Method for synthesizing cyclohexenone from cyclohexene

A technology of cyclohexenone and cyclohexene, which is applied in the field of synthesizing cyclohexenone, can solve the problems of low yield, environmental pollution, high cost, etc., and achieve the effects of low consumption, cost reduction, and increased production capacity

Active Publication Date: 2012-05-09
JIANGSU YANGNONG CHEM GROUP +1
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  • Abstract
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Problems solved by technology

However, since porphyrin derivatives are relatively complex organic compounds, their synthesis cost is high, th

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] In a 1 L autoclave, copper acetate and cyclohexene were sequentially added, and the dosage is shown in Table 1.

[0019] substance molecular weight Amount of substance / mol Mass / g Volume / mL Cyclohexene 82 1 82 101 copper acetate 200 0.5×10 －3 0.1 －

[0020] Inflate air to pressurize to 0.2MPa, heat to 120°C, react for 6 hours and then cool. A small amount of the reaction solution was analyzed by gas chromatography, and the gas chromatography analysis showed that the conversion rate was 24.1%, and the selectivity was 83.6%. The remaining reaction liquid was recovered unreacted cyclohexene by atmospheric distillation, and the residual liquid was distilled under reduced pressure (77~79°C, 2.66kPa) to obtain 17.2 g of cyclohexenone.

Embodiment 2

[0022] Use other copper compounds to replace copper acetate as the catalyst, and other conditions are the same as in Example 1 (the amount of catalyst used is 0.5×10 －3 mol, the molar ratio of each component in the composite catalyst is marked in brackets), and the results are shown in Table 2.

[0023] serial number catalyst Conversion rate / % selectivity / % 1 copper trifluoroacetate 19.2 76.8 2 copper sulfate 13.2 65.3 3 Copper oxide 12.0 77.6 4 Copper chloride 19.8 72.2 5 copper bromide 6.5 53.2 6 Copper acetate (90%) - copper oxide (10%) 23.3 82.1 7 Copper acetate (70%) - copper oxide (30%) 20.1 81.0 8 Copper acetate (50%) - copper oxide (50%) 17.8 80.7 9 Copper acetate (30%) - copper oxide (70%) 15.3 79.2 10 Copper acetate (10%) - copper oxide (90%) 14.6 78.2 11 Copper acetate (50%)-copper sulfate (50%) 20.0 80.9 12 Copper oxide (50%) - copper chloride (50%) 18.8 8...

Embodiment 3

[0026] Change the consumption of catalyzer copper acetate, other conditions are with embodiment 1, and the results are shown in Table 3.

[0027] Catalyst dosage / mol% 0.01 0.1 0.2 0.5 1.0 Conversion rate / % 13.6 24.6 18.7 17.2 18.0 selectivity / % 74.2 73.5 74.4 63.4 52.2

[0028] The above results show that the best catalyst dosage is 0.01mol%~0.5mol%, and the increase of catalyst dosage will significantly reduce the selectivity.

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Abstract

The invention provides a method for preparing cyclohexenone through oxidizing cyclohexene with molecular oxygen. According to the method, the cyclohexenone is prepared by taking reaction at 0.1 to 1.0MPa and 80 to 160 DEG C through using easy-to-obtain cyclohexene as raw materials and using oxygen or air as oxygen sources under the existence of copper compound catalysts such as copper acetate, copper trifluoroacetate, copper sulfate, copper oxide, copper chloride, copper bromide and the like. According to the method, low-price clean oxidizing agents are adopted, the addition of solvents is not needed, the catalysts are simple and are easy to obtain, the conversion rate and the selectivity are high, the production cost is low, and the method is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing cyclohexenone, in particular to a green method for preparing cyclohexenone by oxidizing cyclohexene with molecular oxygen. Background technique [0002] Cyclohexenone, the allylic oxidation product of cyclohexene, is a very important chemical intermediate and is widely used in the fields of pesticide and pharmaceutical production, such as cyclohexenone herbicides. The earlier synthesis method of cyclohexenone was obtained by oxidizing cyclohexene with chromic acid (anhydride) in glacial acetic acid solvent. This method has low yield, difficult separation and serious pollution, making it difficult to realize industrialization. [0003] Molecular oxygen is a cheap and clean oxidizing agent. The preparation of cyclohexenone by oxidizing cyclohexene with molecular oxygen has the advantages of low cost, cleanliness, and high atom economy. Therefore, people have developed a series of new processes for the ...

Claims

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Application Information

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IPC IPC(8): C07C49/603C07C45/34
Inventor 俞磊顾志强丁克鸿易容王根林倪世春董海妹
Owner JIANGSU YANGNONG CHEM GROUP
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