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id="toc-Chemical_reactions-sublist" class="vector-toc-list"> <li id="toc-Decomposition" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Decomposition"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Decomposition</span> </div> </a> <ul id="toc-Decomposition-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactant" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reactant"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Reactant</span> </div> </a> <ul id="toc-Reactant-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Addition_to_alkenes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Addition_to_alkenes"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Addition to alkenes</span> </div> </a> <ul id="toc-Addition_to_alkenes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Formic_acid_anhydride" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Formic_acid_anhydride"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>Formic acid anhydride</span> </div> </a> <ul id="toc-Formic_acid_anhydride-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Production" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Production"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Production</span> </div> </a> <button aria-controls="toc-Production-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 Production subsection</span> </button> <ul id="toc-Production-sublist" class="vector-toc-list"> <li id="toc-From_methyl_formate_and_formamide" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#From_methyl_formate_and_formamide"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>From methyl formate and formamide</span> </div> </a> <ul id="toc-From_methyl_formate_and_formamide-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Niche_and_obsolete_chemical_routes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Niche_and_obsolete_chemical_routes"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Niche and obsolete chemical routes</span> </div> </a> <ul id="toc-Niche_and_obsolete_chemical_routes-sublist" class="vector-toc-list"> <li id="toc-By-product_of_acetic_acid_production" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#By-product_of_acetic_acid_production"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2.1</span> <span>By-product of acetic acid production</span> </div> </a> <ul id="toc-By-product_of_acetic_acid_production-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydrogenation_of_carbon_dioxide" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Hydrogenation_of_carbon_dioxide"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2.2</span> <span>Hydrogenation of carbon dioxide</span> </div> </a> <ul id="toc-Hydrogenation_of_carbon_dioxide-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Oxidation_of_biomass" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Oxidation_of_biomass"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2.3</span> <span>Oxidation of biomass</span> </div> </a> <ul id="toc-Oxidation_of_biomass-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Laboratory_methods" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Laboratory_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2.4</span> <span>Laboratory methods</span> </div> </a> <ul id="toc-Laboratory_methods-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Electrochemical_production" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Electrochemical_production"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2.5</span> <span>Electrochemical production</span> </div> </a> <ul id="toc-Electrochemical_production-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Uses</span> </div> </a> <button aria-controls="toc-Uses-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 Uses subsection</span> </button> <ul id="toc-Uses-sublist" class="vector-toc-list"> <li id="toc-Agriculture" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Agriculture"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Agriculture</span> </div> </a> <ul id="toc-Agriculture-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Energy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Energy"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Energy</span> </div> </a> <ul id="toc-Energy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Soldering" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Soldering"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Soldering</span> </div> </a> <ul id="toc-Soldering-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chromatography" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chromatography"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Chromatography</span> </div> </a> <ul id="toc-Chromatography-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_uses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.5</span> <span>Other uses</span> </div> </a> <ul id="toc-Other_uses-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-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">8</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">9</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">10</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 vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Formic 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. Available in 71 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-71" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">71 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Mieresuur" title="Mieresuur – Afrikaans" lang="af" hreflang="af" data-title="Mieresuur" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AD%D9%85%D8%B6_%D8%A7%D9%84%D9%81%D9%88%D8%B1%D9%85%D9%8A%D9%83" title="حمض الفورميك – Arabic" lang="ar" hreflang="ar" data-title="حمض الفورميك" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Qar%C4%B1%C5%9Fqa_tur%C5%9Fusu" title="Qarışqa turşusu – Azerbaijani" lang="az" hreflang="az" data-title="Qarışqa turşusu" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%B3%DB%8C%D8%AF_%D9%81%D8%B1%D9%85%DB%8C%DA%A9" title="اسید فرمیک – South Azerbaijani" lang="azb" hreflang="azb" data-title="اسید فرمیک" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Hi%C4%81-sng" title="Hiā-sng – Minnan" lang="nan" hreflang="nan" data-title="Hiā-sng" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9C%D1%83%D1%80%D0%B0%D1%88%D1%8B%D0%BD%D0%B0%D1%8F_%D0%BA%D1%96%D1%81%D0%BB%D0%B0%D1%82%D0%B0" title="Мурашыная кіслата – Belarusian" lang="be" hreflang="be" data-title="Мурашыная кіслата" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9C%D1%80%D0%B0%D0%B2%D1%87%D0%B5%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Мравчена киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Мравчена киселина" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Mravlja_kiselina" title="Mravlja kiselina – Bosnian" lang="bs" hreflang="bs" data-title="Mravlja kiselina" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/%C3%80cid_f%C3%B2rmic" title="Àcid fòrmic – Catalan" lang="ca" hreflang="ca" data-title="Àcid fòrmic" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Kyselina_mraven%C4%8D%C3%AD" title="Kyselina mravenčí – Czech" lang="cs" hreflang="cs" data-title="Kyselina mravenčí" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Asid_fformig" title="Asid fformig – Welsh" lang="cy" hreflang="cy" data-title="Asid fformig" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Myresyre" title="Myresyre – Danish" lang="da" hreflang="da" data-title="Myresyre" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://de.wikipedia.org/wiki/Ameisens%C3%A4ure" title="Ameisensäure – German" lang="de" hreflang="de" data-title="Ameisensäure" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Metaanhape" title="Metaanhape – Estonian" lang="et" hreflang="et" data-title="Metaanhape" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9C%CF%85%CF%81%CE%BC%CE%B7%CE%BA%CE%B9%CE%BA%CF%8C_%CE%BF%CE%BE%CF%8D" title="Μυρμηκικό οξύ – Greek" lang="el" hreflang="el" data-title="Μυρμηκικό οξύ" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/%C3%81cido_f%C3%B3rmico" title="Ácido fórmico – Spanish" lang="es" hreflang="es" data-title="Ácido fórmico" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Formiata_acido" title="Formiata acido – Esperanto" lang="eo" hreflang="eo" data-title="Formiata acido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Azido_formiko" title="Azido formiko – Basque" lang="eu" hreflang="eu" data-title="Azido formiko" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%81%D8%B1%D9%85%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="فرمیک اسید – Persian" lang="fa" hreflang="fa" data-title="فرمیک 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_m%C3%A9thano%C3%AFque" title="Acide méthanoïque – French" lang="fr" hreflang="fr" data-title="Acide méthanoïque" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Aig%C3%A9ad_formach" title="Aigéad formach – Irish" lang="ga" hreflang="ga" data-title="Aigéad formach" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/%C3%81cido_f%C3%B3rmico" title="Ácido fórmico – Galician" lang="gl" hreflang="gl" data-title="Ácido fórmico" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8F%BC%EC%82%B0" title="폼산 – Korean" lang="ko" hreflang="ko" data-title="폼산" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%84%D6%80%D5%BB%D5%B6%D5%A1%D5%A9%D5%A9%D5%B8%D6%82" title="Մրջնաթթու – Armenian" lang="hy" hreflang="hy" data-title="Մրջնաթթու" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AB%E0%A5%89%E0%A4%B0%E0%A5%8D%E0%A4%AE%E0%A4%BF%E0%A4%95_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="फॉर्मिक अम्ल – Hindi" lang="hi" hreflang="hi" data-title="फॉर्मिक अम्ल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Mravlja_kiselina" title="Mravlja kiselina – Croatian" lang="hr" hreflang="hr" data-title="Mravlja kiselina" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asam_format" title="Asam format – Indonesian" lang="id" hreflang="id" data-title="Asam format" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Mauras%C3%BDra" title="Maurasýra – Icelandic" lang="is" hreflang="is" data-title="Maurasýra" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Acido_formico" title="Acido formico – Italian" lang="it" hreflang="it" data-title="Acido formico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%97%D7%95%D7%9E%D7%A6%D7%94_%D7%A4%D7%95%D7%A8%D7%9E%D7%99%D7%AA" title="חומצה פורמית – Hebrew" lang="he" hreflang="he" data-title="חומצה פורמית" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D2%9A%D2%B1%D0%BC%D1%8B%D1%80%D1%81%D2%9B%D0%B0_%D2%9B%D1%8B%D1%88%D2%9B%D1%8B%D0%BB%D1%8B" title="Құмырсқа қышқылы – Kazakh" lang="kk" hreflang="kk" data-title="Құмырсқа