1-Butanol

{{Chembox

|Verifiedfields = changed

|Watchedfields = changed

|verifiedrevid = 411004179

|Name = 1-Butanol

|ImageFileL1 = 1-Butanol skeletal.svg

|ImageFileL1_Ref = {{chemboximage|correct|??}}

|ImageNameL1 = Skeletal formula of n-butanol

|ImageClassL1 = skin-invert-image

|ImageFileR1 = Butan-1-ol-3D-vdW.png

|ImageFileR1_Ref = {{chemboximage|correct|??}}

|ImageNameR1 = Spacefill model of n-butanol

|ImageClassR1 = bg-transparent

|ImageFile2 = Butan-1-ol Lewis.svg

|ImageFile2_Ref = {{chemboximage|correct|??}}

|ImageSize2 = 121

|ImageName2 = Skeletal formula of n-butanol with all explicit hydrogens added

|ImageClass2 = skin-invert-image

|PIN = Butan-1-ol{{Cite web|title = 1-Butanol - Compound Summary|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=263&loc=ec_rcs|work = The PubChem Project|location = USA|publisher = National Center of Biotechnology Information}}

|OtherNames = n-Butanol
n-Butyl alcohol
n-Butyl hydroxide
n-Propylcarbinol
n-Propylmethanol
1-Hydroxybutane
Methylolpropane

|Section1 = {{Chembox Identifiers

|CASNo = 71-36-3

|CASNo_Ref = {{cascite|correct|CAS}}

|PubChem = 263

|ChemSpiderID = 258

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|UNII = 8PJ61P6TS3

|UNII_Ref = {{fdacite|correct|FDA}}

|EINECS = 200-751-6

|UNNumber = 1120

|DrugBank_Ref = {{drugbankcite|changed|drugbank}}

|DrugBank = DB02145

|KEGG = D03200

|KEGG_Ref = {{keggcite|correct|kegg}}

|MeSHName = 1-Butanol

|ChEBI_Ref = {{ebicite|changed|EBI}}

|ChEBI = 28885

|ChEMBL = 14245

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|RTECS = EO1400000

|Beilstein = 969148

|Gmelin = 25753

|3DMet = B00907

|SMILES = OCCCC

|StdInChI = 1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|InChI = 1/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3

|StdInChIKey = LRHPLDYGYMQRHN-UHFFFAOYSA-N

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

}}

|Section2 = {{Chembox Properties

|C=4 | H=10 | O=1

|Appearance = Colourless, refractive liquid

|Odor = banana-like,[n-Butanol Product Information, The Dow Chemical Company, Form No. 327-00014-1001, page 1] harsh, alcoholic and sweet

|Density = 0.81 g/cm³

|MeltingPtC = −89.8

|BoilingPtC = 117.7

|Solubility = 73 g/L at 25 °C

|SolubleOther = very soluble in acetone
miscible with ethanol, ethyl ether

|LogP = 0.839

|RefractIndex = 1.3993 (20 °C)

|Viscosity = 2.573 mPa·s (at 25 °C){{cite journal | last1 = Dubey | first1 = Gyan | year = 2008 | title = 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 | journal = The Journal of Chemical Thermodynamics | volume = 40 | issue = 2 | pages = 309–320 | doi = 10.1016/j.jct.2007.05.016 }}

|Dipole = 1.66 D

|pKa = 16.10

|VaporPressure = 0.58 kPa (20 °C) ILO International Chemical Safety Cards (ICSC)

|MagSus = −56.536·10⁻⁶ cm³/mol

}}

|Section3 = {{Chembox Thermochemistry

|DeltaHf = −328(4) kJ/mol

|DeltaHc = −2670(20) kJ/mol

|Entropy = 225.7 J/(K·mol)

