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Synthetic method for N, N-disubstituted-2-hydroxyl aliphatic amide compound

A technology for amide compounds and synthesis methods, which is applied in the preparation of organic compounds, chemical instruments and methods, preparation of carboxylic acid amides, etc., can solve the problems of difficulty in microwaves, affect the reaction effect and yield, etc., and achieves short reaction routes and raw materials. Simple, high-yield effects

Inactive Publication Date: 2013-12-11
浙江交通科技股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in a large reactor, limited by the penetration rate of microwave radiation, it is difficult for microwaves to radiate evenly into the reactor, which seriously affects the effect and yield of the reaction.

Method used

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  • Synthetic method for N, N-disubstituted-2-hydroxyl aliphatic amide compound
  • Synthetic method for N, N-disubstituted-2-hydroxyl aliphatic amide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Dissolve 0.2mol glycolic acid in 150mL methanol, and 0.25mol dimethylamine gas in 50mL methanol, pour the two solutions into a high-pressure batch reactor, and then feed N into the autoclave. 2 , the pressure is 2.4MPa. The reaction was carried out for 6 hours at a rotation speed of 900 rpm and a temperature of 150°C. After the reaction, wait for the temperature in the kettle to drop to room temperature, and distill under reduced pressure to obtain 3.68 g of N,N dimethylglycolamide red solution with a purity of 84.4% and a yield of 15.1%. Characterization data of the purified product: melting point 44°C; 1 H NMR (CDCl 3 )δ=2.81(s,3H),2.94(s,3H),3.48(s,1H,OH),4.05(s,2H); MS(EI):103[M] + .

Embodiment 2

[0029] Dissolve 0.213mol of glycolic acid in 150mL of methanol, and 0.681mol of dimethylamine gas in 50mL of methanol, pour the two solutions into a high-pressure batch reactor, and add Al 2 o 3 powder, and N into the autoclave 2 , the pressure is 2.4MPa. The reaction was carried out for 6 hours at a rotation speed of 900 rpm and a temperature of 150°C. After the reaction was completed, wait until the temperature in the kettle dropped to room temperature, open the kettle and distill the obtained solution under reduced pressure to obtain 12.369 g of white crystals of N,N-dimethylglycolamide with a purity of 96.5% and a yield of 57.42%.

Embodiment 3

[0031] Dissolve 0.214mol of glycolic acid in 150mL of methanol, 0.854mol of dimethylamine gas in 50mL of methanol, pour the two solutions into a high-pressure batch reactor, and add 3% of the molar amount of glycolic acid MoO 3 , and then N into the autoclave 2 , the pressure is 2.4MPa. The reaction was carried out for 5 hours at a rotation speed of 900 rpm and a temperature of 150°C. After the reaction was completed, wait until the temperature in the kettle dropped to room temperature, open the kettle and distill the obtained solution under reduced pressure to obtain 13.235 g of white crystals of N,N-dimethylglycolamide with a purity of 99.4% and a yield of 59.6%.

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PUM

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Abstract

The invention discloses a synthetic method for an N,N-disubstituted-2-hydroxyl aliphatic amide compound. The synthetic method is carried out according to the following steps of (1) adding 2-hydroxyl aliphatic acid shown as a formula (I), an aliphatic acid secondary amine compound shown as a formula (II), a catalyst and a solvent in an autoclave reactor and mixing uniformly, wherein the catalyst is one or any combination selected from Al2O3, SiO2, TiO2, SnO2, SnO, P2O5, ZnO, MgO, Bi2O3, MoO3, CeO2, WO3 and La2O3; (2) introducing nitrogen to the autoclave reactor, controlling a pressure at 0.2-12 MPa, then reacting for 3-24 hours at a temperature of 0-300 DEG C and a rotation speed of 10-1,500 revolutions / min; and (3) distilling an obtained solution after the reaction is finished to obtain the N,N-disubstituted-2-hydroxyl aliphatic amide compound. In the synthetic method, tedious steps such as protection and deprotection of the hydroxyl which are reported in literatures are prevented, so that synthetic route is greatly simplified and the synthetic method has great industrial production value.

Description

(1) Technical field [0001] The invention relates to a synthesis method for preparing N,N-disubstituted-2-hydroxy aliphatic amide compounds in one step by using 2-hydroxy fatty acid and aliphatic secondary amine compounds as raw materials. (2) Background technology [0002] Low-level aliphatic hydroxyl-substituted amide compounds are solvents with good performance and good solubility for resins. They are mainly used as solvents for heat-resistant synthetic fibers and plastic films, and gradually become new cleaning agents for LCD liquid crystal displays and semiconductor materials. Has broad market prospects. [0003] At present, the hydroxy-substituted amides have not been produced on an industrial scale in the world. The main reason is that when hydroxycarboxylic acid and amine compound react, various side reactions are prone to occur. For example, the oxidation of amines in the reaction makes the product have an undesired color, and the decarboxylation reaction of carbox...

Claims

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Application Information

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IPC IPC(8): C07C235/06C07C231/02
Inventor 许孝良吾石华黄金宁李小年毛正余
Owner 浙江交通科技股份有限公司
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