| Revision as of 16:45, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 476326307 of page 1-Propanol for the Chem/Drugbox validation project (updated: 'KEGG'). |
Latest revision as of 12:59, 11 October 2024 edit 138.75.252.65 (talk) →1-Propanol as fuel |
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{{short description|Primary alcohol compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 455165561 |
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| verifiedrevid = 477208553 |
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| ImageFile = Propan-1-ol.svg |
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| ImageName = Skeletal formula of 1-propanol |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| Name = 1-Propanol |
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| ImageSize = 100 |
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| pronounce = ˈprəʊpən.wən.ɒl |
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| ImageName = Skeletal formula of 1-propanol |
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| ImageFileL1 = Propan-1-ol-2D-flat.png |
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| ImageFile = Propan-1-ol.svg |
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| ImageName1 = Ball and stick model of 1-propanol |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFile1 = Propan-1-ol-3D-balls.png |
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| ImageNameL1 = Skeletal formula of 1-propanol with all explicit hydrogens added |
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| 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=]|year=2014|location=Cambridge|page=61|doi=10.1039/9781849733069|isbn=9780854041824}}</ref> |
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| ImageFileR1 = Propan-1-ol-3D-balls.png |
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| SystematicName = |
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| ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| OtherNames = {{unbulleted list|''n''-Propyl alcohol|''n''-Propanol|''n''-PrOH|Ethyl carbinol|1-Hydroxypropane|Propionic alcohol|Propionyl alcohol|Propionylol|Propyl alcohol|Propylic alcohol|Propylol}} |
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| ImageNameR1 = Ball and stick model of 1-propanol |
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| IUPACName = |
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| IUPACName = Propan-1-ol<ref>{{Cite web|title = 1-Propanol - Compound Summary|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1031|work = PubChem Compound|publisher = National Center for Biotechnology Information|accessdate = 10 October 2011|location = USA|date = 26 March 2005|at = Identification and Related Records}}</ref> |
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| data page pagename = 1-Propanol (data page) |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| CASNo = 71-23-8 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 71-23-8 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 1031 |
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| PubChem = 1031 |
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| ChemSpiderID = 1004 |
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| PubChem_Ref = {{Pubchemcite|correct|PubChem}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 1004 |
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| UNII = 96F264O9SV |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 96F264O9SV |
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| EINECS = 200-746-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| EINECS = 200-746-9 |
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| UNNumber = 1274 |
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| UNNumber = 1274 |
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| DrugBank = DB03175 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB03175 |
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| KEGG = C05979 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = <!-- blanked - oldvalue: C05979 --> |
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| MeSHName = 1-Propanol |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| MeSHName = 1-Propanol |
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| ChEBI = 28831 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 28831 |
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| ChEMBL = 14687 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 14687 |
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| RTECS = UH8225000 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| RTECS = UH8225000 |
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| Beilstein = 1098242 |
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| Beilstein = 1098242 |
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| Gmelin = 25616 |
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| Gmelin = 25616 |
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| 3DMet = B00883 |
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| 3DMet = B00883 |
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| SMILES = CCCO |
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| StdInChI = 1S/C3H7OH/c1-2-3-4/h4H,2-3H2,1H3 |
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| SMILES = CCCO |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C3H8O/c1-2-3-4/h4H,2-3H2,1H3 |
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| StdInChIKey = BDERNNFJNOPAEC-UHFFFAOYSA-N |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = BDERNNFJNOPAEC-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| ATCCode_prefix = D08 |
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| ATCCode_suffix = AX03 |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C = 3 |
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| C=3 | H=8 | O=1 |
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| Appearance = Colorless liquid |
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| H = 8 |
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| Odor = mild, alcohol-like<ref name=PGCH/> |
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| O = 1 |
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| Density = 0.803 g/mL |
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| or |
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| MeltingPtK = 147 |
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| ExactMass = 60.057514878 g mol<sup>−1</sup> |
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| BoilingPtK = 370 to 371 |
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| Appearance = Colorless liquid |
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| LogP = 0.329 |
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| Density = 803.4 mg cm<sup>−3</sup> |
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| VaporPressure = 1.99 kPa (at 20 °C) |
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| MeltingPtK = 147 |
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| BoilingPtKL = 370 |
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| pKa = 16 |
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| BoilingPtKH = 371 |
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| pKb = −2 |
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| Solubility = ] |
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| LogP = 0.329 |
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| RefractIndex = 1.387 |
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| VaporPressure = 1.99 kPa (at 20 °C) |
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| Viscosity = 1.959 mPa·s (at 25 °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=]|volume=40|issue=5|pages=818–828|doi=10.1016/j.jct.2008.01.008}}</ref> |
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| pKa = 16 |
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| pKb = −2 |
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| Dipole = 1.68 D |
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| MagSus = −45.176·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| RefractIndex = 1.387 |
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| Viscosity = 1.938 mPa s |
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| Dipole = 1.68 D |
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}} |
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}} |
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| Section3 = {{Chembox Thermochemistry |
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| Section3 = |
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| Section4 = |
