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

Benzotriazole Schiff base compound and preparation method thereof

A technology of benzotriazole Schiff bases and benzotriazoles is applied in the field of benzotriazole Schiff base compounds and preparation thereof, and can solve the problems such as rare benzotriazole Schiff base compounds, and achieves The synthesis method is simple, the yield is high, and the operation is simple.

Inactive Publication Date: 2013-07-10
SOUTHWEST PETROLEUM UNIV
View PDF3 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are few reports on benzotriazole Schiff base compounds at home and abroad

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
  • Benzotriazole Schiff base compound and preparation method thereof
  • Benzotriazole Schiff base compound and preparation method thereof
  • Benzotriazole Schiff base compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: Preparation of benzotriazole Schiff base compound:

[0018] (1) Add 3.26g (20mmol) 5-carboxybenzotriazole and appropriate amount of LiAlH to a 100ml round bottom flask 4 and THF, control the temperature at about 20°C, add an appropriate amount of TPAP / NMO, CH 2 Cl 2 , THF, DMF at room temperature for 12 hours, and filtered under reduced pressure to obtain 2.62 g of white crude product 5-formylbenzotriazole A. (Yield: 89%)

[0019] (2) Add 2.62g (18mmol) A, 0.54g (18mmol) formaldehyde, 20ml acetic acid, 50ml water to a 100ml round-bottomed flask in turn, stir for 1h, place for 2h, and filter under reduced pressure to obtain the white crude product 1-hydroxymethyl Base-5-formylbenzotriazole B2.88g. (Yield: 90%)

[0020] (3) Add 2.83g (16mmol) B and 30ml CHCl to a 100ml double-necked bottle in sequence 3 and 1.5g of phase transfer catalyst tetrabutylammonium bromide TBAB, heated to dissolve. Slowly add the aqueous solution containing 1.60g (16mmol) chr...

Embodiment 2

[0027] Embodiment 2: Preparation of benzotriazole Schiff base compound:

[0028] (1) Add 3.26g (20mmol) 5-carboxybenzotriazole and appropriate amount of LiAlH to a 100ml round bottom flask 4 and THF, the temperature is controlled at around 40°C. After electromagnetic stirring for 12 hours, add an appropriate amount of TPAP / NMO, CH 2 Cl 2 , THF, DMF at room temperature for 8 hours, and filtered under reduced pressure to obtain 2.14 g of white crude product 5-formylbenzotriazole A. (Yield: 73%)

[0029] (2) Add 2.14g (14.5mmol) A, 0.45g (15mmol) formaldehyde, 20ml ethanol, 50ml water to a 100ml round-bottomed flask in sequence, stir for 1.5h, let stand for 2h, and filter under reduced pressure to obtain the white crude product 1- Hydroxymethyl-5-formylbenzotriazole B2.00g. (Yield: 78%)

[0030] (3) Add 1.95g (11mmol) B and 21ml CHCl to a 100ml double-necked bottle in sequence 3 and 1.1 g of phase transfer catalyst tetrabutylammonium bromide TBAB, heated to dissolve. Slow...

Embodiment 3

[0033] Embodiment 3: Preparation of benzotriazole Schiff base compound:

[0034](1) Add 3.26g (20mmol) 5-carboxybenzotriazole, appropriate amount of LiAlH4 and THF into a 100ml round bottom flask, control the temperature at about 20°C, add an appropriate amount of TPAP / NMO dropwise after electromagnetic stirring for 10 hours, CH2Cl2, THF, DMF were reacted at room temperature for 12 hours, and the white crude product 5-formylbenzotriazole A2.62g was obtained after suction filtration under reduced pressure. (Yield: 89%)

[0035] (2) Add 2.62g (18mmol) A, 0.54g (18mmol) formaldehyde, 20ml acetic acid, 50ml water to a 100ml round-bottomed flask in turn, stir for 1h, place for 2h, and filter under reduced pressure to obtain the white crude product 1-hydroxymethyl Base-5-formylbenzotriazole B2.88g. (Yield: 90%)

[0036] (3) Add 2.83g (16mmol) B and 30ml CHCl to a 100ml double-necked bottle in sequence 3 and 1.0 g of phase transfer catalyst tetrabutylammonium bromide TBAB, heated...

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 preparation method for a benzotriazole Schiff base compound. A synthetic method comprises the steps of: (1) adding 5-carboxy benzotriazole, LiAlH4 and THF (tetrahydrofuran) into a flask, dripping TPAP / NMO (tetrapropylammonium perruthenate / N-morpholine oxide), CH2Cl2, THF and DMF (dimethyl formamide) after stirring for 2 hours, and reacting for 12 hours, so as to obtain white 5-aldehyde benzotriazole; (2) sequentially adding the product obtained in the step (1), formaldehyde, acetic acid and water into the flask, and carrying out stirring, standing and suction filtration, so as to obtain white 1-hydroxymethyl-5-aldehyde benzotriazole; (3) adding the product obtained in the step (2), CHCl3 and TBAB (tetrabutylammonium bromide) into the flask, dropwise adding CrO3 and a concentrated H2SO4 water solution after heating and dissolving the mixture, stirring until the solution becomes deep green, skimming, regulating the pH of an inorganic layer to be approximate to 8, and carrying out chloroform extraction, anhydrous sodium sulfate drying and rotary evaporation, so as to obtain orange red 1,5-dialdehyde benzotriazole; and (4) adding the product obtained in the step (3) into the flask, adding 6-aminoquinoline after dissolving the product by the ethanol, and carrying out backflow, filtering and recrystallization, so as to obtain a target compound of benzotriazole Schiff base. According to the target compound, the structure is novel, the corrosion inhibition performance is high, and the problem of acid washing of carbon steel can be effectively solved.

Description

technical field [0001] The invention relates to a benzotriazole Schiff base compound and a preparation method thereof. Background technique [0002] Pickling is widely used in metal materials, machinery, metallurgy, electric power and chemical industries. Pickling in industry includes pickling to remove scale, metal materials and pickling and descaling of equipment. Pickling it can not only produce huge social and economic benefits, but also has great significance for safety issues and environmental protection. [0003] Acids commonly used in the pickling process include hydrochloric acid, sulfuric acid, and nitric acid. In the pickling process, the acid has a corrosive effect on metal equipment and materials, especially inorganic acid; in addition, the hydrogen gas generated by the reaction of metal and acid will cause hydrogen embrittlement of the metal equipment, and the hydrogen will also bring out a certain amount of acid gas, forming Internal acid mist, causing the ...

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): C07D249/18C23G1/06C23G1/08
Inventor 诸林刘红王治红
Owner SOUTHWEST PETROLEUM UNIV
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