industrial chemistry The chemical industry comprises the companies that produce industrial chemicals. Central to the modern world economy, it converts raw materials (oil, natural gas, air, water, metals, and minerals) into more than 70,000 different products. The pl ...

, carboalkoxylation is a process for converting

alkene 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, an ...

s to

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glyceride ...

s. This reaction is a form of

carbonylation Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carb ...

. A closely related reaction is

hydrocarboxylation Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbo ...

, which employs water in place of alcohols 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 double bonds). Ethylene ...

to give

methyl propionate Methyl propionate, also known as methyl propanoate, is an organic compound with the molecular formula CH3CH2CO2CH3. It is a colorless liquid with a fruity, rum-like odor. Preparation Methyl propionate can be prepared by esterification of propion ...

: :C₂H₄ + CO + MeOH → MeO₂CC₂H₅ The process is catalyzed by Pd ₆H₄(CH₂PBu-t)₂sub>2. 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 CH2=C(CH3)COOCH3. 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 ...

, 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)2. 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 viny ...

. This step produces a doubly unsaturated C9-ester: :2CH₂=CH-CH=CH₂ + CO + CH₃OH → CH₂=CH(CH₂)₃CH=CHCH₂CO₂CH₃

Hydroesterification

Related to carboalkoxylation is hydroesterification, the insertion of alkenes and alkynes into the H-O bond of carboxylic acids. Vinyl acetate is produced industrially by the addition of acetic acid to

acetylene Acetylene ( systematic name: ethyne) is the 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 unstable in its pure ...

in the presence of

zinc acetate Zinc acetate is a salt with the formula Zn(CH3CO2)2, which commonly occurs as the dihydrate Zn(CH3CO2)2·2H2O. Both the hydrate and the anhydrous forms are colorless solids that are used as dietary supplements. When used as a food additive, it ha ...

catalysts: Presently,

is used as the catalyst: :

References

{{Reflist Chemical reactions Carbon monoxide