Ferrocen Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
ORANGEFARBENE KRISTALLE MIT CHARAKTERISTISCHEM GERUCH.
CHEMISCHE GEFAHREN
Beim Verbrennen Bildung von giftigen Rauchen. Reagiert sehr heftig mit Ammoniumperchlorat oder Tetranitromethan. Reagiert mit Quecksilber(II)nitrat.
ARBEITSPLATZGRENZWERTE
TLV: (als Eisen) 10 mg/m?(als TWA); (ACGIH 2005).
MAK nicht festgelegt (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den K?rper durch Inhalation und durch Verschlucken.
INHALATIONSGEFAHREN
Verdampfung bei 20°C vernachl?ssigbar; eine gesundheitssch?dliche Partikelkonzentration in der Luft kann jedoch beim Dispergieren schnell erreicht werden.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Reizt m?glicherweise mechanisch.
LECKAGE
Verschüttetes Material in Beh?ltern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Pers?nliche Schutzausrüstung: Atemschutzger?t, P1-Filter für inerte Partikel.
R-S?tze Betriebsanweisung:
R11:Leichtentzündlich.
R22:Gesundheitssch?dlich beim Verschlucken.
R51/53:Giftig für Wasserorganismen, kann in Gew?ssern l?ngerfristig sch?dliche Wirkungen haben.
S-S?tze Betriebsanweisung:
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S22:Staub nicht einatmen.
Chemische Eigenschaften
Ferrocene, a metallocene, appears as bright orange salt-like crystals when crystallized from alcohol. It has a camphor-like odor and forms an orange crystalline solid. The compound is insoluble in water but soluble in benzene, ether, and alcohol, with an iron content of 29.4–30.6%.
Physikalische Eigenschaften
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.
Verwenden
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.
Definition
ferrocene: An orange-red crystallinesolid, Fe(C
5H
5)
2; m.p. 173°C. Itcan be made by adding the ioniccompound Na
+C
5H
5- (cyclopentadienylsodium, made from sodium andcyclopentadiene) to iron(III) chloride.In ferrocene, the two rings are parallel,with the iron ion sandwiched betweenthem (hence the namesandwich compound: see formula).The bonding is between pi orbitalson the rings and d-orbitals on theFe
2+ ion. The compound can undergoelectrophilic substitution on theC
5H
5rings (they have some aromatic character).It can also be oxidized to theblue ion (C
5H
5)
2Fe
+. Ferrocene is the first of a class of similar complexescalled sandwich compounds. Its systematicname is di-π-cyclopentadienyliron(II).
Vorbereitung Methode
Ferrocene is produced from the reaction of cyclopentadiene
with reduced iron in the presence of metal oxides. There is
also a two-stage production process in which produced iron
(II)oxide (stage 1) is reacted with cyclopentadiene.
Application
Ferrocene, the most well-known cyclopentadienyl sandwich compound, contains up to 30% iron. It is primarily used as an organometallic framework and is widely applied in fields such as aerospace, petroleum, chemical engineering and biomedicine. For example:
(1) Biomedicine: Research has revealed that ferrocene and its derivatives possess a wide range of pharmacological activities, such as anti-anaemic, antibacterial, anti-proliferative, anti-malarial, anti-tubercular and antiviral properties. Consequently, it can be utilised in the development of drug candidates for the treatment of iron-deficiency anaemia, cancer (e.g. tamoxifen, a drug used to treat hormone-dependent breast cancer) and malaria (e.g. chloroquine) [2].
(2) Aerospace sector: Among various catalysts for combustion rates, ferrocene and its derivatives demonstrate excellent catalytic performance. Currently, ferrocene-based catalysts for the oxidation of solid rocket propellants are in widespread use [3].
(3) Chemical Industry: Ferrocene is a well-known iron precursor molecule for depositing iron-containing films in processes such as chemical vapour deposition (CVD) and can be used to prepare iron nanoparticles. Ferrocene precursors are commonly used as suspension catalysts in the synthesis of carbon nanotubes (CNTs)[4]. Furthermore, it can serve as an iron source for the manufacture of low-cost catalyst supports used in fixed-bed CVD synthesis of carbon nanotubes.
