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

Synthesis method of chlorinated phenol compound

A technology of phenolic compounds and chlorinated phenols, which is applied in the field of green catalytic synthesis of chlorinated phenolic compounds, can solve the problems of large catalyst ratio, reduced reaction efficiency, unfavorable industrialization, etc., and achieves high selectivity, efficient catalytic reaction, and separation convenient effect

Pending Publication Date: 2022-07-29
SHAANXI COAL & CHEM TECH INST
View PDF6 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method uses a large proportion of catalyst, and a large amount of water is added in the reaction process, which reduces the reaction efficiency and is not conducive to industrialization.
Chinese patent application 201110084533.9 proposes a technical scheme for oxidative chlorination to obtain 4-chloro-3,5-dimethylphenol by using divalent copper salt and chlorine-containing inorganic substances as a catalytic system, but this reaction will produce ether dimers , resulting in a lower reaction yield

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
  • Synthesis method of chlorinated phenol compound
  • Synthesis method of chlorinated phenol compound
  • Synthesis method of chlorinated phenol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1 Synthesis of alkyl imidazole ionic liquid

[0028] 1) The preparation process of 1-allyl-3-methylimidazole ionic liquid is as follows:

[0029] 200mL of allyl chloride and 132mL of methylimidazole were added to a 500mL flask respectively, magnetically stirred at 60°C, refluxed for 10h, cooled down and then rotary-evaporated, and the excess allyl chloride was spun out to obtain 1-allyl group -3-methylimidazolium chloride, which is light yellow transparent liquid with a yield of about 92%;

[0030] 2) The preparation process of 1-butyl-3-methylimidazolium ionic liquid is as follows:

[0031] 142mL of n-chlorobutane and 100mL of methylimidazole (molar ratio 1.1:1) were added to a 500mL flask, refluxed at 100°C for 48h, magnetically stirred, and then rotary-evaporated to obtain a light yellow transparent liquid, which was cooled to White solid in 95% yield.

[0032]The preparation process of Lewis acid alkyl imidazolium ionic liquid is as follows:

[0033] ...

Embodiment 2

[0046] 15g (0.122mol) 3,5-dimethylphenol, 30g CuCl 2 / 1-allyl-3-methylimidazolium chloride ionic liquid complex was put into a 100mL four-necked flask, and 15.74mL of hydrochloric acid (mass fraction 37%) was added, and the reaction was carried out by introducing oxygen at 70 ° C for 9 hours, The conversion rate is greater than 96%, and the selectivity is greater than 93%. After the reaction was completed, suction filtration was performed, and the obtained crude product was recrystallized with tetrachloroethylene to obtain 16.5 g of pure 4-chloro-3,5-dimethylphenol with a purity of 99.3%, and the yield was 86%.

[0047]

Embodiment 3

[0049] The CuCl isolated after the reaction of Example 2 is used in Example 3 2 / 1-allyl-3-methylimidazolium ionic liquid, Examples 4-8 sequentially use the CuCl separated after the reaction in the previous example 2 / 1-allyl-3-methylimidazole ionic liquid, the effect of repeated recycling on the reaction is shown in Table 1.

[0050] Table 1. CuCl 2 / 1-allyl-3-methylimidazolium ionic liquid cycle times and conversion rate, yield comparison

[0051]

[0052]

[0053] It can be seen from Table 1 that the CuCl2 / 1-allyl-3-methylimidazolium ionic liquid catalyst still has good catalytic activity after being recycled for 6 times, and the conversion rate and yield are relatively stable. In industrial production, It is beneficial to reduce the cost and avoid the generation of waste liquid.

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 provides a synthetic method of a chlorinated phenol compound, which takes Lewis acid series alkyl imidazole ionic liquid as a catalyst, and a phenol compound, hydrochloric acid and an oxidizing agent are subjected to an oxidation chlorination reaction to obtain the chlorinated phenol compound. Hydrochloric acid is used as a chlorinating agent, so that the use of chlorine, sulfonyl chloride and other environment-unfriendly chlorinating agents is avoided, and the method is green and environment-friendly; the Lewis acid series alkyl imidazole ionic liquid is adopted as the catalyst, no organic solvent is needed, the catalytic activity is high, the selectivity is high, product separation is facilitated, waste liquid is not generated, industrial production is facilitated, and the cost is reduced.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a green catalytic synthesis method of chlorinated phenol compounds. Background technique [0002] Chlorinated phenols are a class of important chemical intermediates, and are the starting materials for the synthesis of important chemical products such as organometallic reagents, fine chemicals, medicines, and pesticides. One of the most common monochlorophenols, such as PCMC (4-chloro-3-methylphenol), is an important preservative for functional fluids and an important raw material for disinfectants. It is also used in organic synthesis raw materials, pigments Intermediates and film film preservatives, etc. [0003] Chlorination reaction is a chemical reaction with important application value. In industry, the traditional synthesis process of chlorinated phenols is to use chlorine, sulfuryl chloride or other N-chlorinated reagents as chlorinating agents to ...

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): C07C37/62C07C37/84C07C39/28B01J31/02B01J31/30B01J31/32B01J31/26B01J31/28
CPCC07C37/62C07C37/84B01J31/0281B01J31/30B01J31/32B01J31/26B01J31/28C07C39/28
Inventor 王宪沛韩劲松郑绍华严良张磊徐婕祝媛高伟伟
Owner SHAANXI COAL & CHEM TECH INST
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