CN111841643A - Ferrocenyl Schiff base energetic cobalt complex combustion catalyst and preparation method and application thereof - Google Patents

Ferrocenyl Schiff base energetic cobalt complex combustion catalyst and preparation method and application thereof Download PDF

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CN111841643A
CN111841643A CN202010816253.1A CN202010816253A CN111841643A CN 111841643 A CN111841643 A CN 111841643A CN 202010816253 A CN202010816253 A CN 202010816253A CN 111841643 A CN111841643 A CN 111841643A
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ferrocenyl
schiff base
ligand
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赵军龙
陈丽琴
常帅
王欢
赵娅莉
黄世琪
苟小锋
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Northwestern University
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
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    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B23/00—Compositions characterised by non-explosive or non-thermic constituents
    • C06B23/007—Ballistic modifiers, burning rate catalysts, burning rate depressing agents, e.g. for gas generating
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B29/00—Compositions containing an inorganic oxygen-halogen salt, e.g. chlorate, perchlorate
    • C06B29/22—Compositions containing an inorganic oxygen-halogen salt, e.g. chlorate, perchlorate the salt being ammonium perchlorate
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06D—MEANS FOR GENERATING SMOKE OR MIST; GAS-ATTACK COMPOSITIONS; GENERATION OF GAS FOR BLASTING OR PROPULSION (CHEMICAL PART)
    • C06D5/00—Generation of pressure gas, e.g. for blasting cartridges, starting cartridges, rockets
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/842—Iron
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    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/845—Cobalt

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Abstract

The invention particularly relates to a ferrocenyl Schiff base energetic cobalt complex combustion catalyst and a preparation method and application thereof. The structural general formula (I) of the ferrocenyl Schiff base energetic cobalt complex combustion catalyst is as follows:
Figure DDA0002632827060000011
wherein n is 0 or 2; r is selected from
Figure DDA0002632827060000012
Any one of them. The invention synthesizes a novel ferrocenyl Schiff base with high catalytic efficiency and good safety1-5 of metal cobalt complex. Ferrocenyl Schiff base energetic compound synthesized by taking ferrocenyl formaldehyde and nitrogen-containing heterocycle as raw materials is taken as a ligand L, and metal cobalt (II) is taken as a central metal ion to synthesize the ferrocenyl ligand 1-5. The introduction of energy-containing unit and metal into ferrocene can exert transition metal oxide and Fe2O3The synergistic catalytic action of the ferrocene compound can also improve the combustion heat of the propellant so as to improve the catalytic activity of the ferrocene compound as a combustion rate catalyst.

