1-Pentanol

Last updated
1-Pentanol
Pentan-1-ol-2D-skeletal.png
Pentan-1-ol-3D-balls.png
Names
Preferred IUPAC name
Pentan-1-ol [1]
Identifiers
3D model (JSmol)
1730975
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.684 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-752-1
25922
KEGG
MeSH n-Pentanol
PubChem CID
RTECS number
  • SB9800000
UNII
UN number 1105
  • InChI=1S/C5H12O/c1-2-3-4-5-6/h6H,2-5H2,1H3 Yes check.svgY
    Key: AMQJEAYHLZJPGS-UHFFFAOYSA-N Yes check.svgY
  • CCCCCO
Properties
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)
-67.7·10−6 cm3/mol
1.409
Thermochemistry
207.45 J K−1 mol−1
Std molar
entropy
(S298)
258.9 J K−1 mol−1
−351.90–−351.34 kJ mol−1
−3331.19–−3330.63 kJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Warning
H226, H315, H332, H335
P261
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Flash point 49 °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 their standard state (at 25 °C [77 °F], 100 kPa).
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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.

Contents

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.

Related Research Articles

<span class="mw-page-title-main">Alcohol (chemistry)</span> Organic compound with at least one hydroxyl (–OH) group

In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl functional group bound to a saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sucrose and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.

<span class="mw-page-title-main">Amyl alcohol</span> Chemical compound family

Amyl alcohols are alcohols with the formula C5H11OH. Eight are known. A mixture of amyl alcohols (also called amyl alcohol) can be obtained from fusel alcohol. Amyl alcohol is used as a solvent and in esterification, by which is produced amyl acetate and other products. The name amyl alcohol without further specification applies to the normal (straight-chain) form, 1-pentanol.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Ethanol</span> Organic compound (CH₃CH₂OH)

Ethanol is an organic compound with the chemical formula CH3CH2OH. It is an alcohol, with its formula also written as C2H5OH, C2H6O or EtOH, where Et stands for ethyl. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive recreational drug, and the active ingredient in alcoholic drinks.

Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4H9OH, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; all are a butyl or isobutyl group linked to a hydroxyl group (sometimes represented as BuOH, 1-BuOH, i-BuOH, and t-BuOH). These are 1-butanol, two stereoisomers of sec-butyl alcohol, isobutanol and tert-butyl alcohol. Butanol is primarily used as a solvent and as an intermediate in chemical synthesis, and may be used as a fuel. Biologically produced butanol is called biobutanol, which may be n-butanol or isobutanol.

<span class="mw-page-title-main">Acetate</span> Salt compound formed from acetic acid and a base

An acetate is a salt formed by the combination of acetic acid with a base. "Acetate" also describes the conjugate base or ion typically found in aqueous solution and written with the chemical formula C
2
H
3
O
2
. The neutral molecules formed by the combination of the acetate ion and a positive ion are also commonly called "acetates". The simplest of these is hydrogen acetate with corresponding salts, esters, and the polyatomic anion CH
3
CO
2
, or CH
3
COO
.

Fusel alcohols or fuselol, also sometimes called fusel oils in Europe, are mixtures of several higher alcohols produced as a by-product of alcoholic fermentation. The word Fusel is German for "bad liquor".

<span class="mw-page-title-main">Sodium borohydride</span> Chemical compound

Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula NaBH4. It is a white crystalline solid, usually encountered as an aqueous basic solution. Sodium borohydride is a reducing agent that finds application in papermaking and dye industries. It is also used as a reagent in organic synthesis.

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

<span class="mw-page-title-main">Valeric acid</span> Carboxylic acid – CH3(CH2)3COOH

Valeric acid or pentanoic acid is a straight-chain alkyl carboxylic acid with the chemical formula CH3(CH2)3COOH. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. It is found in the perennial flowering plant Valeriana officinalis, from which it gets its name. Its primary use is in the synthesis of its esters. Salts and esters of valeric acid are known as valerates or pentanoates. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Several, including ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors.

<span class="mw-page-title-main">Amyl acetate</span> Chemical compound

Amyl acetate (pentyl acetate) is an organic compound and an ester with the chemical formula CH3COO[CH2]4CH3 and the molecular weight 130.19 g/mol. It is colorless and has a scent similar to bananas and apples. The compound is the condensation product of acetic acid and 1-pentanol. However, esters formed from other pentanol isomers (amyl alcohols), or mixtures of pentanols, are often referred to as amyl acetate. The symptoms of exposure to amyl acetate in humans are dermatitis, central nervous system depression, narcosis and irritation to the eyes and nose.

<span class="mw-page-title-main">Palladium(II) acetate</span> Chemical compound

Palladium(II) acetate is a chemical compound of palladium described by the formula [Pd(O2CCH3)2]n, abbreviated [Pd(OAc)2]n. It is more reactive than the analogous platinum compound. Depending on the value of n, the compound is soluble in many organic solvents and is commonly used as a catalyst for organic reactions.

<span class="mw-page-title-main">Pentyl group</span> Chemical compound

Pentyl is a five-carbon alkyl group or substituent with chemical formula -C5H11. It is the substituent form of the alkane pentane.

<span class="mw-page-title-main">Isobutanol</span> Chemical compound

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

<span class="mw-page-title-main">1-Propanol</span> Primary alcohol compound

1-Propanol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colourless liquid and an isomer of 2-propanol. 1-Propanol is used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.

<span class="mw-page-title-main">Isoamyl acetate</span> Chemical compound with banana odor

Isoamyl acetate, also known as isopentyl acetate, is an ester formed from isoamyl alcohol and acetic acid, with the molecular formula . It is a colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isoamyl acetate has a strong odor which is described as similar to both banana and pear. Pure isoamyl acetate, or mixtures of isoamyl acetate, amyl acetate, and other flavors in ethanol may be referred to as banana oil or pear oil.

<span class="mw-page-title-main">Isoamyl alcohol</span> Chemical compound

Isoamyl alcohol is a colorless liquid with the formula C
5
H
12
O
, specifically (H3C–)2CH–CH2–CH2–OH. It is one of several isomers of amyl alcohol (pentanol). It is also known as isopentyl alcohol, isopentanol, or (in the IUPAC recommended nomenclature) 3-methyl-butan-1-ol. An obsolete name for it was isobutyl carbinol.

<span class="mw-page-title-main">1-Butanol</span> Chemical compound

1-Butanol, also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and tert-butanol. The unmodified term butanol usually refers to the straight chain isomer.

<span class="mw-page-title-main">Bioconversion of biomass to mixed alcohol fuels</span>

The bioconversion of biomass to mixed alcohol fuels can be accomplished using the MixAlco process. Through bioconversion of biomass to a mixed alcohol fuel, more energy from the biomass will end up as liquid fuels than in converting biomass to ethanol by yeast fermentation.

<span class="mw-page-title-main">Phenethyl alcohol</span> Chemical compound

Phenethyl alcohol, or 2-phenylethanol, is an organic compound with the chemical formula C6H5CH2CH2OH. It is a colourless liquid with a pleasant floral odor. It occurs widely in nature, being found in a variety of essential oils. It is slightly soluble in water, but miscible with most organic solvents. The molecule of phenethyl alcohol consists of a phenethyl group attached to a hydroxyl group.

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. 1 2 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.