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1-Pentanol

From Wikipedia, the free encyclopedia
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
3D model (JSmol)
1730975
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.000.684Edit this at Wikidata
EC Number
  • 200-752-1
25922
KEGG
MeSHn-Pentanol
RTECS number
  • SB9800000
UNII
UN number1105
  • InChI=1S/C5H12O/c1-2-3-4-5-6/h6H,2-5H2,1H3 checkY
    Key: AMQJEAYHLZJPGS-UHFFFAOYSA-N checkY
  • CCCCCO
Properties
C5H12O
Molar mass88.150 g·mol−1
Density0.811 g cm−3
Melting point−78 °C; −109 °F; 195 K
Boiling point137 to 139 °C; 278 to 282 °F; 410 to 412 K
22 g L−1
logP1.348
Vapor pressure200 Pa (at 20 °C)
−67.7·10−6 cm3/mol
1.409
Thermochemistry
207.45 J K−1 mol−1
258.9 J K−1 mol−1
−351.90–−351.34 kJ mol−1
−3331.19–−3330.63 kJ mol−1
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Warning
H226,H315,H332,H335
P261
NFPA 704 (fire diamond)
Flash point49 °C (120 °F; 322 K)
300 °C (572 °F; 573 K)
Related compounds
Related compounds
Hexane

Pentylamine

Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

1-Pentanol, (orn-pentanol,pentan-1-ol), is anorganic compound with the formulaCH3CH2CH2CH2CH2OH and is classified as aprimary alcohol.[2] It is a colourlessliquid with a distinctivearoma. It is one of 8isomeric alcohols with the formulaC5H11OH. It is used as a solvent, a biological drying agent and in the synthesis of some fragrance compounds. It is also a common component offusel alcohols (fusel oils), the undesirable byproducts ofalcoholic fermentation.

Preparation

[edit]

1-Pentanol is prepared from1-butene byhydroformylation followed byhydrogenation of the resultingpentanal.[3]

CH3CH2CH=CH2 + CO + H2 → CH3CH2CH2CH2CHO
CH3CH2CH2CH2CHO + H2 → CH3CH2CH2CH2CH2OH

Pentanol can be prepared byfractional distillation offusel oil. To reduce the use offossil fuels, research is underway to develop cost-effective methods of producing (chemically identical) bio-pentanol withfermentation.[4][5]

Uses and occurrence

[edit]

Thehydroxyl group (OH) is the active site of many reactions. Theester formed from 1-pentanol andbutyric acid ispentyl butyrate, which has anapricot-like odor. The ester formed from 1-pentanol andacetic acid isamyl acetate (also called pentyl acetate), which has abanana-like odor.

It is a precursor to dipentylzinc dithiophosphates, which are used in froth flotation.[3]

In 2014, a study was conducted comparing the performance ofdiesel fuel blends with various proportions of pentanol as anadditive. While gaseous emissions increased with higher concentrations of pentanol,particulate emissions decreased.[6]

Pentanol is often used as asolvent.

References

[edit]
  1. ^"n-pentanol - Compound Summary".PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved10 October 2011.
  2. ^CRC Handbook of Chemistry and Physics 65th ed.
  3. ^abLappe, 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 engineeredEscherichia 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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