қышқылы" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9A%D1%83%D0%BC%D1%83%D1%80%D1%81%D0%BA%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0%D1%81%D1%8B" title="Кумурска кислотасы – Kyrgyz" lang="ky" hreflang="ky" data-title="Кумурска кислотасы" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Acidum_formicum" title="Acidum formicum – Latin" lang="la" hreflang="la" data-title="Acidum formicum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Skudrsk%C4%81be" title="Skudrskābe – Latvian" lang="lv" hreflang="lv" data-title="Skudrskābe" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Methansaier" title="Methansaier – Luxembourgish" lang="lb" hreflang="lb" data-title="Methansaier" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-li mw-list-item"><a href="https://li.wikipedia.org/wiki/Aomezeikzoer" title="Aomezeikzoer – Limburgish" lang="li" hreflang="li" data-title="Aomezeikzoer" data-language-autonym="Limburgs" data-language-local-name="Limburgish" class="interlanguage-link-target"><span>Limburgs</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Hangyasav" title="Hangyasav – Hungarian" lang="hu" hreflang="hu" data-title="Hangyasav" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9C%D1%80%D0%B0%D0%B2%D1%98%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Мравја киселина – Macedonian" lang="mk" hreflang="mk" data-title="Мравја киселина" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%AB%E0%B5%8B%E0%B5%BC%E0%B4%AE%E0%B4%BF%E0%B4%95%E0%B5%8D_%E0%B4%85%E0%B4%AE%E0%B5%8D%E0%B4%B2%E0%B4%82" title="ഫോർമിക് അമ്ലം – Malayalam" lang="ml" hreflang="ml" data-title="ഫോർമിക് അമ്ലം" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Asid_formik" title="Asid formik – Malay" lang="ms" hreflang="ms" data-title="Asid formik" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Mierenzuur" title="Mierenzuur – Dutch" lang="nl" hreflang="nl" data-title="Mierenzuur" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AE%E9%85%B8" title="ギ酸 – Japanese" lang="ja" hreflang="ja" data-title="ギ酸" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Maursyre" title="Maursyre – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Maursyre" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Maursyre" title="Maursyre – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Maursyre" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-om mw-list-item"><a href="https://om.wikipedia.org/wiki/Asiidii_foormiik" title="Asiidii foormiik – Oromo" lang="om" hreflang="om" data-title="Asiidii foormiik" data-language-autonym="Oromoo" data-language-local-name="Oromo" class="interlanguage-link-target"><span>Oromoo</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Chumoli_kislota" title="Chumoli kislota – Uzbek" lang="uz" hreflang="uz" data-title="Chumoli kislota" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwas_mr%C3%B3wkowy" title="Kwas mrówkowy – Polish" lang="pl" hreflang="pl" data-title="Kwas mrówkowy" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/%C3%81cido_metanoico" title="Ácido metanoico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido metanoico" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Acid_formic" title="Acid formic – Romanian" lang="ro" hreflang="ro" data-title="Acid formic" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-qu mw-list-item"><a href="https://qu.wikipedia.org/wiki/Sisi_p%27uchqu" title="Sisi p'uchqu – Quechua" lang="qu" hreflang="qu" data-title="Sisi p'uchqu" data-language-autonym="Runa Simi" data-language-local-name="Quechua" class="interlanguage-link-target"><span>Runa Simi</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9C%D1%83%D1%80%D0%B0%D0%B2%D1%8C%D0%B8%D0%BD%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Муравьиная кислота – Russian" lang="ru" hreflang="ru" data-title="Муравьиная кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Formic_acid" title="Formic acid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Formic acid" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Kyselina_mrav%C4%8Dia" title="Kyselina mravčia – Slovak" lang="sk" hreflang="sk" data-title="Kyselina mravčia" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Mravljin%C4%8Dna_kislina" title="Mravljinčna kislina – Slovenian" lang="sl" hreflang="sl" data-title="Mravljinčna kislina" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%9C%D1%80%D0%B0%D0%B2%D1%99%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Мравља киселина – Serbian" lang="sr" hreflang="sr" data-title="Мравља киселина" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Mravlja_kiselina" title="Mravlja kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Mravlja kiselina" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Asam_format" title="Asam format – Sundanese" lang="su" hreflang="su" data-title="Asam format" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Muurahaishappo" title="Muurahaishappo – Finnish" lang="fi" hreflang="fi" data-title="Muurahaishappo" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Myrsyra" title="Myrsyra – Swedish" lang="sv" hreflang="sv" data-title="Myrsyra" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Asidong_pormiko" title="Asidong pormiko – Tagalog" lang="tl" hreflang="tl" data-title="Asidong pormiko" data-language-autonym="Tagalog" data-language-local-name="Tagalog" class="interlanguage-link-target"><span>Tagalog</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AE%BE%E0%AE%AE%E0%AE%BF%E0%AE%95%E0%AF%8D_%E0%AE%85%E0%AE%AE%E0%AE%BF%E0%AE%B2%E0%AE%AE%E0%AF%8D" title="பாமிக் அமிலம் – Tamil" lang="ta" hreflang="ta" data-title="பாமிக் அமிலம்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%AB%E0%B0%BE%E0%B0%B0%E0%B1%8D%E0%B0%AE%E0%B0%BF%E0%B0%95%E0%B1%8D_%E0%B0%86%E0%B0%AE%E0%B1%8D%E0%B0%B2%E0%B0%82" title="ఫార్మిక్ ఆమ్లం – Telugu" lang="te" hreflang="te" data-title="ఫార్మిక్ ఆమ్లం" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%81%E0%B8%A3%E0%B8%94%E0%B8%9F%E0%B8%AD%E0%B8%A3%E0%B9%8C%E0%B8%A1%E0%B8%B4%E0%B8%81" title="กรดฟอร์มิก – Thai" lang="th" hreflang="th" data-title="กรดฟอร์มิก" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Formik_asit" title="Formik asit – Turkish" lang="tr" hreflang="tr" data-title="Formik asit" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9C%D1%83%D1%80%D0%B0%D1%88%D0%B8%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Мурашина кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Мурашина кислота" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Acid_formic" title="Acid formic – Vietnamese" lang="vi" hreflang="vi" data-title="Acid formic" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E7%94%B2%E9%85%B8" title="甲酸 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="甲酸" data-language-autonym="文言" data-language-local-name="Literary Chinese" class="interlanguage-link-target"><span>文言</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Aksido_Formico" title="Aksido Formico – Waray" lang="war" hreflang="war" data-title="Aksido Formico" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E7%94%B2%E9%85%B8" title="甲酸 – Wu" lang="wuu" hreflang="wuu" data-title="甲酸" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%9F%BB%E9%85%B8" title="蟻酸 – Cantonese" lang="yue" hreflang="yue" data-title="蟻酸" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%94%B2%E9%85%B8" title="甲酸 – Chinese" lang="zh" hreflang="zh" data-title="甲酸" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a 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dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">"Ant acid" redirects here. For substances that neutralize stomach acidity, see <a href="/wiki/Antacid" title="Antacid">antacid</a>.</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Simplest carboxylic acid (HCOOH)</div> <p> <style data-mw-deduplicate="TemplateStyles:r1268415487">.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%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> </p> <table class="infobox ib-chembox"> <caption>Formic acid </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Formic_acid.svg" class="mw-file-description" title="Skeletal structure of formic acid"><img alt="Skeletal structure of formic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Formic_acid.svg/110px-Formic_acid.svg.png" decoding="async" width="110" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Formic_acid.svg/165px-Formic_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Formic_acid.svg/220px-Formic_acid.svg.png 2x" data-file-width="166" data-file-height="134" /></a><figcaption>Skeletal structure of formic acid</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Formic-acid-CRC-MW-3D-balls.png" class="mw-file-description" title="3D model of formic acid"><img alt="3D model of formic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Formic-acid-CRC-MW-3D-balls.png/110px-Formic-acid-CRC-MW-3D-balls.png" decoding="async" width="110" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Formic-acid-CRC-MW-3D-balls.png/165px-Formic-acid-CRC-MW-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Formic-acid-CRC-MW-3D-balls.png/220px-Formic-acid-CRC-MW-3D-balls.png 2x" data-file-width="1100" data-file-height="929" /></a><figcaption>3D model of formic acid</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Formic_acid_85_percent.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Formic_acid_85_percent.jpg/120px-Formic_acid_85_percent.jpg" decoding="async" width="120" height="168" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Formic_acid_85_percent.jpg/180px-Formic_acid_85_percent.