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class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Extracci%C3%B3_%C3%A0cid-base" title="Extracció àcid-base – Catalan" lang="ca" hreflang="ca" data-title="Extracció àcid-base" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Extracci%C3%B3n_%C3%A1cido-base" title="Extracción ácido-base – Spanish" lang="es" hreflang="es" data-title="Extracción ácido-base" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%D8%AE%D8%B1%D8%A7%D8%AC_%D8%A7%D8%B3%DB%8C%D8%AF%E2%80%93%D8%A8%D8%A7%D8%B2" title="استخراج اسید–باز – Persian" lang="fa" hreflang="fa" data-title="استخراج اسید–باز" 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/Extraction_acido-basique" title="Extraction acido-basique – French" lang="fr" hreflang="fr" data-title="Extraction acido-basique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Ekstraksi_asam-basa" title="Ekstraksi asam-basa – Indonesian" lang="id" hreflang="id" data-title="Ekstraksi asam-basa" 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-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Estrazione_acido-base" title="Estrazione acido-base – Italian" lang="it" hreflang="it" data-title="Estrazione acido-base" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E9%85%B8%E5%A1%A9%E5%9F%BA%E6%8A%BD%E5%87%BA" title="酸塩基抽出 – Japanese" lang="ja" hreflang="ja" data-title="酸塩基抽出" 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-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Extra%C3%A7%C3%A3o_%C3%A1cido-base" title="Extração ácido-base – Portuguese" lang="pt" hreflang="pt" data-title="Extração ácido-base" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a 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.sidebar-list-title,html.skin-theme-clientpref-night .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle{background:transparent!important}html.skin-theme-clientpref-night .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle a{color:var(--color-progressive)!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sidebar:not(.notheme) .sidebar-list-title,html.skin-theme-clientpref-os .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle{background:transparent!important}html.skin-theme-clientpref-os .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle a{color:var(--color-progressive)!important}}@media print{body.ns-0 .mw-parser-output .sidebar{display:none!important}}</style><table class="sidebar nomobile nowraplinks"><tbody><tr><th class="sidebar-title" style="background:#d3d3d3;">Acids and bases</th></tr><tr><td class="sidebar-image"><span typeof="mw:File"><a href="/wiki/File:Acetic-acid-dissociation-3D-balls.png" class="mw-file-description" title="Diagrammatic representation of the dissociation of acetic acid in aqueous solution to acetate and hydronium ions."><img alt="Diagrammatic representation of the dissociation of acetic acid in aqueous solution to acetate and hydronium ions." src="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Acetic-acid-dissociation-3D-balls.png/220px-Acetic-acid-dissociation-3D-balls.png" decoding="async" width="220" height="52" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Acetic-acid-dissociation-3D-balls.png/330px-Acetic-acid-dissociation-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/96/Acetic-acid-dissociation-3D-balls.png/440px-Acetic-acid-dissociation-3D-balls.png 2x" data-file-width="2150" data-file-height="513" /></a></span></td></tr><tr><td class="sidebar-content hlist" style="padding:0.2em 0 0.75em;"> <ul><li><a href="/wiki/Acceptor_number" class="mw-redirect" title="Acceptor number">Acceptor number</a></li> <li><a href="/wiki/Acid" title="Acid">Acid</a></li> <li><a href="/wiki/Acid%E2%80%93base_reaction" title="Acid–base reaction">Acid–base reaction</a></li> <li><a href="/wiki/Acid%E2%80%93base_homeostasis" title="Acid–base homeostasis">Acid–base homeostasis</a></li> <li><a href="/wiki/Acid_strength" title="Acid strength">Acid strength</a></li> <li><a href="/wiki/Acidity_function" title="Acidity function">Acidity function</a></li> <li><a href="/wiki/Amphoterism" title="Amphoterism">Amphoterism</a></li> <li><a href="/wiki/Base_(chemistry)" title="Base (chemistry)">Base</a></li> <li><a href="/wiki/Buffer_solution" title="Buffer solution">Buffer solutions</a></li> <li><a href="/wiki/Dissociation_constant" title="Dissociation constant">Dissociation constant</a></li> <li><a href="/wiki/Donor_number" title="Donor number">Donor number</a></li> <li><a href="/wiki/Equilibrium_chemistry" title="Equilibrium chemistry">Equilibrium chemistry</a></li> <li><a class="mw-selflink selflink">Extraction</a></li> <li><a href="/wiki/Hammett_acidity_function" title="Hammett acidity function">Hammett acidity function</a></li> <li><a href="/wiki/PH" title="PH">pH</a></li> <li><a href="/wiki/Proton_affinity" title="Proton