1-Propanol
| 1-Propanol | |
|---|---|
 | |
 |
 |
| Propan-1-ol[1] | |
| Other names
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| Identifiers | |
| CAS number | 71-23-8  |
| PubChem | 1031 |
| ChemSpider | 1004 |
| UNII | 96F264O9SV |
| EC number | 200-746-9 |
| UN number | 1274 |
| DrugBank | DB03175 |
| KEGG | C05979  |
| MeSH | 1-Propanol |
| ChEBI | CHEBI:28831 |
| ChEMBL | CHEMBL14687 |
| RTECS number | UH8225000 |
| ATC code | D08 |
| Beilstein Reference | 1098242 |
| Gmelin Reference | 25616 |
| 3DMet | B00883 |
| Jmol-3D images | Image 1 |
| |
| |
| Properties | |
| Molecular formula | C3H8O |
| Molar mass | 60.10 g mol−1 |
| Appearance | Colorless liquid |
| Density | .803 g/mL |
| Melting point | −126 °C; −195 °F; 147 K |
| Boiling point | 97 to 98 °C; 206 to 208 °F; 370 to 371 K |
| Solubility in water | miscible |
| log P | 0.329 |
| Vapor pressure | 1.99 kPa (at 20 °C) |
| Acidity (pKa) | 16 |
| Basicity (pKb) | −2 |
| Refractive index (nD) | 1.387 |
| Viscosity | 1.938 mPa s |
| Dipole moment | 1.68 D |
| Thermochemistry | |
| Std enthalpy of formation ΔfH |
−302.79–−302.29 kJ mol-1 |
| Std enthalpy of combustion ΔcH |
−2.02156–−2.02106 MJ mol-1 |
| Standard molar entropy S |
192.8 J K−1 mol−1 |
| Specific heat capacity, C | 143.96 J K−1 mol−1 |
| Hazards | |
| GHS pictograms |    |
| GHS signal word | DANGER |
| GHS hazard statements | H225, H318, H336 |
| GHS precautionary statements | P210, P261, P280, P305+351+338 |
| EU Index | 603-003-00-0 |
| EU classification |  F  Xi |
| R-phrases | R11, R41, R67 |
| S-phrases | (S2), S7, S16, S24, S26, S39 |
| NFPA 704 |
 3
1
0
|
| Flash point | 22 °C; 72 °F; 295 K |
| Autoignition temperature | 371 °C; 700 °F; 644 K |
| Explosive limits | 13.7% |
| Related compounds | |
| Related compounds | Butane |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
1-Propanol is a primary alcohol with the formula CH3CH2CH2OH. This colorless liquid is also known as propan-1-ol, 1-propyl alcohol, n-propyl alcohol, n-propanol, or simply propanol. It is an isomer of isopropanol (2-propanol, isopropyl alcohol). It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry mainly for resins and cellulose esters.
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 n-propyl iodide in 80% 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 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.[2]
- H2C=CH2 + CO + H2 → CH3CH2CH=O
- CH3CH2CH=O + H2 → CH3CH2CH2OH
A traditional laboratory preparation of 1-propanol involves treating n-propyl iodide with moist Ag2O.
1-Propanol was discovered in 1853 by Chancel, who obtained it by fractional distillation of fusel oil. Indeed 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 process is no longer a significant source of 1-propanol.
Safety
1-Propanol is thought to be similar to ethanol in its effects on human body, but 2-4 times more potent. Oral LD50 in rats is 1870 mg/kg (compared to 7060 mg/kg for ethanol). It is metabolized into propionic acid. Effects include alcoholic intoxication and high anion gap metabolic acidosis. As of 2011, only one case of lethal 1-propanol poisoning was reported.[3]
Inhalation
Although this method is rare, it does indeed exist. Propanol might be much more convenient than ethanol for inhalation because of its potency with nebulizers.
References
- ↑ "1-Propanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 10 October 2011.
- ↑ Anthony J. Papa "Propanols" in Ullmann’s Encyclopedia of Industrial Chemistry 2011, Wiley-VCH, Weinheim. doi:10.1002/14356007.a22_173.pub2
- ↑ "N-PROPANOL Health-Base Assessment and Recommendation for HEAC".
Further reading
- Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. (1989), Vogel's Textbook of Practical Organic Chemistry (5th ed.), Harlow: Longman, ISBN 0-582-46236-3
- Lide, David R., ed. (2006-06-26). CRC Handbook of Chemistry and Physics, 87th Edition (87 ed.). TF-CRC. ISBN 0-8493-0487-3.
- Maryadele J. O'Neil, ed. (2006-11-03). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (14 ed.). Merck. ISBN 0-911910-00-X.
- Perkin, W. H.; Kipping, F. S (1922). Organic Chemistry. London: W. & R. Chambers. ISBN 0-08-022354-0.
External links
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