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Formic_acid_85_percent.jpg/240px-Formic_acid_85_percent.jpg 2x" data-file-width="500" data-file-height="700" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Formic acid<sup id="cite_ref-iupac2013_1-0" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Methanoic acid<sup id="cite_ref-iupac2013_1-1" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><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>Formylic acid</li><li>Methylic acid</li><li>Hydrogencarboxylic acid</li><li>Hydroxy(oxo)methane</li><li>Metacarbonoic acid</li><li>Oxocarbinic acid</li><li>Oxomethanol</li><li>Hydroxymethylene oxide</li></ul></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=64-18-6">64-18-6</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;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DCO">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1209246 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=30751">CHEBI:30751</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/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL116736">ChEMBL116736</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/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.278.html">278</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/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB01942">DB01942</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/100.000.527">100.000.527</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q161233#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>200-579-1</li></ul></div> </td></tr> <tr> <td><a href="/wiki/E_number" title="E number"><span title="E number (food additive code)">E number</span></a> </td> <td>E236 <a href="/wiki/E_number#E200–E299" title="E number">(preservatives)</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>1008 </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00058">C00058</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/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/284">284</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>LQ4900000</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/0YIW783RG1">0YIW783RG1</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/DTXSID2024115">DTXSID2024115</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q161233#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> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/HCOOH/c2-1-3/h1H,(H,2,3)<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: BDAGIHXWWSANSR-UHFFFAOYSA-N<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></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/HCOOH/c2-1-3/h1H,(H,2,3)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: BDAGIHXWWSANSR-UHFFFAOYAT</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=CO</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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><span title="Carbon">C</span><span title="Hydrogen">H</span><sub>2</sub><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001460250000000000♠"></span>46.025</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colorless fuming liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Pungent, penetrating </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.220<span class="nowrap"> </span>g/mL </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>8.4 °C (47.1 °F; 281.5 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>100.8 °C (213.4 °F; 373.9 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Miscible </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>Miscible with <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a>, <a href="/wiki/Acetone" title="Acetone">acetone</a>, <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</a>, <a href="/wiki/Glycerol" title="Glycerol">glycerol</a>, <a href="/wiki/Methanol" title="Methanol">methanol</a>, <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> <br /> Partially soluble in <a href="/wiki/Benzene" title="Benzene">benzene</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a>, <a href="/wiki/Xylene" title="Xylene">xylenes</a> </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>−0.54 </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>35<span class="nowrap"> </span>mmHg (20 °C)<sup id="cite_ref-PGCH_2-0" class="reference"><a href="#cite_note-PGCH-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>3.745<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">Conjugate base</a> </td> <td><a href="/wiki/Formate" title="Formate">Formate</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td><span class="nowrap"><span data-sort-value="3010801000000000000♠"></span>−19.90<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−6</sup> cm<sup>3</sup>/mol</span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (<i>n</i><sub>D</sub>)</div> </td> <td>1.3714 (20 °C) </td></tr> <tr> <td><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> </td> <td>1.57<span class="nowrap"> </span>c<a href="/wiki/Poise_(unit)" title="Poise (unit)">P</a> at 268 °C </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular shape</a></div> </td> <td><a href="https://en.wiktionary.org/wiki/planar" class="extiw" title="wikt:planar">Planar</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>1.41<span class="nowrap"> </span><a href="/wiki/Debye" title="Debye">D</a> (gas) </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_molar_entropy" title="Standard molar entropy">Std molar<br />entropy</a> <span style="font-size:112%;">(<i>S</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>131.8<span class="nowrap"> </span>J/mol K </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−425.0<span class="nowrap"> </span>kJ/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">Std enthalpy of<br />combustion</a> <span style="font-size:112%;">(Δ<sub>c</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−254.6<span class="nowrap"> </span>kJ/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System#ATCvet" title="Anatomical Therapeutic Chemical Classification System">ATCvet code</a></div> </td> <td><a href="/wiki/ATC_code_P53" class="mw-redirect" title="ATC code P53">QP53AG01</a> (<span title="www.whocc.no/atcvet"><a rel="nofollow" class="external text" href="https://www.whocc.no/atcvet/atcvet_index/?code=QP53AG01">WHO</a></span>)  </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>Corrosive; irritant;<br />sensitizer </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><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-flamme.svg" class="mw-file-description" title="GHS02: Flammable"><img alt="GHS02: Flammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/50px-GHS-pictogram-flamme.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/75px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/100px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.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>Danger</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="H314: Causes severe skin burns and eye damage">H314</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="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.">P301+P330+P331</abbr>, <abbr class="abbr" title="P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].">P303+P361+P353</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="P310: Immediately call a POISON CENTER or doctor/physician.">P310</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P363: Wash contaminated clothing before reuse.">P363</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/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_cac26dcfb9c9c85a" /></span><map name="ImageMap_cac26dcfb9c9c85a"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" title="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" title="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" class="notheme mw-no-invert">3</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>69 °C (156 °F; 342 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>601 °C (1,114 °F; 874 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>14–34%<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2015)">citation needed</span></a></i>]</sup><br /> 18–57% (90% solution)<sup id="cite_ref-PGCH_2-1" class="reference"><a href="#cite_note-PGCH-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>700<span class="nowrap"> </span>mg/kg (mouse, oral), 1100<span class="nowrap"> </span>mg/kg (rat, oral), 4000<span class="nowrap"> </span>mg/kg (dog, oral)<sup id="cite_ref-IDLH_4-0" class="reference"><a href="#cite_note-IDLH-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>50</sub> (<a href="/wiki/Lethal_dose#LC50" title="Lethal dose">median concentration</a>)</div> </td> <td>7853<span class="nowrap"> </span>ppm (rat, 15<span class="nowrap"> </span>min)<br />3246<span class="nowrap"> </span>ppm (mouse, 15<span class="nowrap"> </span>min)<sup id="cite_ref-IDLH_4-1" class="reference"><a href="#cite_note-IDLH-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 5<span class="nowrap"> </span>ppm (9<span class="nowrap"> </span>mg/m<sup>3</sup>)<sup id="cite_ref-PGCH_2-2" class="reference"><a href="#cite_note-PGCH-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>TWA 5<span class="nowrap"> </span>ppm (9<span class="nowrap"> </span>mg/m<sup>3</sup>)<sup id="cite_ref-PGCH_2-3" class="reference"><a href="#cite_note-PGCH-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>30<span class="nowrap"> </span>ppm<sup id="cite_ref-PGCH_2-4" class="reference"><a href="#cite_note-PGCH-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="http://www.jtbaker.com/msds/englishhtml/f5956.htm">MSDS from JT Baker</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a></div> </td> <td><a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a><br /><a href="/wiki/Propionic_acid" title="Propionic acid">Propionic acid</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a><br /><a href="/wiki/Methanol" title="Methanol">Methanol</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Supplementary data page </th></tr> <tr> <td colspan="2" style="text-align:center"><a href="/wiki/Formic_acid_(data_page)" title="Formic acid (data page)">Formic acid (data page)</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; 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 style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=443825627&page2=Formic+acid">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <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><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></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>Formic acid</b> (from <a href="/wiki/Latin_language" class="mw-redirect" title="Latin language">Latin</a> <i> formica</i> '<a href="/wiki/Ant" title="Ant">ant</a>'), <a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">systematically named</a> <b>methanoic acid</b>, is the simplest <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>, and has the <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> HCOOH and structure <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">H−C(=O)−O−H</span>. It is an important intermediate in <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">chemical synthesis</a> and occurs naturally, most notably in some ants. <a href="/wiki/Ester" title="Ester">Esters</a>, <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a> and the <a href="/wiki/Anion" class="mw-redirect" title="Anion">anion</a> derived from formic acid are called <a href="/wiki/Formate" title="Formate">formates</a>. Industrially, formic acid is produced from <a href="/wiki/Methanol" title="Methanol">methanol</a>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence">Natural occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=1" title="Edit section: Natural occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Insect_defenses" class="mw-redirect" title="Insect defenses">Insect defenses</a></div> <p>Formic acid is found naturally in insects, weeds, fruits and vegetables, and forest emissions. It appears in most <a href="/wiki/Ants" class="mw-redirect" title="Ants">ants</a> and in <a href="/wiki/Stingless_bee" title="Stingless bee">stingless bees</a> of the genus <i><a href="/wiki/Oxytrigona" title="Oxytrigona">Oxytrigona</a></i>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><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> <a href="/wiki/Formica_rufa_species_group" title="Formica rufa species group">Wood ants</a> from the genus <i><a href="/wiki/Formica" title="Formica">Formica</a></i> can spray formic acid on their prey or to defend the nest. The <a href="/wiki/Cerura_vinula" title="Cerura vinula">puss moth caterpillar</a> (<i>Cerura vinula</i>) will spray it as well when threatened by predators. It is also found in the <a href="/wiki/Trichome" title="Trichome">trichomes</a> of <a href="/wiki/Stinging_nettle" class="mw-redirect" title="Stinging nettle">stinging nettle</a> (<i>Urtica dioica</i>). Apart from that, this acid is incorporated in many fruits such as pineapple (0.21 mg per 100 g), apple (2 mg per 100 g) and kiwi (1 mg per 100 g), as well as in many vegetables, namely onion (45 mg per 100 g), eggplant (1.34 mg per 100 g) and, in extremely low concentrations, cucumber (0.11 mg per 100 g).