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A photolysis reaction method of benzothiophene compounds for oxidative desulfurization

A technology of benzothiophene and compounds, which is applied in the field of oxidative photolysis reaction of benzothiophene compounds, can solve problems such as the difficulty of breaking C-S bonds, and achieve the effect of reducing the loss of hydrocarbons

Active Publication Date: 2017-04-12
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of the problem that the C-S bond is difficult to break in the current oxidative cleavage of benzothiophene and its derivatives, the purpose of the present invention is to provide a new method for oxidative cleavage of the C-S bond of benzothiophene compounds under mild conditions

Method used

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  • A photolysis reaction method of benzothiophene compounds for oxidative desulfurization
  • A photolysis reaction method of benzothiophene compounds for oxidative desulfurization
  • A photolysis reaction method of benzothiophene compounds for oxidative desulfurization

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Experimental program
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Effect test

Embodiment 1

[0040] Weigh 30mg (0.15mmol) dibenzothiophene (DBT), 5mg o-chlorotetraphenylporphyrin iron (i.e. M=Fe in general formula (II), R 1 =Cl,R 2 =R 3 =H,Y 1 =Y 2 =Y 3 =Y 4 =C m , m=0), was dissolved in 30mL of methanol solution, slowly added dropwise 54mg (0.9mmol) of tert-butanol peroxide (TBHP) in the reaction mixture, and the mixture was stirred and reacted under the irradiation of a 250w high-pressure mercury lamp for 2.5 Hours, the reaction temperature was maintained at 36°C with cooling water circulation. The conversion rate of dibenzothiophene C-S bond breaking in the reaction product was 95.21% through chromatographic column separation and nuclear magnetic resonance detection.

[0041] The above reaction preferably adopts such as figure 1 It is carried out in the reaction device shown, specifically: a three-port reactor 1, a U-shaped condenser tube 3 is installed from the central port, and a lamp 2 is installed in the U-shaped area of ​​the condenser tube, and the la...

Embodiment 2

[0044] Weigh 30 mg of 4,6-dimethyldibenzothiophene (DMDBT), 5 mg of ferric o-chlorotetraphenylporphyrin, dissolve in 30 mL of methanol solution, slowly add 1.81 g of H 2 o 2 (30% aqueous solution) in the reaction mixture, the mixture was stirred and reacted for 2.5 hours under the irradiation of a 250w high-pressure mercury lamp, and the reaction temperature was kept at 36° C. with cooling water. Detected by high performance liquid chromatography, 100% conversion of 4,6-dimethyldibenzothiophene was detected, and the conversion rate of C-S bond breaking of 4,6-dimethyldibenzothiophene was 93.27% through chromatographic column separation and nuclear magnetic resonance detection %.

Embodiment 3

[0046] Take by weighing 30mg dibenzothiophene (DBT), 5mg iron phthalocyanine (being M=Fe in the general formula (I), R 1 =R 2 =R 3 =H,), dissolved in 30mL methanol solution, slowly added dropwise 0.72mg TBHP into the reaction mixture, the mixture was stirred and reacted for 2.5 hours under the irradiation of a 250w high-pressure mercury lamp, and the reaction temperature was kept at 25°C by circulating cooling water. Through chromatographic column separation and nuclear magnetic resonance detection, the conversion rate of dibenzothiophene C-S bond breaking in the reaction product is 67.20%.

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Abstract

The invention discloses a photodissociation method of a benzothiophene compound for oxidative desulfurization. According to the method, the benzothiophene compound reaches C-S bond fracture reaction under the existence of an oxidizing agent and metal phthalocyanine or metalloporphyrin through illuminating reaction. According to the method disclosed by the invention, under the mild conditions of normal temperature and pressure, the most stable sulfide, namely the benzothiophene compound in an oxidized petroleum product reaches the C-S bond oxidation fracture in the benzothiophene compound, so as to obtain a sulfocompound with relatively strong polarity and sulfur-free hydrocarbon oxide. The conversion ratio of the C-S bond fracture reaches over 90% when metalloporphyrin is a catalyst, and the problems that the C-S bond oxidation fracture reaction in the benzothiophene compound at present needs high temperature, high pressure and a special catalyst, and is high in demands on equipment, and low in productive rate are overcome.

Description

technical field [0001] The invention relates to a photolysis reaction method for oxidative desulfurization, in particular to a photolysis reaction method for benzothiophene compounds. Background technique [0002] Sulfur-containing petroleum products release SO after combustion x compounds that are harmful to the environment. With the increasingly stringent and standardized environmental protection regulations, deep desulfurization of petroleum products is receiving widespread attention. The traditional industrial desulfurization method is hydrodesulfurization (HDS). However, benzothiophene, especially dibenzothiophene, is very resistant to HDS. To achieve deep desulfurization effect, more stringent conditions and special catalysts are required. A mild and economical catalytic hydrodesulfurization method is urgently being studied. Fan Yu and others 1 Invented the preparation technology of inverse microemulsion nuclear hydrogenation catalyst, the catalyst exhibited excell...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C10G32/00
CPCC10G32/00C10G2300/202
Inventor 周新锐马小锋伊斯特万·马科袁丰孙凯于春冕
Owner DALIAN UNIV OF TECH
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