Process for the preparation of cyclohexanol and cyclohexanone
A technology of cyclohexanol and cyclohexanone, which is used in the preparation of hydroxyl addition, oxidation reaction, preparation of carbon-based compounds, etc.
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Embodiment 1
[0080] Partial hydrogenation of benzene
[0081] To a mixture of 80 ml benzene and 320 ml water in a titanium autoclave, 0.4 g ruthenium / zinc hydrogenation catalyst was added along with 14.4 g ZnSO 4 ·7H 2 O and 2g ZrO 2 . This mixture was stirred at 1500 rpm and heated to 145° C. under a hydrogen atmosphere of 5 MPa. After 65 minutes, the reaction mixture was cooled to room temperature. Analysis of the organic layer by gas chromatography indicated that the resulting mixture of benzene, cyclohexene and cyclohexane contained less than 0.05% impurities and had a benzene / cyclohexene / cyclohexane molar ratio of 29.9 / 54.8 / 15.2. At a conversion of benzene of 70.1%, a yield of cyclohexane of 15.2% and a yield of cyclohexene of 54.8% were obtained.
Embodiment 2
[0083] Oxidation of mixtures of benzene, cyclohexene and cyclohexane
[0084] A mixture of 54ml of benzene, cyclohexene and cyclohexane (the molar ratio is 29.9 / 54.8 / 15.2) and 80ml of 3% aqueous sulfuric acid, 40ml of acetonitrile, 199mg of Pd(NO 3 ) 2 , 746mgCuSO 4 and 6.99g H 3 PMo 12 o 40 Add to autoclave. At a temperature of 80°C, under a pressure of 5MPa, at 80NI per hour of N 2 5%O in 2 The reaction mixture was stirred at 1500 rpm under a constant flow of . After 8 hours, the reaction mixture was cooled to room temperature. Gas chromatographic analysis of the product showed the presence of 29.9 mol% benzene, 3.6 mol% cyclohexene, 15.2 mol% cyclohexane, 50.1 mol% cyclohexanone, 0.5 mol% cyclohexanol and 0.6 mol% C6 impurities.
[0085] At a conversion of cyclohexene of 93.4%, a selectivity of cyclohexanol and cyclohexanone of 98.8% was obtained.
Embodiment 3
[0087] Hydrogenation of Benzene / Cyclohexene / Cyclohexane Mixtures
[0088] Into a tubular hydrogenation reactor containing 50 ml of a platinum catalyst (0.3 wt% Pt) supported on alumina, 100 g of a mixture containing 61.4 g of benzene, 7.4 g of cyclic hydrogen, and 300 NI of hydrogen were fed per hour. Hexene and 31.2 g cyclohexane. The hydrogenation reaction is carried out at a pressure of about 3.0 MPa. The heat of reaction was removed by cooling the reactor with oil to about 225°C, with a maximum temperature in the reactor of 370°C. All organic compounds were condensed and gas chromatographic analysis showed that the impurity content in cyclohexane was less than 0.03 wt%.
[0089] This indicates a hydrogenation selectivity to cyclohexane of at least 99.9%.
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