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Photochemical process for olefin synthesis of oxygen-containing compound

A compound and photochemical technology, applied in the field of photooxidative synthesis, can solve the problems of low reaction efficiency, non-absorbing properties of colored complexes, etc., and achieve high selectivity

Inactive Publication Date: 2005-12-07
INST OF CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these biomimetic catalytic systems currently only have the properties of monooxygenases, that is, atomic oxygen such as hydrogen peroxide must be used to realize the catalytic cycle.
In addition, the article "Selective photooxidation of small alkenes by O 2 with red light in zeoliteY., Blatter F, Frei H., J.Am.Chem.Soc 1994, 116:1812-1820), Frei et al. used molecular sieves in shape-selective photochemical reactions and found that in the channels of NaY molecular sieves , the organic substrate and molecular oxygen will form a colored complex, which is excited by visible light to realize the electron transfer reaction between organic matter and molecular oxygen. Once the oxidation product is formed, it does not have the light-absorbing properties of the colored complex, and the reaction is automatic. Stop, to avoid excessive oxidation, so there is good selectivity, but the efficiency of the reaction is very low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add 3.5 ml of water (pH value 6.5), 1.5 ml of chloroform, and 100 microliters of styrene into a glass reactor, adjust the stirring speed to 30 rpm, mix well, seal it, and pour O 2 , O 2 Pressure is 0.08MPa, open medium-pressure mercury lamp (100W), carry out UV irradiation, stop reaction after 7 hours, reaction product is mainly benzaldehyde, and the selectivity of benzaldehyde is 95.0%, other products: phenylethylene glycol (C 6 h 5 CHOHCH 2 OH), benzoic acid, styrene oxide (C 6 h 5 CHCH 2 O) etc., total amount is less than 5%, and the productive rate of benzaldehyde reaches 11%.

Embodiment 2

[0021] Add 5 ml of water (PH value 6.5) and 50 microliters of 4-methoxystyrene into a glass reactor, adjust the stirring speed to 30 rpm, mix well, seal it, and pour O 2 , O 2 The pressure is 0.06MPa, turn on the medium pressure mercury lamp, carry out UV irradiation, stop the reaction after 12 hours, the reaction product is mainly 4-methoxybenzaldehyde, and the selectivity of 4-methoxybenzaldehyde is 98.0%, 4-methoxybenzaldehyde The yield of oxybenzaldehyde reaches 11%.

Embodiment 3

[0023] Add 5 ml of chloroform (pH value 7.0), H 2 o 2 30% 100 microliters, styrene 100 microliters, adjust the stirring speed to 30 rpm, mix evenly, turn on the medium pressure mercury lamp, carry out UV irradiation, stop the reaction after 7 hours, the reaction product is mainly benzaldehyde, benzaldehyde The selectivity is 90.0%, and the yield of benzaldehyde is 6%.

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Abstract

The invention discloses a photochemical process for olefin synthesis of oxygen-containing compound which comprises, inducing olefin with ultraviolet light / visible light, oxygenizing in water or the mixed medium of organic / water. The olefin includes alkenylene, annular olefin, aromatic hydrocarbon and substituted alkenylene, substituted annular olefin, or substituted aromatic hydrocarbon.

Description

technical field [0001] The invention relates to the technical field of photooxidative synthesis, in particular to a green photochemical oxidation technology for highly selective synthesis of oxygen-containing compounds. Background technique [0002] With the continuous development of world science and technology, environmental protection and sustainable development are getting more and more attention. In recent years, in the field of organic synthesis, green oxidation has attracted widespread attention as an environmentally friendly research direction. The so-called green oxidation refers to the oxidation reaction realized by using hydrogen peroxide or molecular oxygen as the oxidizing agent and using water or other non-toxic compounds as the solvent. It would be more ideal if the molecular oxygen dissolved in the solution could be activated by using clean solar energy under mild conditions to realize various oxidation processes with great application value and potential va...

Claims

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Application Information

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IPC IPC(8): C02F1/74
Inventor 赵进才任岩军马万红钱新华张士博
Owner INST OF CHEM CHINESE ACAD OF SCI
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