Method for synthesis of niobe oil by catalyzing bromobenzene with cobalt salt in light acceleration

A methyl benzoate and light-promoted technology, which is applied in the direction of carbon monoxide or formate reaction preparation, organic chemistry, etc., can solve the problems of low yield and poor selectivity of methyl benzoate, and achieve high yield and selectivity High, high value-added, small-scale effects

Inactive Publication Date: 2012-05-30
DALIAN UNIV
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  • Abstract
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Problems solved by technology

Daniel Cash, Angela Combs, Veljko Dragojlovic. Cobalt-catalyzed Photolytic Methoxycarbonylation of Bromoalkanes in the Presence of a Lewis Acid[J]. acac) 2 As a catalyst, bromobenzene is carried out to light carbonylation, and the yield of methyl benzoate is very low, and the selectivity is very poor

Method used

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  • Method for synthesis of niobe oil by catalyzing bromobenzene with cobalt salt in light acceleration

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Embodiment 1

[0018] Place a 400W high-pressure mercury lamp inside a hollow interlayer quartz photoreactor, pass circulating water into the interlayer, and put the entire reactor into a water tank filled with water to cool the light source; will contain 100mmol / L bromobenzene, 10mmol / L Catalyst Co(OAc) 2 , 200mmol / L alkaline additive NaOCH 3 Add 5mL of methanol solution into the quartz test tube, put the quartz test tube close to the outer wall of the photoreactor, pass carbon monoxide into the reaction solution, replace the deoxygenation, and keep the constant pressure at 0.1MPa at room temperature, start the light source to irradiate the reaction solution for 5h, the obtained product is Decane was used as internal standard, and the product was analyzed by GC and GC-MS. The yield of methyl benzoate calculated by GC was 47%, and the selectivity was 47%.

Embodiment 2

[0020] Place a 400W high-pressure mercury lamp inside a hollow interlayer quartz photoreactor, pass circulating water into the interlayer, and put the entire reactor into a water tank filled with water to cool the light source; will contain 100mmol / L bromobenzene, 10mmol / L Catalyst Co(OAc) 2 , 200mmol / L alkaline additive NaOCH 3 Add 5mL of methanol solution of 340mmol / L acetophenone into the quartz test tube, put the quartz test tube close to the outer wall of the photoreactor, pass carbon monoxide into the reaction solution, replace and remove oxygen, and keep the pressure at room temperature at a constant pressure of 0.1MPa to start the light source irradiation reaction In solution 5h, the obtained product was analyzed by GC and GC-MS with n-decane as internal standard. The yield of methyl benzoate calculated by GC was 91%, and the selectivity was 91%.

Embodiment 3

[0022] Place a 400W high-pressure mercury lamp inside a hollow interlayer quartz photoreactor, pass circulating water into the interlayer, and put the entire reactor into a water tank filled with water to cool the light source; will contain 100mmol / L bromobenzene, 10mmol / L Catalyst Co(OAc) 2 , 900mmol / L alkaline additive NaOAc and 5mL methanol solution of 340mmol / L acetophenone were added into the quartz test tube, and the quartz test tube was placed close to the outer wall of the photoreactor. The pressure was kept constant at 0.1 MPa, and the light source was turned on to irradiate the reaction solution for 5 hours. The obtained product was analyzed by GC and GC-MS with n-decane as internal standard. The yield of methyl benzoate calculated by GC was 72%, and the selectivity was 75%.

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Abstract

The invention relates to synthesis of methyl benzoate, in particular to a synthesis method of methyl benzoate by carbonylation of bromobenzene catalyzed by non-noble metal through photochemical catalysis under mild condition. The method adopts the technical proposal comprising the following steps: filling 0.10-0.15 Mpa CO into a solution consisting of 50-200 mmol / L of bromobenzene, 5-20 mmol / L ofCo(OAc)2 or CoCl2 as a catalyst and 100-1,000 mmol / l of alkali additive NaOCH3 or NaOAc, irradiating the solution by a 100-400W high voltage mercury lamp for 1-5 hours, and reacting at a temperature of between 15 and 25 DEG C. Preferably the methanol solution consisting of 50-200 mmol / L of bromobenzene, 5-20 mmol / L of Co(OAc)2 or CoCl2 as a catalyst and 100-1,000 mmol / l of alkali additive NaOCH3 or NaOAc is further added with 50-500 mmol / L of hypnone or benzophenone. The synthesis method has mild reaction condition, catalyzes reaction by simple non-noble metal salt, directly functionalizes bromobenzene, has high yield and selectivity (both can reach 91 percent) of the methyl benzoate, and is suitable for small scale production of methyl benzoate with high added value.

Description

technical field [0001] The invention relates to the synthesis of methyl benzoate, in particular to a method for synthesizing methyl benzoate by light-promoted carbonylation reaction of bromobenzene under mild conditions under non-noble metal catalysis. Background technique [0002] Methyl benzoate is an important organic fragrance and solvent, and one of its synthetic methods is the carbonylation reaction of halobenzene. However, most conventional carbonylation reactions require noble metal catalysts or high temperature and high pressure conditions. Although a few carbonylation reactions can be completed under mild conditions without noble metal catalysis, the catalysts used are still expensive and difficult to store. [0003] In recent years, the light-promoted carbonylation of benzene halides has attracted people's attention. Daniel Cash, Angela Combs, Veljko Dragojlovic. Cobalt-catalyzed Photolytic Methoxycarbonylation of Bromoalkanes in the Presence of a Lewis Acid[J]. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/76C07C67/36
Inventor 贾颖萍牟立茁尹静梅崔颖娜周广运高大彬
Owner DALIAN UNIV
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