View source for Chemistry:1-Pentanol

{{Chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 477208509
|ImageFile1 = Pentan-1-ol-2D-skeletal.png
|ImageFile1_Ref = {{chemboximage|correct|??}}
|ImageSize1 = 100
|ImageName1 = Skeletal formula of 1-pentanol
|ImageFile2 = Pentan-1-ol-3D-balls.png
|ImageFile2_Ref = {{chemboximage|correct|??}}
|ImageSize2 = 100
|ImageName2 = Ball and stick model of 1-pentanol
|PIN = Pentan-1-ol<ref>{{Cite web|title = n-pentanol - Compound Summary|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6276&loc=ec_rcs|work = PubChem Compound|publisher = National Center for Biotechnology Information|access-date = 10 October 2011|location = USA|date = 26 March 2005|at = Identification and Related Records}}</ref>
|Section1={{Chembox Identifiers
|CASNo = 71-41-0
|CASNo_Ref = {{cascite|correct|CAS}}
|PubChem = 6276
|ChemSpiderID = 6040
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|UNII = M9L931X26Y
|UNII_Ref = {{fdacite|correct|FDA}}
|EINECS = 200-752-1
|UNNumber = 1105
|KEGG = C16834
|KEGG_Ref = {{keggcite|changed|kegg}}
|MeSHName = n-Pentanol
|ChEBI = 44884
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 14568
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|RTECS = SB9800000
|Beilstein = 1730975
|Gmelin = 25922
|SMILES = CCCCCO
|StdInChI = 1S/C5H12O/c1-2-3-4-5-6/h6H,2-5H2,1H3
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = AMQJEAYHLZJPGS-UHFFFAOYSA-N
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
|C=5 | H=12 | O=1
|Density = 0.811 g cm<sup>−3</sup>
|MeltingPtK = 195
|BoilingPtK = 410 to 412
|Solubility = 22 g L<sup>−1</sup>
|LogP = 1.348
|VaporPressure = 200 Pa (at 20&nbsp;°C)
|RefractIndex = 1.409
|MagSus = -67.7·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
|Section3={{Chembox Thermochemistry
|DeltaHf = −351.90–−351.34 kJ mol<sup>−1</sup>
|DeltaHc = −3331.19–−3330.63 kJ mol<sup>−1</sup>
|Entropy = 258.9 J K<sup>−1</sup> mol<sup>−1</sup>
|HeatCapacity = 207.45 J K<sup>−1</sup> mol<sup>−1</sup>
}}
|Section4={{Chembox Hazards
|GHSPictograms = {{GHS flame}} {{GHS exclamation mark}}
|GHSSignalWord = '''WARNING'''
|HPhrases = {{H-phrases|226|315|332|335}}
|PPhrases = {{P-phrases|261}}
|NFPA-H = 1
|NFPA-F = 2
|NFPA-R = 0
|FlashPtC = 49
|AutoignitionPtC = 300
}}
|Section5={{Chembox Related
|OtherCompounds = [[Chemistry:Hexane|Hexane]]<br />
Pentylamine
}}
}}

'''1-Pentanol''', (or '''''n''-pentanol''', '''pentan-1-ol'''), is an [[Chemistry:Organic compound|organic compound]] with the formula {{chem2|CH3CH2CH2CH2CH2OH}} and is classified as a [[Chemistry:Primary alcohol|primary alcohol]].<ref name=crc>[[Physics:CRC Handbook of Chemistry and Physics|CRC Handbook of Chemistry and Physics]] 65th ed.</ref> It is a colourless [[Physics:Liquid|liquid]] with a distinctive aroma. It is one of 8 isomeric alcohols with the formula {{chem2|C5H11OH}}. It is used as a solvent, a biological drying agent and in the synthesis of some fragrance compounds. It is also a common component of [[Chemistry:Fusel alcohol|fusel alcohol]]s (fusel oils), the undesirable byproducts of [[Chemistry:Ethanol fermentation|alcoholic fermentation]].

==Preparation==
1-Pentanol is prepared from [[Chemistry:1-Butene|1-butene]] by [[Chemistry:Hydroformylation|hydroformylation]] followed by [[Chemistry:Hydrogenation|hydrogenation]] of the resulting [[Chemistry:Pentanal|pentanal]].<ref name=ull>{{cite book |doi=10.1002/14356007.a19_049.pub2 |chapter=Pentanols |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2011 |last1=Lappe |first1=Peter |last2=Hofmann |first2=Thomas |isbn=9783527303854 }}</ref>
:{{chem2|CH3CH2CH\dCH2  +  CO  +  H2  ->  CH3CH2CH2CH2CHO}}
:{{chem2|CH3CH2CH2CH2CHO  +  H2  ->  CH3CH2CH2CH2CH2OH}}

Pentanol can be prepared by [[Fractional distillation|fractional distillation]] of fusel oil. To reduce the use of fossil fuels, research is underway to develop cost-effective methods of producing (chemically identical) bio-pentanol with [[Biology:Fermentation|fermentation]].<ref>{{Cite journal |last1=Cann |first1=Anthony F. |last2=Liao |first2=James C. |date=2010-01-01 |title=Pentanol isomer synthesis in engineered microorganisms |url=https://doi.org/10.1007/s00253-009-2262-7 |journal=Applied Microbiology and Biotechnology |language=en |volume=85 |issue=4 |pages=893–899 |doi=10.1007/s00253-009-2262-7 |issn=1432-0614 |pmc=2804790 |pmid=19859707}}</ref><ref>{{Cite thesis |title=Production of pentanol in metabolically engineered ''Escherichia coli'' |url=https://dspace.mit.edu/handle/1721.1/65767 |publisher=Massachusetts Institute of Technology |date=2011 |degree=Thesis |first=Hsien-Chung |last=Tseng|hdl=1721.1/65767 }}</ref>

==Uses and occurrence==
The [[Chemistry:Hydroxyl group|hydroxyl group]] (OH) is the active site of many reactions. The [[Chemistry:Ester|ester]] formed from 1-pentanol and [[Chemistry:Butyric acid|butyric acid]] is [[Chemistry:Pentyl butyrate|pentyl butyrate]], which has an [[Biology:Apricot|apricot]]-like odor. The ester formed from 1-pentanol and [[Chemistry:Acetic acid|acetic acid]] is [[Chemistry:Amyl acetate|amyl acetate]] (also called pentyl acetate), which has a [[Biology:Banana|banana]]-like odor.

It is a precursor to dipentyl [[Chemistry:Zinc dithiophosphate|zinc dithiophosphate]]s, which are used in froth flotation.<ref name=ull/>

In 2014, a study was conducted comparing the performance of [[Chemistry:Diesel fuel|diesel fuel]] blends with various proportions of pentanol as an additive. While gaseous emissions increased with higher concentrations of pentanol, particulate emissions decreased.<ref name=cheung>Wei, Liangjie & Cheung, C.s & Huang, Zuohua. (2014). Effect of n-pentanol addition on the combustion, performance and emission characteristics of a direct-injection diesel engine. Energy. 70. 10.1016/j.energy.2014.03.106.</ref>

Pentanol is of used as a [[Physics:Solvent|solvent]].

==References==
{{Reflist|}}

{{Alcohols}}
{{Sedatives}}
{{GABAAR PAMs}}

{{DEFAULTSORT:Pentanol, 1-}}

[[Category:Alkanols]]
[[Category:Primary alcohols]]
[[Category:GABAA receptor positive allosteric modulators]]
[[Category:Sedatives]]
[[Category:Hypnotics]]

{{Sourceattribution|1-Pentanol}}