双语化学辞典Chem Lexicon
类别 · 有机化学 · 烃 Organic chemistry · Hydrocarbons

烯烃Alkene

高中High school
拼音Pinyin xī tīng 别名Also olefin旧称 / 异名 烯属烃; olefin

定义Definition

烯烃是分子中含有碳碳双键 C=C 的烃。只含一个双键的开链烯烃通式为 CₙH₂ₙ(n ≥ 2),最简单的是乙烯 CH₂=CH₂。烯烃是不饱和烃,能发生加成反应和聚合反应。

Alkenes are hydrocarbons containing a carbon–carbon double bond, C=C. Open-chain alkenes with one double bond have the general formula CₙH₂ₙ (n ≥ 2); the simplest is ethene, CH₂=CH₂. Alkenes are unsaturated and undergo addition and polymerisation reactions.

结构与成键Structure and bonding

双键碳原子为 sp² 杂化,与相连的原子共平面,键角约 120°。C=C 由一个 σ 键和一个 π 键组成,π 键由两个平行 p 轨道侧面重叠形成,电子云分布在分子平面上下,较易受亲电试剂进攻。π 键使双键不能自由旋转,因此双键两端各连两个不同基团时存在顺反(E/Z)异构,如顺-2-丁烯和反-2-丁烯。

The double-bond carbons are sp² hybridised and lie in a plane with their attached atoms, at about 120°. C=C is one σ bond plus one π bond; the π bond forms by sideways overlap of parallel p orbitals, with electron density above and below the molecular plane, which is open to attack by electrophiles. The π bond prevents rotation, so when each end carries two different groups there are cis–trans (E/Z) isomers, such as cis- and trans-but-2-ene.

主要反应Main reactions

亲电加成:与溴水加成使其褪色,可用来检验 C=C;与 HBr 加成生成卤代烷;在磷酸催化下与水蒸气加成生成醇;在镍催化下与 H₂ 加成生成烷烃。氧化:冷的稀酸性高锰酸钾把烯烃氧化为二醇,热的浓高锰酸钾使双键断裂。加聚:许多烯烃分子相互加成生成聚乙烯、聚丙烯、聚氯乙烯等高分子。

Electrophilic addition: bromine water is decolourised, a test for C=C; HBr gives halogenoalkanes; steam with a phosphoric acid catalyst gives alcohols; H₂ over nickel gives alkanes. Oxidation: cold dilute acidified permanganate gives diols, and hot concentrated permanganate cleaves the double bond. Addition polymerisation: many alkene molecules join to give poly(ethene), poly(propene), PVC and other polymers.

来源与用途Sources and uses

工业上主要由石油馏分的裂化(尤其是蒸汽裂化)得到乙烯和丙烯,它们是产量最大的有机化工原料,用于生产塑料、乙醇、环氧乙烷等。乙烯也是植物激素,能促进果实成熟。

Industrially, ethene and propene come mainly from cracking (especially steam cracking) of petroleum fractions; they are the largest-volume organic feedstocks, used to make plastics, ethanol, epoxyethane and more. Ethene is also a plant hormone that speeds fruit ripening.

反应Reactions

CH2=CH2 + Br2 ⟶ CH2BrCH2Br

室温,溴水由橙色褪为无色

room temperature; bromine water turns from orange to colourless

CH2=CH2 + H2O(g) ⟶ CH3CH2OH

磷酸催化,约 300 °C、6–7 MPa

phosphoric acid catalyst, about 300 °C and 6–7 MPa

CH2=CH2 + H2 ⟶ CH3CH3

镍催化,约 150 °C

nickel catalyst, about 150 °C

n CH2=CH2 ⟶ –[CH2–CH2]ₙ–

加聚生成聚乙烯

addition polymerisation to poly(ethene)

年表Timeline

  • 1795

    荷兰化学家研究乙烯与氯气生成油状物,乙烯因此得名“成油气”(olefiant gas)

    Dutch chemists find ethene and chlorine form an oily liquid, so ethene is called olefiant (oil-forming) gas

  • 1933

    英国帝国化学工业公司发现乙烯高压聚合生成聚乙烯

    ICI discovers high-pressure polymerisation of ethene to polyethylene

  • 1953

    齐格勒发现在常压下聚合乙烯的催化剂

    Ziegler discovers catalysts that polymerise ethene at low pressure

  • 1963

    齐格勒与纳塔获诺贝尔化学奖

    Ziegler and Natta receive the Nobel Prize in Chemistry