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CN111269115A - Preparation method of cinnamate in eutectic solvent - Google Patents

Preparation method of cinnamate in eutectic solvent Download PDF

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CN111269115A
CN111269115A CN202010121677.6A CN202010121677A CN111269115A CN 111269115 A CN111269115 A CN 111269115A CN 202010121677 A CN202010121677 A CN 202010121677A CN 111269115 A CN111269115 A CN 111269115A
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reaction
eutectic solvent
cinnamate
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尹大伟
孙嘉希
刘玉婷
李洁
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Shaanxi University of Science and Technology
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Abstract

The invention discloses a method for preparing cinnamate in a eutectic solvent. A mol of choline chloride and B mol of methanesulfonic acid (p-toluenesulfonic acid) are added into a dry three-neck flask, a eutectic solvent is obtained by stirring at room temperature, C mol of cinnamic acid and D mol of alcohol are added, the reaction is carried out at 50 ℃, and TLC monitoring is carried out until the reaction is complete. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the organic phase is evaporated to remove the solvent to obtain cinnamate, and the eutectic solvent can be obtained again after the water phase is recovered. The method has the advantages of no need of organic solvent, simple operation, high yield, high product purity, short reaction time, simple post-treatment, recyclable eutectic solvent, environmental protection and low cost, and has important significance for the synthesis and development of the compounds.

