DICYCLOPENTADIENYLIRON
Ferrocene
CAS: 102-54-5;55404-68-7
Molecular Formula: C10H10Fe
DICYCLOPENTADIENYLIRON - Names and Identifiers
| Name | Ferrocene |
| Synonyms | iron Ferrocene FERROCENE Ferrocene-d10 cyclopenta-1,3-diene DICYCLOPENTADIENYLIRON IRON DICYCLOPENTADIENYL BIS(CYCLOPENTADIEN)IRON Iron dicyclopentadienyl Di(cyclopentadienyl)iron Bis(cyclopentadienyl)iron BIS(CYCLOPENTADIENYL)IRON DICYCLOPENTADIENYLIRON(II) BIS(CYCLOPENTADIENYL)IRON(+2) dicyclopenta-1,3-dien-1-yliron di-2,4-cyclopentadien-1-yliron FerroceneBiscyclopentadienyliron iron(2+) dicyclopenta-2,4-dienide |
| CAS | 102-54-5 55404-68-7 |
| EINECS | 203-039-3 |
| InChI | InChI=1/2C5H5.Fe/c2*1-2-4-5-3-1;/h2*1-3H,4H2;/rC10H10Fe/c1-2-6-9(5-1)11-10-7-3-4-8-10/h1-5,7H,6,8H2 |
DICYCLOPENTADIENYLIRON - Physico-chemical Properties
| Molecular Formula | C10H10Fe |
| Molar Mass | 186.03 |
| Density | 1.490 |
| Melting Point | 172-174 °C (lit.) |
| Boling Point | 249 °C (lit.) |
| Flash Point | 100°C |
| Water Solubility | practically insoluble |
| Vapor Presure | 0.03 mm Hg ( 40 °C) |
| Appearance | Yellow to orange solid powder |
| Color | orange |
| Exposure Limit | ACGIH: TWA 10 mg/m3; TWA 1 mg/m3OSHA: TWA 15 mg/m3; TWA 5 mg/m3NIOSH: TWA 10 mg/m3; TWA 5 mg/m3; TWA 1 mg/m3 |
| Merck | 14,4037 |
| Storage Condition | Store below +30°C. |
| Stability | Stable at room temperature. Incompatible with strong oxidizing agents. Highly flammable. |
| Sensitive | Air & Moisture Sensitive |
| MDL | MFCD00001427 |
| Physical and Chemical Properties | Ferrocene is a metal-organic compound. At room temperature for orange-yellow powder, camphor odor. Melting point of 172 degrees -174 degrees, boiling point of 249 degrees, insoluble in water, soluble in benzene, ether, gasoline, diesel and other organic solvents. With acid, alkali, UV does not occur, chemical stability, no decomposition within 400 degrees. |
| Use | Used as energy-saving smoke suppression additive: can be used for a variety of fuels, such as diesel, gasoline, heavy oil, coal and so on. By adding 0.1% ferrocene to the diesel fuel, the fuel oil can be saved by 10-14%, the improvement rate is 10-13%, and the smoke in the exhaust gas is reduced by 30-80 ‰. In addition, adding 0.3‰ in the heavy oil, coal to add 0.2% ferrocene, can reduce fuel consumption, at the same time, smoke decreased by 30%. |
DICYCLOPENTADIENYLIRON - Risk and Safety
| Risk Codes | R11 - Highly Flammable R22 - Harmful if swallowed R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R2017/11/22 - |
| Safety Description | S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| UN IDs | UN 1325 4.1/PG 2 |
| WGK Germany | 2 |
| RTECS | LK0700000 |
| TSCA | Yes |
| HS Code | 29310095 |
| Hazard Class | 4.1 |
| Packing Group | II |
| Toxicity | LD50 orally in Rabbit: 1320 mg/kg LD50 dermal Rat > 3000 mg/kg |
DICYCLOPENTADIENYLIRON - Introduction
It smells of camphor. The maximum absorption wavelength is 358mm. Flammable. Can volatilize with water vapor. Soluble in benzene, ethanol, ether, gasoline, diesel and other organic solvents. It is also soluble in dilute nitric acid and concentrated sulfuric acid to become dark red, with blue fluorescence, almost insoluble in water, 10% sodium hydroxide and boiling concentrated hydrochloric acid.
