Method of preparing cyclopentene by continuous hydrogenation of cyclopentadiene

A technology for producing cyclopentadiene and cyclopentene, which is applied in the fields of hydrogenation, organic chemistry, etc., can solve the problems of reducing the yield of cyclopentene, limitation of cooling uniformity, and overheating of the catalyst bed, and achieves easy reaction , The effect of increasing the reaction yield and uniform temperature

Inactive Publication Date: 2007-02-14
SINOPEC SHANGHAI PETROCHEMICAL CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the cyclopentadiene hydrogenation reaction is a strong exothermic reaction, the catalyst bed is prone to runaway temperature during the catalytic hydrogenation process, resulting in catalyst deactivation
In the prior art, the method of installing heat exchange devices in the hydrogenation reactor is mostly used to remove a large amount of reaction heat. The defect of thi

Method used

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  • Method of preparing cyclopentene by continuous hydrogenation of cyclopentadiene
  • Method of preparing cyclopentene by continuous hydrogenation of cyclopentadiene
  • Method of preparing cyclopentene by continuous hydrogenation of cyclopentadiene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～8

[0018] The process flow of each embodiment of the present invention is shown in the drawings. The reactor 1 is a fixed bed reactor, and a venturi ejector 2 is installed on the top of the reactor. The raw material cyclopentadiene M1, the solvent M2, and the external circulation reaction liquid M4 enter the raw material blending tank for mixing. The liquid phase material from the raw material blending tank and the raw material hydrogen M3 are fully mixed and atomized into a mist-like gas-liquid mixture in the Venturi injector 2 and then pass through the fixed-bed catalyst bed for hydrogenation reaction. The reaction liquid from the reactor enters the reaction liquid storage tank 4, and then passes through the external circulation heat exchanger for heat exchange and cooling. The cooled reaction liquid is divided into two parts, one is the external circulation part M4, the other is the discharge M5, M4 returns to the raw material blending tank 3, and M5 enters the product storage tan...

Embodiment 9

[0021] Except that methanol is used as the solvent, the rest are the same as in Examples 1-8, and other process conditions are listed in Table 1.

Embodiment 10

[0023] Except that tert-amyl alcohol is used as the solvent, the rest is the same as in Examples 1-8, and other process conditions are listed in Table 1.

[0024] The reaction results of each example are shown in Table 2.

[0025] CPD / solvent

(weight ratio)

CPD / H 2

(mol ratio)

Reaction pressure

(MPa)

temperature reflex

(℃)

Catalyst load

(hr -1 )

M5 / M4

(weight ratio)

Example 1

1∶5

1∶3.2

1.2

55

7.0

1∶10

Example 2

1∶8

1∶2.1

1.2

46

6.0

1∶5

Example 3

1∶8

1∶2.1

0.9

45

5.5

1∶8

Example 4

1∶8

1∶2.1

1.5

43

5.5

1∶8

Example 5

1∶8

1∶2.1

1.2

43

5.5

1∶8

Example 6

1∶8

1∶2.4

1.2

50

3.5

1∶12

Example 7

1∶8

1∶1.5

1.2

40

5.5

1∶4

Example 8

1∶10

...

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PUM

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Abstract

The continuous cyclopentadiene hydrogenating process to prepare cyclopentene is one continuous catalytic hydrogenation reaction of the mixture of cyclopentadiene, solvent and hydrogen in a fixed bed catalyst bed. The catalyst includes gamma-Al2O3 as carrier and Pa as active component. The solvent is any one of benzene, toluene, cyclohexane, ethanol, methanol, tertiary amyl alcohol and tertiary butyl alcohol. The molar ratio between cyclopentadiene and hydrogen is 1 to 1.5-3.5, and the reaction system has pressure of 0.9-1.5 MPa and temperature of 30-55 deg.c. The reacted liquid is discharged partially and externally circulated partially with the weight ratio being 1 to 6-12, and the externally circulated liquid after being cooled is mixed with cyclopentadiene material and solvent before being mixed with hydrogen in venturi ejector, atomized into gas-liquid mixture and reacted in the catalyst bed. The catalyst load is 4-7/hr accounted in liquid phase material, and the reacted heat is transferred via external circulation.

Description

Technical field [0001] The invention relates to a method for preparing cyclopentene by selective hydrogenation of cyclopentadiene. Background technique [0002] Cyclopentene is an intermediate for many fine chemical products. For example, it can be used to produce high value-added pharmaceutical intermediates such as cyclopentanol, bromocyclopentane, chlorocyclopentane, and cyclopentane acid. Cyclopentene is also a poly The main raw material of cyclic olefin polymer. In the prior art, cyclopentene can be obtained by a variety of methods, but the method of producing cyclopentadiene by hydrogenation has the most industrial application prospects. For example, US Patent 3,994,986 uses dicyclopentadiene to depolymerize into cyclopentadiene, and then two-stage hydrogenation to continuously produce cyclopentene. The tubular reactor is used as the hydrogenation reactor, the molar ratio of hydrogen to cyclopentadiene in the first stage is (1~1.5):1, and the ratio in the second stage is (1...

Claims

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Application Information

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IPC IPC(8): C07C13/12C07C5/05
Inventor 周飞郭世卓蒋正兴范存良顾超然
Owner SINOPEC SHANGHAI PETROCHEMICAL CO LTD
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