2-Ethylhexanol (abbreviated 2-EH) is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the

chemical formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as pare ...

. It is a branched, eight-carbon

chiral Chirality () is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek language, Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is dist ...

alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...

. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is

produce In American English, produce generally refers to wikt:fresh, fresh List of culinary fruits, fruits and Vegetable, vegetables intended to be Eating, eaten by humans, although other food products such as Dairy product, dairy products or Nut (foo ...

d on a large scale (>2,000,000,000 kg/y) for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers. It is encountered in plants, fruits, and wines. The odor has been reported as "heavy, earthy, and slightly floral" for the R

enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

and "a light, sweet floral fragrance" for the S enantiomer.

Properties and applications

The branching in 2-ethylhexanol inhibits crystallization. Esters of 2-ethylhexanol are similarly affected, which together with low volatility, is the basis of applications in the production of

plasticizer A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture. Plasticizer ...

s and lubricants, where its presence helps reduce viscosity and lower freezing points. Because 2-ethylhexanol is a

fatty alcohol Fatty alcohols (or long-chain alcohols) are usually high-molecular mass, straight-chain primary alcohols, but can also range from as few as 4–6 carbon atoms to as many as 22–26, derived from natural fats and oils. The precise chain length vari ...

, its

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

s have emollient properties. Representative is the diester bis(2-ethylhexyl) phthalate (DEHP), commonly used in PVC. The triester tris (2-Ethylhexyl) trimellitate (TOTM) is another common plasticizer produced via the

esterification In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

of three 2-ethylhexanol per trimellitic acid. It is also commonly used as a low volatility

solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

. The

nitrate ester In organic chemistry, a nitrate ester is an organic functional group with the formula , where R stands for any organyl group. They are the esters of nitric acid and alcohols. A well-known example is nitroglycerin, which is not a ''nitro'' comp ...

of 2-Ethylhexanol is also used as a cetane improver for

diesel fuel Diesel fuel, also called diesel oil, heavy oil (historically) or simply diesel, is any liquid fuel specifically designed for use in a diesel engine, a type of internal combustion engine in which fuel ignition takes place without a spark as a re ...

. It also used to react with epichlorohydrin and

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...

to produce 2-Ethylhexyl glycidyl ether which is then used as an epoxy reactive diluent in various

coating A coating is a covering that is applied to the surface of an object, or substrate. The purpose of applying the coating may be decorative, functional, or both. Coatings may be applied as liquids, gases or solids e.g. powder coatings. Paints ...

adhesive Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation. The use of adhesives offers certain advantage ...

s and

sealant Sealant is a substance used to block the passage of fluids through openings in materials, a type of Seal (mechanical), mechanical seal. In building construction ''sealant'' is sometimes synonymous with ''caulk'' (especially if acrylic latex or ...

s applications. It can be used in the development of photos, production of rubber and extraction of oil and gas.

Industrial production

2-Ethylhexanol is produced industrially by the

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 ...

2-ethylhexanal. About 2,500,000 tons are prepared in this way annually.

Health effects

2-Ethylhexanol exhibits low toxicity in animal models, with

LD50 In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a given substance. The value of LD50 for a substance is the dose requ ...

ranging from 2-3 g/kg (rat). 2-Ethylhexanol has been identified as a cause of

indoor air quality Indoor air quality (IAQ) is the air quality within buildings and Nonbuilding structure, structures. Poor indoor air quality due to indoor air pollution is known to affect the health, comfort, and well-being of building occupants. It has also be ...

Nomenclature

Although isooctanol (and the derived isooctyl prefix) is commonly used in industry to refer to 2-ethylhexanol and its derivatives,

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 ...

naming conventions dictate that this name is properly applied to another

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...

of octanol, 6-methylheptan-1-ol. The

Chemical Abstracts Service Chemical Abstracts Service (CAS) is a division of the American Chemical Society. It is a source of chemical information and is located in Columbus, Ohio, United States. Print periodicals ''Chemical Abstracts'' is a periodical index that provid ...

likewise indexes isooctanol (CAS# 26952-21-6) as 6-methylheptan-1-ol.

References

External links