Diphenylamine

Last updated
Diphenylamine
Diphenylamine 200.svg
Diphenylamine-3D-balls.png
Names
Preferred IUPAC name
N-Phenylaniline [1]
Other names
(Diphenyl)amine
Diphenylamine (deprecated [1] )
Diphenylazane
N-Phenylbenzenamine
Anilinobenzene
(Phenylamino)benzene
N,N-Diphenylamine
C.I. 10355
Phenylbenzenamine
Identifiers
3D model (JSmol)
AbbreviationsDPA
508755
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.128 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-539-4
67833
KEGG
PubChem CID
RTECS number
  • JJ7800000
UNII
UN number 2811 3077
  • InChI=1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H Yes check.svgY
    Key: DMBHHRLKUKUOEG-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
    Key: DMBHHRLKUKUOEG-UHFFFAOYAJ
  • c1ccc(cc1)Nc2ccccc2
Properties
C12H11N
Molar mass 169.23 g/mol
AppearanceWhite, off-white [2]
Odor Floral [3]
Density 1.2 g/cm3
Melting point 53 °C (127 °F; 326 K)
Boiling point 302 °C (576 °F; 575 K)
0.03% [3]
Vapor pressure 1 mmHg (108°C) [3]
Acidity (pKa)0.79 [4]
-109.7·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic. Possible mutagen. Possible teratogen. Harmful in contact with skin, and if swallowed or inhaled. Irritant.
GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H301, H311, H319, H331, H373, H410
P260, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P311, P312, P314, P321, P322, P330, P337+P313, P361, P363, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Flash point 152 °C (306 °F; 425 K)
NIOSH (US health exposure limits):
PEL (Permissible)
none [3]
REL (Recommended)
TWA 10 mg/m3 [3]
IDLH (Immediate danger)
N.D. [3]
Related compounds
Related Amine
Aniline
Supplementary data page
Diphenylamine (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [5] Diphenylamine dissolves well in many common organic solvents, and is moderately soluble in water. [6] 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. [7]

Contents

Preparation and reactivity

Diphenylamine is manufactured by the thermal deamination of aniline over oxide catalysts:

2 C6H5NH2 → (C6H5)2NH + NH3

It is a weak base, with a Kb of 10−14. With strong acids, it forms salts. For example, treatment with sulfuric acid gives the bisulfate [(C6H5)2NH2]+[HSO4]− as a white or yellowish powder with m.p. 123-125 °C. [8]

Diphenylamine undergoes various cyclisation reactions. With sulfur, it gives phenothiazine, a precursor to pharmaceuticals. [9]

(C6H5)2NH + 2 S → S(C6H4)2NH + H2S

With iodine, it undergoes dehydrogenation to give carbazole, with release of hydrogen iodide:

(C6H5)2NH + I2 → (C6H4)2NH + 2 HI

Arylation with iodobenzene gives triphenylamine. [10] it is also used as a test reagent in the dische's test .

Applications

Testing for DNA

The Dische test uses diphenylamine to test for DNA, and can be used to distinguish DNA from RNA.

Apple scald inhibitor

Diphenylamine is used as a pre- or postharvest scald inhibitor for apples applied as an indoor drench treatment. Its anti-scald activity is the result of its antioxidant properties, which protect the apple skin from the oxidation products of α-farnesene during storage. [11] Apple scald is physical injury that manifests in brown spots after fruit is removed from cold storage.

