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Photodissociation reaction method of benzothiophene compound for oxidative desulfurization

A technology of benzothiophene and oxidative desulfurization, which is applied in the petroleum industry, processing hydrocarbon oil, refining hydrocarbon oil, etc., can solve the problem of C-S bonds being difficult to break, and achieve the effect of reducing the loss of hydrocarbons

Active Publication Date: 2015-01-14
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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  • Photodissociation reaction method of benzothiophene compound for oxidative desulfurization
  • Photodissociation reaction method of benzothiophene compound for oxidative desulfurization
  • Photodissociation reaction method of benzothiophene compound for oxidative desulfurization

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Effect test

Embodiment 1

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

[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 center port, a lamp 2 is arranged in the U-shaped area of ​​the condenser tube, and a light switch 5 controls the on and off of the lamp 2 . In the three-port ...

Embodiment 2

[0044] Weigh 30mg 4,6-dimethyldibenzothiophene (DMDBT), 5mg o-chlorotetraphenylporphyrin iron, dissolve in 30mL methanol solution, slowly add 1.81g 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 maintained at 36°C with cooling water. Detected by high performance liquid chromatography, 100% conversion of 4,6-dimethyldibenzothiophene was detected. After column separation and NMR detection, the conversion rate of 4,6-dimethyldibenzothiophene CS bond cleavage was 93.27. %.

Embodiment 3

[0046] Weigh 30 mg of dibenzothiophene (DBT), 5 mg of iron phthalocyanine (that is, M=Fe, R in general formula (I) 1 =R 2 =R 3 =H,), dissolved in 30mL methanol solution, slowly dripped 0.72mg TBHP into the reaction mixture, the mixture was stirred and reacted under the irradiation of 250w high pressure mercury lamp for 2.5 hours, and the reaction temperature was kept at 25°C by circulating cooling water. After chromatographic column separation and nuclear magnetic resonance detection, the conversion rate of dibenzothiophene C-S bond cleavage in the reaction product was 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 an oxidation photolysis reaction method for benzothiophene compounds. Background technique [0002] Sulfur-containing petroleum products will release SO upon combustion x Compounds that cause harm to the environment. With the increasingly strict 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, has great resistance to hydrodesulfurization. To achieve the deep desulfurization effect, more severe conditions and special catalysts are required. A mild and economical catalytic hydrodesulfurization method is under urgent research. Fan Yu et al 1 Invented a technology for preparing a reverse microemulsion nuclear hydrogenation catalyst. The catalys...

Claims

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Application Information

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IPC IPC(8): C10G32/00
CPCC10G32/00C10G2300/202
Inventor 周新锐袁丰伊斯特万·马科孙凯于春冕
Owner DALIAN UNIV OF TECH
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