CN112521338A - Spontaneous combustion ionic liquid containing tension ring structure and application - Google Patents
Spontaneous combustion ionic liquid containing tension ring structure and application Download PDFInfo
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
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Abstract
The invention provides a spontaneous combustion ionic liquid containing a tension ring structure and application thereof, and the preparation steps are as follows: (1) imidazole and sodium hydroxide are added into a reaction bottle, and drying is carried out after the reaction is finished; (2) mixing the dried product of the step (1) with a halide R1Adding the X into a reaction bottle in proportion for reaction, filtering after the reaction is finished to obtain filtrate, washing and extracting to obtain an organic phase, and evaporating dichloromethane to obtain an imidazole precursor; (3) the imidazole precursor obtained in the step (2) and a halide R2Adding the X into a reaction bottle in proportion, reacting to obtain a precipitate, washing to evaporate a solvent, and drying to obtain an ionic liquid; (4) and (3) adding the ionic liquid in the step (3) and the sodium salt or silver salt D of the corresponding anion into a reaction bottle, adding a solvent C, filtering after reaction, evaporating the solvent, and drying to obtain the ionic liquid. The autoignition ionic liquid obtained by the invention has very high enthalpy of formation (basically more than 200KJ mol)‑1) Is very highThe energy value of (c).
Description
Technical Field
The invention relates to the field of natural ionic liquid, in particular to spontaneous combustion ionic liquid containing a tension ring structure and application thereof.
Background
Along with the development of aerospace technology, liquid rocket propellant is increasingly considered as a power source of rocket engines. The existing liquid propellant mainly comprises high-energy fuels such as hydrazine, kerosene, liquid hydrogen and the like and oxidants such as dinitrogen tetroxide, liquid oxygen and the like. However, the existing propellants mainly have the following problems: (1) the non-hydrazine material has lower density than that of the impact and harsh combustion conditions. (2) Hydrazine materials are volatile, highly toxic, strongly carcinogenic, and cause serious harm to humans and the environment.
Ionic liquids, also known as room temperature ionic liquids, refer to a class of substances that are composed of two parts, cationic and anionic, and that are in a liquid state at relatively low temperatures (typically below 100 ℃). The composite material has good solubility, electrical property, ion conductivity, no vapor pressure, wide liquid phase stability range and designability, so that the composite material is widely applied to the fields of electrochemistry, solvents, catalysts and the like. Pyrophoric Ionic Liquids (HILs) refer to Ionic Liquids and oxidants (e.g., concentrated HNO)3Concentrated H2O2Concentrated N2O4) The contact can react violently to generate spontaneous combustion. Since it enters the engine as a liquid and no additional ignition device is required, the design of the engine can be simplified and is safer. Meanwhile, the spontaneous combustion ionic liquid has low volatility, so that the liquid is more green and healthy compared with the traditional liquid fuel hydrazine with high risk. In 2008, Schneider et al reported dicyandiamide anion (-N (CN)2) ILs composed of imidazole cations generate spontaneous combustion after contacting with an oxidant White Fuming Nitric Acid (WFNA). Due to the designability of the spontaneous combustion ionic liquid, the ions and anions are functionally modified, so that partial physicochemical properties of the ionic liquid are adjusted to haveHas the advantages of low vapor pressure, low toxicity, spontaneous combustibility and the like, and overcomes the defects of the traditional hydrazine propellant in these aspects. In the next decade, more and more researchers are focusing on the research of pyrophoric ionic liquids.
The existing spontaneous combustion ionic liquid containing cations with imidazole structures is generally designed by introducing straight-chain alkane, straight-chain alkene or straight-chain alkyne on imidazole and matching with anion to form ionic liquid with spontaneous combustion property, but the ionic liquid has the problem of low energy.
Disclosure of Invention
The invention provides a spontaneous combustion ionic liquid containing a tension ring structure and application thereof, and a scheme of introducing the tension ring structure into the ionic liquid is adopted, so that the HILs energy is improved.
The invention modifies imidazole, adds a three-membered ring or four-membered ring structure to obtain imidazole cation with a tension ring structure, and then matches with anion to finally obtain the spontaneous combustion ionic liquid. Computing and simulating by Gaussian software to obtain HILs formation enthalpy data, computing by Explo5 to obtain specific impulse data of the HILs, and measuring parameters such as phase transition temperature, density viscosity, ignition delay time and the like of the obtained HILs by using a differential scanner, a density viscometer and a high-speed camera.
