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Ring-opening polymerization

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<div class="quotebox-title" style=""><a href="International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a> definition</div>

A <a href="Polymerization" title="Polymerization">polymerization</a> in which a <a href="Cyclic_compound" title="Cyclic compound">cyclic</a> <a href="Monomer" title="Monomer">monomer</a> yields a monomeric unit which is <a href="Open-chain_compound" title="Open-chain compound">acyclic</a> or contains fewer cycles than the monomer.

Note:

If monomer is <a href="Polycyclic_compound" title="Polycyclic compound">polycyclic</a>, the opening of a single ring is sufficient to classify the <a href="Chemical_reaction" title="Chemical reaction">reaction</a> as ring-opening polymerization.

Modified from the earlier definition.<a href="#cite_note-Goldbook-1">[1]</a><a href="#cite_note-PAC1996-2">[2]</a>

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<div style="padding-bottom: 0; padding-top: 0.5em"><cite class="left-aligned" style=""><a rel="nofollow" class="external text" href="http://www.iupac.org/publications/pac/80/10/2163/">Penczek S.; Moad, G. Pure Appl. Chem., 2008, 80(10), 2163-2193</a></cite></div>

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In <a href="Polymer_chemistry" title="Polymer chemistry">polymer chemistry</a>, ring-opening polymerization (ROP) is a form of <a href="Chain-growth_polymerization" title="Chain-growth polymerization">chain-growth polymerization</a> in which the <a href="End_group" title="End group">terminus</a> of a <a href="Polymer" title="Polymer">polymer</a> chain attacks <a href="Cyclic_compound" title="Cyclic compound">cyclic monomers</a> to form a longer polymer (see figure). The reactive center can be <a href="Radical_(chemistry)" title="Radical (chemistry)">radical</a>, <a href="Anion" class="mw-redirect" title="Anion">anionic</a> or <a href="Cation" class="mw-redirect" title="Cation">cationic</a>.

Ring-opening of cyclic monomers is often driven by the relief of <a href="Ring_strain" title="Ring strain">bond-angle strain</a>. Thus, as is the case for other types of polymerization, the <a href="Enthalpy" title="Enthalpy">enthalpy</a> change in ring-opening is negative.<a href="#cite_note-Young-3">[3]</a> Many rings undergo ROP.<a href="#cite_note-4">[4]</a>

<div class="mw-heading mw-heading2"><h2 id="Monomers">Monomers</h2></div>

Many <a href="Cyclic_compound" title="Cyclic compound">cyclic monomers</a> are amenable to ROP.<a href="#cite_note-5">[5]</a> These include <a href="Epoxide" title="Epoxide">epoxides</a>,<a href="#cite_note-Sarazin-6">[6]</a><a href="#cite_note-Longo-7">[7]</a> cyclic trisiloxanes, some lactones<a href="#cite_note-Sarazin-6">[6]</a><a href="#cite_note-Jerome-8">[8]</a> and <a href="Lactide" title="Lactide">lactides</a>,<a href="#cite_note-Jerome-8">[8]</a> cyclic <a href="Anhydride" class="mw-redirect" title="Anhydride">anhydrides</a>,<a href="#cite_note-Longo-7">[7]</a> <a href="Cyclic_carbonate" class="mw-redirect" title="Cyclic carbonate">cyclic carbonates</a>,<a href="#cite_note-9">[9]</a> and <a href="Amino_acid_N-carboxyanhydride" title="Amino acid N-carboxyanhydride">amino acid N-carboxyanhydrides</a>.<a href="#cite_note-10">[10]</a><a href="#cite_note-11">[11]</a> Many strained <a href="Cycloalkene" title="Cycloalkene">cycloalkenes</a>, e.g <a href="Norbornene" title="Norbornene">norbornene</a>, are suitable monomers via <a href="Ring-opening_metathesis_polymerization" title="Ring-opening metathesis polymerization">ring-opening metathesis polymerization</a>. Even highly strained <a href="Cycloalkane" title="Cycloalkane">cycloalkane</a> rings, such as <a href="Cyclopropane" title="Cyclopropane">cyclopropane</a><a href="#cite_note-12">[12]</a> and <a href="Cyclobutane" title="Cyclobutane">cyclobutane</a><a href="#cite_note-13">[13]</a> derivatives, can undergo ROP.

