Visible light stimulated oxidation process for transforming aryl substituted vicinal diol to hydroxyketone

An oxidation process, the technology of vicinal diol, which is applied in the field of environment-friendly technology, can solve the problems such as the inability to carry out oxidation conversion of alcohols and ketones, and achieve the effect of improving production efficiency and reducing production costs

Inactive Publication Date: 2014-08-13
陈婷 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the academic literature (such as M.S.Sigman, D.R.Jensen, Acc.Chem.Res.2006,39,221-229), although there are considerable reports of using air or oxygen as the terminal oxidant, due to the fact that air or oxygen itself cannot perform alcohol- Oxidative conversion of ketones, these systems must use oxidation catalysts such as metals (such as expensive Pd) without exception

Method used

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  • Visible light stimulated oxidation process for transforming aryl substituted vicinal diol to hydroxyketone
  • Visible light stimulated oxidation process for transforming aryl substituted vicinal diol to hydroxyketone
  • Visible light stimulated oxidation process for transforming aryl substituted vicinal diol to hydroxyketone

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Embodiment one: the light-promoted Br of hydroxy ketone product A 2 / H 2 o 2 catalytic oxidation synthesis

[0040] Dissolve 166 grams of 2-methyl-1-phenylpropane-1,2-diol in 2 liters of dichloromethane, add water to adjust the volume of the aqueous phase to about 1.4 liters, and place a fluorescent lamp outside the reaction glass flask ( External light source irradiation), add 32 grams of bromine (0.2 equivalents), then slowly add 113 grams of 30% hydrogen peroxide dropwise under rapid stirring (note cooling, keep the reaction temperature in the range of 10-25 degrees Celsius all the time. Unless special It is stated that all the following other examples are tested to maintain this temperature range), and the raw materials are all converted into product A by nuclear magnetic resonance (NMR) detection after 1 hour of light and stirring reaction.

[0041] Darkness contrast test: Dissolve 166 grams of 2-methyl-1-phenylpropane-1,2-diol in 2 liters of dichloromethane, ad...

Embodiment 2

[0043] Embodiment two: the light-promoted HBr / H of hydroxy ketone product B 2 o 2 catalytic oxidation synthesis

[0044] Dissolve 206 grams of 1-(hydroxyl (phenyl) methyl) cyclohexanol in 3 liters of dichloromethane, add water to adjust the volume of the aqueous phase to about 1.6 liters, suspend the LED lamp tube inside the reaction flask (built-in Light source irradiation, white light LED light source, the wavelength range is 395-550 nanometers), add 10% aqueous solution (0.4 equivalent) of 320 grams of HBr, then slowly add 113 grams of 30% hydrogen peroxide dropwise under rapid stirring, stir under light After 4 hours of reaction, the raw materials were all converted into product B by NMR detection.

[0045] Darkness contrast test: 206 grams of 1-(hydroxyl (phenyl) methyl) cyclohexanol was dissolved in 3 liters of dichloromethane, water was added to adjust the volume of the aqueous phase to about 1.6 liters, the LED lamp tube was removed and the reaction flask was Wrap t...

Embodiment 3

[0047] Embodiment three: the light-promoted NaBr / H of hydroxy ketone product A 2 SO 4 / H 2 o 2 catalytic oxidation synthesis

[0048] Dissolve 166 grams of 2-methyl-1-phenylpropane-1,2-diol in 2 liters of dichloromethane, and use an LED surface light source with an emission wavelength of 405 nm to irradiate (external light source irradiation, 22 cm long * 4 centimeters wide, power is 6 watts per square centimeter), adding successively a 40% aqueous solution and 25 grams of sulfuric acid containing 50 grams of sodium bromide (NaBr), adding water to adjust the volume of the aqueous phase to about 1 liter. 113 grams of 30% hydrogen peroxide was slowly added under rapid stirring, and the raw material was detected by nuclear magnetic resonance (NMR) to generate product A with a conversion rate of 96% after 2 hours of light and stirring reaction.

[0049] The above experiments clearly demonstrate that HBr generated from the in situ reaction of NaBr and acid can equally efficient...

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Abstract

The invention relates to the technical field of radiation-curing photopolymerization and discloses a method for preparing an aryl-substituted hydroxyketone compound through catalytic oxidation aryl substituted vicinal diol under the condition of light radiation. The method has no need of using heavy metal as a catalyst and has the characteristics of high production efficiency, low production cost, environment-friendliness and the like.

Description

technical field [0001] The invention relates to the technical field of radiation-curing photopolymerization, in particular to a new environment-friendly technology for transforming some aryl-substituted ortho-diol compounds into their corresponding aryl hydroxy ketones under the promotion of light conditions and the action of appropriate chemical oxidants. Background technique [0002] In the field of radiation (ultraviolet light or visible light or electron beam or X-ray) curing, photosensitive compounds that can generate free radical active species under irradiation conditions are one of the most important components of radiation curing formulations containing ethylenically unsaturated systems. Among them, hydroxyketone compounds have obtained the most extensive industrial applications due to their high initiating activity, good yellowing resistance, low price and easy availability. For example, the following three compounds are well-known by professionals in this industry....

Claims

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Application Information

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IPC IPC(8): C07C45/29C07C45/30C07C49/82C07C49/83C07C49/84
CPCC07C45/29C07C45/30C07C49/82C07C49/83C07C49/84
Inventor 陈婷王瑜
Owner 陈婷
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