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Volumn 115, Issue 1, 2013, Pages 111-122

Synthesis of five and six-membered cyclic glycerilic carbonates bearing exocyclic urethane functions

Author keywords

Aminolysis; Cyclic glycerylic carbonate; Glycerol carbonate; Hydroxyurethane; Transesterification

Indexed keywords


EID: 84872423143     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.201200082     Document Type: Article
Times cited : (19)

References (38)
  • 1
    • 79959978543 scopus 로고    scopus 로고
    • Progress in study of non-isocyanate polyurethane
    • Guan, J., Song, Y., Lin, Y., Yin, X. et al., Progress in study of non-isocyanate polyurethane. Ind. Eng. Chem. Res. 2011, 50, 6517- 6527.
    • (2011) Ind. Eng. Chem. Res. , vol.50 , pp. 6517-6527
    • Guan, J.1    Song, Y.2    Lin, Y.3    Yin, X.4
  • 2
    • 0036275940 scopus 로고    scopus 로고
    • Biodegradation of polyurethane: A review
    • Howard, G. T., Biodegradation of polyurethane: A review. Int. Biodeterior. Biodegrad. 2002, 49, 245- 252.
    • (2002) Int. Biodeterior. Biodegrad. , vol.49 , pp. 245-252
    • Howard, G.T.1
  • 3
    • 84981925834 scopus 로고
    • Epoxy resins modified by carbon dioxide
    • Rokicki, G., Lazinski, R., Epoxy resins modified by carbon dioxide. Angew. Makromol. 1987, 148, 53- 66.
    • (1987) Angew. Makromol. , vol.148 , pp. 53-66
    • Rokicki, G.1    Lazinski, R.2
  • 4
    • 0027454802 scopus 로고
    • A safe and efficient method for conversion of 1,2- and 1,3- diols to cyclic carbonates utilizing triphosgene
    • Burk, R. M., Roof, M. B., A safe and efficient method for conversion of 1, 2- and 1, 3- diols to cyclic carbonates utilizing triphosgene. Tetrahedron Lett. 1993, 34, 395- 398.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 395-398
    • Burk, R.M.1    Roof, M.B.2
  • 5
    • 33847085662 scopus 로고
    • Synthesis of cyclic carbonates from carbon dioxide and epoxides in the presence of organoantimony compounds as novel catalysts
    • Nomura, R., Ninagawa, A., Matsuda, H., Synthesis of cyclic carbonates from carbon dioxide and epoxides in the presence of organoantimony compounds as novel catalysts. J. Org. Chem. 1980, 45, 3735- 3738.
    • (1980) J. Org. Chem. , vol.45 , pp. 3735-3738
    • Nomura, R.1    Ninagawa, A.2    Matsuda, H.3
  • 6
    • 0012414644 scopus 로고    scopus 로고
    • Cyclic carbonate formation from carbon dioxide and oxiranes in tetrabutylammonium halides as solvents and catalysts
    • Calo, V., Nacci, A., Monopoli, A., Fanizzi, A., Cyclic carbonate formation from carbon dioxide and oxiranes in tetrabutylammonium halides as solvents and catalysts. Org. Lett. 2002, 4, 2561- 2563.
    • (2002) Org. Lett. , vol.4 , pp. 2561-2563
    • Calo, V.1    Nacci, A.2    Monopoli, A.3    Fanizzi, A.4
  • 7
    • 84990501712 scopus 로고
    • Active sites, nature and mechanism of carbon dioxide-propylene oxide copolymerization and cyclization reactions employing organozinc-oxygen catalysts
    • Kuran, W., Active sites, nature and mechanism of carbon dioxide-propylene oxide copolymerization and cyclization reactions employing organozinc-oxygen catalysts. Appl. Organomet. Chem. 1991, 5, 191- 194.
    • (1991) Appl. Organomet. Chem. , vol.5 , pp. 191-194
    • Kuran, W.1
  • 8
    • 33646940749 scopus 로고    scopus 로고
    • Metal salen derivatives as catalysts for the alternating copolymerization of oxetanes and carbon dioxide to afford polycarbonates
    • Darensbourg, D. J., Ganguly, P., Choi, W., Metal salen derivatives as catalysts for the alternating copolymerization of oxetanes and carbon dioxide to afford polycarbonates. Inorg. Chem. 2006, 45, 3831- 3833.
    • (2006) Inorg. Chem. , vol.45 , pp. 3831-3833
    • Darensbourg, D.J.1    Ganguly, P.2    Choi, W.3
  • 9
    • 33947348684 scopus 로고