}}

|Section4 = {{Chembox Hazards

|ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics0111.htm ICSC 0111]

|GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}}

|NFPA-H = 1

|NFPA-F = 3

|NFPA-R = 0

|FlashPtC = 35

|AutoignitionPtC = 343

|ExploLimits = 1.45–11.25%

|LD50 = 790 mg/kg (rat, oral)

|PEL = TWA 100 ppm (300 mg/m³){{PGCH|0076}}

|IDLH = 1400 ppm

|REL = C 50 ppm (150 mg/m³) [skin]

|LC50 = 9221 ppm (mammal)
8000 ppm (rat, 4 h){{IDLH|71363|N-butyl alcohol}}

|LDLo = 3484 mg/kg (rabbit, oral)
790 mg/kg (rat, oral)
1700 mg/kg (dog, oral)

}}

|Section5 = {{Chembox Related

|OtherCompounds = Butanethiol
n-Butylamine
Diethyl ether
Pentane

}}

1-Butanol, also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C₄H₉OH 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{{citation | last1 = Hazelwood | first1 = Lucie A. | last2 = Daran | first2 = Jean-Marc | last3 = van Maris | first3 = Antonius J. A. | last4 = Pronk | first4 = Jack T. | last5 = Dickinson | first5 = J. Richard | title = The Ehrlich pathway for fusel alcohol production: a century of research on Saccharomyces cerevisiae metabolism | journal = Appl. Environ. Microbiol. | volume = 74 | issue = 8 | pages = 2259–66 | year = 2008 | pmid = 18281432 | pmc = 2293160 | doi = 10.1128/AEM.02625-07 | bibcode = 2008ApEnM..74.2259H }}. and is present in many foods and drinks.{{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.{{SIDS-ref | name = n-Butanol | id = 71363 | date = 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.{{citation | last1 = Hall | first1 = R. L. | last2 = Oser | first2 = B. L. | year = 1965 | title = Recent progress in the consideration of flavouring ingredients under the food additives amendment. III. Gras substances | journal = Food Technol. | page = 151}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 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.

