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Method for preparing cyclopentanone through furfural water liquid hydrogenation rearrangement

A technology of cyclopentanone and furfural, which is applied in the field of furfural water-liquid hydrogenation rearrangement to prepare cyclopentanone, can solve the problems of complex reaction, large amount of catalyst usage, harsh conditions, etc., achieve good stability and cycle performance, and reduce catalyst cost The effect of reducing and environmental protection in the synthesis process

Pending Publication Date: 2022-04-22
GUANGDONG UNIV OF PETROCHEMICAL TECH
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Problems solved by technology

However, the hydrogenation conversion of furfural to cyclopentanone requires the participation of a highly active hydrogenation catalyst and the participation of protons in an aqueous environment. The process is difficult to realize. Due to the harsh conditions and complex reactions, this process has not yet been industrialized, and further research is needed. Exploration and Development
[0006] In 2011, Xu Jie from the Dalian Institute of Chemical Physics, Chinese Academy of Sciences [CN 103159606A] explored the use of various metal catalysts loaded on different supports for the hydrogenation of 15% furfural aqueous solution, and found that Ru-Ce / SiO 2 The catalytic performance is the best, the conversion rate is as high as 97%, the selectivity of cyclopentanone can reach 74%, and the yield is only 72%. The catalyst is used for low-concentration furfural aqueous solution, and the yield can only reach 72% under the best conditions, the product purity is not ideal, and the catalyst cost is high; in 2013, Xiao Guomin [CN103111299A] of Southeast University invented activated carbon and carbon nanotube loading Catalysts composed of Ni, Cu, Co, Mg and other metals treat 20% furfural aqueous liquid hydrogenation, and the yield of cyclopentanone is as high as 92% under the best conditions, but the amount of catalyst used is large and the cost of catalyst is high; Chinese Academy of Sciences Guangzhou Energy Zhang Qi [CN 201210371531A] of the research institute also used a pure metal catalyst for furfural aqueous solution with a concentration of 5%, and the generated product contained cyclopentanone and cyclopentanol, and the total yield of the two was only 52%. The effect is not good and the product is difficult to separate; in 2014, Wei Ruiping [CN 104069886A] of Southeast University used a 15% Pt-10% Co / HY type catalyst to treat 20% furfural aqueous solution, and the yield was as high as 96%, and proposed a porous Y type The unique pores of molecular sieves are not easy to deposit carbon, but the proportion of precious metals is as high as 15%, and the catalyst is expensive; there are many similar recent patent reports, and the main research contents are listed in Table 1
There are many similar reports, focusing on the catalyst composition of this system, the regulation of active components, the influence of additives, the influence of solvent, the influence of temperature and pressure, etc., but there is no ideal catalyst that can be used for furfural addition. Hydrogen rearrangement to cyclopentanone

Method used

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  • Method for preparing cyclopentanone through furfural water liquid hydrogenation rearrangement
  • Method for preparing cyclopentanone through furfural water liquid hydrogenation rearrangement
  • Method for preparing cyclopentanone through furfural water liquid hydrogenation rearrangement

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preparation example Construction

[0034] Catalyst preparation and hydrogenation method:

[0035] Preparation and synthesis of the carrier: Diatomaceous earth was fully dried at 110°C and ground into powder, passed through a 200-mesh sieve and placed in a beaker, adding dilute sulfuric acid with a mass fraction of 40% (solid-liquid mass ratio was 1:4) , transferred to a three-necked flask, placed in an oil bath at 80°C for continuous mechanical stirring for 8 hours, suction filtered after cooling, fully washed with distilled water until the filtrate was neutral, transferred to a drying oven and kept at 110°C for 24 hours, cooled and transferred to Crucible, placed in a muffle furnace and kept at 450 ° C for 4 hours, ground evenly for later use.

[0036] Another 2.70 g of the above solid powder was added to a round bottom flask containing 1.00 NaOH solid and 25.00 mL of distilled water and heated to 80 ° C for 4 h to obtain a sodium silicate precursor. Alkyltrimethylammonium bromide and 50mL distilled water wer...

Embodiment 1

[0039] Embodiment 1: the hydrogenation device is a stainless steel high-pressure electric heating reactor of 50 milliliters, at first the furfural of 2.4 g is added to the distilled water of 17.6 g, utilizes magnet to stir 30min to form uniform mass fraction and is the furfural aqueous liquid of 12wt%, then adds 0.10g of catalyst A, quickly close the autoclave, and replace the air in the autoclave with hydrogen for 3-4 times, start stirring, adjust the pressure of the hydrogen gas introduced to 2.0MPa, raise the temperature to 160°C, continue to react at this temperature for 240min, then cool to At room temperature, after carefully releasing the pressure, take out the product and weigh it, and take the upper liquid and centrifuge it to detect it using the internal standard method of gas chromatography, n-butanol is used as the internal standard, and the calculated conversion and selectivity data of related species are shown in Table 1.

Embodiment 2

[0040] Example 2: Catalyst B is selected, the reaction feeding and hydrogenolysis reaction conditions are the same as in Example 1, and the calculated conversion and selectivity data of related species are shown in Table 1.

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Abstract

The invention discloses a method for preparing cyclopentanone through furfural water liquid hydrogenation rearrangement. According to the method, the cyclopentanone is prepared by catalyzing one-step hydrogenation rearrangement of the furfural water liquid by loading Ru and Cu bimetals doped on the MCM-41 through TiO2 doping, the highest selectivity of the cyclopentanone reaches 98.79%, the corresponding furfural conversion rate is 99.75%, namely, the yield is as high as 98.54%, meanwhile, the mass fraction of furfural in the furfural water liquid to be reacted can be remarkably improved and reaches 10-15%, and the method is suitable for industrial production. Therefore, enrichment and batch treatment of reaction products are facilitated. The method has the advantages of short process route, simple reaction equipment and operation method, mild reaction conditions, short reaction time, simple and easily available catalyst, low cost, good stability, pure product, easy separation and purification, reduction of the content of precious metals, effective increase of the mass fraction of the reactant furfural, and realization of industrial production. The expected economic benefit is very considerable, and the method has great significance in application of industrial production.

Description

technical field [0001] The invention relates to the preparation of cyclopentanone, in particular to a method for preparing cyclopentanone by furfural aqueous liquid hydrogenation rearrangement. Background technique [0002] The energy crisis has been continuously sounding the alarm for human development. The efficient use of renewable biomass resources can effectively make up for energy shortages, reduce human dependence on fossil energy, and indirectly reduce the pollution of fossil energy. It has an important sustainable The scientific significance and application prospects of sexual development have attracted the attention of scientific and technological workers around the world in recent years. As a new type of biomass energy, furfural widely exists in agricultural and forestry wastes such as corncobs, bagasse, and cottonseed hulls. In recent years, the annual output of furfural in my country has exceeded 300,000 tons, accounting for more than 80% of the world's total pr...

Claims

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Application Information

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IPC IPC(8): C07C49/395C07C45/59B01J29/04B01J29/03
CPCC07C45/59B01J29/044B01J29/0333C07C2601/08B01J2229/20C07C49/395Y02P20/584
Inventor 龙威金烈陆泳潼黄银飞陈志龙周统武洪奕阳
Owner GUANGDONG UNIV OF PETROCHEMICAL TECH
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