1-Butanol

Chemical compound (C4H9OH) changed changed 411004179 1-Butanol 1-Butanol skeletal.svg correct ?? Skeletal formula of n-butanol skin-invert-image Butan-1-ol-3D-vdW.png correct ?? Spacefill model of n-butanol bg-transparent Butan-1-ol Lewis.svg correct ?? 121 Skeletal formula of n-butanol with all explicit hydrogens added skin-invert-image Butan-1-ol 1-Butanol - Compound Summary https://pubchem.ncbi.nlm.nih.gov/compound/263 The PubChem Project USA National Center of Biotechnology Information n-Butanoln-Butyl alcoholn-Butyl hydroxiden-Propylcarbinoln-Propylmethanol1-HydroxybutaneMethylolpropane 71-36-3 correct CAS BuOHn-BuOHnBuOHnBuOH 263 258 correct chemspider 8PJ61P6TS3 correct FDA 200-751-6 1120 changed drugbank DB02145 D03200 correct kegg 1-Butanol changed EBI 28885 14245 correct EBI EO1400000 969148 25753 B00907 OCCCC 1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3 correct chemspider 1/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3 LRHPLDYGYMQRHN-UHFFFAOYSA-N correct chemspider 4 10 1 Colourless, refractive liquid banana-like,[n-Butanol Product Information, The Dow Chemical Company, Form No. 327-00014-1001, page 1] harsh, alcoholic and sweet 0.81 g/cm3 −89.8 117.7 73 g/L at 25 °C very soluble in acetone miscible with ethanol, ethyl ether 0.839 1.3993 (20 °C) 2.573 mPa·s (at 25 °C) Dubey Gyan 2008 Study of densities, viscosities, and speeds of sound of binary liquid mixtures of butan-1-ol with n-alkanes (C6, C8, and C10) at T = (298.15, 303.15, and 308.15) K The Journal of Chemical Thermodynamics 40 2 309–320 10.1016/j.jct.2007.05.016 1.66 D 16.10 0.58 kPa (20 °C) ILO International Chemical Safety Cards (ICSC) −56.536·10−6 cm3/mol −328(4) kJ/mol −2670(20) kJ/mol 225.7 J/(K·mol) ICSC 0111 02 05 07 226 302 315 318 335 336 210 233 240 241 242 243 261 264 264+265 270 271 280 301+317 302+352 303+361+353 304+340 305+354+338 317 319 321 330 332+317 362+364 370+378 403+233 403+235 405 501 1 3 0 35 343 1.45–11.25% 790 mg/kg (rat, oral) TWA 100 ppm (300 mg/m3)0076 1400 ppm C 50 ppm (150 mg/m3) [skin] 9221 ppm (mammal)8000 ppm (rat, 4 h)71363 N-butyl alcohol 3484 mg/kg (rabbit, oral)790 mg/kg (rat, oral)1700 mg/kg (dog, oral) Butanethioln-ButylamineDiethyl etherPentane 1-Butanol, also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C4H10O 1, C4H9OH or CH3(CH2)3OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and tert-butanol. The unmodified term butanol usually refers to the straight chain isomer. 1-Butanol occurs naturally as a minor product of the ethanol fermentation of sugars and other saccharides Hazelwood Lucie A. Daran Jean-Marc van Maris Antonius J. A. Pronk Jack T. Dickinson J. Richard The Ehrlich pathway for fusel alcohol production: a century of research on Saccharomyces cerevisiae metabolism Appl. Environ. Microbiol. 74 8 2259–66 2008 18281432 2293160 10.1128/AEM.02625-07 2008ApEnM..74.2259H . and is present in many foods and drinks. 65 Butanols: four isomers 1987 92-4-154265-9. n-Butanol 71363 April 2005. It is also a permitted artificial flavorant in the United States,21 C.F.R. § 172.515; 42 FR 14491, Mar. 15, 1977, as amended. used in butter, cream, fruit, rum, whiskey, ice cream and ices, candy, baked goods, and cordials. Hall R. L. Oser B. L. 1965 Recent progress in the consideration of flavouring ingredients under the food additives amendment. III. Gras substances Food Technol. 