Hydroformylation
| Hydroformylation | |
|---|---|
| Reaction type | Addition reaction |
| Identifiers | |
| RSC ontology ID | RXNO:0000272 |
Hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes from alkenes. The process was developed by the German chemist Otto Roelen in 1938, who discovered the reaction on which the process is based during his investigations of the Fischer-Tropsch process. This chemical reaction entails the net addition of a formyl group (CHO) and a hydrogen atom to a carbon-carbon double bond. This process has undergone continuous growth since its invention: Production capacity reached 6.6×106 tons in 1995. It is important because aldehydes are easily converted into many secondary products. For example, the resulting aldehydes are hydrogenated to alcohols that are converted to plasticizers or detergents. Hydroformylation is also used in speciality chemicals, relevant to the organic synthesis of fragrances and drugs. The development of hydroformylation, which originated within the German coal-based industry, is considered one of the premier achievements of 20th-century industrial chemistry.
The process typically entails treatment of an alkene with high pressures (between 10 and 100 atmospheres) of carbon monoxide and hydrogen at temperatures between 40 and 200 °C.Transition metal catalysts are required. Invariably, the catalyst dissolves in the reaction medium, i.e. hydroformylation is an example of homogeneous catalysis.
The discovery of this reaction is attributed to Otto Roelen, who was investigating the Fischer-Tropsch reaction (F-T). Aldehydes and diethylketone were obtained when ethylene was added to an F-T reactor. Through these studies, Roelen discovered the involvement of cobalt catalysts. HCo(CO)4, which had been isolated prior to Roelen, was shown to be an excellent catalyst. The term oxo synthesis was created by the Ruhrchemie patent department, who expected the process to be applicable to the preparation of both aldehydes and ketones. Subsequent work demonstrated that the ligand tributylphosphine (PBu3) improved the selectivity of the cobalt-catalysed process.
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