Method for catalytically synthesizing n-propyl cinnamate based on choline chloride eutectic solvent

A technology of deep eutectic solvent and choline chloride, which is applied in chemical instruments and methods, preparation of organic compounds, physical/chemical process catalysts, etc., can solve problems such as long reaction time, large amount of alcohol, and poor storage durability. Achieve the effects of simple preparation method, mild reaction conditions, and low equipment corrosion

Pending Publication Date: 2022-03-01
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Wen Ruiming et al. (Synthetic Chemistry, 2001, 9(03): 269) used ferric ammonium sulfate as a catalyst to synthesize cinnamic acid series esters, which is easy to operate, mild in reaction, and does not corrode equipment, but the amount of alcohol is large and the reaction time is long; Wang et al. (Bioresource Technology, 2015, 198: 256) Using lipase TLIM to catalyze the esterification of cinnamic acid and ethanol to ethyl cinnamate, a higher yield can be obtained by using isooctane as the reaction medium. However, the industrial application of the enzyme is usually due to its Poor storage durability, difficulty in recovery and lack of reusability are hampered; 4 As a catalyst, it catalyzed the synthesis of n-propyl cinnamate. The influence of factors such as the ratio of acid to alcohol, reaction time, and the amount of ionic liquid on the reaction was investigated, and a higher yield was obtained, and the ionic liquid was reused 5 times. , its catalytic activity is basically unchanged, but 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

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Weigh 8.89g (0.06mol) of cinnamic acid and 10.82g (0.18mol) of n-propanol respectively, add the two into a three-necked flask, stir and heat to 73°C, then add 3.94g (20%) of catalyst into the three-necked flask ChCl-PTSA was reacted at this temperature, and the reaction time was 4 h; after the reaction was completed, the reaction solution was separated into water and oil phases through a separatory funnel while it was hot, and the water phase was vacuum-dried at 65°C to recover the catalyst; Distill the oil phase under atmospheric pressure to remove excess n-propanol, and then collect fractions through vacuum distillation (temperature 140-145°C, pressure 1.3kPa) to obtain a colorless and transparent oily liquid, which is the target product propyl cinnamate. Its yield is 87.19%.

Embodiment 2

[0018] Weigh 8.89g (0.06mol) of cinnamic acid and 7.21g (0.12mol) of n-propanol respectively, add the two into a three-necked flask, stir and heat to 93°C, then add 1.61g (10%) of catalyst into the three-necked flask ChCl-PTSA and react at this temperature, the reaction time is 2h; 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 65 ° C to recover the catalyst; The oil phase is first distilled at atmospheric pressure to remove excess n-propanol, and then distilled under reduced pressure (temperature 140-145°C, pressure 1.3kPa) to collect fractions to obtain a colorless and transparent oily liquid, which is the target product propyl cinnamate. The yield was 82.47%.

Embodiment 3

[0020] Weigh 8.89g (0.06mol) of cinnamic acid and 7.21g (0.12mol) of n-propanol respectively, add the two into a three-necked flask, stir and heat to 93°C, then add 4.83g (30%) of catalyst into the three-necked flask ChCl-PTSA and react at this temperature, the reaction time is 3h; after the reaction is completed, the reaction solution is separated into water and oil two phases through a separatory funnel while it is hot, and the water phase is vacuum-dried at 65 ° C to recover the catalyst; The oil phase is first distilled at atmospheric pressure to remove excess n-propanol, and then distilled under reduced pressure (temperature 140-145°C, pressure 1.3kPa) to collect fractions to obtain a colorless and transparent oily liquid, which is the target product propyl cinnamate. The yield was 90.75%.

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Abstract

The invention relates to a method for catalytically synthesizing n-propyl cinnamate based on a choline chloride eutectic solvent. The invention discloses a method for catalytically synthesizing n-propyl cinnamate based on a deep-eutectic solvent, which comprises the following steps of: performing esterification reaction by taking the deep-eutectic solvent choline chloride-p-toluenesulfonic acid monohydrate (ChCl-PTSA) as a catalyst and a solvent and taking cinnamic acid and propyl alcohol as raw materials, and performing phase separation, atmospheric distillation, reduced pressure distillation and the like to obtain the n-propyl cinnamate. The eutecticevaporate solvent can be used as a reaction solvent in the field of organic synthesis and can also be used as a catalyst to participate in chemical reaction, compared with traditional sulfuric acid and other catalysts, the eutecticevaporate solvent has the advantages of being environmentally friendly, free of pollution, easy to separate from a product, capable of being recycled and the like, the production cost is reduced, and meanwhile the requirement of a green synthesis process is met.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a method for catalytically synthesizing n-propyl cinnamate perfume, in particular to a method for catalytically synthesizing n-propyl cinnamate by using a deep eutectic solvent of choline chloride. Background technique [0002] N-propyl cinnamate has peach and apricot flavor, wine-like aroma, is widely used in food flavors and daily chemical flavors, and is a synthetic flavor with broad prospects. N-propyl cinnamate exists in natural styrax essence, soap essence, and oriental floral essence. It is often used as a fixative for essence, and is also used for blending sage perilla oil, citrus essence, etc. N-propyl cinnamate can also be used as a bacteriostatic agent, and has certain inhibitory effects on Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis (Henan Agricultural Science, 2013, 42(11): 158-160). [0003] Cinnamate is produced by esterification reaction b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/618B01J31/02
CPCC07C67/08B01J31/0271B01J31/0239B01J31/0225B01J2231/49C07C69/618
Inventor 曾作祥唐林茂孙莉孙静薛为岚
Owner EAST CHINA UNIV OF SCI & TECH
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