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ziegler process 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 process details 2 applications 3 see also 4 references toggle the table of contents ziegler process 5 languages čeština deutsch español euskara فارسی 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 in organic chemistry the ziegler process also called the ziegler alfol synthesis is a method for producing fatty alcohols from ethylene using an organoaluminium compound the reaction produces linear primary alcohols with an even numbered carbon chain the process uses an aluminum compound to oligomerize ethylene and allow the resulting alkyl group to be oxygenated the usually targeted products are fatty alcohols which are otherwise derived from natural fats and oils fatty alcohols are used in food and chemical processing they are useful due to their amphipathic nature the synthesis route is named after karl ziegler who described the process in 1955 1 2 process details edit the ziegler alcohol synthesis involves oligomerization of ethylene using triethylaluminium followed by oxidation 2 the triethylaluminium is produced by action of aluminium ethylene and hydrogen gas in the production process two thirds of the triethylaluminium produced is recycled back into the reactor and only one third is used to produce the fatty alcohols the recycling step is used to produce triethylaluminium at a higher yield and with less time triethylaluminium reacts with ethylene to form higher molecular weight trialkylaluminium the number of equivalents of ethylene n equals the total number of monomer units being grown on the initial ethylene chains where n x y z and x y and z are the number of ethylene units per chain trialkylaluminium is oxidized with air to form aluminum alkoxides and finally hydrolyzed to aluminum hydroxide and the desired alcohols 1 al 3ethylene 1 5h 2 al c 2 h 5 3 al c 2 h 5 3 n ethylene al ch 2 ch 2 n ch 2 ch 3 3 al ch 2 ch 2 n ch 2 ch 3 3 o 2 al o ch 2 ch 2 n ch 2 ch 3 3 al o ch 2 ch 2 n ch 2 ch 3 3 3h 2 o al oh 3 ch 3 ch 2 ch 2 ch 2 n oh the temperature of the reaction influences the molecular weight of alcohol growth temperatures in the range of 60 120 c form higher molecular weight trialkylaluminium while higher temperatures e g 120 150 c cause thermal displacement reactions that afford α olefin chains above 150 c dimerization of the α olefins occurs applications edit aluminum hydroxide the byproduct of the synthesis can be dehydrated to give aluminium oxide which at high purities has a high commercial value one modification of the ziegler process is called the epal process in this process chain growth is optimized to produce alcohols with narrow molecular weight distribution synthesis of other alcohols use ziegler and the updated epal process such as the transalkylation of styrene to form 2 phenylethanol diethylaluminum hydride can be employed in place of triethylaluminium 1 see also edit guerbet reaction a route for the production of branched fatty alcohols references edit 1 2 3 klaus noweck wolfgang grafahrend 2006 fatty alcohols ullmann s encyclopedia of industrial chemistry weinheim wiley vch doi 10 1002 14356007 a10_277 pub2 isbn 978 3 527 30673 2 1 2 zerong wang ziegler alcohol synthesis ziegler higher alcohol synthesis alfol process ziegler alfol process ziegler alfol synthesis in comprehensive organic name reactions and reagents 2010 john wiley sons inc online isbn 9780470638859 v t e alcohols by consumption alcohols found in alcoholic drinks 1 propanol 2 methyl 1 butanol ethanol isoamyl alcohol isobutanol phenethyl alcohol tert amyl alcohol tert butyl alcohol tryptophol medical alcohol ethchlorvynol methylpentynol methanol poisoning ethanol toxic alcohols isopropyl alcohol methanol primary alcohols 1 methanol 4 methylcyclohexanemethanol aminomethanol cyclohexylmethanol methoxymethanol methylazoxymethanol trifluoromethanol ethanol 1 aminoethanol 2 2 2 trichloroethanol 2 2 2 trifluoroethanol 2 2 ethoxyethoxy ethanol 2 2 methoxyethoxy ethanol 2 2 methoxyethoxy ethanol 2 butoxyethanol 2 chloroethanol 2 ethoxyethanol 2 fluoroethanol 2 mercaptoethanol 2 methoxyethanol aminoethylethanolamine diethylethanolamine dimethylethanolamine ethanol ethanolamine n n diisopropylaminoethanol n methylethanolamine phenoxyethanol tribromoethanol butanol 2 methyl 1 butanol isobutanol n butanol straight chain saturated c 1 