affinity">Proton affinity</a></li> <li><a href="/wiki/Self-ionization_of_water" title="Self-ionization of water">Self-ionization of water</a></li> <li><a href="/wiki/Acid%E2%80%93base_titration" title="Acid–base titration">Titration</a></li> <li><a href="/wiki/Lewis_acid_catalysis" title="Lewis acid catalysis">Lewis acid catalysis</a></li> <li><a href="/wiki/Frustrated_Lewis_pair" title="Frustrated Lewis pair">Frustrated Lewis pair</a></li> <li><a href="/wiki/Chiral_Lewis_acid" title="Chiral Lewis acid">Chiral Lewis acid</a></li> <li><a href="/wiki/ECW_model" title="ECW model">ECW model</a></li></ul></td> </tr><tr><th class="sidebar-heading" style="background:#e5e5e5;"> <a href="/wiki/Acid" title="Acid">Acid</a> types</th></tr><tr><td class="sidebar-content hlist" style="padding:0.2em 0 0.75em;"> <ul><li><a href="/wiki/Br%C3%B8nsted%E2%80%93Lowry_acid%E2%80%93base_theory" title="Brønsted–Lowry acid–base theory">Brønsted–Lowry</a></li> <li><a href="/wiki/Lewis_acids_and_bases" title="Lewis acids and bases">Lewis</a></li> <li><a href="/wiki/Mineral_acid" title="Mineral acid">Mineral</a></li> <li><a href="/wiki/Organic_acid" title="Organic acid">Organic</a></li> <li><a href="/wiki/Acidic_oxide" title="Acidic oxide">Oxide</a></li> <li><a href="/wiki/Strong_acid" class="mw-redirect" title="Strong acid">Strong</a></li> <li><a href="/wiki/Superacid" title="Superacid">Superacids</a></li> <li><a href="/wiki/Weak_acid" class="mw-redirect" title="Weak acid">Weak</a></li> <li><a href="/wiki/Solid_acid" title="Solid acid">Solid</a></li></ul></td> </tr><tr><th class="sidebar-heading" style="background:#e5e5e5;"> <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">Base</a> types</th></tr><tr><td class="sidebar-content hlist" style="padding:0.2em 0 0.75em;"> <ul><li><a href="/wiki/Br%C3%B8nsted%E2%80%93Lowry_acid%E2%80%93base_theory" title="Brønsted–Lowry acid–base theory">Brønsted–Lowry</a></li> <li><a href="/wiki/Lewis_acids_and_bases" title="Lewis acids and bases">Lewis</a></li> <li><a href="/wiki/Organic_base" title="Organic base">Organic</a></li> <li><a href="/wiki/Basic_oxide" title="Basic oxide">Oxide</a></li> <li><a href="/wiki/Base_(chemistry)#Strong_bases" title="Base (chemistry)">Strong</a></li> <li><a href="/wiki/Superbase" title="Superbase">Superbases</a></li> <li><a href="/wiki/Non-nucleophilic_base" title="Non-nucleophilic base">Non-nucleophilic</a></li> <li><a href="/wiki/Weak_base" title="Weak base">Weak</a></li></ul></td> </tr><tr><td class="sidebar-navbar"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Acids_and_bases" title="Template:Acids and bases"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Acids_and_bases" title="Template talk:Acids and bases"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Acids_and_bases" title="Special:EditPage/Template:Acids and bases"><abbr title="Edit this template">e</abbr></a></li></ul></div></td></tr></tbody></table> <p><b>Acid–base extraction</b> is a subclass of <a href="/wiki/Liquid%E2%80%93liquid_extraction" title="Liquid–liquid extraction">liquid–liquid extractions</a> and involves the separation of chemical species from other <a href="/wiki/Acid" title="Acid">acidic</a> or <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">basic</a> compounds.<sup id="cite_ref-:03_1-0" class="reference"><a href="#cite_note-:03-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> It is typically performed during the <a href="/wiki/Work-up_(chemistry)" class="mw-redirect" title="Work-up (chemistry)">work-up</a> step following a <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">chemical synthesis</a> to purify crude compounds<sup id="cite_ref-:0_2-0" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> and results in the product being largely free of acidic or basic impurities. A <a href="/wiki/Separatory_funnel" title="Separatory funnel">separatory funnel</a> is commonly used to perform an acid-base extraction.<sup id="cite_ref-:022_3-0" class="reference"><a href="#cite_note-:022-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Acid-base extraction utilizes the difference in <a href="/wiki/Solubility" title="Solubility">solubility</a> of a compound in its <a href="/wiki/Acid" title="Acid">acid</a> or <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a> form to induce separation.<sup id="cite_ref-:4_4-0" class="reference"><a href="#cite_note-:4-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Typically, the desired compound is changed into its charged acid or base form, causing it to become soluble in aqueous solution and thus be extracted from the non-aqueous (organic) layer.<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> Acid-base extraction is a simple alternative to more complex methods like <a href="/wiki/Chromatography" title="Chromatography">chromatography</a>. It is not possible to separate chemically similar acids or bases using this simple method.