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{{chembox |
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| verifiedrevid = 414430862 |
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| verifiedrevid = 443695502 |
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| Name = Diphenylamine |
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| ImageFile = Diphenylamine.png |
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| Name = Diphenylamine |
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| ImageFile = Diphenylamine 200.svg |
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| ImageName = Skeletal formula |
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| ImageName = Skeletal formula |
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| ImageFile1 = Diphenylamine-3D-balls.png |
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| ImageFile1 = Diphenylamine-3D-balls.png |
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| ImageSize1 = 240px |
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| ImageName1 = Ball-and-stick model |
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| ImageSize1 = 240px |
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| ImageName1 = Ball-and-stick model |
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| PIN = ''N''-Phenylaniline<ref name="IUPAC2014">{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=671 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> |
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| IUPACName = Diphenylamine |
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| OtherNames = N-Phenylbenzenamine;<br /> N-Phenyl Aniline;<br /> DPA;<br /> Anilinobenzene;<br /> (phenylamino)benzene;<br /> N,N-diphenylamine;<br /> big dipper;<br /> C.I. 10355;<br /> Phenylbenzenamine;<br /> Diphenylamine; |
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| OtherNames = (Diphenyl)amine<br />Diphenylamine (deprecated<ref name="IUPAC2014"/>)<br />Diphenylazane<br />''N''-Phenylbenzenamine<br />Anilinobenzene<br />(Phenylamino)benzene<br />''N'',''N''-Diphenylamine<br /> C.I. 10355<br /> Phenylbenzenamine |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 4640 |
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| ChEBI = 4640 |
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| SMILES = c1ccc(cc1)Nc2ccccc2 |
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| SMILES = c1ccc(cc1)Nc2ccccc2 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 11003 |
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| ChemSpiderID = 11003 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = DMBHHRLKUKUOEG-UHFFFAOYSA-N |
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| StdInChIKey = DMBHHRLKUKUOEG-UHFFFAOYSA-N |
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| Abbreviations = DPA |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 122-39-4 |
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| CASNo = 122-39-4 |
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| RTECS = 9 |
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| RTECS = JJ7800000 |
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| PubChem = 11487 |
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| EC_number = 204-539-4 |
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| UNNumber = 2811 3077 |
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| Beilstein = 508755 |
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| Gmelin = 67833 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>12</sub>H<sub>11</sub>N |
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| Formula = C<sub>12</sub>H<sub>11</sub>N |
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| MolarMass = 169.23 g/mol |
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| MolarMass = 169.23 g/mol |
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| Appearance = White, off-white<ref>https://www.sigmaaldrich.com/Graphics/COfAInfo/SigmaSAPQM/SPEC/24/242586/242586-BULK_______SIAL_____.pdf {{Bare URL PDF|date=March 2022}}</ref> |
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| Appearance = White ] |
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| Odor = Floral<ref name=PGCH/> |
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| Density = 1.2 g/cm³ |
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| Density = 1.2 g/cm<sup>3</sup> |
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| Solubility = Slightly |
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| Solubility = 0.03%<ref name=PGCH/> |
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| MeltingPt = 53 °C (326 K) |
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| MeltingPtC = 53 |
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| BoilingPt = 302 °C (575 K) |
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| MeltingPt_notes = |
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| BoilingPtC = 302 |
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| BoilingPt_notes = |
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| pKa = 0.79<ref>{{Cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Diphenylamine#section=Dissociation-Constants | title=Diphenylamine}}</ref> |
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| VaporPressure = 1 mmHg (108°C)<ref name=PGCH/> |
