A review of copolymerization of green house gas carbon dioxide and oxiranes to produce polycarbonate

Carbon dioxide is highly stable and low reactivity element which is known to cause greenhouse effect of the Earth. Over the decades, researches have been conducted to utilize abundant carbon dioxide to turn into value added products while reducing its impact to the environment. One of the approaches is reacting carbon dioxide with oxiranes to produce polycarbonate. The low reactivity characteristic of carbon dioxide requires effective and efficient catalysts to make the copolymerization possible. This review highlights the major development in the catalytic copolymerization process of oxiranes and carbon dioxide. Particularly, the important characteristics of zinc, aluminium, chromium, cobalt, cadmium, manganese and rare earth metal with variety of ligands catalysts have been thoroughly discussed. The future research prospects which involve working in the copolymerization area of nanocatalysis and supercritical fluid have been analysed also. In overall, continual exploration of catalysis and reaction package for copolymerization of carbon dioxide is important in order to achieve better improvement of process in future.

[1]  SonBinh T. Nguyen,et al.  Co(III) porphyrin/DMAP: an efficient catalyst system for the synthesis of cyclic carbonates from CO2 and epoxides , 2004 .

[2]  Hiroyuki Yasuda,et al.  Transformation of carbon dioxide. , 2007, Chemical reviews.

[3]  T. Tsuruta,et al.  Stereochemistry of the copolymerization of carbon dioxide with optically active phenylepoxyethane , 1975 .

[4]  A. Holmes,et al.  Polymer supported chromium porphyrin as catalyst for polycarbonate formation in supercritical carbon dioxide. , 2001, Chemical communications.

[5]  J. Clark,et al.  Keynote article. Environmentally friendly chemistry using supported reagent catalysts: structure–property relationships for clayzic , 1994 .

[6]  S. Inoue,et al.  Polymerization of 1,2‐epoxypropane and copolymerization with carbon dioxide catalyzed by metalloporphyrins , 1978 .

[7]  M. Zimmer,et al.  Catalytic activity of a series of Zn(II) phenoxides for the copolymerization of epoxides and carbon dioxide , 1999 .

[8]  M. Ashiq,et al.  Effect of substitution of K+ ions on the structural and electrical properties of nanocrystalline MgAl2O4 spinel oxide , 2011 .

[9]  Xiamei Zhong,et al.  Fabrication of biomimetic poly(propylene carbonate) scaffolds by using carbon dioxide as a solvent, monomer and foaming agent , 2012 .

[10]  T. Shin,et al.  Copolymerization of carbon dioxide and propylene oxide using various zinc glutarate derivatives as catalysts , 2000 .

[11]  Bernhard Rieger,et al.  Facile synthesis of cyclic carbonates from CO2 and epoxides with cobalt(II)/onium salt based catalysts , 2009 .

[12]  B. Subramaniam,et al.  Homogeneous Catalytic Epoxidation of Organic Substrates in CO2-Expanded Solvents in the Presence of Water-Soluble Oxidants and Catalysts , 2003 .

[13]  T. Tsuruta,et al.  Copolymerization of carbon dioxide and epoxide using dialkylzinc/dihydric phenol system as catalyst , 1973 .

[14]  G. Coates,et al.  Alternating copolymerization of limonene oxide and carbon dioxide. , 2004, Journal of the American Chemical Society.

[15]  D. Awschalom,et al.  Growth of CdS Nanorods in Nonionic Amphiphilic Triblock Copolymer Systems , 2002 .

[16]  H. Sugimoto,et al.  Alternating copolymerization of carbon dioxide and epoxide by manganese porphyrin: The first example of polycarbonate synthesis from 1‐atm carbon dioxide , 2003 .

[17]  Christine Jérôme,et al.  Input of supercritical carbon dioxide to polymer synthesis: an overview , 2014 .

[18]  J. C. Yarbrough,et al.  Bis-Salicylaldiminato Complexes of Zinc. Examination of the Catalyzed Epoxide/CO2 Copolymerization , 2001 .