Stabilizer for smokeless powder

In the manufacture of smokeless powder, diphenylamine is commonly used as a stabilizer, [12] such that the gunshot residue analysis seeks to quantify traces of diphenylamine. [13] Diphenylamine functions by binding nitrogen oxide degradation products), forming compounds like nitrodiphenylamine. In this way, DPA prevents these degradation products from accelerating further degradation. [14]

Antioxidant

Alkylated diphenylamines function as antioxidants in lubricants, [15] approved for use in machines, in which contact with food is not ruled out. [16] Alkylated diphenylamines and other derivatives are used as anti-ozonants in the manufacture of rubber products, reflecting the antioxidant nature of aniline derivatives. [5] [17]

Redox indicator

Many diphenylamine derivatives are used as redox indicators that are particularly useful in alkaline redox titrations. [18] The diphenylaminesulfonic acid is a simple prototype redox indicator, owing to its improved aqueous solubility compared with diphenylamine. [19] Attempts have been made to explain the color changes associated with the oxidation of diphenylamine. [20] [21]

In a related application, diphenylamine is oxidized by nitrate to give a similar blue coloration in the diphenylamine test for nitrates.

Dyes

Several azo dyes like Metanil Yellow, Disperse Orange 1, and Acid orange 5 are derivatives of diphenylamine.

History

Diphenylamine was discovered by A. W. Hofmann in 1864 amongst the products of dry distillation of aniline dyes; it was first purposefully synthesized through deamination of a mix of aniline and its salts by a group of French chemists two years later. [22]

In 1872, diphenylamine was suggested as a means to detect nitrous acid in sulfuric acid due to its blue coloration in the presence of oxidizing agents. By 1875, it was also being used to detect nitrites and nitrates in drinking water. [23]

Toxicity

In animal experiments diphenylamine was rapidly and completely absorbed after ingestion by mouth. It underwent metabolism to sulfonyl and glucuronyl conjugates and was rapidly excreted mainly via urine. Acute oral and dermal toxicity were low. Diphenylamine can cause severe irritation to the eyes. It was not a skin irritant, and it has not been technically feasible to test acute toxicity study by inhalation. Diphenylamine targets the red blood cell system and can cause abnormal erythropoiesis in the spleen, and thus congestion of the spleen, and haemosiderosis. Changes in liver and kidneys were found upon longer exposure. [6] At clear toxic doses of parent animals reproductive effects were limited to reduced implantation sites in F1 females associated with reduced rat litter size, implicating a possible mutagenic or teratogenic effect. No effect on development could be attributed. [6] The U.S. CDC's NIOSH lists the following symptoms of poisoning: irritation eyes, skin, mucous membrane; eczema; tachycardia, hypertension; cough, sneezing; methemoglobinemia; increased blood pressure and heart rate; proteinuria, hematuria (blood in the urine), bladder injury; in animals: teratogenic effects. [24]

The short-term NOAEL of 9.6 – 10 mg/kg bw/day was derived from 90-day rat, 90-day dog and 1-year dog studies and the long-term NOAEL was 7.5 mg/kg bw/day. The Acceptable Daily Intake of diphenylamine was 0.075 mg/kg bw/day based on the 2-year rat study, applying a safety factor of 100; the Acceptable Operator Exposure Level was 0.1 mg/kg bw/day. [6]

In a study of diphenylamine metabolism in harvested and dipped apples at different time intervals it was observed that radiolabelled residues of diphenylamine penetrate from the surface into the pulp, which after 40 weeks contained 32% of the residue. Diphenylamine was always the major residue, but 3 metabolites were found in good amounts in the apple samples, whose identification experts considered insufficient.(Kim-Kang, H. 1993. Metabolism of 14C-diphenylamine in stored apples—nature of the residue in plants. Report RPT00124. Study XBL 91071. XenoBiotic Laboratories, Inc., USA, unpublished) cited in [6] [25] There is a data gap on presence or formation of nitrosamines in apple metabolism or during processing. [6] The carcinogen 4-Aminobiphenyl can accompany diphenylamine as an impurity. [24]

Diphenylamine has low acute and short-term toxicity to birds, but is very toxic to aquatic organisms. Risk to biological methods of sewage treatment was assessed as low. [6]

The impurity in commercial diphenylamine which induces polycystic kidney disease in rats was identified in 1981. Laboratory studies with highly purified diphenylamine indicated that the impurity can be formed by heating diphenylamine. [26]

Environmental fate

Diphenylamine is considered practically insoluble according to the 2014 MSDS. It exhibits very low persistence in direct water photolysis experiments in the laboratory and is moderately volatile. Indirect photooxidation in the atmosphere through reaction with hydroxyl radicals was estimated. Despite limited data, the information was sufficient for the EC to characterize the environmental risk as negligible, because the intended use of diphenylamine was indoors.