(4) Petroleum sector: Ferrocene can be added to kerosene or diesel to enhance combustion efficiency and reduce carbon monoxide emissions, thereby achieving energy savings and reducing atmospheric pollution.
Allgemeine Beschreibung
Ferrocene appears as orange crystalline solid or orange-yellow powder. Sublimes above 212 °F. Camphor odor. (NTP, 1992)
Air & Water Reaktionen
Sensitive to prolonged exposure to air and may be sensitive to light. Insoluble in water.
Reaktivit?t anzeigen
Ferrocene reacts violently with tetranitromethane. . Contact of tetranitromethane with Ferrocene under various conditions leads to violent explosion, [Trans. Met. Chem., 1979, 4, 207-208].
Hazard
Moderate fire risk. Evolves toxic products
on decomposition and heating.
Health Hazard
Dicyclopentadienyl iron causes
changes in blood parameters and hepatic
cirrhosis.
The toxicological properties of dicyclopentadienyl
iron have not been extensively
investigated. However, it has been used as a
preventive and therapeutic iron deficiency
drug, and its utilization is listed as tolerable.
Brandgefahr
Flash point data for Ferrocene are not available. Ferrocene is probably combustible.
Sicherheitsprofil
Poison by
intraperitoneal and intravenous routes.
Moderately toxic by ingestion. Questionable
carcinogen with experimental tumorigenic
data. Mutation data reported. Flammable;
reacts violently with NH4ClO4. When heated
to decomposition it emits acrid smoke and
irritating fumes.
m?gliche Exposition
Used as additive in fuel oil; antiknock
agent in gasoline fuel; used in making rubber, silicone
resins, high-temperature polymers and lubricants; interme diate for high-temperature polymers; as a smoke suppres sant and catalyst
Carcinogenicity
Ferrocene was administered by
intramuscular injection at a dose of 5175 mg/kg/2 years.
By the criterion established by the Registry of Toxic Effects
of Chemical Substances (RTECS), ferrocene was an equivocal
tumorigenic agent and tumors were most evident at the
site of multiple injections.
Versand/Shipping
UN1325 Flammable solids, organic, n.o.s.,
Hazard Class: 4.1; Labels: 4.1-Flammable solid.
l?uterung methode
Purify it by crystallisation from pentane or cyclohexane (also *C6H6 or MeOH can be used). It is moderately soluble in Et2O and sublimes readily above 100o. Crystallisation from EtOH gave material m 172.5-173o. [Wilkinson Org Synth Coll Vol IV 473 1963, Miller J Chem Soc 632 1952.] It has also been crystallised from methanol and sublimed in vacuo. [Saltiel et al. J Am Chem Soc 109 1209 1987, Beilstein 16 IV 1783.]
Inkompatibilit?ten
Violent reaction with ammonium per chlorate, tetranitromethane, mercury(II) nitrate. Incompa tible with oxidizers (chlorates, nitrates, peroxides, perman ganates, perchlorates, chlorine, bromine, fluorine, etc.);
contact may cause fires or explosions. Keep away from
alkaline materials, strong bases, strong acids, oxoacids,
epoxides.
Peroxomonosulfuric acid. Decomposes @≧465 ℃.
Ferrocen Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
1,1'-Bis (di-t-butylphosphino)ferrocene palladium dichloride,
1,1'-FERROCENEDICARBOXALDEHYDE
1 1'-BIS(DIPHENYLPHOSPHINO)FERROCENE
1,1'-Bis(diphenylphosphino)ferrocene
1,1'-Dibutylferrocen
1,1'-Bis(di-tert-butylphosphino)ferrocene
Ferrocene derivative
dibuty cebacate with ferric chloride
Butylferrocen
1,1'-Dimethylferrocen
1,1'-Diacetylferrocene
1-DIPHENYLPHOSPHINO-1'-(DI-TERT-BUTYLPH&
1,1'-Bis(diisopropylphosphino)ferrocene
Chlorocarbonyl ferrocene
1,1'-DIETHYLFERROCENE
Tricarbonyl-(methylcyclopentadie-nyl)-mangan
Benzoylferrocen
Ferrocenmetaborsure
1,1'-binaphthalene-2,2'-diyl diacetate
Acetylferrocen
ferroceron
