''n''-Butanol

n-Butanol
Names
Systematic IUPAC name
Butan-1-ol[1]
Other names
Butalcohol

Butanol
1-Butanol
Butyl alcohol
Butyl hydrate
Butylic alcohol
Butyralcohol
Butyric alcohol
Butyryl alcohol
n-Butyl alcohol
1-Hydroxybutane

n-Propylcarbinol
Identifiers
3D model (JSmol)
3DMet B00907
969148
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.000.683
EC Number 200-751-6
25753
KEGG
MeSH 1-Butanol
RTECS number EO1400000
UNII
UN number 1120
Properties
C4H10O
Molar mass 74.12 g·mol−1
Appearance Colourless, refractive liquid
Odor banana-like,[2] harsh, alcoholic and sweet
Density 0.81 g cm−3
Melting point −89.8 °C (−129.6 °F; 183.3 K)
Boiling point 117.7 °C (243.9 °F; 390.8 K)
73 g L−1 at 25 °C
Solubility very soluble in acetone
miscible with ethanol, ethyl ether
log P 0.839
Vapor pressure 6 mmHg (20 °C)[3]
Acidity (pKa) 16.10
-56.536·10−6 cm3/mol
1.3993 (20 °C)
Viscosity 2.573 mPa×s (at 25 °C) [4]
1.66 D
Thermochemistry
225.7 J K−1 mol−1
−328(4) kJ mol−1
−2670(20) kJ mol−1
Hazards
Safety data sheet ICSC 0111
Xn
R-phrases (outdated) R10, R22, R37/38, R41, R67
S-phrases (outdated) (S2), S7/9, S13, S26, S37/39, S46
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
3
1
0
Flash point 35 °C (95 °F; 308 K)
343 °C (649 °F; 616 K)
Explosive limits 1.45–11.25%
Lethal dose or concentration (LD, LC):
790 mg/kg (rat, oral)
3484 mg/kg (rabbit, oral)
790 mg/kg (rat, oral)
1700 mg/kg (dog, oral)[5]
9221 ppm (mammal)
8000 ppm (rat, 4 hr)[5]
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 100 ppm (300 mg/m3)[3]
REL (Recommended)
 C 50 ppm (150 mg/m3) [skin][3]
IDLH (Immediate danger)
 1400 ppm[3]
Related compounds
Related compounds
 Butanethiol
n-Butylamine
Pentane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

n-Butanol or n-butyl alcohol or normal butanol is a primary alcohol with a 4-carbon structure and the chemical formula C4H9OH. Its isomers include isobutanol, 2-butanol, and tert-butanol. Butanol is one of the group of "fusel alcohols" (from the German for "bad liquor"), which have more than two carbon atoms and have significant solubility in water.

n-Butanol occurs naturally as a minor product of the fermentation of sugars and other carbohydrates,[6] and is present in many foods and beverages.[7][8] It is also a permitted artificial flavorant in the United States,[9] used in butter, cream, fruit, rum, whiskey, ice cream and ices, candy, baked goods and cordials.[10] It is also used in a wide range of consumer products.[7]

The largest use of n-butanol is as an industrial intermediate, particularly for the manufacture of butyl acetate (itself an artificial flavorant and industrial solvent). It is a petrochemical, manufactured from propylene and usually used close to the point of manufacture. Estimated production figures for 1997 are: United States 784,000 tonnes; Western Europe 575,000 tonnes; Japan 225,000 tonnes.[8]

Production

n-Butanol is produced industrially from the petrochemical feedstock propylene. Propylene is hydroformylated to butyraldehyde (oxo process) in the presence of a rhodium-based homogeneous catalyst similar to Wilkinson's catalyst. The butyraldehyde is then hydrogenated to produce n-butanol.[8]

Industrial use

n-butanol is an intermediate in the production of butyl acrylate, butyl acetate, dibutyl phthalate, dibutyl sebacate, and other butyl esters,[11][12] butyl ethers such as ethylene glycol monobutyl ether, di- and triethylene glycol monobutyl ether, and the corresponding butyl ether acetates. Other industrial uses include the manufacture of pharmaceuticals, polymers, pyroxylin plastics, herbicide esters, printing (e.g., 2,4-D, 2,4,5-T)[13] and butyl xanthate. It is also used as a diluent/reactant in the manufacture of urea–formaldehyde and melamine–formaldehyde resins.[8]

