Wln: L50TJ 0-FE--0L50TJ

Base Information

• Chemical Name: Wln: L50TJ 0-FE--0L50TJ
• CAS No.: 102-54-5
• Molecular Formula: C10H10Fe
• Molecular Weight: 186.036
• Hs Code.: Oral rat LD50: 1320 mg/kg
• NSC Number: 44012,2033
• Mol file: 102-54-5.mol

Synonyms:Iron,4-cyclopentadien-1-yl)-;WLN: L50TJ 0-FE--0L50TJ;NSC2033;NSC44012;NSC-44012

Chemical Property of Wln: L50TJ 0-FE--0L50TJ

Chemical Property:

• Appearance/Colour: Orange crystalline solid or orange-yellow powder
• Vapor Pressure: 0.03 mm Hg ( 40 °C)
• Melting Point: 172-174 ºC
• Boiling Point: 41.5 ºC at 760 mmHg
• Flash Point: 100 ºC
• PSA: 0.00000
• Density: 1.107 g/cm³(0 ºC)
• LogP: 2.63090
• Storage Temp.: Flammables area
• Sensitive.: Air & Moisture Sensitive
• Water Solubility.: practically insoluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 0
• Exact Mass: 177.950586
• Heavy Atom Count: 11
• Complexity: 143

Purity/Quality:

>99%, 98% ^*data from raw suppliers

Ferrocene 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn,N
• Hazard Codes: F,Xn,N
• Statements: 11-22-51/53-2017/11/22
• Safety Statements: 61-22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: [CH-]1[C-]=[C-][C-]=[C-]1.[CH-]1[C-]=[C-][C-]=[C-]1.[Fe+2]
• Uses: Ferrocene can be used as the additives of rocket fuel, the antiknock agent of gasoline and the curing agent of rubber and silicone resin as well as the ultraviolet absorber. The Vinyl derivative of ferrocene can be subject to ethylenic polymerization to obtain the metal-containing polymers of carbon chain skeleton which can be used as the outer coating of spacecraft. It has been found early regarding the smoke abatement effect and combustion effect of ferrocene. No matter whether being supplied in solid fuel, liquid fuel or gas fuel, it can always exert this kind of effect and this effect is more significant especially for hydrocarbons with smoke upon burning. Supplement it into the gasoline has a very good anti-hunt effect. However, due to the deposition of the iron oxide in park plug which can negatively affect ignition, its application is limited, therefore, some people also apply de-iron mixture in order to reduce the deposition phenomenon of iron. Supplement of ferrocene to the kerosene or diesel oil, due to the absence of ignition device in the engine, will have fewer adverse effects on it. In addition to the smoke abatement and combustion facilitating effect in the combustion, it also has effect of promoting the conversion of carbon monoxide into carbon dioxide. In addition, it can improve the heat of combustion and increase power efficiency to achieve the effects of energy saving and air pollution reduction. Supplement of ferrocene to the boiler fuel oil can reduce tobacco production and nozzle deposition. Supplement of 0.1% ferrocene in diesel can remove smoke by 30-70%, save fuel by 10-14%, and increase the power by 10%. There are even many more reports regarding the application of ferrocene in solid fuel of rocket fuel. Moreover, there are even cases regarding supplying it in pulverized coal for smoke-reduction agent. Upon applying the polymer water as fuel, supplement of ferrocene can reduce the smoke by several times. It can also be used as the smoke-reducing additive. In addition to the above applications, ferrocene also has other applications. When used as iron fertilizer, it can facilitate the absorption of plants on iron and increase the iron content of crops. Moreover, its derivatives can be used as pesticides. Ferrocene also has a lot of applications in industry and organic synthesis. For example, its derivatives can be used as the antioxidant of rubber or polyethylene, the stabilizer of polyurea ester, the catalyst of isobutene spasm methylation, the decomposition catalyst of polymer peroxide, and for increasing the yield of para-chlorotoluene produced during the process of chlorination of toluene. In other areas, it can also be used as anti-load additive of lubricants as well as the promoting agent of abrasive materials. It can be used as catalyst and the antiknock additive of gasoline as well as energy-saving additives for combustion promotion and smoke removal; it can be applied to various kinds of fuels such as diesel, gasoline, heavy oil and coal. Supplement of 0.1% ferrocene into diesel can save fuel by 10-14%, increase the efficiency by 10-13%, and reduce the degree of smoke in exhaust by 30-80 ‰. In addition, addition of 0.3 ‰ to the heavy oil and addition of 0.2% ferrocene to coal can both decrease the fuel consumption rate while the degree of smoke is also reduced by 30%. Ferrocene is a kind of sandwich-containing metal compound. Ferrocene and its derivatives, because of their own characteristics such as hydrophobicity, bio-oxidability, aroma, stability, low resistance, biological activity, has a wide range of application such as catalyst, the antiknock additive of gasoline, high-temperature lubricant, the intermediates of high-temperature polymer and UV absorber. Ferrocene is used as a catalyst for vulcanization, acceleration, and polymerization, as a chemical intermediate for polymeric compounds such as high temperature polymers, as an antiknock additive for gasoline, as a coating for missiles and satellites, and as a high-temperature lubricant. In ultraviolet stabilizers and smoke depressants for polymers; to increase the burn rate of rocket propellants; to prevent erosion of space capsule shields; to improve the viscosity of lubricants; to catalyze polymerization reactions; to catalyze combustion; some derivatives used as hematinic agents Antiknock additive for gasoline; catalyst.
• Production method: It can be produced either by the heating reaction between iron powder and cyclopentadiene in nitrogen atmosphere of 300 ℃ or the reaction between anhydrous ferric chloride together with the sodium cyclopentadienyl in tetrahydrofuran. Alternatively, it can also produced by electrolytic synthesis method. Taking cyclopentadiene, ferrous chloride, and diethylamine as raw material for synthesis of ferrocene can operate according to the following protocol. Upon stirring, add anhydrous ferric chloride (FeCl3) in several times to the tetrahydrofuran solution; further add iron powder into it and have heating reflux for 4.5 h under the protection of nitrogen gas, resulting in ferrous chloride solution. Further remove tetrahydrofuran solvent by evaporation under reduced pressure to give nearly dry residue. Under ice-cooling condition, add the mixture of cyclopentadienyl and diethylamine and stir vigorously at room temperature for 6-8h; remove the excess amount of amine through evaporation under reduced pressure and extract the residue with petroleum ether under reflux. The extract is subject to immediate filtering; evaporate the solvent to obtain ferrocene crude product. Employ pentane or cyclohexane for recrystallization, or apply sublimation method for extract purified product with the yield of refined product being 73-84%.
• Physical properties: Orange crystals; camphor-like odor; melts at 172.5°C; vaporizes at 249°C; sublimes above 100°C; thermally stable above 500°C; insoluble in water; soluble in alcohol, ether and benzene; also soluble in dilute nitric acid and concentrated sulfuric acid forming a deep red solution that fluoresces.

