CN113861016B - Cyanoethyl alkyl imidazole gallate ionic liquid and preparation method and application thereof - Google Patents

Cyanoethyl alkyl imidazole gallate ionic liquid and preparation method and application thereof Download PDF

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CN113861016B
CN113861016B CN202111119004.8A CN202111119004A CN113861016B CN 113861016 B CN113861016 B CN 113861016B CN 202111119004 A CN202111119004 A CN 202111119004A CN 113861016 B CN113861016 B CN 113861016B
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ionic liquid
cyanoethyl
gallate
alkyl imidazole
cyanoethyl alkyl
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CN113861016A (en
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王霜
李瑞志
李法社
隋猛
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Kunming University of Science and Technology
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    • C10L1/00—Liquid carbonaceous fuels
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    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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Abstract

The invention discloses cyanoethyl alkyl imidazole gallate ionic liquid and a preparation method and application thereof, wherein the cyanoethyl alkyl imidazole gallate ionic liquid comprises cyanoethyl alkyl imidazole cations and gallic acid anions, gallic acid, deionized water and cyanoethyl alkyl imidazole are mixed and then stirred for reaction under an oil bath, and after the reaction is finished, the product, namely the cyanoethyl alkyl imidazole gallate ionic liquid is obtained by washing and rotary steaming for removing water, and the cyanoethyl alkyl imidazole gallate ionic liquid can be used as a biodiesel antioxidant and is used for solving the problems of poor oil solubility and undesirable antioxidant effect of the conventional biodiesel antioxidant.

