Propan-1-ol

Propan-1-ol

Propan-1-ol
General
Systematic name	propan-1-ol
Other names	1-propanolpropyl alcoholn-propanoln-propyl alcoholpropanol
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 (pKa)	(~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 andproperties	n, εr, etc.
Thermodynamicdata	Phase behaviourSolid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related alcohols	EthanolPropan-2-olButan-1-ol
Related compounds	PropionaldehydePropionic acid1-ChloropropanePropyl 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.

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Contents 1 Chemical properties 2 Preparation 3 History 4 References

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

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.

History

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

References

1. 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
2. Handbook of Chemistry and Physics, 71st edition, CRC Press, Ann Arbor, Michigan, 1990.
3. The Merck Index, 7th edition, Merck & Co, Rahway, New Jersey, USA, 1960.
4. Perkin, W. H.; Kipping, F. S. (1922). Organic Chemistry, London: W. & R. Chambers.

v • d • eAlcohols
(0°)	Methanol
Primary alcohols (1°)	Ethanol · Propan-1-ol · Butanol · Isobutanol · 1-Pentanol · 1-Hexanol · 1-Heptanol · Octanol · Nonanol · Decanol · Undecanol · Dodecanol · 1-Tetradecanol · Cetyl alcohol · Stearyl alcohol · Arachidyl alcohol · Docosanol · Octanosol · Triacontanol
Secondary alcohols (2°)	Isopropyl alcohol · 2-Butanol · 2-Hexanol
Tertiary alcohols (3°)	tert-Butanol

v • d • eAntiseptics and disinfectants (D08)
Acridine derivatives	Ethacridine lactate - Aminoacridine - Euflavine
Biguanides and amidines	Dibrompropamidine - Chlorhexidine - Propamidine - Hexamidine - Polihexanide
Phenol and derivatives	Hexachlorophene - Policresulen - Phenol - Triclosan - Chloroxylenol - Biphenylol
Nitrofuran derivatives	Nitrofurazone
Iodine products	Iodine/octylphenoxypolyglycolether - Povidone-iodine - Diiodohydroxypropane
Quinoline derivatives	Dequalinium - Chlorquinaldol - Oxyquinoline - Clioquinol
Quaternary ammonium compounds	Benzalkonium - Cetrimonium - Cetylpyridinium - Cetrimide - Benzoxonium chloride - Didecyldimethylammonium chloride
Mercurial products	Mercuric amidochloride - Phenylmercuric borate - Mercuric chloride - Mercurochrome - Thiomersal - Mercuric iodide
Silver compounds	Silver nitrate
Others	Hydrogen peroxide - Eosin - Propanol - Tosylchloramide sodium - Isopropanol - Potassium permanganate - Sodium hypochlorite - Ethanol

Categories: Alcohols | Alcohol solvents