<sup id="cite_ref-:1_6-0" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Background_theory">Background theory</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acid%E2%80%93base_extraction&action=edit&section=1" title="Edit section: Background theory"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <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">Further information: <a href="/wiki/Acid%E2%80%93base_reaction" title="Acid–base reaction">Acid–base reaction</a></div><p>Acid-base extraction works on the fundamental principle that <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a> are <a href="/wiki/Ionic_compound" class="mw-redirect" title="Ionic compound">ionic compounds</a> with a high solubility in water, while neutral molecules typically lack solubility in water.<sup id="cite_ref-:03_1-1" class="reference"><a href="#cite_note-:03-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Consider a mixture of acidic and basic compounds dissolved in an <a href="/wiki/Organic_solvent" class="mw-redirect" title="Organic solvent">organic solvent</a>. Adding aqueous acid will cause the acidic component to stay uncharged, while the basic component will be protonated to form a salt.<sup id="cite_ref-:1_6-1" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The uncharged acid component will remain dissolved in the organic solvent, while the highly charged basic salt will migrate to the aqueous solvent.<sup id="cite_ref-:022_3-1" class="reference"><a href="#cite_note-:022-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Since the acidic and basic components are now in two different layers, they can easily be separated. </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Acid_base_diagram_-_Colourblind_friendly.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Acid_base_diagram_-_Colourblind_friendly.tif/lossless-page1-537px-Acid_base_diagram_-_Colourblind_friendly.tif.png" decoding="async" width="537" height="273" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Acid_base_diagram_-_Colourblind_friendly.tif/lossless-page1-806px-Acid_base_diagram_-_Colourblind_friendly.tif.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Acid_base_diagram_-_Colourblind_friendly.tif/lossless-page1-1074px-Acid_base_diagram_-_Colourblind_friendly.tif.png 2x" data-file-width="2073" data-file-height="1054" /></a><figcaption>Example of acid base extraction. A 3-component system is separated into its acid component (benzoic acid), base component (benzylamine), and neutral component (biphenyl).</figcaption></figure> <p>Alternatively, adding aqueous base will cause the acidic component to be deprotonated and form a salt, while the basic component will remain uncharged.<sup id="cite_ref-:1_6-2" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> In this case, the uncharged base will stay in the organic layer, while the highly charged acidic salt will migrate to the aqueous layer. </p><p>If the organic acid component is relatively weak and has a <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">pK<sub>a</sub></a> value of ~5 (such as a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>), adding additional acid can further improve separation by lowering the pH of the solution. This minimizes the self ionization of the organic acid component and limits its tendency to enter the aqueous layer.<sup id="cite_ref-:1_6-3" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> This principle is also applicable to an organic base when it is a relatively weak base.<sup id="cite_ref-:1_6-4" class="reference"><a href="#cite_note-:1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Although acid-base extractions are most commonly used to separate acids from bases, they can be used to separate two acids or two bases from each other. However, the acids and bases must differ greatly in strength, e.g. one strong acid and one very weak acid.<sup id="cite_ref-:03_1-2" class="reference"><a href="#cite_note-:03-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Therefore, the two acids must have a pK<sub>a</sub> (or pK<sub>b</sub>) difference that is as large as possible. For example, the following can be separated: </p> <ul><li>Very weak acids like <a href="/wiki/Phenol" title="Phenol">phenols</a> (pK<sub>a</sub> around 10) from stronger acids like <a href="/wiki/Benzoic_acid" title="Benzoic acid">carboxylic acids</a><sup id="cite_ref-:03_1-3" class="reference"><a href="#cite_note-:03-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> (pK<sub>a</sub> around 4–5).</li> <li>Very weak bases (pK<sub>b</sub> around 13–14) from stronger bases (pK<sub>b</sub> around 3–4). This is frequently used in purifying soil to determine trace metal concentration.