Residues in fruit and alternatives

Of 744 apples tested USDA found 82.7% of them to have diphenylamine residue between 0.005 - 4.3 ppm, below the U.S. EPA's tolerance level of 10ppm. [27] A number of alternatives to the use of diphenylamine exist for the control of scald of apples. [28]

Regulation

Europe

The EC set maximum residue levels for diphenylamine in 2005. (Annex II and Part B of Annex III to Regulation (EC) No 396/2005). Diphenylamine was one of 84 substances of a European Commission (EC) review program covered by a regulation from 2002 requiring the European Food Safety Authority (EFSA) upon EC request to organize a peer review of the initial evaluation, i.e. a draft risk assessment, and to provide the EC within 6 months with a conclusion. The assessment, received by the EFSA in 2007 started the peer review in October 2007 by dispatching it for consultation of the EC member states and the applicants, the two manufacturers, Cerexagri s.a., Italian subsidiary of United Phosphorus Ltd (UPL), and Pace International LLC. As a result of the peer review, mostly lacking data about risk to consumers, and particularly the levels and toxicity of unidentified metabolites of the substance, the possible formation of nitrosamines during storage of the active substance and during processing of treated apples, and the lack of data on the potential breakdown product of diphenylamine residues in processed commodities, the EC decided on 30 November 2009 to withdraw authorizations for plant protection products containing diphenylamine.(2009/859/EC)

The 'European Diphenylamine Task Force' resubmitted an application to the EC with more data, and an additional report was received by the EFSA on 3 December 2010. EFSA concluded the risk assessment did not eliminate the concerns on 5 December 2011, published this opinion in 2012 [29] and it became law in 2013. [30]

WHO/FAO joint committee

The committee established an acceptable daily intake of 0.02 mg/kg/day in a meeting on pesticide residues. [25]

US EPA

After passage of the Food Quality Protection Act (FQPA) of 1996, the U.S. EPA had established a tolerance level for apples at 10 ppm, and for meat and milk at 0 ppm. The tentative LOAEL was 10 mg/kg/day [31] In 1997 EPA approved the reregistration of diphenylamine, and determined that recommended tolerances met the safety standards under FQPA and that "adequate data indicate that tolerances for residues in milk and meat could be increased from 0.0 ppm and established as separate tolerances set at 0.01 ppm". [32] EPA has not reviewed diphenylamine since then.

Related Research Articles

<span class="mw-page-title-main">Phenothiazine</span> Heterocyclic compound containing a ring of four carbon, one nitrogen and one sulfur atom

Phenothiazine, abbreviated PTZ, is an organic compound that has the formula S(C6H4)2NH and is related to the thiazine-class of heterocyclic compounds. Derivatives of phenothiazine are highly bioactive and have widespread use and rich history.

<span class="mw-page-title-main">Acridine</span> Chemical compound

Acridine is an organic compound and a nitrogen heterocycle with the formula C13H9N. Acridines are substituted derivatives of the parent ring. It is a planar molecule that is structurally related to anthracene with one of the central CH groups replaced by nitrogen. Like the related molecules pyridine and quinoline, acridine is mildly basic. It is an almost colorless solid, which crystallizes in needles. There are few commercial applications of acridines; at one time acridine dyes were popular, but they are now relegated to niche applications, such as with acridine orange. The name is a reference to the acrid odour and acrid skin-irritating effect of the compound.

<span class="mw-page-title-main">Naphthalene</span> Chemical compound

Naphthalene is an organic compound with formula C
10H
8. It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. It is the main ingredient of traditional mothballs.

<span class="mw-page-title-main">Aniline</span> Organic compound (C₆H₅NH₂); simplest aromatic amine

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.

