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In organic chemistry, olefin metathesis is an organic reaction that entails the redistribution of fragments of alkenes (olefins) by the scission and regeneration of carbon-carbon double bonds. [ 1 ] [ 2 ] Because of the relative simplicity of olefin metathesis, it often creates fewer undesired by-products and hazardous wastes than alternative ...
The Shell higher olefin process (SHOP) is a chemical process for the production of linear alpha olefins via ethylene oligomerization and olefin metathesis invented and exploited by Shell plc. [1] The olefin products are converted to fatty aldehydes and then to fatty alcohols, which are precursors to plasticizers and detergents.
The metal-mediated processes include a carbonyl-olefination and an olefin–olefin metathesis event. There are two general mechanistic schemes to perform this overall transformation: one, reaction of a [M=CHR 1] reagent with an alkene to generate a new metal alkylidene, which then couples with a carbonyl group to form the desired substituted alkene and an inactive [M=O] species (type A); two ...
Grubbs catalysts are of interest for olefin metathesis. [25] [26] It is mainly applied to fine chemical synthesis. Large-scale commercial applications of olefin metathesis almost always employ heterogeneous catalysts or ill-defined systems based on ruthenium trichloride. [6]
The reaction is an example of cross metathesis. The utility of the reaction is driven by the low cost of ethylene as a reagent and its selectivity. It produces compounds with terminal alkene functional groups (α-olefins), which are more amenable to other reactions such as polymerization and hydroformylation. The general reaction equation is:
Corey–Winter olefin synthesis; Corey–Winter reaction; Cornforth rearrangement; Coupling reaction; Crabbé reaction; Craig method; Cram's rule of asymmetric induction; Creighton process; Criegee reaction; Criegee rearrangement; Cross metathesis; Crum Brown–Gibson rule; Curtius degradation; Curtius rearrangement, Curtius reaction ...
Where shorter chains are wanted, as they for the production of surfactants, then processes incorporating a olefin metathesis step, such as the Shell higher olefin process are important. Olefin metathesis is also used commercially for the interconversion of ethylene and 2-butene to propylene.
Ring-closing metathesis (RCM) is a widely used variation of olefin metathesis in organic chemistry for the synthesis of various unsaturated rings via the intramolecular metathesis of two terminal alkenes, which forms the cycloalkene as the E-or Z-isomers and volatile ethylene. [1] [2]