N-Butanol: History
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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, and is present in many foods and beverages. It is also a permitted artificial flavorant in the United States, used in butter, cream, fruit, rum, whiskey, ice cream and ices, candy, baked goods and cordials. It is also used in a wide range of consumer products. 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.

  • n-butyl alcohol
  • butanol
  • n-butanol

1. Production

Since the 1950s, most n-butanol is produced by the hydroformylation of propylene (oxo process) to form butyraldehyde. Typical catalysts are based on cobalt and rhodium. The butyraldehyde is then hydrogenated to produce butanol.

A second method for producing butanol involves the Reppe reaction of propylene with CO and water:[1]

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.

2. Industrial Use

Constituting 85% of its use, n-butanol is mainly used in the production of varnishes. It is a popular solvent, e.g. for nitrocellulose. A variety of butyl esters are used as solvents, e.g. butoxyethanol. 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.[1]

2.1. Biofuel

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.

Butanol is considered as a potential biofuel (butanol fuel). Butanol at 85 percent strength can be used in cars designed for gasoline (petrol) without any change to the engine (unlike 85% ethanol), and it provides more energy for a given volume than ethanol, due to butanol's lower oxygen content,[2] and 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.[3]

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.[4]

3. Occurrence in Nature

Honey bees use n-butanol as an Alarm pheromone.

3.1. Food

n-Butanol occurs naturally as a result of carbohydrate fermentation in a number of alcoholic beverages, including beer,[5] grape brandies,[6] wine,[7] and whisky.[8] It has been detected in the volatiles of hops,[9] jack fruit,[10] heat-treated milks,[11] musk melon,[12] cheese,[13] southern pea seed,[14] and cooked rice.[15] n-Butanol is also formed during deep frying of corn oil, cottonseed oil, trilinolein, and triolein.[16]

n-Butanol is a natural component of many alcoholic beverages, albeit in low (but variable) concentrations.[17][18] It (along with similar fusel alcohols) is reputed to be responsible for severe hangovers, although experiments in animal models show no evidence for this.[19]

n-Butanol is used as an ingredient in processed and artificial flavourings,[20] and for the extraction of lipid-free protein from egg yolk,[21] 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.[22]

4. Metabolism and Toxicity

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).[23][24] [1]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.[25] 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 about 6 times higher than that of ethanol, possibly because of its slower transformation by alcohol dehydrogenase.[26]

4.1. 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.[23] 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).[27]

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.[27][28]

The content is sourced from: https://handwiki.org/wiki/Chemistry:N-Butanol

References

  1. Hahn, Heinz-Dieter; Dämbkes, Georg; Rupprich, Norbert (2005). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_463. . https://dx.doi.org/10.1002%2F14356007.a04_463
  2. Schmidt-Rohr, K. (2015). "Why Combustions Are Always Exothermic, Yielding About 418 kJ per Mole of O2", J. Chem. Educ. 92: 2094-2099. https://dx.doi.org/10.1021/acs.jchemed.5b00333
  3. 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.  https://dx.doi.org/10.1007%2Fs00253-007-1163-x
  4. Butanols: four isomers, Environmental Health Criteria monograph No. 65, Geneva: World Health Organization, 1987, ISBN 92-4-154265-9, http://www.inchem.org/documents/ehc/ehc/ehc65.htm .
  5. 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, http://www.inchem.org/documents/ehc/ehc/ehc65.htm .
  6. 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 . https://dx.doi.org/10.1021%2Fjf60222a031
  7. 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, http://www.inchem.org/documents/ehc/ehc/ehc65.htm .
  8. 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, http://www.inchem.org/documents/ehc/ehc/ehc65.htm .
  9. 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 . https://dx.doi.org/10.1021%2Fjf60220a036
  10. 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 . https://dx.doi.org/10.1111%2Fj.1365-2621.1978.tb02375.x
  11. 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 . https://dx.doi.org/10.1017%2FS0022029900016617
  12. 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 . https://dx.doi.org/10.1016%2F0308-8146%2878%2990042-0
  13. 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 . https://dx.doi.org/10.1021%2Fjf60216a037
  14. 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 . https://dx.doi.org/10.1021%2Fjf60221a040
  15. 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, http://www.journalarchive.jst.go.jp/jnlpdf.php?cdjournal=bbb1961&cdvol=42&noissue=6&startpage=1229&lang=en&from=jnlabstract .
  16. 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, doi:10.1007/BF02665369, PMID 730972 , cited in Butanols: four isomers, Environmental Health Criteria monograph No. 65, Geneva: World Health Organization, 1987, ISBN 92-4-154265-9, http://www.inchem.org/documents/ehc/ehc/ehc65.htm .
  17. 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 . http://www.ncbi.nlm.nih.gov/pubmed/16385992
  18. 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, doi:10.1016/j.yrtph.2007.12.008, PMID 18295386 . https://dx.doi.org/10.1016%2Fj.yrtph.2007.12.008
  19. 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, doi:10.1097/01.ALC.0000078828.49740.48, PMID 12960505 . https://dx.doi.org/10.1097%2F01.ALC.0000078828.49740.48
  20. 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, http://www.inchem.org/documents/ehc/ehc/ehc65.htm .
  21. Meslar, Harry W.; White, Harold B., III (1978), "Preparation of lipid-free protein extracts of egg yolk", Anal. Biochem. 91 (1): 75–81, doi:10.1016/0003-2697(78)90817-5, PMID 9762085 . https://dx.doi.org/10.1016%2F0003-2697%2878%2990817-5
  22. 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 . https://dx.doi.org/10.1002%2Fjsfa.2740291003
  23. n-Butanol, SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, April 2005, http://www.inchem.org/documents/sids/sids/71363.pdf .
  24. Ethanol, SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, August 2005, http://www.inchem.org/documents/sids/sids/64175.pdf .
  25. 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, http://www.inchem.org/documents/ehc/ehc/ehc65.htm .
  26. McCreery, N. J.; Hunt, W. A. (1978), "Physico-chemical correlates of alcohol intoxication", Neuropharmacology 17 (7): 451–61, doi:10.1016/0028-3908(78)90050-3, PMID 567755 . https://dx.doi.org/10.1016%2F0028-3908%2878%2990050-3
  27. Wysocki, C. J.; Dalton, P. (1996), Odor and Irritation Thresholds for 1-Butanol in Humans, Philadelphia: Monell Chemical Senses Center , cited in n-Butanol, SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, April 2005, http://www.inchem.org/documents/sids/sids/71363.pdf .
  28. 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, doi:10.1007/s004200050256, PMID 9580447, http://www.escholarship.org/uc/item/52f8x48p .
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