    • Studies on polymerization and ring formation. III. Glycol esters of carbonic acid
    • Carothers, W. H., Van Natta, F. J., Studies on polymerization and ring formation. III. Glycol esters of carbonic acid. J. Am. Chem. Soc. 1930, 52, 314- 318.
    • (1930) J. Am. Chem. Soc. , vol.52 , pp. 314-318
    • Carothers, W.H.1    Van Natta, F.J.2
  • 10
    • 0035281170 scopus 로고    scopus 로고
    • Structural analysis of polyhydroxyurethane obtained by polyaddition of bifunctional five-membered cyclic carbonates and diamine based on model reaction
    • Tomita, H., Sanda, F., Endo, T., Structural analysis of polyhydroxyurethane obtained by polyaddition of bifunctional five-membered cyclic carbonates and diamine based on model reaction. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 851- 859.
    • (2001) J. Polym. Sci., Part A: Polym. Chem. , vol.39 , pp. 851-859
    • Tomita, H.1    Sanda, F.2    Endo, T.3
  • 11
    • 0001230941 scopus 로고
    • The stereochemistry and mechanism of reversible polymerization of 2,2-disubstituted 1,3-propanediol carbonates
    • Sarel, S., Pohoryles, L. A., The stereochemistry and mechanism of reversible polymerization of 2, 2-disubstituted 1, 3-propanediol carbonates. J. Am. Chem. Soc. 1958, 80, 4596- 4599.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 4596-4599
    • Sarel, S.1    Pohoryles, L.A.2
  • 12
    • 0002052248 scopus 로고
    • Organic carbonates. IV. 1a, b, c factors affecting formation of homologous cyclic carbonates
    • Sarel, S., Pohoryles, L. A., Ben Shoshan, R., Organic carbonates. IV. 1a, b, c factors affecting formation of homologous cyclic carbonates. J. Org. Chem. 1959, 24, 1873- 1880.
    • (1959) J. Org. Chem. , vol.24 , pp. 1873-1880
    • Sarel, S.1    Pohoryles, L.A.2    Ben Shoshan, R.3
  • 13
    • 0026765150 scopus 로고
    • Homopolymerization of 1,8-dioxan-2-one to high molecular weight poly(trimethylene carbonate)
    • Albertson, A.-C., Sjoeling, M., Homopolymerization of 1, 8-dioxan-2-one to high molecular weight poly(trimethylene carbonate). J. Macromol. Sci. Pure Appl. Chem. 1992, 29, 43- 54.
    • (1992) J. Macromol. Sci. Pure Appl. Chem. , vol.29 , pp. 43-54
    • Albertson, A.-C.1    Sjoeling, M.2
  • 14
    • 0031998524 scopus 로고    scopus 로고
    • Synthesis of copolymer of 1,3-dioxan-2-one and 2-hydro-2-oxo-1,3,2-dioxaphosphorinane
    • Hu, B., Zhuo, R. X., Fan, C. L., Synthesis of copolymer of 1, 3-dioxan-2-one and 2-hydro-2-oxo-1, 3, 2-dioxaphosphorinane. Polym. Adv. Technol. 1998, 9, 145- 149.
    • (1998) Polym. Adv. Technol. , vol.9 , pp. 145-149
    • Hu, B.1    Zhuo, R.X.2    Fan, C.L.3
  • 15
    • 0033728748 scopus 로고    scopus 로고
    • Aliphatic cyclic carbonates and spiroorthocarbonates as monomers
    • Rokicki, G., Aliphatic cyclic carbonates and spiroorthocarbonates as monomers. Prog. Polym. Sci. 2000, 25, 259- 342.
    • (2000) Prog. Polym. Sci. , vol.25 , pp. 259-342
    • Rokicki, G.1
  • 16
    • 0032119916 scopus 로고    scopus 로고
    • Substituent effect on the anionic equilibrium polymerization of six-membered cyclic carbonates
    • Matsuo, J., Aoki, K., Sanda, F., Endo, T., Substituent effect on the anionic equilibrium polymerization of six-membered cyclic carbonates. Macromolecules 1998, 31, 4432- 4438.
    • (1998) Macromolecules , vol.31 , pp. 4432-4438
    • Matsuo, J.1    Aoki, K.2    Sanda, F.3    Endo, T.4
  • 17
    • 15944387352 scopus 로고    scopus 로고
    • Convenient preparation of fatty acid ester carbonates
    • Kenar, J. A., Tevis, I. D., Convenient preparation of fatty acid ester carbonates. Eur. J. Lipd Sci. Technol. 2005, 107, 135- 137.
    • (2005) Eur. J. Lipd Sci. Technol. , vol.107 , pp. 135-137
    • Kenar, J.A.1    Tevis, I.D.2
  • 18
    • 0041968483 scopus 로고    scopus 로고