Acrylonitrile is an organic compound with the formula CH2CHCN and the structure H2C=CH−C≡N. It is a colorless, volatile liquid. It has a pungent odor of garlic or onions. Its molecular structure consists of a vinyl group linked to a nitrile. It is an important monomer for the manufacture of useful plastics such as polyacrylonitrile. It is reactive and toxic at low doses.

<i>p</i>-Phenylenediamine Chemical compound

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. 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.

<span class="mw-page-title-main">Nitrobenzene</span> Chemical compound

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.

<span class="mw-page-title-main">Imidacloprid</span> Chemical compound

Imidacloprid is a systemic insecticide belonging to a class of chemicals called the neonicotinoids which act on the central nervous system of insects. The chemical works by interfering with the transmission of stimuli in the insect nervous system. Specifically, it causes a blockage of the nicotinergic neuronal pathway. By blocking nicotinic acetylcholine receptors, imidacloprid prevents acetylcholine from transmitting impulses between nerves, resulting in the insect's paralysis and eventual death. It is effective on contact and via stomach action. Because imidacloprid binds much more strongly to insect neuron receptors than to mammal neuron receptors, this insecticide is more toxic to insects than to mammals.

<span class="mw-page-title-main">Hydroquinone</span> Chemical compound

Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a para position. It is a white granular solid. Substituted derivatives of this parent compound are also referred to as hydroquinones. The name "hydroquinone" was coined by Friedrich Wöhler in 1843.

<span class="mw-page-title-main">Phosphorus trichloride</span> Chemical compound

Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.

<span class="mw-page-title-main">Heptachlor</span> Chemical compound

Heptachlor is an organochlorine compound that was used as an insecticide. Usually sold as a white or tan powder, heptachlor is one of the cyclodiene insecticides. In 1962, Rachel Carson's Silent Spring questioned the safety of heptachlor and other chlorinated insecticides. Due to its highly stable structure, heptachlor can persist in the environment for decades. In the United States, the Environmental Protection Agency has limited the sale of heptachlor products to the specific application of fire ant control in underground transformers. The amount that can be present in different foods is regulated.

<span class="mw-page-title-main">Lead hydrogen arsenate</span> Chemical compound

Lead hydrogen arsenate, also called lead arsenate, acid lead arsenate or LA, chemical formula PbHAsO4, is an inorganic insecticide used primarily against the potato beetle. Lead arsenate was the most extensively used arsenical insecticide. Two principal formulations of lead arsenate were marketed: basic lead arsenate (Pb5OH(AsO4)3, CASN: 1327-31-7) and acid lead arsenate (PbHAsO4).

<span class="mw-page-title-main">Hydrogen selenide</span> Chemical compound

Hydrogen selenide is an inorganic compound with the formula H2Se. This hydrogen chalcogenide is the simplest and most commonly encountered hydride of selenium. H2Se is a colorless, flammable gas under standard conditions. It is the most toxic selenium compound with an exposure limit of 0.05 ppm over an 8-hour period. Even at extremely low concentrations, this compound has a very irritating smell resembling that of decayed horseradish or 'leaking gas', but smells of rotten eggs at higher concentrations.

Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.

Aziridine is an organic compound consisting of the three-membered heterocycle (CH2)2NH. It is a colorless, toxic, volatile liquid that is of significant practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its derivatives, also referred to as aziridines, are of broader interest in medicinal chemistry.

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.

<span class="mw-page-title-main">Ethoxyquin</span> Chemical compound

Ethoxyquin (EMQ) is a quinoline-based antioxidant used as a food preservative in certain countries and originally to control scald on pears after harvest. It is used as a preservative in some pet foods to slow the development of rancidity of fats. Ethoxyquin is also used in some spices to prevent color loss due to oxidation of the natural carotenoid pigments.

<span class="mw-page-title-main">Methoxychlor</span> Synthetic organochloride insecticide, now obsolete.

