Method for preparing 2, 2 '-dihydroxy-3, 3', 5, 5 '-tetra-tert-butylbiphenyl by using microchannel reactor

A technology of microchannel reactor and di-tert-butylphenol, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of reducing the oxidation reaction rate, unfavorable for scale-up production, difficult separation, etc., to achieve Small footprint, good raw material mixing effect, and good product selectivity

Pending Publication Date: 2022-05-27
SHANGHAI CHEM REAGENT RES INST
View PDF7 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The synthesis method is mainly divided into base-catalyzed reaction using hydrogen peroxide according to the different oxidizing agents used. US Patent No. 4,380,676 discloses a 2,2'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl The synthetic method adopts alkali catalysis and hydrogen peroxide as an oxidant, and is characterized in that hydrogen peroxide is slowly added dropwise at high temperature (80° C.) to control the reaction speed and ensure the safety of the reaction. Therefore, it is dangerous and unfavorable for scale-up production; The intermittent reaction needs to be supplemented more, and the efficiency is low
[0004] Using air or oxygen as the oxidant requires transition metals (copper or cobalt complexes (CN201911011611.5)) as catalysts, and sometimes organics as solvents, which will not only cause subsequent separation difficulties, but also reduce the oxidation reaction in order to prevent explosions. rate
[0005] The preparation methods reported so far all use a batch reaction method, and the reaction process needs to be completed in multiple steps. Therefore, it is necessary to develop an efficient and safe synthetic method to improve the 2,2'-dihydroxy-3,3',5,5'- Production efficiency of tetra-tert-butylbiphenyl

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 2, 2 '-dihydroxy-3, 3', 5, 5 '-tetra-tert-butylbiphenyl by using microchannel reactor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The adopted microchannel reactor adopts the G1 reaction equipment of Corning Company, uses the metering pump to transport the reaction solution, and sets the module temperature of the first reaction area to 100°C and the module temperature of the second reaction area to 30°C.

[0034] Configuration of solution A: 400 g (10 mol) of sodium hydroxide is dissolved in 2000 g of water, and 1030 g (5 mol) of 2,4-di-tert-butylphenol is added under heating to fully dissolve.

[0035] The flow rate of solution A was 15ml / min, 30% hydrogen peroxide was 15ml / min, toluene was 30ml / min, and sulfuric acid (98%) was pumped into the corresponding reaction module at 2.6ml / min. After the reaction was stabilized, solution D was taken and detected by liquid chromatography: the conversion rate of 2,4-di-tert-butylphenol was 98.6%, and the target product 2,2'-dihydroxy-3,3',5,5'-tetra-tert-butyl The selectivity to biphenyl was 98.2%.

Embodiment 2

[0037] The microchannel reactor used was the G2 reaction equipment of Corning Company, the reaction solution was delivered by a metering pump, and the temperature of the first reaction area module was set to 95°C, and the temperature of the second reaction area module was set to 50°C.

[0038] Configuration of solution A: 400 g (10 mol) of sodium hydroxide is dissolved in 2000 g of water, and 1030 g (5 mol) of 2,4-di-tert-butylphenol is added under heating to fully dissolve.

[0039] The flow rate of solution A is 45ml / min, 30% hydrogen peroxide is 45ml / min, toluene is 90ml / min, and sulfuric acid (98%) is pumped into the corresponding reaction module at 7.8ml / min. After the reaction is stable, solution D is taken and detected by liquid chromatography: the conversion rate of 2,4-di-tert-butylphenol is 98.1%, and the target product 2,2'-dihydroxy-3,3',5,5'-tetra-tert-butyl The selectivity to biphenyl was 98.7%.

Embodiment 3

[0041] The microchannel reactor used was the G1 reaction equipment of Corning Company, and a metering pump was used to transport the reaction solution. The temperature of the first reaction zone module was set to 80°C, and the temperature of the second reaction zone module was set to 50°C.

[0042] Configuration of solution A: 561 g (10 mol) of sodium hydroxide was dissolved in 1839 g of water, and 1030 g (5 mol) of 2,4-di-tert-butylphenol was added under heating until fully dissolved.

[0043]The flow rate of solution A was 15ml / min, 30% hydrogen peroxide was 15ml / min, toluene was 30ml / min, and sulfuric acid (98%) was pumped into the corresponding reaction module at 2.6ml / min. After the reaction was stabilized, solution D was taken and detected by liquid chromatography: the conversion rate of 2,4-di-tert-butylphenol was 95.8%, and the target product 2,2'-dihydroxy-3,3',5,5'-tetra-tert-butyl The selectivity to biphenyl was 98.4%.

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 2, 4-difluorobenzene by using a The invention discloses a method for preparing 2, 2 '-dihydroxy-3, 3', 5, 5 '-tetra-tert-butylbiphenyl, which comprises the following steps: preparing a mixed solution from 2, 4-di-tert-butylphenol and alkali liquor according to a certain proportion, respectively pumping the mixed solution and a hydrogen peroxide solution into a micro-channel reactor, fully mixing, reacting the mixed material in a first reaction area module of the micro-channel reactor, mixing with toluene in a mixing area module, and reacting at the temperature of 80-90 DEG C to obtain the 2, 2'-dihydroxy-3, 3 ', 5, 5'-tetra-tert- The method comprises the following steps: adding a toluene solution into a first reaction area module, carrying out a neutralization reaction on the toluene solution and an acid solution in a second reaction area module, carrying out continuous phase separation on the obtained product solution to obtain a toluene solution D containing 2, 2 '-dihydroxy-3, 3', 5, 5 '-tetra-tert-butylbiphenyl, and carrying out concentration, crystallization and washing to obtain the target product 2, 2'-dihydroxy-3, 3 ', 5, 5'-tetra-tert-butylbiphenyl. By utilizing the method, the reaction efficiency can be obviously improved, the reaction time is greatly shortened, the possible explosion risk is avoided, the production process is more convenient to control, the production cost is reduced, and the defects of high labor intensity, long production period, low product quality and the like in the traditional production are overcome.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for preparing 2,2'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl by using a microchannel reactor. Background technique [0002] 2,2'-Dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl is an important raw material for the synthesis of bidentate phosphine ligands in carbonyl hydroformylation. At present, it is mainly prepared by oxidative coupling in industry. get. [0003] Its synthesis method is mainly divided into alkali-catalyzed reaction using hydrogen peroxide according to the different oxidants used. US Patent US4380676 discloses a kind of 2,2'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl. The synthesis method adopts alkali catalysis and hydrogen peroxide as an oxidant, and is characterized in that the hydrogen peroxide is slowly added dropwise at a high temperature (80° C.) to control the reaction speed and ensure the safety of the reaction, so it i...

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): C07C37/16C07C37/01C07C37/66C07C39/15
CPCC07C37/16C07C37/01C07C37/66C07C39/15
Inventor 龚磊张传好周励
Owner SHANGHAI CHEM REAGENT RES INST
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