Oxo alcohols are

alcohols In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl () functional group bound to a saturated carbon atom. The term ''alcohol'' originally referred to the primary alcohol ethanol (ethyl alcohol), which is ...

that are prepared by adding

carbon monoxide Carbon monoxide ( chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simpl ...

(CO) and

hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-to ...

(usually combined as

synthesis gas Syngas, or synthesis gas, is a mixture of hydrogen and carbon monoxide, in various ratios. The gas often contains some carbon dioxide and methane. It is principly used for producing ammonia or methanol. Syngas is combustible and can be used ...

) to an

olefin In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, a ...

to obtain an

aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl gro ...

using the

hydroformylation Hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes from alkenes. This chemical reaction entails the net addition of a formyl group (CHO) and a hydrogen atom to a carbon-carbon ...

reaction and then hydrogenating the aldehyde to obtain the alcohol. An intermediate step of adding two aldehydes together to obtain a larger aldehyde (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 to ...

reaction) can precede the hydrogenation. Long chain oxo-alcohols are often prepared using

alpha-olefin In organic chemistry, alpha-olefins (or α-olefins) are a family of organic compounds which are alkenes (also known as olefins) with a chemical formula , distinguished by having a double bond at the primary or alpha (α) position.''Petrochemical ...

s from the

Shell higher olefin process The Shell higher olefin process (SHOP) is a chemical process for the production of linear alpha olefins via ethylene oligomerization and olefin metathesis invented and exploited by Royal Dutch Shell.''Industrial Organic Chemistry'', Klaus Weisserm ...

, to give secondary alcohols such as isodecyl alcohol. Key oxo alcohols that are sold in commerce include the following: *

2-Methyl-2-butanol ''tert''-Amyl alcohol (TAA) or 2-methylbutan-2-ol (2M2B), is a branched pentanol. Historically TAA has been used an anesthetic and more recently used as a recreational drug. TAA is mostly a positive allosteric modulator for GABAA receptors in t ...

(2M2B) * ''n''-Butanol *

2-Ethylhexanol 2-Ethylhexanol (abbreviated 2-EH) is an organic compound with formula CHO. 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 large scal ...

2-Propylheptanol 2-Propylheptanol (2PH) is a colourless waxy or oily solid. Production 2-Propylheptanol is an oxo alcohol, meaning that it is produced from the hydroformylation ("oxo synthesis") of C4 alkenes followed by hydrogenation of the resulting aldehyde. ...

* Isononyl alcohol * Isodecyl alcohol Key manufacturers of oxo alcohols include the following companies: *

BASF BASF SE () is a German multinational chemical company and the largest chemical producer in the world. Its headquarters is located in Ludwigshafen, Germany. The BASF Group comprises subsidiaries and joint ventures in more than 80 countries ...

Dow Chemical Company The Dow Chemical Company, officially Dow Inc., is an American multinational chemical corporation headquartered in Midland, Michigan, United States. The company is among the three largest chemical producers in the world. Dow manufactures plastics ...

Eastman Chemical Company Eastman Chemical Company is an American company primarily involved in the chemical industry. Once a subsidiary of Kodak, today it is an independent global specialty materials company that produces a broad range of advanced materials, chemicals and ...

ExxonMobil ExxonMobil Corporation (commonly shortened to Exxon) is an American multinational oil and gas corporation headquartered in Irving, Texas. It is the largest direct descendant of John D. Rockefeller's Standard Oil, and was formed on November 3 ...

Chemical Company * Grupa Azoty *

PETRONAS Petroliam Nasional Berhad (National Petroleum Limited), commonly known as Petronas, is a Malaysian petroleum, oil and natural gas, gas company. Established in 1974 and wholly owned by the Government of Malaysia, the corporation is vested w ...

Sasol Sasol Limited is an integrated energy and chemical company based in Sandton, South Africa. The company was formed in 1950 in Sasolburg, South Africa and built on processes that were first developed by German chemists and engineers in the early ...

Oxo alcohols are used as

solvents A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

and are reacted with

phthalic anhydride Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commer ...

to form

phthalates Phthalates (, ), or phthalate esters, are esters of phthalic acid. They are mainly used as plasticizers, i.e., substances added to plastics to increase their flexibility, transparency, durability, and longevity. They are used primarily to soften ...

, which find use in commerce as

vinyl Vinyl may refer to: Chemistry * Polyvinyl chloride (PVC), a particular vinyl polymer * Vinyl cation, a type of carbocation * Vinyl group, a broad class of organic molecules in chemistry * Vinyl polymer, a group of polymers derived from vinyl ...

plasticizers 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. Plastic ...

References

{{reflist Alcohols

See also

References