裂解
烷烃 → 烯烃:查看反应物、产物、反应条件与来源依据,探索相关转化和合成路径。
- 试剂
- 沸石催化剂
- 条件
- 高温
- 反应类别
- 热裂解
- 方程式
- long-chain alkane -> shorter alkane + alkene
概览
热裂解或催化裂解将长链烷烃转化为较短的分子,其中包括烯烃。
转化
- 方程式
- long-chain alkane -> shorter alkane + alkene
- 试剂
- 沸石催化剂
- 反应环境
- 高温
- 反应类别
- 热裂解
- 机理
- 热裂解
- Evidence level
- 教材核心内容
参考步骤
Microscale reference: catalytic cracking
Liquid paraffin → shorter-chain hydrocarbons including an alkene
物料与用量
- Liquid paraffin — five or six drops on mineral wool; about 0.5 cm of the tube occupied
- Aluminium oxide — one microspatula
- Bromine water, 0.01 mol dm⁻³ — half-fill the receiving well; about 3 cm³ available per group
- Mineral wool — a small plug
- Ethanol or industrial denatured alcohol — microburner fuel
仪器装置
- Two microscale well plates with ported lids
- 10 cm³ gas syringe
- Straight narrow-bore glass tube and two L-shaped glass tubes
- Short lengths of silicone tubing
- Dropping pipette
- Ethanol microburner
- Eye protection
实验步骤
- Connect the gas syringe to the inlet well and half-fill the receiving well with bromine water before joining the two wells through the glass reaction tube.
- Place mineral wool two to three centimetres into the inlet end of the straight tube, add five or six drops of liquid paraffin, and place one microspatula of aluminium oxide at the opposite end.
- Assemble the tube horizontally with the paraffin nearest the gas-syringe end and the catalyst nearest the bromine-water end.
- Heat the aluminium oxide strongly first while depressing the syringe very slowly, then flick the heat over the paraffin so its vapour passes across the hot catalyst.
- Continue the slow gas flow until the bromine-water colour no longer changes or the paraffin is exhausted, then stop heating and allow all glassware to cool before dismantling.
关键控制条件
- Wear eye protection throughout setup, heating and dismantling; the narrow glass tubes can break while tubing is fitted.
- Keep the ethanol microburner upright and closed except as instructed; its vapour is highly flammable.
- Maintain a slow positive gas flow to reduce suck-back of bromine water into the hot tube.
- The product mixture shows unsaturation by bromine-water decolourisation.
底物范围
- 适用范围
- Long-chain alkanes can be cracked to produce smaller alkanes and alkenes.
- 来源说明
- Cracking gives mixtures; this route records the alkene-producing branch rather than product selectivity.
相关反应
- Hydrochlorination: Alkenes → Chloroalkanes
氯化氢在烯烃双键两端加成,可生成氯代烷。
- Hydrobromination: Alkenes → Bromoalkanes
溴化氢在烯烃双键两端加成,可生成溴代烷。
- Hydroiodination: Alkenes → Iodoalkanes
碘化氢在烯烃双键两端加成,可生成碘代烷。
- Elimination: Chloroalkanes → Alkenes
碱促进的消去反应脱去 HCl,生成烯烃。
- Elimination: Bromoalkanes → Alkenes
碱促进的消去反应脱去 HBr,生成烯烃。
- Elimination: Iodoalkanes → Alkenes
碱促进的消去反应脱去 HI,生成烯烃。
- Free radical chlorination: Alkanes → Chloroalkanes
光化学氯化可将烷烃转化为氯代烷。
- Free radical bromination: Alkanes → Bromoalkanes
光化学溴化可将烷烃转化为溴代烷。
- Hydrogenation: Alkenes → Alkanes
氢化将烯烃还原为烷烃。
- Halogen addition: Alkenes → Dihalogenoalkanes
溴加成将烯烃转化为邻二溴代烷。
- Dihydroxylation: Alkenes → Diols
冷的稀高锰酸盐溶液可将烯烃氧化为邻二醇,避免较强条件下的氧化断裂。
- Addition polymerisation: Alkenes → Addition polymers
烯烃可通过链式加成形成加聚物。
- Hydration: Alkenes → Alcohols
催化水合将烯烃转化为醇。
- Dehydration: Alcohols → Alkenes
脱水将醇转化为烯烃。
- Complete combustion: Alkanes → Carbon dioxide
烷烃在过量氧气中完全燃烧,生成二氧化碳和水。
- Epoxidation: Alkenes → Epoxides
过氧酸以协同步骤将氧转移到烯烃双键两端,形成两个 C-O 键并断开 C=C 的 π 键。两个键从同一面形成,使烯烃取代基的相对立体关系在环氧产物中保留。
参考文献
- Pearson Edexcel Level 3 Advanced GCE in Chemistry specificationPearson Education Limited · Pearson qualifications · 2024
Supports the textbook-core organic reaction routes used for displayed route and mechanism content.
- Cracking hydrocarbons on a microscaleRoyal Society of Chemistry and Nuffield Foundation · RSC Education
Provides a microscale catalyst-tube method for cracking liquid paraffin and testing the gaseous product with bromine water.