Synthesis method of trinitroethyl carbamate

A technology of trinitroethyl carbamate and synthesis method, which is applied to the preparation of carbamic acid derivatives, chemical instruments and methods, and the preparation of organic compounds, and can solve the problems of inconvenient use, unstable carbamoyl chloride, and unsuitable TNC scale-up synthesis and other problems, to achieve the effect of fast reaction rate, easy scale-up synthesis, and short synthesis route

Inactive Publication Date: 2015-05-06
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The great defect of these three kinds of methods is that all need to use phosgene directly or indirectly, the carbamoyl chloride that needs to use in method one and method two and the preparation process of ethyl thiochloroformate all use phosgene as reaction reagent, but phosgene is Highly toxic gas, very inconvenient to use, in addition, carbamoyl chloride is very unstable, therefore, these methods are not suitable for the scale-up synthesis of TNC

Method used

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  • Synthesis method of trinitroethyl carbamate
  • Synthesis method of trinitroethyl carbamate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Dissolve trinitroethanol (5.4318g, 0.03mol) in dichloromethane (20mL) in a 100mL three-neck flask equipped with a thermometer and magnetic stirring, and add chlorosulfonyl isocyanate (5.4 mL, 0.06mol), stirred and reacted at this temperature for 1h, removed the ice-water bath and returned to room temperature for reaction, TLC monitored the reaction, and the reaction of the raw materials was complete in about 2h, added 25mL of water dropwise to the reaction mixture and heated and stirred until no bubbles were generated, ethyl acetate After extraction, the combined organic phases were dried and concentrated to obtain 6.5861 g of white solid with a yield of 98.1%. Decomposition temperature: 1 H NMR (300MHz, [D 6 ]acetone): δ=6.78,6.49,5.70ppm; 13 C NMR (100MHz, [D 6 ]acetone): δ=154.31, 125.53, 61.60ppm; IR (KBrpellet): 3454, 3354, 3304, 3003, 2963, 2917, 1735, 1591, 1443, 1401, 1368, 1328, 1302, 1250, 1169, 1107, 1026,910,875,857,805,784,772,743,538.2cm -1 , elementa...

Embodiment 2

[0019] Dissolve trinitroethanol (5.4315g, 0.030mol) in dichloromethane (20mL) in a 100mL three-neck flask equipped with a thermometer and magnetic stirring, and add trichloroacetyl isocyanate (3.9 mL, 0.033mol), stirred and reacted at this temperature for 1h, removed the ice-water bath and returned to room temperature for reaction, TLC monitored the reaction, and the raw materials were completely reacted in about 3h, added 25mL water dropwise to the reaction mixture and heated and stirred until no bubbles were generated, ethyl acetate After extraction, the combined organic phases were dried and concentrated to obtain 6.3782 g of white solid with a yield of 95.0%.

Embodiment 3

[0021] Dissolve trinitroethanol (5.4312g, 0.03mol) in chloroform (20mL) in a 100mL three-necked flask equipped with a thermometer and magnetic stirring, cool to 0°C with an ice-water bath, and then add chlorosulfonyl isocyanate (5.4 mL, 0.06mol), stirred and reacted at this temperature for 0.5h, removed the ice-water bath and returned to room temperature for reaction, TLC monitored the reaction, and after 1.5h, the raw materials were completely reacted, and 25mL of water was added dropwise to the reaction mixture and heated and stirred until no bubbles were generated. Extracted with ethyl ester, combined organic phases were dried and concentrated to obtain 6.4517 g of white solid with a yield of 94.8%.

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Abstract

The invention belongs to a synthesis method of trinitroethyl carbamate. The trinitroethyl carbamate is obtained through one-step method by hydrolyzing reacted trinitroethanol and a carbamated reagent isocyanate derivative react and the reaction product is hydrolyzed in a one-step method to obtain trinitroethyl carbamate. The preparation method of the trinitroethyl carbamate has the characteristics of being short in reaction path, high in reaction speed, mild in reaction condition, and high in reaction yield, the method can be put into applification synthesis and industrial production easily.

Description

technical field [0001] The invention relates to a synthesis method of trinitroethyl carbamate, which belongs to the technical field of energetic materials. Background technique [0002] For a long time, ammonium perchlorate (AP) has been the first choice of solid rocket propellant oxidant, but the perchlorate of AP will pollute the groundwater, which will affect the function of the thyroid gland at high concentrations, and the HCl gas released by the combustion of AP will form acid rain and destroy Therefore, researchers from various countries have been working on developing new halogen-free oxidants to replace AP. Multi-nitro energetic compounds have very important uses in the field of energetic materials. Trinitromethyl, that is, nitroform functional groups, are important structural fragments for building multi-nitro energetic compounds. The introduction of nitroform functional groups into energetic compounds can Significantly increased density and increased oxygen conten...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/02C07C271/12
Inventor 黄海丰李营蔺向阳潘仁明杨军
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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