Method for preparing amide by metallic sodium catalyzed ester ammonolysis reaction

A technology for catalyzing ester and ammoniation reactions with sodium metal, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylic acid amides, etc., can solve the problems of difficult wastewater treatment, highly toxic sodium cyanide, etc. , easy separation, high conversion rate

Inactive Publication Date: 2017-07-07
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, sodium cyanide is highly toxic and difficult to treat wastewater

Method used

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  • Method for preparing amide by metallic sodium catalyzed ester ammonolysis reaction
  • Method for preparing amide by metallic sodium catalyzed ester ammonolysis reaction
  • Method for preparing amide by metallic sodium catalyzed ester ammonolysis reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1, take ethyl acetate (44g) and liquefied ammonia (34g) as reaction raw material, metal sodium (0.69g) is catalyst, add 200mL belt stirring autoclave, no longer drop as reaction end point with reaction pressure, reaction time and The reaction results are shown in Table 1 below:

[0047] Table 1. Metal sodium catalyzed ester amination reaction

[0048]

[0049] When the reaction temperature is 90°C, the maximum pressure (that is, the initial pressure value) is 2.0MPa; when the reaction temperature is 70°C, the maximum pressure is 1.6Mpa; when the reaction temperature is 115°C, the maximum pressure is 3.1 Mpa; when the reaction temperature is 130°C, the maximum pressure is 4.0MPa.

[0050] From Table 1, we know that: when the reaction time of the reaction decreases as the temperature increases, the yield increases as the temperature increases. Moreover, when the reaction temperature reaches above 90° C., the reaction conversion rate reaches above 97%, and ...

Embodiment 2

[0054] Example 2, with ethyl acetate (44g) and liquid ammonia (quantitative) as the reaction raw materials, metal sodium (0.69g) as the catalyst, add 200mL agitated autoclave, with the reaction pressure no longer falling as the reaction end point, explore liquid ammonia Effect of dosage on response. Reaction time and reaction result are as shown in table 2 below:

[0055] Table 2. Effect of feeding ratio on reaction

[0056]

[0057] When the reaction liquid ammonia feed ratio is 2.0, continuing to increase the liquid ammonia feed has no obvious change in the reaction, and will lead to an increase in the reaction pressure. In Example 2, the initial pressure values ​​corresponding to No. 1, No. 2, and No. 3 are 0.7 MPa, 2.0 MPa, and 3.5 MPa, respectively.

[0058] Subsequent treatment after the reaction is equal to Example 1.

Embodiment 3

[0059] Example 3, with ethyl acetate (44g) and liquefied ammonia (34g) as reaction raw materials, metal sodium (quantitative) as catalyst, add 200mL belt stirring autoclave, take reaction pressure no longer to drop as reaction end point, explore reaction catalyst consumption effect on the response. Reaction time and reaction result are as shown in table 3 below:

[0060] Table 3, reaction temperature influence on reaction

[0061]

[0062] From table 4, it can be found that the catalyst consumption increases, and the reaction speed is greatly improved. When the catalyst consumption reaches 6% of the raw material ester consumption, the 6hr reaction conversion rate reaches 98%. If the catalyst consumption continues to increase, the reaction speed will still be increased. faster, but the conversion rate remains the same.

[0063] In this embodiment 3, the initial reaction pressure is 2.0Mpa. Subsequent treatment after the reaction is equal to Example 1.

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Abstract

The invention discloses a method for preparing amides by metallic sodium-catalyzed ester amination reaction: the reaction is carried out in an autoclave at 90-140°C with ester and liquid ammonia as raw materials and metallic sodium as a catalyst, ester:ammonia=1:1.2 The molar ratio of ~5.0, metal sodium is 4~10% of the molar weight of the ester; when the reaction pressure no longer drops, the reaction is stopped, the unreacted ammonia is recovered, and the obtained reaction product is post-processed to obtain the product. The method can efficiently prepare amides; and the raw materials are cheap, low in toxicity, high in reactivity, less in catalyst consumption, fast in reaction speed, high in reaction conversion rate, and easy to separate products.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing amides, a class of chemical intermediates, and belongs to the field of organic synthesis. Background technique [0002] Amides refer to a class of important organic compounds containing amide bonds (-CONR(H)-), which can be widely used as industrial solvents, detergents, plasticizers, lubricants, lubricants, and intermediates as organic synthesis products. The body further undergoes reactions such as protection of amino groups, dehydration to nitriles, and Hofmann degradation to amines. In biology or medicine, an amide bond, also called a peptide bond, is a bridge that links amino acids into proteins. [0003] At present, the traditional methods for preparing amides in industry mainly include dehydration of ammonium carboxylate, ammoniation of acid chloride, acid anhydride, ester, partial hydrolysis of nitrile, and direct ammoniation of car...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C233/05C07C233/65C07C233/11
CPCC07C231/02C07C233/05C07C233/65C07C233/11
Inventor 钱超欧阳博陈新志
Owner ZHEJIANG UNIV
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