Description

Cyanoethyl alkyl imidazole gallate ionic liquid and preparation method and application thereof
Technical Field
The invention relates to a room-temperature ionic liquid, a preparation method and an application thereof, in particular to a cyanoethyl alkyl imidazole gallate ionic liquid, a preparation method and an application thereof, and belongs to the field of chemical industry.
Background
The biodiesel is a novel degradable, renewable and environment-friendly biofuel, can be used as a substitute of the traditional fossil fuel, and has the characteristics of good environmental protection performance, good engine starting performance, good fuel performance, wide raw material source, renewability and the like. In recent years, many researches prove that after the biodiesel is combusted, the hydrocarbon is reduced by 55-60%, the particulate matter is reduced by 20-50%, the CO is reduced by more than 45%, and the polycyclic aromatic hydrocarbon is reduced by 75-85%.
Although biodiesel as a substitute energy source for petroleum diesel shows good fuel performance, the components of the biodiesel have poor oxidation resistance due to a large number of carbon-carbon double bonds, and antioxidants in the market at present are not developed for the biodiesel specially, so that various antioxidants can be used for the oxidation resistance of the biodiesel, but the oil-soluble performance of the biodiesel is poor.
Ionic liquids (or ionic liquids) are liquids composed of ions, and in ionic compounds, the force between cations and anions is coulomb force, the magnitude of which is related to the charge quantity and radius of the cations and anions, and the larger the ionic radius is, the smaller the force between them is, and the lower the melting point of the ionic compound is. Certain ionic compounds have bulky anions and cations and loose structures, resulting in low forces between them, such that the melting point is close to room temperature. At present, the ionic liquid is widely applied to the fields of chemical synthesis, chemical separation, electrochemistry and the like, obtains good research results and has a larger development prospect.
Disclosure of Invention
The invention provides a room temperature ionic liquid, namely cyanoethyl alkyl imidazole gallate ionic liquid and a preparation method thereof, and the ionic liquid is used as an antioxidant of biodiesel to improve the oil solubility and the oxidation resistance of the biodiesel antioxidant.
The technical scheme of the invention is as follows:
the invention provides cyanoethyl alkyl imidazole gallate ionic liquid which comprises 1- (2-cyanoethyl) -2-undecylimidazole cations and gallic acid anions, wherein cyanoethyl alkyl imidazole is 1- (2-cyanoethyl) -2-undecylimidazole.
The invention also provides a preparation method of the cyanoethyl alkyl imidazole gallate ionic liquid, which comprises the following specific steps:
(1) Putting gallic acid into a round bottom flask, adding a small amount of deionized water and cyanoethyl alkyl imidazole, wherein the molar weights of the cyanoethyl alkyl imidazole and the gallic acid are equal, and stirring for reaction under oil bath;
(2) And (2) after the reaction in the step (1) is finished, washing with water for 3 times, and then removing water by rotary evaporation to obtain the product, namely the cyanoethyl alkyl imidazole gallate ionic liquid.
The oil bath temperature in the step (1) is 120-150 ℃.
The stirring reaction time in the step (1) is 3 to 4 hours.
The invention also provides application of the cyanoethyl alkyl imidazole gallate ionic liquid as a biodiesel antioxidant.
The invention has the beneficial effects that:
the preparation method is simple, can be used for large-scale popularization and application, and the ionic liquid serving as a designer solution has great development significance and value.
The room-temperature ionic liquid prepared by the invention is used as an ionic liquid antioxidant special for biodiesel, and solves the problems of poor oil solubility and unsatisfactory antioxidant effect of the conventional antioxidant for biodiesel.
Drawings
FIG. 1 is a scheme showing the synthesis of 1- (2-cyanoethyl) -2-undecylimidazolium gallate ionic liquid;
FIG. 2 is a Fourier infrared spectrum of 1- (2-cyanoethyl) -2-undecylimidazolium gallate ionic liquid;
FIG. 3 is the NMR spectrum of 1- (2-cyanoethyl) -2-undecylimidazole gallate ionic liquid.
Detailed Description
The present invention will be described in further detail with reference to the accompanying drawings and specific embodiments.
Example 1
A preparation method of 1- (2-cyanoethyl) -2-undecyl imidazole gallate ionic liquid comprises the following specific steps:
(1) Placing 5.64g (0.03 mol) of gallic acid in a round bottom flask, adding 50mL of deionized water and 8.26g (0.03 mol) of 1- (2-cyanoethyl) -2-undecylimidazole, and heating in an oil bath at 120 ℃ for reaction for 3 hours while stirring;
(2) And (2) after the reaction in the step (1) is finished, washing with water for 3 times, and then removing water by rotary evaporation to obtain the product, namely the 1- (2-cyanoethyl) -2-undecyl imidazole gallate ionic liquid.
The synthetic route of the example is shown in figure 1, the final product obtained in the example is analyzed by Fourier infrared spectroscopy, as shown in figure 2, and the nuclear magnetic resonance hydrogen spectrum analysis is carried out to obtain figure 3, and the product is determined to be 1- (2-cyanoethyl) -2-undecyl imidazole gallate ionic liquid by analysis, and the yield is 64.8%.
Example 2
A preparation method of 1- (2-cyanoethyl) -2-undecyl imidazole gallate ionic liquid comprises the following specific steps:
(1) 9.40g (0.05 mol) of gallic acid was put in a round-bottom flask, and then 50mL of deionized water and 13.76g (0.05 mol) of 1- (2-cyanoethyl) -2-undecylimidazole were added and reacted with stirring in an oil bath at 125 ℃ for 4 hours;
(2) And (2) after the reaction in the step (1) is finished, washing with water for 3 times, and then removing water by rotary evaporation to obtain the product, namely the 1- (2-cyanoethyl) -2-undecyl imidazole gallate ionic liquid.
The synthetic route of this example was the same as example 1, yield 73.8%.
Example 3
A preparation method of 1- (2-cyanoethyl) -2-undecyl imidazole gallate ionic liquid comprises the following specific steps:
(1) 9.42g (0.05 mol) of gallic acid was put in a round bottom flask, and then 50mL of deionized water and 13.81g (0.05 mol) of 1- (2-cyanoethyl) -2-undecylimidazole were added and reacted with stirring in an oil bath at 150 ℃ for 3.5 hours;
(2) And (2) after the reaction in the step (1) is finished, washing the mixture for 3 times, and then removing water by rotary evaporation to obtain the product, namely the 1- (2-cyanoethyl) -2-undecyl imidazole gallate ionic liquid.
The synthetic route of this example was the same as example 1, with a yield of 68.5%.
Example 4
The 1- (2-cyanoethyl) -2-undecyl imidazole gallate ionic liquid prepared in the example 1 is subjected to an oxidation resistance test, the oxidation stability of biodiesel is determined by a Rancimat method, a European standard method EN 14112-2003 is adopted, the ionic liquid is used as a biodiesel antioxidant and is added into jatropha curcas biodiesel, the addition amount is 0.3 per mill, an equivalent amount of GA (0.3 per mill, a gallic acid conventional antioxidant) is added into a control group, a blank group is jatropha curcas biodiesel without ionic liquid, and a comparison result shows that the following table 1 shows that the oxidation stability of the jatropha curcas biodiesel with the addition of the 1- (2-cyanoethyl) -2-undecyl imidazole gallate ionic liquid is obviously improved, the induction period of the jatropha curcas is twice that without the addition of the ionic liquid, namely the oxidation stability is improved by 200%, the national standard of gallic acid is reached, the oxidation stability of the biodiesel with the addition of the equivalent amount of GA (GA) is also improved, and is 5.23 hours, but the national standard is not reached.
TABLE 1
Figure BDA0003272452840000031
The result proves that the synthesized ionic liquid has antioxidant performance and can improve the antioxidant performance of the jatropha curcas biodiesel.
Example 5
The oil solubility of the 1- (2-cyanoethyl) -2-undecylimidazole gallate ionic liquid prepared in example 1 is tested, and the results are shown in the following table 2. From table 2, it can be seen that the oil solubility of the prepared ionic liquid is superior to that of a common antioxidant, in the example of GA, about 100 times that of GA.
TABLE 2
Figure BDA0003272452840000032

Claims (5)

1. A cyanoethyl alkyl imidazole gallate ionic liquid is characterized by comprising cyanoethyl alkyl imidazole cations and gallic acid anions;
the cyanoethyl alkyl imidazole is 1- (2-cyanoethyl) -2-undecyl imidazole.
2. The method for preparing cyanoethyl alkyl imidazole gallate ionic liquid according to claim 1, wherein the product cyanoethyl alkyl imidazole gallate ionic liquid is obtained by mixing gallic acid, deionized water and equal molar amount of cyanoethyl alkyl imidazole, stirring the mixture under oil bath for reaction, washing the reaction product with water after the reaction is completed, and removing water by rotary evaporation.
3. The method for preparing cyanoethyl alkyl imidazole gallate ionic liquid according to claim 2, wherein the oil bath temperature is 120 to 150 ℃.
4. The method for preparing cyanoethyl alkyl imidazole gallate ionic liquid according to claim 2, wherein the reaction time is 3 to 4 hours under stirring.
5. Use of cyanoethyl alkyl imidazole gallate ionic liquid as claimed in claim 1 as a biodiesel antioxidant.
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