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Method for catalytic reaction of chloromethylation of aromatic cyclic compound

A technology for aromatic ring compounds and chloromethylation, applied in chemical instruments and methods, organic chemistry, chemical recovery, etc., can solve the problems of long time, low yield, low reactivity, etc.

Inactive Publication Date: 2010-07-14
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the reaction activity is low, the time is long, and the yield is not high, due to the low price of raw materials, convenient storage and transportation, and low toxicity, it is still the most widely used, especially how to improve the efficiency of the reaction system such as increasing activity, yield, and shortening the reaction time. , is still a research hotspot

Method used

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  • Method for catalytic reaction of chloromethylation of aromatic cyclic compound
  • Method for catalytic reaction of chloromethylation of aromatic cyclic compound
  • Method for catalytic reaction of chloromethylation of aromatic cyclic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]In a three-necked flask equipped with a thermometer and a reflux condenser, add 0.3mol of toluene, 0.6mol of paraformaldehyde, add 0.024mol of 1,3-propanesulfonic acid pyridinium ylide (8% of the amount of toluene), and add For a hydrochloric acid solution twice the volume of toluene, wait until the temperature of the oil bath rises to 80°C, continue to feed hydrogen chloride gas, and react at a constant temperature for 10 hours;

[0031] After the reaction finished, the reaction system was divided into two layers, and the upper strata was made up of unreacted toluene and product, and the lower floor was an aqueous phase (onium salt was dissolved in it), and by GC / MS gas chromatography analysis, the product was monochloromethyltoluene ( Main product is p-methyl chlorobenzene, o-methyl chlorobenzene), for the quantification of reactant and product, measure (internal standard quantification) with GC9800 gas chromatograph of U.S. PE company, the product that content is less ...

Embodiment 2

[0033] In the there-necked flask equipped with a thermometer and a reflux condenser, add m-xylene 0.3mol, formaldehyde solution 0.6mol, add 1,3-propanesulfonic acid pyridinium ylide 0.024mol (8% of the amount of toluene substance), and After adding 0.03mol of zinc chloride, then add a hydrochloric acid solution twice the volume of toluene, wait until the temperature of the oil bath rises to 85°C, continue to feed hydrogen chloride gas, and react at a constant temperature for 10 hours;

[0034] After the reaction finishes, the reaction system is divided into two layers, the upper layer is made up of unreacted toluene and the product, the lower floor is an aqueous phase (onium salt is dissolved therein), and the product is monochloromethyl m-xylene (the main product is p-monochloromethyl m-xylene, ortho-monochloromethyl m-xylene), the conversion rate of m-xylene reaches 85.7%, and the selectivity is 98.4%. The ionic liquid is directly reused, or reused through simple dehydration....

Embodiment 3

[0036] In the there-necked flask equipped with a thermometer and a reflux condenser, add o-xylene 0.3mol, formaldehyde solution 0.6mol, add 1,3-propanesulfonic acid pyridinium ylide 0.024mol (8% of the amount of toluene substance), and After adding 0.075mol of zinc chloride, then add hydrochloric acid solution twice the volume of toluene, wait until the temperature of the oil bath rises to 85°C, continue to feed hydrogen chloride gas, and react at constant temperature for 10h;

[0037] After the reaction finishes, the reaction system is divided into two layers, the upper layer is made up of unreacted toluene and the product, the lower layer is an aqueous phase (onium salt is dissolved in it), and the product is monochloromethyl o-xylene (the main product is p-monochloromethyl ortho-xylene, ortho-monochloromethyl-o-xylene), the conversion rate of ortho-xylene reaches 86.8%, and the selectivity is 97.6%. The ionic liquid can be reused directly or through simple dehydration.

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Abstract

The invention relates to a method for the catalytic reaction of the chloromethylation of an aromatic cyclic compound. In the chloromethylation reaction system of the aromatic cyclic compound, formaldehyde, hydrochloric acid and introduced hydrogen chloride of the method, onium salt compound in alkylamine sulfonate is singly added to service as the catalyst, or a compound combined catalyst is added to carry out the chloromethylation reaction of the aromatic compound, wherein onium salt compound in alkylamine sulfonate serves as the main catalyst, and inorganic acid or organic acid or Lewis acid serves as the catalyst promoter in the compound combined catalyst. In the strong acid condition of the chloromethylation reaction, the onium salt compound in alkylamine sulfonate forms an ion-state compound, i.e. reacting with the acid to form an ion-state liquid. The liquid has the functions of the acidic ionic liquid and the phase transition. The catalyst is universally applicable to the chloromethylation reaction of the aromatic cyclic compound, and the reaction method has the characteristics of high conversion rate, good selectivity and convenient aftertreatment. After being recycled, the catalyst can be directly reused.

Description

technical field [0001] The invention relates to a catalytic reaction method for chloromethylation of aromatic ring compounds Background technique [0002] Chloromethylation of aromatic ring compounds is a widely used chemical reaction, and aromatic ring compounds are introduced into -CH by nucleophilic substitution 2 Cl, -CH 2 Cl can be conveniently obtained by further reaction containing such as -CHO, -CH 2 OH, -CH 2 CN, -CHNR 2 Derivatives of such groups can obtain a series of valuable intermediate products or chemicals, which are widely used in the fields of medicine, pesticides, dyes, spices, polymers, etc. There are many reports on the research and application of this reaction. [0003] The classic Blanc chloromethylation reaction uses formaldehyde, paraformaldehyde or paraformaldehyde and hydrochloric acid as the chloromethylation reaction reagent system, and chloromethylation is an acid-catalyzed reaction, wherein the protonic acid H 2 SO 4 , HCl, H 3 PO 4 And...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/32C07C22/04
CPCY02P20/584
Inventor 赵文军王旭尚洁王华高林文彬杨丹红王强向迎梅
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI