View source for Chemistry:1-Propanol

{{short description|Primary alcohol compound}}
{{Chembox
| Verifiedfields = changed
| Watchedfields  = changed
| verifiedrevid  = 477208553
| ImageName      = Skeletal formula of 1-propanol
| Name           = 1-Propanol
| pronounce      = ˈprəʊpən.wən.ɒl
| 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=[[Organization: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 = [[Chemistry:Miscible|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=[[Chemistry:The Journal of Chemical Thermodynamics|J. Chem. Thermodyn.]]|volume=40|issue=5|pages=818–828|doi=10.1016/j.jct.2008.01.008}}</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 = [[Chemistry:Propane|Propane]]<br />[[Chemistry:Isopropyl alcohol|Isopropyl alcohol]]<br />Propanamine<br />[[Chemistry:Ethanol|Ethanol]]<br />[[Chemistry:Butanol|Butanol]]
 }}
}}

'''1-Propanol''' (also '''propan-1-ol''', '''propanol''', '''n-propyl alcohol''') is a [[Chemistry:Primary alcohol|primary alcohol]] with the formula {{Chem2|CH3CH2CH2OH}} and sometimes [[Chemistry:Skeletal formula#Pseudoelement symbols|represented]] as '''PrOH''' or '''''n''-PrOH'''. It is a colourless liquid and an [[Chemistry:Isomer|isomer]] of 2-propanol. It is formed naturally in small amounts during many fermentation processes and used as a [[Physics:Solvent|solvent]] in the pharmaceutical industry, mainly for resins and [[Chemistry:Cellulose|cellulose]] esters, and, sometimes, as a [[Chemistry:Disinfectant|disinfecting]] agent.

==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 alkyl halides; for example red phosphorus and iodine produce n-propyl iodide in 80% yield, while {{Chem2|PCl3}} with catalytic {{Chem2|ZnCl2}} gives n-propyl chloride. Reaction with acetic acid in the presence of an {{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 {{Chem2|Na2Cr2O7}} and {{Chem2|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 [[Chemistry:Propionic acid|propionic acid]].

==Preparation==
1-Propanol is manufactured by catalytic [[Chemistry:Hydrogenation|hydrogenation]] of [[Chemistry:Propionaldehyde|propionaldehyde]]. Propionaldehyde is produced via the oxo process by [[Chemistry:Hydroformylation|hydroformylation]] of [[Chemistry:Ethylene|ethylene]] using [[Chemistry:Carbon monoxide|carbon monoxide]] and [[Chemistry:Hydrogen|hydrogen]] in the presence of a catalyst such as [[Chemistry:Dicobalt octacarbonyl|cobalt octacarbonyl]] or a [[Chemistry:Rhodium|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>

:{{Chem2|1=H2C=CH2 + CO + H2 → CH3CH2CH=O}}

:{{Chem2|1=CH3CH2CH=O + H2 → CH3CH2CH2OH}}

A traditional laboratory preparation of 1-propanol involves treating [[Chemistry:N-Propyl iodide|''n''-propyl iodide]] with moist {{Chem2|Ag2O}}.

==Safety==
1-Propanol is thought to be similar to [[Chemistry:Ethanol|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 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 [[Chemistry:Propionic acid|propionic acid]]. Effects include [[Medicine:Alcohol intoxication|alcoholic intoxication]] and [[Medicine:High anion gap metabolic acidosis|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 lack of long term data, the carcinogenicity of 1-propanol in human beings is unknown.

==1-Propanol as fuel==
1-Propanol has high octane number and is suitable for [[Earth:Internal combustion engine|engine]] fuel usage. However, propanol is too expensive to use as a motor fuel. The research octane number (RON) of propanol is 118, and 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==
# {{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]]

{{Sourceattribution|1-Propanol}}