Other uses

n-Butanol is used as an ingredient in perfumes and as a solvent for the extraction of essential oils.[11] n-Butanol is also used as an extractant in the manufacture of antibiotics, hormones, and vitamins;[11][12] a solvent for paints, coatings, natural resins, gums, synthetic resins, dyes, alkaloids, and camphor.[11][12] Other miscellaneous applications of n-butanol are as a swelling agent in textiles, as a component of hydraulic brake fluids, cleaning formulations, degreasers, and repellents;[7] and as a component of ore floation agents,[13] and of wood-treating systems.[14]

n-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), but species of Clostridium produce much higher yields of butanol, and research is currently underway to increase the ultimate yield of biobutanol from biomass.

The production or, in some cases, use of the following substances may result in exposure to n-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.[7]

Occurrence in nature

Honey bees use n-butanol as an Alarm pheromone.

Occurrence in food

n-Butanol occurs naturally as a result of carbohydrate fermentation in a number of alcoholic beverages, including beer,[15] grape brandies,[16] wine,[17] and whisky.[18] It has been detected in the volatiles of hops,[19] jack fruit,[20] heat-treated milks,[21] musk melon,[22] cheese,[23] southern pea seed,[24] and cooked rice.[25] n-Butanol is also formed during deep frying of corn oil, cottonseed oil, trilinolein, and triolein.[26]

n-Butanol is used as an ingredient in processed and artificial flavourings,[11] and for the extraction of lipid-free protein from egg yolk,[27] 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.[28]

Metabolism and toxicity

n-Butanol is readily absorbed through the intestinal tract and lungs, and also to some extent through the skin.[29] It is metabolized completely in vertebrates in a manner similar to ethanol: alcohol dehydrogenase converts n-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.[30]

The acute toxicity of n-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).[8][31] No deaths were reported at an inhaled concentration of 8,000 ppm (4-hour exposure, rats). At sub-lethal doses, n-butanol acts as a depressant of the central nervous system, similar to ethanol: one study in rats indicated that the intoxicating potency of n-butanol is some six times higher than that of ethanol, possibly because of its slower transformation by alcohol dehydrogenase.[32]

n-Butanol is a natural component of many alcoholic beverages, albeit in low (but variable) concentrations.[33][34] It (along with similar fusel alcohols) is reputed to be responsible for severe "hangovers", although experiments in animal models show no evidence for this.[35] An unknown dose n-Butanol was consumed by a 47-year-old male with no previous medical history, leading to a range of adverse health effects.[36]

Other hazards

Liquid n-butanol, as is common with most organic solvents, is extremely irritating to the eyes; repeated contact with the skin can also cause irritation.[8] 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).[37]

With a flash point of 35 °C, n-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 n-butanol in enclosed spaces, although the odour threshold (0.2–30 ppm) is far below the concentration which would have any neurological effect.[37][38]

n-Butanol is of low toxicity to aquatic vertebrates and invertebrates. It is rapidly biodegraded in water, although an estimated 83% partitions to air where it is degraded by hydroxyl radicals with a half-life of 1.2–2.3 days. It has low potential to bioaccumulate.[8] A potential hazard of significant discharges to watercourses is the rise in chemical oxygen demand (C.O.D.) associated with its biodegradation.

