1-Pentanol

1-Pentanol

Skeletal formula of 1-pentanol
Ball and stick model of 1-pentanol
Names
Preferred IUPAC name Pentan-1-ol [1]
Identifiers
CAS Number	71-41-0  Y
3D model (JSmol)	Interactive image
Beilstein Reference	1730975
ChEBI	CHEBI:44884  Y
ChEMBL	ChEMBL14568  Y
ChemSpider	6040  Y
ECHA InfoCard	100.000.684
EC Number	200-752-1
Gmelin Reference	25922
KEGG	C16834  N
MeSH	n-Pentanol
PubChem CID	6276
RTECS number	SB9800000
UNII	M9L931X26Y  Y
UN number	1105
CompTox Dashboard (EPA)	DTXSID6021741
InChI InChI=1S/C5H12O/c1-2-3-4-5-6/h6H,2-5H2,1H3 Y Key: AMQJEAYHLZJPGS-UHFFFAOYSA-N Y
SMILES CCCCCO
Properties
Chemical formula	C5H12O
Molar mass	88.150 g·mol−1
Density	0.811 g cm−3
Melting point	−78 °C; −109 °F; 195 K
Boiling point	137 to 139 °C; 278 to 282 °F; 410 to 412 K
Solubility in water	22 g L−1
log P	1.348
Vapor pressure	200 Pa (at 20 °C)
Magnetic susceptibility (χ)	−67.7·10−6 cm3/mol
Refractive index (nD)	1.409
Thermochemistry
Heat capacity (C)	207.45 J K−1 mol−1
Std molar entropy (S⦵298)	258.9 J K−1 mol−1
Std enthalpy of formation (ΔfH⦵298)	−351.90–−351.34 kJ mol−1
Std enthalpy of combustion (ΔcH⦵298)	−3331.19–−3330.63 kJ mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H315, H332, H335
Precautionary statements	P261
NFPA 704 (fire diamond)	1 2 0
Flash point	49 °C (120 °F; 322 K)
Autoignition temperature	300 °C (572 °F; 573 K)
Related compounds
Related compounds	Hexane Pentylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

1-Pentanol, (or n-pentanol, pentan-1-ol), is an organic compound with the formula CH₃CH₂CH₂CH₂CH₂OH and is classified as a primary alcohol. ^[2] It is a colourless liquid with a distinctive aroma. It is one of 8 isomeric alcohols with the formula 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. ^[3]

CH₃CH₂CH=CH₂ + CO + H₂ → CH₃CH₂CH₂CH₂CHO

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. ^{[4] [5]}

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. ^[3]

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. ^[6]

Pentanol is often used as a solvent.

References

1. "n-pentanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 10 October 2011.
2. CRC Handbook of Chemistry and Physics 65th ed.
3. Lappe, Peter; Hofmann, Thomas (2011). "Pentanols". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a19_049.pub2. ISBN   9783527303854.
4. Cann, Anthony F.; Liao, James C. (2010-01-01). "Pentanol isomer synthesis in engineered microorganisms". Applied Microbiology and Biotechnology. 85 (4): 893–899. doi:10.1007/s00253-009-2262-7. ISSN   1432-0614. PMC   2804790 . PMID   19859707.
5. Tseng, Hsien-Chung (2011). Production of pentanol in metabolically engineered Escherichia coli (Thesis thesis). Massachusetts Institute of Technology. hdl:1721.1/65767.
6. 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.