Preparation of high purity 1,2-diols by catalytic oxidation of linear terminal alkenes with H2O2 in the presence of carboxylic acids under solvent-free conditions
-
关键词:
- 1,2-Diol
- / Oxidation
- / Terminal alkenes
- / Raman
- / FT-IR
English
Preparation of high purity 1,2-diols by catalytic oxidation of linear terminal alkenes with H2O2 in the presence of carboxylic acids under solvent-free conditions
-
Key words:
- 1,2-Diol
- / Oxidation
- / Terminal alkenes
- / Raman
- / FT-IR
-
-
[1] B.S. Lane, K. Burgess, Metal-catalyzed epoxidations of alkenes with hydrogen peroxide, Chem. Rev. 7 (2003) 2457-2473.[1] B.S. Lane, K. Burgess, Metal-catalyzed epoxidations of alkenes with hydrogen peroxide, Chem. Rev. 7 (2003) 2457-2473.
-
[2] G. Grigoropoutou, J.H. Clark, J.A. Elings, Recent developments on the epoxidation of alkenes using hydrogen peroxide as an oxidant, Green Chem. 5 (2003) 1-7.[2] G. Grigoropoutou, J.H. Clark, J.A. Elings, Recent developments on the epoxidation of alkenes using hydrogen peroxide as an oxidant, Green Chem. 5 (2003) 1-7.
-
[3] D.C. Duncan, R.C. Chambers, E. Hecht, C.L. Hill, Mechanism and dynamics in the H3[PW12O40]-catalyzed selective epoxidation of terminal olefins by H2O2: formation, reactivity, and stability of {PO4][WO(O2)2]4}3, J. Am. Chem. Soc. 117 (1995) 681-691.[3] D.C. Duncan, R.C. Chambers, E. Hecht, C.L. Hill, Mechanism and dynamics in the H3[PW12O40]-catalyzed selective epoxidation of terminal olefins by H2O2: formation, reactivity, and stability of {PO4][WO(O2)2]4}3, J. Am. Chem. Soc. 117 (1995) 681-691.
-
[4] D. Yong, B.C. Ma, D.J. Tong, et al., Synthesis of epoxides catalyzed by a halide-free reaction-controlled phase-transfer catalytic system: [(CH3(CH2)17)2N(CH3)2]3[PW4O32]/H2O2/dioxan/olefin, Aust. J. Chem. 62 (2009) 739-746.[4] D. Yong, B.C. Ma, D.J. Tong, et al., Synthesis of epoxides catalyzed by a halide-free reaction-controlled phase-transfer catalytic system: [(CH3(CH2)17)2N(CH3)2]3[PW4O32]/H2O2/dioxan/olefin, Aust. J. Chem. 62 (2009) 739-746.
-
[5] R. Neumann, H. Miller, Alkene oxidation in water using hydrophobic silica particles derivatized with polyoxometalates as catalysts, J. Chem. Soc. Chem. Commun. (1995) 2277-2278.[5] R. Neumann, H. Miller, Alkene oxidation in water using hydrophobic silica particles derivatized with polyoxometalates as catalysts, J. Chem. Soc. Chem. Commun. (1995) 2277-2278.
-
[6] R. Neumann, M. Cohen, Solvent-anchored supported liquid phase catalysis: polyoxo-metalate-catalyzed oxidations, Angew. Chem. Int. Engl. 36 (1997) 1738-1740.[6] R. Neumann, M. Cohen, Solvent-anchored supported liquid phase catalysis: polyoxo-metalate-catalyzed oxidations, Angew. Chem. Int. Engl. 36 (1997) 1738-1740.
-
[7] T. Sakamoto, C. Pac, Selective epoxidation of olefins by hydrogen peroxide in water using a polyoxometalate catalyst supported on chemically modified hydrophobic mesoporous silica gel, Tetrahedron Lett. 41 (2000) 10009-10012.[7] T. Sakamoto, C. Pac, Selective epoxidation of olefins by hydrogen peroxide in water using a polyoxometalate catalyst supported on chemically modified hydrophobic mesoporous silica gel, Tetrahedron Lett. 41 (2000) 10009-10012.
