Aniline Yellow is a yellow

azo dye Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl and substituted aryl groups. They are a commercially important family of azo compounds, i.e. compounds containing the C-N=N ...

and an

aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aromatic ring attached to an amine. It is a broad class of compounds that encompasses anilines, but also many more complex aromatic rings and many amine substituents ...

. It is a derivative of

azobenzene Azobenzene is a photoswitchable chemical compound composed of two phenyl rings linked by a N=N double bond. It is the simplest example of an aryl azo compound. The term 'azobenzene' or simply 'azo' is often used to refer to a wide class of simi ...

. It has the appearance of an orange powder. Aniline Yellow was the first

. it was first produced in 1861 by C. Mene. The second azo dye was Bismarck Brown in 1863. Aniline Yellow was commercialized in 1864 as the first commercial azo dye, a year after

Aniline Black Polyaniline (PANI) is a conducting polymer and organic semiconductor of the semi-flexible rod polymer family. The compound has been of interest since the 1980s because of its electrical conductivity and mechanical properties. Polyaniline is one o ...

. It is manufactured from

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 ...

Uses

Aniline Yellow is used in

microscopy Microscopy is the technical field of using microscopes to view objects and areas of objects that cannot be seen with the naked eye (objects that are not within the resolution range of the normal eye). There are three well-known branches of micr ...

for

vital staining A vital stain in a casual usage may mean a stain that can be applied on living cells without killing them. Vital stains have been useful for diagnostic and surgical techniques in a variety of medical specialties. In supravital staining, living cells ...

, in

pyrotechnics Pyrotechnics is the science and craft of creating such things as fireworks, safety matches, oxygen candles, explosive bolts and other fasteners, parts of automotive airbags, as well as gas-pressure blasting in mining, quarrying, and demolition. ...

for yellow

colored smoke Colored smoke is a kind of smoke created by an aerosol of small particles of a suitable pigment or dye. Colored smoke can be used for smoke signals, often in a military context. It can be produced by smoke grenades, or by various other pyrote ...

s, in yellow

pigment A pigment is a colored material that is completely or nearly insoluble in water. In contrast, dyes are typically soluble, at least at some stage in their use. Generally dyes are often organic compounds whereas pigments are often inorganic compo ...

s and

ink Ink is a gel, sol, or solution that contains at least one colorant, such as a dye or pigment, and is used to color a surface to produce an image, text, or design. Ink is used for drawing or writing with a pen, brush, reed pen, or quill. Thicker ...

s including inks for

inkjet printer Inkjet printing is a type of computer printing that recreates a digital image by propelling droplets of ink onto paper and plastic substrates. Inkjet printers were the most commonly used type of printer in 2008, and range from small inexpensi ...

s. It is also used in insecticides, lacquers, varnishes, waxes, oil stains, and

styrene Styrene () is an organic compound with the chemical formula C6H5CH=CH2. This derivative of benzene is a colorless oily liquid, although aged samples can appear yellowish. The compound evaporates easily and has a sweet smell, although high concen ...

resin In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on natu ...

s. It is also an intermediate in synthesis of other dyes, e.g. chrysoidine, indulines,

Solid Yellow Solid is one of the four fundamental states of matter (the others being liquid, gas, and plasma). The molecules in a solid are closely packed together and contain the least amount of kinetic energy. A solid is characterized by structural ...

, and Acid Yellow.

Toxic oil syndrome

Aniline Yellow was initially implicated in the 1981 Spanish

Toxic Oil Syndrome Toxic oil syndrome (TOS) or simply toxic syndrome (Spanish: ''síndrome del aceite tóxico'' or ''síndrome tóxico'') is a musculoskeletal disease. A 1981 outbreak in Spain which affected about 20,000 people, with over 300 dying within a few m ...

(TOS), although further study suggested the cause was likely contaminated tomatoes. A Madrid-based company imported denaturated

rapeseed oil Close-up of canola blooms Canola flower Rapeseed oil is one of the oldest known vegetable oils. There are both edible and industrial forms produced from rapeseed, the seed of several cultivars of the plant family Brassicaceae. Historically, i ...

, dyed by aniline yellow to mark it as unsuitable for human consumption, to be used as a fuel in

steel mill A steel mill or steelworks is an industrial plant for the manufacture of steel. It may be an integrated steel works carrying out all steps of steelmaking from smelting iron ore to rolled product, but may also be a plant where steel semi-finish ...

s. However, the company distilled the oil to remove the dye, and sold it as a much more valuable

olive oil Olive oil is a liquid fat obtained from olives (the fruit of ''Olea europaea''; family Oleaceae), a traditional tree crop of the Mediterranean Basin, produced by pressing whole olives and extracting the oil. It is commonly used in cooking: f ...

for cooking. The result was a rash of

pneumonia Pneumonia is an inflammatory condition of the lung primarily affecting the small air sacs known as alveoli. Symptoms typically include some combination of productive or dry cough, chest pain, fever, and difficulty breathing. The severity ...

-type illnesses, with a second stage with

lesion A lesion is any damage or abnormal change in the tissue of an organism, usually caused by disease or trauma. ''Lesion'' is derived from the Latin "injury". Lesions may occur in plants as well as animals. Types There is no designated classifi ...

s, weight loss,

paralysis Paralysis (also known as plegia) is a loss of motor function in one or more muscles. Paralysis can also be accompanied by a loss of feeling (sensory loss) in the affected area if there is sensory damage. In the United States, roughly 1 in 50 ...

, and muscle wasting. The net result was over 20,000 sick and 400 dead. The chemistry of the poisonous reaction is still subject of a debate.

References

{{Reflist Azo dyes Vital stains Solvent dyes Anilines