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| MagSus = -109.7·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| MainHazards = Toxic. Possible mutagen. Possible teratogen. Harmful in contact with skin, and if swallowed or inhaled. Irritant. |
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| MainHazards = Toxic. Possible mutagen. Possible ]. Harmful in contact with skin, and if swallowed or inhaled. Irritant. |
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| NFPA-H = 3 |
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| NFPA-H = 3 |
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| NFPA-R = 0 |
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| NFPA-R = 0 |
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| NFPA-F = 1 |
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| NFPA-F = 1 |
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| FlashPt = 152°C |
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| FlashPtC = 152 |
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| GHSPictograms = {{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}} |
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| RPhrases = R23 R24 R25 R33 R50 R53 |
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| GHSSignalWord = Danger |
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| SPhrases = S36 S37 S45 S60 S61 |
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| HPhrases = {{H-phrases|301|311|319|331|373|410}} |
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| PPhrases = {{P-phrases|260|261|264|270|271|273|280|301+310|302+352|304+340|305+351+338|311|312|314|321|322|330|337+313|361|363|391|403+233|405|501}} |
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| PEL = none<ref name=PGCH>{{PGCH|0240}}</ref> |
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| IDLH = N.D.<ref name=PGCH/> |
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| REL = TWA 10 mg/m<sup>3</sup><ref name=PGCH/> |
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}} |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| Function = ] |
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| OtherFunction_label = ] |
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| OtherFunctn = ] |
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| OtherFunction = ] |
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'''Diphenylamine''' is the ] with the ] (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>NH. It is a colourless solid, but samples are often yellow due to oxidized impurities.<ref name=Ullmann>P. F. Vogt, J. J. Gerulis, “Amines, Aromatic” in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim.</ref> |
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'''Diphenylamine''' is an ] with the ] (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>NH. The compound is a derivative of ], consisting of an ] bound to two ] groups. The compound is a colorless solid, but commercial samples are often yellow due to oxidized impurities.<ref name=Ullmann_aromatic_amines>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}}</ref> Diphenylamine dissolves well in many common organic solvents, and is moderately soluble in water.<ref name=efsa>{{Cite journal|title=Conclusion on the peer review of the pesticide risk assessment of the active substance diphenylamine|journal=EFSA Journal|volume=10|pages=2486| doi=10.2903/j.efsa.2012.2486|date=25 January 2012|doi-access=free}}</ref> It is used mainly for its ] properties. Diphenylamine is widely used as an industrial ], ] ] and ] and is also employed in agriculture as a ] and ].<ref>{{cite journal | url=https://link.springer.com/article/10.1007/BF01685551 | doi=10.1007/BF01685551 | title=Identification of toxic impurities in commercial Diphenylamine | date=1977 | last1=Safe | first1=S. | last2=Hutzinger | first2=O. | last3=Crocker | first3=J. F. S. | last4=Digout | first4=S. C. | journal=Bulletin of Environmental Contamination and Toxicology | volume=17 | issue=2 | pages=204–207 | pmid=843636 | bibcode=1977BuECT..17..204S }}</ref> |
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==Preparation and reactivity== |
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==Preparation and reactivity== |
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Diphenylamine is manufactured by the thermal deamination of ] over oxide ]s: |
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Diphenylamine is produced by the thermal deamination of ] over oxide ]s: |
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: 2 C<sub>6</sub>H<sub>5</sub>NH<sub>2</sub> → (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>NH + NH<sub>3</sub> |
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: 2 C<sub>6</sub>H<sub>5</sub>NH<sub>2</sub> → (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>NH + NH<sub>3</sub> |
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It is a weak base, with a ''K''<sub>b</sub> of 10<sup>−14</sup>. With strong acids, it forms the water soluble salt. |
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It is a weak base, with a ''K''<sub>b</sub> of 10<sup>−14</sup>. With strong acids, it forms salts. For example, treatment with ] gives the bisulfate <sup>+</sup><sup>−</sup> as a white or yellowish powder with m.p. 123-125 °C.<ref name = Merck>''The Merck Index, 10th Ed.'', (1983), p.485, Rahway: Merck & Co.</ref> |
