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Concept
Acrylic acid
Summary
Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.
The word "acrylic" was coined in 1843, for a chemical derivative of acrolein, an acrid-smelling oil derived from glycerol.
Acrylic acid is produced by oxidation of propylene, which is a byproduct of the production of ethylene and gasoline:
2 CH2=CHCH3 + 3 O2 → 2 CH2=CHCO2H + 2 H2O
Because acrylic acid and its esters have long been valued commercially, many other methods have been developed. Most have been abandoned for economic or environmental reasons. An early method was the hydrocarboxylation of acetylene ("Reppe chemistry"):
This method requires nickel carbonyl, high pressures of carbon monoxide, and acetylene, which is relatively expensive compared to propylene.
Acrylic acid was once manufactured by the hydrolysis of acrylonitrile, a material derived from propene by ammoxidation, but this route was abandoned because it cogenerates ammonium side products, which must be disposed of. Other now abandoned precursors to acrylic acid include ethenone and ethylene cyanohydrin.
Propane is a much cheaper raw material than propylene, so an alternative route being explored is the one-step selective oxidation of propane.
Carboxylating ethylene to acrylic acid under supercritical carbon dioxide condition is thermodynamically possible, but efficient catalysts have not been developed. 3-Hydroxypropionic acid (3HP), an acrylic-acid precursor by dehydration, can be produced from sugars, but the process is not competitive.
Acrylic acid undergoes the typical reactions of a carboxylic acid. When reacted with an alcohol, it forms the corresponding ester. The esters and salts of acrylic acid are collectively known as acrylates (or propenoates).
Official source
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