See also

References

  1. ↑ "1-Butanol - Compound Summary". The PubChem Project. USA: National Center of Biotechnology Information.
  2. ↑ [n-Butanol Product Information, The Dow Chemical Company, Form No. 327-00014-1001, page 1]
  3. 1 2 3 4 "NIOSH Pocket Guide to Chemical Hazards #0076". National Institute for Occupational Safety and Health (NIOSH).
  4. ↑ 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. doi:10.1016/j.jct.2007.05.016.
  5. 1 2 "N-butyl alcohol". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
  6. ↑ Hazelwood, Lucie A.; Daran, Jean-Marc; van Maris, Antonius J. A.; Pronk, Jack T.; Dickinson, J. Richard (2008), "The Ehrlich pathway for fusel alcohol production: a century of research on Saccharomyces cerevisiae metabolism", Appl. Environ. Microbiol., 74 (8): 2259–66, PMC 2293160 Freely accessible, PMID 18281432, doi:10.1128/AEM.02625-07.
  7. 1 2 3 4 Butanols: four isomers, Environmental Health Criteria monograph No. 65, Geneva: World Health Organization, 1987, ISBN 92-4-154265-9.
  8. 1 2 3 4 5 6 7 n-Butanol (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, April 2005.
  9. ↑ 21 C.F.R. § 172.515; 42 FR 14491, Mar. 15, 1977, as amended.
  10. ↑ 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 Butanols: four isomers, Environmental Health Criteria monograph No. 65, Geneva: World Health Organization, 1987, ISBN 92-4-154265-9.
  11. 1 2 3 4 5 Mellan, I. (1950), Industrial Solvents, New York: Van Nostrand Reinhold, pp. 482–88, cited in Butanols: four isomers, Environmental Health Criteria monograph No. 65, Geneva: World Health Organization, 1987, ISBN 92-4-154265-9.
  12. 1 2 3 Doolittle, A. K. (1954), The Technology of Solvents and Plasticizers, New York: Wiley, pp. 644–45, cited in Butanols: four isomers, Environmental Health Criteria monograph No. 65, Geneva: World Health Organization, 1987, ISBN 92-4-154265-9.
  13. 1 2 Monich, J. A. (1968), Alcohols: Their Chemistry, Properties, and Manufacture, New York: Chapman and Reinhold, cited in Butanols: four isomers, Environmental Health Criteria monograph No. 65, Geneva: World Health Organization, 1987, ISBN 92-4-154265-9.
  14. ↑ ZA 7801031, Amundsen, J.; R. J. Goodwin & W. H. Wetzel, "Water-soluble pentachlorophenol and tetrachlorophenol wood-treating systems", published 28 Feb. 1979.
  15. ↑ Bonte, W. (1979), "Congener substances in German and foreign beers", Blutalkohol, 16: 108–24, cited in Butanols: four isomers, Environmental Health Criteria monograph No. 65, Geneva: World Health Organization, 1987, ISBN 92-4-154265-9.
  16. ↑ Schreier, Peter; Drawert, Friedrich; Winkler, Friedrich (1979), "Composition of neutral volatile constituents in grape brandies", J. Agric. Food Chem., 27 (2): 365–72, doi:10.1021/jf60222a031.
  17. ↑ Bonte, W. (1978), "Congener content of wine and similar beverages", Blutalkohol, 15: 392–404, cited in Butanols: four isomers, Environmental Health Criteria monograph No. 65, Geneva: World Health Organization, 1987, ISBN 92-4-154265-9.
  18. ↑ Postel, W.; Adam, L. (1978), "Gas chromatographic characterization of whiskey. III. Irish whiskey", Branntweinwirtschaft, 118: 404–7, cited in Butanols: four isomers, Environmental Health Criteria monograph No. 65, Geneva: World Health Organization, 1987, ISBN 92-4-154265-9.
  19. ↑ 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, doi:10.1021/jf60220a036.
  20. ↑ Swords, G.; Bobbio, P. A.; Hunter, G. L. K. (1978), "Volatile constituents of jack fruit (Arthocarpus heterophyllus)", J. Food Sci., 43 (2): 639–40, doi:10.1111/j.1365-2621.1978.tb02375.x.
  21. ↑ 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, doi:10.1017/S0022029900016617.
  22. ↑ Yabumoto, K.; Yamaguchi, M.; Jennings, W. G. (1978), "Production of volatile compounds by Muskmelon, Cucumis melo", Food Chem., 3 (1): 7–16, doi:10.1016/0308-8146(78)90042-0.