151, cited in 65 Butanols: four isomers 1987 92-4-154265-9. It is also used in a wide range of consumer products. The largest use of 1-butanol is as an industrial intermediate, particularly for the manufacture of butyl acetate (itself an artificial flavorant and industrial solvent). It is a petrochemical derived from propylene. Estimated production figures for 1997 are: United States 784,000 tonnes; Western Europe 575,000 tonnes; Japan 225,000 tonnes. Production Since the 1950s, most 1-butanol is produced by the hydroformylation of propene (oxo process) to preferentially form the butyraldehyde n-butanal. Typical catalysts are based on cobalt and rhodium. Butyraldehyde is then hydrogenated to produce butanol. class=skin-invert-image|center A second method for producing butanol involves the Reppe reaction of propylene with CO and water: Heinz-Dieter Hahn Georg Dämbkes Norbert Rupprich Butanols 10.1002/14356007.a04_463 2005. CH3CH=CH2 + H2O + 2 CO → CH3CH2CH2CH2OH + CO2 In former times, butanol was prepared from crotonaldehyde, which can be obtained from acetaldehyde. Butanol can also be produced by fermentation of biomass by bacteria. Prior to the 1950s, Clostridium acetobutylicum was used in industrial fermentation to produce butanol. Research in the past few decades showed results of other microorganisms that can produce butanol through fermentation. Butanol can be produced via furan hydrogenation over Pd or Pt catalyst at high temperature and high pressure.Wang Shengguang Vorotnikov Vassili G. Vlachos Dionisios 2014 A DFT study of furan hydrogenation and ring opening on Pd(111) Green Chemistry en 16 2 736–747 10.1039/C3GC41183D free Industrial use Constituting 85% of its use, 1-butanol is mainly used in the production of varnishes. It is a popular solvent, e.g. for nitrocellulose. A variety of butanol derivatives are used as solvents, e.g. butoxyethanol or butyl acetate. Many plasticizers are based on butyl esters, e.g., dibutyl phthalate. The monomer butyl acrylate is used to produce polymers. It is the precursor to n-butylamines. Biofuel 1-Butanol has been proposed as a substitute for diesel fuel and gasoline. It is produced in small quantities in nearly all fermentations (see fusel oil). Clostridium produces much higher yields of butanol. Research is underway to increase the biobutanol yield from biomass. Butanol is considered as a potential biofuel (butanol fuel). Butanol at 85 percent strength can be used in cars designed for gasoline without any change to the engine (unlike 85% ethanol), and it provides more energy for a given volume than ethanol, almost as much as gasoline. Therefore, 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.Antoni, D. Zverlov, V. Schwarz, W. H. amp 2007 Biofuels from Microbes Applied Microbiology and Biotechnology 77 1 23–35 10.1007/s00253-007-1163-x 17891391 35454212 The production of, or in some cases, the use of, the following substances may result in exposure to 1-butanol: artificial leather, butyl esters, rubber cement, dyes, fruit essences, lacquers, motion picture, and photographic films, raincoats, perfumes, pyroxylin plastics, rayon, safety glass, shellac varnish, and waterproofed cloth. Occurrence in nature Butan-1-ol occurs naturally as a result of carbohydrate fermentation in a number of alcoholic beverages, including beer, Bonte W. 1979 Congener substances in German and foreign beers Blutalkohol 16 108–24, cited in 65 Butanols: four isomers 1987 92-4-154265-9. grape brandies, Schreier Peter Drawert Friedrich Winkler Friedrich 1979 Composition of neutral volatile constituents in grape brandies J. Agric. Food Chem. 27 2 365–72 10.1021/jf60222a031 1979JAFC...27..365S . wine, Bonte W. 1978 Congener content of wine and similar beverages Blutalkohol 15 392–404, cited in 65 Butanols: four isomers 1987 92-4-154265-9. and whisky. Postel W. Adam L. 1978 Gas chromatographic characterization of whiskey. III. Irish whiskey Branntweinwirtschaft 118 404–7, cited in 65 Butanols: four isomers 1987 92-4-154265-9. It has been detected in the volatiles of hops, Tressl Roland Friese Lothar Fendesack Friedrich Koeppler Hans 1978 Studies of the volatile composition of hops during storage J. Agric. Food Chem. 26 6 1426–30 10.1021/jf60220a036 1978JAFC...26.1426T . jack fruit, Swords G. Bobbio P. A. Hunter G. L. K. 1978 Volatile constituents of jack fruit (Arthocarpus heterophyllus) J. Food Sci. 43 2 639–40 10.1111/j.1365-2621.1978.tb02375.x. heat-treated milks, Jaddou Haytham A. Pavey John A. Manning Donald J. 1978 Chemical analysis of flavor volatiles in heat-treated milks J. Dairy Res. 45 3 391–403 10.1017/S0022029900016617 85985458 . musk melon, Yabumoto K. Yamaguchi M. Jennings W. G. 1978 Production of volatile compounds by Muskmelon, Cucumis melo Food Chem. 3 1 7–16 10.1016/0308-8146(78)90042-0. cheese, Dumont Jean Pierre Adda Jacques 1978 Occurrence of sesquiterpones in mountain cheese volatiles J. Agric. Food Chem. 26 2 364–67 10.1021/jf60216a037 1978JAFC...26..364D . southern pea seed, Fisher Gordon S. Legendre Michael G. Lovgren Norman V. Schuller Walter H. Wells John A. 1979 Volatile constituents of southernpea seed [Vigna unguiculata (L.) Walp.] J. Agric. Food Chem. 27 1 7–11 10.1021/jf60221a040 1979JAFC...27....7F . and cooked rice. Yajima Izumi Yanai Tetsuya Nakamura Mikio Sakakibara Hidemasa Habu Tsutomu 1978 Volatile flavor components of cooked rice Agric. Biol. Chem. 42 6 1229–33 https://www.jstage.jst.go.jp/article/bbb1961/42/6/42_6_1229/_pdf/-char/en 10.1271/bbb1961.42.1229 free . 1-Butanol is also formed during deep frying of corn oil, cottonseed oil, trilinolein, and triolein. Chang S. S. Peterson K. J. Ho C. 1978 Chemical reactions involved in the deep-fat frying of foods J. Am. Oil Chem. Soc. 55 10 718–27 10.1007/BF02665369 730972 97273264 , cited in 65 Butanols: four isomers 1987 92-4-154265-9. Butan-1-ol is one of the "fusel alcohols" (from the German for "bad liquor"), which include alcohols that have more than two carbon atoms and have significant solubility in water.Atsumi S. Hanai T. Liao J. C. 2008 Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels Nature 451 7174 86–89 10.1038/nature06450 18172501 2008Natur.451...86A 4413113 It is a natural component of many alcoholic beverages, albeit in low and variable concentrations.Woo Kang-Lyung Determination of low molecular weight alcohols including fusel oil in various samples by diethyl ether extraction and capillary gas chromatography J. AOAC Int. 2005 88 5 1419–27 10.1093/jaoac/88.5.1419 16385992 free.Lachenmeier Dirk W. Haupt Simone Schulz Katja Defining maximum levels of higher alcohols in alcoholic beverages and surrogate alcohol products Regul. Toxicol. Pharmacol. 2008 50 3 313–21 18295386 10.1016/j.yrtph.2007.12.008. It (along with similar fusel alcohols) is reputed to be responsible for severe hangovers, although experiments in animal models show no evidence for this.Hori Hisako Fujii Wataru Hatanaka Yutaka Suwa Yoshihide Effects of fusel oil on animal hangover models Alcohol. Clin. Exp. Res. 2003 27 8 Suppl 37S–41S 12960505 10.1097/01.ALC.0000078828.49740.48 free . 