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Preparation method of alkyl diphenyl ether

A technology of alkyl diphenyl ether and diphenyl ether, which is applied in the field of preparation of alkyl diphenyl ether, can solve problems such as insufficient yield of monosubstituted products, high concentration of ionic liquid, and low yield of monosubstituted products, and achieve the elimination of waste water Effects of emissions problems

Inactive Publication Date: 2007-12-05
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the method described in this patent requires a high concentration of ionic liquid, and the molar ratio of ionic liquid to olefin must be at least 0.2:1.
And there is the low problem of single substitution product yield, even if the mol ratio of ionic liquid and olefin is increased to 0.33: 1, the productive rate of target product monoalkyl diphenyl ether is still less than 88%
[0006] Although the above disclosed patented technologies have different catalysts, they all have problems such as large amount of catalyst used and insufficient yield of monosubstituted products, which are not suitable for large-scale industrial application.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Inject 20 moles (3400 g) of diphenyl ether (Qingdao Weibang Chemical Co., Ltd.) and 1 mole (168 g) of normal α-dodecene (industrial product, product of AGRIFU, LAO C12) into a 5L reactor respectively. The catalyst consists of trimethylammonium chloride hydrochloride and aluminum trichloride with a molar ratio of 1:2. The catalyst is injected into the reactor respectively at a ratio of 0.004 (molar ratio) to the olefin. After stirring and raising the temperature to 180°C for 2 hours, the stirring was stopped, and after standing for stratification, the upper layer was transferred to a 3L distillation pot, and the excess diphenyl ether was distilled off under reduced pressure. The product was analyzed by gas chromatography and the yield of the monoalkyl substituted product was 92.5%.

Embodiment 2

[0018] Inject 15 moles (2550 g) of diphenyl ether and 1 mole (168 g) of normal α-dodecene (commercial product, product of Agrof, LAO C16) into a 5 L reactor respectively. The catalyst consists of pyridine and aluminum trichloride in a molar ratio of 1:2. The molar ratio of catalyst to olefin was 0.004. The reaction temperature was 185° C., and the rest of the steps were the same as in Example 1. The yield of monoalkyl substituted product was 91.0% according to gas chromatography analysis.

Embodiment 3

[0020] Inject 12 moles (2040 g) of diphenyl ether and 1 mole (168 g) of normal α-dodecene (commercial product, product of Agrof, LAO C12) into a 5 L reactor respectively. The catalyst consists of chlorobutylpyridine and aluminum trichloride in a molar ratio of 1:2. The molar ratio of catalyst to olefin was 0.004. The reaction temperature was 190° C., and the rest of the steps were the same as in Example 1. The yield of monoalkyl substituted product was 90.2% according to gas chromatography analysis.

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Abstract

The process of preparing alkyl diphenyl ether includes the steps of: mixing diphenyl ether, olefin and chloroaluminic acid type ionic liquid in the molar ratio to the olefin of 0.002-0.1; reacting at 120-220 deg.c; and separating and collecting the target product alkyl diphenyl ether. The process has high yield of alkyl diphenyl ether and low catalyst consumption.

Description

technical field [0001] The present invention relates to the preparation method of alkyl diphenyl ether. Background technique [0002] Alkyl diphenyl ethers can be used as fuel additives to lower the freezing point; base oils for synthetic lubricating oils or lubricating esters. After sulfonation, they can be used as anti-salt detergents, emulsifiers, and foam oil displacement agents. They are required by the daily chemical industry and the petroleum industry. very big. Alkyl diphenyl ethers can be synthesized by reacting olefins, halogenated hydrocarbons, straight-chain or cyclic fatty alcohol sulfates with diphenyl ethers. Early alkylation processes used C 6 ~C 16 The α-olefin and diphenyl ether are catalyzed by aluminum trichloride to form alkyl diphenyl ether, and the degree of alkylation is 1-1.3. The amount of catalyst used is as high as 10% of the olefin mass, and multiple washings are required to remove the catalyst in the product, thus generating a large amount o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/263C07C41/30B01J31/14
Inventor 彭朴葸雷段启伟
Owner CHINA PETROLEUM & CHEM CORP