Description

Preparation method of cinnamate in eutectic solvent
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to a preparation method of cinnamate.
Background
The cinnamate compounds are the main ingredients of essences and flavors due to pleasant fruit and flower odor, and are widely applied to the cosmetic industry; meanwhile, the compound has unique physicochemical and biological activities: the antiviral activity, the ultraviolet resistance activity, the antioxidant activity, the enzyme resistance activity, the anticancer activity and the like, so that the compound has wide application and development values in medicines, foods and daily necessities.
The prior method for synthesizing the cinnamate compounds commonly adopts an inorganic acid catalytic esterification method, an organic acid catalytic esterification method, a heterogeneous catalytic esterification method, a high-pressure microwave synthesis method and the like. The inorganic acid catalytic method is generally obtained by directly esterifying corresponding alcohol under the catalysis of concentrated sulfuric acid, and has the defects of long reaction time, more byproducts, corrosion of equipment by concentrated sulfuric acid and the like. Organic acid catalysis, such as p-toluenesulfonic acid catalysis, overcomes the disadvantages of concentrated sulfuric acid catalysis, and has the advantages of short reaction time, high yield and high cost. The high-pressure microwave method can obviously shorten the time and has high yield but is difficult to realize industrial production. The nonaqueous phase enzymatic catalysis method has the advantages of mild condition, high catalytic activity, less by-products, environmental protection and the like, but has relatively high cost.
The eutectic solvent (DES) is a novel ionic liquid, has the advantages of the ionic liquid, namely no vapor pressure, high thermal stability, difficult volatilization, almost no environmental pollution in the preparation and use processes, and also has the advantages of simple preparation and low cost. In recent years, DES as a novel solvent, namely a catalyst, can improve reaction efficiency, is more environment-friendly, and has no corrosion to equipment, so DES is an effective way for replacing the traditional organic solvent and developing green synthesis.
The method for preparing the cinnamate, which is simple to operate, high in yield, green, environment-friendly and low in cost, has certain significance.
Disclosure of Invention
The invention aims to provide a preparation method of cinnamate, which has the advantages of no use of organic solvent, simple operation, high yield, high product purity, short reaction time, recyclable eutectic solvent, environmental protection and low cost.
In order to achieve the purpose, the invention adopts the technical scheme that:
the structural general formula of the cinnamate is as follows:
Figure BDA0002393158340000021
wherein R is-H, -CH3，-C2H5，-C3H7-n，-C3H7-i,-C4H9-n，-C4H9-i，-C5H11-n，-C5H11-i，-C6H13-n，-C6H13-i，-C8H17-n，-C8H17-i，-C10H23-n，,-C10H23-i，-C12H25-n，-C14H29-n.5.
The preparation method of the cinnamate comprises the following steps:
a mol of choline chloride and B mol of methanesulfonic acid (p-toluenesulfonic acid) are added into a dry three-neck flask, a eutectic solvent is obtained by stirring at room temperature, C mol of cinnamic acid and D mol of alcohol are added, the reaction is carried out at 50 ℃, and TLC monitoring is carried out until the reaction is complete. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the organic phase is evaporated to remove the solvent to obtain cinnamate, and the eutectic solvent can be obtained again after the water phase is recovered.
The structure of the cinnamic acid is as follows:
Figure BDA0002393158340000022
the structural general formula of the alcohol is shown as follows:
ROH
wherein R is-H, -CH3，-C2H5，-C3H7-n，-C3H7-i,-C4H9-n，-C4H9-i，-C5H11-n，-C5H11-i，-C6H13-n，-C6H13-i，-C8H17-n，-C8H17-i，-C10H23-n，,-C10H23-i，-C12H25-n，-C14H29-n.5.
And (3) monitoring by TLC, wherein the developing solvent used is a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 3: 1.
Compared with the prior art, the invention has the beneficial effects that:
the preparation method of cinnamate provided by the invention takes cinnamic acid and alcohol as raw materials, and takes choline chloride-methanesulfonic acid (p-toluenesulfonic acid) as a eutectic solvent as a solvent and a catalyst, so that the cinnamate can be prepared with high yield. The method has the advantages of no need of organic solvent, simple operation, high yield, high product purity, short reaction time, recyclable eutectic solvent, environmental protection, low cost and great application prospect.
Drawings
FIG. 1 is a FT-IR spectrum of methyl cinnamate prepared in example 1
FIG. 2 is a FT-IR spectrum of ethyl cinnamate prepared in example 2
FIG. 3 is a FT-IR spectrum of isopropyl cinnamate prepared in example 3
FIG. 4 is a FT-IR spectrum of butyl cinnamate prepared in example 4
FIG. 5 is the FT-IR spectrum of isobutyl cinnamate prepared in example 5
FIG. 6 is an FT-IR spectrum of isoamyl cinnamate prepared in example 6
Detailed Description
The following is a further detailed description of the invention with reference to examples:
the method takes cinnamic acid and alcohol as raw materials, and takes choline chloride-methanesulfonic acid (p-toluenesulfonic acid) as a eutectic solvent as a solvent and a catalyst to prepare the cinnamate. The reaction formula is as follows:
Figure BDA0002393158340000031
wherein R is-H, -CH3，-C2H5，-C3H7-n，-C3H7-i,-C4H9-n，-C4H9-i，-C5H11-n，-C5H11-i，-C6H13-n，-C6H13-i，-C8H17-n，-C8H17-i，-C10H23-n，,-C10H23-i，-C12H25-n，-C14H29-n.5.
Example 1 preparation of methyl cinnamate:
a dry three-necked flask was charged with 1.4g (10mmol) of choline chloride and 1.92(20mmol) of methanesulfonic acid, and stirred at room temperature to prepare a eutectic solvent, and then 0.148g (1mmol) of cinnamic acid and 0.038g (1.2mmol) of methanol were added to conduct a reaction at 50 ℃ with TLC monitoring until completion of the reaction. After the reaction is finished, the reaction liquid is poured into water, dichloromethane is used for extraction, the organic phase is evaporated to remove the solvent to obtain methyl cinnamate, and the water phase can be recovered to obtain the eutectic solvent again. The yield is 93.5 percent, and the m.p. is 30-32 ℃.