<div class="mw-heading mw-heading2"><h2 id="History">History</h2></div>

Ring-opening polymerization has been used since the beginning of the 1900s to produce <a href="Polymer" title="Polymer">polymers</a>. Synthesis of <a href="Polypeptides" class="mw-redirect" title="Polypeptides">polypeptides</a> which has the oldest history of ROP, dates back to the work in 1906 by Leuchs.<a href="#cite_note-14">[14]</a> Subsequently, the ROP of anhydro <a href="Sugars" class="mw-redirect" title="Sugars">sugars</a> provided <a href="Polysaccharides" class="mw-redirect" title="Polysaccharides">polysaccharides</a>, including synthetic <a href="Dextran" title="Dextran">dextran</a>, <a href="Xanthan_gum" title="Xanthan gum">xanthan gum</a>, <a href="Welan_gum" title="Welan gum">welan gum</a>, <a href="Gellan_gum" title="Gellan gum">gellan gum</a>, diutan gum, and <a href="Pullulan" title="Pullulan">pullulan</a>. Mechanisms and thermodynamics of ring-opening polymerization were established in the 1950s.<a href="#cite_note-15">[15]</a><a href="#cite_note-16">[16]</a> The first high-molecular weight polymers (Mn up to 105) with a <a href="Repeat_unit" title="Repeat unit">repeating unit</a> were prepared by ROP as early as in 1976.<a href="#cite_note-17">[17]</a><a href="#cite_note-18">[18]</a>

New research shows that ROP can be completed with cyclic esters with minimal to no use of solvents by using resonant acoustic mixing.<a href="#cite_note-19">[19]</a>

An industrial application is the production of <a href="Nylon-6" class="mw-redirect" title="Nylon-6">nylon-6</a> from <a href="Caprolactam" title="Caprolactam">caprolactam</a>.

<div class="mw-heading mw-heading2"><h2 id="Mechanisms">Mechanisms</h2></div>

Ring-opening polymerization can proceed via <a href="Radical_(chemistry)" title="Radical (chemistry)">radical</a>, anionic, or cationic polymerization as described below.<a href="#cite_note-nuyken-20">[20]</a> Additionally, radical ROP is useful in producing polymers with <a href="Functional_group" title="Functional group">functional groups</a> incorporated in the backbone chain that cannot otherwise be synthesized via conventional <a href="Chain-growth_polymerization" title="Chain-growth polymerization">chain-growth polymerization</a> of <a href="Vinyl_group" title="Vinyl group">vinyl</a> monomers. For instance, radical ROP can produce polymers with <a href="Ethers" class="mw-redirect" title="Ethers">ethers</a>, <a href="Esters" class="mw-redirect" title="Esters">esters</a>, <a href="Amide" title="Amide">amides</a>, and <a href="Carbonates" class="mw-redirect" title="Carbonates">carbonates</a> as functional groups along the main chain.<a href="#cite_note-nuyken-20">[20]</a><a href="#cite_note-dubois-21">[21]</a>

<div class="mw-heading mw-heading3"><h3 id="Anionic_ring-opening_polymerization_(AROP)">Anionic ring-opening polymerization (AROP)</h3></div>

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</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="Anionic_polymerization" class="mw-redirect" title="Anionic polymerization">Anionic polymerization</a></div>

Anionic ring-opening polymerizations (AROP) involve <a href="Nucleophile" title="Nucleophile">nucleophilic reagents</a> as initiators. Monomers with a three-member ring structure - such as <a href="Epoxides" class="mw-redirect" title="Epoxides">epoxides</a>, <a href="Aziridines" title="Aziridines">aziridines</a>, and episulfides - undergo anionic ROP.<a href="#cite_note-dubois-21">[21]</a>

A typical example of anionic ROP is that of <a href="Caprolactone" title="Caprolactone">ε-caprolactone</a>, initiated by an <a href="Alkoxide" title="Alkoxide">alkoxide</a>.<a href="#cite_note-dubois-21">[21]</a>

<div class="mw-heading mw-heading3"><h3 id="Cationic_ring-opening_polymerization">Cationic ring-opening polymerization</h3></div>

<div role="note" class="hatnote navigation-not-searchable">Main article: <a href="Cationic_polymerization" title="Cationic polymerization">Cationic polymerization</a></div>

Cationic initiators and intermediates characterize cationic ring-opening polymerization (CROP). Examples of <a href="Cyclic_compound" title="Cyclic compound">cyclic monomers</a> that polymerize through this mechanism include <a href="Lactone" title="Lactone">lactones</a>, <a href="Lactam" title="Lactam">lactams</a>, <a href="Amine" title="Amine">amines</a>, and <a href="Ether" title="Ether">ethers</a>.<a href="#cite_note-cowie_cation-22">[22]</a> CROP proceeds through an <a href="SN1_reaction" title="SN1 reaction">SN1</a> or <a href="SN2_reaction" title="SN2 reaction">SN2</a> propagation, chain-growth process.<a href="#cite_note-nuyken-20">[20]</a> The mechanism is affected by the stability of the resulting <a href="Ion" title="Ion">cationic</a> species. For example, if the atom bearing the positive charge is stabilized by <a href="Activating_group" class="mw-redirect" title="Activating group">electron-donating groups</a>, polymerization will proceed by the SN1 mechanism.<a href="#cite_note-dubois-21">[21]</a> The cationic species is a <a href="Heteroatom" title="Heteroatom">heteroatom</a> and the chain grows by the addition of cyclic monomers thereby opening the ring system.

The monomers can be activated by <a href="Br%C3%B8nsted%E2%80%93Lowry_acid%E2%80%93base_theory" title="Brønsted–Lowry acid–base theory">Bronsted acids</a>, <a href="Carbenium_ion" title="Carbenium ion">carbenium ions</a>, <a href="Onium_compound" class="mw-redirect" title="Onium compound">onium ions</a>, and metal cations.<a href="#cite_note-nuyken-20">[20]</a>

CROP can be a <a href="Living_polymerization" title="Living polymerization">living polymerization</a> and can be terminated by nucleophilic reagents such as <a href="Alkoxy_group" title="Alkoxy group">phenoxy anions</a>, <a href="Phosphine" title="Phosphine">phosphines</a>, or <a href="Polyelectrolyte" title="Polyelectrolyte">polyanions</a>.<a href="#cite_note-nuyken-20">[20]</a> When the amount of monomers becomes depleted, termination can occur intra or intermolecularly. The active end can "backbite" the chain, forming a <a href="Macrocycle" title="Macrocycle">macrocycle</a>. <a href="Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> chain transfer is also possible, where the active end is quenched by transferring an alkyl chain to another polymer.

<div class="mw-heading mw-heading3"><h3 id="Ring-opening_metathesis_polymerization">Ring-opening metathesis polymerization</h3></div>

<div role="note" class="hatnote navigation-not-searchable">Main article: <a href="Ring-opening_metathesis_polymerization" title="Ring-opening metathesis polymerization">Ring-opening metathesis polymerization</a></div>

<a href="Ring-opening_metathesis_polymerisation" class="mw-redirect" title="Ring-opening metathesis polymerisation">Ring-opening metathesis polymerisation</a> (ROMP) produces <a href="Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">unsaturated</a> polymers from <a href="Cycloalkene" title="Cycloalkene">cycloalkenes</a> or bicycloalkenes. It requires <a href="Organometallic_chemistry" title="Organometallic chemistry">organometallic catalysts</a>.<a href="#cite_note-nuyken-20">[20]</a>

The mechanism for ROMP follows similar pathways as <a href="Olefin_metathesis" title="Olefin metathesis">olefin metathesis</a>. The initiation process involves the coordination of the cycloalkene monomer to the <a href="Transition_metal_carbene_complex" title="Transition metal carbene complex">metal alkylidene complex</a>, followed by a [2+2] type <a href="Cycloaddition" title="Cycloaddition">cycloaddition</a> to form the metallacyclobutane intermediate that cycloreverts to form a new alkylidene species.<a href="#cite_note-sutthasupa-24">[24]</a><a href="#cite_note-hartwig-25">[25]</a>

Commercially relevant <a href="Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">unsaturated</a> polymers synthesized by ROMP include poly<a href="Norbornene" title="Norbornene">norbornene</a>, poly<a href="Cyclooctene" title="Cyclooctene">cyclooctene</a>, and poly<a href="Cyclopentadiene" title="Cyclopentadiene">cyclopentadiene</a>.<a href="#cite_note-26">[26]</a>

<div class="mw-heading mw-heading2"><h2 id="Thermodynamics">Thermodynamics</h2></div>

The formal thermodynamic criterion of a given monomer polymerizability is related to a sign of the <a href="Free_enthalpy" class="mw-redirect" title="Free enthalpy">free enthalpy</a> (<a href="Gibbs_free_energy" title="Gibbs free energy">Gibbs free energy</a>) of polymerization:

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<annotation encoding="application/x-tex">{\displaystyle \Delta G_{p}(xy)=\Delta H_{p}(xy)-T\Delta S_{p}(xy)}</annotation>

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where:

<dl><dd>x and y indicate monomer and polymer states, respectively (x and/or y = l (liquid), g (<a href="Gaseous" class="mw-redirect" title="Gaseous">gaseous</a>), c (<a href="Amorphous_solid" title="Amorphous solid">amorphous solid</a>), c' (<a href="Crystalline_solid" class="mw-redirect" title="Crystalline solid">crystalline solid</a>), s (<a href="Solution_(chemistry)" title="Solution (chemistry)">solution</a>));</dd>

<dd>ΔHp(xy) is the <a href="Enthalpy" title="Enthalpy">enthalpy</a> of polymerization (SI unit: joule per kelvin);</dd>

<dd>ΔSp(xy) is the <a href="Entropy" title="Entropy">entropy</a> of polymerization (SI unit: joule);</dd>

<dd>T is the <a href="Absolute_temperature" class="mw-redirect" title="Absolute temperature">absolute temperature</a> (SI unit: kelvin).</dd></dl>

The free enthalpy of polymerization (ΔGp) may be expressed as a sum of standard enthalpy of polymerization (ΔGp°) and a term related to instantaneous monomer molecules and growing <a href="Macromolecules" class="mw-redirect" title="Macromolecules">macromolecules</a> concentrations:

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<annotation encoding="application/x-tex">{\displaystyle \Delta G_{p}=\Delta G_{p}^{\circ }+RT\ln {\frac {[\ldots -({\ce {m}})_{i+1}{\ce {m}}^{\ast }]}{[{\ce {M}}][\ldots -({\ce {m}})_{i}{\ce {m}}^{\ast }]}}}</annotation>

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where:

<dl><dd>R is the <a href="Gas_constant" title="Gas constant">gas constant</a>;</dd>

<dd>M is the monomer;</dd>

<dd>(m)i is the monomer in an initial state;</dd>

<dd>m* is the active monomer.</dd></dl>

Following <a href="Flory%E2%80%93Huggins_solution_theory" title="Flory–Huggins solution theory">Flory–Huggins solution theory</a> that the reactivity of an active center, located at a <a href="Macromolecule" title="Macromolecule">macromolecule</a> of a sufficiently long macromolecular chain, does not depend on its <a href="Degree_of_polymerization" title="Degree of polymerization">degree of polymerization</a> (DPi), and taking in to account that ΔGp° = ΔHp° − TΔSp° (where ΔHp° and ΔSp° indicate a standard polymerization enthalpy and entropy, respectively), we obtain:

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<annotation encoding="application/x-tex">{\displaystyle \Delta G_{p}=\Delta H_{p}^{\circ }-T(\Delta S_{p}^{\circ }+R\ln[M])}</annotation>

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</math><img src="./220a922430e9e4f58818db0e2be969135dd4db24.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:34.478ex; height:3.009ex;" alt="{\displaystyle \Delta G_{p}=\Delta H_{p}^{\circ }-T(\Delta S_{p}^{\circ }+R\ln[M])}" loading="lazy"></dd></dl>

At <a href="Chemical_equilibrium" title="Chemical equilibrium">equilibrium</a> (ΔGp = 0), when polymerization is complete the monomer concentration ([M]eq) assumes a value determined by standard polymerization parameters (ΔHp° and ΔSp°) and polymerization temperature:

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<annotation encoding="application/x-tex">{\displaystyle {\begin{aligned}{}[{\ce {M}}]_{\rm {eq}}&=\exp \left({\frac {\Delta H_{p}^{\circ }}{RT}}-{\frac {\Delta S_{p}^{\circ }}{R}}\right)\\[4pt]\ln {\frac {DP_{n}}{DP_{n}-1}}[{\ce {M}}]_{\rm {eq}}&={\frac {\Delta H_{p}^{\circ }}{RT}}-{\frac {\Delta S_{p}^{\circ }}{R}}\\[4pt][{\ce {M}}]_{\rm {eq}}&={\frac {DP_{n}-1}{DP_{n}}}\exp \left({\frac {\Delta H_{p}^{\circ }}{RT}}-{\frac {\Delta S_{p}^{\circ }}{R}}\right)\end{aligned}}}</annotation>

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Polymerization is possible only when [M]0 > [M]eq. Eventually, at or above the so-called <a href="Ceiling_temperature" title="Ceiling temperature">ceiling temperature</a> (Tc), at which [M]eq = [M]0, formation of the high polymer does not occur.

