Back 1-بوتانول Arabic Butanol-1 Azerbaijani N-بوتانول AZB Butan-1-ol Catalan Butan-1-ol Czech 1-Butanol German 1-βουτανόλη Greek 1-Butanolo Esperanto Butan-1-ol Spanish 1-Butanol Basque

1-Butanol

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 acetone
miscible with ethanol, 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)
−328(4) kJ/mol
−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 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[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]

  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. ^ 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.
  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. ^ 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, Bibcode:2008ApEnM..74.2259H, doi:10.1128/AEM.02625-07, PMC 2293160, PMID 18281432.
  7. ^ a b Butanols: four isomers, Environmental Health Criteria monograph No. 65, Geneva: World Health Organization, 1987, ISBN 92-4-154265-9.
  8. ^ a b 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.

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