IR(KBr)ν:3072cm-1(ν＝C-H)，2940cm-1(νCH3)，1709cm-1(νC＝O)，1633,1445cm-1(νph)，1109cm-1(νC-O-C)，778cm-1(δph-H)。
EXAMPLE 2 preparation of Ethyl cinnamate
1.4g (10mmol) of choline chloride and 1.92(20mmol) of methanesulfonic acid were added to a dry three-necked flask, and the mixture was stirred at room temperature to prepare a eutectic solvent, and then 0.148g (1mmol) of cinnamic acid and 0.055g (1.2mmol) of ethanol were added to conduct a reaction at 50 ℃ and monitored by TLC until the reaction was completed. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the organic phase is evaporated to remove the solvent to obtain ethyl cinnamate, and the water phase can be recovered to obtain the eutectic solvent again. Ethyl cinnamate, light yellow transparent liquid, 91.4% yield.
IR(KBr)ν:3075cm-1(ν＝C-H)，2977cm-1(νCH3)，1718cm-1(νC＝O)，1633cm-1(νph)，1173cm-1(νC-O-C)，759cm-1(δph-H)。
Example 3 preparation of isopropyl cinnamate
1.4g (10mmol) choline chloride and 1.92(20mmol) methanesulfonic acid were added to a dry three-necked flask, and the mixture was stirred at room temperature to obtain a eutectic solvent, then 0.148g (1mmol) cinnamic acid and 0.072g (1.2mmol) isopropanol were added, and the reaction was carried out at 50 ℃ and monitored by TLC until the reaction was complete. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the organic phase is evaporated to remove the solvent to obtain isopropyl cinnamate, and the water phase can be recovered to obtain the eutectic solvent again. Isopropyl cinnamate, light yellow clear liquid, yield, 92.7%.
IR(KBr)ν:3071cm-1(ν＝C-H)；2977cm-1(νCH3)，1709cm-1(νC＝O)，1633cm-1(νph)，1182cm-1(νC-O-C)，759cm-1(δph-H)。
EXAMPLE 4 preparation of n-butyl cinnamate
A dry three-necked flask was charged with 1.4g (10mmol) of choline chloride and 3.44(20mmol) of p-toluenesulfonic acid, and stirred at room temperature to prepare a eutectic solvent, followed by addition of 0.148g (1mmol) of cinnamic acid and 0.088g (1.2mmol) of n-butanol, and reaction was carried out at 50 ℃ with TLC monitoring until completion of the reaction. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the organic phase is evaporated to remove the solvent to obtain n-butyl cinnamate, and the water phase can be recovered to obtain the eutectic solvent again. N-butyl cinnamate, a light yellow transparent liquid, yield, 90.1%.
IR(KBr)ν:3072cm-1(ν＝C-H)，2959cm-1(νCH3)，1718cm-1(νC＝O)，1633，1454cm-1(νph)，1173cm-1(νC-O-C)，769cm-1(δph-H)。
EXAMPLE 5 preparation of isobutyl cinnamate
A dry three-necked flask was charged with 1.4g (10mmol) of choline chloride and 3.44(20mmol) of p-toluenesulfonic acid, and stirred at room temperature to prepare a eutectic solvent, followed by addition of 0.148g (1mmol) of cinnamic acid and 0.088g (1.2mmol) of isobutanol, followed by reaction at 50 ℃ and TLC monitoring until completion of the reaction. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the organic phase is evaporated to remove the solvent to obtain n-butyl cinnamate, and the water phase can be recovered to obtain the eutectic solvent again. Isobutyl cinnamate, pale yellow transparent liquid, yield 90.9%.
IR(KBr)ν:3063cm-1(ν＝C-H)，2968cm-1(νCH3)，1709cm-1(νC＝O)，1633，1465cm-1(νph)，1173cm-1(νC-O-C)，769cm-1(δph-H)。
EXAMPLE 6 preparation of isoamyl cinnamate
A dry three-necked flask was charged with 1.4g (10mmol) of choline chloride and 3.44(20mmol) of p-toluenesulfonic acid, and stirred at room temperature to prepare a eutectic solvent, and then 0.148g (1mmol) of cinnamic acid and 0.107g (1.2mmol) of isoamyl alcohol were added to conduct a reaction at 50 ℃ and monitored by TLC until completion of the reaction. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the organic phase is evaporated to remove the solvent to obtain n-butyl cinnamate, and the water phase can be recovered to obtain the eutectic solvent again. Isoamyl cinnamate, a pale yellow transparent liquid, with a yield of 90.9%.
IR(KBr)ν:3063cm-1(ν＝C-H)，2959cm-1(νCH3)，1709cm-1(νC＝O)，1633cm-1(νph)，1128cm-1(νC-O-C)，769cm-1(δph-H)。
EXAMPLE 7 preparation of methyl cinnamate
A dry three-necked flask was charged with 1.4g (10mmol) of choline chloride and 3.44(20mmol) of p-toluenesulfonic acid, and stirred at room temperature to prepare a eutectic solvent, followed by addition of 0.148g (1mmol) of cinnamic acid and 0.038g (1.2mmol) of methanol, and reaction was carried out at 50 ℃ with TLC monitoring until completion of the reaction. After the reaction is finished, the reaction solution is poured into water, dichloromethane is used for extraction, the solvent is evaporated to obtain methyl cinnamate, and the eutectic solvent can be obtained again after the water phase is recovered. The yield is 93.3 percent, and the m.p. is 30-32 ℃.
IR(KBr)ν:3072cm-1(ν＝C-H)，2940cm-1(νCH3)，1709cm-1(νC＝O)，1633,1445cm-1(νph)，1109cm-1(νC-O-C)，778cm-1(δph-H)。
Example 8
The eutectic solvent can be obtained again by distilling the water phase. The effect of recycling the eutectic solvent (choline chloride, methanesulfonic acid) on the final yield was investigated using the synthesis example of methyl cinnamate and the results are shown in table 1.
TABLE 1 Effect of eutectic solvent recycle on yield
Figure BDA0002393158340000051
The result shows that the yield is not greatly influenced by recycling the eutectic solvent for five times, and the eutectic solvent still has a good catalytic effect on the reaction, which indicates that the method is simple, efficient and environment-friendly.
In summary, compared with the traditional process, the process does not use strong acid as a catalyst, and has the following advantages: 1. the requirement on equipment is low; 2. the operation is simple; 3. the yield is high; 4. no waste acid is generated after the reaction, so that the method is more environment-friendly; 5. the product has high purity and good quality.