-
[8] D. Yong, B.C. Ma, Q. Gao, J.S. Sou, Epoxidation of alkenes by hydrogen peroxide over 12-heteropolyacids of molybdenum and tungsten (H3PMo3W9O40) combined with cetylpyridinium bromide, J. Chem. Res. 2006 (2006) 499-503.[8] D. Yong, B.C. Ma, Q. Gao, J.S. Sou, Epoxidation of alkenes by hydrogen peroxide over 12-heteropolyacids of molybdenum and tungsten (H3PMo3W9O40) combined with cetylpyridinium bromide, J. Chem. Res. 2006 (2006) 499-503.
-
[9] L. Hua, Y.X. Qiao, H. Li, et al., Epoxidation of olefins with hydrogen peroxide catalyzed by a reusable lacunary-type phosphotungstate catalyst, Sci. China Chem. 54 (2011) 769-773.[9] L. Hua, Y.X. Qiao, H. Li, et al., Epoxidation of olefins with hydrogen peroxide catalyzed by a reusable lacunary-type phosphotungstate catalyst, Sci. China Chem. 54 (2011) 769-773.
-
[10] J. Chen, X. Chang, J.C. Jiang, et al., The research progress of the heteropoly acid quaternary ammonium salt phase transfer catalyst system, Guangzhou Chem. Ind. 40 (2012) 6-8.[10] J. Chen, X. Chang, J.C. Jiang, et al., The research progress of the heteropoly acid quaternary ammonium salt phase transfer catalyst system, Guangzhou Chem. Ind. 40 (2012) 6-8.
-
[11] J. Li, S. Gao, Z.W. Xi, Progress in reaction-controlled phase-transfer catalysis, Chin. J. Catal. 26 (2010) 895-911.[11] J. Li, S. Gao, Z.W. Xi, Progress in reaction-controlled phase-transfer catalysis, Chin. J. Catal. 26 (2010) 895-911.
-
[12] W.J. Xu, L. Jing, F.M. Zhang, et al., Research progress in phase-transfer catalysis by organic heteropolyacid salts, J. Zhejiang Normal Univ. 35 (2012) 85-92.[12] W.J. Xu, L. Jing, F.M. Zhang, et al., Research progress in phase-transfer catalysis by organic heteropolyacid salts, J. Zhejiang Normal Univ. 35 (2012) 85-92.
-
[13] Z.W. Xi, N. Zhou, Y. Sun, K. Li, Reaction-controlled phase-transfer catalysis for propylene epoxidation to propylene oxide, Science 292 (2001) 1139-1141.[13] Z.W. Xi, N. Zhou, Y. Sun, K. Li, Reaction-controlled phase-transfer catalysis for propylene epoxidation to propylene oxide, Science 292 (2001) 1139-1141.
-
[14] Y.Y. Chen, J.Q. Zhuang, X.M. Liu, et al., On the nature of reaction-controlled phase transfer catalysts for epoxidation of olefin: a 31P NMR investigation, Catal. Lett. 93 (2004) 41-46.[14] Y.Y. Chen, J.Q. Zhuang, X.M. Liu, et al., On the nature of reaction-controlled phase transfer catalysts for epoxidation of olefin: a 31P NMR investigation, Catal. Lett. 93 (2004) 41-46.
-
[15] H. Hua, B.C. Ma, D.J. Tong, et al., [π-C5H5N(CH2)15CH3]3[PMoW3O24]: a heteropolyoxomolybdotungstate catalyst for efficient and recyclable epoxidation of 1-octene with 30% H2O2 using environmentally friendly solvent, J. Mol. Catal. A 23 (2009) 97-105.[15] H. Hua, B.C. Ma, D.J. Tong, et al., [π-C5H5N(CH2)15CH3]3[PMoW3O24]: a heteropolyoxomolybdotungstate catalyst for efficient and recyclable epoxidation of 1-octene with 30% H2O2 using environmentally friendly solvent, J. Mol. Catal. A 23 (2009) 97-105.