<sup id="cite_ref-:3_7-0" class="reference"><a href="#cite_note-:3-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></li></ul> <p>When separating two acids or two bases, the pH is usually adjusted to a value roughly between the pK<sub>a</sub> (or pK<sub>b</sub>) constants.<sup id="cite_ref-:03_1-4" class="reference"><a href="#cite_note-:03-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Separation occurs at this intermediate pH because one component is fully ionized, while the other is fully in its neutral form. Often, the solutions used to extract the acids or bases can also be used to control the pH. When separating two acids, the mixture is first washed with a weak base (e.g. <a href="/wiki/Sodium_bicarbonate" title="Sodium bicarbonate">sodium bicarbonate</a>) to extract the strong acid, then washed with a strong base (e.g. <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a>) to extract the weak acid.<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> For separating basic components, weak acid (e.g. dilute <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>) is first used to extract the stronger base, then more concentrated acid (e.g. <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> or <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a>) is used to create strongly acidic pH values and separate the weaker base.<sup id="cite_ref-:022_3-2" class="reference"><a href="#cite_note-:022-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:3_7-1" class="reference"><a href="#cite_note-:3-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Technique">Technique</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acid%E2%80%93base_extraction&action=edit&section=2" title="Edit section: Technique"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The following procedure is typically followed when performing an acid-base extraction for a mixture containing an acidic and/or basic compound: </p> <ol><li>The mixture of compounds is dissolved in a suitable organic solvent, such as <a href="/wiki/Dichloromethane" title="Dichloromethane">dichloromethane</a> or <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>.<figure typeof="mw:File/Thumb"><a href="/wiki/File:Final_version_-_Acid_base_extraction_flowchart.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Final_version_-_Acid_base_extraction_flowchart.tif/lossless-page1-549px-Final_version_-_Acid_base_extraction_flowchart.tif.png" decoding="async" width="549" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Final_version_-_Acid_base_extraction_flowchart.tif/lossless-page1-824px-Final_version_-_Acid_base_extraction_flowchart.tif.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Final_version_-_Acid_base_extraction_flowchart.tif/lossless-page1-1098px-Final_version_-_Acid_base_extraction_flowchart.tif.png 2x" data-file-width="4140" data-file-height="1172" /></a><figcaption>Example of acid-base extraction of two components: acidic phenol, and basic phenylamine. Phenylamine is first collected in the organic layer, then phenol is collected from the aqueous layer. The green layer in the separatory funnel indicates the organic layer, while the colourless layer indicates the aqueous layer.</figcaption></figure></li> <li>The solution is added to a separatory funnel. If the desired compound is basic, the solution will be washed with aqueous acid (e.g. 5% HCl); if it is acidic, the solution is washed with aqueous base (e.g. 5% NaOH).<sup id="cite_ref-:02_9-0" class="reference"><a href="#cite_note-:02-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></li> <li>The fractions are then shaken and the two phases are separated. The separatory funnel must be vented frequently to alleviate pressure build-up, especially when containing aqueous solutions that evolve carbon dioxide gas upon neutralization (such as <a href="/wiki/Sodium_bicarbonate" title="Sodium bicarbonate">sodium bicarbonate</a>).<sup id="cite_ref-:02_9-1" class="reference"><a href="#cite_note-:02-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></li> <li>The fraction containing the analyte of interest is then collected. Typically, this is the aqueous layer, as addition of acid or base has caused the analyte to become charged and highly soluble in the aqueous layer.<sup id="cite_ref-:02_9-2" class="reference"><a href="#cite_note-:02-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> The identity of the aqueous layer depends critically on the organic solvent's density. Organic solvents with a <a href="/wiki/Density" title="Density">density</a> greater than 1.00 g/mL (e.g. dichloromethane) cause the aqueous layer to float to the top, while solvents with a density lower than 1.00 g/mL (e.g. ether) cause the aqueous layer to sink to the bottom.