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Diphenylamine undergoes various cyclisation reactions. With ], it gives ], a precursor to pharmaceuticals.<ref>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}}</ref> |
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: (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>NH + 2 S → S(C<sub>6</sub>H<sub>4</sub>)<sub>2</sub>NH + H<sub>2</sub>S |
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With iodine, it undergoes dehydrogenation to give ], with release of ]: |
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: (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>NH + I<sub>2</sub> → (C<sub>6</sub>H<sub>4</sub>)<sub>2</sub>NH + 2 HI |
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] with ] gives ].<ref>{{OrgSynth | author = F. D. Hager| title = Triphenylamine| collvol = 1 | collvolpages = 544 | year = 1941 | prep = CV1P0544}}</ref> it is also used as a test reagent in the dische's test . |
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==Applications== |
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==Applications== |
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Diphenylamine is used as a pre- or postharvest scald inhibitor for apples. Its anti-scald activity is the result of its antioxidant properties, which protect the apple skin from the oxidation products of alpha-farnesene during storage.<ref>"Apple Scald, a Complex Problem" |
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===Testing for DNA=== |
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W.J. Bramlage |
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The ] uses diphenylamine to test for ], and can be used to distinguish DNA from RNA. |
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(University of Massachusetts Department of Plant and Soil Sciences) |
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===Apple scald inhibitor=== |
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Post Harvest Pomology Newsletter, 6(2): 11-14 |
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Diphenylamine is used as a pre- or postharvest ] inhibitor for apples applied as an indoor drench treatment. Its anti-scald activity is the result of its antioxidant properties, which protect the ] skin from the oxidation products of α-] during storage.<ref name=horti>{{cite journal|last=Ingle|first=M|author2=M. C. D'Souza|title=Physiology and control of superficial scald of apples: a review|journal=HortScience|date=1989|volume=24|issue=28|pages=31|doi=10.21273/HORTSCI.24.1.28|s2cid=89228904|doi-access=free}}</ref> ] is physical injury that manifests in brown spots after fruit is removed from cold storage. |
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September 1988 http://postharvest.tfrec.wsu.edu/pgDisplay.php?article=N6I2C</ref> |
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===Stabilizer for smokeless powder=== |
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Diphenylamine derivatives are also useful. Ring-alkylated derivatives of diphenylamine are used as "antiozinates" in the manufacture of rubber products, reflecting the antioxidant nature of aniline derivatives. The compound undergoes various cyclisaton reactions. With ], it gives ], a precursor to certain pharmaceuticals.<ref>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.</ref> |
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In the manufacture of ], diphenylamine is commonly used as a stabilizer,<ref>{{cite journal | doi = 10.1021/ac50096a019| title = Determination of Diphenylamine in Smokeless Powders| journal = Industrial & Engineering Chemistry Analytical Edition| volume = 7| issue = 4| pages = 250–255| year = 1935| last1 = Cook| first1 = Stanley G}}</ref> such that the ] analysis seeks to quantify traces of diphenylamine.<ref>{{cite journal | doi = 10.1016/0026-265X(89)90012-X| title = Gunshot residue analysis via organic stabilizers and nitrocellulose| journal = Microchemical Journal| volume = 39| pages = 76–85| year = 1989| last1 = Leggett| first1 = Lana S| last2 = Lott| first2 = Peter F| doi-access = free}}</ref> Diphenylamine functions by binding nitrogen oxide degradation products, forming compounds like ]. In this way, DPA prevents these degradation products from accelerating further degradation.<ref>{{cite journal | doi = 10.1016/S0045-6535(03)00613-1| pmid = 14505701| title = Diphenylamine and derivatives in the environment: A review| journal = Chemosphere| volume = 53| issue = 8| pages = 809–818| year = 2003| last1 = Drzyzga| first1 = Oliver| bibcode = 2003Chmsp..53..809D}}</ref> |
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: (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>NH + 2 S → S(C<sub>6</sub>H<sub>4</sub>)<sub>2</sub>NH + H<sub>2</sub>S |
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With iodine, it cyclises to ]: |
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: (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>NH + I<sub>2</sub> → (C<sub>6</sub>H<sub>4</sub>)<sub>2</sub>NH + 2 ] |
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] with ] gives ].<ref>{{OrgSynth | author = F. D. Hager| title = Triphenylamine| collvol = 1 | collvolpages = 544 | year = 1941 | prep = CV1P0544}}</ref> |
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===Antioxidant=== |
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Diphenylamine finds niche use as a test for ] (see ]). |
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Alkylated diphenylamines function as ] in lubricants,<ref>{{cite book | title = Lubricant Additives: Chemistry and Applications | edition = 2nd | editor = Leslie R. Rudnick | author1 = Jun Dong | author2 = Cyril A. Migdal | chapter = 1. Antioxidants | pages = 3–50 | publisher = CRC Press | year = 2009 | isbn = 978-1420059656}}</ref> approved for use in machines, in which contact with food is not ruled out.<ref>{{cite journal|last=Canady|first=Richard |author2=Richard Lane |author3=Greg Paoli |author4=Margaret Wilson |author5=Heidi Bialk |author6=Steven Hermansky |author7=Brent Kobielush |author8=Ji-Eun Lee |author9=Craig Llewellyn |author10=Joseph Scimeca|title=Determining the Applicability of Threshold of Toxicological Concern Approaches to Substances Found in Foods|journal=Crit Rev Food Sci Nutr|date=Oct 2013|volume=53|issue=12|pages=1239–1249|doi=10.1080/10408398.2012.752341| pmc=3809586 |pmid=24090142}}</ref> Alkylated diphenylamines and other derivatives are used as ]s in the manufacture of rubber products, reflecting the antioxidant nature of aniline derivatives.<ref name=Ullmann_aromatic_amines/><ref>{{Ullmann | author1 = Hans-Wilhelm Engels | author2 = Herrmann-Josef Weidenhaupt | author3 = Manfred Pieroth | author4 = Werner Hofmann | author5 = Karl-Hans Menting | author6 = Thomas Mergenhagen | author7 = Ralf Schmoll | author8 = Stefan Uhrlandt | title = Rubber, 9. Chemicals and Additives | doi = 10.1002/14356007.a23_365.pub3 | year = 2011}}</ref> |
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===Redox indicator=== |
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Many diphenylamine derivatives are used as ]s that are particularly useful in alkaline redox titrations.<ref>{{cite journal | doi = 10.1021/ac60003a011| title = Derivatives of Diphenylamine as Oxidation-Reduction Indicators in Alkaline Solution| journal = Analytical Chemistry| volume = 19| issue = 3| pages = 167–170| year = 1947| last1 = Willard| first1 = H. H| last2 = Manalo| first2 = G. D}}</ref> The diphenylaminesulfonic acid is a simple prototype redox indicator, owing to its improved aqueous solubility compared with diphenylamine.<ref>{{cite journal | doi = 10.1021/ja01359a010| title = Diphenylamine Sulfonic Acid as a New Oxidation-Reduction Indicator| journal = Journal of the American Chemical Society| volume = 53| issue = 8| pages = 2902–2905| year = 1931| last1 = Sarver| first1 = L. A| last2 = Kolthoff| first2 = I. M}}</ref> Attempts have been made to explain the color changes associated with the oxidation of diphenylamine.<ref>{{cite journal | doi = 10.1021/ja01280a007| title = Electrochemical Properties of Diphenylbenzidine Sulfonic Acid| journal = Journal of the American Chemical Society| volume = 59| pages = 23–25| year = 1937| last1 = Sarver| first1 = L. A| last2 = Kolthoff| first2 = I. M}}</ref><ref>{{cite journal | doi = 10.1016/0039-9140(77)80181-1| pmid = 18962017| title = Mechanistic interpretation of the redox behaviour of diphenylamine| journal = Talanta| volume = 24| issue = 1| pages = 31–36| year = 1977| last1 = Sriramam| first1 = K}}</ref> |
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In a related application, diphenylamine is oxidized by nitrate to give a similar blue coloration in the ]. |
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===Dyes === |
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Several ]s like ], ], and ] are ] of diphenylamine. It is also used as a ]. A dye mordant is any substance that helps dyes to adhere to fabrics. |
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==History== |
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Diphenylamine was discovered by ] in 1864 amongst the products of ] 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.<ref>{{cite web | url=https://books.google.com/books?id=zwUAAAAAMAAJ&pg=RA1-PA63 | title=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 | year=1866 }}</ref> |
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In 1872, diphenylamine was suggested as a means to detect ] in ] due to its blue coloration in the presence of ]. By 1875, it was also being used to detect ] and ] in drinking water.<ref>{{Cite journal |last=Withers |first=W. A. |date=1911 |title=A Modification of the Diphenylamine Test for Nitrous and Nitric Acids |url=https://pubs.acs.org/doi/abs/10.1021/ja02218a008 |journal=] |volume=33 |issue=5 |pages=708–711 |doi=10.1021/ja02218a008 |via=ACS Publications}}</ref> |
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{{section-stub|date=July 2022}} |
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In 1924, diphenylamine is discovered to be useful in detecting DNA via the ] by ]. |
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==Toxicity== |
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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 ] system and can cause abnormal ] in the spleen, and thus congestion of the spleen, and ]. Changes in liver and kidneys were found upon longer exposure.<ref name=efsa /> 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.<ref name=efsa /> The U.S. CDC's ] 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.<ref name=NIOSH>{{cite web|title=Diphenylamine|url=https://www.cdc.gov/niosh/npg/npgd0240.html|website=NIOSH Pocket Guide to Chemical Hazards|publisher=CDC NIOSH|access-date=29 April 2014|date=4 April 2011}}</ref> |
