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Methods of preparing cyclohexanone and derivatives

A technology for cyclohexanone and oxides, which is applied in the field of preparing cyclohexanone and its derivatives, and can solve problems such as increased energy consumption and environmental problems

Inactive Publication Date: 2018-05-25
INTERNATIONAL FLAVORS & FRAGRANCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, a limitation of the conventional hydrogenation process is the moderate selectivity of cyclohexanone over cyclohexanol, etc.
In addition, the process often requires a solvent disposal step which can pose environmental concerns
Additionally, some processes involve steam for heating and result in increased energy consumption

Method used

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  • Methods of preparing cyclohexanone and derivatives
  • Methods of preparing cyclohexanone and derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1. Catalyst separation

[0051] Pd-γ-Al 2 o 3 Preparation: 0.143g of palladium acetylacetonate (Pd(acac) 2 ) was dissolved in 25mL of acetone, and the solution was impregnated into 1g of γ-Al at 40°C 2 o 3 . The resulting Pd-γ-Al 2 o 3 Contains 5% by weight of Pd. After impregnation, the catalyst was dried at 100°C for 2 hours and calcined in a muffle furnace at 450°C for 2 hours at a heating rate of 3.5°C / min.

[0052] Catalyst 1 : Dissolve 5 mL of 5.8 mg of Na by immersion at 80 °C 2 CO 3 The aqueous solution was introduced to 0.5 g of the catalyst Pd-γ-Al prepared above 2 o 3 . After drying the catalyst at 100 °C for 2 h, it was 2 Reduction was carried out at 150° C. for 2 hours under flow, thereby obtaining Catalyst 1 with 0.5% by weight Na.

[0053] Catalyst 2 : Dissolve 5 mL of 11.6 mg of Na by impregnation at 80°C 2 CO 3 The aqueous solution was introduced to 0.5 g of the catalyst Pd-γ-Al prepared above 2 o 3 . After drying the ca...

Embodiment 2

[0058] Example 2. Hydrogenation of p-tert-amylphenol using catalysts 1-6

[0059] The hydrogenation reaction was carried out in a strengthened glass reactor equipped with a pressure gauge to monitor the pressure in the reactor. 10.5 mg of one of the catalysts and 495 mg of p-tert-amylphenol were added to the reactor. The reactor is then purged with hydrogen, pressurized to 5 bar (dynamic pressure) with hydrogen, heated to 100° C., and maintained at this temperature for a period of time (eg, 10 to 16 hours). Quantitative analysis of the reaction mixture after filtration was carried out in GC-MS and GC-FID. Conversion was calculated as moles of p-tert-amylphenol converted / initial moles of the compound x 100%. The yield of the desired product Orivone or the by-product 4-tert-amylcyclohexanol was determined as the number of moles of the compound / the initial number of moles of p-tert-amylphenol×100%. The Orivone selectivity was calculated as the number of moles of Orivone / the nu...

Embodiment 3

[0063] Example 3. Utilization of Catalyst 2 (on γ-Al 2 o 3 5% Pd and 1% Na) hydrogenation of p-tert-amylphenol

[0064] The hydrogenation reaction is carried out in a reinforced glass reactor equipped with a pressure gauge. 10.5 mg of catalyst, 495 mg of p-tert-amylphenol and 500 mg of solvent (water or tetrahydrofuran (THF)) were introduced into the reactor, which was purged with hydrogen and pressurized with hydrogen at 5 bar (dynamic pressure), and finally The reactor was heated at 100°C. Quantitative analysis of the reaction mixture after filtration was carried out in GC-MS and GC-FID. Table 2 below lists the results obtained with Catalyst 2 carried out in the absence of solvent and compared with the case of using THF and water as solvent.

[0065] Table 2

[0066] solvent

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Abstract

The present invention provides a method of preparing an optionally substituted cyclohexanone comprising contacting an optionally substituted phenol and a catalyst in a hydrogen atmosphere. High yieldand selectivity are achieved in a substantially solvent free system.

Description

field of invention [0001] The present invention relates to novel p-substituted phenols useful for the preparation of cyclohexanone, in particular 4-tert-amylcyclohexanone ("Orivone"), by hydrogenation of 4-tert-amylphenol with good selectivity and high yield Hydrogenation method. Background of the invention [0002] Cyclohexanone and its derivatives have been employed in a variety of industrial processes and products. Cyclohexanone can be used, for example, as solvent or activator in oxidation reactions. It can also be used as an intermediate, for example, in the production of resins, caprolactam, adipic acid or nylon-6,6. Orivone (i.e., 4-tert-amylcyclohexanone), which is a derivative of cyclohexanone, is a fragrance compound widely used in the preparation of fragrance compositions or products, including soap, Detergents, cosmetic powders and washing liquids. [0003] Cyclohexanone and its derivatives such as Orivone have been prepared by catalytic hydrogenation of phen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/51C07C49/403B01J27/232B01J23/58
CPCC07C45/512B01J23/58B01J27/232C07C49/403C07C45/006
Inventor 弗朗西斯科·戈内尔·戈麦斯萨拉·伊沃拉·乔尔内特阿韦利诺·科马·卡尼奥斯埃斯特拉·埃斯皮诺斯·费里
Owner INTERNATIONAL FLAVORS & FRAGRANCES
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