<sup id="cite_ref-:02_9-3" class="reference"><a href="#cite_note-:02-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></li> <li>The organic fraction is added to the separatory funnel again, and steps 2-4 are repeated twice more to maximize the yield of the extraction. On the final rinse, a <a href="/wiki/Brine" title="Brine">brine</a> solution drives any remaining aqueous solution out of the organic layer.<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></li> <li>If the remaining organic layer contains no analytes of interest, it is discarded; otherwise, the solvent is dried over a suitable drying agent (such as anhydrous <a href="/wiki/Sodium_sulfate" title="Sodium sulfate">sodium sulfate</a>), filtered, then evaporated under reduced pressure to yield the pure compound. If the aqueous layer contains the analyte of interest, it is adjusted to the opposite pH (e.g. basic to acidic). Steps 1-4 are repeated with this fraction using an aqueous solution of opposite pH (e.g. NaOH to HCl). This circular procedure is performed since it is typically much easier to remove organic solvent via <a href="/wiki/Rotary_evaporator" title="Rotary evaporator">rotary evaporation</a> than aqueous solvent.<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></li></ol> <div class="mw-heading mw-heading2"><h2 id="Common_uses_in_chemical_synthesis">Common uses in chemical synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acid%E2%80%93base_extraction&action=edit&section=3" title="Edit section: Common uses in chemical synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acid-base extraction is frequently used as the first step in a <a href="/wiki/Work-up_(chemistry)" class="mw-redirect" title="Work-up (chemistry)">work-up</a> procedure following a <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">chemical synthesis</a><sup id="cite_ref-:0_2-1" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> to remove acidic and basic starting materials or impurities.<sup id="cite_ref-:022_3-3" class="reference"><a href="#cite_note-:022-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Acid-base extraction is typically a precursor to more complicated purification techniques, such as <a href="/wiki/Recrystallization_(chemistry)" title="Recrystallization (chemistry)">recrystallization</a>, if the product synthesized is still not completely pure.<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> </p><p><a href="/wiki/Organic_synthesis" title="Organic synthesis">Organic synthesis</a> often uses acid-base extractions during work-up procedures. For example, consider a <a href="/wiki/Fischer_esterification" class="mw-redirect" title="Fischer esterification">Fischer esterification</a> –– the condensation of a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> with an <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a> to form an <a href="/wiki/Ester" title="Ester">ester</a>. The post-reaction mixture often consists of small amounts of leftover acid and alcohol, in addition to the desired ester.<sup id="cite_ref-:04_13-0" class="reference"><a href="#cite_note-:04-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Acid-base extraction can be used to easily separate out the acidic starting materials from the ester. By rinsing the crude product mixture with a weak base (e.g. <a href="/wiki/Sodium_bicarbonate" title="Sodium bicarbonate">sodium bicarbonate</a>), the carboxylic acid and alcohol will be washed away with the aqueous layer, leaving purified ester in the organic layer.<sup id="cite_ref-:2_14-0" class="reference"><a href="#cite_note-:2-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> The choice of base used for extraction is critical, as a strong base (e.g. <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a>) will <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolyze</a> the ester. </p><p>Another common example of acid-base extraction occurs following <a href="/wiki/Peptide_synthesis" title="Peptide synthesis">peptide coupling</a>, where the amide product must be separated from leftover carboxylic acid and <a href="/wiki/Amine" title="Amine">amine</a>. The carboxylic acid can be removed by rinsing the organic layer with weak base (sodium bicarbonate), while the amine can be removed by rinsing with a weak acid (10% <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a>).<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Following these two extractions, the amide will remain in the organic layer and has been significantly purified. </p> <div class="mw-heading mw-heading2"><h2 id="Troubleshooting">Troubleshooting</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acid%E2%80%93base_extraction&action=edit&section=4" title="Edit section: Troubleshooting"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The following issues are commonly observed during acid-base extraction and typically have simple solutions </p> <ul><li><b>Only one layer is observed in the separatory funnel.