1-Propanol

{{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{{cite book|title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)|vauthors=Favre HA, Powell WH|publisher=The Royal Society of Chemistry|year=2014|location=Cambridge|page=61|doi=10.1039/9781849733069|isbn=9780854041824}}

| 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

| Density = 0.803 g/mL

| MeltingPtK = 147

| BoilingPtK = 370 to 371

| LogP = 0.329

| VaporPressure = 1.99 kPa (at 20 °C)

| pKa = 16

| pKb = −2

| Solubility = miscible

| RefractIndex = 1.387

| Viscosity = 1.959 mPa·s (at 25 °C){{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=J. Chem. Thermodyn.|volume=40|issue=5|pages=818–828|doi=10.1016/j.jct.2008.01.008}}

| Dipole = 1.68 D

| MagSus = −45.176·10⁻⁶ cm³/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%

| PEL = TWA 200 ppm (500 mg/m³){{PGCH|0533}}

| IDLH = 800 ppm

| LD50 = 2800 mg/kg (rabbit, oral)
1699 mg/kg (mouse, oral)
1870 mg/kg (rat, oral){{IDLH|71238|n-Propyl alcohol}}

| REL = TWA 200 ppm (500 mg/m³) ST 250 ppm (625 mg/m³) [skin]

}}

| Section8 = {{Chembox Related

| OtherCompounds = Propane
Isopropyl alcohol
Propanamine
Ethanol
Butanol

}}

1-Propanol (also propan-1-ol, propanol, n-propyl alcohol) is a primary alcohol with the formula {{Chem2|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

The compound was discovered by Gustave Chancel in 1853 by fractional distillation of fusel oil.{{Cite EB1911 |wstitle=Propyl Alcohols |volume= 22 |page=450}} 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.{{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 }}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.{{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}}{{Cite book |url=https://books.google.com/books?id=U18vAQAAMAAJ&pg=PA49 |title=Zeitschrift für Chemie |date=1868 |publisher=Quandt & Händel |language=de}}{{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}}

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

File:Propanol reactions.png1-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 phosphorus trichloride with catalytic Zinc chloride gives n-propyl chloride. Reaction with acetic acid in the presence of an sulfuric acid 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 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 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.

{{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}}

{{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 with moist silver(I) oxide.

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.{{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}} 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.{{cite web |url=http://biofuel.org.uk/bioalcohols.html |title=Bioalcohols |date=2010 |website=Biofuel.org.uk |access-date=16 Apr 2014}}

References

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]

Category:Alkanols

Category:Alcohol solvents

Category:Primary alcohols

Category:GABAA receptor positive allosteric modulators

Category:Sedatives

Category:Hypnotics

Category:Propyl compounds