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Method for preparing epsilon-caprolactone from solvent-free cyclohexanone

A cyclohexanone, solvent-free technology is applied in the field of preparation of ε-caprolactone, which can solve the problems of pipeline blockage, high price, and inability to take advantage, and achieves reduced process energy consumption, mild reaction conditions, and simplified solvent separation. the effect of the craft

Inactive Publication Date: 2020-05-05
广州昊科生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the zirconium used in this system is a rare metal, which is expensive and cannot have an advantage in industrial production
In addition, the amount of benzaldehyde used in the system is too high, and the generated benzoic acid is insoluble in cyclohexanone, and will continue to precipitate during the reaction process, resulting in solid crystallization in the system, and there is a risk of pipeline blockage in industrial applications.

Method used

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  • Method for preparing epsilon-caprolactone from solvent-free cyclohexanone
  • Method for preparing epsilon-caprolactone from solvent-free cyclohexanone
  • Method for preparing epsilon-caprolactone from solvent-free cyclohexanone

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Experimental program
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Effect test

Embodiment 1～3

[0030] Solvent system: add 1.306g o-dichlorobenzene (internal standard substance), 0.4907g cyclohexanone, 1.121g acrolein and 100mg nitrogen-doped carbon nanotubes into the autoclave, add 17ml reaction solvent as shown in Table 1 .

[0031] Solvent-free system: 1.306g o-dichlorobenzene (internal standard), 10.45g cyclohexanone, 6.216g acrolein and 100mg nitrogen-doped carbon nanotubes were added to the autoclave.

[0032] Both systems were heated to 50°C at a rotation speed of 1000 rpm, oxygen was introduced, timing was started, and the pressure was maintained at 1 MPa during the reaction. After reacting for 2 hours, the reaction kettle was cooled to 15°C in ice water, and the liquid-solid phase mixture was filtered to obtain a solid catalyst and a liquid phase mixture containing unreacted reactants and reaction products. The product GC detection results are shown in Table 1.

[0033] Table 1. The influence of solvent on the oxidation reaction of cyclohexanone B-V

[0034]

Embodiment 4

[0036] Add 1.306g o-dichlorobenzene (internal standard substance), 10.45g cyclohexanone, 6.216g acrolein and 50mg nitrogen-doped carbon nanotubes into the autoclave, mix and heat to 50°C at a stirring rate of 1000rpm, and pass oxygen , Start timing and maintain its pressure at 1MPa during the reaction. After reacting for 2 hours, the reaction kettle was cooled to 15°C in ice water, and the liquid-solid phase mixture was filtered to obtain a solid catalyst and a liquid phase mixture containing unreacted reactants and reaction products. Product GC detection results: the conversion rate of cyclohexanone was 17.88%, the selectivity and absolute production of ε-caprolactone were 71% and 13.46 mol, respectively. The conversion rate of acrolein was 83.3%, and the selectivity of acrylic acid was 97.6%.

Embodiment 5

[0038] Add 1.306g o-dichlorobenzene (internal standard substance), 10.45g cyclohexanone, 6.216g acrolein and 100mg nitrogen-doped carbon nanotubes into the autoclave, stir and heat to 50℃ at 1000rpm, and pass 0.5 The oxygen at MPa pressure starts timing and maintains its pressure constant during the reaction. After reacting for 2 hours, the reaction kettle was cooled to 15°C in ice water, and the liquid-solid phase mixture was filtered to obtain a solid catalyst and a liquid phase mixture containing unreacted reactants and reaction products. Product GC detection results: the conversion rate of cyclohexanone was 16.11%, the selectivity and absolute production of caprolactone were 76% and 12.88 mmol, respectively. The conversion rate of acrolein was 87.4%, and the selectivity of acrylic acid was 99.7%.

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Abstract

The invention discloses a method for preparing epsilon-caprolactone from solvent-free cyclohexanone. The method comprises the following steps: adding a nitrogen-doped carbon nanotube catalyst into a mixture of cyclohexanone and acrolein, and reacting at 30-100 DEG C by taking molecular oxygen as an oxidant to obtain epsilon-caprolactone, wherein no solvent is added into the reaction system. According to the method, a nitrogen-doped carbon nanotube is used as a catalyst, cyclohexanone is converted into epsilon-caprolactone with high conversion rate and high selectivity under the solvent-free condition, the solvent separation process in the industrial process is simplified, the process energy consumption is reduced, the space of a container is more fully utilized, the volume utilization rateof a reactor is increased, the catalyst is easy to recover, the oxidant is green and environmentally friendly, and the cost is lower.

Description

Technical field [0001] The invention relates to the field of preparation of epsilon-caprolactone, in particular to a method for preparing epsilon-caprolactone without solvation of cyclohexanone. Background technique [0002] ε-caprolactone is an important organic synthesis intermediate and a new type of polyester monomer with very superior physical and chemical properties. Polycaprolactone prepared from ε-caprolactone monomer has excellent thermal plasticity and processing and molding capabilities. It can be made into plastic products with good environmental affinity, and it can also be made into biodegradable medical materials. Many methods for the synthesis of ε-caprolactone have been reported. Among them, the synthesis of ε-caprolactone by Baeyer-Villiger (B-V) oxidation of cyclohexanone is a research hotspot. [0003] The early cyclohexanone BV oxidation method mainly used peroxy acid and hydrogen peroxide as oxidants, which had good activity. However, peroxy acid and hydroge...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D313/04B01J27/24
CPCB01J27/24C07D313/04Y02P20/584
Inventor 余皓曹永海刘夺彭峰王红娟
Owner 广州昊科生物科技有限公司
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