</b> <ul><li>This is due to using an organic solvent with significant miscibility with water (e.g. <a href="/wiki/Acetonitrile" title="Acetonitrile">acetonitrile</a>). The organic solvent used must be water-insoluble to observe phase separation and perform an acid-base extraction.<sup id="cite_ref-:02_9-4" class="reference"><a href="#cite_note-:02-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></li></ul></li></ul> <ul><li><b>Three layers form in the separatory funnel.</b> <ul><li>Often this is a result of insufficient mixing, and light stirring will solve the issue.<sup id="cite_ref-:02_9-5" class="reference"><a href="#cite_note-:02-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></li></ul></li></ul> <ul><li><b>The boundary between the organic layer and aqueous layer is not observed</b>. <ul><li>Ice can be used to identify the boundary as it will float between the two layers.<sup id="cite_ref-:02_9-6" class="reference"><a href="#cite_note-:02-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></li></ul></li></ul> <ul><li><b>An <a href="/wiki/Emulsion" title="Emulsion">emulsion</a> forms and one layer is suspended in the other as tiny droplets.</b> <ul><li>This can be solved by using a glass stirring rod to gently "push" the tiny droplets into each other, eventually resulting in separation and causing the two layers to appear. Adding a small amount of brine solution can also be used to break up the emulsion; this process is termed "salting out".<sup id="cite_ref-:023_16-0" class="reference"><a href="#cite_note-:023-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Emulsions can be prevented by mixing the solutions gently rather than vigorously.</li></ul></li> <li><b>The relative positions of the aqueous/organic layers are unknown.</b> <ul><li>A small amount of water can be added to the separatory funnel. Whichever layer these droplets go into is identified as the aqueous layer.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup></li></ul></li></ul> <div class="mw-heading mw-heading2"><h2 id="Limitations">Limitations</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acid%E2%80%93base_extraction&action=edit&section=5" title="Edit section: Limitations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acid-base extraction is efficient at separating compounds with a large difference in solubility between their charged and their uncharged form.<sup id="cite_ref-:4_4-1" class="reference"><a href="#cite_note-:4-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Therefore, this procedure will not work for: </p> <ul><li><b><a href="/wiki/Zwitterion" title="Zwitterion">Zwitterions</a> with acidic and basic <a href="/wiki/Functional_group" title="Functional group">functional groups</a> in the same molecule.</b> <ul><li>For instance, glycine is soluble in water at most pH values<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> and is therefore difficult to be extracted into organic media.</li></ul></li> <li><b><a href="/wiki/Lipophilicity" title="Lipophilicity">Lipophilic</a> compounds.</b> <ul><li>Compounds such as <a href="/wiki/Tetrabutylammonium" title="Tetrabutylammonium">tetrabutylammonium</a> salts or <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a> do not easily dissolve in the aqueous phase in their charged form.<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></li></ul></li> <li><b>Basic amines.</b> <ul><li>Amines like <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>, <a href="/wiki/Methylamine" title="Methylamine">methylamine</a>, or <a href="/wiki/Triethanolamine" title="Triethanolamine">triethanolamine</a> are miscible or significantly soluble in water at most pH and cannot be extracted into organic media.<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></li></ul></li> <li><b>Hydrophilic inorganic acids.</b> <ul><li>Acids like <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> are indefinitely miscible in water and have limited solubility in organic solvents.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup></li></ul></li></ul> <div class="mw-heading mw-heading2"><h2 id="Alternatives">Alternatives</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acid%E2%80%93base_extraction&action=edit&section=6" title="Edit section: Alternatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alternatives to acid–base extraction include: </p> <ul><li>Filtering the mixture through a plug of <a href="/wiki/Silica_gel" title="Silica gel">silica gel</a> or <a href="/wiki/Alumina" class="mw-redirect" title="Alumina">alumina</a> — if the product is a charged salt, it will remain strongly adsorbed to the silica gel or alumina.<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></li> <li><a href="/wiki/Ion_exchange_chromatography" class="mw-redirect" title="Ion exchange chromatography">Ion exchange chromatography</a> can separate acids, bases, or mixtures of strong and weak acids and bases by their varying affinities to the column medium at different pH.