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Oxidizing agent
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<h2 id="electron-acceptors">Electron acceptors</h2> <p><a href="/facts/Electron_acceptor/sRvhMXqH">Electron acceptors</a> participate in <a href="/facts/Electron-transfer_reactions/BIdASS9R">electron-transfer reactions</a>. In this context, the oxidizing agent is called an <i>electron acceptor</i> and the reducing agent is called an <i>electron donor</i>. A classic oxidizing agent is the <a href="/facts/Ferrocenium_tetrafluoroborate/RT2oFeh6">ferrocenium</a> ion Fe(C5H5)+2, which accepts an electron to form Fe(C5H5)2. One of the strongest acceptors commercially available is "<a href="/facts/Magic_blue/hbo706Xm">Magic blue</a>", the radical cation derived from N(C6H4-4-Br)3.<a class="footnote-ref" id="fnref:1" href="#fn:1"><sup>1</sup></a> </p><p>Extensive tabulations of ranking the electron accepting properties of various reagents (redox potentials) are available, see <a href="/facts/Standard_electrode_potential_(data_page)/SNnf8sw7">Standard electrode potential (data page)</a>. </p> <h2 id="atom-transfer-reagents">Atom-transfer reagents</h2> <p>In more common usage, an oxidizing agent transfers oxygen atoms to a substrate. In this context, the oxidizing agent can be called an oxygenation reagent or oxygen-atom transfer (OAT) agent.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a> Examples include MnO−4 (<a href="/facts/Permanganate/nJa04jVh">permanganate</a>), CrO2−4 (<a href="/facts/Chromate_ion/6xkFLIJw">chromate</a>), OsO4 (<a href="/facts/Osmium_tetroxide/cxmYVnFK">osmium tetroxide</a>), and especially ClO−4 (<a href="/facts/Perchlorate/WCC53zS2">perchlorate</a>). Notice that these species are all <a href="/facts/Oxide/DXtoVe1C">oxides</a>. </p><p>In some cases, these oxides can also serve as electron acceptors, as illustrated by the conversion of MnO−4 to MnO2−4,ie <a href="/facts/Permanganate/nJa04jVh">permanganate</a> to <a href="/facts/Manganate/3Kr1qk0S">manganate</a>. </p> <h3>Common oxidizing agents</h3> <ul><li><a href="/facts/Oxygen/acyn6o8r">Oxygen</a> (O2)</li> <li><a href="/facts/Ozone/o0E5gn2p">Ozone</a> (O3)</li> <li><a href="/facts/Hydrogen_peroxide/vju6HBIc">Hydrogen peroxide</a> (H2O2) and other inorganic <a href="/facts/Peroxide/VMU8y4xB">peroxides</a>, <a href="/facts/Fenton%2527s_reagent/gTBzVprG">Fenton's reagent</a></li> <li><a href="/facts/Fluorine/YUV0Fb8m">Fluorine</a> (F2), <a href="/facts/Chlorine/y27UwYBM">chlorine</a> (Cl2), and other <a href="/facts/Halogen/YeFgWHeA">halogens</a></li> <li><a href="/facts/Nitric_acid/UDbwGp6s">Nitric acid</a> (HNO3) and <a href="/facts/Nitrate/5AnVlYnL">nitrate</a> compounds such as <a href="/facts/Potassium_nitrate/TycqMdcG">potassium nitrate</a> (KNO3), the oxidizer in <a href="/facts/Black_powder/AEcB6HCR">black powder</a></li> <li><a href="/facts/Potassium_chlorate/rARLS99c">Potassium chlorate</a> (KClO3)</li> <li><a href="/facts/Xenon_difluoride/vKS7zojD">Xenon difluoride</a> (XeF2)</li> <li><a href="/facts/Xenon_tetrafluoride/blYIn0x7">Xenon