Method for one-step synthesis of benzonitrile from benzaldehyde and ionic liquid type hydroxylammonium salt

An ionic liquid, benzaldehyde technology, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylic acid nitrile, etc., can solve the problems of unfriendly environment, complex production process of benzonitrile, equipment corrosion, etc. Friendly, achieves clean synthesis, and does not corrode equipment

Inactive Publication Date: 2017-09-15
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by the present invention is: in view of the current complex production process of benzonitrile, and the equipment corrosion and environmental unfriendly problems caused by the use of inorganic acid hydroxylamine salt, to provide a one-step synthesis of benzaldehyde and ionic liquid type hydroxylamine salt Benzonitrile method

Method used

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  • Method for one-step synthesis of benzonitrile from benzaldehyde and ionic liquid type hydroxylammonium salt
  • Method for one-step synthesis of benzonitrile from benzaldehyde and ionic liquid type hydroxylammonium salt

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Add benzaldehyde (3.6mmol), N,N,N-trimethyl-N-sulfobutylammonium bisulfate ionic liquid type hydroxylamine salt (5.4mmol) and zinc chloride catalyst (0.144mmol) into a 100mL three-necked flask , add 10mL of toluene and 2mL of N,N,N-trimethyl-N-sulfobutyl ammonium bisulfate ionic liquid, stir, reflux and condense, react at normal pressure and 100°C for 8h, then stop the reaction. The reaction solution was cooled to room temperature, and the supernatant was directly analyzed on a gas chromatograph. The result of the reaction was that the conversion rate of benzaldehyde was 87.9%, and the yield of benzonitrile was 87.1%.

Embodiment 2

[0035] The other steps are the same as in Example 1, except that the added N,N,N-trimethyl-N-sulfobutylammonium bisulfate ionic liquid type hydroxylamine salt is 4.32mmol, and the reaction result is that the conversion rate of benzaldehyde is 68.1 %, the yield of benzonitrile is 65.9%.

Embodiment 3

[0037] Other steps are the same as in Example 1, except that the added N,N,N-trimethyl-N-sulfobutyl ammonium bisulfate ionic liquid type hydroxylamine salt is 4.68mmol, and the reaction result is that the conversion rate of benzaldehyde is 73.6 %, the yield of benzonitrile is 70.3%.

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Abstract

The invention provides a method for one-step synthesis of benzonitrile from benzaldehyde and ionic liquid type hydroxylammonium salt. The method comprises the following steps: adding benzaldehyde, zinc chloride, ionic liquid and ionic liquid type hydroxylammonium salt into a reactor; then adding an organic solvent; carrying out stirring and reflux condensation; and carrying out a reaction at normal pressure and a temperature of 90 to 130 DEG C for 2 to 10 h so as to obtain benzonitrile, wherein the ionic liquid type hydroxylammonium salt is N,N,N-trimethyl-N-sulfobutylammonium bisulfate ionic liquid type hydroxylammonium salt, 1-sulfobutyl-3-methylimidazole bisulfate ionic liquid type hydroxylammonium salt and 1-sulfobutylpyridine bisulfate ionic liquid type hydroxylammonium salt. According to the invention, two-step reactions are integrated in one reactor; the method is simple in process and convenient to operate; the ionic liquid has good stability as a catalyst; synthesized benzonitrile is easy to separate; and the ionic liquid conjugated with the ionic liquid type hydroxylamine salt can be used as a catalyst and solvent in the reactions.

Description

technical field [0001] The invention relates to the synthesis of organic chemical products, in particular to a process for synthesizing benzonitrile in one step from benzaldehyde and ionic liquid hydroxylamine salt. Background technique [0002] Benzonitrile is a kind of important organic chemical intermediate, is widely used in the synthesis of benzoic acid, benzylamine, benzamide, pesticide and dyestuff (fuel and chemical industry, 2001,32 (5): 256-258), more It is an intermediate in the synthesis of advanced paint benzomelamine. Due to its good solubility, it can dissolve various inorganic and organic substances, and benzonitrile can also be used as a dyeing aid for acrylic fibers, as well as high-boiling organic solvents for organic synthesis, paints, printing inks and resins (industrial catalysis, 2003, 11(7): 29-31). [0003] Industrially, benzonitrile is mainly prepared by ammoxidation of toluene, that is, toluene is passed through a vanadium-chromium catalyst, and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/00C07C255/50
CPCC07C253/00C07C255/50Y02P20/54
Inventor 王延吉王停停李志会张东升徐元媛赵新强王淑芳
Owner HEBEI UNIV OF TECH
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