The technical scheme for realizing the invention is as follows:
the spontaneous combustion ionic liquid containing the tension ring structure is prepared by the following steps:
(1) imidazole and sodium hydroxide are added into a reaction bottle, are stirred vigorously for reaction, and are dried after the reaction is finished;
(2) mixing the dried product of the step (1) with a halide R1Adding the X into a reaction bottle in proportion, adding the solvent A at the same time, stirring vigorously for reaction, filtering after the reaction is finished to obtain a filtrate, washing and extracting to obtain an organic phase, and evaporating dichloromethane to obtain an imidazole precursor;
(3) the imidazole precursor obtained in the step (2) and a halide R2Adding the X into a reaction bottle in proportion, adding a solvent B at the same time, reacting to obtain a precipitate, washing to evaporate the solvent, and drying to obtain an ionic liquid;
(4) and (3) adding the ionic liquid in the step (3) and the sodium salt or silver salt D of the corresponding anion into a reaction bottle, adding a solvent C, filtering after reaction, evaporating the solvent, and drying to obtain the ionic liquid.
The molar ratio of imidazole to sodium hydroxide in the step (1) is 1: (1-2), the reaction temperature is 90-120 ℃, and the reaction time is 2-5 h.
The halide R in the step (2)1In X, R1Is composed of
、
Wherein n =0, 1, 2, 3 or 4, and X is Br-Or I-(ii) a Drying the product with a halide R1The molar ratio of X is 1: (0.7-1.5), the reaction temperature is 40-80 ℃, and the reaction time is 10-40 h.
The step (3) R2In X, R2Comprises the following steps:
、
、CH3、C2H5、C3H7、C4H9、C5H11、C6H13、C7H15、C8H17、C9H19、C10H21、CH=CH2、CH=C2H4wherein n =0, 1, 2, 3 or 4, and X is Br-Or I-(ii) a The reaction temperature is 25-70 ℃, and the molar ratio of the imidazole precursor to the halide is 1: (0.7-1.5) for 10-40 h.
The anion in the step (4) is any one of the following structures:
。
the molar ratio of the ionic liquid to the sodium salt or silver salt D of the corresponding anion is 1: (1-2) the reaction time is 1-40 h.
The solvent A is tetrahydrofuran or acetonitrile, the solvent B is ethyl acetate or diethyl ether, and the solvent C is methanol or tetrahydrofuran.
The density of the ionic liquid is more than or equal to 1.00gcm-1The melting point is lower than-60 ℃.
The ionic liquid is applied to the field of rocket propellants.
The reaction equation is as follows:
the invention has the beneficial effects that: the autoignition ionic liquid obtained by the invention has very high enthalpy of formation (basically more than 200KJ mol)-1) And has high energy. Meanwhile, when the ratio of the oxidant to the spontaneous combustion ionic liquid is close to 3:1, the maximum value of the specific impulse is obtained, and the specific impulse value is higher than that of most of the existing spontaneous combustion ionic liquid. And the density of most of the ionic liquid is more than or equal to 1.00gcm-1Larger than most of the autoignition ionic liquids at present. It is generally low in viscosity, liquid at room temperature with a wide liquid range, and mostly has a melting point below-60 ℃.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a schematic diagram of the ignition in embodiment 1 of the present invention.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without inventive effort based on the embodiments of the present invention, are within the scope of the present invention.
Example 1
The ionic liquid is prepared by the following steps:
1-methylcyclopropyl-3-methylimidazolium dicyanoammonium salt:
in the first step, imidazole (6.808 g, 0.100 mol) and sodium hydroxide (8.000 g, 0.200 mol) were added to a 500ml round bottom flask, and reacted with vigorous stirring at 90 ℃ for 5 hours, followed by drying using a vacuum oven.
In the second step, methylcyclopropyl bromide (9.450 g, 0.070 mol) was added to the dried product, and 200ml of THF was added, and the reaction was vigorously stirred at 40 ℃ for 40 hours. After the reaction was completed, filtration was performed, and the solid was washed with 10% by volume of THF, the filtrates were combined, and finally the solvent was distilled off, 100ml of deionized water and 100ml of dichloromethane were added for extraction to obtain an organic phase, and dichloromethane was distilled off to obtain methylcyclopropylimidazole.
