2-Ethyl-1-butanol

Last updated
2-Ethyl-1-butanol [1]
Structural formula of 2-ethylbutan-1-ol.svg
2-Ethyl-1-butanol 3D ball.png
Names
Preferred IUPAC name
2-Ethylbutan-1-ol
Other names
2-Ethyl-1-butanol
Identifiers
3D model (JSmol)
1731254
ChemSpider
ECHA InfoCard 100.002.384 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-621-4
PubChem CID
RTECS number
  • EL3850000
UNII
UN number 2275
  • InChI=1S/C6H14O/c1-3-6(4-2)5-7/h6-7H,3-5H2,1-2H3 Yes check.svgY
    Key: TZYRSLHNPKPEFV-UHFFFAOYSA-N Yes check.svgY
  • CCC(CC)CO
Properties
C6H14O
Molar mass 102.177 g·mol−1
AppearanceColorless liquid
Density 830 mg mL−1
Melting point −114.40 °C; −173.92 °F; 158.75 K
Boiling point 145 to 151 °C; 293 to 304 °F; 418 to 424 K
10 g L−1
Vapor pressure 206 Pa
1.422
Thermochemistry
246.65 J K−1 mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H312
P280
Flash point 58 °C (136 °F; 331 K)
Lethal dose or concentration (LD, LC):
1.85 g kg−1(oral, rat)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Ethyl-1-butanol (IUPAC name: 2-ethylbutan-1-ol) is an organic chemical compound. It can be used to facilitate the separation of ethanol from water, which forms an azeotrope that otherwise limits the maximum ethanol concentration. [2]

Contents

Reactions

2-Ethyl-1-butanol is manufactured industrially by the aldol condensation of acetaldehyde and butyraldehyde, followed by hydrogenation. [3] It may also be prepared by the Guerbet reaction.

Properties and applications

The branching in 2-ethyl-1-butanol makes it harder to crystallize due to packing disruption, which results in a very low freezing point. Esters of 2-ethyl-1-butanol are similarly effected and it therefore finds application as a feedstock in the production of plasticizers and lubricants, where its presence helps reduce viscosity and lower freezing points.

See also

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">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.

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

Diethyl malonate, also known as DEM, is the diethyl ester of malonic acid. It occurs naturally in grapes and strawberries as a colourless liquid with an apple-like odour, and is used in perfumes. It is also used to synthesize other compounds such as barbiturates, artificial flavourings, vitamin B1, and vitamin B6.

<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

Butan-2-ol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol, isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-butan-2-ol and (S)-(+)-butan-2-ol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

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

Butyraldehyde, also known as butanal, is an organic compound with the formula CH3(CH2)2CHO. This compound is the aldehyde derivative of butane. It is a colorless flammable liquid with an unpleasant smell. It is miscible with most organic solvents.

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

Phosphoryl chloride is a colourless liquid with the formula POCl3. It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride. It is manufactured industrially on a large scale from phosphorus trichloride and oxygen or phosphorus pentoxide. It is mainly used to make phosphate esters such as tricresyl phosphate.

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

n-Butyl acetate is an organic compound with the formula CH3CO2(CH2)3CH3. A colorless, flammable liquid, it is the ester derived from n-butanol and acetic acid. It is found in many types of fruit, where it imparts characteristic flavors and has a sweet smell of banana or apple. It is used as an industrial solvent.

Hexachlorobenzene, or perchlorobenzene, is an organochloride with the molecular formula C6Cl6. It is a fungicide formerly used as a seed treatment, especially on wheat to control the fungal disease bunt. It has been banned globally under the Stockholm Convention on Persistent Organic Pollutants.

<span class="mw-page-title-main">Miscibility</span> Ability of two substances to form a homogeneous solution when mixed regardless of concentration

Miscibility is the property of two substances to mix in all proportions, forming a homogeneous mixture. The term is most often applied to liquids but also applies to solids and gases. An example in liquids is the miscibility of water and ethanol as they mix in all proportions.

<i>tert</i>-Amyl alcohol Chemical compound

tert-Amyl alcohol (TAA) or 2-methylbutan-2-ol (2M2B), is a branched pentanol.

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2-Methyl-1-butanol (IUPAC name, also called active amyl alcohol) is an organic compound with the formula CH3CH2CH(CH3)CH2OH. It is one of several isomers of amyl alcohol. A colorless liquid, it occurs naturally in trace amounts and has attracted some attention as a potential biofuel, exploiting its hydrophobic (gasoline-like) and branched structure. It is chiral.

<span class="mw-page-title-main">2-Pentanol</span> Chemical compound

2-Pentanol is an organic chemical compound. It is used as a solvent and an intermediate in the manufacturing of other chemicals. 2-Pentanol is a component of many mixtures of amyl alcohols sold industrially. 2-Pentanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-pentanol and (S)-(+)-2-pentanol.

<span class="mw-page-title-main">3-Hexanol</span> Chemical compound

3-Hexanol is an organic chemical compound. It occurs naturally in the flavor and aroma of plants such as pineapple and is used as a food additive to add flavor.

<span class="mw-page-title-main">2-Methyl-2-pentanol</span> Chemical compound

2-Methyl-2-pentanol is an organic chemical compound. It can be added to a gas chromatograph to help distinguish between branched compounds, especially alcohols. Its presence in urine can be used to test for exposure to 2-methylpentane. As with many other short-chain alcohols, 2-methyl-2-pentanol can produce intoxication and sedative effects similar to those of ethanol, though it is more irritating to mucous membranes and generally more toxic to the body.

<span class="mw-page-title-main">4-Methyl-2-pentanol</span> Chemical compound

4-Methyl-2-pentanol or methyl isobutyl carbinol (MIBC) is an organic chemical compound used primarily as a frother in mineral flotation and in the production of lubricant oil additives such as Zinc dithiophosphate. It is also used as a solvent, in organic synthesis, and in the manufacture of brake fluid and as a precursor to some plasticizers. It is an acetone derivative in liquid state, with limited solubility in water but generally miscible with most organic solvents.

<span class="mw-page-title-main">2,2-Dimethyl-1-butanol</span> Chemical compound

2,2-Dimethyl-1-butanol is an organic chemical compound; it is one of the isomeric hexanols. Its main use is as a solvent.

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

Sodium ferrioxalate is a chemical compound with the formula Na3Fe(C2O4)3. It often occurs as a hydrate such as Na3[Fe(C2O4)3nH2O, are lime green in colour. It is also called sodium oxalatoferrate or sodium trisoxalatoferrate.

3-Methyl-2-butanol is an organic chemical compound. It is used as a solvent and an intermediate in the manufacture of other chemicals.

<span class="mw-page-title-main">Chromium(III) bromide</span> Chemical compound

Chromium(III) bromide is an inorganic compound with the chemical formula CrBr3. It is a dark colored solid that appears green in transmitted light but red with reflected light. It is used as a precursor to catalysts for the oligomerization of ethylene.

References

  1. Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 3–262, 8–106, 15–20, ISBN   978-0-8493-0594-8
  2. Roddy, James W. (1981). "Distribution of ethanol-water mixtures to organic liquids". Ind. Eng. Chem. Proc. Des. Dev. 20 (1): 104–108. doi:10.1021/i200012a016.
  3. McKetta, John J.; Cunningham, William Aaron (1994), Encyclopedia of Chemical Processing and Design, vol. 47, Boca Raton, Florida: CRC Press, p. 117, ISBN   978-0-8247-2451-1 , retrieved 2010-01-25