Last Update：2022-10-16 17:11:33
DICYCLOPENTADIENYLIRON - Reference Information
| sublimation point | 100°C |
| LogP | 3.711 at 22℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| An organic transition metal compound with aromatic properties | Ferrocene is an organic transition metal compound with aromatic properties, also called dicyclopentadienyl iron and dicyclopentadienyl iron. The molecular structure contains one divalent iron cation and two cyclopentadienyl anions. It is the raw material for the production of ferrocene, in the 50th century, humans used cyclopentadiene magnesium bromide to react with anhydrous ferric chloride for the first time. It is orange-yellow needle-like crystals and powder at room temperature. It has a camphor-like smell and is a non-polar compound. Easily soluble in methanol, ethanol, ether, petroleum ether, gasoline, kerosene, diesel, dichloromethane, benzene, toluene, xylene and other organic solvents, due to the relatively large polarity of ethanol, it is usually best to dissolve with toluene. Insoluble in water , soluble in concentrated sulfuric acid, insoluble in boiling caustic soda solution and hydrochloric acid, does not decompose. Its molecules are polar, with high thermal stability, chemical stability and radiation resistance. It has a wide range of applications in industry, agriculture, medicine, aerospace, energy saving, ring protection and other industries. The main applications are introduced as follows: (1) energy-saving smoke suppressive and antiknock agent used as fuel. For example, it is used to make gasoline antiknock agent, burning rate catalyst for rocket propellant, solid fuel for aerospace, etc. (2) Used as a catalyst. If it is used to make synthetic ammonia catalyst, as a curing agent for silicone resin and rubber, it can prevent the degradation of polyethylene to light. It can be used for agricultural mulching film, which can be naturally degraded and broken within a certain period of time, and does not Affect farming and fertilization. (3) Used as gasoline antiknock agent. It can replace the toxic tetraethyl lead in gasoline as an anti-knock agent to make high-grade unleaded gasoline to eliminate the pollution of fuel emissions to the environment and the toxicity to the human body. (4) used as radiation absorber, heat stabilizer, light stabilizer and smoke inhibitor. (5) In terms of chemical properties, ferrocene is similar to aromatic compounds, is not prone to addition reactions, and is prone to electrophilic substitution reactions. It can undergo metallization, acylation, alkylation, sulfonation, and formylation. As well as complex exchange, a series of derivatives with a wide range of uses can be prepared. |
| use | ferrocene can be used as a rocket fuel additive, an antiknock agent for gasoline, a curing agent for rubber and silicone resin, and an ultraviolet absorber. The vinyl derivatives of ferrocene can undergo ethylenic polymerization to obtain metal-containing polymers with carbon chain skeletons, which can be used as outer coatings for spacecraft. The smoke-absorbing and combustion-supporting effect of ferrocene was discovered earlier. It is not only added to solid fuel, liquid fuel or gas fuel, which can exert this effect, especially for hydrocarbons that produce large smoke during combustion. More significant. Its addition has a good anti-seismic effect in gasoline, but it is limited due to the deposition of iron oxide on the spark plug to affect ignition. For this reason, some people also use iron discharge mixture to reduce iron deposition. Ferrocene is added to kerosene or diesel. Since the engine does not use an ignition device, it has less adverse effects. In addition to smoke and combustion, it also promotes the conversion of carbon monoxide into carbon dioxide. In addition, it can increase combustion heat and power in combustion to achieve the effect of energy saving and reducing air pollution. The addition of ferrocene to boiler fuel oil can reduce smoke generation and nozzle carbon deposits. Adding 0.1% to diesel oil can reduce smoke by 30-70%, save oil by 10-14%, and increase power by 10%. There are more reports on the use of ferrocene in solid rocket fuel, and even mixed in pulverized coal as a deceleration smoke agent. When using polymer waste as fuel, the addition of ferrocene can reduce smoke several times, and it can also be used as a smoke-reducing additive for plastics. In addition to the above applications, ferrocene has other applications. As an iron fertilizer, it is beneficial to plant absorption, growth rate plus the iron content of crops. Its derivatives can be used as pesticides. There are also many uses in the industrial and organic synthesis of ferrocene. For example, its derivatives can be used as antioxidants for rubber or polyethylene, stabilizers for polyurea esters, isobutylene spasm methylation catalysts, The decomposition catalyst of high molecular peroxides increases the yield of para-chlorotoluene in toluene chlorination. In other aspects, it can be used as an anti-load additive for lubricating oil and an accelerator for grinding materials. Used as a catalyst and gasoline anti-knock additive as an energy-saving, smoke-absorbing and combustion-supporting additive: It can be used in various fuels, such as diesel, gasoline, heavy oil, coal, etc. Adding 0.1% ferrocene to vehicle diesel can save 10-14% of fuel oil, increase the rate by 10-13%, and reduce the smoke level in exhaust gas by 30-80 ‰. In addition, adding 0.3‰ to heavy oil and 0.2% ferrocene to coal can reduce fuel consumption and 30% smoke. Adding ferrocene to gasoline can also increase the octane number of gasoline and improve the anti-knock combustion performance of fuel. Ferrocene is a metal organic compound with a sandwich structure. Ferrocene and its derivatives are widely used because of their own characteristics, such as hydrophobicity, biooxidizability, aromaticity, stability, low properties, biological activity, etc. As a catalyst. Antiknock additive for gasoline. High temperature lubricant. High temperature polymer intermediate. Ultraviolet light absorber. |
| production method | it is obtained by heating iron powder and cyclopentadiene in a nitrogen atmosphere at 300 ℃, or by reacting anhydrous ferrous chloride and cyclopentadiene sodium in tetrahydrofuran. it can also be obtained by electrolytic synthesis. ferrocene can be synthesized by using cyclopentadiene, ferrous chloride and diethylamine as raw materials. Under stirring, anhydrous ferric chloride (FeCL3) is added to tetrahydrofuran in stages, then iron powder is added, and heated and refluxed under nitrogen protection for 4.5h to obtain ferrous chloride solution. The solvent tetrahydrofuran is evaporated under reduced pressure to obtain a nearly dry residue. Under the cooling of ice bath, the mixture of cyclopentadiene and diethylamine is added, and the mixture is vigorously stirred for 6-8h at room temperature, the excess amine is evaporated under reduced pressure, and the residue is extracted by reflux with petroleum ether. The extract is filtered while hot, and the solvent is evaporated to obtain crude ferrocene. Recrystallization with pentane or cyclohexane, or pure by sublimation method, that is, the yield of refined products is 73-84%. |
| category | toxic substances |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 1320 mg/kg; Oral-mouse LD50: 832 mg/kg |
| flammability hazard characteristics | combustible, the fire field discharges iron-containing spicy and irritating smoke |
| storage and transportation characteristics | warehouse is low temperature, ventilated and dry; Store separately from oxidant |
| fire extinguishing agent | water, carbon dioxide, dry powder, sand |
| occupational standard | TWA 10 mg/m3; STEL 20 mg/m3 |
| spontaneous combustion temperature | >150°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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