Thirdly, adding methylcyclopropylimidazole (12.200 g, 0.100 mol) and methyl iodide (9.9330 g, 0.070 mol) into a 100ml round-bottom flask, adding 50ml ethyl acetate, reacting at 25 ℃ for 10 hours to generate phase separation, decanting the supernatant, washing with 10ml ethyl acetate, distilling off the ethyl acetate, and drying to obtain the 1-methylcyclopropyl-3-methylimidazolium iodide.
And fourthly, adding 1-methylcyclopropyl-3-methylimidazolium iodide (26.400 g, 0.100 mol) and dicyanoammonium salt (34.772 g, 0.200 mol) into a 100ml round-bottom flask, adding 50ml of solvent methanol, reacting for 10 hours, filtering after the reaction to obtain filtrate, evaporating the solvent, and drying to obtain the final high-purity target ionic liquid. (20.106 g of a pale yellow liquid was obtained, yield 99%).
Example 2
The ionic liquid is prepared by the following steps:
1-methylcyclobutyl-3-propylimidazolium dicyanamide salt:
in the first step, imidazole (6.808 g, 0.100 mol) and sodium hydroxide (4.800 g, 0.120 mol) were added to a 500ml round bottom flask, and reacted with vigorous stirring at 110 ℃ for 3 hours, followed by drying.
In the second step, methyl cyclobutylbromide (16.390 g, 0.110 mol) was added to the dried product, and 100ml of THF was added, and the reaction was vigorously stirred at 50 ℃ for 20 hours. After the reaction was completed, filtration was performed, and the solid was washed with 10% by volume of THF, and finally the solvent was distilled off, 50ml of deionized water and 50ml of dichloromethane were added for extraction to obtain an organic phase, and dichloromethane was distilled off to obtain methylcyclopropylimidazole.
And the third step, adding methylcyclobutylimidazole (13.600 g, 0.100 mol) and iodopropane (18.699 g, 0.110 mol) into a 100ml round-bottom flask, adding 50ml ethyl acetate, reacting at 35 ℃ for 20 hours to generate phase separation, washing with 10ml ethyl acetate, distilling off ethyl acetate, and drying to obtain 1-methylcyclobutyl-3-propylimidazole iodonium salt.
And fourthly, adding 1-methylcyclobutyl-3-propylimidazole iodonium salt (30.600 g, 0.100 mol) and dicyanoammonium salt (17.386 g, 0.100 mol) into a 100ml round-bottom flask, adding 50ml of solvent methanol, reacting for 40 hours, filtering after the reaction to obtain filtrate, evaporating the solvent, and drying to obtain the final high-purity target ionic liquid. (24.018 g of a pale yellow liquid was obtained, yield 98%).
Example 3
The ionic liquid is prepared by the following steps:
1-cyclobutyl-3-pentylimidazolium dicyanoammonium salt:
in the first step, imidazole (6.808 g, 0.100 mol) and sodium hydroxide (4.000 g, 0.100 mol) were added to a 500ml round bottom flask, reacted with vigorous stirring at 120 ℃ for 2 hours, and then dried.
In the second step, cyclobutylbromide (20.250 g, 0.150 mol) was added to the dried product, and 80ml of acetonitrile was added, and the reaction was vigorously stirred at 80 ℃ for 10 hours. After the reaction was completed, filtration was performed, and the solid was washed with acetonitrile of 10% of the original volume, and finally the solvent was distilled off, 50ml of deionized water and 50ml of dichloromethane were added for extraction to obtain an organic phase, and dichloromethane was distilled off to obtain methylcyclopropylimidazole.
The third step is to take cyclobutyl imidazole (12.200 g, 0.100 mol) and iodopentane (29.708 g, 0.150 mol) and add them into 100ml round bottom flask, add appropriate 50ml ethyl acetate, react at 70 ℃ for 40 hours to produce phase separation, wash with 10ml ethyl acetate, evaporate ethyl acetate and dry to obtain 1-methylcyclopropyl-3-methylimidazolium iodide.
And fourthly, adding 1-cyclobutyl-3-pentylimidazole iodonium salt (32.000 g, 0.100 mol) and dicyanoammonium salt (18.255 g, 0.105 mol) into a 200ml round-bottom flask, adding 70ml of solvent methanol, reacting for 20 hours, filtering after the reaction to obtain filtrate, evaporating the solvent, and drying to obtain the final target ionic liquid. (obtained was 24.864g of a pale yellow liquid, 96% yield).
