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class="vector-toc-numb">2</span> <span>Classification</span> </div> </a> <ul id="toc-Classification-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Sources_and_occurrence" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Sources_and_occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Sources and occurrence</span> </div> </a> <button aria-controls="toc-Sources_and_occurrence-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Sources and occurrence subsection</span> </button> <ul id="toc-Sources_and_occurrence-sublist" class="vector-toc-list"> <li id="toc-Naphthenic_acid_corrosion" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Naphthenic_acid_corrosion"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Naphthenic acid corrosion</span> </div> </a> <ul id="toc-Naphthenic_acid_corrosion-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Metal_naphthenates" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Metal_naphthenates"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Metal naphthenates</span> </div> </a> <ul id="toc-Metal_naphthenates-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Environmental_impact" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Environmental_impact"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Environmental impact</span> </div> </a> <ul id="toc-Environmental_impact-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header 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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Naphthenic acid</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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href="https://de.wikipedia.org/wiki/Naphthens%C3%A4uren" title="Naphthensäuren – German" lang="de" hreflang="de" data-title="Naphthensäuren" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9D%CE%B1%CF%86%CE%B8%CE%B5%CE%BD%CE%B9%CE%BA%CF%8C_%CE%BF%CE%BE%CF%8D" title="Ναφθενικό οξύ – Greek" lang="el" hreflang="el" data-title="Ναφθενικό οξύ" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%86%D9%81%D8%AA%D9%86%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="نفتنیک اسید – Persian" lang="fa" hreflang="fa" data-title="نفتنیک اسید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Acide_napht%C3%A9nique" title="Acide naphténique – French" lang="fr" hreflang="fr" data-title="Acide naphténique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%86%D5%A1%D5%BE%D5%A9%D5%A5%D5%B6%D5%A1%D5%A9%D5%A9%D5%B8%D6%82" title="Նավթենաթթու – Armenian" lang="hy" hreflang="hy" data-title="Նավթենաթթու" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Acido_naftenico" title="Acido naftenico – Italian" lang="it" hreflang="it" data-title="Acido naftenico" 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<div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Naphthenic acid </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Naphthens%C3%A4ure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/Naphthens%C3%A4ure.svg/200px-Naphthens%C3%A4ure.svg.png" decoding="async" width="200" height="67" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/Naphthens%C3%A4ure.svg/300px-Naphthens%C3%A4ure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/28/Naphthens%C3%A4ure.svg/400px-Naphthens%C3%A4ure.svg.png 2x" data-file-width="425" data-file-height="142" /></a></span><br /><div style="text-align:center;">Example component of naphthenic acid</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=1338-24-5">1338-24-5</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.014.239">100.014.239</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q1964898#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>215-662-8</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/20849290">20849290</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/YNM5U6B7A4">YNM5U6B7A4</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID1027394">DTXSID1027394</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q1964898#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>Variable  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>Variable    </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-pollu.svg" class="mw-file-description" title="GHS09: Environmental hazard"><img alt="GHS09: Environmental hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/50px-GHS-pictogram-pollu.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/75px-GHS-pictogram-pollu.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/100px-GHS-pictogram-pollu.