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N-Butanol

n-Butanol
Skeletal formula of n-butanol
Spacefill model of n-butanol
Skeletal formula of n-butanol with all explicit hydrogens added
Names
Systematic IUPAC name
Butan-1-ol
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
71-36-3 YesY
3D model (Jmol) Interactive image
3DMet B00907
969148
ChEBI CHEBI:28885 N
ChEMBL ChEMBL14245 YesY
ChemSpider 258 YesY
DrugBank DB02145 N
ECHA InfoCard 100.000.683
EC Number 200-751-6
25753
KEGG D03200 YesY
MeSH 1-Butanol
PubChem 263
RTECS number EO1400000
UNII 8PJ61P6TS3 YesY
UN number 1120
Properties
C4H10O
Molar mass 74.12 g·mol−1
Appearance Colourless, refractive liquid
Odor banana-like, 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)
Acidity (pKa) 16.10
-56.536·10−6 cm3/mol
1.3993 (20 °C)
Viscosity 2.573 mPa×s (at 25 °C)
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
Harmful Xn
R-phrases R10, R22, R37/38, R41, R67
S-phrases (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
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):
LD50 (median dose)
790 mg/kg (rat, oral)
3484 mg/kg (rabbit, oral)
790 mg/kg (rat, oral)
1700 mg/kg (dog, oral)
9221 ppm (mammal)
8000 ppm (rat, 4 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 100 ppm (300 mg/m3)
REL (Recommended)
C 50 ppm (150 mg/m3) [skin]
IDLH (Immediate danger)
1400 ppm
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  (what is YesYN ?)
Infobox references

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

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-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.


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Wikipedia

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