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Method for preparing olefin-containing ester compound under catalysis of deep eutectic solvent

A technology for deep eutectic solvents and ester compounds, which is applied in the field of deep eutectic solvent catalyzed preparation of olefin-containing ester compounds, can solve the problems of difficult recovery, corrosion side reactions, poor catalyst stability, etc. Catalytic efficiency, good catalytic effect

Active Publication Date: 2022-06-24
DALIAN UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, sulfuric acid catalyzed synthesis is mostly used to prepare olefin-containing ester compounds, which has the advantages of high yield and low cost, but there are also serious environmental pollution and difficult recovery. There are many problems such as serious corrosion and many side reactions; in addition, some people use solid acid catalysts or molecular sieve catalysts to catalyze esterification reactions, which have high catalytic activity and can be recycled, but these two types of catalysts are poor in stability, easy to deactivate, and recycled. The number of times is limited, which limits its industrial application; ionic liquids overcome the disadvantages of easy inactivation, the reaction temperature is not high, the recovery is simple, and they are still active after recycling many times, but they also have high cost, certain toxicity, and biodegradation Its industrial application is limited by the limitations of poor properties and relatively complicated synthesis [(a) RezaFareghi-Alamdari, MehriNadiriNiri, HassanHazarkhani. Journal of Molecular Liquids, 2017, 227. (b) Lin Dan. New progress in research on esterification catalysts[J]. Chemical Industry, 2017,38(02):41-45], so there are many deficiencies in the existing synthesis method of olefin-containing ester compounds, so exploring green, efficient, environmentally friendly and recyclable catalysts in esterification important in the reaction

Method used

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  • Method for preparing olefin-containing ester compound under catalysis of deep eutectic solvent
  • Method for preparing olefin-containing ester compound under catalysis of deep eutectic solvent
  • Method for preparing olefin-containing ester compound under catalysis of deep eutectic solvent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Example 1: Synthesis of Lauryl Sorbate

[0062] In a 100mL single-neck flask, add oxalic acid (7.2g, 0.08mol), tetraethylammonium chloride (13.3g, 0.08mol), p-tert-butylcatechol (0.14g, 1%) and stir at 80°C for 30min until The system became a colorless and transparent liquid to obtain a deep eutectic solvent, and then sorbic acid (10.76g, 0.096mol) and lauryl alcohol (18.2mL, 0.08mol) were added, and the reaction was carried out at 90 ° C for 8h. After the reaction, the layers were separated and cooled. The organic layer was taken away to be lauryl sorbate with a yield of 83%. New raw materials are added to the remaining deep eutectic solvent layer, and the above process is repeated, and the yield is still more than 80% after the deep eutectic solvent is recycled for 10 times.

[0063] Lauryl Sorbate

[0064] colorless liquid; 1 H NMR (400MHz, Chloroform-d) δ 7.25 (dd, J=15.4, 10.1 Hz, 1H), 6.23–6.09 (m, 2H), 5.78 (d, J=15.4 Hz, 1H), 4.13 (t, J=6.7Hz, 2H), 1.85 (d...

Embodiment 2

[0065] Example 2: Synthesis of Lauryl Cinnamate

[0066] In a 100mL single-neck flask, add citric acid (15.4g, 0.08mol), choline chloride (5.6g, 0.08mol), 3,5-di(tert-butyl)catechol (0.18g, 1%) Stir at 80°C for 30min until the system becomes a colorless and transparent liquid to obtain a deep eutectic solvent, then add cinnamic acid (14.2g, 0.096mol), lauryl alcohol (18.2mL, 0.08mol), and react at 90°C for 8h, the reaction After finishing layering, taking away the organic layer after cooling is lauryl cinnamate, the yield is 98%, adding new raw materials in the remaining deep eutectic solvent layer, and repeating the above process, the deep eutectic solvent is recycled 10 times The post-yield is still over 90%.

[0067] Lauryl Cinnamate

[0068] colorless liquid; 1 H NMR (400MHz, Chloroform-d) δ 7.71 (d, J=16.0Hz, 1H), 7.56–7.53 (m, 2H), 7.42–7.38 (m, 3H), 6.47 (d, J=16.0Hz, 1H), 4.23 (t, J=6.7Hz, 2H), 1.76–1.69 (m, 2H), 1.34–1.29 (m, 18H), 0.97–0.88 (t, J=6.5Hz, 3H); 1...

Embodiment 3

[0069] Example 3: Synthesis of Dilauryl Maleate

[0070] In a 100mL single-necked flask, add trichloroacetic acid (13.1g, 0.08mol), tetrabutylammonium chloride (11.1g, 0.04mol), bisphenol A (0.1g, 1%) and stir at 50°C for 30min until the system It became a colorless and transparent liquid to obtain a deep eutectic solvent, and then maleic acid (4.65g, 0.04mol) and lauryl alcohol (22.7mL, 0.1mol) were added, and the reaction was carried out at 90 ° C for 8h. After the reaction, the layers were separated. The upper organic layer is distilled under reduced pressure (-100KPa) at 110°C to steam lauryl alcohol and reclaim to obtain the product dilauryl maleate yield 92%, and the steamed lauryl alcohol is dropped into a deep eutectic solvent to continue the reaction, Adding new raw materials and repeating the above process, the yield is still more than 80% after the deep eutectic solvent is recycled for 10 times.

[0071] Dilauryl Maleate

[0072] colorless liquid; 1 H NMR (400M...

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Abstract

The invention belongs to the technical field of organic synthesis, and discloses a method for preparing an olefin-containing ester compound through catalysis of a deep eutectic solvent, which comprises the following steps: by taking olefin-containing carboxylic acid or olefin-containing carboxylic ester and an alcohol compound as raw materials, and taking a three-component deep eutectic solvent as a catalyst, a polymerization inhibitor and a solvent, carrying out a reaction to prepare the olefin-containing ester compound. And carrying out esterification or ester exchange reaction under a heating condition to generate ester containing olefin. The selected deep eutectic solvent is environmentally friendly and easy to prepare, components are cheap and easy to recover, the preparation method is easy and convenient to operate and separate, a water-carrying agent is not needed, the deep eutectic solvent can be recycled for multiple times, and the yield is high.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and provides a new method for preparing olefin-containing ester compounds catalyzed by deep eutectic solvent. Background technique [0002] Olefin-containing ester compounds are widely used in organic synthesis, plasticizers, pour point depressants, etc. For example, methyl methacrylate is a monomer of polymethyl methacrylate, mainly used in the manufacture of plexiglass, coatings, Lubricating oil additives and plastics, etc. [Li Min. MMA Market Analysis and Prospects [J]. Economic Analysis of China Petroleum and Chemical Industry, 2019(09): 56-58]; Neopentyl glycol dimethacrylate has low viscosity and high The characteristics of boiling point, as a cross-linking monomer used in coatings, inks, instant glue, rubber products, building materials, etc. [Bai Yunfei. Research on the green catalytic synthesis process of neopentyl glycol dimethacrylate [D]. Tianjin University, 2007]; Isooctyl methacryl...

Claims

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Application Information

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IPC IPC(8): C07C67/08C07C69/54C07C69/60C07C69/587C07C69/618C07C69/533C07C69/653C07C67/03C07D301/00C07D303/16B01J31/02B01J31/04
CPCC07C67/08C07C67/03C07D301/00C07D303/16B01J31/0239B01J31/0271B01J31/04B01J2231/49C07C2601/14C07C69/54C07C69/60C07C69/587C07C69/618C07C69/533C07C69/653
Inventor 于晓强李艳艳包明
Owner DALIAN UNIV OF TECH
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