Production of anthraquinone

Two methods are available to the production of anthraquinone and anthra-quinone-derivatives  

Because of adequate availability of anthracene, oxidation is preferred to synthesis, but the latter can, however, be advantageous when substitution is required in specific positions. 

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Production of anthraquinone reactive dyes based on derivatives of bromamine acid (8) was first commercialized in 1956. Some improvements have been made and now they ate predominandy used among the reactive blue dyes. Cl Reactive Blue 19 [2580-78-1] (9) (Cl 61200) (developed by Hoechst in 1957) has the greatest share among them including dye chromophores other than anthraquinones. 

Benzanthrone has been prepared by three general methods, the first of which is generally regarded as the best (i) by heating a reduction product of anthraquinone with sulfuric acid and glycerol,1 or with a derivative of glycerol, or with acrolein. The anthraquinone is usually reduced in sulfuric acid solution, just prior to the reaction, by means of aniline sulfate, iron, , or copper. It has also been prepared (2) by the action of aluminum or ferric chloride on phenyl-a-naphthyl ketone, and (3) from i-phenylnaphthalene-2-carboxylic acid. ... 

Liquid-impelled loop reactor Production of anthraquinones Plant cell culture 124... 

Schulte, U., H. El-Shagi, and M. H. Zenk, "Optimization of 19 Rubiaceae species in cell culture for the production of anthraquinones," Plant Cell Reports 3 (1984) 51-54. 

The production of anthraquinone dyes generally proceeds from a few key products generated by electrophilic substitution of unsubstituted anthraquinone or by synthesis of the nucleus. The major methods employed to prepare anthraquinone derivatives substituted in the a-position are sulfonation and nitration. Preparation of b-substituted anthraquinones and of quinizarin (1,4-dihydroxyan-thraquinone) generally is accomplished by synthesis of the nucleus starting from phthalic anhydride and a benzene derivative. 

Intensive efforts have also been made to find an electrochemical process for the synthesis of 1,4-naphthoquinone starting from naphthalene. The aim of this work is to develop a new process for the production of anthraquinone from 1,4-naphthoquinone and butadiene. 

As already mentioned, the basic operations of dye chemistry utiUze simple chemical reactions. An intermediate can frequently be prepared in several entirely different ways and, in these cases, careful calculations must be made to determine which procediure is most advantageous. The least expensive process is often not necessarily the best when other factors are taken into account. For example, the question of apparatus may enter, and calculations may show that it is uneconomical to purchase an expensive apparatus for the process if a small quantity of the material is to be produced. Furthermore, consideration must be given to the usability of the side products formed. These often cannot be used at all (e.g., primuline), but may be valuable or even indispensable in another process (e.g, chromium sulfate in the production of anthraquinone). 

Anthracene and phenanthrene are stereoisomers that are crystals in pure form. Anthracene is a pale yellow crystal, while phenanthrene exhibits a yellow to brown hue. Besides its common name, anthracene is referred to as anthracin, green oil, or paranaphthalene. The compound is commercially produced by recovery from the coal tar distillation fraction known as anthracene oil or green oil. Anthracene is the key ingredient in the production of anthraquinone. However, it and phenanthrene are also used for the manufacture of dyes, fibers, plastics, and wood preservatives. ° Phenanthrene, also known as phenanthrin, can be produced by high-temperature fractional distillation of coal tar oil. It is additionally used for the oxidation of diphenic acid for use in polymers, as well as the production of chemical softeners, explosives, and some pharma-ceuticals. Recent research has extended the application of both isomers to scintillation counters, semiconductors, and photoconductors. ... 

Lesser,R., DiSerio, M., Ambrosio, M., andSantacesaria, E. 2002. Heterogeneous catalysts for the production of anthraquinone from 2-benzoylbenzoic acid. Chem. Eng. ]. 90 195-201. 

The anthrone is the reduction product of anthraquinone and was recognized first as spiecific reagent for several carbohydrates by Dreywood (1946) because sugar solution in concentrate sulphuric add form the blue-greenish colour characteristic and since anthrone has been used widely as suitable and sp>ecific reagent for sugar colorimetric dosage. 

Tetrahydroanthraquinone is used as a catalyst in wood pulping (see Chapter 11.6) and for the production of anthraquinone by dehydrogenation. 

The industrial importance of anthracene consists mainly in its use as a raw material in the production of anthraquinone small amounts are used in production of the tranquilizer benzoctamine, which is produced from anthracene and acrolein in a Diels-Alder reaction, followed by reductive amination of the aldehyde with methylamine. 

Synthetic production of anthraquinone is based on Friedel-Crafts acylation of benzene with phthalic anhydride, and the Diels-Alder reaction of naphthoquinone with butadiene. 

Not only plants, but also insects served as a basis for the production of anthraquinone dyes. A dyestuff known in America for centuries, carminic acid, was produced from cochineal beetles this dye was first imported into Spain in 1530. 

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