Propan-1-ol

Propan-1-ol
IUPAC name	propan-1-ol
Other names	1-propanol propyl alcohol n-propanol n-propyl alcohol propanol
Identifiers
InChI	InChI=1/C3H8O/c1-2-3-4/h4H,2-3H2,1H3
InChIKey	BDERNNFJNOPAEC-UHFFFAOYAO
Standard InChI	InChI=1S/C3H8O/c1-2-3-4/h4H,2-3H2,1H3
Standard InChIKey	BDERNNFJNOPAEC-UHFFFAOYSA-N
CAS number	[71-23-8]
EC number	200-746-9
RTECS	UH8225000
ChemSpider	1004
SMILES	CCCO
Properties
Chemical formula	C3H8O
Molar mass	60.095 g/mol
Appearance	colourless liquid
Density	0.8034 g/cm3, liquid
Melting point	−126.5 °C (146.7 K)
Boiling point	97.1 °C (370.3 K)
Solubility in water	miscible
log P	0.25
Vapor pressure	2.0 kPa (20 ºC)
Acidity (pKa)	~16
Viscosity	1.938 cP at 25°C
Dipole moment	1.68 D
Thermochemistry
Hazards
Material safety data sheet (MSDS)	ICSC 0553
EU index number	603-003-00-0
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H225, H318, H336
Flash point	15 °C (59 ºF)
Autoignition temp.	371 ºC (700 ºF)
Explosive limits	2.1–13.5%
PEL (U.S.)	200 ppm TWA
IDLH level	800 ppm
Related compounds
Other alcohols	Ethanol Isopropanol Butan-1-ol
Other compounds	Propionaldehyde Propionic acid 1-Chloropropane Propyl acetate
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Propan-1-ol is a primary alcohol with the Molecular formula of C₃H₈O. 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

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

Further reading

• Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longman: Harlow, 1989. ISBN 0-582-46236-3
• CRC Handbook of Chemistry and Physics, 87th ed.; Lide, David R., Ed.; CRC Press: Boca Raton, FL, 2006. ISBN 0-8493-0487-3
• The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 14th ed.; O'Neil, Maryadele J., Ed.; Merck, 2006. ISBN 091191000X
• Perkin, W. H.; Kipping, F. S Organic Chemistry; W. & R. Chambers: London, 1922

External links

• International Chemical Safety Card 0553
• NIOSH Pocket Guide to Chemical Hazards 0533