1,4-Dihydroxyanthraquinone, also called quinizarin or Solvent Orange 86, is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

derived from anthroquinone. Quinizarin is an orange or red-brown crystalline powder. It is formally derived from

anthraquinone Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula . Isomers include various quinone derivatives. The term anthraquinone however refers to the isomer, 9,10-anthraquinone (IUPAC: 9,10-dioxo ...

by replacement of two

hydrogen Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...

atoms by

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

(OH) groups. It is one of ten dihydroxyanthraquinone isomers and occurs in small amounts (as a

glycoside In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. ...

) in the root of the

madder ''Rubia'' is the type genus of the Rubiaceae family of flowering plants, which also contains coffee. It contains around 80 species of perennial scrambling or climbing herbs and subshrubs native to the Old World. The genus and its best-known spe ...

plant, ''

Rubia tinctorum ''Rubia tinctorum'', the rose madder or common madder or dyer's madder, is a herbaceous perennial plant species belonging to the Galium, bedstraw and Coffea, coffee family Rubiaceae. Description The common madder can grow up to 1.5 m in height ...

''.

Production

Quinizarin is produced by the reaction of

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 4-chlorophenol followed by hydrolysis of the chloride: QuinizarinPrep

It can also be prepared less efficiently from

and

hydroquinone Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a ''para'' ...

Uses

Quinizarin is an inexpensive dye that is used to colour

gasoline Gasoline (; ) or petrol (; ) (see ) is a transparent, petroleum-derived flammable liquid that is used primarily as a fuel in most spark-ignited internal combustion engines (also known as petrol engines). It consists mostly of organic co ...

and some

heating oil Heating oil is any petroleum product or other oil used for heating; a fuel oil. Most commonly, it refers to low viscosity grades of fuel oil used for furnaces or boilers use for home heating and in other buildings. Home heating oil is often a ...

s. It is used as an intermediate for the synthesis of indanthrene- and

alizarin Alizarin (also known as 1,2-dihydroxyanthraquinone, Mordant Red 11, C.I. 58000, and Turkey Red) is an organic compound with formula that has been used throughout history as a prominent red dye, principally for dyeing textile fabrics. Histori ...

-derived dyes. The OH groups can be replaced by chloride.

Chlorination Chlorination may refer to: * Chlorination reaction In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transform ...

and

bromination In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polyme ...

afford other dyes. Amination (replacement of one OH by ArNH) with

aniline Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aroma ...

derivatives followed by sulfonation affords other dyes such as Acid Violet 43. It is also used to form

lake pigment A lake pigment is a pigment made by precipitating a dye with an inert binder, or mordant, usually a metallic salt. Unlike vermilion, ultramarine, and other pigments made from ground minerals, lake pigments are organic.K. Hunger. W. Herbst "Pigm ...

s with

calcium Calcium is a chemical element with the symbol Ca and atomic number 20. As an alkaline earth metal, calcium is a reactive metal that forms a dark oxide-nitride layer when exposed to air. Its physical and chemical properties are most similar to ...

barium Barium is a chemical element with the symbol Ba and atomic number 56. It is the fifth element in group 2 and is a soft, silvery alkaline earth metal. Because of its high chemical reactivity, barium is never found in nature as a free element. Th ...

, and

lead Lead is a chemical element with the symbol Pb (from the Latin ) and atomic number 82. It is a heavy metal that is denser than most common materials. Lead is soft and malleable, and also has a relatively low melting point. When freshly cu ...

References

{{DEFAULTSORT:Dihydroxyanthraquinone, 1,4- Anthraquinone dyes Dihydroxyanthraquinones Hydroquinones 3-Hydroxypropenals within hydroxyquinones

Production

Uses

See also

References