1-Butanol

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N-Butanol
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1-Butanol
Skeletal formula of n-butanol
Skeletal formula of n-butanol
Spacefill model of n-butanol
Spacefill model of n-butanol
Skeletal formula of n-butanol with all explicit hydrogens added
Names
Preferred IUPAC name
Butan-1-ol[1]
Other names
n-Butanol
n-Butyl alcohol
n-Butyl hydroxide
n-Propylcarbinol
n-Propylmethanol
1-Hydroxybutane
Methylolpropane
Identifiers
3D model (
JSmol
)
3DMet
969148
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.000.683 Edit this at Wikidata
EC Number
  • 200-751-6
25753
KEGG
MeSH 1-Butanol
RTECS number
  • EO1400000
UNII
UN number 1120
  • InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3 checkY
    Key: LRHPLDYGYMQRHN-UHFFFAOYSA-N checkY
  • InChI=1/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3
  • OCCCC
Properties
C4H10O
Molar mass 74.123 g·mol−1
Appearance Colourless, refractive liquid
Odor banana-like,[2] harsh, alcoholic and sweet
Density 0.81 g/cm3
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 at 25 °C
Solubility very soluble in
ethyl ether
log P 0.839
Vapor pressure 0.58 kPa (20 °C) ILO International Chemical Safety Cards (ICSC)
Acidity (pKa) 16.10
−56.536·10−6 cm3/mol
1.3993 (20 °C)
Viscosity 2.573 mPa·s (at 25 °C) [3]
1.66 D
Thermochemistry
225.7 J/(K·mol)
Std enthalpy of
formation
(ΔfH⦵298)
 −328(4) kJ/mol
Std enthalpy of
combustion
(ΔcH⦵298)
 −2670(20) kJ/mol
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 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. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
3
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 h)[5]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 100 ppm (300 mg/m3)[4]
REL (Recommended)
 C 50 ppm (150 mg/m3) [skin][4]
IDLH
(Immediate danger)
 1400 ppm[4]
Safety data sheet (SDS) ICSC 0111
Related compounds
Related compounds
Butanethiol
n-Butylamine
Diethyl ether
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 checkY☒N ?)

1-Butanol, also known as butan-1-ol or n-butanol, is a

tert-butanol. The unmodified term butanol
usually refers to the straight chain isomer.

1-Butanol occurs naturally as a minor product of the

saccharides[6] and is present in many foods and drinks.[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 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.[8]

Production

Since the 1950s, most 1-butanol is produced by the

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.

A second method for producing butanol involves the

Reppe reaction of propylene with CO and water:[11]

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.https://pubs.rsc.org/en/content/articlehtml/2014/gc/c3gc41183d

Industrial use

Constituting 85% of its use, 1-butanol is mainly used in the production of

n-butylamines.[11]

Biofuel

1-Butanol has been proposed as a substitute for

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.[12]

The production of, or in some cases, the use of, the following substances may result in exposure to 1-butanol:

pyroxylin plastics, rayon, safety glass, shellac varnish, and waterproofed cloth.[7]

Occurrence in nature

Butan-1-ol occurs naturally as a result of carbohydrate fermentation in a number of alcoholic beverages, including beer,[13] grape brandies,[14] wine,[15] and whisky.[16] It has been detected in the volatiles of hops,[17] jack fruit,[18] heat-treated milks,[19] musk melon,[20] cheese,[21] southern pea seed,[22] and cooked rice.[23] 1-Butanol is also formed during deep frying of corn oil, cottonseed oil, trilinolein, and triolein.[24]

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.[25] It is a natural component of many alcoholic beverages, albeit in low and variable concentrations.[26][27] It (along with similar fusel alcohols) is reputed to be responsible for severe hangovers, although experiments in animal models show no evidence for this.[28]

1-Butanol is used as an ingredient in processed and artificial flavorings,[29] and for the extraction of lipid-free protein from egg yolk,[30] 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.[31]

Metabolism and toxicity

The acute toxicity of 1-butanol is relatively low, with oral

β-oxidation pathway. In the rat, only 0.03% of an oral dose of 2,000 mg/kg was excreted in the urine.[33] 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.[34]

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.

defatting. No skin sensitization has been observed. Irritation of the respiratory pathways occurs only at very high concentrations (>2,400 ppm).[35]

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.[35][36]

See also

External links

  • International Chemical Safety Card 0111
  • NIOSH Pocket Guide to Chemical Hazards. "#0076". National Institute for Occupational Safety and Health (NIOSH).
  • SIDS Initial Assessment Report for n-Butanol from the
    Organisation for Economic Co-operation and Development
    (OECD)
  • Environmental Health Criteria 65: Butanols: four isomers
  • IPCS Health and Safety Guide 3: 1-Butanol

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. doi:10.1016/j.jct.2007.05.016
    .
  4. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0076". National Institute for Occupational Safety and Health (NIOSH).
  5. ^ a b "N-butyl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  6. PMID 18281432
    .
  7. ^
    ISBN 92-4-154265-9
    .
  8. ^ a b c d 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. ISBN 92-4-154265-9
    .
  11. ^
    ISBN 978-3527306732
    ..
  12. S2CID 35454212
    .
  13. ISBN 92-4-154265-9
    .
  14. doi:10.1021/jf60222a031
    .
  15. ISBN 92-4-154265-9
    .
  16. ISBN 92-4-154265-9
    .
  17. doi:10.1021/jf60220a036
    .
  18. doi:10.1111/j.1365-2621.1978.tb02375.x
    .
  19. S2CID 85985458
    .
  20. doi:10.1016/0308-8146(78)90042-0
    .
  21. doi:10.1021/jf60216a037
    .
  22. doi:10.1021/jf60221a040
    .
  23. doi:10.1271/bbb1961.42.1229
    .
  24. ISBN 92-4-154265-9
    .
  25. S2CID 4413113
    .
  26. PMID 16385992
    .
  27. PMID 18295386
    .
  28. PMID 12960505
    .
  29. ISBN 92-4-154265-9
    .
  30. PMID 9762085
    .
  31. doi:10.1002/jsfa.2740291003
    .
  32. ^ Ethanol (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, August 2005.
  33. ISBN 92-4-154265-9
    .
  34. S2CID 19914287
    .
  35. ^ a b 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.
  36. S2CID 25246408
    .
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