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Biphenyl compound, synthetic method and application thereof

A synthesis method and compound technology, which is applied in the field of biphenyl compounds and their synthesis, can solve the problems of high cost, and achieve the effects of cost saving, shortening process flow, and green and clean production process

Inactive Publication Date: 2013-09-25
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the technologies for producing hydrogen peroxide in various countries are basically prepared by the anthraquinone method of DuPont Company in 1958. This method uses alkyl anthraquinone as a medium to produce hydrogen peroxide through cyclic oxidation and reduction, but the cost of this technology is relatively high. During the hydrogen peroxide process, waste gas containing a large amount of trimethylbenzene and xylene and waste water containing a large amount of organic pollutants are discharged

Method used

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  • Biphenyl compound, synthetic method and application thereof
  • Biphenyl compound, synthetic method and application thereof
  • Biphenyl compound, synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: the preparation of catalyst

[0040] 1.5,5'-dibromo-2,2'-diphenol (3.44g, 10mmol), 3-chloromethylpyridine hydrochloride (3.80g, 25mmol), K 2 CO 3 (27.6g, 200mmol), KI (0.60g, 3.6mmol), DMF 25mL, stirred at room temperature for 36h, the reactant was poured into water, suction filtered, and the filter cake was subjected to silica gel column chromatography (CH 2 Cl 2 :CH 3 OH=25:1), to obtain 4.27 g of white solid intermediate B with a yield of 812%.

[0041] 2.N 2 Under protection, intermediate B (5.26g, 10mmol), pyridine-4-boronic acid (3.08g, 25mmol), K 2 CO 3 (17.25g, 125mmol), placed in a 250mL three-necked flask, toluene, ethanol and water as solvent, adding catalyst Pd (PPh 3 ) 4 (1.2g, 1mmol), heat to reflux, control the temperature at 90°C-110°C, and control the reflux time at 24h. TLC tracking, left standstill after reaction finishes, cooling, liquid separation, spin-dried organic phase, silica gel column chromatography (CH 2 Cl 2 :CH 3O...

Embodiment 2

[0042] Embodiment 2: the preparation of catalyst

[0043] 1.5,5'-dibromo-2,2'-diphenol (3.44g, 10mmol), 3-chloromethylpyridine hydrochloride (3.04g, 20mmol), K 2 CO 3 (20.7g, 150mmol), KI (0.80g, 4.8mmol), DMF 25mL, stirred at room temperature for 24h, the reactant was poured into water, suction filtered, and the filter cake was subjected to silica gel column chromatography (CH 2 Cl 2 :CH 3 OH=25:1), to obtain white solid intermediate B4.12g, yield 78.3%.

[0044] 2.N 2 Under protection, intermediate B (5.26g, 10mmol), pyridine-4-boronic acid (2.46g, 20mmol), K 2 CO 3 (20.7g, 150mmol), placed in a 250mL three-necked flask, toluene, ethanol and water as solvent, adding catalyst Pd (PPh 3 ) 4 (1.2g, 1mmol), heat to reflux, control the temperature at 90°C-110°C, and control the reflux time at 36h. TLC tracking, left standstill after reaction finishes, cooling, liquid separation, spin-dried organic phase, silica gel column chromatography (CH 2 Cl 2 :CH 3 OH=20:1), to o...

Embodiment 3

[0045] Embodiment 3: Cu(NO 3 ) 2 Oxidation of water under hydrothermal to produce hydrogen peroxide

[0046] With catalyst ligand L 5.22mg (0.01mmol) prepared due to embodiment 1, Cu(NO 3 ) 2 ·6H 2 O 12.0mg (0.04mmol), water 2mL, sealed in a 10cm glass tube, programmed to heat up to 150°C after 300min, keep the temperature for 4320min, and then drop to 30°C after 3000min to obtain a yellow monovalent copper salt polymer and A solution containing hydrogen peroxide.

[0047] image 3 as a catalyst with Cu(NO 3 ) 2 The solution obtained by catalytic oxidation of water is added to the EPR signal measured by the hydroxyl radical scavenger DMPO, thus it can be concluded that the water is oxidized to hydrogen peroxide and partially produces hydroxyl radicals.

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Abstract

The invention discloses a biphenyl compound, a synthetic method and an application of the biphenyl compound, wherein a specific synthetic route of the compound (with a structural formula shown as follows) comprises the following steps: using 2,2'-dihydroxybiphenyl as raw material, performing bromination and etherification, and subjecting to column chromatography to obtain an intermediate B, and then subjecting the intermediate B to Suzuki coupling reaction and column chromatography to obtain a catalyst, wherein the catalyst together with metal copper salt can catalyze oxidized water to produce hydrogen peroxide under a hydrothermal condition. According to the synthetic method provided by the invention, a hydrothermal cleaning production technique is adopted, only pure water is used as solvent without addition of organic solvent, so poisonous waste gas does not be produced, intermediate product doesn't need to be sepearated, and the technical process is shortened.

Description

technical field [0001] The invention relates to a biphenyl compound and its synthesis method and application. Background technique [0002] Hydrogen peroxide is widely used in medicine, military industry and industry, and with the continuous expansion of urbanization scale, pollution sources containing high-concentration organic wastewater are increasing, and the degradation technology of organic pollutants has become the first choice to effectively solve the problem of sewage treatment At present, the treatment of organic pollutants with hydrogen peroxide has become an effective means of wastewater treatment. The reason is that the hydroxyl radical (OH) obtained by the decomposition of hydrogen peroxide has a very high oxidation potential (2.8V), and its oxidation ability is extremely strong. Some organic pollutants can undergo a rapid chain reaction to oxidize harmful substances into CO 2 、H 2 O or mineral salt, no secondary pollution. At present, the technologies for p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/30B01J31/28C01B15/01
Inventor 董育斌马建平于洋
Owner SHANDONG NORMAL UNIV
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