Technology Process of Wln: L50TJ 0-FE--0L50TJ

There total 741 articles about Wln: L50TJ 0-FE--0L50TJ which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

[C6H5S(O)CH2](1-)*Li(1+)=[C6H5S(O)CH2]Li (59501-96-1) + (C5H5)Fe[P(OC6H5)3]2Cl (84430-52-4) → ferrocene (102-54-5,55404-68-7) + bis(phenylthio)methane (3561-67-9) + 1,2-bis(phenylthio)ethane (622-20-8) + diphenyldisulfane (882-33-7) + lithium chloride

Guidance literature:

In tetrahydrofuran; mixing reactants in THF at -78°C, slow warming to room temp. / further products; evapn. in vac., extn. with pentane, ether and finally acetone or CH2Cl2, concn., chromy. on Al2O3, purifn. by crystn., distn. or sublimation;

DOI:10.1016/S0022-328X(00)86902-8

Reference yield: 98.0%

ferrocenium hexafluorophosphate + tetra-n-butylammonium tetramethylaurate(III) → ferrocene (102-54-5,55404-68-7) + gold (7440-57-5,457905-15-6)

Guidance literature:

In acetonitrile; byproducts: CH4, C2H6; inert atmosphere;

DOI:10.1021/om990043s

Reference yield: 97.0%

ferrocenium hexafluorophosphate + tetrabutylammonium dimethylaurate(I) (228118-52-3) → ferrocene (102-54-5,55404-68-7) + gold (7440-57-5,457905-15-6)

Guidance literature:

In tetrahydrofuran; byproducts: CH4, C2H6; He-atmosphere; addn. of 1 equiv. of Cp2FePF6 to soln. of aurate at -196°C, warming to room temp.;

DOI:10.1021/om990043s

upstream raw materials:

cyclopenta-1,3-diene

dimethylacetylene

acetylene-d2

iron

Downstream raw materials:

η-fluorene-η-cyclopentadienyliron(II) hexafluorophosphate

η-biphenyl-η-cyclopentadienyliron(II) hexafluorophosphate

η-benzhydrol-η-cyclopentadienyliron(II) hexafluorophosphate

ferrocenium

Refernces

• 1、 Cotton, F. A.,Reynolds, L. T.. "". . p. 269 - 273. Retrieved 1958.
• 2、 King. "". . p. 1429. Retrieved 1968.
• 3、 Dawoodi, Z.,Eaborn, C.,Pidcock, A.. "". . p. 95 - 104. Retrieved 1979.
• 4、 Amiens, C.,Balavoine, G.,Guibe, F.. "Oxidatively induced nucleophilic capture vs. degradation of cyclopentadienyl iron derivatives of simple carboxylic acids and of α-amino acids. A comparative study". . p. 207 - 219. Retrieved 1993.
• 5、 Zheng, Tu Cai,Cullen, William R.,Rettig, Steven J.. "Multinuclear complexes derived from ferrocenylphosphines and triruthenium dodecacarbonyl". . p. 3594 - 3604. Retrieved 1994.
• 6、 Babin, V. N.,Belousov, Yu. A.,Lyatifov, I. R.,Materikova, R. B.,Gumenyuk, V. V.. "AZOLE ANIONS AS ONE-ELECTRON REDUCERS OF FERRICINIUM SALTS". . p. C11 - C12. Retrieved 1981.
• 7、 Wrackmeyer, Bernd,Klimkina, Elena V.,Ackermann, Tamara,Milius, Wolfgang. "Ferrocenylaluminum-pyridine adducts, lithium tetra(ferrocenyl)alanate, and the molecular structure of tri(ferrocenyl)aluminum-pyridine". . p. 3941 - 3948. Retrieved 2009.
• 8、 Alessandra Quadrelli,Kraatz, Heinz-Bernhard,Poli, Rinaldo. "Oxidation and Protonation of Transition Metal Hydrides: Role of an Added Base as Proton Shuttle and Nature of Protonated Water in Acetonitrile". . p. 5154 - 5162. Retrieved 1996.
• 9、 Rosenblum, M.,Santer, J. O.. "". . p. 5517 - 5518. Retrieved 1959.
• 10、 DiMaio, Anthony-Joseph,Rheingold, Arnold L.,Chin, Teen T.,Pierce, David T.,Geiger, William E.. "Electrochemical and structural characterization of cis-and trans-[Cp(CO)Ru(μ-As(C6H5)2)]2, isomers that undergo two-electron-transfer oxidations". . p. 1169 - 1176. Retrieved 1998.