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Warning</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H317: May cause an allergic skin reaction">H317</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H335: May cause respiratory irritation">H335</abbr>, <abbr class="abbr" title="H411: Toxic to aquatic life with long lasting effects">H411</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</abbr>, <abbr class="abbr" title="P272: Contaminated work clothing should not be allowed out of the workplace.">P272</abbr>, <abbr class="abbr" title="P273: Avoid release to the environment.">P273</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P312: Call a POISON CENTER or doctor/physician if you feel unwell.">P312</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P332+P313: If skin irritation occurs: Get medical advice/attention.">P332+P313</abbr>, <abbr class="abbr" title="P333+P313: If skin irritation or a rash occurs: Get medical advice/attention.">P333+P313</abbr>, <abbr class="abbr" title="P337+P313: If eye irritation persists: Get medical advice/attention.">P337+P313</abbr>, <abbr class="abbr" title="P362: Take off contaminated clothing.">P362</abbr>, <abbr class="abbr" title="P363: Wash contaminated clothing before reuse.">P363</abbr>, <abbr class="abbr" title="P391: Collect spillage.">P391</abbr>, <abbr class="abbr" title="P403+P233: Store in a well ventilated place. Keep container tightly closed.">P403+P233</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>101 °C (214 °F; 374 K) </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Naphthenic acids</b> (<b>NAs</b>) are mixtures of several <a href="/wiki/Cyclopentane" title="Cyclopentane">cyclopentyl</a> and <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexyl</a> carboxylic acids with molecular weights of 120 to well over 700 <a href="/wiki/Atomic_mass_unit" class="mw-redirect" title="Atomic mass unit">atomic mass units</a>. The main <a href="/wiki/Fraction_(chemistry)" title="Fraction (chemistry)">fractions</a> are carboxylic acids with a carbon backbone of 9 to 20 carbons. McKee et al. claim that "naphthenic acids (NAs) are primarily cycloaliphatic carboxylic acids with 10 to 16 carbons",<sup id="cite_ref-McKee_1-0" class="reference"><a href="#cite_note-McKee-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> although acids containing up to 50 carbons have been identified in heavy petroleum.<sup id="cite_ref-robbins-2001_2-0" class="reference"><a href="#cite_note-robbins-2001-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Naphthenic_acid&action=edit&section=1" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Naphthenic acid can refer to derivatives and isomers of <a href="/wiki/1-Naphthoic_acid" title="1-Naphthoic acid">naphthalene carboxylic acids</a>. In the petrochemical industry, NA's refer to alkyl carboxylic acids found in petroleum.<sup id="cite_ref-Barros_3-0" class="reference"><a href="#cite_note-Barros-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The term naphthenic acid has roots in the somewhat archaic term "naphthene" (cycloaliphatic but non-aromatic) used to classify hydrocarbons. It was originally used to describe the complex mixture of petroleum-based acids when the analytical methods available in the early 1900s could identify only a few naphthene-type components with accuracy. Today "naphthenic" acid is used in a more generic sense to refer to all of the carboxylic acids present in petroleum,<sup id="cite_ref-McKee_1-1" class="reference"><a href="#cite_note-McKee-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> whether cyclic, acyclic, or aromatic compounds, and carboxylic acids containing heteroatoms such as N and S. Although commercial naphthenic acids often contain a majority of cycloaliphatic acids, multiple studies<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:0_5-0" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> have shown they also contain straight chain and branched aliphatic acids and aromatic acids; some naphthenic acids contain >50% combined aliphatic and aromatic acids. </p><p>Salts of naphthenic acids, called <b>naphthenates</b>, are widely used as hydrophobic sources of metal ions in diverse applications.<sup id="cite_ref-:1_6-0" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Classification">Classification</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Naphthenic_acid&action=edit&section=2" title="Edit section: Classification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Naphthenic acids are represented by a general formula C<sub>n</sub>H<sub>2n-z</sub>O<sub>2</sub>, where <i>n</i> indicates the carbon number and <i>z</i> specifies a homologous series. The <i>z</i> is equal to 0 for saturated, acyclic acids and increases to 2 in monocyclic naphthenic acids, to 4 in bicyclic naphthenic acids, to 6 in tricyclic acids, and to 8 in tetracyclic acids.