4-Aminodiphenylamine is a diphenylamine with an additional aminesubstituent. This dimer of aniline has various industrial uses, including as a hair dye ingredient, but also has raised concerns about toxicity by skin contact.[1] It is also a starting material for the synthesis of 6PPD, an antiozonant for various rubber products.[2] A colorimetric test for the quantitative analysis of nitrite, at levels below 100 nanograms per milliliter, is based on nitrite-catalyzed coupling of 4-aminodiphenylamine with N,N-dimethylaniline.[3]
The most common route of industrial production is by the reaction of aniline with 4‑nitrochlorobenzene followed by reduction of the intermediate 4‑nitrodiphenylamine.[4] An alternative is the direct condensation reaction of nitrobenzene with aniline via a nucleophilic aromatic substitution of hydrogen,[5] this again requires a reduction step.[4]
ReferencesEdit
^Khanna, S. K.; Tewari, Pushpa; Joshi, Anil; Singh, G. B. (1987). "Studies on the skin uptake and efflux kinetics of N‐phenyl‐p‐phenylenediamine: an aromatic amine intermediate". International Journal of Cosmetic Science. 9 (3): 137–147. doi:10.1111/j.1467-2494.1987.tb00470.x. PMID 19456976. S2CID 205555627.
^Engels, Hans-Wilhelm; Weidenhaupt, Herrmann‐Josef; Pieroth, Manfred; Hofmann, Werner; Menting, Karl‐Hans; Mergenhagen, Thomas; Schmoll, Ralf; Uhrlandt, Stefan (2007). "Rubber, 4. Chemicals and Additives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a23_365.pub2.
^Kadowaki, Ryoichi; Nakano, Shigenori; Kawashima, Takuji (1999). "Sensitive flow injection colorimetry of nitrite by catalytic coupling of N-phenyl-p-phenylenediamine with N,N-dimethylaniline". Talanta. 48 (1): 103–107. doi:10.1016/s0039-9140(98)00227-6. PMID 18967448.
^ abBochkarev, V.V.; Soroka, L.S.; Bashkin, J.K. (December 2016). "Resource-efficient technology to produce 4-aminodiphenylamine". Resource-Efficient Technologies. 2 (4): 215–224. doi:10.1016/j.reffit.2016.10.011.
^Stern, Michael K.; Hileman, Fredrick D.; Bashkin, James K. (November 1992). "The direct coupling of aniline and nitrobenzene: a new example of nucleophilic aromatic substitution for hydrogen". Journal of the American Chemical Society. 114 (23): 9237–9238. doi:10.1021/ja00049a095.
This article about an organic compound is a stub. You can help Wikipedia by expanding it.
aminodiphenylamine, diphenylamine, with, additional, amine, substituent, this, dimer, aniline, various, industrial, uses, including, hair, ingredient, also, raised, concerns, about, toxicity, skin, contact, also, starting, material, synthesis, 6ppd, antiozonan. 4 Aminodiphenylamine is a diphenylamine with an additional amine substituent This dimer of aniline has various industrial uses including as a hair dye ingredient but also has raised concerns about toxicity by skin contact 1 It is also a starting material for the synthesis of 6PPD an antiozonant for various rubber products 2 A colorimetric test for the quantitative analysis of nitrite at levels below 100 nanograms per milliliter is based on nitrite catalyzed coupling of 4 aminodiphenylamine with N N dimethylaniline 3 4 Aminodiphenylamine NamesPreferred IUPAC name N1 Phenylbenzene 1 4 diamineOther names 4 Aminodiphenylaminep AminodiphenylamineN Phenyl p phenylenediamineN Phenyl 1 4 phenylenediamineIdentifiersCAS Number 101 54 23D model JSmol Interactive imageBeilstein Reference 908935ChEBI CHEBI 59038ChEMBL ChEMBL572203ChemSpider 7283ECHA InfoCard 100 002 684EC Number 202 951 9Gmelin Reference 241334PubChem CID 7564RTECS number ST3150000UNII 007X4XXS71UN number 1673CompTox Dashboard EPA DTXSID7025895InChI InChI 1S C12H12N2 c13 10 6 8 12 9 7 10 14 11 4 2 1 3 5 11 h1 9 14H 13H2Key ATGUVEKSASEFFO UHFFFAOYSA NSMILES C1 CC C C C1 NC2 CC C C C2 NPropertiesChemical formula C 12H 12N 2Molar mass 184 242 g mol 1Appearance purple black or dark purpleDensity 1 09 g mLMelting point 75 C 167 F 348 K Boiling point 354 C 669 F 627 K HazardsGHS labelling PictogramsSignal word WarningHazard statements H302 H317 H319 H410Precautionary statements P261 P264 P270 P272 P273 P280 P301 P312 P302 P352 P305 P351 P338 P321 P330 P333 P313 P337 P313 P363 P391 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references The most common route of industrial production is by the reaction of aniline with 4 nitrochlorobenzene followed by reduction of the intermediate 4 nitrodiphenylamine 4 An alternative is the direct condensation reaction of nitrobenzene with aniline via a nucleophilic aromatic substitution of hydrogen 5 this again requires a reduction step 4 References Edit Khanna S K Tewari Pushpa Joshi Anil Singh G B 1987 Studies on the skin uptake and efflux kinetics of N phenyl p phenylenediamine an aromatic amine intermediate International Journal of Cosmetic Science 9 3 137 147 doi 10 1111 j 1467 2494 1987 tb00470 x PMID 19456976 S2CID 205555627 Engels Hans Wilhelm Weidenhaupt Herrmann Josef Pieroth Manfred Hofmann Werner Menting Karl Hans Mergenhagen Thomas Schmoll Ralf Uhrlandt Stefan 2007 Rubber 4 Chemicals and Additives Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a23 365 pub2 Kadowaki Ryoichi Nakano Shigenori Kawashima Takuji 1999 Sensitive flow injection colorimetry of nitrite by catalytic coupling of N phenyl p phenylenediamine with N N dimethylaniline Talanta 48 1 103 107 doi 10 1016 s0039 9140 98 00227 6 PMID 18967448 a b Bochkarev V V Soroka L S Bashkin J K December 2016 Resource efficient technology to produce 4 aminodiphenylamine Resource Efficient Technologies 2 4 215 224 doi 10 1016 j reffit 2016 10 011 Stern Michael K Hileman Fredrick D Bashkin James K November 1992 The direct coupling of aniline and nitrobenzene a new example of nucleophilic aromatic substitution for hydrogen Journal of the American Chemical Society 114 23 9237 9238 doi 10 1021 ja00049a095 nbsp This article about an organic compound is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title 4 Aminodiphenylamine amp oldid 1171973809, wikipedia, wiki, book, books, library,