Claims (7)

1. The application of a eutectic solvent choline chloride-methanesulfonic acid or a eutectic solvent choline chloride-p-toluenesulfonic acid in catalyzing the reaction of cinnamic acid and alcohol.
2. The preparation method of cinnamate is characterized by comprising the following steps:
cinnamic acid and alcohol react under the catalysis of a eutectic solvent choline chloride-methanesulfonic acid or a eutectic solvent choline chloride-p-toluenesulfonic acid to obtain the cinnamate.
3. The method according to claim 2, wherein the molar ratio of choline chloride to methanesulfonic acid and/or p-toluenesulfonic acid is 1 (1-2).
4. The method of claim 2, wherein the molar ratio of the cinnamic acid to the alcohol is 1 (1.1-1.2).
5. The method of claim 2, wherein the alcohol has the general structural formula:
ROH (1)；
r is-H, -CH3，-C2H5，-C3H7-n，-C3H7-i,-C4H9-n，-C4H9-i，-C5H11-n，-C5H11-i，-C6H13-n，-C6H13-i，-C8H17-n，-C8H17-i，-C10H23-n，,-C10H23-i，-C12H25-n，-C14H29-n。
6. The method of claim 2, comprising the steps of:
adding A mol of choline chloride and B mol of methanesulfonic acid and/or p-toluenesulfonic acid into a dry three-neck flask, and stirring at room temperature to obtain a eutectic solvent; then adding C mol of cinnamic acid and D mol of alcohol, carrying out reaction at 50 ℃, and monitoring by TLC until the reaction is complete; after the reaction is finished, pouring the reaction liquid into water, extracting with dichloromethane, evaporating an organic phase to remove the solvent to obtain cinnamate, and recovering a water phase to obtain a eutectic solvent again;
b is 1 (1-2); and C, D is 1 (1.1-1.2).
7. The method of claim 6, wherein the TLC monitors the reaction and is complete when the starting material spot disappears; the developing agent of the TLC is mixed solution of petroleum ether and ethyl acetate with the volume ratio of 3: 1.
CN202010121677.6A 2020-02-26 2020-02-26 Preparation method of cinnamate in eutectic solvent Pending CN111269115A (en)

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Cited By (4)

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Publication number Priority date Publication date Assignee Title
CN112812008A (en) * 2021-01-11 2021-05-18 大连理工大学 Method for preparing diacid diester compound under catalysis of deep eutectic solvent
CN113416136A (en) * 2021-06-21 2021-09-21 河南工业大学 Application of acidic ionic liquid in catalyzing reaction of cinnamic acid and benzyl alcohol to prepare benzyl cinnamate and method for preparing benzyl cinnamate
CN114160194A (en) * 2021-12-07 2022-03-11 中国科学院大连化学物理研究所 Preparation method and application of eutectic solvent for catalyzing alcohol dehydration
CN114656358A (en) * 2022-03-28 2022-06-24 大连理工大学 Method for preparing ester compound containing olefin under catalysis of deep eutectic solvent

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CN112645815A (en) * 2021-01-25 2021-04-13 华东理工大学 Preparation method for catalytically synthesizing methyl cinnamate based on eutectic solvent

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112812008A (en) * 2021-01-11 2021-05-18 大连理工大学 Method for preparing diacid diester compound under catalysis of deep eutectic solvent
CN113416136A (en) * 2021-06-21 2021-09-21 河南工业大学 Application of acidic ionic liquid in catalyzing reaction of cinnamic acid and benzyl alcohol to prepare benzyl cinnamate and method for preparing benzyl cinnamate
CN113416136B (en) * 2021-06-21 2023-12-22 河南工业大学 Application of acidic ionic liquid in catalyzing reaction of cinnamic acid and benzyl alcohol to prepare benzyl cinnamate and method for preparing benzyl cinnamate
CN114160194A (en) * 2021-12-07 2022-03-11 中国科学院大连化学物理研究所 Preparation method and application of eutectic solvent for catalyzing alcohol dehydration
CN114656358A (en) * 2022-03-28 2022-06-24 大连理工大学 Method for preparing ester compound containing olefin under catalysis of deep eutectic solvent
CN114656358B (en) * 2022-03-28 2023-02-14 大连理工大学 Method for preparing ester compound containing olefin under catalysis of deep eutectic solvent

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