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Method for separation recovery of cyclohexene oxide from cyclohexanone by-product light oil

A technology of epoxy cyclohexane, separation and recovery, applied in the direction of organic chemistry, etc., can solve the problem of not involving the treatment of aldehydes and ketone impurities, not mentioning the total yield of epoxy cyclohexane, reducing the scope of application and use value. and other problems, to achieve the effect of being conducive to purification, reducing production costs and convenient operation

Inactive Publication Date: 2014-01-15
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process converts epoxycyclohexane into other substances, which reduces its application range and use value. At the same time, the process is complicated, with many steps, and the introduction of acid and alkali, which increases production costs and pollutes the environment.
[0007] Patent CN1295068A mentions a method for recovering cyclohexane epoxy product from cyclohexane oxidation by-product to remove alcohol and then refine it, which is characterized in that the crude epoxy cyclohexane to be refined is removed alcohol Impurities, to obtain epoxy cyclohexane products with a purity of 99%, the total yield of epoxy cyclohexane is not mentioned in this process, and the treatment of aldehydes and ketones impurities is not involved

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Take 600g of light oil, in which epoxycyclohexane content is 35.3%, carry out pre-rectification under reduced pressure (vacuum degree 100kpa), control reflux ratio 6:1, collect 42~50℃ fraction as epoxycyclohexane The crude product was detected and analyzed by gas chromatography, and the sample contained 90.52% epoxycyclohexane, 7.2% aldehyde and ketone impurities, and 2.24% alcohol impurities. Add the crude epoxycyclohexane and 28.9g of phenylhydrazine into a 500ml four-necked flask, adjust the pH to 3~5 with a weak acid, react under reflux for 2 hours, filter after cooling, add 2g of sodium hydroxide to the filtrate, React under low pressure for 2 hours, filter after cooling, and then intermittently rectify the filtrate, control the reflux ratio to 6:1, and collect the fraction at 42-50°C under reduced pressure (vacuum degree 100kpa). Obtain product 183.3g, detect and analyze through gas chromatography, the epoxycyclohexane content is 99.11%, and the epoxycyclohexane t...

Embodiment 2

[0020] Take 500g of the same light oil as in the above example, carry out pre-rectification under reduced pressure (vacuum degree 95kpa), control the reflux ratio to 5:1, collect the distillate at 42~50°C as the crude epoxycyclohexane, and pass through the gas phase Chromatographic detection and analysis showed that the sample contained 89.7% epoxycyclohexane, 7.7% aldehyde and ketone impurities, and 2.1% alcohol impurities. Add the crude epoxycyclohexane and 30.8g 2,4-dinitrophenylhydrazine into a 500ml four-necked flask, adjust the pH to 3~5 with a weak acid, react for 3 hours under reflux, filter after cooling, and add 3g sodium hydroxide, react under reflux conditions for 3 hours, filter after cooling, then intermittently rectify the filtrate, control the reflux ratio to 5:1, and collect 42-50°C fractions under reduced pressure (vacuum degree 95kpa). Obtain product 150.7g, detect and analyze through gas chromatography, the epoxycyclohexane content is 99.02%, and the epoxyc...

Embodiment 3

[0022] Take 630g of the same light oil as in the above example, carry out pre-rectification under reduced pressure (vacuum degree 100kpa), control the reflux ratio to 8:1, collect the distillate at 42-50°C as the crude epoxycyclohexane, and pass through the gas phase Chromatographic detection and analysis showed that the sample contained 91.2% epoxycyclohexane, 6.3% aldehyde and ketone impurities, and 2.05% alcohol impurities. Add the crude epoxycyclohexane and 39.7g of phenylhydrazine into a 500ml four-neck flask, adjust the pH to 3~5 with a weak acid, react under reflux for 2 hours, filter after cooling, add 2g of potassium hydroxide to the filtrate, React under low pressure for 2 hours, filter after cooling, and then intermittently rectify the filtrate, control the reflux ratio to 8:1, and collect the fraction at 42-50°C under reduced pressure (vacuum degree 100kpa). Obtain product 189.7g, detect and analyze by gas chromatography, the epoxycyclohexane content is 99.23%, and...

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PUM

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Abstract

Belonging to the technical field of organic chemistry, the invention relates to a method for separation recovery of cyclohexene oxide from light oil which is a by-product of cyclohexane oxidation for preparing cyclohexanone and cyclohexanol. The method is characterized by: subjecting the light oil to pre-rectification, conducting chemical treatment on a separated cyclohexene oxide crude product to remove aldehyde ketone and alcohol impurities contained therein, and finally carrying out purification rectification. Thus, the purpose of recovering cyclohexene oxide from the light oil can be reached, and the cyclohexene oxide with purity up to more than 99% can be obtained.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and relates to a method for separating and recovering epoxycyclohexane from light oil, the by-product of producing cyclohexanone and cyclohexanol by cyclohexane oxidation. Background technique [0002] Epoxycyclohexane is an important organic synthesis intermediate, which can be used in medicine, pesticide, curing agent, plasticizer, diluent, surfactant and so on. Its production method can be chemical synthesis, and can also be extracted from light oil, which is a by-product of cyclohexanone. Its application is mainly concentrated in the aspects of decantec pesticide and epoxy resin curing agent and diluent. [0003] In the industrial production of cyclohexane oxidation to prepare cyclohexanone and cyclohexanol, various by-products such as X oil, light oil, and waste lye are also generated while the target product is produced. The content of epoxycyclohexane in the light oil is 20-40%...

Claims

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Application Information

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IPC IPC(8): C07D303/04C07D301/32
CPCC07D303/04C07D301/32
Inventor 何育苗吴红兵金汉强周亚苓陈英斌赵思远
Owner CHINA PETROLEUM & CHEM CORP
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