Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing N, N, N-tripivaloyl-1, 3, 5-benzenetriamine

A technology of tripivaloyl and triaminobenzene, which is applied in chemical instruments and methods, preparation of carboxylic acid amides, preparation of amino compounds, etc., can solve the problems of low N-acylation reaction yield, high synthesis cost and difficult synthesis and other problems, to achieve the effect of compressing costs, improving atomic economic benefits and low prices

Pending Publication Date: 2022-01-28
BEIJING INSTITUTE OF TECHNOLOGYGY
View PDF4 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, in the prior art, XT386 is mainly obtained by N-pivaloylation of 1,3,5-triaminobenzene, and the difficulty of synthesizing 1,3,5-triaminobenzene leads to high synthesis cost
Therefore, based on the relatively difficult synthesis of 1,3,5-triaminobenzene and the low yield of its N-acylation reaction, those skilled in the art urgently need a simple, efficient, safe, low-pollution and low-pollution Cost-effective method to prepare N,N,N-tripivaloyl-1,3,5-triaminobenzene (trade name: XT-386)

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing N, N, N-tripivaloyl-1, 3, 5-benzenetriamine
  • Method for preparing N, N, N-tripivaloyl-1, 3, 5-benzenetriamine
  • Method for preparing N, N, N-tripivaloyl-1, 3, 5-benzenetriamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076]Step 1: Preparation of N,N,N-tripivaloyl-2,4,6-triaminotoluene represented by structural formula II. In this step, the reduction reaction and the in-situ acylation reaction are combined in the same system. details as follows:

[0077] Dissolve 2,4,6-trinitrotoluene (TNT, 3.4g, 0.015mol, 1eq) in a mixture of ethyl acetate (30ml) / pivalic anhydride (87ml, 0.45mol, 10eq) to obtain a TNT solution , put into Pd / C catalyst (0.3g) and triethylamine (64ml, 10eq), transfer to the high-pressure stirred reactor, vacuumize the high-pressure stirred reactor, fill with nitrogen, repeat several times, and finally vacuumize to ensure that there is no air residue , continue to feed hydrogen for high-pressure (0.6MPa) reduction reaction and in-situ N-acylation reaction at room temperature, the reaction lasts for 4 hours, and the reaction temperature is 30 ° C. After the reaction, a dark red solution and Pd / C catalyst are obtained.

[0078] The post-processing step is: after filtering out...

Embodiment 2

[0101] The implementation content of step 1 in this embodiment is similar to the implementation content of step 1 in the above-mentioned embodiment 1, the difference is that the mass ratio of Pd / C catalyst to TNT is 0.05:1, the pressure of hydrogen is 0.8MP, pivalic anhydride and TNT The molar ratio of the base is 5:1, the molar ratio of diisopropylethylamine to TNT is 5:1, the reaction solvent is methanol, the reduction reaction temperature is 15°C, the reduction reaction time is 0.5h, and the acylation reaction temperature is 5°C, the acylation reaction time was 0.5h, and the yield was 88%.

[0102] Step 2: Preparation of 1,3,5-tripivalamidobenzene.

[0103] Dissolve N,N,N-tripivaloyl-2,4,6-triaminotoluene (0.39g, 1.0mmol) and potassium dichromate (0.88g, 3.0mmol) in 5% aqueous dilute sulfuric acid (10ml) and tert-butanol (10ml), and put it on a magnetic stirrer to make it fully dispersed, and keep stirring on a magnetic stirrer at 90°C for 2 hours, until the red color of t...

Embodiment 3

[0107]The implementation content of step 1 in this embodiment is similar to the implementation content of step 1 in the above-mentioned embodiment 1, the difference is: the mass ratio of Pd / C catalyst to TNT is 0.1:1, the pressure of hydrogen is 0.1MP, pivalic anhydride and TNT The molar ratio of the base is 15:1, the base is pyridine and the molar ratio of TNT is 15:1, the reaction solvent is ethanol, the reduction reaction temperature is 30°C, the reduction reaction time is 5h, the acylation reaction temperature is 15°C, the acylation reaction time For 2h, the yield was 83%.

[0108] Step 2: Preparation of 1,3,5-tripivalamidobenzene:

[0109] Dissolve N,N,N-tripivaloyl-2,4,6-triaminotoluene (0.39g, 1.0mmol) and cobalt acetate (0.035g, 0.2mmol) in hexafluoroisopropanol (5ml), Add N-hydroxyphthalimide (1.4g) to the reaction solution, and charge 0.1MPa of O after getting rid of excess air. 2 . Raise the temperature to 60°C, react for 6 hours, discharge excess oxygen, re-rais...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Crystallization temperatureaaaaaaaaaa
Crystallization temperatureaaaaaaaaaa
Login to View More

Abstract

The invention provides a method for preparing N, N, N-tripivaloyl-1, 3, 5-benzenetriamine. The method comprises the following steps: step 1, taking 2, 4, 6-trinitrotoluene as a raw material, and reacting the 2, 4, 6-trinitrotoluene with hydrogen and pivaloyl anhydride in sequence to obtain N, N, N-tripivaloyl-2, 4, 6-triaminotoluene; and step 2, carrying out a demethylation reaction on the obtained N, N, N-tripivaloyl-2, 4, 6-triaminotoluene, so as to obtain the N, N, N-tripivaloyl-1, 3, 5-benzenetriamine. In the preparation method, decommissioned 2, 4, 6-trinitrotoluene is adopted, and used reactants or catalysts are common products in the chemical industry, so that the preparation method has the advantages of low cost and simple and easily available raw materials. In addition, the preparation method also has the characteristics of short synthesis steps, simple operation of each step, high yield, fast reaction rate, easy separation and collection of intermediate and final products and the like, and is beneficial to realization of mass production of N, N, N-tripivaloyl-1, 3, 5-benzenetriamine.

Description

technical field [0001] The invention relates to the fields of chemical industry and materials, and mainly relates to a method for preparing N,N,N-tripivaloylated-1,3,5-triaminobenzene. Background technique [0002] Polypropylene is a partially crystalline resin and is widely used in industry. Its mechanical properties, optical properties and heat resistance are closely related to its crystallinity and crystal morphology. During processing, unmodified polypropylene melts tend to form larger spherulites, which affect the performance of the final product. Adding a nucleating agent to the polypropylene processing formula can reduce the size of spherulites and improve product quality. [0003] N,N,N-tripivaloyl-1,3,5-triaminobenzene (trade name: XT-386) has been confirmed as an amide nucleating agent because of its stable and efficient characteristics. It has a good effect of inducing polypropylene nucleation, and can produce high-transparency polypropylene products at a lower...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C233/43C07C209/36C07C211/50C07C231/02C07C231/12
CPCC07C209/36C07C231/02C07C231/12C07C211/50C07C233/43Y02P20/52
Inventor 黄木华张志豪杨天宇付浩熹刘博瀚
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com