ACETIC ACID[C2H4O2]

·         CAS Number 64-19-7

·         Linear Formula CH₃CO₂H

·         Molecular Weight 60.05

·          Beilstein Registry Number 506007

·          EC Number 200-580-7

·          MDL number MFCD00036152

·          PubChem Substance ID 329770889

Acetic acid, systematically named ethanoic acid /ˌɛθəˈnoʊᵻk/, is a colourless liquid organic compound with the chemical formula CH₃COOH (also written as CH₃CO₂H or C₂H₄O₂). When undiluted, it is sometimes called glacial acetic acid. Vinegar is roughly 3–9% acetic acid by volume, making acetic acid the main component of vinegar apart from water.

 Detailed description

Uses

Acetic acid is a chemical reagent for the production of chemical compounds. The largest single use of acetic acid is in the production of vinyl acetate monomer, closely followed by acetic anhydride and ester production. The volume of acetic acid used in vinegar is comparatively small.

Vinyl acetate monomer

The primary use of acetic acid is the production of vinyl acetate monomer (VAM). In 2008, this application was estimated to consume a third of the world's production of acetic acid. The reaction consists of ethylene and acetic acid with oxygen over a palladium catalyst, conducted in the gas phase.^[43]

2 H₃C−COOH + 2 C₂H₄ + O₂ → 2 H₃C−CO−O−CH=CH₂ + 2 H₂O

Vinyl acetate can be polymerised to polyvinyl acetate or other polymers, which are components in paints and adhesives.^[43]

Ester production

The major esters of acetic acid are commonly used as solvents for inks, paints and coatings. The esters include ethyl acetate, n-butyl acetate, isobutyl acetate, and propyl acetate. They are typically produced by catalyzed reaction from acetic acid and the corresponding alcohol:

H₃C−COOH + HO−R → H₃C−CO−O−R + H₂O, (R = a general alkyl group)

Most acetate esters, however, are produced from acetaldehyde using the Tishchenko reaction. In addition, ether acetates are used as solvents for nitrocellulose, acrylic lacquers, varnish removers, and wood stains. First, glycol monoethers are produced from ethylene oxide or propylene oxide with alcohol, which are then esterified with acetic acid. The three major products are ethylene glycol monoethyl ether acetate (EEA), ethylene glycol monobutyl ether acetate (EBA), and propylene glycol monomethyl ether acetate (PMA, more commonly known as PGMEA in semiconductor manufacturing processes, where it is used as a resist solvent). This application consumes about 15% to 20% of worldwide acetic acid. Ether acetates, for example EEA, have been shown to be harmful to human reproduction.^[27]

Acetic anhydride

The product of the condensation of two molecules of acetic acid is acetic anhydride. The worldwide production of acetic anhydride is a major application, and uses approximately 25% to 30% of the global production of acetic acid. The main process involves dehydration of acetic acid to give ketene at 700–750 °C. Ketene is thereafter reacted with acetic acid to obtain the anhydride:^[44]

CH₃CO₂H → CH₂=C=O + H₂O

CH₃CO₂H + CH₂=C=O → (CH₃CO)₂O

Acetic anhydride is an acetylation agent. As such, its major application is for cellulose acetate, a synthetic textile also used for photographic film. Acetic anhydride is also a reagent for the production of heroin and other compounds.^[44]

Use as solvent

Glacial acetic acid is an excellent polar protic solvent, as noted above. It is frequently used as a solvent for recrystallization to purify organic compounds. Acetic acid is used as a solvent in the production of terephthalic acid (TPA), the raw material for polyethylene terephthalate (PET). In 2006, about 20% of acetic acid was used for TPA production.^[27]

Acetic acid is often used as a solvent for reactions involving carbocations, such as Friedel-Crafts alkylation. For example, one stage in the commercial manufacture of synthetic camphor involves a Wagner-Meerwein rearrangement of camphene to isobornyl acetate; here acetic acid acts both as a solvent and as a nucleophile to trap the rearrangedcarbocation.^[45]

Glacial acetic acid is used in analytical chemistry for the estimation of weakly alkaline substances such as organic amides. Glacial acetic acid is a much weaker base than water, so the amide behaves as a strong base in this medium. It then can be titrated using a solution in glacial acetic acid of a very strong acid, such as perchloric acid.

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$ 75.20/KG OR $34.18/IB

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