1-Pentanol

1-Pentanol
Skeletal formula of 1-pentanol
Skeletal formula of 1-pentanol
Ball and stick model of 1-pentanol
Ball and stick model of 1-pentanol
Names
Preferred IUPAC name
Pentan-1-ol[1]
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference
 1730975
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.684
EC Number
  • 200-752-1
Gmelin Reference
 25922
KEGG
MeSH n-Pentanol
RTECS number
  • SB9800000
UNII
UN number 1105
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H12O/c1-2-3-4-5-6/h6H,2-5H2,1H3 checkY
    Key: AMQJEAYHLZJPGS-UHFFFAOYSA-N checkY
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
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
 GHS02: Flammable GHS07: Exclamation mark
Signal word
 Warning
Hazard statements
 H226, H315, H332, H335
Precautionary statements
 P261
NFPA 704 (fire diamond)
NFPA 704 four-colored 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).
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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. ^ a b 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.
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