1-Butanol is used as an ingredient in processed and artificial flavorings, Mellan I. 1950 Industrial Solvents New York Van Nostrand Reinhold 482–88, cited in 65 Butanols: four isomers 1987 92-4-154265-9. and for the extraction of lipid-free protein from egg yolk, Meslar Harry W. White Harold B. III 1978 Preparation of lipid-free protein extracts of egg yolk Anal. Biochem. 91 1 75–81 10.1016/0003-2697(78)90817-5 9762085. natural flavouring materials and vegetable oils, the manufacture of hop extract for beermaking, and as a solvent in removing pigments from moist curd leaf protein concentrate. Bray Walter J. Humphries Catherine 1978 Solvent fractionation of leaf juice to prepare green and white protein products J. Sci. Food Agric. 29 10 839–46 10.1002/jsfa.2740291003 1978JSFA...29..839B . Metabolism and toxicity The acute toxicity of 1-butanol is relatively low, with oral LD50 values of 790–4,360 mg/kg (rat; comparable values for ethanol are 7,000–15,000 mg/kg).Ethanol 64175 August 2005. It is metabolized completely in vertebrates in a manner similar to ethanol: alcohol dehydrogenase converts 1-butanol to butyraldehyde; this is then converted to butyric acid by aldehyde dehydrogenase. Butyric acid can be fully metabolized to carbon dioxide and water by the β-oxidation pathway. In the rat, only 0.03% of an oral dose of 2,000 mg/kg was excreted in the urine.Gaillard D. Derache R. 1965 Métabilisation de différents alcools présents dans les biossons alcooliques chez le rat Trav. Soc. Pharmacol. Montpellier 25 541–62, cited in 65 Butanols: four isomers 1987 92-4-154265-9. At sub-lethal doses, 1-butanol acts as a depressant of the central nervous system, similar to ethanol: one study in rats indicated that the intoxicating potency of 1-butanol is about 6 times higher than that of ethanol, possibly because of its slower transformation by alcohol dehydrogenase.McCreery N. J. Hunt W. A. 1978 Physico-chemical correlates of alcohol intoxication Neuropharmacology 17 7 451–61 10.1016/0028-3908(78)90050-3 567755 19914287 . Other hazards Liquid 1-butanol, as is common with most organic solvents, is extremely irritating to the eyes; repeated contact with the skin can also cause irritation. This is believed to be a generic effect of defatting. No skin sensitization has been observed. Irritation of the respiratory pathways occurs only at very high concentrations (>2,400 ppm).Wysocki C. J. Dalton P. 1996 Odor and Irritation Thresholds for 1-Butanol in Humans Monell Chemical Senses Center Philadelphia, cited in n-Butanol 71363 April 2005. With a flash point of 35 °C, 1-butanol presents a moderate fire hazard: it is slightly more flammable than kerosene or diesel fuel but less flammable than many other common organic solvents. The depressant effect on the central nervous system (similar to ethanol intoxication) is a potential hazard when working with 1-butanol in enclosed spaces, although the odour threshold (0.2–30 ppm) is far below the concentration which would have any neurological effect.Cometto-Muñiz J. Enrique Cain William S. 1998 Trigeminal and Olfactory Sensitivity: Comparison of Modalities and Methods of Measurement Int. Arch. Occup. Environ. Health 71 2 105–10 10.1007/s004200050256 9580447 1998IAOEH..71..105C 25246408 http://www.escholarship.org/uc/item/52f8x48p . See also Butanol fuel External links 0111 01 0076 n-Butanol 71363 April 2005 65 Butanols: four isomers 003 3 1-Butanol 1987 0259-7268 References Category:Alcohol solvents Category:Primary alcohols Category:GABAA receptor positive allosteric modulators Category:Sedatives Category:Hypnotics Category:Alkanols Category:Butyl compounds