The enthalpy of formation of part of the ionic liquid and the proportion of the oxidant to the HILs are listed as follows: time 1 beat data
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (9)
1. The spontaneous combustion ionic liquid containing the tension ring structure is characterized by comprising the following preparation steps:
(1) imidazole and sodium hydroxide are added into a reaction bottle, are stirred vigorously for reaction, and are dried after the reaction is finished;
(2) mixing the dried product of the step (1) with a halide R1Adding the X into a reaction bottle in proportion, adding the solvent A at the same time, stirring vigorously for reaction, filtering after the reaction is finished to obtain a filtrate, washing and extracting to obtain an organic phase, and evaporating dichloromethane to obtain an imidazole precursor;
(3) the imidazole precursor obtained in the step (2) and a halide R2Adding X into a reaction bottle in proportion, adding solvent B, reacting to obtain precipitate, washing to remove solventDrying to obtain ionic liquid;
(4) and (3) adding the ionic liquid in the step (3) and the sodium salt or silver salt D of the corresponding anion into a reaction bottle, adding a solvent C, filtering after reaction, evaporating the solvent, and drying to obtain the ionic liquid.
2. The pyrophoric ionic liquid of claim 1, comprising a tension ring structure, wherein: the molar ratio of imidazole to sodium hydroxide in the step (1) is 1: (1-2), the reaction temperature is 90-120 ℃, and the reaction time is 2-5 h.
3. The pyrophoric ionic liquid of claim 1, comprising a tension ring structure, wherein: the halide R in the step (2)1In X, R1Is composed of
、
Wherein n =0, 1, 2, 3 or 4, and X is Br-Or I-(ii) a Drying the product with a halide R1The molar ratio of X is 1: (0.7-1.5), the reaction temperature is 40-80 ℃, and the reaction time is 10-40 h.
4. The pyrophoric ionic liquid of claim 1, comprising a tension ring structure, wherein: the step (3) R2In X, R2Comprises the following steps:
、
、CH3、C2H5、C3H7、C4H9、C5H11、C6H13、C7H15、C8H17、C9H19、C10H21、CH=CH2、CH=C2H4wherein n =0, 1, 2, 3 or 4, and X is Br-Or I-(ii) a The reaction temperature is 25-70 ℃, and the molar ratio of the imidazole precursor to the halide is 1: (0.7-1.5) for 10-40 h.
5. The pyrophoric ionic liquid of claim 1, wherein the anion of step (4) is any one of the following structures:
。
6. the pyrophoric ionic liquid of claim 1, comprising a tension ring structure, wherein: the molar ratio of the ionic liquid to the sodium salt or silver salt D of the corresponding anion is 1: (1-2) the reaction time is 1-40 h.
7. The pyrophoric ionic liquid of claim 1, comprising a tension ring structure, wherein: the solvent A is tetrahydrofuran or acetonitrile, the solvent B is ethyl acetate or diethyl ether, and the solvent C is methanol or tetrahydrofuran.
8. The pyrophoric ionic liquid of any of claims 1-7, comprising a strained ring structure, wherein: the density of the ionic liquid is more than or equal to 1.00gcm-1The melting point is lower than-60 ℃.
9. Use of an ionic liquid according to claim 8 in the field of rocket propellants.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115850279A (en) * | 2022-12-05 | 2023-03-28 | 哈尔滨工业大学（深圳） | Theophylline derived autoignition ionic salt and preparation method thereof |
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| US8758531B1 (en) * | 2011-03-15 | 2014-06-24 | The United States Of America As Represented By The Secretary Of The Air Force | Catalytic hypergolic bipropellants |
| CN103012275A (en) * | 2013-01-04 | 2013-04-03 | 江南大学 | Method for producing high-purity N-alkyl imidazole |
| CN107216275A (en) * | 2017-06-27 | 2017-09-29 | 中国科学院过程工程研究所 | Fourth pyridine class ionic liquid and its preparation method and application |
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| CN115850279A (en) * | 2022-12-05 | 2023-03-28 | 哈尔滨工业大学（深圳） | Theophylline derived autoignition ionic salt and preparation method thereof |
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