File:Propen_Hydroformylierung_zu_Butanol.svg

A second method for producing butanol involves the Reppe reaction of propylene with CO and water:{{Ullmann | first1 = Heinz-Dieter | last1 = Hahn | first2 = Georg | last2 = Dämbkes | first3 = Norbert | last3 = Rupprich | title = Butanols|doi = 10.1002/14356007.a04_463|year=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.{{Cite journal |last1=Wang |first1=Shengguang |last2=Vorotnikov |first2=Vassili |last3=G. Vlachos |first3=Dionisios |date=2014 |title=A DFT study of furan hydrogenation and ring opening on Pd(111) |url=https://pubs.rsc.org/en/content/articlehtml/2014/gc/c3gc41183d |journal=Green Chemistry |language=en |volume=16 |issue=2 |pages=736–747 |doi=10.1039/C3GC41183D|doi-access=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.{{cite journal|author=Antoni, D.|author2=Zverlov, V.|author3=Schwarz, W. H.|name-list-style=amp|year=2007|title=Biofuels from Microbes|journal=Applied Microbiology and Biotechnology|volume=77|issue=1|pages=23–35|doi=10.1007/s00253-007-1163-x|pmid=17891391|s2cid=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,{{citation | last = Bonte | first = W. | year = 1979 | title = Congener substances in German and foreign beers | journal = Blutalkohol | volume = 16 | pages = 108–24}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}. grape brandies,{{citation | last1 = Schreier | first1 = Peter | last2 = Drawert | first2 = Friedrich | last3 = Winkler | first3 = Friedrich | year = 1979 | title = Composition of neutral volatile constituents in grape brandies | journal = J. Agric. Food Chem. | volume = 27 | issue = 2 | pages = 365–72| doi = 10.1021/jf60222a031| bibcode = 1979JAFC...27..365S }}. wine,{{citation | last = Bonte | first = W. | year = 1978 | title = Congener content of wine and similar beverages | journal = Blutalkohol | volume = 15 | pages = 392–404}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}. and whisky.{{citation | last1 = Postel | first1 = W. | last2 = Adam | first2 = L. | year = 1978 | title = Gas chromatographic characterization of whiskey. III. Irish whiskey | journal = Branntweinwirtschaft | volume = 118 | pages = 404–7}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}. It has been detected in the volatiles of hops,{{citation | last1 = Tressl | first1 = Roland | last2 = Friese | first2 = Lothar | last3 = Fendesack | first3 = Friedrich | last4 = Koeppler | first4 = Hans | year = 1978 | title = Studies of the volatile composition of hops during storage | journal = J. Agric. Food Chem. | volume = 26 | issue = 6 | pages = 1426–30 | doi = 10.1021/jf60220a036| bibcode = 1978JAFC...26.1426T }}. jack fruit,{{citation | last1 = Swords | first1 = G. | last2 = Bobbio | first2 = P. A. | last3 = Hunter | first3 = G. L. K. | year = 1978 | title = Volatile constituents of jack fruit (Arthocarpus heterophyllus) | journal = J. Food Sci. | volume = 43 | issue = 2 | pages = 639–40 | doi = 10.1111/j.1365-2621.1978.tb02375.x}}. heat-treated milks,{{citation | last1 = Jaddou | first1 = Haytham A. | last2 = Pavey | first2 = John A. | last3 = Manning | first3 = Donald J. | year = 1978 | title = Chemical analysis of flavor volatiles in heat-treated milks | journal = J. Dairy Res. | volume = 45 | issue = 3 | pages = 391–403 | doi = 10.1017/S0022029900016617| s2cid = 85985458 }}. musk melon,{{citation | last1 = Yabumoto | first1 = K. | last2 = Yamaguchi | first2 = M. | last3 = Jennings | first3 = W. G. | year = 1978 | title = Production of volatile compounds by Muskmelon, Cucumis melo | journal = Food Chem. | volume = 3 | issue = 1 | pages = 7–16 | doi = 10.1016/0308-8146(78)90042-0}}. cheese,{{citation | last1 = Dumont | first1 = Jean Pierre | last2 = Adda | first2 = Jacques | year = 1978 | title = Occurrence of sesquiterpones in mountain cheese volatiles | journal = J. Agric. Food Chem. | volume = 26 | issue = 2 | pages = 364–67 | doi = 10.1021/jf60216a037| bibcode = 1978JAFC...26..364D }}. southern pea seed,{{citation | last1 = Fisher | first1 = Gordon S. | last2 = Legendre | first2 = Michael G. | last3 = Lovgren | first3 = Norman V. | last4 = Schuller | first4 = Walter H. | last5 = Wells | first5 = John A. | year = 1979 | title = Volatile constituents of southernpea seed [Vigna unguiculata (L.) Walp.] | journal = J. Agric. Food Chem. | volume = 27 | issue = 1 | pages = 7–11 | doi = 10.1021/jf60221a040| bibcode = 1979JAFC...27....7F }}. and cooked rice.{{citation | last1 = Yajima | first1 = Izumi | last2 = Yanai | first2 = Tetsuya | last3 = Nakamura | first3 = Mikio | last4 = Sakakibara | first4 = Hidemasa | last5 = Habu | first5 = Tsutomu | year = 1978 | title = Volatile flavor components of cooked rice | journal = Agric. Biol. Chem. | volume = 42 | issue = 6 | pages = 1229–33 | url = https://www.jstage.jst.go.jp/article/bbb1961/42/6/42_6_1229/_pdf/-char/en | doi = 10.1271/bbb1961.42.1229 | doi-access = free }}. 1-Butanol is also formed during deep frying of corn oil, cottonseed oil, trilinolein, and triolein.{{citation | last1 = Chang | first1 = S. S. | last2 = Peterson | first2 = K. J. | last3 = Ho | first3 = C. | year = 1978 | title = Chemical reactions involved in the deep-fat frying of foods | journal = J. Am. Oil Chem. Soc. | volume = 55 | issue = 10 | pages = 718–27| doi = 10.1007/BF02665369 | pmid = 730972 | s2cid = 97273264 }}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 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.{{Cite journal |last1=Atsumi |first1=S. |last2=Hanai |first2=T. |last3=Liao |first3=J. C. |year=2008 |title=Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels |journal=Nature |volume=451 |issue=7174 |pages=86–89 |doi=10.1038/nature06450 |pmid=18172501|bibcode=2008Natur.451...86A |s2cid=4413113 }} It is a natural component of many alcoholic beverages, albeit in low and variable concentrations.{{citation |last=Woo |first=Kang-Lyung |title=Determination of low molecular weight alcohols including fusel oil in various samples by diethyl ether extraction and capillary gas chromatography |journal=J. AOAC Int. |year=2005 |volume=88 |issue=5 |pages=1419–27 |doi=10.1093/jaoac/88.5.1419 |pmid=16385992 |doi-access=free}}.{{citation |last1=Lachenmeier |first1=Dirk W. |last2=Haupt |first2=Simone |last3=Schulz |first3=Katja |title=Defining maximum levels of higher alcohols in alcoholic beverages and surrogate alcohol products |journal=Regul. Toxicol. Pharmacol. |year=2008 |volume=50 |issue=3 |pages=313–21 |pmid=18295386 |doi=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.{{citation |last1=Hori |first1=Hisako |last2=Fujii |first2=Wataru |last3=Hatanaka |first3=Yutaka |last4=Suwa |first4=Yoshihide |title=Effects of fusel oil on animal hangover models |journal=Alcohol. Clin. Exp. Res. |year=2003 |volume=27 |issue=8 Suppl |pages=37S–41S |pmid=12960505 |doi=10.1097/01.ALC.0000078828.49740.48|doi-access=free }}.

