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alkane metathesis wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 examples and catalysts 2 see also 3 references toggle the table of contents alkane metathesis 1 language čeština edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia type of chemical reaction alkane metathesis is a class of chemical reaction in which an alkane is rearranged to give a longer or shorter alkane product it is similar to olefin metathesis except that olefin metathesis cleaves and recreates a carbon carbon double bond but alkane metathesis operates on a carbon carbon single bond examples and catalysts edit alkane metathesis is catalyzed by metal containing compounds or complexes one such class of catalyst systems discovered and developed by the group of jean marie basset comprises tantalum hydride supported on silica sio 2 tah at temperatures of 25 c to 200 c these systems catalyze the conversion of ethane to give methane propane and traces of butane 1 cross metathesis can also take place for example methane and propane can react to give two molecules of ethane ethane reacts with toluene to give ethylbenzene and xylene the reaction involves metallocyclobutane intermediates just as in olefin metathesis 2 dual catalyst systems have also been developed which are effective for the metathesis of higher alkanes these systems are based on the tandem operation of two catalysts one for transfer dehydrogenation and one for olefin metathesis a heterogeneous system consisting of pt on alumina mixed with w oxide on silica was reported by burnett and hughes 3 systems based on pincer iridium dehydrogenation catalysts and either schrock type mo based olefin metathesis catalysts have been reported by brookhart and goldman 4 because the iridium based catalysts show selectivity for the termini of n alkanes these systems have the unique ability to effect alkane metathesis with some selectivity for product molecular weight thus for example n hexane can be converted to ethane and n decane as the major products numerous applications for alkane metathesis involving petrochemicals and fuels can be envisaged for example the conversion of n hexane to n decane and ethane has been proposed for the purpose of improving the overall yield of diesel grade n alkane c 9 h 20 to c 19 h 40 from fischer tropsch reactors which convert syngas to a broad range of n alkanes scott goldman and brookhart have reported the metathesis of cycloalkanes with the pincer ir mo system cyclooctane cyclo c 8 h 16 for example is converted to a mixture of cyclohexadecane cyclo c 16 h 32 and higher rings as well as polymers 5 see also edit alkene metathesis alkyne metathesis references edit vidal v theolier a thivolle cazat j basset j m 1997 metathesis of alkanes catalyzed by silica supported transition metal hydrides science 276 5309 99 102 doi 10 1126 science 276 5309 99 pmid 9082995 basset jean marie copéret christophe lefort laurent maunders barry m maury olivier le roux erwan saggio guillaume soignier sophie soulivong daravong sunley glenn j taoufik mostafa thivolle cazat jean 2005 primary products and mechanistic considerations in alkane metathesis journal of the american chemical society 127 24 8604 8605 bibcode 2005jachs 127 8604b doi 10 1021 ja051679f pmid 15954760 burnett robert l hughes thomas r 1973 mechanism and poisoning of the molecular redistribution reaction of alkanes with a dual functional catalyst system journal of catalysis 31 55 64 doi 10 1016 0021 9517 73 90270 4 goldman a s roy a h huang z ahuja r schinski w brookhart m 2006 catalytic alkane metathesis by tandem alkane dehydrogenation olefin metathesis science 312 5771 257 261 bibcode 2006sci 312 257g doi 10 1126 science 1123787 pmid 16614220 ahuja ritu kundu sabuj goldman alan s brookhart maurice vicente brian c scott susannah l 2008 catalytic ring expansion contraction and metathesis polymerization of cycloalkanes chemical communications 2 253 255 doi 10 1039 b712197k pmid 18092104 retrieved from https en wikipedia org w index php title alkane_metathesis oldid 1349664257 category carbon carbon bond forming reactions hidden categories articles with short description short description is different from wikidata this page was last edited on 18 april 2026 at 10 39 utc page was rendered with parsoid text is available under the creative commons 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