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butanol 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 isomers 2 toxicity 3 uses toggle uses subsection 3 1 primary uses 4 recreational use 5 biobutanol 6 production 7 see also 8 references toggle the table of contents butanol 43 languages العربية বাংলা bosanski català کوردی čeština deutsch esperanto español eesti euskara فارسی suomi français galego עברית magyar bahasa indonesia italiano 日本語 қазақша 한국어 latina latviešu nederlands norsk nynorsk norsk bokmål português română русский simple english slovenščina shqip svenska kiswahili தமிழ் తెలుగు türkçe українська oʻzbekcha ўзбекча winaray 粵語 中文 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 wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical compound family c4h9oh butanol also called butyl alcohol is a four carbon alcohol with a formula of c 4 h 9 oh which occurs in five isomeric structures four structural isomers from a straight chain primary alcohol to a branched chain tertiary alcohol 1 all are a butyl or isobutyl group linked to a hydroxyl group sometimes represented as buoh sec buoh i buoh and t buoh these are 1 butanol two stereoisomers of sec butyl alcohol isobutanol and tert butyl alcohol butanol is primarily used as a solvent and as an intermediate in chemical synthesis and may be used as a fuel biologically produced butanol is called biobutanol which may be n butanol or isobutanol isomers edit the unmodified term butanol usually refers to the straight chain isomer with the alcohol functional group at the terminal carbon which is also known as 1 butanol the straight chain isomer with the alcohol at an internal carbon is sec butyl alcohol or 2 butanol the branched isomer with the alcohol at a terminal carbon is isobutanol or 2 methyl 1 propanol and the branched isomer with the alcohol at the internal carbon is tert butyl alcohol or 2 methyl 2 propanol 1 butanol n butanol 2 butanol sec butyl alcohol isobutanol 2 methylpropan 1 ol tert butyl alcohol 2 methylpropan 2 ol the butanol isomers have different melting and boiling points 1 butanol and isobutanol have limited solubility sec butyl alcohol has substantially greater solubility whereas tert butyl alcohol is miscible with water the hydroxyl group makes the molecule polar promoting solubility in water while the longer hydrocarbon chain mitigates the polarity and reduces solubility toxicity edit butanol exhibits a low order of toxicity in single dose experiments with laboratory animals 2 3 and is considered safe enough for use in cosmetics brief repeated overexposure with the skin can result in depression of the central nervous system as with other short chain alcohols exposure may also cause severe eye irritation and moderate skin irritation the main dangers are from prolonged exposure to the alcohol s vapors in extreme cases this includes suppression of the central nervous system and even death under most circumstances butanol is quickly metabolized to carbon dioxide it has not been shown to damage dna or cause cancer uses edit primary uses edit butanol is used as a solvent for a wide variety of chemical and textile processes in organic synthesis and as a chemical intermediate it is also used as a paint thinner and a solvent in other coating applications where a relatively slow evaporating latent solvent is preferable as with lacquers and ambient cured enamels it is also used as a component of hydraulic and brake fluids 4 a 50 solution of butanol in water has been used since the 20th century to retard the drying of fresh plaster in fresco painting the solution is usually sprayed on the wet plaster after the plaster has been trowelled smooth and extends the working period during which frescos can be painted up to 18 hours 5 butanol is used in the synthesis of 2 butoxyethanol a major application for butanol is as a reactant with acrylic acid to produce butyl acrylate a primary ingredient of water based acrylic paint 6 it is also used as a base for perfumes but on its own has a highly alcoholic aroma salts of butanol are chemical intermediates for example alkali metal salts of tert butanol are tert butoxides recreational use edit 2 methyl 2 butanol is a central nervous system depressant with a similar effect upon ingestion to ethanol case reports have been documented demonstrating its potential for abuse 7 biobutanol edit main article butanol fuel butanol n butanol or isobutanol is a potential biofuel butanol fuel 8 butanol at 85 percent concentration can be used in cars designed for gasoline petrol without any change to the engine unlike 85 ethanol and it contains more energy for a given volume than ethanol and almost as much as gasoline and a vehicle using butanol would return fuel consumption more comparable to gasoline than ethanol butanol can also be added to diesel fuel to reduce soot emissions 9 photoautotrophic microorganisms like cyanobacteria can be engineered to produce 1 butanol indirectly from co 2 and water 10 production edit main article butanol fuel butanols are normally present in fusel alcohol since the 1950s most butanol in the united states is produced commercially from fossil fuels the most common process starts with propene propylene which is put through a hydroformylation reaction to form butanal which is then reduced with hydrogen to 1 butanol and or 2 butanol tert butanol is derived from isobutane as a co product of propylene oxide production butanol can also be produced by fermentation of biomass by bacteria prior to the 1950s clostridium acetobutylicum was used in industrial fermentation to produce n butanol see also edit a b e process algal fuel references edit merck index 12th edition 1575 atsumi s hanai t liao j c 2008 non fermentative pathways for synthesis of branched chain higher alcohols as biofuels nature 451 7174 86 9 doi 10 1038 nature06450 pmid 18172501 s2cid 4413113 16 ecetoc jacc no 41 n butanol cas no 71 36 3 european centre for ecotoxicology and toxicology of chemicals brussels december 2003 pages 3 4 n butanol archived from the original on 2015 04 02 retrieved 2012 02 03 isobutanol chemicalland21 com archived from the original on january 18 2006 diego s assistants diego rivera mural project www riveramural org retrieved 2019 03 27 harris o et al august 1998 toxicological profile for 2 butoxyethanol and 2 butoxyethanol acetate u s dept of health and human services syed alia n leo raphael j 2022 recreational 2 methyl 2 butanol use the primary care companion for cns disorders 24 6 doi 10 4088 pcc 22cr03292 s2cid 253700629 sampa maiti et al dec 10 2015 quest for sustainable bio production and recovery of butanol as a promising solution to fossil fuel energy research 40 4 411 438 doi 10 1002 er 3458 antoni d zverlov v schwarz w h 2007 biofuels from microbes applied microbiology and biotechnology 77 1 23 35 doi 10 1007 s00253 007 1163 x pmid 17891391 s2cid 35454212 liu x miao r lindberg p lindblad p 2019 modular engineering for efficient photosynthetic biosynthesis of 1 butanol from co 2 in cyanobacteria energy environmental science 12 9 2765 2777 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 authority control databases international gnd national united states france bnf data czech republic latvia israel other yale lux retrieved from https en wikipedia org w index php title butanol oldid 1371754334 categories alkanols alcohol solvents fatty alcohols biotechnology products liquid fuels oxygenates hidden categories articles with short description short description is different from wikidata cs1 unfit url this page was last edited on 28 august 2026 at 07 07 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 butanol 43 languages add topic
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