Chemical Properties
Diphenylamine is a colorless monoclinic leafl et substance. It is used in the manufacture
of a variety of substances, i.e., dyestuffs and their intermediates, pesticides, antihelmintic
drugs, and as reagents in analytical chemistry laboratories.
General Description
Light tan to brown solid with a pleasant odor. Sinks in water.
Reactivity Profile
DIPHENYLAMINE(122-39-4) discolors in light. This chemical can react violently with hexachloromelamine and trichloromelamine. DIPHENYLAMINE(122-39-4) is incompatible with strong oxidizing agents and strong acids. DIPHENYLAMINE(122-39-4) is also incompatible with iron and silver salts. DIPHENYLAMINE(122-39-4) reacts with nitrogen oxides.
Air & Water Reactions
Dust may be explosive if mixed with air in critical proportions and in the presence of a source of ignition [USCG, 1999]. Insoluble in water.
Health Hazard
Diphenylamine is highly toxic and is rapidly absorbed by the skin and through inhalation.
It has caused anorexia, hypertension, eczema, and bladder symptoms. Experimental
animals exposed to diphenylamine demonstrated cystic lesions but failed to demonstrate
cancerous growth. Inhalation of diphenylamine dust may cause systemic poisoning. The
symptoms of toxicity include, but are not limited to, anoxia, headache, fatigue, anorexia,
cyanosis, vomiting, diarrhea, emaciation, hypothermia, bladder irritation, kidney, heart,
and liver damage.
Health Hazard
Inhalation may irritate mucous membranes. Overexposure, including ingestion of solid or skin contact, may cause fast pulse, hypertension, and bladder trouble. Contact with dust irritates eyes.
Description
Solutions of diphenylamine are used to treat apples a few days
before harvest. Residue on apples’ surfaces of 10 ppm is
permitted by regulation in Australia, Canada, and the United
States.
Uses
Diphenylamine is an aromatic amine that was shown to exhibit antioxidant activities and is now used as an anti-scald agent. It is also used in the manufacture of a variety of substances, for instance, dye stuffs and their intermediates, pesticides, anthelmintic drugs, and as reagents in analytical chemistry laboratories.
Uses
Diphenylamine is used in the manufactureof dyes, as a stabilizer for nitrocelluloseexplosives, and as an analytical reagent forcolorimetric tests for nitrate and chlorate.
Other applications of this compoundinclude preventing postharvest deteriorationof apple and peer crops; as an antioxidant inrubber and elastomer industry and in the per fumery. As a stabilizer for propellants andexplosives, it binds their degradation prod ucts thus prolonging the storage time of suchpropellants.
Uses
Diphenylamine is used post-harvest to prevent superficial scald in
apples in cold store.
Definition
ChEBI: An aromatic amine containing two phenyl substituents. It has been used as a fungicide for the treatment of superficial scald in apples and pears, but is no longer approved for this purpose within the European Union.
Definition
diphenylamine: A colourless crystallinearomatic compound,(C6H5)2NH; m.p. 54°C. It is made byheating phenylamine (aniline) withphenylamine hydrochloride. It is asecondary amine and is both slightlyacidic (forming an N-potassium salt)and slightly basic (forming salts withmineral acids). Its derivatives are employedas stabilizers for syntheticrubber and rocket fuels.
Fire Hazard
Noncombustible solid; autoignition temperature 634°C (1173°F); low reactivity.
Flammability and Explosibility
Nonflammable
Agricultural Uses
Insecticide, Fungicide, Herbicide, Plant growth
regulator: Topically in anti-screwworm mixtures, foliar application in a modified growth chamber to decrease ozone injury to
leaves of apple, bean, muskmelon, petunia, and tobacco plants.
To control weather fleck in tobacco and inhibit algae formation. To prolong the fresh appearance of snapdragons. Protect
rice from the toxic effects of thiolcarbamate herbicides [83] . Not
currently approved for use in EU countries (resubmitted) .
Registered for use in the U.S. and other countries.
Trade name
NOSCALD DPA 31; NOSCALD DPA
283; SCALDIP; Z-876
Potential Exposure
AgriculturalChemical; Mutagen; Reproductive Effector. DPA is used asa stabilizer for plastics including solid rocket propellants;antioxidant for polymers, greases, and industrial oils; in themanufacture of pharmaceuticals; pesticides, explosives, anddyes.
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. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.Medical observation is recommended.
Environmental Fate
Diphenylamine is present in waste water from industrial
processes. Diphenylamine has been detected in milk of
animals (cow, sheep, goat, water buffalo) raised in Italy and
France.
Pseudokirchneriella subcapitata (Algae) growth was inhibited
with a dose of 0.30 mg l-1. Aquatic invertebrates Daphnia
magna showed an acute 48 h EC50 dose of 1.2 mg l-1.
Metabolic pathway
The major metabolite of diphenylamine (DPA)
identified in stored apples is a glucose conjugate of
4-hydroxydiphenylamine, and additional metabolites,
characterized as glycosyl conjugates of 2-hydroxy-
DPA, 3-hydroxy-DPA, 4-hydroxy-DPA, or dihydroxy-
DPA, are also detected along with their intact (i.e.
non-conjugated) forms in apple pulp.
Shipping
Toxic solids, flammable, organic, n.o.s. requiresa shipping label of “POISONOUS/TOXIC MATERIALS.”It falls into Hazard Class 6.1.
Purification Methods
Crystallise diphenylamine from pet ether, MeOH, or EtOH/water. Dry it under vacuum. [Beilstein 12 H 174, 12 IV 271.]
Degradation
Diphenylamine is an anti-oxidant and therefore reacts with oxygen under
conditions of use. It darkens on exposure to sunlight. Aqueous photolysis
is pH and oxygen dependant (Lopez et al., 1980). It is converted into
carbazole (2) and hydrogen peroxide in the presence of dissolved oxygen.
In degassed solution it is converted into carbazole (2) and tetrahydrocarbazole
(3) (see Scheme 1).
Incompatibilities
Dust may form an explosive mixturewith air. Incompatible with strong acids, strong oxidizers,aldehydes, organic anhydrides, isocyanates, hexachloromelamine, trichloromelamine. Reacts with nitrogen oxidesforming n-nitrosodiphenylamine and heat-, friction-, andshock-sensitive nitro products
