1-Pentanol
{{Chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 477208509
|ImageFile1 = Pentan-1-ol-2D-skeletal.png
|ImageFile1_Ref = {{chemboximage|correct|??}}
|ImageSize1 = 250
|ImageName1 = Skeletal formula of 1-pentanol
|ImageFile2 = Pentan-1-ol-3D-balls.png
|ImageFile2_Ref = {{chemboximage|correct|??}}
|ImageSize2 = 250
|ImageName2 = Ball and stick model of 1-pentanol
|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−3
|MeltingPtK = 195
|BoilingPtK = 410 to 412
|Solubility = 22 g L−1
|LogP = 1.348
|VaporPressure = 200 Pa (at 20 °C)
|RefractIndex = 1.409
|MagSus = −67.7·10−6 cm3/mol
}}
|Section3={{Chembox Thermochemistry
|DeltaHf = −351.90–−351.34 kJ mol−1
|DeltaHc = −3331.19–−3330.63 kJ mol−1
|Entropy = 258.9 J K−1 mol−1
|HeatCapacity = 207.45 J K−1 mol−1
}}
|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 = Hexane
}}
}}
1-Pentanol, (or n-pentanol, pentan-1-ol), is an organic compound with the formula {{chem2|CH3CH2CH2CH2CH2OH}} and is classified as a primary alcohol.CRC Handbook of Chemistry and Physics 65th ed. It is a colourless 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 fusel alcohols (fusel oils), the undesirable byproducts of alcoholic fermentation.
Preparation
1-Pentanol is prepared from 1-butene by hydroformylation followed by hydrogenation of the resulting pentanal.{{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 }}
:{{chem2|CH3CH2CH\dCH2 + CO + H2 -> CH3CH2CH2CH2CHO}}
:{{chem2|CH3CH2CH2CH2CHO + H2 -> CH3CH2CH2CH2CH2OH}}
Pentanol can be prepared by 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 fermentation.{{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}}{{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 }}
Uses and occurrence
The hydroxyl group (OH) is the active site of many reactions. The ester formed from 1-pentanol and butyric acid is pentyl butyrate, which has an apricot-like odor. The ester formed from 1-pentanol and acetic acid is amyl acetate (also called pentyl acetate), which has a banana-like odor.
It is a precursor to dipentyl zinc dithiophosphates, which are used in froth flotation.
In 2014, a study was conducted comparing the performance of diesel fuel blends with various proportions of pentanol as an additive. While gaseous emissions increased with higher concentrations of pentanol, particulate emissions decreased.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.
Pentanol is often used as a solvent.
References
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