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<span class="mw-page-title-main">4-Nitrochlorobenzene</span> Chemical compound

4-Nitrochlorobenzene is the organic compound with the formula ClC6H4NO2. It is a pale yellow solid. 4-Nitrochlorobenzene is a common intermediate in the production of a number of industrially useful compounds, including antioxidants commonly found in rubber. Other isomers with the formula ClC6H4NO2 include 2-nitrochlorobenzene and 3-nitrochlorobenzene.

<span class="mw-page-title-main">Thiamethoxam</span> Chemical compound

Thiamethoxam is the ISO common name for a mixture of cis-trans isomers used as a systemic insecticide of the neonicotinoid class. It has a broad spectrum of activity against many types of insects and can be used as a seed dressing.

References

  1. 1 2 International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 671. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
  2. ↑ https://www.sigmaaldrich.com/Graphics/COfAInfo/SigmaSAPQM/SPEC/24/242586/242586-BULK_______SIAL_____.pdf [ bare URL PDF ]
  3. 1 2 3 4 5 6 NIOSH Pocket Guide to Chemical Hazards. "#0240". National Institute for Occupational Safety and Health (NIOSH).
  4. ↑ "Diphenylamine".
  5. 1 2 P. F. Vogt, J. J. Gerulis, "Amines, Aromatic" in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a02_037
  6. 1 2 3 4 5 6 7 "Conclusion on the peer review of the pesticide risk assessment of the active substance diphenylamine". EFSA Journal. 10: 2486. 25 January 2012. doi: 10.2903/j.efsa.2012.2486 .
  7. ↑ "Identification of toxic impurities in commercial Diphenylamine", Bulletin of Environmental Contamination and Toxicology, February 1977, Volume 17, Issue 2, pp 204–207. Authored by S Safe, O Hutzinger, JFS Crocker, SC Digout
  8. ↑ The Merck Index, 10th Ed., (1983), p.485, Rahway: Merck & Co.
  9. ↑ T. Kahl, K.-W. Schröder, F. R. Lawrence, W. J. Marshall, Hartmut Höke, Rudolf Jäckh, "Aniline" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH: Weinheim. doi : 10.1002/14356007.a02_303
  10. ↑ F. D. Hager (1941). "Triphenylamine". Organic Syntheses .; Collective Volume, vol. 1, p. 544
  11. ↑ Ingle, M; M. C. D'Souza (1989). "Physiology and control of superficial scald of apples: a review". HortScience. 24 (28): 31. doi: 10.21273/HORTSCI.24.1.28 . S2CID   89228904.
  12. ↑ Cook, Stanley G (1935). "Determination of Diphenylamine in Smokeless Powders". Industrial & Engineering Chemistry Analytical Edition. 7 (4): 250–255. doi:10.1021/ac50096a019.
  13. ↑ Leggett, Lana S; Lott, Peter F (1989). "Gunshot residue analysis via organic stabilizers and nitrocellulose". Microchemical Journal. 39: 76–85. doi: 10.1016/0026-265X(89)90012-X .
  14. ↑ Drzyzga, Oliver (2003). "Diphenylamine and derivatives in the environment: A review". Chemosphere. 53 (8): 809–818. Bibcode:2003Chmsp..53..809D. doi:10.1016/S0045-6535(03)00613-1. PMID   14505701.
  15. ↑ Jun Dong; Cyril A. Migdal (2009). "1. Antioxidants". In Leslie R. Rudnick (ed.). Lubricant Additives: Chemistry and Applications (2nd ed.). CRC Press. pp. 3–50. ISBN   978-1420059656.
  16. ↑ Canady, Richard; Richard Lane; Greg Paoli; Margaret Wilson; Heidi Bialk; Steven Hermansky; Brent Kobielush; Ji-Eun Lee; Craig Llewellyn; Joseph Scimeca (Oct 2013). "Determining the Applicability of Threshold of Toxicological Concern Approaches to Substances Found in Foods". Crit Rev Food Sci Nutr. 53 (12): 1239–1249. doi:10.1080/10408398.2012.752341. PMC   3809586 . PMID   24090142.