[19]  D. Darensbourg,et al.  Supercritical carbon dioxide as solvent for the copolymerization of carbon dioxide and propylene oxide using a heterogeneous zinc carboxylate catalyst , 1995 .

[20]  Hong Wu,et al.  Synthesis, characterization and hydrolysis of an aliphatic polycarbonate by terpolymerization of carbon dioxide, propylene oxide and maleic anhydride , 2006 .

[21]  W. J. Kruper,et al.  Catalytic Formation of Cyclic Carbonates from Epoxides and CO2 with Chromium Metalloporphyrinates , 1995 .

[22]  M. Aresta.  Carbon dioxide as chemical feedstock , 2010 .

[23]  G. Rokicki.  Aliphatic cyclic carbonates and spiroorthocarbonates as monomers , 2000 .

[24]  J. Jung,et al.  Terpolymerization of CO2 with Propylene Oxide and ε-Caprolactone Using Zinc Glutarate Catalyst , 2003 .

[25]  G. Qi,et al.  Copolymerization of carbon dioxide and propylene oxide with highly effective zinc hexacyanocobaltate(III)-based coordination catalyst , 2004 .

[26]  B. Rieger,et al.  DMAP/Cr(III) Catalyst Ratio: The Decisive Factor for Poly(propylene carbonate) Formation in the Coupling of CO2 and Propylene Oxide , 2003 .

[27]  K. Nozaki,et al.  Copolymerization of epoxides with carbon dioxide catalyzed by iron-corrole complexes: synthesis of a crystalline copolymer. , 2013, Journal of the American Chemical Society.

[28]  D. Darensbourg,et al.  Catalytic Activity of Zinc(II) Phenoxides Which Possess Readily Accessible Coordination Sites. Copolymerization and Terpolymerization of Epoxides and Carbon Dioxide , 1995 .

[29]  Dae-Won Park,et al.  Aliphatic polycarbonate synthesis by copolymerization of carbon dioxide with epoxides over double metal cyanide catalysts prepared by using ZnX2 (X = F, Cl, Br, I) , 2006 .

[30]  David R. Moore,et al.  Discrete metal-based catalysts for the copolymerization of CO2 and epoxides: discovery, reactivity, optimization, and mechanism. , 2004, Angewandte Chemie.

[31]  E. Beckman,et al.  Copolymerization of 1,2-Epoxycyclohexane and Carbon Dioxide Using Carbon Dioxide as Both Reactant and Solvent , 1997 .

[32]  K. G. Caulton,et al.  Soluble zinc bis(aryloxides) , 1986 .

[33]  Yusheng Qin,et al.  Carbon dioxide‐based copolymers: Environmental benefits of PPC, an industrially viable catalyst , 2010, Biotechnology journal.

[34]  B. Lee,et al.  Terpolymerizations of CO2, Propylene Oxide, and Various Epoxides Using a Cobalt(III) Complex of Salen-Type Ligand Tethered by Four Quaternary Ammonium Salts , 2010 .

[35]  M. Ree,et al.  Copolymerization of carbon dioxide and propylene oxide using an aluminum porphyrin system and its components , 1999 .

[36]  Wei-Min Ren,et al.  Cobalt(III)‐complex‐mediated terpolymerization of CO2, styrene oxide, and epoxides with an electron‐donating group , 2013 .

[37]  Y. Meng,et al.  ZnGA–MMT catalyzed the copolymerization of carbon dioxide with propylene oxide , 2005 .

[38]  P. Concepción,et al.  Cobalt particle size effects in Fischer–Tropsch synthesis: structural and in situ spectroscopic characterisation on reverse micelle-synthesised Co/ITQ-2 model catalysts , 2009 .

[39]  Zheng Wang,et al.  Copolymerization of cyclohexene oxide with CO2 by using intramolecular dinuclear zinc catalysts. , 2005, Chemistry.

[40]  D. Darensbourg,et al.  Bis 2,6-difluorophenoxide Dimeric Complexes of Zinc and Cadmium and Their Phosphine Adducts: Lessons Learned Relative to Carbon Dioxide/Cyclohexene Oxide Alternating Copolymerization Processes Catalyzed by Zinc Phenoxides , 2000 .