c 9 methanol ethanol 1 propanol 1 butanol 1 pentanol 1 hexanol 1 heptanol 1 octanol capryl 1 nonanol pelargonic straight chain saturated c 10 c 19 1 decanol capric 1 undecanol hendecyl 1 dodecanol lauryl 1 tridecanol 1 tetradecanol myristyl 1 pentadecanol 1 hexadecanol cetyl palmityl 1 heptadecanol 1 octadecanol stearyl 1 nonadecanol straight chain saturated c 20 c 29 1 icosanol arachidyl 1 heneicosanol 1 docosanol behenyl 1 tricosanol 1 tetracosanol lignoceryl 1 pentacosanol 1 hexacosanol ceryl 1 heptacosanol 1 octacosanol cluytyl montanyl 1 nonacosanol straight chain saturated c 30 c 39 1 triacontanol melissyl myricyl 1 hentriacontanol 1 dotriacontanol lacceryl 1 tritriacontanol 1 tetratriacontanol geddyl 1 pentatriacontanol 1 hexatriacontanol 1 heptatriacontanol 1 octatriacontanol 1 nonatriacontanol straight chain saturated c 40 c 49 1 tetracontanol 1 hentetracontanol 1 dotetracontanol 1 tritetracontanol 1 tetratetracontanol 1 pentatetracontanol 1 hexatetracontanol 1 heptatetracontanol 1 octatetracontanol 1 nonatetracontanol 2 ethylhexanol allyl alcohol anisyl alcohol benzyl alcohol cinnamyl alcohol crotyl alcohol furfuryl alcohol isoamyl alcohol neopentyl alcohol nicotinyl alcohol perillyl alcohol phenethyl alcohol prenol propargyl alcohol salicyl alcohol tryptophol vanillyl alcohol veratrole alcohol secondary alcohols 2 1 phenylethanol 2 butanol 2 deoxyerythritol 2 heptanol 3 heptanol 2 hexanol 3 hexanol 3 methyl 2 butanol 2 nonanol 2 octanol 2 pentanol 3 pentanol cyclohexanol cyclopentanol cyclopropanol diphenylmethanol isopropanol pinacolyl alcohol pirkle s alcohol propylene glycol methyl ether tertiary alcohols 3 2 methyl 2 pentanol 2 methylheptan 2 ol 2 methylhexan 2 ol 3 methyl 3 pentanol 3 methyloctan 3 ol diacetone alcohol ethchlorvynol methylpentynol nonafluoro tert butyl alcohol tert amyl alcohol tert butyl alcohol triphenylethanol triphenylmethanol hydric alcohols monohydric alcohols methanol c 1 ethanol c 2 isopropanol c 3 1 butanol c 4 1 pentanol c 5 cetyl alcohol c 16 dihydric alcohols ethylene glycol propylene glycol trihydric alcohols glycerol polyhydric alcohols sugar alcohols pentaerythritol ethylene glycol c 2 glycerol propylene glycol c 3 erythritol threitol c 4 xylitol c 5 mannitol sorbitol c 6 volemitol c 7 amyl alcohols 2 2 dimethylpropan 1 ol 2 methylbutan 1 ol 2 methylbutan 2 ol 3 methylbutan 1 ol 3 methylbutan 2 ol pentan 1 ol pentan 2 ol pentan 3 ol aromatic alcohols benzyl alcohol 2 4 dichlorobenzyl alcohol 3 nitrobenzyl alcohol saturated fatty alcohols cetostearyl alcohol decanol lauryl alcohol myristyl alcohol nonanol octanol tridecanol undecanol branched and unsaturated fatty alcohols 3 methyl 3 pentanol erucyl alcohol linolenyl alcohol linoleyl alcohol oleyl alcohol palmitoleyl alcohol tert amyl alcohol tert butyl alcohol sugar alcohols c 1 c 7 methylene glycol c 1 ethylene glycol c 2 glycerol c 3 erythritol c 4 threitol c 4 arabitol c 5 ribitol c 5 xylitol c 5 mannitol c 6 sorbitol c 6 galactitol c 6 iditol c 6 volemitol c 7 deoxy sugar alcohols fucitol cyclic sugar alcohols inositol glycylglycitols maltitol lactitol isomalt maltotriitol maltotetraitol polyglycitol terpene alcohols monoterpene alcohols borneol citronellol geraniol linalool menthol nerol rhodinol terpineol sesquiterpene alcohols bisabolol farnesol nerolidol patchoulol diterpene alcohols phytol dialcohols 1 3 butanediol 1 4 butanediol 1 5 pentanediol 2 methyl 2 propyl 1 3 propanediol diethylpropanediol ethylene glycol trialcohols glycerol sterols cholesterol ergosterol lanosterol β sitosterol stigmasterol fluoroalcohols 1 3 difluoro 2 propanol 2 2 2 trifluoroethanol 2 fluoroethanol nonafluoro tert butyl alcohol trifluoromethanol preparations substitution of haloalkane carbonyl reduction ether cleavage hydrolysis of epoxide hydration of alkene ziegler process reactions deprotonation protonation alcohol oxidation glycol cleavage nucleophilic substitution fischer speier esterification williamson ether synthesis elimination reaction nucleophilic substitution of carbonyl group friedel crafts alkylation nucleophilic conjugate addition transesterification category retrieved from https en wikipedia org w index php title ziegler_process oldid 1220555827 categories fatty alcohols chemical processes this page was last edited on 24 april 2024 at 14 58 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents ziegler process 5 languages add topic