Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for synthesizing methyl cinnamate based on eutectic solvent catalyst

A technology of deep eutectic solvent and methyl cinnamate, applied in chemical instruments and methods, preparation of organic compounds, physical/chemical process catalysts, etc., can solve problems such as corrosion equipment, large amount of alcohol, long reaction time, etc., to achieve The effects of mild reaction conditions, less corrosive equipment, and simple preparation methods

Pending Publication Date: 2021-03-26
EAST CHINA UNIV OF SCI & TECH
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The traditional synthesis method of methyl cinnamate is to use cinnamic acid and methanol as raw materials, and carry out esterification reaction under the catalysis of inorganic acid such as concentrated sulfuric acid. However, there are many side reactions and the yield is low, and concentrated sulfuric acid is strongly corrosive It will corrode the equipment, so it is necessary to seek a more green and environmentally friendly process
In the current research on catalysts for the synthesis of cinnamate esters, Wen Ruiming et al. (Synthetic Chemistry, 2001, 9(03): 269) used ammonium ferric sulfate as a catalyst to synthesize cinnamate series esters, which is easy to operate, mild in reaction, and does not corrode equipment, but The amount of alcohol used is large and the reaction time is long; Wang et al. (Bioresource Technology, 2015, 198: 256) used lipase TLIM to catalyze the esterification of cinnamic acid and ethanol to synthesize ethyl cinnamate, and a higher yield could be obtained by using isooctane as the reaction medium. However, the industrial application of enzymes is usually hindered by its poor storage durability, difficulty in recovery and lack of reusability; Chinese patent CN102701973A proposes to prepare a microemulsion after mixing an ionic liquid with water, and then add it to the Palladium chloride solution is prepared into a nano-scale palladium catalyst, and then iodobenzene, methyl acrylate and triethylamine undergo a HECK reaction to prepare methyl cinnamate. The catalyst preparation process of this method is complicated, and the ionic liquid is expensive, which is not conducive to its industrial application

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Weigh 7.41g (0.05mol) of cinnamic acid and 6.40g (0.2mol) of methanol respectively, add the two into a three-necked flask, stir and heat to 64°C, then add 2.76g (20%) catalyst BTAC- PTSA and react at this temperature, the reaction time is 4 h; after the reaction, the reaction solution is separated into water and oil phases through a separatory funnel while it is hot, and the water phase is vacuum-dried at 50°C to recover the catalyst; the oil phase Pour it into a beaker while it is hot and place the beaker in a 40°C water bath, add an appropriate amount of 4% sodium carbonate solution to weak alkalinity (pH=7~8) under constant stirring, let stand to separate layers, and remove the water phase; Add three times the volume of 5°C deionized water to the oil phase under constant stirring to precipitate crystals, then suction filter and wash with deionized water until the filtrate is neutral to obtain a white or light yellow solid, and after drying, the target product methyl c...

Embodiment 2

[0019] Weigh 7.41g (0.05mol) of cinnamic acid and 4.81g (0.15mol) of methanol respectively, add the two into a three-necked flask, stir and heat to 76°C, then add 1.23g (10%) catalyst BTAC- PTSA was heated and refluxed at this temperature for 2 hours. After the reaction was completed, the reaction solution was separated into water and oil phases through a separatory funnel while it was still hot, and the water phase was vacuum-dried at 50°C to recover the catalyst; Pour the oil phase into a beaker while it is hot and place the beaker in a water bath at 50°C, add an appropriate amount of 4% sodium carbonate solution to weak alkalinity (pH=7~8) under constant stirring, let stand to separate layers, and remove water phase; the oil phase was added with three volumes of deionized water at 5°C under constant stirring to precipitate crystals, then suction filtered and washed with deionized water until the filtrate was neutral to obtain a white or light yellow solid, and after drying, ...

Embodiment 3

[0021] Weigh 7.41g (0.05mol) of cinnamic acid and 4.81g (0.15mol) of methanol respectively, add the two into a three-necked flask, stir and heat to 76°C, then add 3.66g (30%) catalyst BTAC- PTSA and heat reflux reaction at this temperature, the reaction time is 3h; after the reaction, the reaction solution is separated into water and oil phases through a separatory funnel while it is hot, and the water phase is vacuum-dried at 50°C to recover the catalyst; Pour the phase into a beaker while it is hot and place the beaker in a 45°C water bath, add an appropriate amount of 4% sodium carbonate solution to weakly alkaline (pH=7~8) under constant stirring, let it stand for layers, and remove the water phase Add three times the volume of 5°C deionized water to the oil phase under constant stirring to precipitate crystals, then suction filter and wash with deionized water until the filtrate is neutral to obtain a white or light yellow solid, and after drying, the target product methyl...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for catalytically synthesizing methyl cinnamate by adopting a benzyltrimethylammonium chloride eutectic solvent, which comprises the following steps of: performing esterification reaction by taking an acidic eutectic solvent benzyltrimethylammonium chloride p-toluenesulfonic acid (BTAC-PTSA) as a catalyst and cinnamic acid and methanol as raw materials; and carrying out phase separation, neutralization, crystallization purification and other processes to obtain methyl cinnamate. The eutectic solvent used in the invention has an atom utilization rate of 100% inthe preparation process, and has the advantages of mild reaction conditions, small corrosivity to equipment, easy recovery, reusability and the like compared with traditional catalysts such as sulfuric acid and the like.

Description

technical field [0001] The invention relates to a preparation method for synthesizing spice methyl cinnamate, which belongs to the field of organic chemical synthesis, and in particular to a method for catalytically synthesizing methyl cinnamate by using a benzyltrimethylammonium chloride type deep eutectic solvent. Background technique [0002] Methyl cinnamate, also known as β-phenylmethyl acrylate, has a cherry-like aroma, which can be produced and released by strawberries during the ripening process. my country's GB-2760-2014 stipulates that it is an edible spice that is allowed to be used. Methyl cinnamate can be used as a deodorant, and has been widely used in the deployment of oriental floral essences, soaps, detergents, etc. In the pharmaceutical industry, it can be used as an intermediate in pharmaceutical organic synthesis. In addition, it can also play a role in sunscreen products. With the improvement of people's living standards, it is believed that its dem...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/618B01J31/02
CPCB01J31/0239B01J31/0271B01J2231/49C07C67/08C07C69/618
Inventor 曾作祥唐林茂郭媛赵凝瑞薛为岚孙莉
Owner EAST CHINA UNIV OF SCI & TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com