1-Propanol

Primary alcohol compound (CH3CH2CH2OH) changed changed 477208553 Skeletal formula of 1-propanol 1-Propanol ˈ w ə n . p r ə ʊ p ə n ɒ l ' Propan-1-ol.svg skin-invert Ball and stick model of 1-propanol Propan-1-ol-3D-balls.png bg-transparent Propan-1-olNomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) Favre HA, Powell WH The Royal Society of Chemistry 2014 Cambridge 61 10.1039/9781849733069 9780854041824 n-Propyl alcohol n-Propanol Ethyl carbinol 1-Hydroxypropane Propionic alcohol Propionyl alcohol Propionylol Propyl alcohol Propylic alcohol Propylol 1-Propanol (data page) 71-23-8 correct CAS PrOHn-PrOHnPrOHnPrOH 1031 1004 correct chemspider 96F264O9SV correct FDA 200-746-9 1274 DB03175 correct drugbank C05979 correct kegg 1-Propanol 28831 correct EBI 14687 correct EBI UH8225000 1098242 25616 B00883 CCCO 1S/C3H7OH/c1-2-3-4/h4H,2-3H2,1H3 correct chemspider BDERNNFJNOPAEC-UHFFFAOYSA-N correct chemspider 3 8 1 Colorless liquid mild, alcohol-like 0.803 g/mL 147 370 to 371 0.329 1.99 kPa (at 20 °C) 16 −2 miscible 1.387 1.959 mPa·s (at 25 °C)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 10.1016/j.jct.2008.01.008 2008JChTh..40..818P 1.68 D −45.176·10−6 cm3/mol −302.79…−302.29 kJ/mol −2.02156…−2.02106 MJ/mol 192.8 J/(K·mol) 143.96 J/(K·mol) D08 AX03 Flammable liquid flame exclamation mark DANGER 225 302 318 336 210 261 280 305+351+338 1 3 0 22 371 2.2–13.7% TWA 200 ppm (500 mg/m3)0533 800 ppm 2800 mg/kg (rabbit, oral)1699 mg/kg (mouse, oral)1870 mg/kg (rat, oral)71238 n-Propyl alcohol TWA 200 ppm (500 mg/m3) ST 250 ppm (625 mg/m3) [skin] PropaneIsopropyl alcoholPropanamineEthanolButanol 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 liquid and an isomer of 2-propanol. 1-Propanol is used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent. History January 2025 The compound was discovered by Gustave Chancel in 1853 by fractional distillation of fusel oil.Propyl Alcohols 22 4501989-04-14 Propanol, 1- (EHC 102, 1990) https://www.inchem.org/documents/ehc/ehc/ehc102.htm 2026-02-13 INCHEM He measured its boiling point at 96°C, correctly identified its empirical formula, studied some of its chemical properties and gave it two names: propionic alcohol and hydrate of trityl.Wisniak Jaime 2013 Gustav Charles Bonaventure Chancel Educación Química 24 1 23–30 10.1016/S0187-893X(13)73191-4 0187-893X free s:fr:Page:Comptes rendus hebdomadaires des séances de l’Académie des sciences, tome 037, 1853.djvu/414 After several unsuccessful attempts, it was synthesized independently and by two different routes by Eduard Linnemann and Carl Schorlemmer in 1868.Linnemann Eduard 1868 Ueber die Darstellung der Fettalkohole aus ihren Anfangsgliedern. Reduction des Essigsäure-Anhydrids zu Aethylalkohol https://books.google.com/books?id=3uRAAAAAYAAJ&pg=RA1-PA249 Justus Liebigs Annalen der Chemie de 148 2 249–251 10.1002/jlac.18681480216 1099-0690https://books.google.com/books?id=U18vAQAAMAAJ&pg=PA49 Zeitschrift für Chemie 1868 Quandt & Händel deSchorlemmer C. 1869 On the Derivatives of Propane (Hydride of Propyl) https://archive.org/details/philtrans04026594/mode/2up Proceedings of the Royal Society of London 17 372–376 10.1098/rspl.1868.0072 0370-1662 Occurrence Fusel alcohols like 1-Propanol are grain fermentation byproducts, and therefore trace amounts of 1-Propanol are present in many alcoholic beverages. Chemical properties thumb|left|450px|Some example reactions of 1-propanol1-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 n-propyl chloride. 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 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. 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.Ullmann's Encyclopedia of Industrial Chemistry Papa AJ Wiley-VCH 2011 9783527303854 Weinheim Propanols 10.1002/14356007.a22_173.pub2 H2C=CH2 + CO + H2 → CH3CH2CH=O CH3CH2CH=O + H2 → CH3CH2CH2OH Other proposed industrial processes include the two-step isomerization and hydrogenation of propylene oxide.Papa Anthony J. https://onlinelibrary.wiley.com/doi/book/10.1002/14356007 Ullmann's Encyclopedia of Industrial Chemistry 2000 Wiley 978-3-527-30385-4 1 243-254 en 10.1002/14356007 A traditional laboratory preparation of 1-propanol involves treating n-propyl iodide with moist Ag2O. 1-Propanol can also be prepared via the hydrogenation of acrolein with metal catalysts.Nayakasinghe Mindika Tilan Ponce Perez Rodrigo Chen Bo Takeuchi Noboru Zaera Francisco Adsorption, thermal conversion, and catalytic hydrogenation of acrolein on Cu surfaces Journal of Catalysis 1 October 2022 414 257–266 10.1016/j.jcat.2022.09.013 https://www.sciencedirect.com/science/article/pii/S002195172200389X 0021-9517 free Safety 1-Propanol is thought to be similar to ethanol in its effects on the human body, but 2 to 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.https://www.dir.ca.gov/dosh/doshreg/5155-Meetings/n-Propanol-Draft4-March-2-2011.pdf N-PROPANOL Health-Base Assessment and Recommendation for HEAC Unmack JL 2011 Due to a lack of long term data, the carcinogenicity of 1-propanol in humans is unknown. 1-Propanol as fuel 1-Propanol has a high octane number and is suitable for use as engine fuel. However, propanol is too expensive to use as a motor fuel. The research octane number (RON) of propanol is 118, and the anti-knock index (AKI) is 108.http://biofuel.org.uk/bioalcohols.html Bioalcohols 2010 Biofuel.org.uk 16 Apr 2014 16 April 2014 https://web.archive.org/web/20140416180242/http://biofuel.org.uk/bioalcohols.html dead References Further reading Lide DR 87th TF-CRC 2006 0849304873 CRC Handbook of Chemistry and Physics O'Neil MJ 14th Merck 2006 091191000X The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals Organic Chemistry W. & R. Chambers 1922 Perkin WH, Kipping FS London 0080223540 External links International Chemical Safety Card 0553 NIOSH Pocket Guide to Chemical Hazards Category:Alkanols Category:Alcohol solvents Category:Primary alcohols Category:GABAA receptor positive allosteric modulators Category:Sedatives Category:Hypnotics Category:Propyl compounds