  23. ↑ Dumont, Jean Pierre; Adda, Jacques (1978), "Occurrence of sesquiterpones in mountain cheese volatiles", J. Agric. Food Chem., 26 (2): 364–67, doi:10.1021/jf60216a037.
  24. ↑ 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, doi:10.1021/jf60221a040.
  25. ↑ Yajima, Izumi; Yanai, Tetsuya; Nakamura, Mikio; Sakakibara, Hidemasa; Habu, Tsutomu (1978), "Volatile flavor components of cooked rice", Agric. Biol. Chem., 42 (6): 1229–33, doi:10.1271/bbb1961.42.1229.
  26. ↑ Chang, S. S.; Peterson, K. J.; Ho, C. (1978), "Chemical reactions involved in the deep-fat frying of foods", J. Am. Oil Chem. Soc.: 718–27, cited in Butanols: four isomers, Environmental Health Criteria monograph No. 65, Geneva: World Health Organization, 1987, ISBN 92-4-154265-9.
  27. ↑ Meslar, Harry W.; White, Harold B., III (1978), "Preparation of lipid-free protein extracts of egg yolk", Anal. Biochem., 91 (1): 75–81, PMID 9762085, doi:10.1016/0003-2697(78)90817-5.
  28. ↑ 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, doi:10.1002/jsfa.2740291003.
  29. ↑ Theorell, Hugo; Bonnichsen, Roger; Holtermann, Hugo; Sörensen, JöRgine Stene; Sörensen, Nils Andreas (1951), "Studies on Liver Alcohol Dehydrogenase I. Equilibria and Initial Reaction Velocities" (PDF), Acta Chem. Scand., 5: 1105–26, doi:10.3891/acta.chem.scand.05-1105. Winer, Alfred D.; Nurmikko, V.; Hartiala, K.; Hartiala, K.; Veige, S.; Diczfalusy, E. (1958), "A Note of the Substrate Specificity of Horse Liver Alcohol Dehydrogenase" (PDF), Acta Chem. Scand., 12: 1695–96, doi:10.3891/acta.chem.scand.12-1695. Merritt, A. Donald; Tomkins, Gordon M. (1959), "Reversible Oxidation of Cyclic Secondary Alcohols by Liver Alcohol Dehydrogenase", J. Biol. Chem., 234 (10): 2778–82. von Wartburg, Jean-Pierre; Bethane, J. L.; Vallee, B. L. (1964), "Human Liver Alcohol Dehydrogenase: Kinetic and Physiochemical Properties", Biochemistry, 3 (11): 1775–82, doi:10.1021/bi00899a033.
  30. ↑ 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 Butanols: four isomers, Environmental Health Criteria monograph No. 65, Geneva: World Health Organization, 1987, ISBN 92-4-154265-9.
  31. ↑ Ethanol (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, August 2005.
  32. ↑ McCreery, N. J.; Hunt, W. A. (1978), "Physico-chemical correlates of alcohol intoxication", Neuropharmacology, 17 (7): 451–61, PMID 567755, doi:10.1016/0028-3908(78)90050-3.
  33. ↑ Woo, Kang-Lyung (2005), "Determination of low molecular weight alcohols including fusel oil in various samples by diethyl ether extraction and capillary gas chromatography", J. AOAC Int., 88 (5): 1419–27, PMID 16385992, doi:10.5555/jaoi.2005.88.5.1419.
  34. ↑ Lachenmeier, Dirk W.; Haupt, Simone; Schulz, Katja (2008), "Defining maximum levels of higher alcohols in alcoholic beverages and surrogate alcohol products", Regul. Toxicol. Pharmacol., 50 (3): 313–21, PMID 18295386, doi:10.1016/j.yrtph.2007.12.008.
  35. ↑ Hori, Hisako; Fujii, Wataru; Hatanaka, Yutaka; Suwa, Yoshihide (2003), "Effects of fusel oil on animal hangover models", Alcohol. Clin. Exp. Res., 27 (8 Suppl): 37S–41S, PMID 12960505, doi:10.1097/01.ALC.0000078828.49740.48.
  36. ↑ Bunc, M.; Pezdir, T.; Možina, H.; Možina, M.; Brvar, M. (2006), "Butanol ingestion in an airport hangar", Hum. Exp. Toxicol., 25 (4): 195–97, PMID 16696295, doi:10.1191/0960327106ht607oa.
  37. 1 2 Wysocki, C. J.; Dalton, P. (1996), Odor and Irritation Thresholds for 1-Butanol in Humans, Philadelphia: Monell Chemical Senses Center, cited in n-Butanol (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, April 2005.
  38. ↑ 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, PMID 9580447, doi:10.1007/s004200050256.
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