<sup id="cite_ref-:0_5-1" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Crude oils with total acid number (TAN) as little as 0.5 mg KOH/g acid or petroleum fractions greater than about 1.0 mg KOH/g oil usually qualify as a high acid crude or oil. At the 1.0 mg/g TAN level, acidic crude oils begin to be heavily discounted in value and so are referred to as opportunity crudes.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Commercial grades of naphthenic acid are most often recovered from kerosene/jet fuel and diesel fractions, where their corrosivity<sup id="cite_ref-:1_6-1" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> and negative impact on burning qualities require their removal. Naphthenic acids are also a major contaminant in water produced during the extraction of oil from <a href="/wiki/Athabasca_oil_sands" title="Athabasca oil sands">Athabasca oil sands</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Sources_and_occurrence">Sources and occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Naphthenic_acid&action=edit&section=3" title="Edit section: Sources and occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Naphthenic acids are extracted from petroleum distillates by <a href="/wiki/Extraction_(chemistry)" title="Extraction (chemistry)">extraction</a> with aqueous base. Acidification of this extract <a href="/wiki/Neutralization_(chemistry)" title="Neutralization (chemistry)">acidic neutralization</a> returns the acids free from hydrocarbons. Naphthenic acid is removed from petroleum fractions not only to minimize corrosion but also to recover commercially useful products.<sup id="cite_ref-KO_10-0" class="reference"><a href="#cite_note-KO-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Some crude oils are high in acidic compounds (up to 4%).<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Naphthenic_acid_corrosion">Naphthenic acid corrosion</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Naphthenic_acid&action=edit&section=4" title="Edit section: Naphthenic acid corrosion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The composition varies with the crude oil composition and the conditions during refining and oxidation..<sup id="cite_ref-Barros_3-1" class="reference"><a href="#cite_note-Barros-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Fractions that are rich in naphthenic acids can cause corrosion damage to <a href="/wiki/Oil_refinery" title="Oil refinery">oil refinery</a> equipment; the phenomenon of <i>naphthenic acid corrosion</i> (NAC).<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Crude oils with a high content of naphthenic acids are often referred to as high <a href="/wiki/Total_acid_number" title="Total acid number">total acid number</a> (TAN) crude oils or high acid crude oil (HAC). </p> <div class="mw-heading mw-heading2"><h2 id="Metal_naphthenates">Metal naphthenates</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Naphthenic_acid&action=edit&section=5" title="Edit section: Metal naphthenates"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As the greatest current and historical usage, naphthenic acid are used to produce <b>metal naphthenates</b>.<sup id="cite_ref-KO_10-1" class="reference"><a href="#cite_note-KO-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Metal naphthenates are referred often to as "salts" of naphthenic acids, but metal naphthenates are not ionic. They are covalent, hydrophobic <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complexes</a>. More specifically they are <a href="/wiki/Metal_carboxylate_complex" class="mw-redirect" title="Metal carboxylate complex">metal carboxylate complexes</a> with the formula M(naphthenate)<sub>2</sub>, or M<sub>3</sub>O(naphthenate)<sub>6</sub> for basic oxides. Metal naphthenates are not well defined in conventional chemical sense because they are a complex mixture rather than a specific single component, structure or formula. They have diverse applications.