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The short-term ] 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. |
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The ] 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.<ref name=efsa /> |
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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 <ref name=efsa /><ref name=WHO /> There is a data gap on presence or formation of nitrosamines in apple metabolism or during processing.<ref name=efsa /> The carcinogen ] can accompany diphenylamine as an impurity.<ref name=NIOSH /> |
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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.<ref name=efsa /> |
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The impurity in commercial diphenylamine which induces ] in ] was identified in 1981. Laboratory studies with highly purified diphenylamine indicated that the impurity can be formed by heating diphenylamine.<ref>{{cite journal| pmid=7252059 | doi=10.1080/03601238109372245 | volume=16 | title=Identification of a toxic impurity in commercial diphenylamine | year=1981 | journal=J Environ Sci Health B | pages=125–30 | last1 = Clegg | first1 = S | last2 = Safe | first2 = S | last3 = Crocker | first3 = JF| issue=2 | bibcode=1981JESHB..16..125C }}</ref> |
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==Environmental fate== |
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Diphenylamine is considered practically insoluble according to the 2014 MSDS. It exhibits very low persistence in direct water ] 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. |
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===Residues in fruit and alternatives=== |
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Of 744 apples tested ] 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. |
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<ref name=USDA>{{cite web|title=Pesticide Data Program's Summary for calendar year 2010|url=http://www.ams.usda.gov/AMSv1.0/getfile?dDocName=stelprdc5098549|publisher=USDA|access-date=29 April 2014|page=189}}{{Dead link|date=December 2024 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> A number of alternatives to the use of diphenylamine exist for the control of scald of apples.<ref>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.</ref> |
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==Regulation== |
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===Europe=== |
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The EC set ]s 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 ] (EC) review program covered by a regulation from 2002 requiring the ] (EFSA) upon EC request to organize a peer review of the initial evaluation, i.e. a draft ], 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) |
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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 <ref name=efsa2012>{{Cite journal|title=Conclusion on the peer review of the pesticide risk assessment of the active substance diphenylamine. European Food Safety Authority|journal=EFSA Journal|volume=11|issue=3|pages=2486–2527|year=2012|doi=10.2903/j.efsa.2013.3130|doi-access=free}}</ref> and it became law in 2013.<ref name=EC2013>{{cite journal|title=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|journal=Official Journal of the European Union|url=https://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2013:217:0001:0027:EN:PDF|date=12 March 2013|volume=|issue= |pages=L 217/2}}</ref> |
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===WHO/FAO joint committee=== |
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The committee established an ] of 0.02 mg/kg/day in a meeting on pesticide residues.<ref name=WHO>{{cite web|last=fao|title=2007 JMPR Evaluation, Diphenylamine (030) 155-189|url=http://www.fao.org/fileadmin/templates/agphome/documents/Pests_Pesticides/JMPR/Evaluation01/07_Diphenylamine.pdf|website=Joint FAO/WHO Meeting on Pesticide Residues|publisher=WHO, FAO|access-date=29 April 2014|pages=1–35|year=2007}}</ref> |
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===US EPA=== |
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After passage of the ] (FQPA) of 1996, the U.S. ] 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 <ref name=epa99>{{cite journal|title=Diphenylamine; Pesticide Tolerance; 40 CFR Part 180|journal=Federal Register|date= 13 May 1999 |volume=64|issue=92|pages=25842–25848 |url=http://www.gpo.gov/fdsys/pkg/FR-1999-05-13/pdf/99-12135.pdf|access-date=28 April 2014|author=EPA}}</ref> 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".<ref name="FR 2001">{{cite web|title=diphenylamine Tolerance Actions 11/01|url=http://pmep.cce.cornell.edu/profiles/herb-growthreg/dalapon-ethephon/diphenylamine/diphenylamine_tol_1101.html|publisher=Federal Register|access-date=29 April 2014|date=4 December 2011}}</ref> EPA has not reviewed diphenylamine since then. |
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==References== |
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==References== |
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{{reflist|30em}} |
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<references/> |
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==External links== |
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==External links== |
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