<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> Formic acid is a naturally occurring component of the <a href="/wiki/Atmosphere_of_Earth" title="Atmosphere of Earth">atmosphere</a> primarily due to forest emissions.<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="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=2" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As early as the 15th century, some <a href="/wiki/Alchemy" title="Alchemy">alchemists</a> and <a href="/wiki/Natural_history" title="Natural history">naturalists</a> were aware that ant hills give off an acidic vapor. The first person to describe the isolation of this substance (by the distillation of large numbers of ants) was the English naturalist <a href="/wiki/John_Ray" title="John Ray">John Ray</a>, in 1671.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><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> Ants secrete the formic acid for attack and defense purposes. Formic acid was first synthesized from <a href="/wiki/Hydrocyanic_acid" class="mw-redirect" title="Hydrocyanic acid">hydrocyanic acid</a> by the French chemist <a href="/wiki/Joseph_Gay-Lussac" class="mw-redirect" title="Joseph Gay-Lussac">Joseph Gay-Lussac</a>. In 1855, another French chemist, <a href="/wiki/Marcellin_Berthelot" title="Marcellin Berthelot">Marcellin Berthelot</a>, developed a synthesis from <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> similar to the process used today.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2024)">citation needed</span></a></i>]</sup> </p><p>Formic acid was long considered a <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> of only minor interest in the chemical industry. In the late 1960s, significant quantities became available as a byproduct of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> production. It now finds increasing use as a preservative and antibacterial in <a href="/wiki/Livestock" title="Livestock">livestock</a> feed.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2024)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=3" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Formic_Acid_Hydrogenbridge_V.1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Formic_Acid_Hydrogenbridge_V.1.svg/220px-Formic_Acid_Hydrogenbridge_V.1.svg.png" decoding="async" width="220" height="91" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Formic_Acid_Hydrogenbridge_V.1.svg/330px-Formic_Acid_Hydrogenbridge_V.1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Formic_Acid_Hydrogenbridge_V.1.svg/440px-Formic_Acid_Hydrogenbridge_V.1.svg.png 2x" data-file-width="363" data-file-height="150" /></a><figcaption>Cyclic dimer of formic acid; dashed <span style="color:green;"><b>green</b></span> lines represent hydrogen bonds</figcaption></figure> <p>Formic acid is a colorless liquid having a pungent, penetrating odor<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> at room temperature, comparable to the related <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>. Formic acid is about ten times stronger than <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2024)">citation needed</span></a></i>]</sup> </p><p>It is <a href="/wiki/Miscibility" title="Miscibility">miscible</a> with water and most polar <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic</a> <a href="/wiki/Solvent" title="Solvent">solvents</a>, and is somewhat soluble in <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbons</a>. In hydrocarbons and in the vapor phase, it consists of <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen-bonded</a> <a href="/wiki/Dimer_(chemistry)" class="mw-redirect" title="Dimer (chemistry)">dimers</a> rather than individual molecules.<sup id="cite_ref-Ullmann_2009_13-0" class="reference"><a href="#cite_note-Ullmann_2009-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Balabin_2009_14-0" class="reference"><a href="#cite_note-Balabin_2009-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Owing to its tendency to hydrogen-bond, gaseous formic acid does not obey the <a href="/wiki/Ideal_gas_law" title="Ideal gas law">ideal gas law</a>.<sup id="cite_ref-Balabin_2009_14-1" class="reference"><a href="#cite_note-Balabin_2009-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Solid formic acid, which can exist in either of two <a href="/wiki/Polymorphism_(materials_science)" class="mw-redirect" title="Polymorphism (materials science)">polymorphs</a>, consists of an effectively endless network of hydrogen-bonded formic acid molecules. Formic acid forms a high-boiling <a href="/wiki/Azeotrope" title="Azeotrope">azeotrope</a> with water (107.3 °C; 77.5% formic acid). Liquid formic acid tends to <a href="/wiki/Supercooling" title="Supercooling">supercool</a>. </p> <div style="clear:left;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Chemical_reactions">Chemical reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=4" title="Edit section: Chemical reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Decomposition">Decomposition</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=5" title="Edit section: Decomposition"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formic acid readily decomposes by dehydration in the presence of concentrated <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> to form <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> and water: </p> <dl><dd>HCO<sub>2</sub>H → H<sub>2</sub>O + CO</dd></dl> <p>Treatment of formic acid with sulfuric acid is a convenient laboratory source of CO.<sup id="cite_ref-koch_15-0" class="reference"><a href="#cite_note-koch-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> <sup id="cite_ref-coleman_16-0" class="reference"><a href="#cite_note-coleman-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>In the presence of <a href="/wiki/Platinum" title="Platinum">platinum</a>, it decomposes with a release of <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> and <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>. </p> <dl><dd>HCO<sub>2</sub>H → H<sub>2</sub> + CO<sub>2</sub></dd></dl> <p>Soluble <a href="/wiki/Ruthenium" title="Ruthenium">ruthenium</a> catalysts are also effective for producing carbon monoxide-free hydrogen.<sup id="cite_ref-Fellay2008_17-0" class="reference"><a href="#cite_note-Fellay2008-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Reactant">Reactant</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=6" title="Edit section: Reactant"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formic acid shares most of the chemical properties of other <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a>. Because of its high acidity, solutions in alcohols form esters spontaneously; in <a href="/wiki/Fischer_esterification" class="mw-redirect" title="Fischer esterification">Fischer esterifications</a> of formic acid, it self-catalyzes the reaction and no additional acid catalyst is needed.<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> Formic acid shares some of the <a href="/wiki/Redox" title="Redox">reducing</a> properties of <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a>, reducing solutions of metal oxides to their respective metal.<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>Formic acid is a source for a <a href="/wiki/Formyl" class="mw-redirect" title="Formyl">formyl</a> group for example in the <a href="/wiki/Formylation" title="Formylation">formylation</a> of <a href="/wiki/N-Methylaniline" title="N-Methylaniline"><i>N</i>-methylaniline</a> to <i>N</i>-methylformanilide in <a href="/wiki/Toluene" title="Toluene">toluene</a>.<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> </p><p>In <a href="/wiki/Organic_synthesis" title="Organic synthesis">synthetic organic chemistry</a>, formic acid is often used as a source of <a href="/wiki/Hydride" title="Hydride">hydride</a> ion, as in the <a href="/wiki/Eschweiler%E2%80%93Clarke_reaction" title="Eschweiler–Clarke reaction">Eschweiler–Clarke reaction</a>: </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Eschweiler-Clarke_Reaction.svg" class="mw-file-description" title="The Eschweiler–Clark reaction"><img alt="The Eschweiler–Clark reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Eschweiler-Clarke_Reaction.svg/300px-Eschweiler-Clarke_Reaction.svg.png" decoding="async" width="300" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Eschweiler-Clarke_Reaction.svg/450px-Eschweiler-Clarke_Reaction.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Eschweiler-Clarke_Reaction.svg/600px-Eschweiler-Clarke_Reaction.svg.png 2x" data-file-width="512" data-file-height="169" /></a><figcaption>The Eschweiler–Clark reaction</figcaption></figure> <p>It is used as a source of hydrogen in <a href="/wiki/Transfer_hydrogenation" title="Transfer hydrogenation">transfer hydrogenation</a>, as in the <a href="/wiki/Leuckart_reaction" title="Leuckart reaction">Leuckart reaction</a> to make <a href="/wiki/Amine" title="Amine">amines</a>, and (in aqueous solution or in its <a href="/wiki/Azeotrope" title="Azeotrope">azeotrope</a> with <a href="/wiki/Triethylamine" title="Triethylamine">triethylamine</a>) for hydrogenation of <a href="/wiki/Ketone" title="Ketone">ketones</a>.