Propan-1-ol

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Propan-1-ol

General
Systematic name	propan-1-ol
Other names	1-propanol propyl alcohol n-propanol n-propyl alcohol propanol
Molecular formula	C₃H₈O
SMILES	CCCO
Molar mass	60.09 g/mol
Appearance	Clear, colourless liquid
CAS number	[71-23-8]
Properties
Density and phase	0.8034 g/cm³, liquid
Solubility in water	Fully miscible
All common solvents:	Fully miscible
Melting point	−126.5 °C (146.7 K)
Boiling point	97.1 °C (370.3 K)
Acidity (pK_a)	(~16)
Viscosity	2.26 cP at ?°C
Dipole moment	1.68 D
Hazards
MSDS	External MSDS
EU classification	Flammable (F) Irritant (Xi)
NFPA 704	3 1 0
R-phrases	R11, R41, R67
S-phrases	S2, S7, S16, S24, S26, S39
Flash point	15 °C
RTECS number	UH8225000
Supplementary data page
Structure and properties	n, ε_r, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related alcohols	Ethanol Propan-2-ol Butan-1-ol
Related 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) Infobox disclaimer and references

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.

1 Chemical properties
2 Preparation
3 History
4 References
5 External links

[edit] 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 1-iodopropane 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

[edit] 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 the material.

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 1-iodopropane with moist Ag₂O.

[edit] History

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

[edit] References

Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. (1989). Vogel's Textbook of Practical Organic Chemistry (5th Edn.), Harlow:Longman. ISBN 0-582-46236-3
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.