<math display="block" xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\begin{aligned}T_{c}&={\frac {\Delta H_{p}^{\circ }}{\Delta S_{p}^{\circ }+R\ln[{\ce {M}}]_{0}}};\quad (\Delta H_{p}^{\circ }<0,\ \Delta S_{p}^{\circ }<0)\\[4pt]T_{f}&={\frac {\Delta H_{p}^{\circ }}{\Delta S_{p}^{\circ }+R\ln[{\ce {M}}]_{0}}};\quad (\Delta H_{p}^{\circ }>0,\ \Delta S_{p}^{\circ }>0)\end{aligned}}}">

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<annotation encoding="application/x-tex">{\displaystyle {\begin{aligned}T_{c}&={\frac {\Delta H_{p}^{\circ }}{\Delta S_{p}^{\circ }+R\ln[{\ce {M}}]_{0}}};\quad (\Delta H_{p}^{\circ }<0,\ \Delta S_{p}^{\circ }<0)\\[4pt]T_{f}&={\frac {\Delta H_{p}^{\circ }}{\Delta S_{p}^{\circ }+R\ln[{\ce {M}}]_{0}}};\quad (\Delta H_{p}^{\circ }>0,\ \Delta S_{p}^{\circ }>0)\end{aligned}}}</annotation>

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For example, <a href="Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a> (THF) cannot be polymerized above Tc = 84 °C, nor cyclo-octasulfur (S8) below Tf = 159 °C.<a href="#cite_note-27">[27]</a><a href="#cite_note-28">[28]</a><a href="#cite_note-29">[29]</a><a href="#cite_note-30">[30]</a> However, for many monomers, Tc and Tf, for polymerization in the bulk, are well above or below the operable polymerization temperatures, respectively.

The polymerization of a majority of monomers is accompanied by an <a href="Entropy" title="Entropy">entropy</a> decrease, due mostly to the loss in the translational degrees of freedom. In this situation, polymerization is thermodynamically allowed only when the enthalpic contribution into ΔGp prevails (thus, when ΔHp° < 0 and ΔSp° < 0, the inequality |ΔHp| > −TΔSp is required). Therefore, the higher the ring strain, the lower the resulting monomer concentration at <a href="Chemical_equilibrium" title="Chemical equilibrium">equilibrium</a>.

<div class="mw-heading mw-heading2"><h2 id="Additional_reading">Additional reading</h2></div>

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</style><cite id="CITEREFLuckSadhir1992" class="citation book cs1">Luck, Russel M.; Sadhir, Rajender K., eds. (1992). <a href="Expanding_Monomers" class="mw-redirect" title="Expanding Monomers">Expanding Monomers: Synthesis, Characterization, and Applications</a>. Boca Raton, Florida: CRC Press. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-0-8493-5156-3</bdi>.</cite></li>

<li><cite id="CITEREFNahrain_E._KamberWonhee_JeongRobert_M._WaymouthRussell_C._Pratt2007" class="citation journal cs1">Nahrain E. Kamber; Wonhee Jeong; Robert M. Waymouth; Russell C. Pratt; Bas G. G. Lohmeijer; James L. Hedrick (2007). "Organocatalytic Ring-Opening Polymerization". Chemical Reviews. 107 (12): 5813–5840. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr068415b">10.1021/cr068415b</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17988157">17988157</a>.</cite></li>

<li><cite id="CITEREFDuboisCoulembierRaquez2009" class="citation book cs1">Dubois, Philippe; Coulembier, Olivier; Raquez, Jean-Marie, eds. (2009). Handbook of Ring-Opening Polymerization. Wiley. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9783527628407">10.1002/9783527628407</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>9783527628407</bdi>.</cite></li></ul>

<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>

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<li id="cite_note-dubois-21">^ <a href="#cite_ref-dubois_21-0">a</a> <a href="#cite_ref-dubois_21-1">b</a> <a href="#cite_ref-dubois_21-2">c</a> <a href="#cite_ref-dubois_21-3">d</a> <a href="#cite_ref-dubois_21-4">e</a> <cite id="CITEREFDubois2008" class="citation book cs1">Dubois, Philippe (2008). Handbook of ring-opening polymerization (1. Aufl. ed.). Weinheim: Wiley-VCH. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-3-527-31953-4</bdi>.</cite>

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<li id="cite_note-sutthasupa-24"><a href="#cite_ref-sutthasupa_24-0">^</a> <cite id="CITEREFSutthasupaShiotsuki,_MasashiSanda,_Fumio2010" class="citation journal cs1">Sutthasupa, Sutthira; Shiotsuki, Masashi; Sanda, Fumio (13 October 2010). <a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fpj.2010.94">"Recent advances in ring-opening metathesis polymerization, and application to synthesis of functional materials"</a>. Polymer Journal. 42 (12): 905–915. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fpj.2010.94">10.1038/pj.2010.94</a>.</cite>

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