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 antiozonants 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. It is also used as a dye mordant. A dye mordant is any substance that helps dyes to adhere to fabrics.

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]

In 1924, diphenylamine is discovered to be useful in detecting DNA via the Dische test by Zacharias Dische.

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">Phenol</span> Organic compound (C6H5OH)

Phenol is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.

<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.

Bromomethane, commonly known as methyl bromide, is an organobromine compound with formula CH3Br. This colorless, odorless, nonflammable gas is produced both industrially and biologically. It is a recognized ozone-depleting chemical. It was used extensively as a pesticide until being phased out by most countries in the early 2000s. From a chemistry perspective, it is one of the halomethanes.

<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.

<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 aromatic nitro compound and the simplest of the nitrobenzenes, 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">Cyclohexanol</span> Chemical compound

Cyclohexanol is the organic compound with the formula HOCH(CH2)5. The molecule is related to cyclohexane by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid with a camphor-like odor, which, when very pure, melts near room temperature. Millions of tonnes are produced annually, mainly as a precursor to nylon.

<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">Biphenyl</span> Chemical compound

Biphenyl is an organic compound that forms colorless crystals. Particularly in older literature, compounds containing the functional group consisting of biphenyl less one hydrogen may use the prefixes xenyl or diphenylyl.

<span class="mw-page-title-main">Ethylbenzene</span> Hydrocarbon compound; precursor to styrene and polystyrene

Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as a reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.

<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">Bromine pentafluoride</span> Chemical compound

Bromine pentafluoride, BrF5, is an interhalogen compound and a fluoride of bromine. It is a strong fluorinating agent.

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

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.

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">Arsenic pentoxide</span> Chemical compound

Arsenic pentoxide is the inorganic compound with the formula As2O5. This glassy, white, deliquescent solid is relatively unstable, consistent with the rarity of the As(V) oxidation state. More common, and far more important commercially, is arsenic(III) oxide (As2O3). All inorganic arsenic compounds are highly toxic and thus find only limited commercial applications.

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

Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.

<span class="mw-page-title-main">Benzene</span> Hydrocarbon compound

Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon.

<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.

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. ↑ Safe, S.; Hutzinger, O.; Crocker, J. F. S.; Digout, S. C. (1977). "Identification of toxic impurities in commercial Diphenylamine". Bulletin of Environmental Contamination and Toxicology. 17 (2): 204–207. Bibcode:1977BuECT..17..204S. doi:10.1007/BF01685551. PMID   843636.
  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 ; Collected Volumes, 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. ISBN   978-3527306732.
  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. doi:10.1021/ja02218a008 – 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. Bibcode:1981JESHB..16..125C. 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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