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Aerobic oxidation system containing sulfinic acid, sulfonic acid or derivative thereof and photo-catalytic oxidation method thereof

A technology of aerobic oxidation and derivatives, which is applied in the fields of chemical technology, materials and biomedicine, can solve problems such as limited application, environmental pollution, and inability of products to stay, and achieve reduced production costs, energy consumption, equipment investment, and overall The effect of reducing operating costs

Active Publication Date: 2020-08-11
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the one hand, strong oxidants generally have many problems in terms of storage, operation, cost, and environmental protection; on the other hand, due to the use of strong oxidants, the product cannot stay in a relatively active intermediate oxidation state, which limits the application of such methods
In terms of post-reaction treatment, a large amount of water washing is usually required, and these wastewaters contain a large amount of heavy metal ions, which will cause serious environmental pollution problems

Method used

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  • Aerobic oxidation system containing sulfinic acid, sulfonic acid or derivative thereof and photo-catalytic oxidation method thereof
  • Aerobic oxidation system containing sulfinic acid, sulfonic acid or derivative thereof and photo-catalytic oxidation method thereof
  • Aerobic oxidation system containing sulfinic acid, sulfonic acid or derivative thereof and photo-catalytic oxidation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0284] The reactant toluene (0.2mmol) and the auxiliary agent sodium trifluoromethanesulfinate (0.5eq) were dissolved in the organic solvent anhydrous CH 3 CN (2mL) to obtain the reaction mixture, the reaction mixture is placed in a reaction tube containing a magnetic stirrer, and then the reaction tube is placed under 34W CFL or blue light (wavelength is 400-455nm) (wherein the reaction mixture The liquid is placed under the reaction light source), and the light reaction is carried out at room temperature, air or oxygen atmosphere (1atm) until the reaction is complete (about 12h). After the reaction was completed, the reaction mixture was concentrated under reduced pressure to obtain the crude product of the target compound, which was separated by column chromatography to obtain the target compound benzaldehyde or quantified by GC-MS (yield 23%).

[0285] The characterization results are: 1 H NMR (800MHz, CDCl 3 )δ10.03(s, 1H), 7.89(d, J=7.0Hz, 2H), 7.64(t, J=8.5Hz, 1H), 7....

Embodiment 2

[0289] Example 2 adopts the same method as Example 1, the difference is only the auxiliary agent, which is specifically listed in Table 1a.

[0290] The specific reaction conditions of table 1a embodiment 2

[0291]

[0292]

Embodiment 2a-2q

[0294] Embodiment 2a-2q adopts the same method of embodiment 1 (the time of each reaction is about more than 8 hours and can last to 12 hours or longer), and the difference is only the reactants and light conditions (wavelength of the light source), specifically listed in Table 1b.

[0295] The specific reaction conditions of table 1b embodiment 2a-2q (molecular oxygen species is O 2 )

[0296]

[0297] The characterization results for Examples 2a, 2b, 2d and 2e are listed in Table 1c.

[0298] Table 1c Characterization data for Examples 2a, 2b, 2d and 2e

[0299]

[0300] The reaction formula of embodiment 2c is as follows:

[0301]

[0302] The reaction formula of embodiment 2d is as follows:

[0303]

[0304] The reaction formula of embodiment 2e is as follows:

[0305]

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Abstract

The invention relates to an aerobic oxidation system and a photoinduced aerobic oxidation method thereof. The aerobic oxidation system comprises 1) at least one of the following substances 1a)-1d): 1a) sulfinic acid or a derivative thereof; 1b) sulfonic acid or a derivative thereof; 1c) a compound or mixture that can produce sulfinic acid or a derivative thereof by reaction; 1d) a compound or mixture that can produce sulfonic acid or a derivative thereof by reaction; and 2) a molecular oxygen-containing component comprising at least one of oxygen, an oxygen-containing gas and a raw material ofa reaction system capable of generating oxygen molecules in situ. When the aerobic oxidation system is used for an oxidation method, a series of compounds can be subjected to aerobic oxidation at room temperature without adding a photosensitization reagent under an illumination condition to obtain corresponding oxidation products so that the production cost is reduced; in addition, the method cangreatly reduce energy consumption, and thoroughly solves the problem of environmental pollution caused by waste discharge brought by heavy metals and acidic solvents, and the problem of metal residues in the product.

Description

technical field [0001] The invention belongs to the fields of chemical technology, materials and biomedicine, and specifically relates to an aerobic oxidation system containing sulfinic acid, sulfonic acid or derivatives thereof and a photocatalytic oxidation method thereof. Background technique [0002] Oxidation reactions are the most basic and extremely important reactions in nature, among which the selective oxidation of organic compounds is an important part of modern synthetic chemistry and oxidation reactions. [0003] Over the past few decades, direct oxidation of C–H and C–C bonds in organic compounds to functionalize them has proven to be the most straightforward and efficient method for the synthesis of complex products from simple, readily available starting materials. Molecular oxygen has attracted much attention as a green, environmentally friendly and sustainable mild oxidant due to its rich content, high atom economy and environmental friendliness. Therefore...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B33/00C07C37/07C07C39/14C07C41/56C07C43/307C07C45/32C07C45/36C07C47/54C07C49/78C07C47/55C07C49/86C07C49/807C07C49/84C07C49/784C07C49/76C07C49/788C07C49/786C07C47/546C07C45/39C07C49/403C07C51/235C07C63/70C07C63/36C07C63/331C07C51/255C07C63/06C07C67/313C07C69/82C07C253/30C07C255/50C07C303/32C07C309/04C07C315/02C07C317/44C07C317/04C07D215/227C07F9/53
CPCC07B33/00C07C303/32C07C45/36C07C45/32C07C51/255C07C315/02C07F9/5304C07F9/5325C07C45/39C07C37/07C07C51/235C07C67/313C07C41/56C07C253/30C07D215/227C07C2601/14C07C309/04C07C47/54C07C49/78C07C47/55C07C49/86C07C49/807C07C49/84C07C49/784C07C49/76C07C49/788C07C63/06C07C317/14C07C317/04C07C49/786C07C47/546C07C49/403C07C39/14C07C63/70C07C63/36C07C63/331C07C69/82C07C43/307C07C255/50C07C317/44C07F9/53Y02B20/00
Inventor 付华朱先进
Owner TSINGHUA UNIV
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