-
[16] X.Y. Sun, X.B. Zhao, W. Du, D.H. Liu, Kinetics of formic acid-autocatalyzed preparation of performic acid in aqueous phase, Chin. J. Chem. Eng. 19 (2011) 964-971.[16] X.Y. Sun, X.B. Zhao, W. Du, D.H. Liu, Kinetics of formic acid-autocatalyzed preparation of performic acid in aqueous phase, Chin. J. Chem. Eng. 19 (2011) 964-971.
-
[17] G.D. Sala, A. Lattanzi, T. Severino, A. Scettri, The first application of titanocenes in the asymmetric oxidation of sulfides, J. Mol. Catal. A. 170 (2001) 219-224.[17] G.D. Sala, A. Lattanzi, T. Severino, A. Scettri, The first application of titanocenes in the asymmetric oxidation of sulfides, J. Mol. Catal. A. 170 (2001) 219-224.
-
[18] G.D. Yadav, A.A. Pujari, Epoxidation of styrene to styrene oxide: synergism of heteropoly acid and phase-transfer catalyst under Ishii-Venturello mechanism, Org. Proc. Res. Dev. 4 (2000) 88-93.[18] G.D. Yadav, A.A. Pujari, Epoxidation of styrene to styrene oxide: synergism of heteropoly acid and phase-transfer catalyst under Ishii-Venturello mechanism, Org. Proc. Res. Dev. 4 (2000) 88-93.
-
[19] J. Gao, Y. Chen, Z. Xi, et al., A spectroscopic study on the reaction-controlled phase transfer catalyst in the epoxidation of cyclohexene, J. Mol. Catal. A: Chem. 210 (2004) 197-204.[19] J. Gao, Y. Chen, Z. Xi, et al., A spectroscopic study on the reaction-controlled phase transfer catalyst in the epoxidation of cyclohexene, J. Mol. Catal. A: Chem. 210 (2004) 197-204.
-
[20] C. Rocchiccioli-Deltchef, R. Thouvent, Metal complexes of heteropolyanions α-XM11O39n- with X = Si(IV) or P(V) and M = Mo(VI) or W(VI): study of structural modifications of ligand by infrared and Raman spectrometry, J. Chem. Res. (S) (1977) 46-47.[20] C. Rocchiccioli-Deltchef, R. Thouvent, Metal complexes of heteropolyanions α-XM11O39n- with X = Si(IV) or P(V) and M = Mo(VI) or W(VI): study of structural modifications of ligand by infrared and Raman spectrometry, J. Chem. Res. (S) (1977) 46-47.
-
[21] H. Chen, W.L. Dai, X.L. Yang, et al., Studies on the structural change of a reactioncontrolled phase-transfer [π-C5H5NC16H33]3{PO4][WO3]4} catalyst during the selective oxidation of cyclopentene to glutaric acid with aqueous H2O2, Appl. Catal. A: Gen. 309 (2006) 62-69.[21] H. Chen, W.L. Dai, X.L. Yang, et al., Studies on the structural change of a reactioncontrolled phase-transfer [π-C5H5NC16H33]3{PO4][WO3]4} catalyst during the selective oxidation of cyclopentene to glutaric acid with aqueous H2O2, Appl. Catal. A: Gen. 309 (2006) 62-69.
-
[22] L. Salles, C. Aubry, J.M. Bregeauh, et al., Preparation of various onium tetrakis (oxodiperoxomolybdo) phosphates. Ⅲ. Structure and reactivity towards olefins under biphasic conditions, New J. Chem. 17 (1993) 367-375.[22] L. Salles, C. Aubry, J.M. Bregeauh, et al., Preparation of various onium tetrakis (oxodiperoxomolybdo) phosphates. Ⅲ. Structure and reactivity towards olefins under biphasic conditions, New J. Chem. 17 (1993) 367-375.
-
-
扫一扫看文章
计量
- PDF下载量: 0
- 文章访问数: 1328
- HTML全文浏览量: 29

下载: