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

Method for preparing 4-methylbenzaldehyde from isoprene and acrolein

A technology of p-tolualdehyde and isoprene, which is applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve problems such as harsh reaction conditions, long process flow, and serious environmental pollution. Achieve the effects of mild reaction conditions, simple process operation, and wide source of raw materials

Active Publication Date: 2015-06-10
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
View PDF2 Cites 13 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Fast speed, long process flow, harsh reaction conditions, high content of oxidation by-products such as 4-carboxybenzaldehyde (4-CBA), and serious corrosion in the production process, requiring special materials such as titanium equipment, and large investment in equipment
In addition, p-xylene needs to be obtained from petroleum routes, which has serious environmental pollution

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 4-methylbenzaldehyde from isoprene and acrolein
  • Method for preparing 4-methylbenzaldehyde from isoprene and acrolein
  • Method for preparing 4-methylbenzaldehyde from isoprene and acrolein

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The preparation of graphite oxide adopts the following methods (Marcano, DC; Kosynkin, DV; Berlin, JM; Sinitskii, A.; Sun, ZZ; Slesarev, A.; Alemany, LB; Lu, W.; Tour, JMACS Nano2010, 4 ,4806): Add 3g graphite and 1.5g sodium nitrate to 69ml98% concentrated sulfuric acid under 0℃ ice bath, stir and mix well; then gradually add 9g potassium permanganate, keep stirring, keep the temperature below 20℃; Stir in a 35℃ water bath for 7 hours; continue to slowly add 12g potassium permanganate and stir for 12 hours; after the reaction is cooled, pour it into 400ml ice water and stir; add 3mL30% H2O2 and stir; then add 400mL30%HCl and stir At least 30min; Finally, the product is filtered and washed with deionized water until the pH value is about 7, and the product is vacuum dried to obtain graphite oxide.

Embodiment 2

[0029] Weigh a certain amount of metal halide and stir and dissolve it in 10 mmol ionic liquid 1-butyl-3-methylimidazolium chloride (BmimCl) at 120°C. After 10 minutes of reaction, the Lewis acidic ionic liquid can be prepared in different proportions. Diels-Alder reaction.

Embodiment 3

[0031] Add a certain amount of acrolein, isoprene and 10mmol BmimCl-ZnCl 2 (Mole ratio is 1:2) Put it into the flask, stir the reaction at different temperatures, after a certain period of time, sample and add about 1ml tetrahydrofuran to dilute, mix and centrifuge, and the product is qualitatively analyzed by GC-MS and quantitatively analyzed by GC external standard method. The results of the reaction are shown in Table 1.

[0032] Table 1. Diels-Alder reaction results in zinc chloride ionic liquid

[0033]

[0034]

[0035] The above results show that in the temperature range of 0℃-150℃, acrolein / isoprene / zinc chloride ionic liquid=1:1:10-1:1:1 (mol / mol / mol) in the reaction solution , Can obtain 4-methylcyclohexene-3-carbaldehyde, the yield is between 1%-95%.

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

No PUM Login to View More

Abstract

The invention relates to a method for preparing 4-methylbenzaldehyde from isoprene and acrolein. The method specifically comprises the following steps: enabling acrolein and analogues thereof to react with isoprene to carry out a Diels-Alder reaction at a proper temperature under the action of Lewis acidic ionic liquid to generate 4-methyl cyclohexene-3-formaldehyde and analogues thereof; by taking an organic solvent as a reaction medium and graphite oxide as a catalyst, carrying out a dehydrogenation reaction on 4-methyl cyclohexene-3-formaldehyde under proper temperature and pressure, and preparing 4-methylbenzaldehyde (4-methylbenzaldehyde, MBAD for short). According to the method disclosed by the invention, the isoprene and acrolein are taken as raw materials and are subjected to a simple two-step reaction to generate an aromatic target product with high additional value; the raw materials can be prepared from biomass resources, the product is cheap, regenerative, convenient to operate and high in yield, and a novel method for directly preparing chemicals from biomasses is provided.

Description

Technical field [0001] The invention relates to a method for preparing p-tolualdehyde from isoprene and acrolein. Specifically, first, under the action of Lewis acidic ionic liquid, at an appropriate temperature, isoprene and acrolein undergo Diels-Alder reaction to produce 4-methylcyclohexene-3-carbaldehyde (4-methylcyclohex-3 -enecarbaldehyde); 4-methylcyclohexene-3-carbaldehyde continues to use an organic solvent as the reaction medium, and the dehydrogenation reaction occurs under the action of a catalyst at appropriate temperature and pressure to prepare 4-methylbenzaldehyde (4-methylbenzaldehyde) , Abbreviated as MBAD) method. The isoprene and acrolein of the present invention can be obtained from petroleum resources and can also be obtained from biomass conversion. Therefore, the raw materials have the characteristics of being renewable. In addition, the route obtains aromatic compounds through a two-step reaction. The reaction route is short and the operation is conveni...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/542C07C45/65C07C45/69C07C47/42
CPCC07C45/65C07C45/69C07C47/542C07C47/42
Inventor 蔡海乐李昌志王爱琴张涛
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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