Phthalic acid is an

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

dicarboxylic acid In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (). The general molecular formula for dicarboxylic acids can be written as , where R can be aliphatic or aromatic. In general, dicarboxylic acids show ...

, with formula C₆H₄(CO₂H)₂. Although phthalic acid is of modest commercial importance, the closely related derivative

phthalic anhydride Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commer ...

is a commodity chemical produced on a large scale. Phthalic acid is one of three

isomers In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...

benzenedicarboxylic acid Benzenedicarboxylic acid is a group of chemical compounds which are dicarboxylic derivatives of benzene. Benzenedicarboxylic acid comes in three isomers: *Phthalic acid (1,2-benzenedicarboxylic acid) *Isophthalic acid (1,3-benzenedicarboxylic aci ...

, the others being

isophthalic acid Isophthalic acid is an organic compound with the formula C6H4(CO2H)2. This colorless solid is an isomer of phthalic acid and terephthalic acid. The main industrial uses of purified isophthalic acid (PIA) are for the production of polyethylene t ...

and

terephthalic acid Terephthalic acid is an organic compound with formula C6H4(CO2H)2. This white solid is a commodity chemical, used principally as a precursor to the polyester PET, used to make clothing and plastic bottles. Several million tonnes are produced annua ...

Production

Phthalic acid is produced by the catalytic oxidation of

naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromati ...

or ''ortho-''xylene directly to

and a subsequent hydrolysis of the anhydride. Phthalic acid was first obtained by French

chemist A chemist (from Greek ''chēm(ía)'' alchemy; replacing ''chymist'' from Medieval Latin ''alchemist'') is a scientist trained in the study of chemistry. Chemists study the composition of matter and its properties. Chemists carefully describe th ...

Auguste Laurent in 1836 by

oxidizing Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a d ...

naphthalene tetrachloride. Believing the resulting substance to be a naphthalene derivative, he named it "naphthalic acid". After the

Swiss Swiss may refer to: * the adjectival form of Switzerland * Swiss people Places * Swiss, Missouri * Swiss, North Carolina *Swiss, West Virginia * Swiss, Wisconsin Other uses *Swiss-system tournament, in various games and sports *Swiss Internation ...

chemist

Jean Charles Galissard de Marignac Jean Charles Galissard de Marignac (24 April 1817 – 15 April 1894) was a Swiss chemist whose work with atomic weights suggested the possibility of isotopes and the packing fraction of nuclei. His study of the rare earth elements led to h ...

determined its correct formula, Laurent gave it its present name. Manufacturing methods in the nineteenth century included oxidation of naphthalene tetrachloride with nitric acid, or, better, oxidation of the hydrocarbon with fuming sulfuric acid, using mercury or mercury(II) sulfate as a catalyst.

Synthesis

Naphthalene on oxidation with

potassium permanganate Potassium permanganate is an inorganic compound with the chemical formula KMnO4. It is a purplish-black crystalline salt, that dissolves in water as K+ and , an intensely pink to purple solution. Potassium permanganate is widely used in the c ...

potassium dichromate Potassium dichromate, , is a common inorganic chemical reagent, most commonly used as an oxidizing agent in various laboratory and industrial applications. As with all hexavalent chromium compounds, it is acutely and chronically harmful to health ...

gives phthalic acid.

Reactions and uses

It is a dibasic acid, with p''K''_as of 2.89 and 5.51. The monopotassium salt,

potassium hydrogen phthalate Potassium hydrogen phthalate, often called simply KHP, is an acidic salt compound. It forms white powder, colorless crystals, a colorless solution, and an ionic solid that is the potassium, monopotassium salt of phthalic acid. KHP is slightly a ...

is a standard acid in

analytical chemistry Analytical chemistry studies and uses instruments and methods to separate, identify, and quantify matter. In practice, separation, identification or quantification may constitute the entire analysis or be combined with another method. Separati ...

. Typically phthalate esters are prepared from the widely available

. Reduction of phthalic acid with

sodium amalgam Sodium amalgam, commonly denoted Na(Hg), is an alloy of mercury and sodium. The term amalgam is used for alloys, intermetallic compounds, and solutions (both solid solutions and liquid solutions) involving mercury as a major component. Sodium amal ...

in the presence of water gives the 1,3-cyclohexadiene derivative.

Safety

The toxicity of phthalic acid is moderate with (mouse) of 550 mg/kg.

Biodegradation

The bacteria ''Pseudomonas'' sp. P1 degrades phthalic acid.

References

* Merck Index, 9th ed, #7178

External links

International Chemical Safety Card 0768
{{DEFAULTSORT:Phthalic Acid Benzoic acids Dicarboxylic acids