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In organic chemistry, hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes (R−CH=O) from alkenes (R 2 C=CR 2). [ 1 ] [ 2 ] This chemical reaction entails the net addition of a formyl group ( −CHO ) and a hydrogen atom to a carbon-carbon double bond .
This metal carbonyl is used as a reagent and catalyst in organometallic chemistry and organic synthesis, and is central to much known organocobalt chemistry. [2] [3] It is the parent member of a family of hydroformylation catalysts. [4]
In 1953 evidence was disclosed that it is the active catalyst for the conversion of alkenes, CO, and H 2 to aldehydes, a process known as hydroformylation (oxo reaction). [12] Although the use of cobalt-based hydroformylation has since been largely superseded by rhodium-based catalysts, the world output of C 3 –C 18 aldehydes produced by ...
Metal carbonyls are used in a number of industrially important carbonylation reactions. In the oxo process, an alkene, hydrogen gas, and carbon monoxide react together with a catalyst (such as dicobalt octacarbonyl) to give aldehydes. Illustrative is the production of butyraldehyde from propylene: CH 3 CH=CH 2 + H 2 + CO → CH 3 CH 2 CH 2 CHO
Oxo alcohols are alcohols that are prepared by adding carbon monoxide (CO) and hydrogen (usually combined as synthesis gas) to an olefin to obtain an aldehyde using the hydroformylation reaction and then hydrogenating the aldehyde to obtain the alcohol. [1]
It involves treatment of the alkene with a mixture of hydrogen gas and carbon monoxide in the presence of a metal catalyst. Illustrative is the generation of butyraldehyde by hydroformylation of propylene: H 2 + CO + CH 3 CH=CH 2 → CH 3 CH 2 CH 2 CHO. One complication with this process is the formation of isomers, such as isobutyraldehyde:
Often cross-coupling reactions require metal catalysts. One important reaction type is this: R−M + R'−X → R−R' + MX (R, R' = organic fragments, usually aryl; M = main group center such as Li or MgX; X = halide) These reactions are used to form carbon–carbon bonds but also carbon-heteroatom bonds.
Typical catalysts are platinum, and redox-active oxides of iron, vanadium, and molybdenum. In many cases, catalysts are modified with a host of additives or promoters that enhance rates or selectivities. Important homogeneous catalysts for the oxidation of organic compounds are carboxylates of cobalt, iron, and manganese