<sup id="cite_ref-Zhou2012_21-0" class="reference"><a href="#cite_note-Zhou2012-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Addition_to_alkenes">Addition to alkenes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=7" title="Edit section: Addition to alkenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formic acid is unique among the carboxylic acids in its ability to participate in addition reactions with <a href="/wiki/Alkene" title="Alkene">alkenes</a>. Formic acids and alkenes readily react to form formate <a href="/wiki/Ester" title="Ester">esters</a>. In the presence of certain acids, including <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric</a> and <a href="/wiki/Hydrofluoric_acid" title="Hydrofluoric acid">hydrofluoric acids</a>, however, a variant of the <a href="/wiki/Koch_reaction" title="Koch reaction">Koch reaction</a> occurs instead, and formic acid adds to the alkene to produce a larger carboxylic acid.<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-heading3"><h3 id="Formic_acid_anhydride">Formic acid anhydride</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=8" title="Edit section: Formic acid anhydride"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An unstable <a href="/wiki/Formic_anhydride" title="Formic anhydride">formic anhydride</a>, H(C=O)−O−(C=O)H, can be obtained by dehydration of formic acid with <a href="/wiki/N,N%27-Dicyclohexylcarbodiimide" title="N,N'-Dicyclohexylcarbodiimide"><i>N</i>,<i>N<span class="nowrap" style="padding-left:0.05em;">′</span></i>-dicyclohexylcarbodiimide</a> in ether at low temperature.<sup id="cite_ref-gwu_23-0" class="reference"><a href="#cite_note-gwu-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=9" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 2009, the worldwide capacity for producing formic acid was 720 thousand tonnes (1.6 billion pounds) per year, roughly equally divided between Europe (350 thousand tonnes or 770 million pounds, mainly in Germany) and Asia (370 thousand tonnes or 820 million pounds, mainly in China) while production was below 1 thousand tonnes or 2.2 million pounds per year in all other continents.<sup id="cite_ref-CEH_24-0" class="reference"><a href="#cite_note-CEH-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> It is commercially available in solutions of various concentrations between 85 and 99 w/w %.<sup id="cite_ref-Ullmann_2009_13-1" class="reference"><a href="#cite_note-Ullmann_2009-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> As of 2009<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Formic_acid&action=edit">[update]</a></sup>, the largest producers are <a href="/wiki/BASF" title="BASF">BASF</a>, <a href="/wiki/Eastman_Chemical_Company" title="Eastman Chemical Company">Eastman Chemical Company</a>, <a href="/w/index.php?title=LC_Industrial&action=edit&redlink=1" class="new" title="LC Industrial (page does not exist)">LC Industrial</a>, and <a href="/wiki/Feicheng_Acid_Chemicals" title="Feicheng Acid Chemicals">Feicheng Acid Chemicals</a>, with the largest production facilities in <a href="/wiki/Ludwigshafen" title="Ludwigshafen">Ludwigshafen</a> (200 thousand tonnes or 440 million pounds per year, BASF, Germany), <a href="/wiki/Oulu" title="Oulu">Oulu</a> (105 thousand tonnes or 230 million pounds, Eastman, Finland), <a href="/wiki/Nakhon_Pathom" title="Nakhon Pathom">Nakhon Pathom</a> (n/a, LC Industrial), and <a href="/wiki/Feicheng" title="Feicheng">Feicheng</a> (100 thousand tonnes or 220 million pounds, Feicheng, China). 2010 prices ranged from around €650/tonne (equivalent to around $800/tonne) in Western Europe to $1250/tonne in the United States.<sup id="cite_ref-CEH_24-1" class="reference"><a href="#cite_note-CEH-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="From_methyl_formate_and_formamide">From methyl formate and formamide</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=10" title="Edit section: From methyl formate and formamide"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>When <a href="/wiki/Methanol" title="Methanol">methanol</a> and <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> are combined in the presence of a strong <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a>, the result is <a href="/wiki/Methyl_formate" title="Methyl formate">methyl formate</a>, according to the <a href="/wiki/Chemical_equation" title="Chemical equation">chemical equation</a>:<sup id="cite_ref-Ullmann_2009_13-2" class="reference"><a href="#cite_note-Ullmann_2009-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>CH<sub>3</sub>OH + CO → HCO<sub>2</sub>CH<sub>3</sub></dd></dl> <p>In industry, this reaction is performed in the liquid phase at elevated pressure. Typical reaction conditions are 80 °C and 40 atm. The most widely used base is <a href="/wiki/Sodium_methoxide" title="Sodium methoxide">sodium methoxide</a>. <a href="/wiki/Hydrolysis" title="Hydrolysis">Hydrolysis</a> of the methyl formate produces formic acid: </p> <dl><dd>HCO<sub>2</sub>CH<sub>3</sub> + H<sub>2</sub>O → HCOOH + CH<sub>3</sub>OH</dd></dl> <p>Efficient hydrolysis of methyl formate requires a large excess of water. Some routes proceed indirectly by first treating the methyl formate with <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> to give <a href="/wiki/Formamide" title="Formamide">formamide</a>, which is then hydrolyzed with <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a>: </p> <dl><dd>HCO<sub>2</sub>CH<sub>3</sub> + NH<sub>3</sub> → HC(O)NH<sub>2</sub> + CH<sub>3</sub>OH</dd> <dd>2 HC(O)NH<sub>2</sub> + 2H<sub>2</sub>O + H<sub>2</sub>SO<sub>4</sub> → 2HCO<sub>2</sub>H + (NH<sub>4</sub>)<sub>2</sub>SO<sub>4</sub></dd></dl> <p>A disadvantage of this approach is the need to dispose of the <a href="/wiki/Ammonium_sulfate" title="Ammonium sulfate">ammonium sulfate</a> byproduct. This problem has led some manufacturers to develop energy-efficient methods of separating formic acid from the excess water used in direct hydrolysis. In one of these processes, used by <a href="/wiki/BASF" title="BASF">BASF</a>, the formic acid is removed from the water by <a href="/wiki/Liquid-liquid_extraction" class="mw-redirect" title="Liquid-liquid extraction">liquid-liquid extraction</a> with an organic base.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2017)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Niche_and_obsolete_chemical_routes">Niche and obsolete chemical routes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=11" title="Edit section: Niche and obsolete chemical routes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="By-product_of_acetic_acid_production">By-product of acetic acid production</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=12" title="Edit section: By-product of acetic acid production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A significant amount of formic acid is produced as a byproduct in the manufacture of other chemicals. At one time, <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> was produced on a large scale by oxidation of <a href="/wiki/Alkane" title="Alkane">alkanes</a>, by a process that cogenerates significant formic acid.<sup id="cite_ref-Ullmann_2009_13-3" class="reference"><a href="#cite_note-Ullmann_2009-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> This oxidative route to acetic acid has declined in importance so that the aforementioned dedicated routes to formic acid have become more important.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2024)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading4"><h4 id="Hydrogenation_of_carbon_dioxide">Hydrogenation of carbon dioxide</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=13" title="Edit section: Hydrogenation of carbon dioxide"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The catalytic <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> of <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a> to formic acid has long been studied. This reaction can be conducted homogeneously.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p><br /> </p> <div class="mw-heading mw-heading4"><h4 id="Oxidation_of_biomass">Oxidation of biomass</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=14" title="Edit section: Oxidation of biomass"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formic acid can also be obtained by aqueous catalytic partial oxidation of wet biomass by the <a href="/wiki/OxFA_process" title="OxFA process">OxFA process</a>.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> A <a href="/wiki/Keggin_structure" title="Keggin structure">Keggin-type</a> polyoxometalate (H<sub>5</sub>PV<sub>2</sub>Mo<sub>10</sub>O<sub>40</sub>) is used as the homogeneous catalyst to convert sugars, wood, waste paper, or cyanobacteria to formic acid and CO<sub>2</sub> as the sole byproduct. Yields of up to 53% formic acid can be achieved.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2018)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading4"><h4 id="Laboratory_methods">Laboratory methods</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=15" title="Edit section: Laboratory methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the laboratory, formic acid can be obtained by heating <a href="/wiki/Oxalic_acid" title="Oxalic acid">oxalic acid</a> in <a href="/wiki/Glycerol" title="Glycerol">glycerol</a> followed by steam distillation.<sup id="cite_ref-chattaway_30-0" class="reference"><a href="#cite_note-chattaway-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> Glycerol acts as a catalyst, as the reaction proceeds through a glyceryl oxalate intermediate. If the reaction mixture is heated to higher temperatures, <a href="/wiki/Allyl_alcohol" title="Allyl alcohol">allyl alcohol</a> results. The net reaction is thus: </p> <dl><dd>C<sub>2</sub>O<sub>4</sub>H<sub>2</sub> → HCO<sub>2</sub>H + CO<sub>2</sub></dd></dl> <p>Another illustrative method involves the reaction between <a href="/w/index.php?title=Lead_formate&action=edit&redlink=1" class="new" title="Lead formate (page does not exist)">lead formate</a> and <a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">hydrogen sulfide</a>, driven by the formation of <a href="/wiki/Lead_sulfide" title="Lead sulfide">lead sulfide</a>.