1-Propanol
1-Propanol (also propan-1-ol, propanol, n-propyl alcohol) is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colourless, water-miscible liquid. It is an isomer of 2-propanol. 1-Propanol is used as a solvent.
| Names | |
|---|---|
| Pronunciation | ˈprəʊpən.wən.ɒl |
| Preferred IUPAC name Propan-1-ol[1] | |
Other names
| |
| Identifiers | |
| |
3D model (JSmol) |
|
| 3DMet |
|
| 1098242 | |
| ChEBI |
|
| ChEMBL |
|
| ChemSpider |
|
| DrugBank |
|
| ECHA InfoCard | 100.000.679 |
| EC Number |
|
| 25616 | |
| KEGG |
|
| MeSH | 1-Propanol |
PubChem CID |
|
| RTECS number |
|
| UNII |
|
| UN number | 1274 |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C3H8O | |
| Molar mass | 60.096 g·mol−1 |
| Appearance | Colorless liquid |
| Odor | mild, alcohol-like[2] |
| Density | 0.803 g/mL |
| Melting point | −126 °C; −195 °F; 147 K |
| Boiling point | 97 to 98 °C; 206 to 208 °F; 370 to 371 K |
| miscible | |
| log P | 0.329 |
| Vapor pressure | 1.99 kPa (at 20 °C) |
| Acidity (pKa) | 16 |
| Basicity (pKb) | −2 |
| −45.176·10−6 cm3/mol | |
Refractive index (nD) | 1.387 |
| Viscosity | 1.959 mPa·s (at 25 °C) [3] |
| 1.68 D | |
| Thermochemistry | |
Heat capacity (C) | 143.96 J/(K·mol) |
Std molar entropy (S⦵298) | 192.8 J/(K·mol) |
Std enthalpy of formation (ΔfH⦵298) | −302.79…−302.29 kJ/mol |
Std enthalpy of combustion (ΔcH⦵298) | −2.02156…−2.02106 MJ/mol |
| Pharmacology | |
| D08AX03 (WHO) | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | Flammable liquid |
| GHS labelling: | |
| Danger | |
| H225, H302, H318, H336 | |
| P210, P261, P280, P305+P351+P338 | |
| NFPA 704 (fire diamond) | |
| Flash point | 22 °C (72 °F; 295 K) |
| 371 °C (700 °F; 644 K) | |
| Explosive limits | 2.2–13.7%[2] |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 2800 mg/kg (rabbit, oral) 1699 mg/kg (mouse, oral) 1870 mg/kg (rat, oral)[4] |
| NIOSH (US health exposure limits): | |
PEL (Permissible) | TWA 200 ppm (500 mg/m3)[2] |
REL (Recommended) | TWA 200 ppm (500 mg/m3) ST 250 ppm (625 mg/m3) [skin][2] |
IDLH (Immediate danger) | 800 ppm[2] |
| Related compounds | |
Related compounds | Propane Isopropyl alcohol Propanamine Ethanol Butanol |
| Supplementary data page | |
| 1-Propanol (data page) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
History edit
1-Propanol was first discovered in 1853 by the French chemist Marcellin Berthelot through the hydrolysis of propyl chloride.[5] Since then, it has been extensively studied and utilized in various fields.
Recently, the discovery of n-propanol in the interstellar medium (ISM) has garnered significant attention. Researchers detected both conformers of n-propanol (Ga-n-C3H7OH and Aa-n-C3H7OH) in the Giant Molecular Cloud G+0.693-0.027 located in the Galactic Center.[6][7] The derived column densities of n-propanol are (5.5±0.4)×10^13 cm^-2 for the Ga conformer and (3.4±0.3)×10^13 cm^-2 for the Aa conformer, which imply molecular abundances of (4.1±0.3)×10^-10 for Ga-n-C3H7OH and of (2.5±0.2)×10^-10 for Aa-n-C3H7OH[7]
Occurrence edit
Fusel alcohols like 1-Propanol are grain fermentation byproducts, and therefore trace amounts of 1-Propanol are present in many alcoholic beverages. Propanol has been detected in the interstellar medium.[8]
Reactions edit
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, while PCl3 with catalytic ZnCl2 gives n-propyl chloride. Reaction with acetic acid in the presence of an H2SO4 catalyst under Fischer esterification conditions gives propyl acetate. When treated with formic acid it converts to propyl formate. Oxidation of 1-propanol with Na2Cr2O7 and H2SO4 gives propionaldehyde, as does PCC and the Swern oxidation. Oxidation with chromic acid yields propionic acid.
Preparation edit
1-Propanol is manufactured by catalytic hydrogenation of propionaldehyde. Propionaldehyde is 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.[9]
- 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.
Applications edit
1-Propanol, also known as n-propanol or propyl alcohol, is a colorless, flammable liquid with a distinct odor. It is an important organic compound with the chemical formula CH3CH2CH2OH. 1-Propanol finds extensive applications across various industries due to its unique properties and versatility.
Solvent Applications edit
One of the primary uses of 1-propanol is as a solvent in the production of cosmetics, pharmaceuticals, and food additives.[10] Its excellent solvent properties make it suitable for dissolving a wide range of organic compounds. In the cosmetics industry, 1-propanol is used in the formulation of perfumes, lotions, and other personal care products.[10] It helps to dissolve essential oils, fragrances, and other ingredients, ensuring a homogeneous mixture.
Chemical Intermediate edit
1-Propanol is an important chemical intermediate in the synthesis of various organic compounds.[10] It serves as a raw material for the production of propyl acetate, which is widely used as a solvent in the paint and coatings industry.[10] Propyl acetate is known for its fast evaporation rate and excellent solvency, making it suitable for use in quick-drying paints and lacquers.
Another important derivative of 1-propanol is propyl amine, which is used in the production of pesticides, herbicides, and other agricultural chemicals.[10] Propyl amine is also used as a corrosion inhibitor in the oil and gas industry, helping to protect pipelines and equipment from corrosion damage.
Antiseptic Properties edit
Due to its antimicrobial properties, 1-propanol is commonly used in hand sanitizers and disinfectants.[10] It is effective against a wide range of bacteria, viruses, and fungi, making it a valuable ingredient in products designed to prevent the spread of infections. 1-Propanol works by denaturing proteins and disrupting the cell membranes of microorganisms, leading to their inactivation.
In healthcare settings, 1-propanol-based hand sanitizers are widely used by healthcare professionals to maintain hand hygiene and reduce the risk of hospital-acquired infections.[11] The rapid evaporation and non-sticky nature of 1-propanol make it a preferred choice for hand sanitizers compared to other alcohols like ethanol or isopropanol.
Safety edit
1-Propanol is thought to be similar to ethanol in its effects on the human body, but 2–4 times more potent according to a study conducted on rabbits. Many toxicology studies find oral acute LD50 ranging from 1.9 g/kg to 6.5 g/kg (compared to 7.06 g/kg for ethanol). It is metabolized into propionic acid. Effects include alcoholic intoxication and high anion gap metabolic acidosis. As of 2011, one case of lethal poisoning was reported following oral ingestion of 500mL of 1-propanol.[12] Due to lack of long term data, the carcinogenicity of 1-propanol in human beings is unknown.
Uses edit
1-Propanol is mainly used as a solvent, e.g., for inks, resins, and cellulose esters. It is a precursor to more specialized solvents such as glycol monopropyl ether and propyl propionate that are of commercial interest.[9] It is sometimes used as a disinfecting agent.
1-Propanol has high octane number and would be suitable as a motor fuel, but it is too expensive. The research octane number of propanol is 118, and anti-knock index is 108.[13]
References edit
- ^ Favre HA, Powell WH (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. p. 61. doi:10.1039/9781849733069. ISBN 9780854041824.
- ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0533". National Institute for Occupational Safety and Health (NIOSH).
- ^ Pal A, Gaba R (2008). "Volumetric, acoustic, and viscometric studies of molecular interactions in binary mixtures of dipropylene glycol dimethyl ether with 1-alkanols at 298.15 K". J. Chem. Thermodyn. 40 (5): 818–828. doi:10.1016/j.jct.2008.01.008.
