Description
4-N,N-Dimethylaminobenzene diazonium chloride is a
diazo compound found in diazo copy paper. It is
allergenic only when unexposed.
Chemical Properties
yellow to orange crystalline powder
Uses
Butter yellow was largely used as a food coloring agent. It was
also used for the determination of free hydrochloric acid in
gastric juice, for the spot test identification of peroxidized fats,
as a pH indicator, and as a laboratory reagent.
Uses
Formerly used as a coloring agent in
foods, drugs, and cosmetics
Uses
For determination of free HCl in gastric juice; spot test identification of peroxidized fats; pH indicator (red 2.9, yellow 4.0).
Preparation
aniline diazotization, and N,N-dimethylaniline coupling.
Definition
A banned food coloring.
Production Methods
4-Dimethylaminoazobenzene was produced in large quantities
in the early 1900s but is currently not produced in
any significant commercial quantity in the United States.
General Description
Yellow crystalline leaflets or an orange powder.
Air & Water Reactions
Dust may form an explosive mixture in air. Insoluble in water.
Reactivity Profile
Solvent Yellow 2 can detonate, particularly if sensitized by the presence of metal salts or strong acids. May form toxic gases with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. May form flammable gases with alkali metals. May react explosively with strong oxidizing agents, metal salts, peroxides, and sulfides. May react explosively with strong oxidizing agents, metal salts, peroxides, and sulfides.
Health Hazard
4-Dimethylamino-azobenzene (XIII) is the parent compound of the amino-azo dye carcinogens; it is also known in the earlier literature as Butter Yellow, because it was used to color butter and vegetable oils before its carcinogenic activity was discovered. Many derivatives of XIII have been prepared and tested for carcinogenic activity. In the rat, the amino-azo dye carcinogens, administered in the diet, specifically induce hepatomas. Tumor induction by most of the amino-azo dyes is delayed or inhibited by high dietary levels of riboflavin (vitamin B2) or protein. Replacement of the –N=N– azo linkage by –CH=CH–, as in 4-dimethylaminostilbene (XIV), results in widening the target tissue spectrum; XIV induces tumors in the liver, mammary gland, and ear duct. Mice are much more resistant than rats to the carcinogenic activity of both amino-azo dyes and aminostilbenes.
Fire Hazard
Flash point data for Solvent Yellow 2 are not available. Solvent Yellow 2 is probably combustible.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic,
neoplastigenic, and tumorigenic data. Poison
by ingestion and intraperitoneal routes.
Experimental teratogenic and reproductive
effects. Human mutation data reported.
When heated to decomposition it emits
toxic fumes of NOx
Potential Exposure
Tumorigen,Drug, Mutagen; Reproductive Effector DAB is used for coloring polishes and other wax products, polystyrene, petrol,soap, and as a chemical indicator. Human exposure to DABcan occur through either inhalation or skin absorption.
First aid
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. Contact a physician, hospital, or poison center atonce. If the victim is unconscious or convulsing, do notinduce vomiting or give anything by mouth. Assure that thepatient’s airway is open and if conscious and not convulsing, give a glass of water to dilute the substance. Vomitingshould not be induced without a physician’s advice.
Carcinogenicity
4-Dimethylaminoazobenzene is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity fromstudies in experimental animals.
Environmental Fate
Chemical/Physical. Releases toxic nitrogen oxides when heated to decomposition (Sax and
Lewis, 1987).
At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities
were 249, 140, 83, and 48 mg/g, respectively (Dobbs and Cohen, 1980).
storage
Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with DAB youshould be trained on its proper handling and storage. Storein a cool, dry place and protect from exposure to light andair. A regulated, marked area should be established wherethis chemical is handled, used, or stored in compliance withOSHA Standard 1910.1045.
Shipping
Dyes, solid, toxic, n.o.s. require a label of“POISONOUS/TOXIC MATERIALS.” 4-Dimethylaminoazo-benzene falls in Hazard Class 6.1; Packing Group III.
Properties and Applications
yellow to red light yellow. Light yellow powder, melting point 115 ℃ (yellow flaky crystal). Insoluble in water, soluble in ethanol for yellow solution, in oil soluble. In concentrated sulfuric acid to yellow, red after diluted solution; . Mainly used for Aviation fuel TETRAETHYLLEAD stability agent and pH indicator, also used in paraffin, polystyrene, oil and soap stain
|
Standard
|
Light Fastness
|
Heat-resistant(℃)
|
Water
|
Sodium Carbonate(5%)
|
Hydrochloric acid(5%)
|
|
Melting point
|
Stable
|
|
ISO
|
General
|
113.5-115
|
120
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Poor
|
Well
|
Poor
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Purification Methods
Crystallise the dye from acetic acid or isooctane, or from 95% EtOH by adding hot water and cooling. Dry it over KOH under vacuum at 50o. [Beilstein 6 IV 448.] CARCINOGEN.
Toxicity evaluation
Butter yellow exists as a stable crystalline material at normal
temperature and pressure. It is insoluble in water, but soluble in
organic solvents such as alcohol, chloroform, ether, petroleum
ether, mineral acids, oils, and pyridine. Its octanol/water partition
coefficient is 4.58, vapor pressure is 3.3×10-7 mm Hg;
and Henry’s law constant is 7.1×10-9 atm-m
3 mol
-1.
Butter yellow may be released into the environment as
a result of its manufacture and use in the consumer products.
It may bind to the soil and when released into water, may
bioconcentrate in aquatic organisms, or may be adsorbed into
the sediment. If released in the atmosphere, it may undergo
direct photolysis.
Incompatibilities
None reported.