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>Pb(HCOO)<sub>2</sub> + H<sub>2</sub>S → 2HCOOH + PbS</dd></dl> <div class="mw-heading mw-heading4"><h4 id="Electrochemical_production">Electrochemical production</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=16" title="Edit section: Electrochemical production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formate is formed by the <a href="/wiki/Electrochemical_reduction" class="mw-redirect" title="Electrochemical reduction">electrochemical reduction</a> of CO<sub>2</sub> (in the form of <a href="/wiki/Bicarbonate" title="Bicarbonate">bicarbonate</a>) at a <a href="/wiki/Lead" title="Lead">lead</a> <a href="/wiki/Cathode" title="Cathode">cathode</a> at pH 8.6:<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="chemf nowrap">HCO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span> + <span class="chemf nowrap">H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>O</span> + 2e<sup>−</sup> → <span class="chemf nowrap">HCO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> + 2<span class="chemf nowrap">OH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span></span></dd></dl> <p>or </p> <dl><dd><span class="chemf nowrap">CO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> + <span class="chemf nowrap">H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>O</span> + 2e<sup>−</sup> → <span class="chemf nowrap">HCO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> + <span class="chemf nowrap">OH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span></span></dd></dl> <p>If the feed is <span class="chemf nowrap">CO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> and oxygen is evolved at the anode, the total reaction is: </p> <dl><dd>CO<sub style="font-size: 80%;vertical-align: -0.35em">2</sub> + <span class="chemf nowrap">OH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span></span> → <span class="chemf nowrap">HCO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> + 1/2 <a href="/wiki/Oxygen" title="Oxygen">O<sub>2</sub></a></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=17" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formic acid is named after ants which have high concentrations of the compound in their venom, derived from <a href="/wiki/Serine" title="Serine">serine</a> through a <a href="/wiki/5,10-methenyltetrahydrofolate" class="mw-redirect" title="5,10-methenyltetrahydrofolate">5,10-methenyltetrahydrofolate</a> intermediate.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> The conjugate base of formic acid, formate, also occurs widely in nature. An <a href="/wiki/Assay" title="Assay">assay</a> for formic acid in body fluids, designed for determination of formate after methanol poisoning, is based on the reaction of formate with bacterial <a href="/wiki/Formate_dehydrogenase" title="Formate dehydrogenase">formate dehydrogenase</a>.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=18" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Agriculture">Agriculture</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=19" title="Edit section: Agriculture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A major use of formic acid is as a <a href="/wiki/Preservative" title="Preservative">preservative</a> and <a href="/wiki/Bacteria" title="Bacteria">antibacterial</a> agent in livestock feed. It arrests certain decay processes and causes the feed to retain its nutritive value longer, </p><p>In Europe, it is applied on <a href="/wiki/Silage" title="Silage">silage</a>, including fresh hay, to promote the fermentation of <a href="/wiki/Lactic_acid" title="Lactic acid">lactic acid</a> and to suppress the formation of <a href="/wiki/Butyric_acid" title="Butyric acid">butyric acid</a>; it also allows fermentation to occur quickly, and at a lower temperature, reducing the loss of nutritional value.<sup id="cite_ref-Ullmann_2009_13-4" class="reference"><a href="#cite_note-Ullmann_2009-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> It is widely used to preserve winter feed for <a href="/wiki/Cattle" title="Cattle">cattle</a>,<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> and is sometimes added to <a href="/wiki/Poultry" title="Poultry">poultry</a> feed to kill <i><a href="/wiki/Escherichia_coli" title="Escherichia coli">E. coli</a></i> bacteria.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> Use as a preservative for silage and other animal feed constituted 30% of the global consumption in 2009.<sup id="cite_ref-CEH_24-2" class="reference"><a href="#cite_note-CEH-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Beekeeper" title="Beekeeper">Beekeepers</a> use formic acid as a <a href="/wiki/Miticide" class="mw-redirect" title="Miticide">miticide</a> against the tracheal mite (<i><a href="/wiki/Acarapis_woodi" title="Acarapis woodi">Acarapis woodi</a></i>) and the <a href="/wiki/Varroa_destructor" title="Varroa destructor"><i>Varroa destructor</i> mite</a> and <a href="/wiki/Varroa_jacobsoni" title="Varroa jacobsoni"><i>Varroa jacobsoni</i> mite</a>.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Energy">Energy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=20" title="Edit section: Energy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formic acid can be used directly in <a href="/wiki/Formic_acid_fuel_cell" title="Formic acid fuel cell">formic acid fuel cells</a> or indirectly in hydrogen <a href="/wiki/Fuel_cell" title="Fuel cell">fuel cells</a>.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p><p>Electrolytic conversion of electrical energy to chemical fuel has been proposed as a large-scale source of formate by various groups.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> The formate could be used as feed to modified <i><a href="/wiki/Escherichia_coli" title="Escherichia coli">E. coli</a></i> bacteria for producing <a href="/wiki/Biomass" title="Biomass">biomass</a>.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Natural <a href="/wiki/Methylotroph" title="Methylotroph">methylotroph</a> microbes can feed on formic acid or formate. </p><p>Formic acid has been considered as a means of <a href="/wiki/Hydrogen_storage" title="Hydrogen storage">hydrogen storage</a>.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> The co-product of this decomposition, carbon dioxide, can be rehydrogenated back to formic acid in a second step. Formic acid contains 53 g/L hydrogen at room temperature and atmospheric pressure, which is three and a half times as much as compressed hydrogen gas can attain at 350 bar pressure (14.7 g/L). Pure formic acid is a liquid with a <a href="/wiki/Flash_point" title="Flash point">flash point</a> of 69 °C, much higher than that of gasoline (−40 °C) or ethanol (13 °C).<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2017)">citation needed</span></a></i>]</sup> </p><p>It is possible to use formic acid as an intermediary to produce <a href="/wiki/Isobutanol" title="Isobutanol">isobutanol</a> from CO<sub style="font-size: 80%;vertical-align: -0.35em">2</sub> using microbes.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Soldering">Soldering</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=21" title="Edit section: Soldering"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formic acid has a potential application in <a href="/wiki/Soldering" title="Soldering">soldering</a>. Due to its capacity to reduce oxide layers, formic acid gas can be blasted at an oxide surface to increase solder <a href="/wiki/Soldering#Flux" title="Soldering">wettability</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2024)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Chromatography">Chromatography</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=22" title="Edit section: Chromatography"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formic acid is used as a volatile pH modifier in <a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">HPLC</a> and <a href="/wiki/Capillary_electrophoresis" title="Capillary electrophoresis">capillary electrophoresis</a>. Formic acid is often used as a component of mobile phase in <a href="/wiki/Reversed-phase_chromatography" title="Reversed-phase chromatography">reversed-phase</a> <a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">high-performance liquid chromatography</a> (RP-HPLC) analysis and separation techniques for the separation of hydrophobic macromolecules, such as peptides, proteins and more complex structures including intact viruses. Especially when paired with <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometry</a> detection, formic acid offers several advantages over the more traditionally used <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">phosphoric acid</a>.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other_uses">Other uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=23" title="Edit section: Other uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formic acid is also significantly used in the production of leather, including <a href="/wiki/Tanning_(leather)" title="Tanning (leather)">tanning</a> (23% of the global consumption in 2009<sup id="cite_ref-CEH_24-3" class="reference"><a href="#cite_note-CEH-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup>), and in dyeing and finishing textiles (9% of the global consumption in 2009<sup id="cite_ref-CEH_24-4" class="reference"><a href="#cite_note-CEH-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup>) because of its acidic nature. Use as a coagulant in the <a href="/wiki/Production_of_rubber" class="mw-redirect" title="Production of rubber">production of rubber</a><sup id="cite_ref-Ullmann_2009_13-5" class="reference"><a href="#cite_note-Ullmann_2009-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> consumed 6% of the global production in 2009.<sup id="cite_ref-CEH_24-5" class="reference"><a href="#cite_note-CEH-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>Formic acid is also used in place of mineral acids for various cleaning products,<sup id="cite_ref-Ullmann_2009_13-6" class="reference"><a href="#cite_note-Ullmann_2009-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> such as <a href="/wiki/Limescale" title="Limescale">limescale</a> remover and <a href="/wiki/Household_cleaner" class="mw-redirect" title="Household cleaner">toilet bowl cleaner</a>. Some formate <a href="/wiki/Esters" class="mw-redirect" title="Esters">esters</a> are artificial flavorings and perfumes. </p><p>Formic acid application has been reported to be an effective treatment for <a href="/wiki/Wart" title="Wart">warts</a>.<sup id="cite_ref-pmid11589750_49-0" class="reference"><a href="#cite_note-pmid11589750-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formic_acid&action=edit&section=24" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formic acid has low toxicity (hence its use as a food additive), with an <a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD<sub style="font-size:-1">50</sub></a> of 1.8<span class="nowrap"> </span>g/kg (tested orally on mice). The concentrated acid is corrosive to the skin.<sup id="cite_ref-Ullmann_2009_13-7" class="reference"><a href="#cite_note-Ullmann_2009-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>Formic acid is readily metabolized and eliminated by the body. Nonetheless, it has specific <a href="/wiki/Toxic" class="mw-redirect" title="Toxic">toxic</a> effects; the formic acid and <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> produced as metabolites of <a href="/wiki/Methanol" title="Methanol">methanol</a> are responsible for the <a href="/wiki/Optic_nerve" title="Optic nerve">optic nerve</a> damage, causing blindness, seen in <a href="/wiki/Methanol_poisoning" class="mw-redirect" title="Methanol poisoning">methanol poisoning</a>.