1-Butanol is used as an ingredient in processed and artificial flavorings,{{citation | last = Mellan | first = I. | year = 1950 | title = Industrial Solvents | location = New York | publisher = Van Nostrand Reinhold | pages = 482–88}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}. and for the extraction of lipid-free protein from egg yolk,{{citation | last1 = Meslar | first1 = Harry W. | last2 = White | first2 = Harold B. III | year = 1978 | title = Preparation of lipid-free protein extracts of egg yolk | journal = Anal. Biochem. | volume = 91 | issue = 1 | pages = 75–81 | doi = 10.1016/0003-2697(78)90817-5 | pmid = 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.{{citation | last1 = Bray | first1 = Walter J. | last2 = Humphries | first2 = Catherine | year = 1978 | title = Solvent fractionation of leaf juice to prepare green and white protein products | journal = J. Sci. Food Agric. | volume = 29 | issue = 10 | pages = 839–46 | doi = 10.1002/jsfa.2740291003| bibcode = 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).{{SIDS-ref|name=Ethanol|id=64175|date=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.{{citation |last1=Gaillard |first1=D. |last2=Derache |first2=R. |year=1965 |title=Métabilisation de différents alcools présents dans les biossons alcooliques chez le rat |journal=Trav. Soc. Pharmacol. Montpellier |volume=25 |pages=541–62}}, cited in {{EHC-ref |id=65 |name=Butanols: four isomers |date=1987 |isbn=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.{{citation |last1=McCreery |first1=N. J. |last2=Hunt |first2=W. A. |year=1978 |title=Physico-chemical correlates of alcohol intoxication |journal=Neuropharmacology |volume=17 |issue=7 |pages=451–61 |doi=10.1016/0028-3908(78)90050-3 |pmid=567755|s2cid=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).{{citation |last1=Wysocki |first1=C. J. |last2=Dalton |first2=P. |year=1996 |title=Odor and Irritation Thresholds for 1-Butanol in Humans |publisher=Monell Chemical Senses Center |location=Philadelphia}}, cited in {{SIDS-ref |name=n-Butanol |id=71363 |date=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.{{citation |last1=Cometto-Muñiz |first1=J. Enrique |last2=Cain |first2=William S. |year=1998 |title=Trigeminal and Olfactory Sensitivity: Comparison of Modalities and Methods of Measurement |journal=Int. Arch. Occup. Environ. Health |volume=71 |issue=2 |pages=105–10 |doi=10.1007/s004200050256 |pmid=9580447 |bibcode=1998IAOEH..71..105C |s2cid=25246408 |url=http://www.escholarship.org/uc/item/52f8x48p }}.