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Preparation method of cyclohexanol through dehydrogenation with coupling of cyclohexane mixture

A cyclohexane and mixture technology, applied in the field of cyclohexanol preparation, can solve the problems of high energy consumption, large equipment investment, complex process flow, etc.

Active Publication Date: 2020-03-10
南京匹亚化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Obviously, the main disadvantages of this industrial method are: (1) energy consumption is very high, and more than 10 tons of steam are needed to produce 1 ton of cyclohexanol; (2) the process is more complicated and the investment in equipment is large; (3) it needs to be developed The market or utilization of cyclohexane. For example, some companies have planned to invest in the construction of cyclohexanol and cyclohexanone production equipment for the oxidation of cyclohexane to solve the problem of cyclohexane sales.

Method used

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  • Preparation method of cyclohexanol through dehydrogenation with coupling of cyclohexane mixture
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  • Preparation method of cyclohexanol through dehydrogenation with coupling of cyclohexane mixture

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preparation example Construction

[0062] The preparation process of the dehydrogenation catalyst is as follows: use a certain amount of deionized water to dissolve the magnesium nitrate and aluminum nitrate metal salts required for the hydrotalcite, and the nickel nitrate and stannous chloride metal salts required for the transition metal active component, using urea As an alkaline co-precipitation reagent, the initial pH of the mixed solution was measured to be about 3. Stir at 90-120°C for 5-20 hours, age the stirred mixed solution in a water bath at 25°C for 5-30 hours, and dry overnight at 80-120°C. The prepared hydrotalcite precursor is placed in a muffle furnace and calcined at 500-900° C. for 2-5 hours to obtain the Mg-Al-O composite oxide containing tin and nickel. The catalyst is reduced in a hydrogen stream at 300-600°C for 4 to 9 hours to obtain the dehydrogenation catalyst used in the process of the present invention, wherein the mass percentage of nickel is 5 to 40 wt%, and the mass percentage of ...

Embodiment 1

[0065] The preparation process of dehydrogenation catalyst C-1 is as follows: Dissolve 76.92 g of magnesium nitrate and 37.52 g of aluminum nitrate metal salt required for forming hydrotalcite with 350 ml of deionized water, and nickel nitrate required for introducing transition metal active components 8.6g and 2.5g of stannous chloride metal salt required for introducing main group metal components, adopt urea as alkaline co-precipitation reagent, the consumption of urea makes the initial pH of the mixed solution measured is about 3. Stirring at 100°C for 12 hours, the stirred mixed solution was aged in a water bath at 25°C for 20 hours, then filtered, and the filter cake was dried overnight at 105°C. The prepared dry hydrotalcite-based precursor was placed in a muffle furnace and calcined at 800°C for 3 hours to obtain a Mg-Al-O composite oxide containing tin and nickel. The catalyst was reduced in a hydrogen stream at 500°C for 6 hours to obtain the flake or layered catalys...

Embodiment 2

[0068] Example 1 was essentially repeated. The difference is that the reaction mixture obtained from the partial hydrogenation step of benzene (a mixture of benzene, cyclohexene and cyclohexane with 0.451 mole fractions of benzene, 0.122 mole fractions of cyclohexane, and The mole fraction is 0.427, based on the total molar weight of benzene, cyclohexane and cyclohexene), by selecting solid sulfonic acid resin as catalyst, first carry out addition reaction with formic acid, the temperature of addition reaction is 120 ℃, the reaction pressure 0.3 MPa to obtain a reaction mixture containing cyclohexyl formate, wherein the yield of ester was 99%. Then the resulting reaction mixture containing cyclohexyl formate was hydrolyzed by reactive distillation at 110°C, and separated during the reaction to obtain cyclohexanol, formic acid and light components respectively, of which cyclohexanol was The rate is 98.1%. The obtained light component is a mixture containing cyclohexene, cyclo...

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Abstract

A preparation method of cyclohexanol through dehydrogenation with coupling of cyclohexane mixture includes steps of: 1) performing partial hydrogenation on benzene with hydrogen to obtain a cyclohexene crude product containing benzene and cyclohexane; 2) performing direct cyclohexene hydration reaction on the cyclohexene crude product and separating a cyclohexanol product, as a heavy component, from the hydration reaction mixture in order to obtain a light component including benzene, cyclohexane and cyclohexene; 3) performing catalytic dehydrogenation on the light component in the presence ofa dehydrogenation catalyst to obtain benzene and hydrogen. The invention further provides a hydrotalcite based or a hydrotalcite-like based transition metal simple substance composite catalyst used in the dehydrogenation reaction of the alicyclic hydrocarbons. The method is free of extractive rectification for separating the benzene and the cyclohexane and is free of an extractive rectification extract agent. After the dehydrogenation of the cyclohexane, the generated benzene and hydrogen are recycled, so that the problem of marketing of the cyclohexane is solved and unit hydrogen consumptionof the cyclohexanol is reduced.

Description

technical field [0001] The invention relates to a method for preparing cyclohexanol coupled with the dehydrogenation technology of cyclohexane mixture. Background technique [0002] Cyclohexanol has a wide range of uses, especially as the main intermediate for the preparation of caprolactam and adipic acid, and is also an important raw material for the preparation of various vinyl resin paints. At the same time, due to its high solubility and low volatility, it is suitable for Polymers such as nitrocellulose and cellulose are ideal solvents. [0003] The traditional cyclohexanol production process mainly includes the following two methods: phenol hydrogenation method and cyclohexane liquid phase oxidation method. Phenol hydrogenation is a one-step reaction of phenol and hydrogen to prepare cyclohexanol. However, due to the high price of phenol, the use of noble metal catalysts is currently required, so the high cost greatly limits its industrial application. Cyclohexane ox...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/04C07C35/08B01J23/835
CPCC07C29/04C07C5/11C07C5/324B01J23/835C07C2601/14C07C2601/16C07C2523/835C07C35/08C07C13/20C07C15/04Y02P20/10
Inventor 罗和安游奎一张智敏陈文凯
Owner 南京匹亚化工有限公司
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