Propan-1-ol
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| Propan-1-ol | |
|---|---|
| Image:Propan-1-ol-2D-skeletal.png Image:Propan-1-ol-3D-vdW.png | |
| 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) 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 + 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
- Template:VogelOrganic
- 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 |
el:Προπανόληit:1-propanol lb:Propan-1-ol lv:Propanols nl:1-propanol ja:1-プロパノール fi:1-propanoli vi:1-Prôpanol
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
