Propan-1-ol

Propan-1-ol

Chembox new
Name = Propanol
ImageFile = Propan-1-ol-2D-skeletal.png ImageName = Propan-1-ol
ImageFile1 = Propanol_flat_structure.png ImageFile2 = Propan-1-ol-3D-balls.png IUPACName = propan-1-ol
OtherNames = 1-propanol
propyl alcohol
"n"-propanol
"n"-propyl alcohol
propanol
Section1 = Chembox Identifiers
SMILES = CCCO
CASNo = 71-23-8
ChemSpiderID = 1004
RTECS = UH8225000
Section2 = Chembox Properties
Formula = C3H8O
MolarMass = 60.09 g/mol
Appearance = Clear, colourless liquid
Density = 0.8034 g/cm3, liquid
Solubility = Fully miscible
MeltingPt = −126.5 °C (146.7 K)
BoilingPt = 97.1 °C (370.3 K)
pKa = (~16)
Viscosity = 1.938 cP at 25°C
Section3 = Chembox Structure
Dipole = 1.68 D
Section7 = Chembox Hazards
ExternalMSDS =
EUClass = Flammable (F)
Irritant (Xi)
NFPA-H = 1
NFPA-F = 3
NFPA-R =
RPhrases = R11, R41, R67
SPhrases = S2, S7, S16, S24,
S26, S39
FlashPt = 15 °C
Section8 = Chembox Related
Function = alcohols
OtherFunctn = Ethanol
Propan-2-ol
Butan-1-ol
OtherCpds = Propionaldehyde
Propionic acid
1-Chloropropane
Propyl acetate

Propan-1-ol is a primary alcohol with the formula CH3CH2CH2OH. It is also known as 1-propanol, 1-propyl alcohol, n-propyl alcohol, or simply propanol. It is an isomer of propan-2-ol. It is used as a solvent in the pharmaceutical industry, and for resins and cellulose esters. It is formed naturally in small amounts during many fermentation processes.

Chemical properties

1-Propanol shows the normal reactions of a primary alcohol. Thus it can be converted to alkyl halides; for example red phosphorus and iodine produce "n"-propyl iodide in 90% yield, while PCl3 with catalytic ZnCl2 gives 1-chloropropane. Reaction with acetic acid in the presence of an H2SO4 catalyst under Fischer esterification conditions gives propyl acetate, while refluxing propanol overnight with formic acid alone can produce propyl formate in 65% yield. Oxidation of 1-propanol with Na2Cr2O7 and H2SO4 gives only a 36% yield of propionaldehyde, and therefore for this type of reaction higher yielding methods using PCC or the Swern oxidation are recommended. Oxidation with chromic acid yields propionic acid


Preparation

1-Propanol is a major constituent of fusel oil, a by-product formed from certain amino acids when potatoes or grains are fermented to produce ethanol. This is no longer a significant source of propanol.

1-Propanol is manufactured by catalytic hydrogenation of propionaldehyde. The propionaldehyde is itself produced via the oxo process, by hydroformylation of ethylene using carbon monoxide and hydrogen in the presence of a catalyst such as cobalt octacarbonyl or a rhodium complex.

:(1) H2C=CH2 + CO + H2 → CH3CH2CH=O

:(2) CH3CH2CH=O + H2 → CH3CH2CH2OH

A traditional laboratory preparation of 1-propanol involves treating "n"-propyl iodide with moist Ag2O.

History

1-Propanol was discovered in 1853 by Chancel, who obtained it by fractional distillation of fusel oil.

References

#
# "Handbook of Chemistry and Physics", 71st edition, CRC Press, Ann Arbor, Michigan, 1990.
# "The Merck Index", 7th edition, Merck & Co, Rahway, New Jersey, USA, 1960.
# Perkin, W. H.; Kipping, F. S. (1922). "Organic Chemistry", London: W. & R. Chambers.

External links

* [http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc05/icsc0553.htm International Chemical Safety Card 0553]
* [http://www.cdc.gov/niosh/npg/npgd0533.html NIOSH Pocket Guide to Chemical Hazards]


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