<sup id="cite_ref-:1_6-2" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>The naphthenates have industrial applications including synthetic <a href="/wiki/Detergent" title="Detergent">detergents</a>, <a href="/wiki/Lubricant" title="Lubricant">lubricants</a>, corrosion inhibitors, fuel and lubricating oil additives, <a href="/wiki/Wood_preservative" class="mw-redirect" title="Wood preservative">wood preservatives</a>, <a href="/wiki/Insecticide" title="Insecticide">insecticides</a>, <a href="/wiki/Fungicide" title="Fungicide">fungicides</a>, <a href="/wiki/Acaricide" title="Acaricide">acaricides</a>, <a href="/wiki/Wetting_agent" class="mw-redirect" title="Wetting agent">wetting agents</a>, <a href="/wiki/Thickening_agent" title="Thickening agent">thickening agent</a> of <a href="/wiki/Napalm" title="Napalm">napalm</a> and <a href="/wiki/Oil_drying_agent" title="Oil drying agent">oil drying agents</a> used in painting and wood surface treatment. Industrially useful naphthenates include those of aluminium, magnesium, calcium, barium, cobalt, copper, lead, manganese, nickel, vanadium, and zinc.<sup id="cite_ref-:1_6-3" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Illustrative is the use of cobalt naphthenate for the oxidation of tetrahydronaphthalene to the hydroperoxide.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>The complex mixture and hydrophobic nature of naphthenic acid allows metal naphthenates to be highly soluble in organic media such as petroleum-based hydrocarbons, oftentimes much more so than single isomer carboxylates such as metal acetates and stearates. Their industrial applications exploits this property, where they are used as oil-borne <a href="/wiki/Detergent" title="Detergent">detergents</a>, <a href="/wiki/Lubricant" title="Lubricant">lubricants</a>, corrosion inhibitors, fuel and lubricating oil additives, <a href="/wiki/Wood_preservative" class="mw-redirect" title="Wood preservative">wood preservatives</a>, <a href="/wiki/Insecticide" title="Insecticide">insecticides</a>, <a href="/wiki/Fungicide" title="Fungicide">fungicides</a>, <a href="/wiki/Acaricide" title="Acaricide">acaricides</a>, <a href="/wiki/Wetting_agent" class="mw-redirect" title="Wetting agent">wetting agents</a>, <a href="/wiki/Oil_drying_agent" title="Oil drying agent">oil drying agents</a> (driers) used in oil-based paint and wood surface treatment including <a href="/wiki/Varnish" title="Varnish">varnish</a>. Industrially useful metal naphthenates include those of aluminum, barium, calcium, cobalt, copper, iron, lead, magnesium manganese, nickel, potassium, vanadium, zinc, and zirconium.<sup id="cite_ref-:0_5-2" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Environmental_impact">Environmental impact</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Naphthenic_acid&action=edit&section=6" title="Edit section: Environmental impact"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Naphthenic acids are the major contaminant in water produced from the extraction of oil from <a href="/wiki/Athabasca_oil_sands" title="Athabasca oil sands">Athabasca oil sands</a> (AOS).<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>It has been stated that "naphthenic acids are the most significant environmental contaminants resulting from petroleum extraction from oil sands deposits." Nonetheless, the same authors suggest that "under worst-case exposure conditions, acute toxicity is unlikely in wild mammals exposed to naphthenic acids in AOS tailings pond water, but repeated exposure may have adverse health effects."<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Naphthenic acids are present in Athabasca oil sands and <a href="/wiki/Syncrude_Tailings_Dam" title="Syncrude Tailings Dam">tailings pond</a> water at an estimated concentration of 81 mg/L<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Using <a href="/wiki/Organisation_for_Economic_Co-operation_and_Development" class="mw-redirect" title="Organisation for Economic Co-operation and Development">Organisation for Economic Co-operation and Development</a> [OECD] protocols for testing toxicity, refined NAs are not acutely <a href="/wiki/Genotoxicity" title="Genotoxicity">genotoxic</a> to mammals.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Damage, however, induced by NAs while transient in acute or discontinuous exposure, may be cumulative in repeated exposure.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>Naphthenic acids have both acute and chronic toxicity to fish and other organisms.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Naphthenic_acid&action=edit&section=7" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxylic acid</a></li> <li><a href="/wiki/Organic_acid" title="Organic acid">Organic acid</a></li> <li><a href="/wiki/Resin_acid" title="Resin acid">Resin acid</a></li> <li><a href="/wiki/Paraffinic" class="mw-redirect" title="Paraffinic">Paraffinic</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Naphthenic_acid&action=edit&section=8" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-McKee-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-McKee_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-McKee_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output 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W. (2008). <a rel="nofollow" class="external text" href="http://www.deadducklake.com/wp-content/uploads/2009/04/tailingsallen.pdf">"Process water treatment in Canada's oil sands industry: I. Target pollutants and treatment objectives"</a> <span class="cs1-format">(PDF)</span>. <i>Journal of Environmental Engineering and Science</i>. <b>7</b> (2): 123–138. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1139%2FS07-038">10.1139/S07-038</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Environmental+Engineering+and+Science&rft.atitle=Process+water+treatment+in+Canada%27s+oil+sands+industry%3A+I.+Target+pollutants+and+treatment+objectives&rft.volume=7&rft.issue=2&rft.pages=123-138&rft.date=2008&rft_id=info%3Adoi%2F10.1139%2FS07-038&rft.au=Allen%2C+E.+W.&rft_id=http%3A%2F%2Fwww.deadducklake.com%2Fwp-content%2Fuploads%2F2009%2F04%2Ftailingsallen.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANaphthenic+acid" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Naphthenic_acid&action=edit&section=9" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://www.ogj.com/articles/save_screen.cfm?ARTICLE_ID=323174">Article concerning refining crude oil with a high content of naphthenic acids</a></li> <li><a rel="nofollow" class="external text" href="https://www.reuters.com/article/sphereNews/idUSSP4245320070607?sp=true&view=sphere">Crude oils with a high content of naphthenic acids in China's refineries</a></li> <li><a rel="nofollow" class="external text" href="http://www.aiche.org/uploadedFiles/FPD/MemberCenter/AiCHE-103g-SmartApproachAcidCrude.pdf">Crude oils containing naphthenic acids in the Grangemouth refinery</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20080528051600/http://www.coqg.org/20050127Naphthenic%20Acids.pdf">Overview of naphthenic acid corrosion</a></li> <li><a rel="nofollow" class="external text" href="http://www.nace.org/nacestore/assets/ConferencePapers/1999/99378.pdf">Literature survey of naphthenic acid corrosion</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20080528051559/http://www.coqg.org/20060223TAN%20Merichem.pdf">Removing naphthenic acids from the crude oil</a></li> <li><a rel="nofollow" class="external text" href="http://www.aiche-chicago.org/symposium06/haynes.pdf">Presentation by Nalco on naphthenic acid corrosion</a></li> <li><a rel="nofollow" class="external text" href="http://www.aiche-chicago.org/symposium06/rechtien.pdf">Presentation by Baker Petrolite on naphthenic acid corrosion</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20080528051601/http://www.coqg.org/20030130High%20Acid%20Crudes.pdf">Presentation by ChevronTexaco on crude oils with a high content of naphthenic acids</a></li> <li><a rel="nofollow" class="external text" href="http://www.setlaboratories.com/nac.htm">Information by Seth Laboratories on Naphthenic acid corrosion</a></li> <li><a rel="nofollow" class="external text" href="http://www.arabschool.org/pdf_notes/20_REFINING_OF_KUWAITS_HEAVY_CRUDE_OIL.pdf">Details regarding Kuwaitian heavy crudes and naphthenic acid corrosion</a></li> <li><a rel="nofollow" class="external text" href="http://www.scielo.br/scielo.php?script=sci_arttext&pid=S1516-14392007000200021&lng=em&nrm=iso&tlng=em">Article regarding naphthenic acid removal</a></li> <li><a rel="nofollow" class="external text" href="http://www.warwick.ac.uk/staff/M.P.Barrow/petroleum.html">Article regarding naphthenic acid species</a></li> <li><a rel="nofollow" class="external text" href="http://cat.inist.fr/?aModele=afficheN&cpsidt=18562696">Article abstract regarding molecular origins of heavy crude oil interfacial activity mainly caused by Naphthenic acids</a></li> <li><a rel="nofollow" class="external text" href="https://www.osti.gov/bridge/servlets/purl/825290-2UYSHV/native/825290.pdf">Article about processes to remove Naphthenic acids</a></li> <li><a rel="nofollow" class="external text" href="http://www.che.ncsu.edu/kilpatrick/papers/jdst.25.253.pdf">Article about stabilisation of water-in-oil emulsions by naphthenic acids</a></li> <li><a rel="nofollow" class="external text" href="http://ecommons.txstate.edu/cgi/viewcontent.cgi?article=1000&context=bchemtad">Spectrometric Identification of Naphthenic Acids Isolated from Crude Oil</a></li> <li><a rel="nofollow" class="external text" href="http://www.ionscience.com/Portals/0/docs/Papers/NACE%2006436.pdf">Hydrogen flux and naphthenic acid corrosion</a></li></ul>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; 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