[41]  Wei Wei,et al.  A short review of catalysis for CO2 conversion , 2009 .

[42]  K. Nozaki,et al.  Manganese-corrole complexes as versatile catalysts for the ring-opening homo- and co-polymerization of epoxide. , 2014, Chemistry.

[43]  A. Cooper,et al.  Copolymerization of CO2 and 1,2-cyclohexene oxide using a CO2-soluble chromium porphyrin catalyst , 2000 .

[44]  G. Coates,et al.  Cobalt catalysts for the alternating copolymerization of propylene oxide and carbon dioxide: combining high activity and selectivity. , 2005, Journal of the American Chemical Society.

[45]  M. Antonietti,et al.  Control of barite morphology by double-hydrophilic block copolymers. , 2000 .

[46]  Jindo Kim.  NEXAFS spectroscopy study of the surface properties of zinc glutarate and its reactivity with carbon dioxide and propylene oxide , 2003 .

[47]  Charlotte K. Williams,et al.  Efficient magnesium catalysts for the copolymerization of epoxides and CO2; using water to synthesize polycarbonate polyols. , 2012, Journal of the American Chemical Society.

[48]  K. Zhu,et al.  Synthesis, properties, and biodegradation of poly(1,3-trimethylene carbonate) , 1991 .

[49]  G. Coates,et al.  Enantiomerically-enriched organic reagents via polymer synthesis: enantioselective copolymerization of cycloalkene oxides and CO2 using homogeneous, zinc-based catalysts , 2000 .

[50]  E. Beckman.  Making Polymers from Carbon Dioxide , 1999, Science.

[51]  D. Darensbourg,et al.  Catalytic Coupling of Cyclopentene Oxide and CO2 Utilizing Bifunctional (salen)Co(III) and (salen)Cr(III) Catalysts: Comparative Processes Involving Binary (salen)Cr(III) Analogs , 2013 .

[52]  T. Aida,et al.  Synthesis of polyether-polycarbonate block copolymer from carbon dioxide and epoxide using a metalloporphyrin catalyst system , 1982 .

[53]  G. Wegner,et al.  Control of ZnO Crystallization by a PEO-b-PMAA Diblock Copolymer , 1998 .

[54]  Dae-Won Park,et al.  Biodegradable Polycarbonate Synthesis by Copolymerization of Carbon Dioxide with Epoxides Using a Heterogeneous Zinc Complex , 2005 .

[55]  R. Zhuo,et al.  Synthesis and properties of functional aliphatic polycarbonates , 2003 .

[56]  Size-dependent studies of Fischer-Tropsch synthesis on iron based catalyst: New kinetic model , 2014 .

[57]  K. Jaszcz,et al.  Synthesis of functional polycarbonates by copolymerization of carbon dioxide with allyl glycidyl ether , 2000 .

[58]  M. Ree,et al.  Hydrothermal Synthesis of Single-Crystalline Zinc Glutarate and Its Structural Determination , 2004 .

[59]  Q. Zhu,et al.  Effects of the structure and morphology of zinc glutarate on the fixation of carbon dioxide into polymer , 2002 .

[60]  R. Varma,et al.  Nano-magnetite (Fe3O4) as a support for recyclable catalysts in the development of sustainable methodologies. , 2013, Chemical Society reviews.

[61]  David R. Moore,et al.  Mechanism of the alternating copolymerization of epoxides and CO2 using beta-diiminate zinc catalysts: evidence for a bimetallic epoxide enchainment. , 2003, Journal of the American Chemical Society.

[62]  Wei-Min Ren,et al.  Alternating copolymerization of CO2 and styrene oxide with Co(III)-based catalyst systems: differences between styrene oxide and propylene oxide , 2011 .

[63]  Yi Luo,et al.  Enhanced asymmetric induction for the copolymerization of CO2 and cyclohexene oxide with unsymmetric enantiopure salenCo(III) complexes: synthesis of crystalline CO2-based polycarbonate. , 2012, Journal of the American Chemical Society.

[64]  Charlotte K. Williams,et al.  Catalysts for CO2/epoxide copolymerisation. , 2011, Chemical communications.