Description

Ferrocenyl Schiff base energetic cobalt complex combustion catalyst and preparation method and application thereof
Technical Field
The invention particularly relates to a ferrocenyl Schiff base energetic cobalt complex combustion catalyst and a preparation method and application thereof.
Background
In Ammonium Perchlorate (AP) based solid propellants, ferrocene derivatives are typically added to increase the burn rate and decrease the pressure index of the propellant. Although the commercialized ferrocenyl Burning Rate Catalyst (BRC) shows high catalytic efficiency in the composite material, it has problems of easy migration and the like due to its low molecular weight and neutrality. The migration-prone nature allows such catalysts to migrate slowly to the surface of the solid propellant during use and to distribute unevenly. This drawback will enlarge the combustion area and increase the pressure in the rocket engine compartment, and eventually increase the explosion risk of the propellant, due to the rapid decomposition of the migrating combustion rate catalyst. Therefore, in order to extend the useful life of propellants and reduce military expenses, efforts have been made in the last few decades to design and synthesize combustion rate catalyst candidates with low migration tendency and high catalytic activity. Researchers have taken effective methods to solve the problems of neutral burn rate catalysts, such as increasing the molecular weight or molecular polarity of small neutral ferrocene derivatives, grafting ferrocenyl onto polymer or dendrimer chains, introducing ionic liquids and coordination compounds to form ferrocene derivatives. Although hundreds of novel ferrocene derivatives have been reported to solve the high mobility problem and enhance the catalytic activity of neutral ferrocenyl combustion rate catalysts, the existing problems have not been solved well.
Disclosure of Invention
The invention aims to provide a ferrocenyl Schiff base energetic cobalt complex combustion catalyst and a preparation method and application thereof. The invention relates to a ferrocenyl complex formed by taking a ferrocenyl Schiff base energetic compound as a ligand and metallic cobalt (Co (II)), which improves the combustion rate catalytic activity based on an AP propellant.
The realization process of the invention is as follows:
a compound of the general structural formula (I):
Figure BDA0002632827040000011
wherein n is 0 or 2;
r is selected from
Figure BDA0002632827040000021
Any one of them.
The preparation method of the compound comprises the steps of taking the ferrocenyl Schiff base energetic compound as a ligand, taking anhydrous methanol as a solvent, adding triethylamine, raising the temperature of the system, dropwise adding anhydrous ethanol solution containing cobalt nitrate into a warm system for reaction, generating a precipitate through the reaction, washing and drying to obtain a target product.
In the preparation method of the compound, the general formula (L) of the ferrocenyl Schiff base energetic compound is
Figure BDA0002632827040000022
Wherein R is selected from
Figure BDA0002632827040000023
Figure BDA0002632827040000024
Any one of them.
Further, the molar ratio of the ferrocenyl Schiff base energetic compound to the cobalt nitrate is 2: 1.
the compound is used as a rocket combustion catalyst.
The invention has the following positive effects:
the invention synthesizes a novel ferrocenyl Schiff base energetic metal cobalt complex 1-5 with high catalytic efficiency and good safety. Ferrocenyl Schiff base energetic compound synthesized by taking ferrocenyl formaldehyde and nitrogen-containing heterocycle as raw materials is taken as a ligand L, and metal cobalt (II) is taken as a central metal ion to synthesize the ferrocenyl ligand 1-5. The introduction of energy-containing unit and metal into ferrocene can exert transition metal oxide and Fe2O3The synergistic catalytic action of the ferrocene compound can also improve the combustion heat of the propellant so as to improve the catalytic activity of the ferrocene compound as a combustion rate catalyst.
Drawings
FIG. 1 is a crystal structure of ligand L1;
FIG. 2 is a crystal structure diagram of ligand L2;
FIG. 3 is a crystal structure of ligand L3;
FIG. 4 is an infrared spectrum of complex 1;
FIG. 5 is an infrared spectrum of complex 2;
FIG. 6 is an infrared spectrum of complex 3;
FIG. 7 is an infrared spectrum of complex 4;
FIG. 8 is an infrared spectrum of complex 5;
FIG. 9 shows the decomposition performance of ferrocenyl Schiff base energetic cobalt complex 1-5 in catalyzing ammonium perchlorate, wherein AP is ammonium perchlorate, AP +1 is complex 1 in catalyzing ammonium perchlorate, AP +2 is complex 2 in catalyzing ammonium perchlorate, AP +3 is complex 3 in catalyzing ammonium perchlorate, AP +4 is complex 4 in catalyzing ammonium perchlorate, and AP +5 is complex 5 in catalyzing ammonium perchlorate.
Detailed Description
The present invention will be further described with reference to the following examples.
EXAMPLE 1 Synthesis of ligand L1
Adding 3-amino-1, 2, 4-triazole (10mmol) into 50mL of toluene, dropping 3 drops of triethylamine, heating to 55 ℃, adding ferrocenecarboxaldehyde (10mmol) into a warm system, continuing to react at the temperature, monitoring the reaction process by TLC, separating out a large amount of bright red solid in a system for about 72 hours, carrying out suction filtration while hot and washing to obtain deep red powdery solid. Recrystallizing with petroleum ether to obtain red solid. The resulting red solid was dissolved in a small amount in 10mL of dichloromethane, and a mixed solvent was prepared by adding an appropriate amount of petroleum ether (dichloromethane: petroleum ether ═ 1:1), and a single crystal was cultured and subjected to single crystal diffraction test. FIG. 1 is a crystal structure diagram of ligand L1.
Figure BDA0002632827040000031
Example 2 Synthesis of ligand L2
Adding 4-amino-1, 2, 4-triazole (10mmol) into 50mL of methanol, dripping 4 drops of triethylamine, heating to 50 ℃, adding ferrocenecarboxaldehyde (10mmol) into a warm system, continuing to react at the temperature, monitoring the reaction process by TLC (thin layer chromatography), separating out a large amount of bright red solid in a system for about 72 hours, carrying out suction filtration while hot and washing to obtain deep red powdery solid. Recrystallizing with petroleum ether to obtain red solid. The resulting red solid was dissolved in a small amount in 10mL of methanol, and an appropriate amount of water was added to prepare a mixed solvent (methanol: water ═ 1:1), and a single crystal was cultured and subjected to single crystal diffraction test. FIG. 2 is a crystal structure diagram of ligand L2.
Figure BDA0002632827040000041
Example 3 Synthesis of ligand L3
Adding 3, 5-diamino-1, 2, 4-triazole (10mmol) into 50mL of toluene, dropping 3 drops of triethylamine, heating to 50 ℃, adding ferrocenecarboxaldehyde (10mmol) into a warm system, continuing to react at the temperature, monitoring the reaction process by TLC, precipitating a large amount of bright red solid in the system for about 72 hours, carrying out suction filtration while hot and washing to obtain deep red powdery solid. Recrystallizing with petroleum ether to obtain red solid. The resulting red solid was dissolved in a small amount in 10mL of dichloromethane, and a mixed solvent was prepared by adding an appropriate amount of petroleum ether (dichloromethane: petroleum ether ═ 1:1), and a single crystal was cultured and subjected to single crystal diffraction test. FIG. 3 is a crystal structure diagram of ligand L3.
Figure BDA0002632827040000042
Example 4 Synthesis of ligand L4
L4 was synthesized from 5-aminotetrazole as the starting material according to the method of example 1.1H NMR(400MHz,DMSO-d6)ppm:4.17(s,5H,C5H5),4.45(t,2H,C5H4),4.70(t,2H,C5H4),9.41(s,1H,N＝C-H),10.40(s,1H,NH)；13C NMR(100MHz,DMSO-d6)ppm:158.1,151.4,73.4,73.1,71.8,70.9；HRMS(ESI)m/zC12H11FeN5[M+H+]282.0397; found 282.0399.
Figure BDA0002632827040000051
Example 5 Synthesis of ligand L5
L5 was synthesized from 2-methyl-5-aminotetrazole as the starting material according to the method of example 1.1H NMR(400MHz,DMSO-d6)ppm:2.40(s,3H,CH3),4.13(s,5H,C5H5),4.43(t,2H,C5H4),4.50(t,2H,C5H4),9.41(s,1H,N＝C-H)；13C NMR(100MHz,DMSO-d6)ppm:161.0,148.6,75.1,73.7,73.1,70.6,32.8；HRMS(ESI)m/z C13H13FeN5[M+H+]296.0602; found 296.0593.
Figure BDA0002632827040000052
EXAMPLE 6 Synthesis of Complex 1 Combustion catalyst
Dissolving 3- (ferrocenylmethyl) imino-1, 2, 4-triazole (10mmol) (ligand L1) in 50mL of anhydrous methanol, and dripping 1-3 drops of triethylAnd (3) raising the temperature of amine to 60 ℃, slowly dripping 10mL of anhydrous ethanol solution containing cobalt nitrate (5mmol) into a warm system, observing the generation of bright red precipitates after dripping, continuously reacting for about 5 hours, observing the generation of a large amount of precipitates, and stopping the reaction. And centrifuging the reaction solution, repeatedly washing with anhydrous methanol and centrifuging until the supernatant is colorless liquid, collecting the solid, drying in the air and storing in a sealed manner. FIG. 4 is an infrared spectrum of complex 1. IR (KBr) 3000-3500cm-1The broad peaks are due to the overlap of N-H, Fc-H and C-H, 1491, 1190, 1104, 825cm-1Nearby is absorption peak of ferrocene skeleton, 1610cm-1And the adjacent part is a C ═ N double bond stretching vibration absorption peak.
Figure BDA0002632827040000061
EXAMPLE 7 Synthesis of Complex 2 Combustion catalyst
The complex 2 was synthesized by the method of example 6 using 4- (ferrocenylmethyl) imino-1, 2, 4-triazole (ligand L2) as the ligand, and fig. 5 is an infrared spectrum of the complex 2.
Figure BDA0002632827040000062
EXAMPLE 8 Synthesis of Complex 3 Combustion catalyst
3- (ferrocenylmethyl) imino-5-amino-1, 2, 4-triazole (ligand L3) is used as a ligand, the complex 3 is synthesized by the method of example 6, and FIG. 6 is an infrared spectrogram of the complex 3.
Figure BDA0002632827040000063
EXAMPLE 9 Synthesis of Complex 4 Combustion catalyst
The complex 4 is synthesized by the method of example 6 with 5- (ferrocenylmethyl) iminotetrazole (ligand L4) as a ligand, and fig. 7 is an infrared spectrum of the complex 4. HRMS (ESI) m/z C24H20Fe2N10Co[M+Na+]641.9795; found 641.9774.
Figure BDA0002632827040000071
EXAMPLE 10 Synthesis of Complex 5 Combustion catalyst
With 2-methyl-5- (ferrocenylmethyl) iminotetrazole (ligand L5) as a ligand, complex 5 was synthesized according to the method of example 6, and fig. 8 is an infrared spectrum of complex 5.
Figure BDA0002632827040000072
EXAMPLE 11 testing of catalytic Performance of Complex 1-5 Combustion catalyst
The decomposition performance of ferrocenyl metal cobalt Schiff base energetic cobalt complex 1-5 in catalyzing perchloric acid amine is tested by using a differential scanning calorimeter. Mixing the ferrocenyl metal cobalt Schiff base energetic cobalt complex 1-5 and AP according to the mass ratio of 1:3, setting the heating rate at 10 ℃/min and the total sample dosage at about 0.7mg, and heating to 800 ℃ at room temperature and in a nitrogen atmosphere for testing. The test result shows that the ferrocenyl metal cobalt Schiff base energetic cobalt complex 1-5 can greatly advance the peak temperature of two-step exothermic peaks of AP and concentrate the exothermic reaction, and the figure is 9. Wherein, the complex 1 advances the low-temperature exothermic peak temperature and the high-temperature exothermic peak temperature of pure AP by 45 ℃ and 150 ℃ respectively, and the exothermic quantity is 1576J/g; the complex 2 advances the low-temperature exothermic peak temperature and the high-temperature exothermic peak temperature of pure AP by 54 ℃ and 138 ℃ respectively, and the exothermic quantity is 1870J/g; the complex 3 advances the low-temperature exothermic peak temperature and the high-temperature exothermic peak temperature of pure AP by 33 ℃ and 138 ℃ respectively, and the exothermic quantity is 1635J/g; the complex 4 advances the low-temperature exothermic peak temperature and the high-temperature exothermic peak temperature of pure AP by 43 ℃ and 148 ℃ respectively, and the exothermic quantity is 1546J/g; the complex 5 advances the low-temperature exothermic peak temperature and the high-temperature exothermic peak temperature of pure AP by 86 ℃ and 191 ℃ respectively, and the exothermic quantity is 1353J/g.
The foregoing is a more detailed description of the invention in connection with specific preferred embodiments and is not intended to limit the invention to the particular forms disclosed. For those skilled in the art to which the invention pertains, several simple deductions or substitutions can be made without departing from the spirit of the invention, and all shall be considered as belonging to the protection scope of the invention.

Claims (5)

1. A compound of the general structural formula (I):
Figure FDA0002632827030000011
wherein n is 0 or 2;
r is selected from
Figure FDA0002632827030000012
Any one of them.
2. A process for the preparation of a compound according to claim 1, characterized in that: taking a ferrocenyl Schiff base energetic compound as a ligand, taking absolute methanol as a solvent, adding triethylamine, raising the temperature of the system, dropwise adding absolute ethanol solution containing cobalt nitrate into a warm system for reaction to generate a precipitate, washing and drying to obtain a target product.
3. A process for the preparation of a compound according to claim 2, characterized in that: the general formula (L) of the ferrocenyl Schiff base energetic compound is
Figure FDA0002632827030000013
Wherein R is selected from
Figure FDA0002632827030000014
Figure FDA0002632827030000015
Any one of them.
4. A process for the preparation of a compound according to claim 2, characterized in that: the molar ratio of the ferrocenyl Schiff base energetic compound to the cobalt nitrate is 2: 1.
5. use of a compound according to claim 1 as a rocket combustion catalyst.
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CN110330394A (en) * 2019-08-07 2019-10-15 西安近代化学研究所 A kind of graphene-schiff bases lead compound and preparation method thereof
CN116041720A (en) * 2023-01-04 2023-05-02 浙江大学 Anti-migration ferrocenyl dendritic polymer burning rate catalyst, and preparation method and application thereof

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CN116041720A (en) * 2023-01-04 2023-05-02 浙江大学 Anti-migration ferrocenyl dendritic polymer burning rate catalyst, and preparation method and application thereof
CN116041720B (en) * 2023-01-04 2024-02-27 浙江大学 Anti-migration ferrocenyl dendritic polymer burning rate catalyst, and preparation method and application thereof

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