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup></li> <li>Using <a href="/wiki/Column_chromatography" title="Column chromatography">column chromatography</a> to separate the neutral compounds according to their ratio-of-fronts values.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Gel_electrophoresis" title="Gel electrophoresis">Gel electrophoresis</a>, which separates large biomolecules based on their charge and size.<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></li></ul> <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=Acid%E2%80%93base_extraction&action=edit&section=7" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Chromatography" title="Chromatography">Chromatography</a></li> <li><a href="/wiki/Extraction_(chemistry)" title="Extraction (chemistry)">Extraction</a></li> <li><a href="/wiki/Multiphasic_liquid" title="Multiphasic liquid">Multiphasic liquid</a></li> <li><a href="/wiki/Separating_funnel" class="mw-redirect" title="Separating funnel">Separating funnel</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=Acid%E2%80%93base_extraction&action=edit&section=8" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-:03-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-:03_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:03_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:03_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:03_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-:03_1-4"><sup><i><b>e</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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://chem.libretexts.org/Ancillary_Materials/Demos_Techniques_and_Experiments/General_Lab_Techniques/Acid-Base_Extraction">"Acid-Base Extraction"</a>. <i>Chemistry LibreTexts</i>. 2013-10-03<span class="reference-accessdate">. Retrieved <span class="nowrap">2022-10-23</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Chemistry+LibreTexts&rft.atitle=Acid-Base+Extraction&rft.date=2013-10-03&rft_id=https%3A%2F%2Fchem.libretexts.org%2FAncillary_Materials%2FDemos_Techniques_and_Experiments%2FGeneral_Lab_Techniques%2FAcid-Base_Extraction&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcid%E2%80%93base+extraction" class="Z3988"></span></span> </li> <li id="cite_note-:0-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFXuHammond2014" class="citation journal cs1">Xu, Bo; Hammond, Gerald B. 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class="external text" href="http://web.centre.edu/muzyka/organic/lab/24_extraction.htm">Acid base extraction</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160303182415/http://web.centre.edu/muzyka/organic/lab/24_extraction.htm">Archived</a> 2016-03-03 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></li></ul> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output 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.navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Separation_processes" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="3"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Separation_processes" title="Template:Separation processes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Separation_processes" title="Template talk:Separation processes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Separation_processes" title="Special:EditPage/Template:Separation processes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Separation_processes" style="font-size:114%;margin:0 4em"><a href="/wiki/Separation_process" title="Separation process">Separation processes</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Processes</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sorption" title="Sorption">Absorption</a></li> <li><a class="mw-selflink selflink">Acid–base extraction</a></li> <li><a href="/wiki/Adsorption" title="Adsorption">Adsorption</a></li> <li><a href="/wiki/Chromatography" title="Chromatography">Chromatography</a></li> <li><a href="/wiki/Cross-flow_filtration" title="Cross-flow filtration">Cross-flow filtration</a></li> <li><a href="/wiki/Crystallization" title="Crystallization">Crystallization</a></li> <li><a href="/wiki/Cyclonic_separation" title="Cyclonic separation">Cyclonic separation</a></li> <li><a href="/wiki/Decantation" title="Decantation">Decantation</a></li> <li><a href="/wiki/Dialysis_(chemistry)" title="Dialysis (chemistry)">Dialysis</a></li> <li><a href="/wiki/Dissolved_air_flotation" title="Dissolved air flotation">Dissolved air flotation</a></li> <li><a href="/wiki/Distillation" title="Distillation">Distillation</a></li> <li><a href="/wiki/Drying" title="Drying">Drying</a></li> <li><a href="/wiki/Electrochromatography" title="Electrochromatography">Electrochromatography</a></li> <li><a href="/wiki/Electrofiltration" title="Electrofiltration">Electrofiltration</a></li> <li><a href="/wiki/Extraction_(chemistry)" title="Extraction (chemistry)">Extraction</a></li> <li><a href="/wiki/Filtration" title="Filtration">Filtration</a></li> <li><a href="/wiki/Flocculation" title="Flocculation">Flocculation</a></li> <li><a href="/wiki/Froth_flotation" title="Froth flotation">Froth flotation</a></li> <li><a href="/wiki/Gravity_separation" title="Gravity separation">Gravity separation</a></li> <li><a href="/wiki/Leaching_(chemistry)" title="Leaching (chemistry)">Leaching</a></li> <li><a href="/wiki/Liquid%E2%80%93liquid_extraction" title="Liquid–liquid extraction">Liquid–liquid extraction</a></li> <li><a href="/wiki/Electroextraction" title="Electroextraction">Electroextraction</a></li> <li><a href="/wiki/Microfiltration" title="Microfiltration">Microfiltration</a></li> <li><a href="/wiki/Osmosis" title="Osmosis">Osmosis</a></li> <li><a href="/wiki/Precipitation_(chemistry)" title="Precipitation (chemistry)">Precipitation</a></li> <li><a href="/wiki/Recrystallization_(chemistry)" title="Recrystallization (chemistry)">Recrystallization</a></li> <li><a href="/wiki/Reverse_osmosis" title="Reverse osmosis">Reverse osmosis</a></li> <li><a href="/wiki/Sedimentation_(water_treatment)" title="Sedimentation (water treatment)">Sedimentation</a></li> <li><a href="/wiki/Solid-phase_extraction" title="Solid-phase extraction">Solid-phase extraction</a></li> <li><a href="/wiki/Sublimation_(phase_transition)" title="Sublimation (phase transition)">Sublimation</a></li> <li><a href="/wiki/Ultrafiltration" title="Ultrafiltration">Ultrafiltration</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="4" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/File:ChemSepProcDiagram.svg" class="mw-file-description" title="Separation process schematic"><img alt="Separation process schematic" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/ChemSepProcDiagram.svg/81px-ChemSepProcDiagram.svg.png" decoding="async" width="81" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/ChemSepProcDiagram.svg/122px-ChemSepProcDiagram.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f9/ChemSepProcDiagram.svg/162px-ChemSepProcDiagram.svg.png 2x" data-file-width="658" data-file-height="510" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Devices</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/API_oil%E2%80%93water_separator" title="API oil–water separator">API oil–water separator</a></li> <li><a href="/wiki/Belt_filter" title="Belt filter">Belt filter</a></li> <li><a href="/wiki/Centrifuge" title="Centrifuge">Centrifuge</a></li> <li><a href="/wiki/Depth_filter" title="Depth filter">Depth filter</a></li> <li><a href="/wiki/Electrostatic_precipitator" title="Electrostatic precipitator">Electrostatic precipitator</a></li> <li><a href="/wiki/Evaporator" title="Evaporator">Evaporator</a></li> <li><a href="/wiki/Filter_press" title="Filter press">Filter press</a></li> <li><a href="/wiki/Fractionating_column" title="Fractionating column">Fractionating column</a></li> <li><a href="/wiki/Leachate" title="Leachate">Leachate</a></li> <li><a href="/wiki/Mixer-settler" title="Mixer-settler">Mixer-settler</a></li> <li><a href="/wiki/Protein_skimmer" title="Protein skimmer">Protein skimmer</a></li> <li><a href="/wiki/Rapid_sand_filter" title="Rapid sand filter">Rapid sand filter</a></li> <li><a href="/wiki/Rotary_vacuum-drum_filter" title="Rotary vacuum-drum filter">Rotary vacuum-drum filter</a></li> <li><a href="/wiki/Scrubber" title="Scrubber">Scrubber</a></li> <li><a href="/wiki/Spinning_cone" title="Spinning cone">Spinning cone</a></li> <li><a href="/wiki/Still" title="Still">Still</a></li> <li><a href="/wiki/Sublimation_apparatus" class="mw-redirect" title="Sublimation apparatus">Sublimation apparatus</a></li> <li><a href="/wiki/Vacuum_ceramic_filter" title="Vacuum ceramic filter">Vacuum ceramic filter</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Multiphase<br /> systems</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aqueous_two-phase_system" title="Aqueous two-phase system">Aqueous two-phase system</a></li> <li><a href="/wiki/Azeotrope" title="Azeotrope">Azeotrope</a></li> <li><a href="/wiki/Eutectic_system" title="Eutectic system">Eutectic</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Concepts</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Unit_operation" title="Unit operation">Unit operation</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Acid–base_extraction&oldid=1208923231">https://en.wikipedia.org/w/index.php?title=Acid–base_extraction&oldid=1208923231</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Extraction_(chemistry)" title="Category:Extraction (chemistry)">Extraction (chemistry)</a></li><li><a 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