Method for synthesizing N,N-dialkyl oxamide by using CO2

A technology of dialkyl oxamide and dialkyl urea, which is applied in the field of synthesizing N-alkyl oxamide, and achieves a considerable yield

Active Publication Date: 2015-05-13
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] But so far, there is no public CO at home and abroad 2 As a carbonylation reagen

Method used

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  • Method for synthesizing N,N-dialkyl oxamide by using CO2

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] A use of CO 2 Preparation of N, the production method of N'-dibutyloxamide:

[0029] Take 10ml (0.103mol) of n-butylamine and put it into a stainless steel autoclave with 50ml of polytetrafluoroethylene lining and magnetic stirring, then add catalyst lanthanum tartrate 1.4g (0.005mol) and cocatalyst molecular sieve dehydrating agent 3g, organic solvent 1,3-Dimethyl-2-imidazolinone (DMI) 20ml, at room temperature, filled with 2.5MPa of CO 2 , seal the reaction vessel, raise the temperature to 150°C, and react at constant temperature for 24h. Cool, vent to normal pressure and normal temperature, take out the light yellow reaction liquid, filter the catalyst and dehydrating agent, and then distill off the inert solvent DMI under reduced pressure at about -0.096MPa and 180°C to obtain N,N'-dibutyl oxalamide, The vacuum distillation product was subjected to gas chromatography-mass spectrometry analysis, and the conversion rate of raw material n-butylamine was measured to b...

Embodiment 2

[0034] A use of CO 2 preparation N, N'- The production method of dihexyl oxalamide:

[0035] The operation is the same as in Example 1, and the solvent is the same as in Example 1. The organic amine n-butylamine is replaced by n-hexylamine, and the catalyst lanthanum tartrate is replaced by yttrium oxalate. When other conditions remain unchanged, the reaction temperature is 180 ° C, and the reaction time is 40 hours. The product N,N'-dihexyloxamide. The conversion rate of raw material n-hexylamine was measured to be 87%.

[0036] Product composition, selectivity and yield are shown in Table 2:

[0037] Table 2. Product composition, selectivity and yield

[0038] product composition Selectivity (%) Yield (%) N,N'-Dihexyloxamide 82.5 71.8 N,N'-Dihexylurea 16.3 14.2 Hexyl isocyanate 1.2 1.0

Embodiment 3

[0040] A use of CO 2 preparation N, N'- The production method of xylyl oxamide:

[0041] The operation is the same as in Example 1, the organic solvent DMI is replaced by diethylene glycol dimethyl ether (DME), n-butylamine is replaced by toluidine, the catalyst lanthanum tartrate is replaced by yttrium citrate, and the reaction temperature is At 180°C, the reaction time was 36 hours, and the product N,N'-xylyloxamide was obtained. The conversion rate of raw material toluidine is measured to be 40%.

[0042] Product composition, selectivity and yield are shown in Table 3:

[0043] Table 3. Product composition, selectivity and yield

[0044] product composition Selectivity (%) Yield (%) N,N'-xylyl oxamide 31.2 12.5 N,N'-Xylylurea 67.3 26.9 Tolyl isocyanate 1.5 0.6

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Abstract

The invention provides a method for synthesizing N,N-dialkyl oxamide by using CO2. According to the method, in an organic or inorganic solvent, one-step synthetic reaction is performed on the CO2 and organic amine to synthesize the N,N-dialkyl oxamide, with N,N-dialkyl urea and water as byproducts, in the presence of a certain catalyst and under a certain reaction condition that the reaction pressure is 10-80atm and the reaction temperature is 100-200 DEG C. The invention discloses the method for synthesizing the N,N-dialkyl oxamide by using the CO2. According to the method, a valuable and toxic metal catalyst and a toxic and explosive gas in the prior art are not used, and reactants, products, and added components in a system are safe and environment-friendly; the yield is considerable; technically, an improvement room exists; a safe and environment-friendly new method is provided for preparing the N,N-dialkyl oxamide.

Description

technical field [0001] The present invention relates to the method for synthesizing N-alkyloxamide, especially a kind of utilization CO 2 Process for preparing N,N-dialkyloxalamides. Background technique [0002] N, N-dialkyloxamides are important raw materials and synthetic intermediates for the preparation of α-amino acids, α-hydroxy acids, heterocyclic compounds, anticancer drugs and AIDS (HIV) antiviral drugs. It has broad application prospects in fine chemical industry and pharmaceutical synthesis. However, the current general preparation method is to use palladium series noble metals, such as palladium-phosphine complexes, PdCl 2 (PMePh 2 ) 2 , PdCl 2 (PEt 3 ) 2 , PdCl 2 [Ph 2 P(CH 2 ) 2 PPh 2 ], CuBr(PPh 3 ) 2 Under the catalysis of CO, alkyl halides and organic amines, it is synthesized in one pot. Based on the existence of the above synthetic route, such as the high toxicity of the raw material halogenated hydrocarbons and palladium series noble...

Claims

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Application Information

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IPC IPC(8): C07C233/56C07C231/00
Inventor 孙大雷方岩雄
Owner GUANGDONG UNIV OF TECH
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