure New Material Technology Co., Ltd;Xia, Wei;Shen, Jian;Wang, Koojun;Yan, Yong CN106045912, 2016, A Location in patent:Paragraph 0020; 0021; 0023; 0024; 0025; 0026; 0027

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