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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 sho ...
, 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. ...
of
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 te ...
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 an ...
.


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 aromat ...
or ''ortho-''xylene directly to
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 ...
and a subsequent hydrolysis of the anhydride. Phthalic acid was first obtained by
French French (french: français(e), link=no) may refer to: * Something of, from, or related to France ** French language, which originated in France, and its various dialects and accents ** French people, a nation and ethnic group identified with Franc ...
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 Auguste Laurent (14 November 1807 – 15 April 1853) was a French chemist who helped in the founding of organic chemistry with his discoveries of anthracene, phthalic acid, and carbolic acid. He devised a systematic nomenclature for organic che ...
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 ...
or
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
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 ...
. 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 am ...
in the presence of water gives the
1,3-cyclohexadiene Cyclohexa-1,3-diene is an organic compound with the formula (C2H4)(CH)4. It is a colorless, flammable liquid. Its refractive index is 1.475 (20 °C, D). A naturally occurring derivative of 1,3-cyclohexadiene is terpinene, a component of pine o ...
derivative.


Safety

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


Biodegradation

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


See also

*
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 te ...
*
Phthalate Phthalates (, ), or phthalate esters, are esters of phthalic acid. They are mainly used as plasticizers, i.e., substances added to plastics to increase their flexibility, transparency, durability, and longevity. They are used primarily to soften ...
*
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 ...
*
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 ...
, a
primary standard A primary standard in metrology is a standard that is sufficiently accurate such that it is not calibrated by or subordinate to other standards. Primary standards are defined via other quantities like length, mass and time. Primary standards are ...
for
acid–base titration An acid–base titration is a method of quantitative analysis for determining the concentration of an acid or base by exactly neutralizing it with a standard solution of base or acid having known concentration. A pH indicator is used to monit ...
s *
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 an ...


References

* Merck Index, 9th ed, #7178


External links


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