Indigo dye is an organic compound with a distinctive blue color. Indigo is a natural dye obtained from the leaves of some plants of the Indigofera genus, in particular Indigofera tinctoria. Dye-bearing Indigofera plants were once common throughout the world. Blue colorants are relatively rare. Since indigo is insoluble, it is also referred to as a pigment (C.I. Pigment Blue 66, C.I.). Most indigo dye produced today is synthetic, constituting around 80,000 tonnes each year, as of 2023. It is most commonly associated with the production of denim cloth and blue jeans, where its properties allow for effects such as stone washing and acid washing to be applied quickly.
Uses
The primary use for indigo is as a dye for cotton yarn, mainly used in the production of denim cloth suitable for blue jeans; on average, a pair of blue jeans requires 3–12 grams (0.11–0.42 oz) of dye. Smaller quantities are used in the dyeing of wool and silk. Indigo's widespread use was partly due to its colorfast properties, as it binds effectively to fibers while allowing repeated dyeing processes that produce a range of shades. Indigo carmine, also known as indigo, is an indigo derivative which is also used as a colorant. About 20,000 tonnes are produced annually, again mainly for the production of blue jeans. Indigo is also used to dye the skin in Egypt, Kurdistan, and West Africa.
Sources
Natural sources
A variety of plants have provided indigo throughout history, but most natural indigo was obtained from those in the genus Indigofera, which are native to the tropics, notably the Indian Subcontinent. The primary commercial indigo species in Asia was true indigo (Indigofera tinctoria, also known as I. sumatrana). A common alternative used in the relatively colder subtropical locations such as Japan's Ryukyu Islands and Taiwan is Strobilanthes cusia. Until the introduction of Indigofera species from the south, Persicaria tinctoria (dyer's knotweed) was the most important blue dyestuff in East Asia; however, the crop produced less dyestuff than the average crop of indigo, and was quickly surpassed in favour of the more economical Indigofera tinctoria plant. In Central and South America, the species grown is Indigofera suffruticosa, also known as anil, and in India, an important species was Indigofera arrecta, Natal indigo. In Europe, Isatis tinctoria, commonly known as woad, was used for dyeing fabrics blue, containing the same dyeing compounds as indigo, also referred to as indigo. Several plants contain indigo, which, when exposed to an oxidizing source such as atmospheric oxygen, reacts to produce indigo dye; however, the relatively low concentrations of indigo in these plants make them difficult to work with, with the color more easily tainted by other dye substances also present in these plants, typically leading to a greenish tinge. The precursor to indigo is indican, a colorless, water-soluble derivative of the amino acid tryptophan, and Indigofera leaves contain as much as 0.2–0.8% of this compound. Pressing cut leaves into a vat and soaking hydrolyzes the indican, releasing β-D-glucose and indoxyl. The indoxyl dimerizes in the mixture, and after 12–15 hours of fermentation yields the yellow, water-soluble leucoindigo. Subsequent exposure to air forms the blue, water-insoluble indigo dye. The dye precipitates from the fermented leaf solution upon oxidation, but may also be precipitated when mixed with a strong base such as lye. The solids are filtered, pressed into cakes, dried, and powdered. The powder is then mixed with various other substances to produce different shades of blue and purple. Natural sources of indigo also include mollusks: the Murex genus of sea snails produces a mixture of indigo and 6,6'-dibromoindigo (red), which together produce a range of purple hues known as Tyrian purple. Light exposure during part of the dyeing process can convert the dibromoindigo into indigo, resulting in blue hues known as royal blue, hyacinth purple, or tekhelet.
Chemical synthesis
Given its economic importance, indigo has been prepared by many methods. The Baeyer–Drewsen indigo synthesis dates back to 1882. It involves an aldol condensation of o-nitrobenzaldehyde with acetone, followed by cyclization and oxidative dimerization to indigo. This route was highly useful for obtaining indigo and many of its derivatives on the laboratory scale, but proved impractical for industrial-scale synthesis. Johannes Pfleger and Karl Heumann eventually came up with industrial mass production synthesis from aniline by using mercury as a catalyst. The method was discovered by an accident by Karl Heumann in Zurich which involved a broken thermometer. The first commercially practical route of producing indigo is credited to Pfleger in 1901. In this process, N-phenylglycine is treated with a molten mixture of sodium hydroxide, potassium hydroxide, and sodamide. This highly sensitive melt produces indoxyl, which is subsequently oxidized in air to form indigo. Variations of this method are still in use today. An alternative and also viable route to indigo is credited to Heumann in 1897. It involves heating N-(2-carboxyphenyl)glycine to 200 °C (392 °F) in an inert atmosphere with sodium hydroxide. The process is easier than the Pfleger method, but the precursors are more expensive. Indoxyl-2-carboxylic acid is generated. This material readily decarboxylates to give indoxyl, which oxidizes in air to form indigo. The preparation of indigo dye is practised in college laboratory classes according to the original Baeyer–Drewsen route.
History
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