Names | |||
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Preferred IUPAC name Benzene-1,4-diamine | |||
Other names Paraphenylenediamine 1,4-Diaminobenzene 1,4-Phenylenediamine | |||
Identifiers | |||
3D model (JSmol) | |||
749029 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard | 100.003.096 | ||
EC Number |
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KEGG | |||
PubChem CID | |||
RTECS number |
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UNII | |||
UN number | 1673 | ||
CompTox Dashboard (EPA) | |||
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Properties | |||
C6H8N2 | |||
Molar mass | 108.144 g·mol−1 | ||
Appearance | White crystalline solid, darkens upon exposure to air [1] | ||
Melting point | 145 to 147 °C (293 to 297 °F; 418 to 420 K) [1] | ||
Boiling point | 267 °C (513 °F; 540 K) [1] | ||
10% at 40°C, 87% at 107 C, 100% at 140 C [2] | |||
Vapor pressure | <1 mmHg (20°C) [3] | ||
Acidity (pKa) |
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-70.28·10−6 cm3/mol | |||
Hazards | |||
GHS labelling: | |||
Danger | |||
H301, H311, H317, H319, H331, H410 | |||
P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P333+P313, P337+P313, P361, P363, P391, P403+P233, P405, P501 | |||
NFPA 704 (fire diamond) | |||
Flash point | 156 °C; 312 °F; 429 K [3] | ||
400 °C (752 °F; 673 K) | |||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) | 80 mg/kg (rat, oral) 98 mg/kg (rat, oral) 145 mg/kg (guinea pig, oral) [6] | ||
LDLo (lowest published) | 250 mg/kg (rabbit, oral) 100 mg/kg (cat, oral) [6] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible) | TWA 0.1 mg/m3 [skin] [3] | ||
REL (Recommended) | TWA 0.1 mg/m3 [skin] [3] | ||
IDLH (Immediate danger) | 25 mg/m3 [3] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
p-Phenylenediamine (PPD) is an organic compound with the formula C6H4(NH2)2. This derivative of aniline is a white solid, but samples can darken due to air oxidation. [1] It is mainly used as a component of engineering polymers and composites like kevlar. It is also an ingredient in hair dyes and is occasionally used as a substitute for henna.
PPD is produced via three routes. Most commonly, 4-nitrochlorobenzene is treated with ammonia and the resulting 4-nitroaniline is then hydrogenated:
In the DuPont route, aniline is converted to diphenyltriazine, which is then converted by acid-catalysis to 4-aminoazobenzene. Hydrogenation of the latter affords PPD. [7]
PPD is a precursor to aramid plastics and fibers such as Kevlar and Twaron. These applications exploit PPD's difunctionality, i.e. the presence of two amines which allow the molecules to be strung together. This polymer arises from the reaction of PPD and terephthaloyl chloride. The reaction of PPD with phosgene gives the diisocyanate, a precursor to urethane polymers. [7]
This compound is a common hair dye. Its use is being supplanted by other aniline analogues and derivatives such as 2,5-diamino(hydroxyethylbenzene and 2,5-diaminotoluene). Other popular derivatives include tetraaminopyrimidine and indoanilines and indophenols. Derivatives of diaminopyrazole give both red and violet colours. [8] In these applications, the nearly colourless dye precursor oxidizes to the dye.
PPD is easily oxidized, and for this reason, derivatives of PPD are used as antiozonants in the production of rubber products (e.g., IPPD). The substituents (naphthyl, isopropyl, etc.) affect the effectiveness of their antioxidant roles as well as their properties as skin irritants. [9]
A substituted form of PPD sold under the name CD-4 is also used as a developing agent in the C-41 color photographic film development process, reacting with the silver grains in the film and creating the colored dyes that form the image.
PPD is also used as a Henna surrogate for temporary tattoos. Its usage can lead to severe contact dermatitis.
PPD is also used as a histological stain for lipids such as myelin.
PPD is used by lichenologists in the PD test to aid identification of Lichens. [10] PPD is used extensively as a cross-linking agent in the formation of COFs (covalent organic frameworks), which have a number of applications in dyes and aromatic compounds adsorption.
The aquatic LD50 of PPD is 0.028 mg/L. [7] The U.S. Environmental Protection Agency reported that in rats and mice chronically exposed to PPD in their diet, it simply depressed body weights, and no other clinical signs of toxicity were observed in several studies. [11] One review of 31 English-language articles published between January 1992 and February 2005 that investigated the association between personal hair dye use and cancer as identified through the PubMed search engine found "at least one well-designed study with detailed exposure assessment" that observed associations between personal hair dye use and non-Hodgkin's lymphoma, multiple myeloma, acute leukemia, and bladder cancer, [12] but those associations were not consistently observed across studies. A formal meta-analysis was not possible due to the heterogeneity of the exposure assessment across the studies.