    • Enzymatic synthesis and polymerization of cyclic trimethylene carbonate monomer with/without methyl substituent
    • Tasaki, H., Toshima, K., Matsumara, S., Enzymatic synthesis and polymerization of cyclic trimethylene carbonate monomer with/without methyl substituent. Macromol. Biosci. 2003, 3, 436- 441.
    • (2003) Macromol. Biosci. , vol.3 , pp. 436-441
    • Tasaki, H.1    Toshima, K.2    Matsumara, S.3
  • 19
    • 79953817469 scopus 로고    scopus 로고
    • Solvent-free lipase-mediated synthesis of six-membered cyclic carbonates from trimethylolpropane and dialkyl carbonates
    • Pyo, S.-H., Persson, P., Lundmark, S., Hatti-Kaul, R., Solvent-free lipase-mediated synthesis of six-membered cyclic carbonates from trimethylolpropane and dialkyl carbonates. Green Chem. 2011, 13, 976- 982.
    • (2011) Green Chem. , vol.13 , pp. 976-982
    • Pyo, S.-H.1    Persson, P.2    Lundmark, S.3    Hatti-Kaul, R.4
  • 21
    • 84872402667 scopus 로고
    • Cyclic carbonic acids and derivatives, US Patent 4, 501, 905
    • Krimm, H., Buysh, H. J., Cyclic carbonic acids and derivatives, US Patent 4, 501, 905, 1983.
    • (1983)
    • Krimm, H.1    Buysh, H.J.2
  • 22
    • 84872378464 scopus 로고
    • Preparation of cyclic carbonate, Mitsui Petrochemical industries Ind., US Patent 0 300, 794
    • Kiso, Y. M., Preparation of cyclic carbonate, Mitsui Petrochemical industries Ind., US Patent 0 300, 794, 1988.
    • (1988)
    • Kiso, Y.M.1
  • 23
    • 84872374818 scopus 로고    scopus 로고
    • 6-membered cyclic carbonates, US Patent 03 089, 424
    • Clements, J. H., 6-membered cyclic carbonates, US Patent 03 089, 424, 2003.
    • (2003)
    • Clements, J.H.1
  • 24
    • 84872417742 scopus 로고    scopus 로고
    • Process for the preparation of cyclic carbonates having 6-membered, US Patent 5 861, 107
    • Buysh, H.-J., Process for the preparation of cyclic carbonates having 6-membered, US Patent 5 861, 107, 1997.
    • (1997)
    • Buysh, H.-J.1
  • 26
    • 38549149213 scopus 로고    scopus 로고
    • Chemoselective catalytic conversion of glycerol as a biorenewable source to valuable commodity chemicals
    • Zhou, C.-H., Beltramini, J. N., Fan, Y.-X., Lu, G. Q., Chemoselective catalytic conversion of glycerol as a biorenewable source to valuable commodity chemicals. Chem. Soc. Rev. 2008, 37, 527- 549.
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 527-549
    • Zhou, C.-H.1    Beltramini, J.N.2    Fan, Y.-X.3    Lu, G.Q.4
  • 27
    • 0037449650 scopus 로고    scopus 로고
    • Synthesis and characterization of glycerol dimethacrylate cross-linked polymethyl methacrylate: A resin for solid phase peptide synthesis
    • Roice, M., Subhashchandran, K. P., Gean, A. V., Franklin, J., Rajasekharan Pillai, V. N., Synthesis and characterization of glycerol dimethacrylate cross-linked polymethyl methacrylate: A resin for solid phase peptide synthesis. Polymer 2003, 44, 911- 922.
    • (2003) Polymer , vol.44 , pp. 911-922
    • Roice, M.1    Subhashchandran, K.P.2    Gean, A.V.3    Franklin, J.4    Rajasekharan Pillai, V.N.5
  • 28
    • 0035056933 scopus 로고    scopus 로고
    • Conversion of glycerol to 1,3-propanediol by a newly isolated thermophilic strain
    • Wittlich, P., Themann, A., Vorlop, K. D., Conversion of glycerol to 1, 3-propanediol by a newly isolated thermophilic strain. Biotechnol. Lett. 2001, 23, 463- 466.
    • (2001) Biotechnol. Lett. , vol.23 , pp. 463-466
    • Wittlich, P.1    Themann, A.2    Vorlop, K.D.3
  • 29
    • 0037040317 scopus 로고    scopus 로고
    • Selective etherification of glycerol to polyglycerols over impregnated basic MCM-41 type mesoporous catalysts
    • Clacens, J. M., Pouilloux, Y., Barrault, J., Selective etherification of glycerol to polyglycerols over impregnated basic MCM-41 type mesoporous catalysts. Appl. Catal., A: Gen. 2000, 227, 181- 190.
