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Synthetic technology of diphenylmethane dicarbamate by adopting Bronsted-Lewis acidic ionic liquid catalysis

A technology of methyl dicarbamate and methyl phenylcarbamate, which is applied in the field of diphenylmethane dicarbamate synthesis technology catalyzed by Br*nsted-Lewis double-acidic ionic liquid, can solve the problem that the catalyst is difficult to be reused and the product Low yield and other problems, to achieve the effect of easy preparation and high catalytic activity

Active Publication Date: 2012-06-27
HEBEI UNIV OF TECH
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  • Application Information

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Problems solved by technology

[0005] The invention solves the problems in the prior art that the product yield is low, the use of organic solvents, the catalyst is difficult to reuse, etc., thereby providing Synthesis reaction process of diphenylmethane dicarbamate methyl ester catalyzed by bis-acidic ionic liquid

Method used

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  • Synthetic technology of diphenylmethane dicarbamate by adopting Bronsted-Lewis acidic ionic liquid catalysis
  • Synthetic technology of diphenylmethane dicarbamate by adopting Bronsted-Lewis acidic ionic liquid catalysis
  • Synthetic technology of diphenylmethane dicarbamate by adopting Bronsted-Lewis acidic ionic liquid catalysis

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preparation example Construction

[0033] used in the present invention The preparation method of bis-acidic ionic liquid:

[0034] With reference to the technical route provided by Liu et al. (Catalysis Communications, 2008, 9: 2030-2034), the cations can be synthesized as 1-(4-sulfonic acid)butyltriethylammonium, 1-(3-sulfonic acid)propyltriethylammonium Ammonium butyl ammonium, 1-(4-sulfonic acid) butyl tripropyl ammonium, 1-(3-sulfonic acid) propyl tripropyl ammonium, 1-(4-sulfonic acid) butyl tributyl ammonium and 1- (3-sulfonic acid)propyltributylammonium, anion is AlCl 4 - , ZnCl 3 - , FeCl 4 - , SnCl 3 - and CuCl 2 - of Biacidic ionic liquid; reference to the method provided in Liu et al. 1-(3-sulfonic acid)propyl-3-ethylimidazole, 1-(4-sulfonic acid)butyl-3-methylimidazole, 1-(3-sulfonic acid)propyl-3-methylimidazole , 1-(3-sulfonic acid) propylpyridine and 1-(4-sulfonic acid) butylpyridine, the anion is AlCl 4 - , ZnCl 3 - , FeCl 4 - , SnCl 3 - and CuCl 2 - of Biacidic ionic...

Embodiment 1

[0036] Dissolve 1 mol of imidazole in 150 ml of acetone, add 1.1 mol of diethyl maleate, react at reflux temperature for 24 hours, distill under reduced pressure, distill off the solvent and unreacted raw materials to obtain 1-(2-butanedioic acid diethyl ester group) imidazole, then at 40°C, 1-(2-succinate diethyl) imidazole and 1,4-butane sultone were mixed in a molar ratio of 1:1.1, reacted for 20h, washed with ether, After drying, 1-(2-diethylsuccinate)-3-(4-sulfonate)butylimidazolium zwitterion was obtained. Take 0.5mol of the above-mentioned zwitterions and dissolve them in 100ml of water, add 3mol of concentrated hydrochloric acid (36.5% in mass concentration) dropwise, react at 80°C for 6h, and distill under reduced pressure (vacuum degree 0.01MPa, the following steps and examples are the same as the vacuum degree ) to remove water and unreacted hydrochloric acid to obtain 1-(2-butanedioic acid)-3-(4-sulfonic acid) butylimidazole chloride salt, then get 0.22mol zinc ace...

Embodiment 2

[0044] Dissolve 1 mol of imidazole in 150 ml of acetone, add 1 mol of diethyl maleate, react at reflux temperature for 12 hours, after vacuum distillation, distill off the solvent and unreacted raw materials to obtain 1-(2-butanedioic acid diethyl ester group) imidazole, then at 80°C, 1-(2-succinate diethyl) imidazole and 1,4-butane sultone were mixed in a molar ratio of 1:1, reacted for 10h, washed with ether, After drying, 1-(2-diethylsuccinate)-3-(4-sulfonate)butylimidazolium zwitterion was obtained. Take 0.5 mol of the above-mentioned zwitterions and dissolve them in 100 ml of water, add 1.5 mol of concentrated hydrochloric acid (36.5% in mass concentration) dropwise, react at 130°C for 1 h, and distill off water and unreacted hydrochloric acid under reduced pressure to obtain 1-(2- Succinic acid)-3-(4-sulfonic acid) butylimidazole chloride, then take 0.2mol of zinc acetate and dissolve it in 100ml of water, add 0.2mol of 1-(2-butanedioic acid)-3-(4-sulfonic acid ) butyli...

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Abstract

The invention discloses a method for synthesizing diphenylmethane dicarbamate by adopting Bronsted-Lewis acidic ionic liquid catalysis. The method is any one of the following two methods: method A: successively adding methyl phenyl carbamate, a Bronsted-Lewis acidic ionic liquid and formaldehyde in a reactor, reacting for 0.5-5 h at a reaction temperature of 50-90 DEG C to finally obtain diphenylmethane dicarbamate; or method B: successively adding dimethyl carbonate, aniline, formaldehyde and the Bronsted-Lewis acidic ionic liquid in the reactor, reacting for 4-10 h at a reaction temperature of 150-200 DEG C to finally obtain diphenylmethane dicarbamate. The Bronsted-Lewis acidic ionic liquid used in the invention is easy to prepare, combines the functions of solvent and catalyst, and has high catalytic activity, and the product yield can reach more than 99 %.

Description

technical field [0001] The invention belongs to the application of green technology and green reaction medium, specifically adopting Biacidic Ionic Liquid Catalyzed Synthesis of Methyl Diphenylmethane Dicarbamate. Background technique [0002] Ionic liquids are regarded as potential green reaction media due to their advantages such as wide liquid range, good solubility, non-volatility, and high thermal stability. Acidic ionic liquids can be divided into Acid ionic liquids and Lewis acid ionic liquids, the former basically functionalizes cations with sulfonic acid groups to make ionic liquids present Acid, the typical representative of the latter is chloroaluminate acid ionic liquid, and later developed to include anion as FeCl 4 - , ZnCl 3 - , SnCl 3 - Such a large family of ionic liquids. Acid ionic liquids and Lewis acid ionic liquids can be used to catalyze conventional Acid and Lewis acid catalyzed reactions, such as esterification, transesterification, al...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/28C07C269/06C07C269/04B01J31/04C07D233/60
Inventor 赵新强康丽娟安华良王延吉
Owner HEBEI UNIV OF TECH
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