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Process for preparing alkyl diphenyl ether by catalyzing reaction of olefin and diphenyl ether with solid acid

An alkyl diphenyl ether, solid acid catalysis technology, applied in the preparation of organic compounds, physical/chemical process catalysts, organic chemistry and other directions, can solve problems such as unfavorable industrialization promotion, waste acid generation, etc. Simple preparation process

Pending Publication Date: 2020-07-28
CHINA RES INST OF DAILY CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Sulfuric acid solution is used in the catalyst preparation process, which has certain dangers, and waste acid is produced, which is not conducive to industrialization

Method used

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  • Process for preparing alkyl diphenyl ether by catalyzing reaction of olefin and diphenyl ether with solid acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Add ammonium sulfate and zirconium hydroxide into the reactor, the ammonium sulfate is 1% of the mass of zirconium hydroxide, after stirring evenly, calcining at 600°C for 3 hours to obtain a solid acid catalyst. Add diphenyl ether and solid acid catalyst into the reaction kettle, after heating up to 160°C, the C 16 The α-alkene was slowly added to the reactor, the olefin addition time was 30 minutes, the molar ratio of diphenyl ether and olefin was 2:1, the catalyst dosage was 0.5% of the mass of the olefin, and the reaction was continued for 120 minutes after the olefin was added, and the reaction solution was filtered to remove Catalyst, carry out vacuum distillation to remove diphenyl ether and olefin to obtain alkyl diphenyl ether, the yield is 82%.

[0022] figure 1 It is the liquid chromatogram of the reaction product without vacuum distillation. The peak time of 3.015 minutes is diphenyl ether, the peak time of 4.778 minutes is monoalkyl diphenyl ether, and the...

Embodiment 2

[0024] Add ammonium sulfate and zirconium hydroxide into the reactor, the ammonium sulfate is 1% of the mass of zirconium hydroxide, after stirring evenly, calcined at 630°C for 7 hours to obtain a solid acid catalyst. Add diphenyl ether and solid acid catalyst into the reaction kettle, after heating up to 120°C, the C 8 The α-alkene was slowly added to the reactor, the olefin addition time was 30 min, the molar ratio of diphenyl ether and olefin was 0.5:1, the catalyst dosage was 10% of the mass of the olefin, and the reaction was continued for 180 min after the olefin was added, and the reaction liquid was filtered The catalyst was removed, and diphenyl ether and olefins were removed by distillation under reduced pressure to obtain alkyl diphenyl ether with a yield of 80%.

Embodiment 3

[0026] Add ammonium sulfate, aluminum sulfate and zirconium hydroxide into the reactor, ammonium sulfate is 10% of the mass of zirconium hydroxide, and aluminum sulfate is 20% of the mass of zirconium hydroxide. After stirring evenly, calcinate at 650°C for 2 hours to obtain solid acid catalyst. Add diphenyl ether and solid acid catalyst into the reaction kettle, after heating up to 160°C, the C 12 The α-alkene was slowly added to the reactor, the olefin addition time was 120min, the molar ratio of diphenyl ether and olefin was 3:1, and the catalyst dosage was 3% of the mass of the olefin. After the olefin was added, the reaction solution was filtered to remove the catalyst, and the Diphenyl ether and olefins were removed by pressure distillation to obtain alkyl diphenyl ether with a yield of 95%.

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Abstract

The invention discloses a process for preparing alkyl diphenyl ether by catalyzing a reaction of olefin and diphenyl ether with solid acid. The method comprises the following steps: (1) preparation ofa solid acid catalyst: adding sulfate and zirconium hydroxide into a reactor, carrying out mechanical stirring for uniform mixing, and performing calcining to obtain the solid acid catalyst, whereinthe sulfate is ammonium sulfate or a mixture of ammonium sulfate and aluminum sulfate; and (2) preparation of alkyl diphenyl ether through an alkylation reaction: adding diphenyl ether and the solid acid catalyst into a reaction kettle, carrying out heating to a reaction temperature of 100-180 DEG C, slowly adding olefin into the reaction kettle, continuing reacting after the addition of the olefin is finished, filtering reaction liquid to remove the catalyst, and carrying out reduced-pressure distillation to remove the diphenyl ether and the olefin so as to obtain the alkyl diphenyl ether. The preparation process of the solid acid catalyst is simple, and no wastewater is generated in the preparation process; and the preparation process of the alkyl diphenyl ether is a heterogeneous reaction, post-treatment is simple, and the catalyst can be recycled.

Description

technical field [0001] The invention relates to a process for preparing alkyl diphenyl ether by using solid acid as a catalyst to catalyze the alkylation reaction of olefin and diphenyl ether, belonging to the technical field of organic synthesis. Background technique [0002] Alkyl diphenyl ether through SO 3 Sulfonation and NaOH neutralization can obtain alkyl diphenyl ether bissulfonate sodium, which is a special anionic surfactant containing disulfonic acid groups in the molecule, has good water solubility, and can be used in 20% strong acid It has good solubility and stability in strong alkali, inorganic salt and strong oxidant, and is widely used in emulsion polymerization, industrial cleaning, textile auxiliaries, oil field exploitation and other fields. [0003] The preparation of alkyl diphenyl ether is usually obtained by reacting olefins with diphenyl ether as an alkylating agent. The traditional catalysts include anhydrous aluminum trichloride, concentrated sulf...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/30B01J27/053C07C43/275
CPCC07C41/30B01J27/053C07C43/275Y02P20/584
Inventor 刘晓臣曹圣悌霍月青牛金平
Owner CHINA RES INST OF DAILY CHEM IND
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