In 2005–06, it was the tenth-most-prevalent allergen in patch tests (5.0%). [13]
The CDC lists PPD as being a contact allergen. Exposure routes are through inhalation, skin absorption, ingestion, and skin and/or eye contact. Symptoms of exposure to PPD include throat irritation (pharynx and larynx), bronchial asthma, and sensitization dermatitis. [14] [15] Sensitization is a lifelong issue, which may lead to active sensitization to products, including but not limited to black clothing, various inks, hair dye, dyed fur, dyed leather, and certain photographic products. It was voted Allergen of the Year in 2006 by the American Contact Dermatitis Society.
Poisoning by PPD is rare in Western countries. [16] In contrast, poisoning by PPD has occurred in Eastern countries, such as Pakistan, where people have committed suicide by consuming it. [17]
N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It is a tertiary amine, featuring a dimethylamino group attached to a phenyl group. This oily liquid is colourless when pure, but commercial samples are often yellow. It is an important precursor to dyes such as crystal violet.
Aniline is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans.
Hair coloring, or hair dyeing, is the practice of changing the hair color. The main reasons for this are cosmetic: to cover gray or white hair, to alter hair to create a specific look, to change a color to suit preference or to restore the original hair color after it has been discolored by hairdressing processes or sun bleaching.
Nitrobenzene is an organic compound with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents.
Methylene diphenyl diisocyanate (MDI) is an aromatic diisocyanate. Three isomers are common, varying by the positions of the isocyanate groups around the rings: 2,2′-MDI, 2,4′-MDI, and 4,4′-MDI. The 4,4′ isomer is most widely used, and is also known as 4,4′-diphenylmethane diisocyanate. This isomer is also known as Pure MDI. MDI reacts with polyols in the manufacture of polyurethane. It is the most produced diisocyanate, accounting for 61.3% of the global market in the year 2000.
Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.
Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.
m-Phenylenediamine, also called 1,3-diaminobenzene, is an organic compound with the formula C6H4(NH2)2. It is an isomer of o-phenylenediamine and p-phenylenediamine. This aromatic diamine is a colourless solid that appears as needles, but turns red or purple on exposure to air due to formation of oxidation products. Samples often come as colourless flakes and may darken in storage.
2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.
Allergic contact dermatitis (ACD) is a form of contact dermatitis that is the manifestation of an allergic response caused by contact with a substance; the other type being irritant contact dermatitis (ICD).
Diphenylamine is an organic compound with the formula (C6H5)2NH. The compound is a derivative of aniline, consisting of an amine bound to two phenyl groups. The compound is a colorless solid, but commercial samples are often yellow due to oxidized impurities. Diphenylamine dissolves well in many common organic solvents, and is moderately soluble in water. It is used mainly for its antioxidant properties. Diphenylamine is widely used as an industrial antioxidant, dye mordant and reagent and is also employed in agriculture as a fungicide and antihelmintic.
Just for Men is an American-based multi-national men's care brand focusing on hair color, beard care, and hair re-growth designed for and marketed to men and manufactured by Combe Incorporated. Just for Men hair color brands are designed to color gray hair, with the Control Gx and Touch of Gray product lines providing options for gradual hair coloring. Just For Men comes in over 12 shades ranging from Sandy Blond to Jet Black.
1,2,4-Trichlorobenzene is an organochlorine compound, one of three isomers of trichlorobenzene. It is a derivative of benzene with three chloride substituents. It is a colorless liquid used as a solvent for a variety of compounds and materials.
4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6H6N2O2. A yellow solid, it is one of three isomers of nitroaniline. It is an intermediate in the production of dyes, antioxidants, pharmaceuticals, gasoline, gum inhibitors, poultry medicines, and as a corrosion inhibitor.
o-Anisidine (2-anisidine) is an organic compound with the formula CH3OC6H4NH2. A colorless liquid, commercial samples can appear yellow owing to air oxidation. It is one of three isomers of the methoxy-containing aniline derivative.
Methyl cyanoacrylate (MCA) is an organic compound that contains several functional groups: a methyl ester, a nitrile, and an alkene. It is a colorless liquid with low viscosity. Its chief use is as the main component of cyanoacrylate glues. It can be encountered under many trade names. Methyl cyanoacrylate is less commonly encountered than ethyl cyanoacrylate.
Henna is a dye prepared from the plant Lawsonia inermis, also known as the henna tree, the mignonette tree, and the Egyptian privet, and one of the only two species of the genus Lawsonia, with the other being Lawsonia odorata.
Allergen of the Year is an annual award voted upon by the American Contact Dermatitis Society. This is "designed to draw attention to allergens that are very common, under-recognized, merit more attention because they are causing significant allergic contact dermatitis or are no longer causing significant relevant disease ".
4,4′-Methylenedianiline (MDA) is an organic compound with the formula CH2(C6H4NH2)2. It is a colorless solid, although commercial samples can appear yellow or brown. It is produced on an industrial scale, mainly as a precursor to polyurethanes.
Butyl acrylate is an organic compound with the formula C4H9O2CCH=CH2. A colorless liquid, it is the butyl ester of acrylic acid. It is used commercially on a large scale as a precursor to poly(butyl acrylate). Especially as copolymers, such materials are used in paints, sealants, coatings, adhesives, fuel, textiles, plastics, and caulk.