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Method for preparing cyclopentanol from cyclopentene through hydration

A technology composed of cyclopentene water and cyclopentene water, applied in hydroxyl addition preparation, organic chemistry and other directions, can solve the problems of high toxicity of phenol, difficult stirring, high viscosity, etc., to improve the reaction yield and increase mutual solubility. , the effect of reducing energy consumption

Inactive Publication Date: 2011-04-13
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After adding phenol, the conversion rate of cyclopentene is significantly improved, but there are many disadvantages in using phenol as a solvent: 1) phenol is unstable and prone to side reactions such as alkylation, etherification, and oxidation
2) The products of phenol alkylation and etherification reactions are all high-boiling compounds with high viscosity and difficult post-treatment; if they are not treated and recycled with phenol, they will accumulate in the reaction system, increasing the viscosity of the system and making stirring difficult
3) Phenol is highly toxic and easily causes environmental pollution problems
These disadvantages make it difficult to industrialize phenol as a solvent

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] The hydration reaction is carried out in a 250ml autoclave with a heating device and a stirring device in the autoclave. Add 43.20g H to the autoclave 2 O (2.40mol), 27.20g n-butanol, 9.66g Amberlyst36 resin catalyst, 27.20g (0.4mol) cyclopentene, replace the air in the system with nitrogen three times, boost the pressure to 1.20MPa, stir and heat up, and control the reaction temperature at 120 ~160°C, the reaction time is 4h.

[0016] After the reaction is finished, cool to room temperature, discharge the material, filter the resin with a 90-mesh standard sieve, separate the reaction liquid, and distill and separate the water phase material and the oil phase material respectively to obtain cyclopentanol and unreacted cyclopentene.

Embodiment 2

[0024] In a high-pressure vessel, water, cyclopentene and n-butanol are added in a molar ratio of 4:1. The mass ratio of n-butanol to cyclopentene is 1:1. Next, replace the air in the system with nitrogen for 3 times, increase the pressure to 1.0Mpa, and react for 8 hours at 120°C to obtain cyclopentanol. The amount of acidic cation exchange resin Amberlyst35 is 9% of the total mass of the system. The conversion rate of cyclopentene was 14.56%, and the selectivity of cyclopentanol was 90.48%.

Embodiment 3

[0026] In a high-pressure vessel, water, cyclopentene and n-pentanol are added in a molar ratio of 6:1. The mass ratio of n-pentanol to cyclopentene is 2:1. After replacing the air in the system twice with nitrogen, the pressure was increased to 3.0Mpa, and the reaction was carried out at 160°C for 0.5h to obtain cyclopentanol. The amount of acidic cation exchange resin Amberlyst15 is 9% of the total mass of the system. The conversion rate of cyclopentene was 25.20%, and the selectivity of cyclopentanol was 58.70%.

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Abstract

The invention discloses a method for preparing cyclopentanol from cyclopentene through hydration, which comprises the following steps of: adding water and cyclopentene into a high-pressure container in a molar ratio of 4-6:1; adding straight-chain primary alcohol; and under the catalysis of acid cation exchange resin, displacing air in a system twice to four times by using nitrogen, then raising the pressure to 1.0 to 3.0MPa, and reacting at the temperature of between 120 and 160 DEG C for 0.5 to 8 hours to obtain cyclopentanol. In the method, straight-chain primary alcohol with atomic numberof 4 to 6 is used as a reaction solvent; the primary alcohol solvent is introduced into a reaction system, so that not only intersolubility between cyclopentene and water molecules is increased, but also the thickness of a water molecule liquid film formed on the surface of a catalyst and the resistance that cyclopentene is diffused toward the catalyst are reduced. The method is simple and has high reaction efficiency and greatly reduces the energy consumption required by refining. A water phase can be recycled and waste is not discharged almost in the whole process.

Description

technical field [0001] The present invention relates to a kind of preparation method of cyclopentanol. Background technique [0002] Cyclopentanol is an important intermediate of fine chemical products, mainly used in the preparation of bromocyclopentane, chlorocyclopentane, antibacterial drugs, antiallergic drugs and other products. At present, the production of cyclopentanol mainly adopts the adipic acid method, and the raw material conversion rate and selectivity of this method can reach up to 99%. further development of the process. There are two processes for preparing cyclopentanol from cyclopentene, indirect hydration and direct hydration. Although the indirect method has a high conversion rate (above 70%) and good selectivity (above 90%), sulfuric acid is severely corrosive to equipment. The concentration process consumes a lot of energy. Although the conversion rate of the direct hydration method is low, it solves the problems of equipment corrosion and high energ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C35/06C07C29/04
Inventor 宋健杨晓辉冯荣秀吴杰孙树娟
Owner TIANJIN UNIV
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