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Method for catalyzing benzylation reaction by means of lignin-based solid acid

A technology of lignin-based and sodium lignosulfonate, which is applied in the field of lignin-based solid acid catalyzed benzylation reaction, can solve the problems of catalyst activity, water resistance, reusability and environmental friendliness being difficult to take into account, and achieves cost Low, source-rich effects

Active Publication Date: 2019-09-24
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to effectively utilize sodium lignin sulfonate, a by-product of the paper industry, to develop a low-cost biomass-based catalyst, and to solve the problems of catalyst activity, water resistance, reusability and environmental friendliness in the prior art of benzylation reaction It is difficult to balance the problem, so as to provide a new environment-friendly method that utilizes the structural characteristics of lignin to introduce strong acidity and efficiently catalyze the benzylation reaction of benzyl alcohol route

Method used

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  • Method for catalyzing benzylation reaction by means of lignin-based solid acid
  • Method for catalyzing benzylation reaction by means of lignin-based solid acid
  • Method for catalyzing benzylation reaction by means of lignin-based solid acid

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Experimental program
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Effect test

Embodiment 1

[0019] Example 1 strong Preparation of Acidic Lignin-Based Solid Acid A

[0020] at 5°C·min -1 Heating rate, 80mL·min -1 flow rate N 2 Under the atmosphere, the dried sodium lignosulfonate (SLS) was carbonized in a tube furnace at 400 °C for 1 h, and cooled to room temperature to obtain lignin carbon SLC 400,1 ; by 10mL 浓硫酸 / g 木质素碳 The ratio of lignin carbon to SLC 400,1 and concentrated sulfuric acid in a three-necked flask, N 2 400r·min under atmosphere -1 Stir mechanically, react at 150°C for 10 hours, add 50mL of hot water above 80°C to filter, wash with hot water above 80°C until neutral, and dry in a vacuum oven at 50°C for 4 hours to obtain strong Acidic lignin-based solid acid A.

[0021] attached figure 1 The indicated FT-IR(KBr,v / cm -1 ) spectrum, SLS at 3405cm -1 The broad band observed at is attributed to the -OH group hydrogen-bonded to an adjacent oxygen or sulfonic acid; 2939cm -1 and 2839cm -1 SLS-CH 2 - stretching vibration; 1715cm -1 Indicat...

Embodiment 2

[0024] according to n 苯环化合物 :n 苯甲醇 =10 feed ratio Get p-xylene and benzyl alcohol in the reaction flask, then press 2.5mL 苯甲醇 / g 催化剂 The consumption of dropping into the strong prepared in embodiment 1 Acidic lignin-based solid acid catalyst A was reacted with magnetic stirring at 150° C. for 2 hours. After the reaction was completed, it was cooled and centrifuged, and the upper organic phase was taken for gas chromatography analysis. The catalytic results are shown in Table 1.

[0025] attached image 3 Shown is the macroscopic state diagram of the system after the catalytic reaction and centrifugation in Example 2, and the catalyst A can be effectively separated by centrifugation after the reaction.

Embodiment 3

[0027] according to n 苯环化合物 :n 苯甲醇 =10 feed ratio Get p-xylene and benzyl alcohol in the reaction flask, then press 2.5mL 苯甲醇 / g 催化剂 The consumption of dropping into the strong prepared in embodiment 1 Acidic lignin-based solid acid catalyst A was reacted with magnetic stirring at 150°C for 0.15h. After the reaction was completed, it was cooled and centrifuged, and the upper organic phase was taken for gas chromatography analysis. The catalytic results are shown in Table 1.

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Abstract

The invention relates to a method for catalyzing a Friedel-Crafts benzylation reaction of a benzene ring compound by means of a lignin-based solid acid, in particular to a method for adopting a strong-acidity solid acid obtained by carbonizing and sulfonating sodium lignin sulfonate as a catalyst for catalyzing a clean benzylation reaction of a benzene ring compound and benzyl alcohol, and belongs to the technical field of production of fine chemicals. According to the method for adopting the strong-acidity solid acid obtained by carbonizing and sulfonating the sodium lignin sulfonate as the catalyst for catalyzing the clean benzylation reaction of the benzene ring compound and the benzyl alcohol, the derivative product sodium lignin sulfonate of by-product black liquor of the papermaking industry is used as a raw material, and through carbonizing and sulfonating treatment, the strong-acidity lignin-based solid acid catalyst is produced, and efficiently catalyzes the clean benzylation reaction of the benzene ring compound of benzene, methylbenzene, p-xylene, m-xylene, o-xylene, mesitylene, anisole, nitrobenzene, chlorobenzene or the like and the benzyl alcohol. The method is simple in reaction process, the industrial by-product is fully used for reducing the catalyst cost, and the catalyst has high catalytic activity and water resistance and good recycling performance at the same time, so that a novel efficient environment-friendly path is provided for the benzylation reaction of a benzyl alcohol route.

Description

technical field [0001] The invention relates to a method for catalyzing the Friedel-Crafts benzylation reaction of a benzene ring compound with a lignin-based solid acid. Specifically, it is obtained by carbonization and sulfonation of sodium lignosulfonate The acidic solid acid is used as a catalyst to catalyze the clean benzylation reaction of benzene ring compound and benzyl alcohol. Background technique [0002] Benzylation of aromatic compounds is one of the important reactions in organic chemistry, and the generated diarylmethane and its derivatives are key pharmaceutical intermediates or fine chemicals (Iovel I, Mertins K, Kischel J, et al.AngewandteChemie International Edition, 2005, 44(25): 3913-3917.; Bandini M, Melloni A, Umani-Ronchi A. Angewandte Chemie International Edition, 2004, 43(5): 550-556.; Liu Z T, Sun Z, Liu Z W, et al. J. Appl. Polym. Sci., 2008, 107(3):1872-1878.). Benzylation of aromatic compounds typically uses benzyl chloride as reagent, and h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/06B01J27/02C07C1/20C07C15/16C07C17/263C07C25/18C07C201/12C07C205/06C07C41/30C07C43/205
CPCB01J27/02B01J31/069C07C1/20C07C17/263C07C41/30C07C201/12C07C15/16C07C25/18C07C205/06C07C43/205
Inventor 袁冰解从霞陈祥云于凤丽于世涛
Owner QINGDAO UNIV OF SCI & TECH
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