[65]  D. Darensbourg,et al.  Syntheses and Structures of Epoxide Adducts of Soluble Cadmium(II) Carboxylates. Models for the Initiation Process in Epoxide/CO2 Coupling Reactions , 1995 .

[66]  Martina Peters,et al.  CO₂:From waste to value , 2009 .

[67]  Wei-Min Ren,et al.  Stereoregular poly(cyclohexene carbonate)s: Unique crystallization behavior , 2012, Chinese Journal of Polymer Science.

[68]  David R. Moore,et al.  High-activity, single-site catalysts for the alternating copolymerization of CO2 and propylene oxide. , 2002, Journal of the American Chemical Society.

[69]  G. Coates,et al.  Cobalt-based complexes for the copolymerization of propylene oxide and CO2: active and selective catalysts for polycarbonate synthesis. , 2003, Angewandte Chemie.

[70]  F. Molnár,et al.  On the formation of aliphatic polycarbonates from epoxides with chromium(III) and aluminum(III) metal-salen complexes. , 2005, Chemistry.

[71]  T. Hiyama,et al.  Optically Active Polycarbonates: Asymmetric Alternating Copolymerization of Cyclohexene Oxide and Carbon Dioxide , 1999 .

[72]  Hideomi Koinuma,et al.  Copolymerization of carbon dioxide and epoxide , 1969 .

[73]  S. Inoue,et al.  Alternating copolymerization of carbon dioxide and epoxide catalyzed by the aluminum porphyrin-quaternary organic salt or -triphenylphosphine system. Synthesis of polycarbonate with well-controlled molecular weight , 1986 .

[74]  Zhi-quan Shen,et al.  New catalytic systems for the fixation of carbon dioxide. 1. Copolymerization of carbon dioxide and propylene oxide with new rare-earth catalysts-RE(P204)3-Al(i-Bu)3-R(OH)n , 1991 .

[75]  E. Beckman,et al.  Copolymerization of CO2 and cyclohexene oxide , 1998 .

[76]  Chung-Sung Tan,et al.  Alternating Copolymerization of Carbon Dioxide and Propylene Oxide with a Rare-Earth-Metal Coordination Catalyst , 1997 .

[77]  E. Dinjus,et al.  New cobalt, iron and chromium catalysts based on easy-to-handle N4-chelating ligands for the coupling reaction of epoxides with CO2. , 2014, Dalton transactions.

[78]  S. Nguyen,et al.  Chiral (salen)Co(III) catalyst for the synthesis of cyclic carbonates. , 2004, Chemical communications.

[79]  D. Darensbourg,et al.  Mechanistic Aspects of the Copolymerization of CO2 and Epoxides by Soluble Zinc Bis(phenoxide) Catalysts as Revealed by Their Cadmium Analogues , 1998 .

[80]  M. Zimmer,et al.  Solution and solid-state structures of phosphine adducts of monomeric zinc bisphenoxide complexes. Importance of these derivatives in CO2/epoxide copolymerization processes. , 2000, Inorganic chemistry.

[81]  J. DeSimone,et al.  Solid-State Polymerization of Polycarbonates Using Supercritical CO2 , 1999 .

[82]  S. Kent Hoekman,et al.  CO2 recycling by reaction with renewably-generated hydrogen , 2010 .

[83]  T. Shin,et al.  X-ray absorption and NMR spectroscopic investigations of zinc glutarates prepared from various zinc sources and their catalytic activities in the copolymerization of carbon dioxide and propylene oxide , 2003 .

[84]  C. Romain,et al.  Dinuclear metal catalysts: improved performance of heterodinuclear mixed catalysts for CO₂-epoxide copolymerization. , 2014, Chemical communications.

[85]  D. Darensbourg,et al.  Solid-state structures of zinc(II) benzoate complexes. Catalyst precursors for the coupling of carbon dioxide and epoxides. , 2002, Inorganic chemistry.

[86]  G. Coates,et al.  Copolymerization of CO2 and meso epoxides using enantioselective β-diiminate catalysts: a route to highly isotactic polycarbonates , 2014 .

