View source for 1-Propanol

{{short description|Primary alcohol compound}}
{{Chembox
| Verifiedfields = changed
| Watchedfields  = changed
| verifiedrevid  = 477208553
| ImageName      = Skeletal formula of 1-propanol
| Name           = 1-Propanol
| pronounce      = {{IPAc-en|ˈ|p|r|ə|ʊ|p|ə|n|.|w|ə|n|.|ɒ|l}}
| ImageFile      = Propan-1-ol.svg
| ImageName1     = Ball and stick model of 1-propanol
| ImageFile1     = Propan-1-ol-3D-balls.png
| PIN            = Propan-1-ol<ref>{{cite book|title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)|vauthors=Favre HA, Powell WH|publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]]|year=2014|location=Cambridge|page=61|doi=10.1039/9781849733069|isbn=9780854041824}}</ref>
| SystematicName = 
| OtherNames     = {{unbulleted list|''n''-Propyl alcohol|''n''-Propanol|''n''-PrOH|Ethyl carbinol|1-Hydroxypropane|Propionic alcohol|Propionyl alcohol|Propionylol|Propyl alcohol|Propylic alcohol|Propylol}}
| IUPACName      = 
| data page pagename = 1-Propanol (data page)
| Section1       = {{Chembox Identifiers
| CASNo = 71-23-8
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 1031
| ChemSpiderID = 1004
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII = 96F264O9SV
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 200-746-9
| UNNumber = 1274
| DrugBank = DB03175
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| KEGG = C05979
| KEGG_Ref = {{keggcite|correct|kegg}}
| MeSHName = 1-Propanol
| ChEBI = 28831
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 14687
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = UH8225000
| Beilstein = 1098242
| Gmelin = 25616
| 3DMet = B00883
| SMILES = CCCO
| StdInChI = 1S/C3H7OH/c1-2-3-4/h4H,2-3H2,1H3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BDERNNFJNOPAEC-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
| Section2       = {{Chembox Properties
| C=3 | H=8 | O=1
| Appearance = Colorless liquid
| Odor = mild, alcohol-like<ref name=PGCH/>
| Density = 0.803 g/mL
| MeltingPtK = 147
| BoilingPtK = 370 to 371
| LogP = 0.329
| VaporPressure = 1.99 kPa (at 20&nbsp;°C)
| pKa = 16
| pKb = −2
| Solubility = [[miscible]]
| RefractIndex = 1.387
| Viscosity = 1.959 mPa·s (at 25&nbsp;°C)<ref>{{cite journal|vauthors=Pal A, Gaba R|year=2008|title=Volumetric, acoustic, and viscometric studies of molecular interactions in binary mixtures of dipropylene glycol dimethyl ether with 1-alkanols at 298.15 K|journal=[[The Journal of Chemical Thermodynamics|J. Chem. Thermodyn.]]|volume=40|issue=5|pages=818–828|doi=10.1016/j.jct.2008.01.008|bibcode=2008JChTh..40..818P }}</ref>
| Dipole = 1.68 D
| MagSus = −45.176·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
| Section3       = 
| Section4       = 
| Section5       = {{Chembox Thermochemistry
| DeltaHf = −302.79…−302.29 kJ/mol
| DeltaHc = −2.02156…−2.02106 MJ/mol
| Entropy = 192.8 J/(K·mol)
| HeatCapacity = 143.96 J/(K·mol)
}}
| Section6       = {{Chembox Pharmacology
| ATCCode_prefix = D08
| ATCCode_suffix = AX03
}}
| Section7       = {{Chembox Hazards
| MainHazards = Flammable liquid 
| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}}
| GHSSignalWord = '''DANGER'''
| HPhrases = {{H-phrases|225|302|318|336}}
| PPhrases = {{P-phrases|210|261|280|305+351+338}}
| NFPA-H = 1
| NFPA-F = 3
| NFPA-R = 0
| FlashPtC = 22
| AutoignitionPtC = 371
| ExploLimits = 2.2–13.7%<ref name=PGCH/>
| PEL = TWA 200 ppm (500 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0533}}</ref>
| IDLH = 800 ppm<ref name=PGCH/>
| LD50 = 2800 mg/kg (rabbit, oral)<br/>1699 mg/kg (mouse, oral)<br/>1870 mg/kg (rat, oral)<ref>{{IDLH|71238|n-Propyl alcohol}}</ref>
| REL = TWA 200 ppm (500 mg/m<sup>3</sup>) ST 250 ppm (625 mg/m<sup>3</sup>) [skin]<ref name=PGCH/>
}}
| Section8       = {{Chembox Related
| OtherCompounds = [[Propane]]<br />[[Isopropyl alcohol]]<br />[[Propanamine]]<br />[[Ethanol]]<br />[[Butanol]]
 }}
}}

'''1-Propanol''' (also '''propan-1-ol''', '''propanol''', '''n-propyl alcohol''') is a [[primary alcohol]] with the formula {{Chem2|CH3CH2CH2OH}} and sometimes [[skeletal formula#Pseudoelement symbols|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 [[resin]]s and [[cellulose]] esters, and, sometimes, as a [[Disinfectant|disinfecting]] agent.

== History ==
{{Section-stub|date=January 2025}}
The compound was discovered by [[Gustave Chancel]] in 1853 by [[fractional distillation]] of [[fusel oil]].<ref>{{Cite EB1911 |wstitle=Propyl Alcohols |volume= 22 |page=450}}</ref> 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 acid|propionic]] alcohol''' and '''hydrate of trityl'''.<ref>{{Cite journal |last=Wisniak |first=Jaime |date=2013 |title=Gustav Charles Bonaventure Chancel |journal=Educación Química |volume=24 |issue=1 |pages=23–30 |doi=10.1016/S0187-893X(13)73191-4 |issn=0187-893X|doi-access=free }}</ref><ref>[[s:fr:Page:Comptes rendus hebdomadaires des séances de l’Académie des sciences, tome 037, 1853.djvu/414]]</ref>

After several unsuccessful attempts, it was synthesized independently and by two different routes by [[Eduard Linnemann]] and [[Carl Schorlemmer]] in 1868.<ref>{{Cite journal |last=Linnemann |first=Eduard |date=1868 |title=Ueber die Darstellung der Fettalkohole aus ihren Anfangsgliedern. Reduction des Essigsäure-Anhydrids zu Aethylalkohol |url=https://books.google.com/books?id=3uRAAAAAYAAJ&pg=RA1-PA249 |journal=Justus Liebigs Annalen der Chemie |language=de |volume=148 |issue=2 |pages=249–251 |doi=10.1002/jlac.18681480216 |issn=1099-0690}}</ref><ref>{{Cite book |url=https://books.google.com/books?id=U18vAQAAMAAJ&pg=PA49 |title=Zeitschrift für Chemie |date=1868 |publisher=Quandt & Händel |language=de}}</ref><ref>{{Cite journal |last=Schorlemmer |first=C. |date=1869 |title=On the Derivatives of Propane (Hydride of Propyl) |url=https://archive.org/details/philtrans04026594/mode/2up |journal=Proceedings of the Royal Society of London |volume=17 |pages=372–376 |doi=10.1098/rspl.1868.0072 |issn=0370-1662}}</ref>

==Occurrence==
[[Fusel alcohol]]s like 1-Propanol are grain fermentation byproducts, and therefore trace amounts of 1-Propanol are present in [[comparison of psychoactive alcohols in alcoholic drinks|many alcoholic beverages]].

==Chemical properties==
[[File:Propanol reactions.png|thumb|left|450px|Some example reactions of 1-propanol]]1-Propanol shows the normal reactions of a [[primary alcohol]]. Thus it can be converted to [[Haloalkane|alkyl halides]]; for example red [[phosphorus]] and [[iodine]] produce [[n-propyl iodide]] in 80% yield, while [[phosphorus trichloride|{{Chem2|PCl3}}]] with catalytic [[Zinc chloride|{{Chem2|ZnCl2}}]] gives [[n-propyl chloride]]. Reaction with [[acetic acid]] in the presence of an [[sulfuric acid|{{Chem2|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 [[Sodium dichromate|{{Chem2|Na2Cr2O7}}]] and {{Chem2|H2SO4}} gives a 36% yield of [[propionaldehyde]], and therefore for this type of reaction higher yielding methods using [[Pyridinium chlorochromate|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 [[dicobalt octacarbonyl|cobalt octacarbonyl]] or a [[rhodium]] complex.<ref>
{{Cite book|title=Ullmann's Encyclopedia of Industrial Chemistry|vauthors=Papa AJ|publisher=Wiley-VCH|year=2011|isbn=9783527303854|location=Weinheim|chapter=Propanols|doi=10.1002/14356007.a22_173.pub2}}</ref>

{{block indent|{{Chem2|1=H2C=CH2 + CO + H2 → CH3CH2CH=O}}}}
{{block indent|{{Chem2|1=CH3CH2CH=O + H2 → CH3CH2CH2OH}}}}

A traditional laboratory preparation of 1-propanol involves treating [[N-Propyl iodide|''n''-propyl iodide]] with moist [[silver(I) oxide|{{Chem2|Ag2O}}]].

==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 LD<sub>50</sub> ranging from 1.9 g/kg to 6.5 g/kg (compared to 7.06&nbsp;g/kg for ethanol). It is metabolized into [[propionic acid]]. Effects include [[Alcohol intoxication|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.<ref>{{cite web|url=https://www.dir.ca.gov/dosh/doshreg/5155-Meetings/n-Propanol-Draft4-March-2-2011.pdf|title=N-PROPANOL Health-Base Assessment and Recommendation for HEAC|last=Unmack JL|date=2011}}</ref> 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 [[Internal combustion engine|engine]] fuel. However, propanol is too expensive to use as a motor fuel. The [[Octane number#RON|research octane number]] (RON) of propanol is 118, and the [[Octane number#AKI|anti-knock index]] (AKI) is 108.<ref>{{cite web |url=http://biofuel.org.uk/bioalcohols.html |title=Bioalcohols |date=2010 |website=Biofuel.org.uk |access-date=16 Apr 2014}}</ref>

==References==
{{Reflist}}

==Further reading==
# {{vogelOrganic}}
# {{Cite book|veditors=Lide DR|edition=87th|publisher=TF-CRC|year=2006|isbn=0849304873|title=CRC Handbook of Chemistry and Physics}}
# {{Cite book|veditors=O'Neil MJ|edition=14th|publisher=Merck|year=2006|isbn=091191000X|title=The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals}}
# {{Cite book|title=Organic Chemistry|publisher=W. & R. Chambers|year=1922|vauthors=Perkin WH, Kipping FS|location=London|isbn=0080223540}}

==External links==
* [http://www.inchem.org/documents/icsc/icsc/eics0553.htm International Chemical Safety Card 0553]
* [https://www.cdc.gov/niosh/npg/npgd0533.html NIOSH Pocket Guide to Chemical Hazards]

{{Alcohols}}
{{Antiseptics and disinfectants}}
{{Sedatives}}
{{GABAAR PAMs}}

{{DEFAULTSORT:Propanol, 1-}}
[[Category:Alkanols]]
[[Category:Alcohol solvents]]
[[Category:Primary alcohols]]
[[Category:GABAA receptor positive allosteric modulators]]
[[Category:Sedatives]]
[[Category:Hypnotics]]
[[Category:Propyl compounds]]