In
industrial chemistry
The chemical industry comprises the company, companies and other organizations that develop and produce industrial, specialty and other chemicals. Central to the modern world economy, the chemical industry converts raw materials (Petroleum, oil, ...
, carboalkoxylation is a process for converting
alkene
In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins.
The Internationa ...
s to
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. This reaction is a form of
carbonylation
In chemistry, carbonylation refers to reactions that introduce carbon monoxide (CO) into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemis ...
. A closely related reaction is
hydrocarboxylation, which employs water in place of
alcohols
In chemistry, an alcohol (), is a type of organic compound that carries at least one hydroxyl () functional group bound to a Saturated and unsaturated compounds, saturated carbon atom. Alcohols range from the simple, like methanol and ethanol ...
.
A commercial application is the carbomethoxylation of
ethylene
Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon bond, carbon–carbon doub ...
to give
methyl propionate:
:
The process is catalyzed by . Under similar conditions, other Pd-diphosphines catalyze formation of
polyethyleneketone.
Methyl propionate ester is a precursor to
methyl methacrylate
Methyl methacrylate (MMA) is an organic compound with the formula . This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).
History
MMA ...
, which is used in plastics and adhesives.
Carboalkoxylation has been incorporated into various
telomerization schemes. For example carboalkoxylation has been coupled with the dimerization of 1,3-
butadiene
1,3-Butadiene () is the organic compound with the formula CH2=CH-CH=CH2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two ...
. This step produces a doubly unsaturated C9-ester:
:
Hydroesterification
Related to carboalkoxylation is hydroesterification, the insertion of alkenes and alkynes into the H-O bond of carboxylic acids.
Vinyl acetate
Vinyl acetate is an organic compound with the Chemical formula, formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate, ethylene-vinyl acetate copolymers, polyvinyl alcohol, and other important industrial polymers.
Prod ...
is produced industrially by the addition of acetic acid to
acetylene
Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is u ...
in the presence of
zinc acetate catalysts:
Presently,
zinc acetate is used as the catalyst:
:
Further reading
*
References
{{Reflist
Chemical reactions
Carbon monoxide