フェロセン

化学的特性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%.

解説フェロセン，融点173～174 ℃，沸点249 ℃．密度1.49 g cm－3．普通の有機溶媒に可溶，水に不溶．100 ℃ 以上で昇華する．反磁性で，酸の共存下で空気酸化すると，青色のビス(η5-シクロペンタジエニル)鉄(Ⅲ)イオン [Fe(C5H5)2]＋ を生じる．ほかの芳香族化合物と同じく，求電子反応が起こりやすい．森北出版「化学辞典（第2版）

用途ガソリンのアンチノック剤、ロケット燃料の燃焼助剤、医薬等の合成中間体、触媒、2.危険有害性の要約

使用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.

一般的な説明Ferrocene appears as orange crystalline solid or orange-yellow powder. Sublimes above 212 °F. Camphor odor. (NTP, 1992)

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.

純化方法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.]

定義ferrocene: An orange-red crystallinesolid, Fe(C5H5)2; m.p. 173°C. Itcan be made by adding the ioniccompound Na+C5H5- (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 theFe2+ ion. The compound can undergoelectrophilic substitution on theC5H5rings (they have some aromatic character).It can also be oxidized to theblue ion (C5H5)2Fe+. Ferrocene is the first of a class of similar complexescalled sandwich compounds. Its systematicname is di-π-cyclopentadienyliron(II).