tetrafluoride</a> (XeF4)</li> <li><a href="/facts/Xenon_hexafluoride/QU16jh1g">Xenon hexafluoride</a> (XeF6)</li> <li><a href="/facts/Krypton_difluoride/q2tWYnHF">Krypton difluoride</a> (KrF2)</li> <li><a href="/facts/Sulfur/IK0amTfM">Sulfur</a> (S8)</li> <li><a href="/facts/Peroxydisulfuric_acid/nVJNTaEG">Peroxydisulfuric acid</a> (H2S2O8)</li> <li><a href="/facts/Peroxymonosulfuric_acid/kI1oC4JL">Peroxymonosulfuric acid</a> (H2SO5)</li> <li><a href="/facts/Hypochlorite/XMJdjAEM">Hypochlorite</a>, <a href="/facts/Chlorite/EYtQI4wC">chlorite</a>, <a href="/facts/Chlorate/Ypne0mrY">chlorate</a>, <a href="/facts/Perchlorate/WCC53zS2">perchlorate</a>, and other analogous <a href="/facts/Halogen/YeFgWHeA">halogen</a> oxyanions</li> <li>Fluorides of <a href="/facts/Chlorine_fluoride/aQY5M6l6">chlorine</a>, <a href="/facts/Bromine_fluoride/v8mLp6R6">bromine</a>, and <a href="/facts/Iodine_fluoride/3rHuWb2X">iodine</a></li> <li>Hexavalent <a href="/facts/Chromium/6sVk6Uu7">chromium</a> compounds such as <a href="/facts/Chromic_acid/jukMaHzR">chromic and dichromic acids and chromium trioxide</a>, <a href="/facts/Pyridinium_chlorochromate/j4azJNy3">pyridinium chlorochromate</a> (PCC), and <a href="/facts/Chromate_and_dichromate/6xkFLIJw">chromate/dichromate</a> compounds such as <a href="/facts/Sodium_dichromate/UyVCRsul">Sodium dichromate</a> (Na2Cr2O7)</li> <li><a href="/facts/Permanganate/nJa04jVh">Permanganate</a> compounds such as <a href="/facts/Potassium_permanganate/nyjjuDlo">potassium permanganate</a> (KMnO4)</li> <li><a href="/facts/Sodium_perborate/rNw3Hnst">Sodium perborate</a> ([Na+]2·[B2O4(OH)4]2−)</li> <li><a href="/facts/Nitrous_oxide/Jvys91lI">Nitrous oxide</a> (N2O), <a href="/facts/Nitrogen_dioxide/FoLvApPI">Nitrogen dioxide</a>/<a href="/facts/Dinitrogen_tetroxide/01WfnHJh">Dinitrogen tetroxide</a> (NO2 / N2O4)</li> <li><a href="/facts/Sodium_bismuthate/ck4qg0PQ">Sodium bismuthate</a> (NaBiO3)</li> <li>Cerium (IV) compounds such as <a href="/facts/Ceric_ammonium_nitrate/PorTxSBS">ceric ammonium nitrate</a> and <a href="/facts/Ceric_sulfate/eSagjum1">ceric sulfate</a></li> <li><a href="/facts/Lead_dioxide/dQb52eNu">Lead dioxide</a> (PbO2)</li></ul> <h2 id="dangerous-materials-definition">Dangerous materials definition</h2> <p class="note">See also: <a href="/facts/HAZMAT_Class_5_Oxidizing_agents_and_organic_peroxides/CpubabN1">HAZMAT Class 5 Oxidizing agents and organic peroxides</a></p> <p>The <a href="/facts/Dangerous_goods/mfe6Yv43">dangerous goods</a> definition of an oxidizing agent is a substance that can cause or contribute to the combustion of other material.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> By this definition some materials that are classified as oxidizing agents by analytical chemists are not classified as oxidizing agents in a dangerous materials sense. An example is <a href="/facts/Potassium_dichromate/MwRzD3gW">potassium dichromate</a>, which does not pass the dangerous goods test of an oxidizing agent. </p><p>The <a href="/facts/U.S._Department_of_Transportation/qgNCJ1tF">U.S. Department of Transportation</a> defines oxidizing agents specifically. There are two definitions for oxidizing agents governed under DOT regulations. These two are <a href="/facts/HAZMAT_Class_5_Oxidizing_agents_and_organic_peroxides/CpubabN1">Class 5</a>; Division 5.1(a)1 and Class 5; Division 5.1(a)2. Division 5.1 "means a material that may, generally by yielding oxygen, cause or enhance the combustion of other materials." Division 5.