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Preparation method of 2, 2'-biphenyl diphenol and derivatives thereof

A technology for biphenol and derivatives, which is applied in the field of preparation 2, can solve the problems of reactor and agitator pollution, complicated post-processing, noise pollution, etc., and achieves the effect of a simple and economical synthesis method and simple and easy post-processing.

Active Publication Date: 2010-09-01
合肥华纳生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Yet, the synthetic 3 of US6077979 development, 3 ', 5, the problem of the method for 5 '-tetramethyl-2,2 '-biphenol is that can form rubbery viscous substance in reaction process, and this will Contamination of reactors and mixers
Especially in industrial production, heat exchange and full mixing of all raw materials are almost impossible to achieve, and complete conversion of raw materials cannot be achieved
In addition, the rubber-like viscous substance makes post-processing extremely complicated
[0006] However, the problem of the method for synthesizing 2,2'-biphenol and its derivatives by means of ultrasonic radiation is that serious noise pollution will be produced, and this method cannot realize industrialized production

Method used

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  • Preparation method of 2, 2'-biphenyl diphenol and derivatives thereof
  • Preparation method of 2, 2'-biphenyl diphenol and derivatives thereof

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Experimental program
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Effect test

Embodiment 1

[0038] 50g (300mmol, 1eq) of 4-methyl-2-tert-butylphenol and 8.11g (150mmol, 0.5eq) of ferric trichloride were added to 250mL of dioxane, and then 31mL (27.4g , 300mmol, 1eq) tert-butyl hydroperoxide, dripped in 40 minutes. After the dropwise addition, the system was heated to 80° C. for 4 hours to react. After the reaction, the dioxane was distilled off under reduced pressure, and the residue was recrystallized from petroleum ether to obtain 44.0 g of 2,2'-di-tert-butyl-4,4'-dimethylbiquinone, with a yield of 90%. . H NMR spectrum ( 1 H NMR, 300MHz, CDCl 3 )δ7.14-7.12 (d, J m =1.25Hz, 2H); 7.00-6.88(d, J m = 1.25 Hz, 2H); 5.18 (s, 2H); 2.30 (s, 6H); 1.242 (s, 18H). MS: m / z 326 (M+); 311; 255.

Embodiment 2

[0040] 77g (500mmol, 1eq) of 3,4-dimethoxyphenol and 17.4g (62.5mmol, 0.125eq) of ferrous sulfate heptahydrate were added to 400mL of toluene, and then 26mL (22.9g, 250mmol, 0.5eq) tert-butyl hydroperoxide, dripped in 30 minutes. After the dropwise addition, the system was heated to 85° C. for 5 hours to react. After the reaction, the dioxane was distilled off under reduced pressure, and the residue was subjected to petroleum ether column chromatography to obtain 62.0 g of 3,3',4,4'-tetramethoxybiquinone with a yield of 81%. H NMR spectrum ( 1 H NMR, 300MHz, CDCl 3 ) δ 7.08 (s, 2H); 6.49 (s, 2H); 5.35 (s, 2H); 3.88 (s, 6H); 3.75 (s, 6H). MS: m / z 306 (M+).

Embodiment 3

[0042] Add 170g (1mol, 1eq) 4-phenylphenol and 40.5g (0.25mol, 0.25eq) ferric trichloride to 850mL ethyl acetate respectively, then add 220mL (175.2g, 1.2mol, 1.2eq) dropwise at room temperature ) di-tert-butyl peroxide, dripped in 150 minutes. After the dropwise addition, the system was heated to 75° C. for 6 hours. After the reaction, ethyl acetate was distilled off under reduced pressure, and the residue was subjected to petroleum ether column chromatography to obtain 118.3 g of 4,4'-diphenylbiphenyldiphenol, with a yield of 70%. H NMR spectrum ( 1 H NMR, 300MHz, CDCl 3 )δ7.58-7.41 (m, 14H); 7.07 (d, J o = 6.2 Hz, 2H); 5.12 (s, 2H). MS: m / z 338 (M+).

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Abstract

The invention provides a method for preparing 2, 2'-biphenyl diphenol derivatives, and the method comprises the step of carrying out oxidation coupling reaction on phenolic compound A with ortho-hydrogen atoms at 0-100DEG C with the help of peroxide, thus preparing 2, 2'-biphenyl diphenol compound B; and the method is simpler and more economical, the post processing is simple and easy to implement and has good universality, and the method can provide a series of 2, 2'-catechol derivatives.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for preparing 2,2'-diphenol and derivatives thereof. Background technique [0002] 2,2'-biphenol and its derivatives are a very important class of organic chemical products. It can be used as an intermediate raw material for liquid crystal polymers. In terms of synthesizing high polymers, because of its excellent heat resistance, it can be used as a modified monomer for polymer materials such as polyester, polyurethane, polycarbonate, polysulfone and epoxy resin, and is used to manufacture excellent engineering materials. Plastics and composites. It can also be used as rubber anti-aging agent, plastic antioxidant and stabilizer for dye intermediates or petroleum products. Recently, people have used the chelating function of the oxygen atom in the molecular structure of 2,2'-biphenol and its derivatives to prepare bidentate ligands, which are used as catalyst accelera...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B37/00C07C39/15C07C43/23C07C39/367C07C37/11C07C41/30
Inventor 许峰高源
Owner 合肥华纳生物医药科技有限公司
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