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> Some chronic effects of formic acid exposure have been documented. Some experiments on bacterial species have demonstrated it to be a <a href="/wiki/Mutagen" title="Mutagen">mutagen</a>.<sup id="cite_ref-osha.gov_51-0" class="reference"><a href="#cite_note-osha.gov-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> Chronic exposure in humans may cause kidney damage.<sup id="cite_ref-osha.gov_51-1" class="reference"><a href="#cite_note-osha.gov-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> Another possible effect of chronic exposure is development of a skin <a href="/wiki/Allergy" title="Allergy">allergy</a> that manifests upon re-exposure to the chemical. </p><p>Concentrated formic acid slowly decomposes to carbon monoxide and water, leading to pressure buildup in the containing vessel. For this reason, 98% formic acid is shipped in plastic bottles with self-venting caps.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2024)">citation needed</span></a></i>]</sup> </p><p>The hazards of solutions of formic acid depend on the concentration. The following table lists the <a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals">Globally Harmonized System of Classification and Labelling of Chemicals</a> for formic acid solutions:<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (October 2021)">citation needed</span></a></i>]</sup> </p> <table class="wikitable"> <tbody><tr> <th><a href="/wiki/Concentration" title="Concentration">Concentration</a> (<a href="/wiki/Weight_percent" class="mw-redirect" title="Weight percent">weight percent</a>) </th> <th>Pictogram </th> <th><a href="/wiki/List_of_H-phrases" class="mw-redirect" title="List of H-phrases">H-Phrases</a> </th></tr> <tr> <td>2–10% </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> </td> <td><abbr class="abbr" title="H315: Causes skin irritation">H315</abbr> </td></tr> <tr> <td>10–90% </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td> <td><abbr class="abbr" title="H313: May be harmful in contact with skin">H313</abbr> </td></tr> <tr> <td>>90% </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td> <td><abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr> </td></tr></tbody></table> <p>Formic acid in 85% concentration is flammable, and diluted formic acid is on the U.S. Food and Drug Administration list of food additives.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> The principal danger from formic acid is from skin or eye contact with the concentrated liquid or vapors. The U.S. <a href="/wiki/Occupational_Safety_and_Health_Administration" title="Occupational Safety and Health Administration">OSHA</a> Permissible Exposure Level (<a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a>) of formic acid vapor in the work environment is 5 <a href="/wiki/Parts_per_million" class="mw-redirect" title="Parts per million">parts per million</a> (ppm) of air.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<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=Formic_acid&action=edit&section=25" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Orthoformic_acid" title="Orthoformic acid">Orthoformic acid</a></li> <li><a href="/wiki/Alternative_fuel_vehicle#Formic_acid" title="Alternative fuel vehicle">Formic acid vehicle</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=Formic_acid&action=edit&section=26" 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-iupac2013-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-iupac2013_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-iupac2013_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 .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFFavrePowell2014" class="citation book cs1">Favre, Henri A.; Powell, Warren H. 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Retrieved <span class="nowrap">28 May</span> 2011</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Occupational+Safety+and+Health+Guideline+for+Formic+Acid&rft.pub=OSHA&rft_id=http%3A%2F%2Fwww.osha.gov%2FSLTC%2Fhealthguidelines%2Fformicacid%2Frecognition.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFormic+acid" class="Z3988"></span></span> </li> <li id="cite_note-52"><span class="mw-cite-backlink"><b><a href="#cite_ref-52">^</a></b></span> <span class="reference-text"><span><a href="/wiki/Title_21_of_the_Code_of_Federal_Regulations" title="Title 21 of the Code of Federal Regulations">21 CFR</a> <a rel="nofollow" class="external text" href="https://www.ecfr.gov/current/title-21/section-186.1316">186.1316</a></span>, <span><a href="/wiki/Title_21_of_the_Code_of_Federal_Regulations" title="Title 21 of the Code of Federal Regulations">21 CFR</a> <a rel="nofollow" class="external text" href="https://www.ecfr.gov/current/title-21/section-172.515">172.515</a></span></span> </li> <li id="cite_note-53"><span class="mw-cite-backlink"><b><a href="#cite_ref-53">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0296.html">"CDC - NIOSH Pocket Guide to Chemical Hazards - Formic acid"</a>. <i>www.cdc.gov</i><span class="reference-accessdate">. Retrieved <span class="nowrap">1 November</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.cdc.gov&rft.atitle=CDC+-+NIOSH+Pocket+Guide+to+Chemical+Hazards+-+Formic+acid&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0296.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFormic+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=Formic_acid&action=edit&section=27" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid 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oxide</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="9" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/Nitrous_oxide" title="Nitrous oxide"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/60px-Nitrous-oxide-3D-balls.png" decoding="async" width="60" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/90px-Nitrous-oxide-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/120px-Nitrous-oxide-3D-balls.png 2x" data-file-width="1100" data-file-height="441" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Ethanol" title="Ethanol"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/60px-Ethanol-3D-balls.png" decoding="async" width="60" height="41" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/90px-Ethanol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/120px-Ethanol-3D-balls.png 2x" data-file-width="1100" data-file-height="754" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/60px-Buckminsterfullerene-perspective-3D-balls.png" decoding="async" width="60" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/90px-Buckminsterfullerene-perspective-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/120px-Buckminsterfullerene-perspective-3D-balls.png 2x" data-file-width="1056" data-file-height="1100" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triatomic_molecule" title="Triatomic molecule">Triatomic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium(I)_hydroxide" class="mw-redirect" title="Aluminium(I) hydroxide">Aluminium(I) hydroxide</a></li> <li><a href="/w/index.php?title=Aluminium_isocyanide&action=edit&redlink=1" class="new" title="Aluminium isocyanide (page does not exist)">Aluminium isocyanide</a></li> <li><a href="/wiki/Amino_radical" title="Amino radical">Amino radical</a></li> <li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">Carbon dioxide</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide</a></li> <li><a href="/w/index.php?title=CCP_radical&action=edit&redlink=1" class="new" title="CCP radical (page does not exist)">CCP radical</a></li> <li><a href="/wiki/Halonium_ion" title="Halonium ion">Chloronium</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">Diazenylium</a></li> <li><a href="/wiki/Dicarbon_monoxide" title="Dicarbon monoxide">Dicarbon monoxide</a></li> <li><a href="/w/index.php?title=Disilicon_carbide&action=edit&redlink=1" class="new" title="Disilicon carbide (page does not exist)">Disilicon carbide</a></li> <li><a href="/wiki/Ethynyl_radical" title="Ethynyl radical">Ethynyl radical</a></li> <li><a href="/w/index.php?title=Formyl_radical&action=edit&redlink=1" class="new" title="Formyl radical (page does not exist)">Formyl radical</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a> (HCN)</li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a> (HNC)</li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide</a></li> <li><a href="/wiki/Hydroperoxyl" title="Hydroperoxyl">Hydroperoxyl</a></li> <li><a href="/wiki/Iron(II)_cyanide" title="Iron(II) cyanide">Iron cyanide</a></li> <li><a href="/w/index.php?title=Isoformyl&action=edit&redlink=1" class="new" title="Isoformyl (page does not exist)">Isoformyl</a></li> <li><a href="/wiki/Magnesium_cyanide" title="Magnesium cyanide">Magnesium cyanide</a></li> <li><a href="/w/index.php?title=Magnesium_isocyanide&action=edit&redlink=1" class="new" title="Magnesium isocyanide (page does not exist)">Magnesium isocyanide</a></li> <li><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">Methylene</a></li> <li><a href="/wiki/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>H<sup>+</sup></a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">Nitroxyl</a></li> <li><a href="/wiki/Ozone" title="Ozone">Ozone</a></li> <li><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</a></li> <li><a href="/wiki/Sodium_cyanide" title="Sodium cyanide">Sodium cyanide</a></li> <li><a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">Sodium hydroxide</a></li> <li><a href="/w/index.php?title=Silicon_carbonitride&action=edit&redlink=1" class="new" title="Silicon carbonitride (page does not exist)">Silicon carbonitride</a></li> <li><a href="/w/index.php?title=C-Silicon_dicarbide&action=edit&redlink=1" class="new" title="C-Silicon dicarbide (page does not exist)">c-Silicon dicarbide</a></li> <li><a href="/w/index.php?title=SiNC&action=edit&redlink=1" class="new" title="SiNC (page does not exist)">SiNC</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a></li> <li><a href="/w/index.php?title=Thioformyl&action=edit&redlink=1" class="new" title="Thioformyl (page does not exist)">Thioformyl</a></li> <li><a href="/wiki/Thioxoethenylidene" title="Thioxoethenylidene">Thioxoethenylidene</a></li> <li><a href="/wiki/Titanium_dioxide" title="Titanium dioxide">Titanium dioxide</a></li> <li><a href="/wiki/Tricarbon" title="Tricarbon">Tricarbon</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li> <li><a href="/wiki/Water" title="Water">Water</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Four<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Acetylene</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Cyanoethynyl</a></li> <li><a