定义Definition
氢化反应是分子氢（H₂）在催化剂（Ni、Pd、Pt、Rh、Ru 等）作用下加到不饱和键（C=C、C≡C、C=O、C≡N、芳环等）上的反应。
Hydrogenation adds molecular hydrogen (H₂) across unsaturated bonds (C=C, C≡C, C=O, C≡N, aromatic rings) with catalysts such as Ni, Pd, Pt, Rh or Ru.
多相催化机理Heterogeneous mechanism
霍里乌蒂–波拉尼机理：H₂ 在金属表面解离吸附为 H 原子，烯烃也吸附在表面；H 原子分两步加到双键碳上，产物脱附。两个 H 从同一面加上（顺式加成）。
Horiuti–Polanyi mechanism: H₂ dissociates into surface H atoms, the alkene adsorbs, H atoms add stepwise and the product desorbs; both H atoms add from the same face (syn).
选择性与催化剂Selectivity and catalysts
林德拉催化剂（Pd/CaCO₃，铅毒化）把炔烃停在顺式烯烃；拉尼镍、Pd/C 还原烯烃、硝基、苄基醚；芳环需 Rh、Ru 或高压。均相催化剂：威尔金森催化剂 RhCl(PPh₃)₃；手性 Rh-DIPAMP（诺尔斯，用于 L-多巴）和 Ru-BINAP（野依）实现不对称氢化。
Lindlar catalyst (Pd/CaCO₃ poisoned with lead) stops alkynes at cis-alkenes; Raney Ni and Pd/C reduce alkenes, nitro groups and benzyl ethers; arenes need Rh, Ru or high pressure. Homogeneous catalysts include Wilkinson’s RhCl(PPh₃)₃ and chiral Rh-DIPAMP (Knowles, for L-DOPA) and Ru-BINAP (Noyori).
工业应用Industrial uses
萨巴蒂埃（1897 年起）发展镍催化氢化，1912 年获诺贝尔奖。植物油部分氢化制人造黄油（会产生反式脂肪，现已受限）；合成氨、甲醇合成、石油加氢精制与加氢裂化都属于氢化。
Sabatier developed nickel-catalysed hydrogenation from 1897 (Nobel 1912). Partial hydrogenation of oils made margarine (forming trans fats, now restricted); ammonia, methanol synthesis, hydrotreating and hydrocracking are hydrogenations too.
反应Reactions
Pd/C、PtO₂ 或 Raney Ni，1–100 atm H₂，室温至 150 °C
Pd/C, PtO₂ or Raney Ni, 1–100 atm H₂, room temperature to 150 °C
H₂ 在金属表面解离吸附。
H₂ dissociates on the metal.
不饱和底物吸附。
The unsaturated substrate adsorbs.
H 原子逐步加成，产物脱附。
Stepwise H addition and desorption.
炔烃半氢化。
Semi-hydrogenation of an alkyne.
年表Timeline
- 1897
萨巴蒂埃镍催化氢化
Sabatier’s nickel-catalysed hydrogenation
- 1902
诺尔曼取得油脂氢化专利
Normann patents fat hydrogenation
- 1965
威尔金森催化剂
Wilkinson’s catalyst
- 2001
诺尔斯、野依因不对称氢化获诺贝尔奖
Knowles and Noyori win the Nobel Prize for asymmetric hydrogenation