Prepn process of 3,3',5,5'-tetraalkyl-4,4'-diphenol

A technology of biphenyldiphenol and dialkylphenol, which is applied in 3 fields, can solve the problems of poor reaction selectivity, etc., and achieve the effects of less equipment investment, novel synthesis method and simple synthesis process

Inactive Publication Date: 2005-12-14
GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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Problems solved by technology

In the two-step method, the first step generates quinones, and then reduces them to obtain phenols. However, in the first step, precious metals such as palladium and rhodium are often used as catalysts, and the reaction selectivity is poor, and it is easy to form compounds such as 2,6-dimethyl p- A series of by-products such as benzoquinone and polyphenylene ethers of different molecular weights

Method used

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  • Prepn process of 3,3',5,5'-tetraalkyl-4,4'-diphenol
  • Prepn process of 3,3',5,5'-tetraalkyl-4,4'-diphenol
  • Prepn process of 3,3',5,5'-tetraalkyl-4,4'-diphenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 6.1g 2,6 dimethylphenol (0.05mol), after grinding, add 8.5g AgNO 3 (0.05mol), 50g deionized water, stirred, the temperature was controlled at 0 ° C, reacted for 4 hours, suction filtered, washed with water, then washed with NaOH solution, suction filtered and dried to obtain product 3.2g (0.013mol), yield 52% . Through infrared spectroscopy, 1 H-NMR proved to be 3,3',5,5'-tetramethyl-4,4'-biphendiquinone, and its data are as follows: IR (KBr, v cm -1 )1693, C=O, 1638, C=C, 1380, CH 3 ;exist 1 In the H-NMR chart, 7.700ppm is the chemical shift of H on the double bond in the quinone, 2.135ppm is the chemical shift of H on the methyl group, the integral area ratio is 1:3; the melting point is 215-217°C.

[0027] Take 2.4 g (0.01 mol) of 3,3',5,5'-tetramethyl-4,4'-diphenyldiquinone, add 50 mL of ethanol, and then add 19 g of NaHSO 3 (0.18mol) and 16.8g NaHCO 3 (0.2mol), then 18g of deionized water was added, and the solution was stirred at room temperature for 1 hour....

Embodiment 2

[0029] 3.1g 2,6-dimethylphenol (0.025mol), after grinding, add 54g FeCl 3 .6H 2 O (0.2mol), 40g deionized water, stirred, the temperature was controlled at 20 ° C, reacted for 4 hours, suction filtered, washed with water, then washed with NaOH solution, suction filtered and dried to obtain product 2.0g (0.008mol), yield 63 %.

[0030] Take 1.2 g (0.005 mol) of 3,3',5,5'-tetramethyl-4,4'-biphendiquinone, add 25 mL of ethanol, and then add 11 g of Na 2 S 2 O 3 (0.07mol) and 10gNH 4 NO 3 (0.125mol), then 9g of deionized water was added, and the solution was stirred at room temperature for 1 hour. The solution changed from red to nearly colorless lower layer, and the organic solvent layer was yellow. The mixture was allowed to stand still until the layers were separated, spun off to remove the ethanol, suction filtered, washed with water, and dried in vacuo to obtain 1.1 g (0.0045 mol) of a pale yellow solid with a yield of 92%.

Embodiment 3

[0032] 10.2g 2,6-di-tert-butylphenol (0.05mol), after grinding, add 10.0g copper acetate (0.05mol), 80g deionized water, N 2 Under the protection, stirring, the temperature is controlled at 20 ° C, the reaction is carried out for 4 hours, suction filtration, washing with water, then washing with NaOH solution, suction filtration and drying to obtain 3,3',5,5'-tetra-tert-butyl-4,4' - Biphendiquinone 7.69 g (0.02 mol), yield 63%.

[0033] Take 4.8 g (0.012 mol) of 3,3',5,5'-tetra-tert-butyl-4,4'-diphenyldiquinone, add 50 mL of dichloroethane, and then add 20.9 g of Na 2 S2 O 4 (0.12mol) and 40g Na 2 HPO 4 (0.28mol), then 18g of deionized water was added, and the solution was stirred for 1 hour. The solution changed from red to nearly colorless in the lower layer, and the organic solvent layer was yellow. Static to separate layers, spin off dichloroethane, suction filtration, wash with water, and vacuum dry to obtain 4.4 g of pale yellow solid 3,3',5,5'-tetra-tert-butyl-4,4'-...

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Abstract

The present invention is the preparation process of 3, 3', 5, 5'-tetralkyl-4, 4'-diphenol, and features that material 2, 6-dialkyl phenol is first oxidized and coupled with salt oxidant to produce 3, 3', 5, 5'-tetralkyl-4, 4'-biphenyl diquinone, and 3, 3', 5, 5'-tetralkyl-4, 4'-biphenyl diquinone is then reduced with cheap efficient inorganic reductant to obtain 3, 3', 5, 5'-tetralkyl-4, 4'-diphenol. The preparation process of the present invention is novel, mild in reaction condition, less in side product, simple and low in cost, has no need of blowing in oxygen or pressurizing air and special reaction apparatus, and has industrial application foreground.

Description

technical field [0001] The present invention relates to a preparation method of 3,3',5,5'-tetraalkyl-4,4'-biphenol. Background technique [0002] 3,3',5,5'-tetraalkyl-4,4'-biphenyldiol, a representative 3,3',5,5'-tetramethyl-4,4'-biphenyldiol Phenol is a pale yellow solid with a melting point of 223-225°C. 3,3',5,5'-tetramethyl-4,4'-biphenol is 3,3',5,5'-tetramethyl-4,4'-biphenyl diglycidyl ether the starting reactant. 3,3',5,5'-tetramethyl-4,4'-biphenyl diglycidyl ether can be used as semiconductor encapsulation, it has low melt viscosity, good storage stability and processability, its curing It has good crack resistance and welding resistance, and can be widely used in adhesives, powder coatings, epoxy molding compounds, etc., especially in the field of high-performance electronic plastic sealing. [0003] 3,3',5,5'-tetramethyl-4,4'-biphenol, the currently reported reaction preparation of it can adopt one-step method and two-step method. In the one-step method, the re...

Claims

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Application Information

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IPC IPC(8): C07C39/15
Inventor 凌有道吕满庚任少平
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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