2-Ethyl-1-butanol (
IUPAC
The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...
name: 2-ethylbutan-1-ol) is an
organic
Organic may refer to:
* Organic, of or relating to an organism, a living entity
* Organic, of or relating to an anatomical organ
Chemistry
* Organic matter, matter that has come from a once-living organism, is capable of decay or is the product ...
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
. It can be used to facilitate the separation of
ethanol
Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
from
water
Water is an inorganic compound with the chemical formula . It is a transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance. It is the main constituent of Earth's hydrosphere and the fluids of all known liv ...
, which forms an
azeotrope
An azeotrope () or a constant heating point mixture is a mixture of two or more liquids whose proportions cannot be changed by simple distillation.Moore, Walter J. ''Physical Chemistry'', 3rd e Prentice-Hall 1962, pp. 140–142 This happens beca ...
that otherwise limits the maximum ethanol concentration.
Reactions
2-Ethyl-1-butanol is manufactured industrially by the
aldol condensation
An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration t ...
of
acetaldehyde
Acetaldehyde (IUPAC systematic name ethanal) is an organic compound, organic chemical compound with the chemical formula, formula , sometimes abbreviated as . It is a colorless liquid or gas, boiling near room temperature. It is one of the most ...
and
butyraldehyde
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. ...
, followed by
hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...
.
[
] It may also be prepared by the
Guerbet reaction
The Guerbet reaction, named after Marcel Guerbet (1861–1938), is an organic reaction that converts a primary Alcohol (chemistry), alcohol into its β-alkylated Dimer (chemistry), dimer Alcohol (chemistry), alcohol with loss of one equivalent of w ...
.
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
*
2-Ethylhexanol
2-Ethylhexanol (abbreviated 2-EH) is an organic compound with the chemical formula . It is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is produced on a l ...
References
{{DEFAULTSORT:Ethyl-1-butanol, 2-
Hexanols