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| DeltaHf = −302.79–−302.29 kJ mol<sup>-1</sup> |
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| Section5 = {{Chembox Thermochemistry |
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| DeltaHc = −2.02156–−2.02106 MJ mol<sup>-1</sup> |
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| DeltaHf = −302.79…−302.29 kJ/mol |
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| Entropy = 192.8 J K<sup>−1</sup> mol<sup>−1</sup> |
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| DeltaHc = −2.02156…−2.02106 MJ/mol |
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| HeatCapacity = 143.96 J K<sup>−1</sup> mol<sup>−1</sup> |
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| Entropy = 192.8 J/(K·mol) |
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| HeatCapacity = 143.96 J/(K·mol) |
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}} |
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| Section4 = {{Chembox Hazards |
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| Section6 = {{Chembox Pharmacology |
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| ATCCode_prefix = D08 |
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| GHSPictograms = {{GHS flame}} {{GHS corrosion}} {{GHS exclamation mark}} |
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| ATCCode_suffix = AX03 |
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| GHSSignalWord = '''DANGER''' |
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| HPhrases = {{H-phrases|225|318|336}} |
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| PPhrases = {{P-phrases|210|261|280|305+351+338}} |
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| EUIndex = 603-003-00-0 |
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| EUClass = {{Hazchem F}} {{Hazchem Xi}} |
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| RPhrases = {{R11}}, {{R41}}, {{R67}} |
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| SPhrases = {{S2}}, {{S7}}, {{S16}}, {{S24}}, {{S26}}, {{S39}} |
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| NFPA-H = 1 |
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| NFPA-F = 3 |
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| NFPA-R = 0 |
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| FlashPt = 22 °C |
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| Autoignition = 371 °C |
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| ExploLimits = 13.7% |
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}} |
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}} |
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| Section8 = {{Chembox Related |
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| Section7 = {{Chembox Hazards |
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| MainHazards = Flammable liquid |
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| OtherCpds = ]<br /> |
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| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}} |
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] |
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| GHSSignalWord = '''DANGER''' |
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| HPhrases = {{H-phrases|225|302|318|336}} |
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| PPhrases = {{P-phrases|210|261|280|305+351+338}} |
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| NFPA-H = 1 |
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| NFPA-F = 3 |
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| NFPA-R = 0 |
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| FlashPtC = 22 |
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| AutoignitionPtC = 371 |
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| ExploLimits = 2.2–13.7%<ref name=PGCH/> |
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| PEL = TWA 200 ppm (500 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0533}}</ref> |
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| IDLH = 800 ppm<ref name=PGCH/> |
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| 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> |
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| REL = TWA 200 ppm (500 mg/m<sup>3</sup>) ST 250 ppm (625 mg/m<sup>3</sup>) <ref name=PGCH/> |
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}} |
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| Section8 = {{Chembox Related |
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| OtherCompounds = ]<br />]<br />]<br />]<br />] |
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'''1-Propanol''' (also '''propan-1-ol''', '''propanol''', '''n-propyl alcohol''') is a ] with the formula {{Chem2|CH3CH2CH2OH}} and sometimes ] as '''PrOH''' or '''''n''-PrOH'''. It is a colourless liquid and an ] of ]. 1-Propanol is used as a ] in the pharmaceutical industry, mainly for ]s and ] esters, and, sometimes, as a ] agent. |
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==Occurrence== |
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]s like 1-Propanol are grain fermentation byproducts, and therefore trace amounts of 1-Propanol are present in ]. |
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==Chemical properties== |
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]1-Propanol shows the normal reactions of a ]. Thus it can be converted to ]; for example red ] and ] produce ] in 80% yield, while ] with catalytic ] gives ]. Reaction with ] in the presence of an ] catalyst under ] conditions gives ], while refluxing propanol overnight with formic acid alone can produce propyl formate in 65% yield. Oxidation of 1-propanol with ] and {{Chem2|H2SO4}} gives a 36% yield of ], and therefore for this type of reaction higher yielding methods using ] or the ] are recommended. Oxidation with ] yields ]. |
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==Preparation== |
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1-Propanol is manufactured by catalytic ] of ]. Propionaldehyde is produced via the ] by ] of ] using ] and ] in the presence of a catalyst such as ] or a ] complex.<ref> |
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{{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> |
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{{block indent|{{Chem2|1=H2C=CH2 + CO + H2 → CH3CH2CH=O}}}} |
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{{block indent|{{Chem2|1=CH3CH2CH=O + H2 → CH3CH2CH2OH}}}} |
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A traditional laboratory preparation of 1-propanol involves treating ] with moist ]. |
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==Safety== |
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1-Propanol is thought to be similar to ] 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 g/kg for ethanol). It is metabolized into ]. Effects include ] and ]. 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. |
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==1-Propanol as fuel== |
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1-Propanol has a high ] and is suitable for use as ] fuel. However, propanol is too expensive to use as a motor fuel. The ] (RON) of propanol is 118, and the ] (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> |
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==References== |
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{{Reflist}} |
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==Further reading== |
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# {{vogelOrganic}} |
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# {{Cite book|veditors=Lide DR|edition=87th|publisher=TF-CRC|year=2006|isbn=0849304873|title=CRC Handbook of Chemistry and Physics}} |
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# {{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}} |
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# {{Cite book|title=Organic Chemistry|publisher=W. & R. Chambers|year=1922|vauthors=Perkin WH, Kipping FS|location=London|isbn=0080223540}} |
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==External links== |
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{{Alcohols}} |
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{{Antiseptics and disinfectants}} |
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{{Sedatives}} |
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{{GABAAR PAMs}} |
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{{DEFAULTSORT:Propanol, 1-}} |
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