[87]  Wei-Min Ren,et al.  Highly Active, Bifunctional Co(III)-Salen Catalyst for Alternating Copolymerization of CO2 with Cyclohexene Oxide and Terpolymerization with Aliphatic Epoxides , 2010 .

[88]  E. Beckman,et al.  Design and Synthesis of Low Cost, Sustainable CO2-philes , 2000 .

[89]  A. Rokicki,et al.  Copolymerization of carbon dioxide with propylene oxide in the presence of catalysts based on alkylmetal compounds and pyrogallol , 1979 .

[90]  R. Zbořil,et al.  The Effect of Surface Area and Crystal Structure on the Catalytic Efficiency of Iron(III) Oxide Nanoparticles in Hydrogen Peroxide Decomposition , 2010 .

[91]  B. Bhanage,et al.  Carbon dioxide: a renewable feedstock for the synthesis of fine and bulk chemicals , 2010 .

[92]  Wei-Min Ren,et al.  Asymmetric copolymerization of CO2 with meso-epoxides mediated by dinuclear cobalt(III) complexes: unprecedented enantioselectivity and activity. , 2013, Angewandte Chemie.

[93]  David R. Brown,et al.  Surface properties and porosities of silica and acid-treated montmorillonite catalyst supports: influence on activities of supported ZnCl2 alkylation catalysts , 1993 .

[94]  S. Tjong,et al.  Synthesis and characterization of alternating copolymer from carbon dioxide and propylene oxide , 2002 .

[95]  Paolo P. Pescarmona,et al.  Green polycarbonates prepared by the copolymerization of CO2 with epoxides , 2014 .

[96]  Yu-mei Shen,et al.  Chemical fixation of carbon dioxide catalyzed by binaphthyldiamino Zn, Cu, and Co salen-type complexes. , 2003, The Journal of organic chemistry.

[97]  D. Darensbourg,et al.  Syntheses, Structures, and Binding Constants of Cyclic Ether and Thioether Adducts of Soluble Cadmium(II) Carboxylates. Intermediates in the Homopolymerization of Oxiranes and Thiiranes and in Carbon Dioxide Coupling Processes. , 1997, Inorganic chemistry.

[98]  Charlotte K. Williams,et al.  Highly active dizinc catalyst for the copolymerization of carbon dioxide and cyclohexene oxide at one atmosphere pressure. , 2009, Angewandte Chemie.

[99]  Hyun-Chul Kim,et al.  Synthesis of zinc glutarates with various morphologies using an amphiphilic template and their catalytic activities in the copolymerization of carbon dioxide and propylene oxide , 2005 .

[100]  M. Chisholm,et al.  Concerning the mechanism of the ring opening of propylene oxide in the copolymerization of propylene oxide and carbon dioxide to give poly(propylene carbonate). , 2004, Journal of the American Chemical Society.

[101]  M. Döring,et al.  Alternating Copolymerization of Cyclohexene Oxide and CO2 Catalyzed by Zinc Complexes with New 3-Amino-2-cyanoimidoacrylate Ligands , 2005 .

[102]  S. Nguyen,et al.  Alternating Copolymerization of CO2 and Propylene Oxide Catalyzed by CoIII(salen)/Lewis Base , 2005 .

[103]  B. Rieger,et al.  New Zinc Dicarboxylate Catalysts for the CO2/Propylene Oxide Copolymerization Reaction: Activity Enhancement Through Zn(II)-Ethylsulfinate Initiating Groups , 2004 .

[104]  W. Kuran,et al.  Initiation and propagation reactions in the copolymerization of epoxide with carbon dioxide by catalysts based on diethylzinc and polyhydric phenol , 1994 .

[105]  Fosong Wang,et al.  Hydrophilic CO2-Based Biodegradable Polycarbonates: Synthesis and Rapid Thermo-Responsive Behavior , 2013 .

[106]  J. E. Lyons,et al.  Catalysis research of relevance to carbon management: progress, challenges, and opportunities. , 2001, Chemical reviews.

[107]  T. Shin,et al.  A new copolymerization process leading to poly(propylene carbonate) with a highly enhanced yield from carbon dioxide and propylene oxide , 1999 .

