Propan-1-ol
Information about Propan-1-ol
| 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 | ) 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) | |
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)
Some example reactions of 1-propanol
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
- 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.
External links
Alcohols | |
|---|---|
| Primary alcohols | Methanol • Ethanol • Propan-1-ol • Butanol • Isobutanol • 1-Pentanol • 1-Hexanol • 1-Heptanol • Octanol • Nonanol • Decanol • Dodecanol • 1-Tetradecanol • Cetyl alcohol • Stearyl alcohol |
| Secondary alcohols | Isopropyl alcohol • 2-Butanol • 2-Hexanol |
| Tertiary alcohols | tert-Butanol |
Antiseptics 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 |
IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).
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Water (H2O, HOH) is the most abundant molecule on Earth's surface, composing of about 70% of the Earth's surface as liquid and solid state in addition to being found in the atmosphere as a vapor.
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boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid.[1][2][3][4]
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An acid dissociation constant, denoted by Ka, is an equilibrium constant for the dissociation of a weak acid. According to the Brønsted-Lowry theory of acids and bases an acid is only recognised by its reaction with a base.
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The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. It is defined as 10-18 statcoulomb centimeter (or 10-20 esu m). In SI units, 1 D equals 3.33564*10-30 coulomb meter. It is named after the physicist Peter J.
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P in mm Hg 1 10 40 100 400 760 1520 3800 7600 15600 30400 45600
T in °C –15.0 14.7 36.4 52.8 82.0 97.8 117.0 149.0 177.0 210.8 250.0 — Table data obtained from CRC Handbook of Chemistry and Physics 44th ed.
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T in °C –15.0 14.7 36.4 52.8 82.0 97.8 117.0 149.0 177.0 210.8 250.0 — Table data obtained from CRC Handbook of Chemistry and Physics 44th ed.
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alcohol is any organic compound in which a hydroxyl group (-OH) is bound to a carbon atom of an alkyl or substituted alkyl group. The general formula for a simple acyclic alcohol is CnH2n+1OH.
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