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Method for synthesizing methyl cyclopentadiene from 3-methyl-2-cyclopentene-1-one

A technology of methylcyclopentadiene and cyclopentene, applied in chemical instruments and methods, hydrocarbons, hydrocarbons, etc., to achieve the effects of mild reaction conditions, simple catalyst preparation, and low energy consumption

Active Publication Date: 2020-06-02
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Up to now, there is no literature report on using 3-methyl-2-cyclopenten-1-one as raw material to carry out hydrodeoxygenation to synthesize methylcyclopentadiene

Method used

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  • Method for synthesizing methyl cyclopentadiene from 3-methyl-2-cyclopentene-1-one
  • Method for synthesizing methyl cyclopentadiene from 3-methyl-2-cyclopentene-1-one
  • Method for synthesizing methyl cyclopentadiene from 3-methyl-2-cyclopentene-1-one

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] (1) Supported metal oxide A / X type catalyst Co 3 O 4 / SiO 2 Preparation: Weigh 3 grams of SiO pretreated at 250℃ for 15h 2 , Immerse it in an equal volume of an aqueous solution containing 2.90 g of cobalt nitrate, immerse it for 12 hours and then dry it at 60°C for 48 hours, then calcinate it at 500°C for 4 hours, and then press into a tablet. Co prepared 3 O 4 / SiO 2 Metal oxide Co in catalyst 3 O 4 The content is 21Wt%, the carrier SiO 2 The content is 79Wt%.

[0022] The above Co 3 O 4 / SiO 2 One gram of catalyst is packed in a fixed-bed continuous reactor, and then the hydrogen pressure is 0.2MPa and the hydrogen space velocity is 500h. -1 The reduction temperature is 450℃ for 1 hour, and then the bed temperature of the fixed-bed continuous reactor is kept at 450℃, and the reaction pressure is controlled to 0.02MPa. The space-time of 3-methyl-2-cyclopenten-1-one Speed ​​is 0.5h -1 , The molar ratio of hydrogen to 3-methyl-2-cyclopenten-1-one is 50:1, the conversion rat...

Embodiment 2

[0024] (1) Supported metal oxide A / X type catalyst Fe 3 O 4 / ZrO 2 Preparation: After preparing 100 grams of 5 grams of ferric nitrate aqueous solution, it is divided into two parts B and C with equal mass, and 10 grams of carrier ZrO is added to B 2 , Add 15 grams of urea to C, slowly add C to B in a water bath at 80°C, keep it at 90°C for 10 hours and then dry at 120°C for 48 hours, then calcinate at 600°C for 4 hours, and then press into tablets. The metal oxide component Fe in the prepared catalyst 3 O 4 The content is 9Wt%, carrier ZrO 2 The content is 91Wt%.

[0025] The above Fe 3 O 4 / ZrO 2 One gram of catalyst is packed in a fixed-bed continuous reactor, and then the hydrogen pressure is 0.5MPa and the hydrogen space velocity is 2000h. -1 、Reduction at 400℃ for 3 hours, then keep the bed temperature of the fixed-bed continuous reactor at 400℃, control the reaction pressure to 0.3MPa, and the hourly space velocity of 3-methyl-2-cyclopenten-1-one 2h -1 , The molar ratio of ...

Embodiment 3

[0027] (1) Supported metal oxide A / X type catalyst WO 3 / CeO 2 Preparation: Weigh 3 grams of CeO pretreated at 600°C for 2 hours 2 , Immerse the same volume in an aqueous solution containing 4 g of sodium tungstate, immerse for 5 hours and then dry at 120°C for 12 hours, then calcinate at 700°C for 1 hour, and then press into tablets. Prepared WO 3 / CeO 2 Metal oxide component WO in catalyst 3 The content is 49Wt%, the carrier CeO 2 The content is 51Wt%.

[0028] Put the above WO 3 / CeO 2 One gram of catalyst is packed in a fixed-bed continuous reactor, and then the hydrogen pressure is 0.8MPa and the hydrogen space velocity is 4000h -1 、Reduction at 500℃ for 1 hour, then control the reaction temperature at 500℃, the reaction pressure is 0.5MPa, and the hourly space velocity of 3-methyl-2-cyclopenten-1-one is 4h -1 , The molar ratio of hydrogen to 3-methyl-2-cyclopenten-1-one is 200:1, the conversion rate of 3-methyl-2-cyclopenten-1-one is 100%, and the methyl ring The selectivity...

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Abstract

The invention relates to a method for synthesizing methyl cyclopentadiene from 3-methyl-2-cyclopentene-1-one. The method comprises the following steps: carrying out a hydrodeoxygenation reaction in afixed bed continuous reactor under the action of a supported metal oxide A / X catalyst by using 3-methyl-2-cyclopentene-1-one as a raw material to synthesize the target product methyl cyclopentadiene.The method is simple in process route, environmentally friendly and simple in catalyst preparation, and provides a new effective way for synthesis of methylcyclopentadiene from 3-methyl-2-cyclopentene-1-one.

Description

Technical field [0001] The invention relates to a method for synthesizing methylcyclopentadiene with 3-methyl-2-cyclopenten-1-one. Background technique [0002] As an important chemical, methylcyclopentadiene is the main raw material for the production of epoxy resin curing agent methyl nadic anhydride and gasoline antiknock agent methyl cyclopentadiene manganese tricarbonyl. In addition, it is also used to synthesize a series of products such as polyolefin catalysts, medicines, dye additives, and high-energy fuel RJ-4. At present, the industrial production of methylcyclopentadiene mainly uses petroleum pyrolysis tar as the raw material, which is distilled to cut the C 6 The raw material oil is dimerized into polymerized oil, and then often distilled under reduced pressure. The crude dimerization mixture is collected, depolymerized and rectified by heating to obtain crude methylcyclopentadiene. The crude methylcyclopentadiene is dimerized It is transformed into crude dimethylcyc...

Claims

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Application Information

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IPC IPC(8): C07C1/207C07C13/15B01J23/22B01J23/30B01J23/34B01J23/72B01J23/745B01J23/75B01J23/888B01J23/889
CPCB01J23/002B01J23/22B01J23/30B01J23/34B01J23/72B01J23/745B01J23/75B01J23/888B01J23/8892B01J2523/00C07C1/2076C07C2523/22C07C2523/30C07C2523/34C07C2523/72C07C2523/745C07C2523/75C07C2523/888C07C2523/889C07C2601/10C07C13/15B01J2523/27B01J2523/68B01J2523/842B01J2523/48B01J2523/69B01J2523/31B01J2523/41B01J2523/55B01J2523/845
Inventor 李宁刘艳廷李广亿张涛王爱琴王晓东丛昱
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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