  17. ↑ Hans-Wilhelm Engels; Herrmann-Josef Weidenhaupt; Manfred Pieroth; Werner Hofmann; Karl-Hans Menting; Thomas Mergenhagen; Ralf Schmoll; Stefan Uhrlandt (2011). "Rubber, 9. Chemicals and Additives". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a23_365.pub3.
  18. ↑ Willard, H. H; Manalo, G. D (1947). "Derivatives of Diphenylamine as Oxidation-Reduction Indicators in Alkaline Solution". Analytical Chemistry. 19 (3): 167–170. doi:10.1021/ac60003a011.
  19. ↑ Sarver, L. A; Kolthoff, I. M (1931). "Diphenylamine Sulfonic Acid as a New Oxidation-Reduction Indicator". Journal of the American Chemical Society. 53 (8): 2902–2905. doi:10.1021/ja01359a010.
  20. ↑ Sarver, L. A; Kolthoff, I. M (1937). "Electrochemical Properties of Diphenylbenzidine Sulfonic Acid". Journal of the American Chemical Society. 59: 23–25. doi:10.1021/ja01280a007.
  21. ↑ Sriramam, K (1977). "Mechanistic interpretation of the redox behaviour of diphenylamine". Talanta. 24 (1): 31–36. doi:10.1016/0039-9140(77)80181-1. PMID   18962017.
  22. ↑ "The Chemical News and Journal of Industrial Science; with which is Incorporated the "Chemical Gazette.": A Journal of Practical Chemistry in All Its Applications to Pharmacy, Arts and Manufactures". 1866.
  23. ↑ Withers, W. A. (1911). "A MODIFICATION OF THE DIPHENYLAMINE TEST FOR NITROUS AND NITRIC ACIDS". Journal of the American Chemical Society . 33 (5): 708–711 – via ACS Publications.
  24. 1 2 "Diphenylamine". NIOSH Pocket Guide to Chemical Hazards. CDC NIOSH. 4 April 2011. Retrieved 29 April 2014.
  25. 1 2 fao (2007). "2007 JMPR Evaluation, Diphenylamine (030) 155-189" (PDF). Joint FAO/WHO Meeting on Pesticide Residues. WHO, FAO. pp. 1–35. Retrieved 29 April 2014.
  26. ↑ Clegg, S; Safe, S; Crocker, JF (1981). "Identification of a toxic impurity in commercial diphenylamine". J Environ Sci Health B. 16 (2): 125–30. doi:10.1080/03601238109372245. PMID   7252059.
  27. ↑ "Pesticide Data Program's Summary for calendar year 2010". USDA. p. 189. Retrieved 29 April 2014.
  28. ↑ Colin R. Little, Robert J. Holmes "Storage Technology for Apples and Pears: A Guide to Production, Postharvest Treatment and Storage of Pome Fruit in Australia" Institute for Horticultural Development Agriculture, 2000.
  29. ↑ "Conclusion on the peer review of the pesticide risk assessment of the active substance diphenylamine. European Food Safety Authority". EFSA Journal. 11 (3): 2486–2527. 2012. doi: 10.2903/j.efsa.2013.3130 .
  30. ↑ "European Commission Regulation No 772/2012, 8 August 2013, amending Annexes II, III and V to Regulation (EC) No 396/2005 of the European Parliament and of the Council as regards maximum residue levels for diphenylamine in or on certain products". Official Journal of the European Union: L 217/2. 12 March 2013.
  31. ↑ EPA (13 May 1999). "Diphenylamine; Pesticide Tolerance; 40 CFR Part 180" (PDF). Federal Register. 64 (92): 25842–25848. Retrieved 28 April 2014.
  32. ↑ "diphenylamine Tolerance Actions 11/01". Federal Register. 4 December 2011. Retrieved 29 April 2014.
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