Carbonylation

hydrocarboxylationReppe synthesisReppe chemistryBuna rubberscarbonylatedecarbonylationhydrocarbonylationReppe reaction
Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates.wikipedia
129 Related Articles

Monsanto process

MonsantoMonsanto acetic acid processMonsanto acetic acid synthesis
Large-scale applications of this type of carbonylation are the Monsanto and Cativa processes, which convert methanol to acetic acid.
The Monsanto process is an industrial method for the manufacture of acetic acid by catalytic carbonylation of methanol.

Cativa process

Cativa
Large-scale applications of this type of carbonylation are the Monsanto and Cativa processes, which convert methanol to acetic acid.
The Cativa process is a method for the production of acetic acid by the carbonylation of methanol.

Acetic acid

aceticglacial acetic acidacetate
Large-scale applications of this type of carbonylation are the Monsanto and Cativa processes, which convert methanol to acetic acid.
About 75% of acetic acid made for use in the chemical industry is made by the carbonylation of methanol, explained below.

Decarbonylation

decarbonylates
Many organic carbonyls undergo decarbonylation.
The reverse reaction, carbonylation, involves the insertion of CO into a bond, is a common and industrially relevant reaction.

Acetic anhydride

Ac 2 Oacetic anhydridesacetanhydride
Acetic anhydride is prepared by a related carbonylation of methyl acetate.
Acetic anhydride is produced by carbonylation of methyl acetate:

Propionic acid

propanoate metabolismpropanoic acidpropionic
This method is used in industry to produce propionic acid from ethylene:
In industry, propionic acid is mainly produced by the hydrocarboxylation of ethylene using nickel carbonyl as the catalyst:

Aldehyde

aldehydesformylformyl group
Carbonylations produce organic carbonyls, i.e., compounds that contain the C=O functional group such as aldehydes, carboxylic acids, and esters.
Acetaldehyde once was a dominating product, but production levels have declined to less than 1,000,000 tons per year because it mainly served as a precursor to acetic acid, which is now prepared by carbonylation of methanol.

Methyl acetate

Acetic anhydride is prepared by a related carbonylation of methyl acetate.
Methyl acetate is produced industrially via the carbonylation of methanol as a byproduct of the production of acetic acid.

Catalysis

catalyzescatalysescatalyst
The reaction requires metal catalysts that bind the CO, the H 2, and the alkene, allowing these substrates to combine within its coordination sphere.
Most carbonylation processes require metal catalysts, examples include the Monsanto acetic acid process and hydroformylation.

Nickel tetracarbonyl

nickel carbonylNi(CO) 4 nickel(II) carbonyl
In industry, propanoic acid is mainly produced by the hydrocarboxylation of ethylene using nickel carbonyl as the catalyst:
It is conveniently generated in the laboratory by carbonylation of commercially available bis(cyclooctadiene)nickel(0).

Koch reaction

The Koch reaction is a special case of hydrocarboxylation reaction that does not rely on metal catalysts.
The reaction is a strongly acid-catalyzed carbonylation using carbon monoxide, and typically occurs at high pressures ranging from 50 to 5,000 kPa, often requiring temperatures several hundred degrees higher than room temperature.

Carboalkoxylation

hydroesterification
Hydroesterification is like hydrocarboxylation, but uses alcohols instead of water.
Also called hydroesterification, this reaction is a form of carbonylation.

Pivalic acid

pivalatepivaloyl chloridePivaloyl
The conversion of isobutene to pivalic acid is also illustrative:
Pivalic acid is prepared by hydrocarboxylation of isobutene via the Koch reaction:

Metal carbonyl

carbonylInfrared spectroscopy of metal carbonylsBridging carbonyl
Metal carbonyls, compounds with the formula M(CO) x L y (M = metal; L = other ligands) are prepared by carbonylation of transition metals.
Metal carbonyls are useful in organic synthesis and as catalysts or catalyst precursors in homogeneous catalysis, such as hydroformylation and Reppe chemistry.

Glycolic acid

glycolateglycolatesglycolic
The industrial synthesis of glycolic acid is achieved in this way:
The predominant approaches uses a catalyzed reaction of formaldehyde with synthesis gas (carbonylation of formaldehyde), for its low cost.

Alkene

olefinalkenesolefins
Hydroformylation entails the addition of both carbon monoxide and hydrogen to unsaturated organic compounds, usually alkenes.

Chemical reaction

reactionchemical reactionsreactions
Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates.

Carbon monoxide

COcarbon monoxide (CO)carbon monoxide poisoning
Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates.

Organic compound

syntheticorganicorganic compounds
Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates.

Inorganic compound

inorganicinorganic compoundsinorganic chemical
Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates.

Carbonyl group

carbonylcarbonyl compoundcarbonyls
Carbonylations produce organic carbonyls, i.e., compounds that contain the C=O functional group such as aldehydes, carboxylic acids, and esters.

Functional group

groupfunctional groupsmoiety
Carbonylations produce organic carbonyls, i.e., compounds that contain the C=O functional group such as aldehydes, carboxylic acids, and esters.

Carboxylic acid

carboxylcarboxyl groupcarboxylic acids
Carbonylations produce organic carbonyls, i.e., compounds that contain the C=O functional group such as aldehydes, carboxylic acids, and esters.

Ester

estersesterificationmonoester
Carbonylations produce organic carbonyls, i.e., compounds that contain the C=O functional group such as aldehydes, carboxylic acids, and esters.

Hydroformylation

oxo processoxo synthesishydroformylated
Hydroformylation entails the addition of both carbon monoxide and hydrogen to unsaturated organic compounds, usually alkenes.