- ^ "n-Propyl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ Pourkarim, Fariba; Mirheydari, Seyyedeh Narjes; Martinez, Fleming; Jouyban, Abolghasem (2019-05-05). "Solubility of acetaminophen in 1-propanol + water mixtures at T = 293.2–313.2 K". Physics and Chemistry of Liquids. 58 (4): 456–472. doi:10.1080/00319104.2019.1611827. ISSN 0031-9104.
- ^ Ohtake, Toshiyuki; Kawase, Naoki; Pontrelli, Sammy; Nitta, Katsuaki; Laviña, Walter A.; Shen, Claire R.; Putri, Sastia P.; Liao, James C.; Fukusaki, Eiichiro (2022-04-14). "Metabolomics-Driven Identification of the Rate-Limiting Steps in 1-Propanol Production". Frontiers in Microbiology. 13. doi:10.3389/fmicb.2022.871624. ISSN 1664-302X. PMC 9048197. PMID 35495658.
- ^ a b Jiménez-Serra, Izaskun; Rodríguez-Almeida, Lucas F.; Martín-Pintado, Jesús; Rivilla, Víctor M.; Melosso, Mattia; Zeng, Shaoshan; Colzi, Laura; Kawashima, Yoshiyuki; Hirota, Eizi; Puzzarini, Cristina; Tercero, Belén; de Vicente, Pablo; Rico-Villas, Fernando; Requena-Torres, Miguel A.; Martín, Sergio (July 2022). "Precursors of fatty alcohols in the ISM: Discovery of n-propanol". Astronomy & Astrophysics. 663: A181. arXiv:2204.08267. Bibcode:2022A&A...663A.181J. doi:10.1051/0004-6361/202142699. ISSN 0004-6361.
- ^ Jiménez-Serra, Izaskun; Rodríguez-Almeida, Lucas F.; Martín-Pintado, Jesús; Rivilla, Víctor M.; Melosso, Mattia; Zeng, Shaoshan; Colzi, Laura; Kawashima, Yoshiyuki; Hirota, Eizi; Puzzarini, Cristina; Tercero, Belén; de Vicente, Pablo; Rico-Villas, Fernando; Requena-Torres, Miguel A.; Martín, Sergio (July 2022). "Precursors of fatty alcohols in the ISM: Discovery of n-propanol". Astronomy & Astrophysics. 663: A181. arXiv:2204.08267. Bibcode:2022A&A...663A.181J. doi:10.1051/0004-6361/202142699. ISSN 0004-6361.
- ^ a b Papa AJ (2011). "Propanols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_173.pub2. ISBN 9783527303854.
- ^ a b c d e f Zhang, Lin-Shang; Xu, Pei; Chu, Mei-Yun; Zong, Min-Hua; Yang, Ji-Guo; Lou, Wen-Yong (2019-10-21). "Using 1-propanol to significantly enhance the production of valuable odd-chain fatty acids by Rhodococcus opacus PD630". World Journal of Microbiology and Biotechnology. 35 (11). doi:10.1007/s11274-019-2748-0. ISSN 0959-3993.
- ^ Lang, Reinhold Andreas; Egli-Gany, Dianne; Brill, Florian Holger Hubert; Böttrich, Johannes Georg; Breuer, Marion; Breuer, Burkhard; Kirschner, Martin Hartwig (2010-12-01). "Transdermal absorption of ethanol- and 1-propanol-containing hand disinfectants". Langenbeck's Archives of Surgery. 396 (7): 1055–1060. doi:10.1007/s00423-010-0720-4. ISSN 1435-2443. PMID 21116645.
- ^ Unmack JL (2011). "N-Propanol Health-Base Assessment and Recommendation for HEAC" (PDF).
- ^ "Bioalcohols". Biofuel.org.uk. 2010. Retrieved 16 Apr 2014.
Further reading edit
- 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 DR, ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). TF-CRC. ISBN 0849304873.
- O'Neil MJ, ed. (2006). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (14th ed.). Merck. ISBN 091191000X.
- Perkin WH, Kipping FS (1922). Organic Chemistry. London: W. & R. Chambers. ISBN 0080223540.
External links edit
- International Chemical Safety Card 0553
- NIOSH Pocket Guide to Chemical Hazards