Propan-1-ol

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Propan-1-ol
Propan-1-ol
Propan-1-oll
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 (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
NFPA 704.svg
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, εr, 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

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Overview

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 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 + H2CH3CH2CH=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. Template:VogelOrganic
  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.

External links


de:1-Propanol

el:Προπανόληit:1-propanol lb:Propan-1-ol lv:Propanols nl:1-propanolfi:1-propanoli


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