Method for utilizing o-chlorocyclohexanol to prepare cyclohexene oxide by cyclization

A technology of o-chlorocyclohexanol and epoxycyclohexane, which is applied in the field of organic chemical synthesis, can solve problems such as inability to produce large quantities of products, fail to meet industrial needs, and cumbersome process routes, and achieve practical and easy processes and production The effect of cost reduction and simple process

Inactive Publication Date: 2013-03-27
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Although the above-mentioned several patents obtained high-purity epoxycyclohexane, it was mainly recovered from by-products, the process was complicated, and a large amount of liquid alkali was used in the process, resulting in a large amount of waste water, followed by recovery from by-products , unable to produce large quantities of products, let alone meet industrial needs
[0007] In addition, domestic CN1331077A and CN1380291A have introduced a kind of utilizing halogenated hydrogen reaction to produce 2-halogenated cyclohexanol, and then reacting chlorohydrin and sodium hydroxide solution to obtain epoxycyclohexane, this process route is loaded down with trivial details, uses in the process A large amount of liquid alkali catalyst, after the reaction, a large amount of industrial wastewater is produced, causing great damage to the environment

Method used

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  • Method for utilizing o-chlorocyclohexanol to prepare cyclohexene oxide by cyclization
  • Method for utilizing o-chlorocyclohexanol to prepare cyclohexene oxide by cyclization
  • Method for utilizing o-chlorocyclohexanol to prepare cyclohexene oxide by cyclization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment example 1

[0022] The preparation of the first step solid base

[0023] Take 8g of activated carbon, impregnate with equal volume of the prepared 4mol / L potassium carbonate solution, impregnate at 40°C for 4h, dry at 100-120°C, then roast in a muffle furnace at 500°C for 5h, cool to room temperature and grind , That is, the loading of potassium carbonate is 40%.

[0024] The preparation of the 2nd step epoxycyclohexane

[0025] Add 4g of the above-mentioned solid base, 5g of o-chlorocyclohexanol, and 20mL of absolute ethanol into a 50mL round-bottomed flask, install a condenser tube, heat and stir in an oil bath at 75°C for 2 hours, and analyze the product by gas chromatography, epoxycyclohexane The yield can reach 80.36%, and the selectivity to epoxycyclohexane can reach 98.67%.

Embodiment example 2~4

[0027] Except that the following carriers are different, the others are the same as Example 1, and the carriers shown in Table 1 are used respectively.

[0028] Table 1

[0029]

Embodiment example 5

[0031] Into a 50mL round bottom flask, add 1g loading capacity of 20, 40, 50% K 2 CO 3 impregnated K 2 CO 3 / C solid base (the preparation method of the solid base is the same as in Example 1 except for the loading capacity), 5g of o-chlorocyclohexanol, 20mL of ethanol with a condenser tube, heated and stirred in a 75°C oil bath for 2h, and the product was analyzed by gas chromatography Analysis, the yield and selectivity of epoxycyclohexane are as shown in table 2.

[0032] Table 2

[0033]

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PUM

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Abstract

The invention relates to a method for utilizing o-chlorocyclohexanol to prepare cyclohexene oxide by cyclization. The method comprises the steps of weighing o-chlorocyclohexanol, solid alkali and a solvent, placing the o-chlorocyclohexanol, the solid alkali and the solvent into a reactor to undergo a reaction, performing a heating stirring reaction, obtaining a reaction mixture after the reaction is finished, and obtaining the product cyclohexene oxide by separation. The solid alkali is a load type metal salt, and the adopted solvent is lower alcohol. The method has the advantages that a large number of waste water caused by used sodium hydroxide serving as a catalyst is avoided, the production cost is reduced, the process is simple, the used solid alkali has no harm to the human body and can be separated from a product easily, the method is a green chemical process, the used solid alkali is high in selectivity for a principal product, and the method is favorable for the reaction.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a method for preparing epoxycyclohexane by cyclization of o-chlorocyclohexanol. Background technique [0002] Cyclohexane oxide, also known as cyclohexene oxide, is a colorless or light yellow liquid with a scent. Cyclohexane epoxy has a wide range of uses. It is not only an important intermediate in organic synthesis, it can be used to prepare pesticides such as gram wax, adipic acid, nylon, epoxy coatings, rubber accelerators, dyes, medicines, etc., and can also be used to prepare Polymer regulators, surfactants, etc., but also an organic solvent with strong solubility. In addition, due to the presence of very active epoxy groups in the molecular structure of epoxycyclohexane, it can react with ammonia, amines, phenols, alcohols, carboxylic acids and other substances to form a series of compounds, and the various types of compounds obtained by the reaction ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/04C07D301/26
Inventor 林陵芮杰曾崇余张耘华
Owner NANJING UNIV OF TECH
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