Convenient synthesis of cyclic carbonates from CO2 and epoxides by simple secondary and primary ammonium iodides as metal-free catalysts under mild conditions and its application to synthesis of polymer bearing cyclic carbonate moiety

被引:68
作者
Aoyagi, Naoto [1 ]
Furusho, Yoshio [1 ]
Endo, Takeshi [1 ]
机构
[1] Kinki Univ, Mol Engn Inst, Iizuka, Fukuoka 8208555, Japan
关键词
CO2; cyclic carbonate; catalysts; copolymerization; heteroatom-containing polymers; N-HETEROCYCLIC CARBENES; PROPYLENE CARBONATE; CHEMICAL FIXATION; IONIC LIQUIDS; RADICAL POLYMERIZATION; ETHYLENE CARBONATE; LITHIUM ELECTRODE; LATTICE ENERGIES; HYBRID CATALYST; DIOXIDE;
D O I
10.1002/pola.26492
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Hydroiodides of secondary and primary amines effectively catalyzed the reaction of carbon dioxide and epoxides under mild conditions such as ordinary pressure and ambient temperature, to obtain the corresponding five-membered cyclic carbonates in moderate to high yields. Detailed investigation showed that the catalytic activity was highly affected by the counter anions of the ammonium salts; the iodides catalyzed efficiently the carbonate-forming reactions, whereas the bromide and chloride counterparts exhibited almost no catalysis. We also revealed that two important factors on the amine moieties that affected the catalytic reactions. First, the catalytic activity increased with increasing bulkiness of the substituents on the ammonium nitrogen atoms. Second, the catalysis became more efficient as the parent amines become more basic. Dicyclohexylammonium iodide was the best catalyst among the ammonium salts investigated in this study. As an application of this reaction system, we synthesized homo- and copolymers bearing epoxide pendant groups as substrates, which were converted with high efficiency into the corresponding homo- and copolymers bearing cyclic carbonate pendant groups under 1 atm at 45 degrees C. All polymers were easily purified simply by precipitation in water, and were isolated in high yields (>95%). (c) 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013
引用
收藏
页码:1230 / 1242
页数:13
相关论文
共 116 条
  • [1] The polymer incarcerated method for the preparation of highly active heterogeneous palladium catalysts
    Akiyama, R
    Kobayashi, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (12) : 3412 - 3413
  • [2] Cobaltoporphyrin-Catalyzed CO2/Epoxide Copolymerization: Selectivity Control by Molecular Design
    Anderson, Carly E.
    Vagin, Sergei I.
    Xia, Wei
    Jin, Hanpeng
    Rieger, Bernhard
    [J]. MACROMOLECULES, 2012, 45 (17) : 6840 - 6849
  • [3] DIALKYLAMMONIUM ION CROWN-ETHER COMPLEXES - THE FORERUNNERS OF A NEW FAMILY OF INTERLOCKED MOLECULES
    ASHTON, PR
    CAMPBELL, PJ
    CHRYSTAL, EJT
    GLINK, PT
    MENZER, S
    PHILP, D
    SPENCER, N
    STODDART, JF
    TASKER, PA
    WILLIAMS, DJ
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17): : 1865 - 1869
  • [4] Solution structure of lithium dicyclohexylamide (Cy(2)NLi) and related mixed aggregates: Comparison with lithium diisopropylamide
    Aubrecht, KB
    Collum, DB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) : 8674 - 8676
  • [5] CARBONATE FORMATION FROM OXIRANES AND CARBON-DIOXIDE CATALYZED BY ORGANOTIN HALIDE-TETRAALKYLPHOSPHONIUM HALIDE-COMPLEXES
    BABA, A
    NOZAKI, T
    MATSUDA, H
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (04) : 1552 - 1554
  • [6] Cycloaddition of CO2 to epoxides over both homogeneous and silica-supported guanidine catalysts
    Barbarini, A
    Maggi, R
    Mazzacani, A
    Mori, G
    Sartori, G
    Sartorio, R
    [J]. TETRAHEDRON LETTERS, 2003, 44 (14) : 2931 - 2934
  • [7] Synthesis of a Methacrylic Monomer Having Pendant Cyclohexene Cyclic Carbonate Easy-CO2 Fixation and Radical Polymerization
    Barkakaty, Balaka
    Morino, Kazuhide
    Sudo, Atsushi
    Endo, Takeshi
    [J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2011, 49 (02) : 545 - 549
  • [8] Amidine-mediated delivery of CO2 from gas phase to reaction system for highly efficient synthesis of cyclic carbonates from epoxides
    Barkakaty, Balaka
    Morino, Kazuhide
    Sudo, Atsushi
    Endo, Takeshi
    [J]. GREEN CHEMISTRY, 2010, 12 (01) : 42 - 44
  • [9] Propylene carbonate as a solvent for asymmetric Hydrogenations
    Bayardon, Jerome
    Holz, Jens
    Schaeffner, Benjamin
    Andrushko, Vasyl
    Verevkin, Sergej
    Preetz, Angelika
    Boerner, Armin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (31) : 5971 - 5974
  • [10] New succinamic acids, -γ-lactones, and -succinimides from (3-perfluoroalkyl-2-iodoalkyl)succinic acid anhydrides and amines -: Highly surface active amphiphiles
    Brace, NO
    Mull, SG
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (01) : 108 - 125