Method for preparing hydrazone compound

A technology of aldehyde compounds and compounds, applied in the preparation of hydrazones, organic chemistry, etc., can solve problems such as hydrazone compounds that have not been disclosed

Inactive Publication Date: 2013-08-28
SHANGHAI JUTAI SPECIAL REAGENT CO LTD
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] P-Chlorophenylhydrazine hydrochloride is often used as an intermediate in organic synthesis. PCBs will inevitably be produced during the drying and storage of p-chlorophenylhydrazine hydrochloride, although sometimes the content of PCBs is very low. Only 100ppm, but because polychlorinated biphenyls are strong carcinogens, there is zero tolerance in the pharmaceutical, pesticide and food industries, so even a small amount is not allowed, so the unreacted p-chlorophenylhydrazine hydrochloride It is very necessary to remove
[0004] Hydrazone compounds are organic chemical intermediates that can form a series of nitrogen-containing heterocyclic compounds; they are important intermediates for medicine and pesticides. At present, there is no method for effectively preparing hydrazone compounds in China.

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: Get the R base to be hydrogen, that is, the aldehyde compound is glyoxal, and the chemical formula is C 2 o 2 h 2 .

[0032] 1) Dissolving p-chlorophenylhydrazine hydrochloride in water, and extracting and removing polychlorinated biphenyls under the protection of an inert gas, to obtain a polychlorinated biphenyl-free aqueous solution of p-chlorophenylhydrazine hydrochloride;

[0033] 2) Mix glyoxal with deionized water to obtain an aqueous solution of glyoxal with a concentration of 0.5 mol / L;

[0034] 3) Add the p-chlorophenylhydrazine hydrochloride aqueous solution obtained in the above step 1) and the glyoxal aqueous solution prepared in the above step 2) into a reactor at the same time, and control the reaction temperature in the reactor to 25°C. The reaction pH value is PH5~6, and the adding speed of controlling the p-chlorophenylhydrazine hydrochloride aqueous solution is 0.1mol / min, and the adding speed of controlling the glyoxal aqueous soluti...

Embodiment 2

[0037] Example 2: Take the R group as a hydroxyl group (—OH), that is, the aldehyde compound is glyoxylic acid, and the chemical formula is CHOCO 2 H.

[0038] 1) Dissolve p-chlorophenylhydrazine hydrochloride in water, remove polychlorinated biphenyls under the protection of inert gas, and obtain a polychlorinated biphenyl-free aqueous solution of p-chlorophenylhydrazine hydrochloride;

[0039] 2) Mix glyoxylic acid with deionized water to obtain a glyoxylic acid aqueous solution with a concentration of 0.5mol / L;

[0040] 3) Add the p-chlorophenylhydrazine hydrochloride aqueous solution obtained in the above step 1) and the glyoxylic acid aqueous solution prepared in the above step 2) into a reactor at the same time, and control the reaction temperature in the reactor to 23-26 ℃, the reaction pH value is PH5~6, the adding rate of p-chlorophenylhydrazine hydrochloride aqueous solution is controlled to be 0.15mol / min, the adding rate of glyoxylic acid aqueous solution is contr...

Embodiment 3

[0043] Embodiment 3: get the R base to be an alkyl group (—CH 3 ), that is, the aldehyde compound is methylglyoxal, and its chemical formula is CH 3 COCHO.

[0044] 1) Dissolve p-chlorophenylhydrazine hydrochloride in water, remove polychlorinated biphenyls under the protection of inert gas, and obtain a polychlorinated biphenyl-free aqueous solution of p-chlorophenylhydrazine hydrochloride;

[0045] 2) Mix methylglyoxal with deionized water to obtain an aqueous solution of methylglyoxal with a concentration of 1 mol / L;

[0046]3) Add the p-chlorophenylhydrazine hydrochloride aqueous solution obtained in the above step 1) and the aceguvaldehyde aqueous solution prepared in the above step 2) into a reactor at the same time, and control the reaction temperature in the reactor to 26-30°C , the reaction pH value is PH5~6, and the adding speed of controlling p-chlorophenylhydrazine hydrochloride aqueous solution is 0.2mol / min, and the adding speed of controlling the methylglyoxal...

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 discloses a method for preparing a hydrazone compound. The method is characterized in that an aldehyde compound is used to continuously chemically react with p-chlorophenylhydrazine hydrochloride under the protection of N2, and the reaction formula is shown as follows: p-ClC6H4N2H3-HCl+RCOCHO->p-ClC6H4NHNCH-COR+HCl+H2O, wherein R is any one of hydrogen, alkyl or hydroxyl. The method for preparing the hydrazone compound has the beneficial effects that the prepared hydrazone compound excludes polychlorinated biphenyl, the aldehyde compound is adopted and reacts with p-chlorophenylhydrazine hydrochloride, the reaction condition is controlled, and the process is optimized, therefore, the p-chlorophenylhydrazine hydrochloride can be reacted completely, polychlorinated biphenyl cannot be produced by the p-chlorophenylhydrazine hydrochloride, and production of dihydrazone impurities in the reaction can be avoided. The excessive aldehyde compound can be recycled, so that economy and environmental protection are realized.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to a method for preparing hydrazone compounds. Background technique [0002] Polychlorinated biphenyls, alias chlorinated biphenyls, English name: Polychorinated biphenyls, referred to as PCBs. In my country, PCB is traditionally divided into trichlorobiphenyl (PCB3), tetrachlorobiphenyl (PCB4), pentachlorobiphenyl (PCB5), hexachlorobiphenyl (PCB3) Benzene (PCB6) and so on. PCBs are strong carcinogens that tend to accumulate in adipose tissue, causing diseases of the brain, skin and internal organs, and affecting nerves, reproduction and immunity. [0003] P-Chlorophenylhydrazine hydrochloride is often used as an intermediate in organic synthesis. PCBs will inevitably be produced during the drying and storage of p-chlorophenylhydrazine hydrochloride, although sometimes the content of PCBs is very low. Only 100ppm, but because polychlorinated biphenyls are stro...

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): C07C249/16C07C251/76
Inventor 郭建国陈怀涛邵杏芝
Owner SHANGHAI JUTAI SPECIAL REAGENT CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap