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The chemical formula of acetyl ferrocene powder is C12H12FeO, CAS 1271-55-2, with a molecular weight of approximately 228.07 g/mol (specific values may vary slightly depending on different data, such as 228.068 g/mol). Its CAS registration number is 1271-55-2, and its EINECS number is 215-043-2. Having some aromaticity similar to benzene, it is more prone to electrophilic substitution reactions than benzene, such as the Fride l-Crafts reaction. However, its sensitivity to oxidation limits its application in synthesis. The reaction of ferrocene usually requires isolation from air and is directly prepared by chemical reaction between acetic anhydride and ferrocene. At room temperature and pressure, it exists in solid form and appears as bright orange needle shaped or crystalline powder. This vivid color not only makes it easy to identify, but also reflects the unique electronic structure and chemical bonding within its molecules. The solubility in water is extremely low, almost insoluble in water. However, it can be slightly soluble in certain organic solvents, such as alcohols. This difference in solubility is of great significance for its application in different fields. For example, when preparing solutions for specific purposes, suitable solvents can be selected to improve their solubility and stability. As an important organic metal compound, it is used as a shock absorber for gasoline, an absorber for ultraviolet radiation, and an additive for rocket fuel.
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CF |
C12H12FeO |
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EM |
228 |
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MW |
228 |
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m/z |
228 (100.0%), 229 (13.0%), 226 (6.4%), 229 (2.3%) |
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EA |
C, 63.20; H, 5.30; Fe, 24.49; O, 7.01 |
Melting point 81-83 ° C (lit.), Boiling point 160-163 ° C (3.0004 mmHg), Density >1 g/cm3 (20 ℃), Flash point 160-163 ° c/4mm, Sealed in dry, room temperature, Form need like crystal powder, Color orange, Water solubility, Stable Incompatible with strong oxidizing agents, reducing agents, strong acids, strong bases. Hazard symbol (GHS), GHS06, Warning word danger, Hazard description h310-h300, Precautions p264-p301+p310-p262-p280h-p301+p310a-p321-p405-p501a, Dangerous goods sign t+, Hazard category code 28, Safety instructions 28-36/37-45-28a-1, Dangerous goods transport No. UN 2811 6.1/pg 2, WGK Germany 3, RTECS No. ob3700000, F 10, TSCA Yes, HazardClass 6.1, PackingGroup II
Acetyl ferrocene powder, as an important metal organic compound, plays a crucial role in rocket fuel.
Mechanism of action:
As an accelerator for solid rocket fuel, it mainly promotes the combustion reaction of the fuel through its unique chemical properties. In rocket engines, solid fuel is mixed with oxidizer and ignited through an ignition device to initiate combustion. It can reduce the activation energy of fuel combustion, making the combustion reaction easier to carry out, thereby improving the combustion rate and efficiency. In addition, it can improve the combustion stability of fuel and reduce fluctuations and instability during the combustion process.
Application example:
In solid rocket engines, it is often added to fuel formulations to optimize combustion performance. By precisely controlling its addition amount, precise adjustment of combustion rate can be achieved to meet different requirements during rocket flight. For example, in the initial stage of rocket launch, higher thrust is required to overcome the Earth's gravity, and the amount of this substance added can be increased to improve the combustion rate; After stable flight, the amount of additives can be appropriately reduced to maintain a stable combustion state.
Promote complete combustion:
It can promote the full reaction between combustible components such as hydrocarbons in rocket fuel and oxidants, reducing the generation of incomplete combustion products. This can not only improve the utilization rate of fuel and the thrust performance of rockets, but also reduce the emission of harmful substances generated during combustion and lower environmental pollution.
Increase calorific value:
By accelerating combustion reactions and improving combustion efficiency, it helps to enhance the overall calorific value of rocket fuel.
Acetyl ferrocene powder is the amount of energy released during fuel combustion, and for rockets, higher calorific value means stronger thrust and longer range.
Enhance stability:
Rocket fuel needs to maintain a certain degree of stability during combustion to avoid dangerous situations such as explosions. It can improve the combustion stability of fuel, reduce fluctuations and instability during the combustion process, thereby enhancing the safety and reliability of rocket engines.
Improve liquidity:
In solid rocket fuel, it can be used as an additive to improve the flowability of the fuel. Good fluidity helps fuel to be evenly distributed and rapidly burned in the combustion chamber, thereby improving combustion efficiency and thrust performance.
Increase density:
By increasing the density of fuel, the mass of fuel per unit volume can be improved, thereby increasing the thrust of the rocket. As a high-density compound, it can to some extent increase the density and energy density of fuel.
Reduce coking and carbon deposition:
In high-temperature and high-pressure combustion environments, fuel is prone to coking and carbon deposition, which can affect combustion efficiency and engine performance. It can suppress the formation of coking and carbon deposits, maintain the cleanliness and smoothness of the combustion chamber, and thus extend the service life of the engine.
Iron, as a key additive in rocket fuel, has a positive impact on the thrust performance, stability, and safety of rockets through various means such as promoting combustion reactions, improving combustion performance, and enhancing fuel quality. With the continuous development of aerospace technology, the requirements for the performance of rocket fuels are also increasing, and the research and application of high-performance additives will be increasingly valued. In the future, with the continuous emergence of new materials and technologies, the application prospects of acetyl ferrocene in the field of rocket fuel will be even broader.
Synthesis of acetyl ferrocene powder : Add 1g of ferrocene and 10ml of acetic anhydride into a 50ml round bottom flask, and slowly add 2ml of 85% phosphoric acid using a dropper under oscillation. After adding the ingredients, plug the bottle mouth with a drying tube containing anhydrous calcium chloride, heat in a boiling water bath for 10 minutes, and add the ingredients intermittently and shake. Pour the reactants into a 400ml beaker containing 40g of crushed ice, rinse the flask with 10ml of cold water, and add the rinsing solution to the beaker. Add solid sodium bicarbonate in batches while stirring until the solution is neutral (to avoid solution overflow and excess sodium bicarbonate). Cool the neutralized reactants in an ice bath for 15 minutes, filter and collect the separated orange solid, wash twice with 40ml of ice water each time, dry and air dry.
The specific steps are as follows:
Material preparation: Accurately weigh 1g of ferrocene (C10H10Fe, MW ≈ 186.04 g/mol) and measure 10ml of acetic anhydride (CH3COOCOCH3, MW ≈ 102.09 g/ml). Meanwhile, prepare 2ml of 85% phosphoric acid (H3PO4) solution for catalytic reaction.
Attention: All operations should be carried out in a fume hood and appropriate personal protective equipment (such as safety goggles, laboratory coats, gloves, etc.) should be worn.
Mixed reactants: Add ferrocene and acetic anhydride into a dry 50ml round bottom flask, gently stir with a magnetic stirrer to mix evenly. This step is mainly a physical mixing process and does not involve chemical equations.
Add catalyst: Slowly add 2ml of 85% phosphoric acid solution with continuous stirring using a dropper. Phosphoric acid, as a catalyst, can promote the addition reaction of acetyl groups to ferrocene. There is no direct chemical equation for this step, but the addition of the catalyst changes the energy barrier of the reaction pathway.
Heating reaction: Place the round bottom flask in a boiling water bath and heat it at a temperature close to 100 ° C. Heating promotes the movement and collision frequency of reactant molecules, thereby accelerating the acetylation reaction of acetyl groups on ferrocene. This reaction is a typical Friedel Crafts acylation reaction, and its general form can be expressed as:
R-Fe+CH3COOCOCH3+H3PO4 → R-Fe-COOCH3+CH3COOH
Among them, R represents the remaining part of ferrocene (i.e. C9H9-). However, it should be noted that due to the presence of two cyclopentadienyl groups in ferrocene, the actual reaction may be more complex, involving the addition of two acetyl groups or the selective reaction of one cyclopentadienyl group. However, to simplify the explanation, we assume that only one acetyl group is added to the ferrocene.
In addition, it should be noted that phosphoric acid not only acts as a catalyst here, but may also participate in the formation of intermediates, but the specific mechanism is complex and usually not detailed.
Quenching reaction: Quickly pour the reaction mixture into a beaker containing crushed ice to quench the reaction and lower the temperature. This step mainly utilizes an ice water mixture to absorb the heat released from the reaction and dilute the reaction mixture to make it easier to handle.
Neutralization and washing: Slowly add solid sodium bicarbonate (NaHCO3) while stirring to neutralize the remaining acidic substances (such as acetic acid and phosphoric acid) in the reaction. The main reaction equation for this step is acid-base neutralization reaction:
CH3COOH+NaHCO3 → CH3COONa+H2O+CO2↑
H3PO4 + 3NaHCO3 → Na3PO4 + 3H2O + 3CO2
With the addition of sodium bicarbonate, the solution gradually becomes neutral and is monitored by pH test strips or pH meters.
Filtration and washing: Place the neutralized mixture in an ice bath and cool for a period of time to allow the solid acetylferrocene to fully precipitate. Then collect the solid product by filtration and wash it twice with ice water to remove impurities attached to the solid surface. The washing process does not have a direct chemical equation, but it is an important step in purifying the product.
Drying: Place the washed acetylferrocene solid in an oven and dry it to constant weight at an appropriate temperature. The drying temperature should be lower than its melting point to avoid solid melting or decomposition. The main removal during the drying process is the moisture on the solid surface, which does not involve chemical reactions.
Storage: Place the dried solid acetylferrocene in a sealed container and store it in a cool, dry, and dark place. Avoid contact with oxidants, strong acids, strong bases, and other substances to prevent their deterioration or dangerous reactions.
Discovery history of acetyl ferrocene powdere: the discovery of ferrocene is purely accidental. In 1951, pauson and kealy of Duke University treated ferric chloride with cyclopentadienyl magnesium bromide to try to obtain fulvalene, a product of diene oxidative coupling, but unexpectedly obtained a very stable orange solid. At that time, they believed that the structure of ferrocene was not sandwich, and attributed its stability to aromatic cyclopentadienyl anion. At the same time, Miller, tebboth and Tremaine also obtained the orange solid when passing the mixture of cyclopentadiene and nitrogen through a reducing iron catalyst.
Robertburns Woodward, Jeffrey Wilkinson and Ernst Otto Fischer discovered the sandwich structure of ferrocene alone, and the latter also began to synthesize nickel and cobalt ferrocene on this basis. The results of NMR and X-ray crystallography also confirmed the sandwich structure of ferrocene. The discovery of ferrocene initiated the chemistry of many π complexes between cyclopentadienyl and transition metals, and also opened a new curtain for organometallic chemistry.
In 1973 Ernst Otto Fischer of Munich University and Sir Jeffrey Wilkinson of Imperial College London were awarded the Nobel Prize in Chemistry for their outstanding contributions in the field of organometallic chemistry.
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