(a)1 of the DOT code applies to solid oxidizers "if, when tested in accordance with the UN Manual of Tests and Criteria (IBR, see § 171.7 of this subchapter), its mean burning time is less than or equal to the burning time of a 3:7 potassium bromate/cellulose mixture." 5.1(a)2 of the DOT code applies to liquid oxidizers "if, when tested in accordance with the UN Manual of Tests and Criteria, it spontaneously ignites or its mean time for a pressure rise from 690 kPa to 2070 kPa gauge is less than the time of a 1:1 nitric acid (65 percent)/cellulose mixture."<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> </p> <h2 id="common-oxidizing-agents-and-their-products">Common oxidizing agents and their products</h2> <table><tbody><tr><th>Agent</th><th>Product(s)</th></tr><tr><td>O2 <a href="/facts/Oxygen/acyn6o8r">oxygen</a></td><td>Various, including the oxides H2O and CO2</td></tr><tr><td>O3 <a href="/facts/Ozone/o0E5gn2p">ozone</a></td><td>Various, including ketones, aldehydes, and H2O; see <a href="/facts/Ozonolysis/WEwBID8x">ozonolysis</a></td></tr><tr><td>F2 <a href="/facts/Fluorine/YUV0Fb8m">fluorine</a></td><td>F−</td></tr><tr><td>Cl2 <a href="/facts/Chlorine/y27UwYBM">chlorine</a></td><td>Cl−</td></tr><tr><td>Br2 <a href="/facts/Bromine/oLfj3C7D">bromine</a></td><td>Br−</td></tr><tr><td>I2 <a href="/facts/Iodine/JlfMecMf">iodine</a></td><td>I−, I−3</td></tr><tr><td>ClO− <a href="/facts/Hypochlorite/XMJdjAEM">hypochlorite</a></td><td>Cl−, H2O</td></tr><tr><td>ClO−3 <a href="/facts/Chlorate/Ypne0mrY">chlorate</a></td><td>Cl−, H2O</td></tr><tr><td>HNO3 <a href="/facts/Nitric_acid/UDbwGp6s">nitric acid</a></td><td>NO <a href="/facts/Nitric_oxide/UvhdvDzp">nitric oxide</a> (Dilute nitric acid)NO2 <a href="/facts/Nitrogen_dioxide/FoLvApPI">nitrogen dioxide</a> (Concentrated nitric acid)</td></tr><tr><td>H2SO4(<i>l</i>) <a href="/facts/Sulfuric_acid/Wom6fymJ">Concentrated sulphuric acid</a><p>SO3 <a href="/facts/Sulfur_trioxide/Ijvm08Lq">Sulphur trioxide</a></p></td><td>SO2 Sulphur dioxide (non-aqueous)<p>H2SO3 <a href="/facts/Sulfurous_acid/2qtYNHAB">Sulphurous acid</a> (In aqueous solution) </p></td></tr><tr><td>SO2 <a href="/facts/Sulfur_dioxide/jDK1fIDs">sulfur dioxide</a></td><td>S <a href="/facts/Sulfur/IK0amTfM">sulfur</a>(<a href="/facts/Claus_process/FbhagLPm">Claus process</a>, <a href="/facts/Ultramarine/2oMnJC4R">ultramarine</a> production, more commonly reducing agent)</td></tr><tr><td>Hexavalent chromiumCrO3 <a href="/facts/Chromium_trioxide/ENafKcAm">chromium trioxide</a>CrO2−4 <a href="/facts/Chromate_ion/6xkFLIJw">chromate</a> Cr2O2−7 <a href="/facts/Dichromate/6xkFLIJw">dichromate</a></td><td>Cr3+, H2O</td></tr><tr><td>MnO−4 <a href="/facts/Permanganate/nJa04jVh">permanganate</a>MnO2−4 <a href="/facts/Manganate/3Kr1qk0S">manganate</a></td><td>Mn2+ (acidic) orMnO2 (basic)</td></tr><tr><td>Ag+ ion <a href="/facts/Silver/xXe41BGg">Silver</a> ion</td><td>Ag (Metal)</td></tr><tr><td>SbF5 <a href="/facts/Antimony_pentafluoride/nTqasUkK">antimony pentafluoride</a></td><td>SbF6− <a href="/facts/Hexafluoroantimonate/nTqasUkK">hexafluoroantimonate</a> or SbF3 <a href="/facts/Antimony_trifluoride/qog3FLWA">antimony trifluoride</a></td></tr><tr><td>PtF6 <a href="/facts/Platinum_hexafluoride/Nqqdd4Xc">platinum hexafluoride</a></td><td>PtF6− <a href="/facts/Hexafluoroplatinate/TNWH9SmX">hexafluoroplatinate</a></td></tr><tr><td>RuO4 <a href="/facts/Ruthenium_tetroxide/tEpyQYR5">ruthenium tetroxide</a>OsO4 <a href="/facts/Osmium_tetroxide/cxmYVnFK">osmium tetroxide</a></td><td>in organic lab scale synthesis</td></tr><tr><td>H2O2, other <a href="/facts/Peroxide/VMU8y4xB">peroxides</a></td><td>Various, including oxides and H2O</td></tr><tr><td>Tl(III) <a href="/facts/Thallium/v35pGMJB">thallic</a> compounds</td><td>Tl(I) thallous compounds, in organic lab scale synthesis</td></tr></tbody></table> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/Combustion/ohQoWj8z">Combustion</a> – Chemical reaction between a fuel and oxygen</li> <li><a href="/facts/Electron_acceptor/sRvhMXqH">Electron acceptor</a> – Chemical entity capable of accepting electrons</li> <li><a href="/facts/Electron_donor/7JxwwW43">Electron donor</a> – Chemical entity capable of donating electrons to another entity</li> <li><a href="/facts/Electrosynthesis/hzU3XYxC">Electrosynthesis</a> – Synthesis of chemical compounds in an electrochemical cell</li> <li><a href="/facts/Organic_oxidation/6DdmXG4S">Organic oxidation</a> – Redox reaction that takes place with organic compoundsPages displaying short descriptions of redirect targets</li> <li><a href="/facts/Organic_redox_reaction/6DdmXG4S">Organic redox reaction</a> – Redox reaction that takes place with organic compounds</li> <li><a href="/facts/Reducing_agent/CtfSGVXC">Reducing agent</a> – Chemical species that donates an electron to another species in a redox reaction</li> <li><a href="/facts/Solvated_electron/mLplrtI8">Solvated electron</a> – Free electron in a solution, often liquid ammonia</li></ul> <h2 id="external-links">External links</h2> <ul><li> Media related to Oxidizing agents at Wikimedia Commons</li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>N. G. Connelly, W. E. Geiger (1996). "Chemical Redox Agents for Organometallic Chemistry". Chemical Reviews. 96 (2): 877–910. doi:10.1021/cr940053x. PMID 11848774. <a href="/wiki/Chemical_Reviews" target="_blank">/wiki/Chemical_Reviews</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN 978-0-471-72091-1 <a href="978-0-471-72091-1" target="_blank">978-0-471-72091-1</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Australian Dangerous Goods Code, 6th Edition <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>49 CFR 172.127 General Requirements for Shipments and Packagings; Subpart D <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> </ol>