    • (2000) Appl. Catal., A: Gen. , vol.227 , pp. 181-190
    • Clacens, J.M.1    Pouilloux, Y.2    Barrault, J.3
  • 31
    • 60549093615 scopus 로고    scopus 로고
    • Amphiphilic branched polymers as antimicrobial agents
    • Pasquier, N., Keul, H., Heine, E., Moeller, M. et al., Amphiphilic branched polymers as antimicrobial agents. Macromol. Biosci. 2008, 8, 903- 915.
    • (2008) Macromol. Biosci. , vol.8 , pp. 903-915
    • Pasquier, N.1    Keul, H.2    Heine, E.3    Moeller, M.4
  • 32
    • 4544231371 scopus 로고    scopus 로고
    • Polyurethanes with pendant hydroxyl groups: Synthesis and characterization
    • Ubaghs, L., Fricke, N., Keul, H., Hocker, H., Polyurethanes with pendant hydroxyl groups: Synthesis and characterization. H. Macromol. Rapid Commun. 2004, 25, 517- 521.
    • (2004) H. Macromol. Rapid Commun. , vol.25 , pp. 517-521
    • Ubaghs, L.1    Fricke, N.2    Keul, H.3    Hocker, H.4
  • 33
    • 84872401286 scopus 로고    scopus 로고
    • Process for the preparation of polyhydroxy-urethanes. FR Patent, 2, 911, 878
    • Bernard, J. M., Process for the preparation of polyhydroxy-urethanes. FR Patent, 2, 911, 878, 2008.
    • (2008)
    • Bernard, J.M.1
  • 34
    • 84861691404 scopus 로고    scopus 로고
    • Aminolysis reaction of glycerol carbonate in organic and hydroorganic medium
    • Nohra, B., Candy, L., Blanco, J. F., Raoul, Y., Mouloungui, Z., Aminolysis reaction of glycerol carbonate in organic and hydroorganic medium. J Am Oil Chem Soc 2012, 89, 1125- 1133.
    • (2012) J Am Oil Chem Soc , vol.89 , pp. 1125-1133
    • Nohra, B.1    Candy, L.2    Blanco, J.F.3    Raoul, Y.4    Mouloungui, Z.5
  • 35
    • 0035154237 scopus 로고    scopus 로고
    • Reactivity comparison of five- and six-membered cyclic carbonates with amine
    • Tomita, H., Sanda, F., Endo, T., Reactivity comparison of five- and six-membered cyclic carbonates with amine. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 162- 168.
    • (2001) J. Polym. Sci., Part A: Polym. Chem. , vol.39 , pp. 162-168
    • Tomita, H.1    Sanda, F.2    Endo, T.3
  • 36
    • 79959717484 scopus 로고    scopus 로고
    • CaO-catalyzed synthesis of glycerol carbonate from glycerol and dimethyl carbonate: Isolation and characterization of an active Ca species
    • Simanjuntak, F. S., Kim, T. K., Lee, T., Ahn, B. S. et al., CaO-catalyzed synthesis of glycerol carbonate from glycerol and dimethyl carbonate: Isolation and characterization of an active Ca species. Appl. Catal., A: Gen. 2011, 401, 220- 225.
    • (2011) Appl. Catal., A: Gen. , vol.401 , pp. 220-225
    • Simanjuntak, F.S.1    Kim, T.K.2    Lee, T.3    Ahn, B.S.4
  • 37
    • 69049113893 scopus 로고    scopus 로고
    • Synthesis of glycerol carbonate from glycerol and dimethyl carbonate by transesterification: Catalyst screening and reaction optimization
    • Ochoa-Gomez, J. R., Gomez-Jimenez-Aberasturi, O., Maestro-Madurga, B., Pesquera-Rodriguez, A. et al., Synthesis of glycerol carbonate from glycerol and dimethyl carbonate by transesterification: Catalyst screening and reaction optimization. Appl. Catal., A: Gen. 2009, 366, 315- 324.
    • (2009) Appl. Catal., A: Gen. , vol.366 , pp. 315-324
    • Ochoa-Gomez, J.R.1    Gomez-Jimenez-Aberasturi, O.2    Maestro-Madurga, B.3    Pesquera-Rodriguez, A.4
  • 38
    • 78650317028 scopus 로고    scopus 로고
    • Synthesis, characterization, and application of a bifunctional coupler containing a five- and six-membered ring carbonate
    • He, Y., Keul, H., Moller, M., Synthesis, characterization, and application of a bifunctional coupler containing a five- and six-membered ring carbonate. React. Funct. Polym. 2011, 71, 175- 186.
    • (2011) React. Funct. Polym. , vol.71 , pp. 175-186
    • He, Y.1    Keul, H.2    Moller, M.3


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