href="/wiki/Interstellar_formaldehyde" title="Interstellar formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Fulminic_acid" title="Fulminic acid">Fulminic acid</a></li> <li><a href="/w/index.php?title=HCCN&action=edit&redlink=1" class="new" title="HCCN (page does not exist)">HCCN</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/w/index.php?title=Hydromagnesium_isocyanide&action=edit&redlink=1" class="new" title="Hydromagnesium isocyanide (page does not exist)">Hydromagnesium isocyanide</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Isothiocyanic acid</a></li> <li><a href="/w/index.php?title=Ketenyl&action=edit&redlink=1" class="new" title="Ketenyl (page does not exist)">Ketenyl</a></li> <li><a href="/wiki/Methyl_cation" class="mw-redirect" title="Methyl cation">Methyl cation</a></li> <li><a href="/wiki/Methyl_radical" title="Methyl radical">Methyl radical</a></li> <li><a href="/w/index.php?title=Methylene_amidogen&action=edit&redlink=1" class="new" title="Methylene amidogen (page does not exist)">Methylene amidogen</a></li> <li><a href="/wiki/Propynylidyne" title="Propynylidyne">Propynylidyne</a></li> <li><a href="/w/index.php?title=Protonated_carbon_dioxide&action=edit&redlink=1" class="new" title="Protonated carbon dioxide (page does not exist)">Protonated carbon dioxide</a></li> <li><a href="/wiki/Protonated_hydrogen_cyanide" title="Protonated hydrogen cyanide">Protonated hydrogen cyanide</a></li> <li><a href="/w/index.php?title=Silicon_tricarbide&action=edit&redlink=1" class="new" title="Silicon tricarbide (page does not exist)">Silicon tricarbide</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li> <li><a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Five<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Polyyne" title="Polyyne">Butadiynyl</a></li> <li><a href="/wiki/Carbodiimide" title="Carbodiimide">Carbodiimide</a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">Cyanamide</a></li> <li><a href="/wiki/Cyanoacetylene" title="Cyanoacetylene">Cyanoacetylene</a></li> <li><a href="/w/index.php?title=Cyanoformaldehyde&action=edit&redlink=1" class="new" title="Cyanoformaldehyde (page does not exist)">Cyanoformaldehyde</a></li> <li><a href="/wiki/Cyanomethyl" title="Cyanomethyl">Cyanomethyl</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a class="mw-selflink selflink">Formic acid</a></li> <li><a href="/w/index.php?title=Isocyanoacetylene&action=edit&redlink=1" class="new" title="Isocyanoacetylene (page does not exist)">Isocyanoacetylene</a></li> <li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li> <li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">Methoxy radical</a></li> <li><a href="/w/index.php?title=Methylenimine&action=edit&redlink=1" class="new" title="Methylenimine (page does not exist)">Methylenimine</a></li> <li><a href="/w/index.php?title=Propadienylidene&action=edit&redlink=1" class="new" title="Propadienylidene (page does not exist)">Propadienylidene</a></li> <li><a href="/w/index.php?title=Protonated_formaldehyde&action=edit&redlink=1" class="new" title="Protonated formaldehyde (page does not exist)">Protonated formaldehyde</a></li> <li><a href="/wiki/Silane" title="Silane">Silane</a></li> <li><a href="/w/index.php?title=Silicon-carbide_cluster&action=edit&redlink=1" class="new" title="Silicon-carbide cluster (page does not exist)">Silicon-carbide cluster</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Six<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li> <li><a href="/w/index.php?title=Cyanobutadiynyl_radical&action=edit&redlink=1" class="new" title="Cyanobutadiynyl radical (page does not exist)">Cyanobutadiynyl radical</a></li> <li><a href="/wiki/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</a></li> <li><a href="/w/index.php?title=E-Cyanomethanimine&action=edit&redlink=1" class="new" title="E-Cyanomethanimine (page does not exist)">E-Cyanomethanimine</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Formamide" title="Formamide">Formamide</a></li> <li><a href="/w/index.php?title=HC4N&action=edit&redlink=1" class="new" title="HC4N (page does not exist)">HC<sub>4</sub>N</a></li> <li><a href="/wiki/Ketenimine" class="mw-redirect" title="Ketenimine">Ketenimine</a></li> <li><a href="/wiki/Methanethiol" title="Methanethiol">Methanethiol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methyl_isocyanide" title="Methyl isocyanide">Methyl isocyanide</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Pentynylidyne</a></li> <li><a href="/wiki/Propynal" class="mw-redirect" title="Propynal">Propynal</a></li> <li><a href="/w/index.php?title=Protonated_cyanoacetylene&action=edit&redlink=1" class="new" title="Protonated cyanoacetylene (page does not exist)">Protonated cyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Seven<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Acrylonitrile" title="Acrylonitrile">Acrylonitrile</a> <ul><li><a href="/wiki/Vinyl_cyanide" class="mw-redirect" title="Vinyl cyanide">Vinyl cyanide</a></li></ul></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodiacetylene</a></li> <li><a href="/wiki/Ethylene_oxide" title="Ethylene oxide">Ethylene oxide</a></li> <li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li> <li><a href="/wiki/Hexatriynyl_radical" title="Hexatriynyl radical">Hexatriynyl radical</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">Vinyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Eight<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li> <li><a href="/wiki/Aminoacetonitrile" title="Aminoacetonitrile">Aminoacetonitrile</a></li> <li><a href="/w/index.php?title=Cyanoallene&action=edit&redlink=1" class="new" title="Cyanoallene (page does not exist)">Cyanoallene</a></li> <li><a href="/wiki/Ethanimine" title="Ethanimine">Ethanimine</a></li> <li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Hexapentaenylidene</a></li> <li><a href="/wiki/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methylcyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Nine<br />atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetamide" title="Acetamide">Acetamide</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanohexatriyne</a></li> <li><a href="/wiki/Dimethyl_ether" title="Dimethyl ether">Dimethyl ether</a></li> <li><a href="/wiki/Ethanethiol" title="Ethanethiol">Ethanethiol</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyldiacetylene</a></li> <li><a href="/wiki/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</a></li> <li><a href="/wiki/Octatetraynyl_radical" title="Octatetraynyl radical">Octatetraynyl radical</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Propionitrile" title="Propionitrile">Propionitrile</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Ten<br />atoms<br />or more</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Benzonitrile" title="Benzonitrile">Benzonitrile</a></li> <li><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene">Buckminsterfullerene</a> (C<sub>60</sub>, C<sub>60</sub><sup>+</sup>, fullerene, buckyball)</li> <li><a href="/wiki/Butyronitrile" title="Butyronitrile">Butyronitrile</a></li> <li><a href="/wiki/C70_fullerene" title="C70 fullerene">C<sub>70</sub> fullerene</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodecapentayne</a></li> <li><a href="/wiki/Ethyl_formate" title="Ethyl formate">Ethyl formate</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/w/index.php?title=Heptatrienyl_radical&action=edit&redlink=1" class="new" title="Heptatrienyl radical (page does not exist)">Heptatrienyl radical</a></li> <li><a href="/wiki/Methyl_acetate" title="Methyl acetate">Methyl acetate</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Methyl-cyano-diacetylene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyltriacetylene</a></li> <li><a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deuterium" title="Deuterium">Deuterated</a><br />molecules</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Interstellar_formaldehyde#Interstellar_reactions" title="Interstellar formaldehyde">Formyl radical</a></li> <li><a href="/wiki/Heavy_water" title="Heavy water">Heavy water</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a></li> <li><a href="/wiki/Hydrogen_deuteride" title="Hydrogen deuteride">Hydrogen deuteride</a></li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>D<sup>+</sup></a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Unconfirmed</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Graphene" title="Graphene">Graphene</a></li> <li><a href="/w/index.php?title=H2NCO%2B&action=edit&redlink=1" class="new" title="H2NCO+ (page does not exist)">H<sub>2</sub>NCO<sup>+</sup></a></li> <li><a href="/wiki/Hemolithin" title="Hemolithin">Hemolithin</a></li> <li><a href="/wiki/Carbon" title="Carbon">Linear C<sub>5</sub></a></li> <li><a href="/wiki/Methoxyethane" title="Methoxyethane">Methoxyethane</a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene cation</a></li> <li><a href="/wiki/Phosphine" title="Phosphine">Phosphine</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Silylidyne" title="Silylidyne">Silylidyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#See_also" title="List of interstellar and circumstellar molecules">Related</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abiogenesis" title="Abiogenesis">Abiogenesis</a></li> <li><a href="/wiki/Astrobiology" title="Astrobiology">Astrobiology</a></li> <li><a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a></li> <li><a href="/wiki/Atomic_and_molecular_astrophysics" title="Atomic and molecular astrophysics">Atomic and molecular astrophysics</a></li> <li><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></li> <li><a href="/wiki/Circumstellar_dust" title="Circumstellar dust">Circumstellar dust</a></li> <li><a href="/wiki/Circumstellar_envelope" title="Circumstellar envelope">Circumstellar envelope</a></li> <li><a href="/wiki/Cosmic_dust" title="Cosmic dust">Cosmic dust</a></li> <li><a href="/wiki/Cosmic_ray" title="Cosmic ray">Cosmic ray</a></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a></li> <li><a href="/wiki/Diffuse_interstellar_band" class="mw-redirect" title="Diffuse interstellar band">Diffuse interstellar band</a></li> <li><a href="/wiki/Earliest_known_life_forms" title="Earliest known life forms">Earliest known life forms</a></li> <li><a href="/wiki/Extraterrestrial_life" title="Extraterrestrial life">Extraterrestrial life</a></li> <li><a href="/wiki/Extraterrestrial_liquid_water" title="Extraterrestrial liquid water">Extraterrestrial liquid water</a></li> <li><a href="/wiki/Forbidden_mechanism" title="Forbidden mechanism">Forbidden mechanism</a></li> <li><a href="/wiki/Homochirality" title="Homochirality">Homochirality</a></li> <li><a href="/wiki/Intergalactic_dust" 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