[108]  K. Soga,et al.  Copolymerization of carbon dioxide and epoxypropane by using cobalt(II) acetate and acetic acid , 1978 .

[109]  Frank Behrendt,et al.  Evaluation of strategies for the subsequent use of CO2 , 2010 .

[110]  Stephan Klaus,et al.  Differences in reactivity of epoxides in the copolymerisation with carbon dioxide by zinc-based catalysts: propylene oxide versus cyclohexene oxide. , 2011, Chemistry.

[111]  R. Storey,et al.  New Aliphatic Poly(ester-carbonates) Based on 5-Methyl-5-allyloxycarbonyl-1,3-dioxan-2-one (MAC) , 2003 .

[112]  D. H. Busch,et al.  CO(2)-expanded solvents: unique and versatile media for performing homogeneous catalytic oxidations. , 2002, Journal of the American Chemical Society.

[113]  M. Aresta,et al.  Utilisation of CO2 as a chemical feedstock: opportunities and challenges. , 2007, Dalton transactions.

[114]  Hyun-Chul Kim,et al.  New findings in the catalytic activity of zinc glutarate and its application in the chemical fixation of CO2 into polycarbonates and their derivatives , 2006 .

[115]  W. Jiajun,et al.  Pressure Dependence of the CO2/Propylene Oxide Copolymerization Catalyzed by Zinc Glutarate , 2010 .

[116]  Yi Wang,et al.  Highly active, binary catalyst systems for the alternating copolymerization of CO2 and epoxides under mild conditions. , 2004, Angewandte Chemie.

[117]  Geoffrey W. Coates,et al.  Catalytic Reactions Involving C1 Feedstocks: New High-Activity Zn(II)-Based Catalysts for the Alternating Copolymerization of Carbon Dioxide and Epoxides , 1998 .

[118]  D. Darensbourg,et al.  Synthesis and physical characterization of poly(cyclohexane carbonate), synthesized from CO2 and cyclohexene oxide , 2001 .

[119]  G. Centi,et al.  Opportunities and prospects in the chemical recycling of carbon dioxide to fuels , 2009 .

[120]  Xiamei Zhong,et al.  Solvent free synthesis of organometallic catalysts for the copolymerisation of carbon dioxide and propylene oxide , 2010 .

[121]  Tianpin Wu,et al.  Selective hydrogenation of acrolein on supported silver catalysts: A kinetics study of particle size effects , 2013 .

[122]  G. Coates,et al.  Single-site beta-diiminate zinc catalysts for the alternating copolymerization of CO2 and epoxides: catalyst synthesis and unprecedented polymerization activity. , 2001, Journal of the American Chemical Society.

[123]  E. Dinjus,et al.  Synthesis of cyclic carbonates from epoxides and carbon dioxide catalyzed by an easy-to-handle ionic iron(III) complex. , 2013, Dalton transactions.

[124]  S. Nguyen,et al.  (Salen)chromium(III)/DMAP: an efficient catalyst system for the selective synthesis of 5-substituted oxazolidinones from carbon dioxide and aziridines. , 2004, Organic letters.

[125]  J. C. Yarbrough,et al.  Solution and solid-state structural studies of epoxide adducts of cadmium phenoxides. Chemistry relevant to epoxide activation for ring-opening reactions. , 2002, Journal of the American Chemical Society.

[126]  Fosong Wang,et al.  Biodegradable CO2‐based polycarbonates with rapid and reversible thermal response at body temperature , 2013 .

[127]  D. Navarro-Llobet,et al.  Poly(propylene carbonate). 1. More about Poly(propylene carbonate) Formed from the Copolymerization of Propylene Oxide and Carbon Dioxide Employing a Zinc Glutarate Catalyst , 2002 .

[128]  S. Inoue,et al.  Activation of Carbon Dioxide by Tetraphenylporphinatoaluminium Methoxide. Reaction with Epoxide , 1978 .

[129]  Charlotte K. Williams,et al.  A bimetallic iron(III) catalyst for CO2/epoxide coupling. , 2011, Chemical communications.