Glycerol-based solvents as green reaction media in epoxidations with hydrogen peroxide catalysed by bis[3,5-bis(trifluoromethyl)-diphenyl] diselenide

被引:46
作者
Garcia-Marin, Hector [1 ]
van der Toorn, John C. [2 ]
Mayoral, Jose A. [3 ]
Garcia, Jose I. [1 ]
Arends, Isabel W. C. E. [2 ]
机构
[1] Univ Zaragoza, CSIC, Fac Ciencias, Inst Ciencia Mat Aragon,Dept Organ Chem, E-50009 Zaragoza, Spain
[2] Delft Univ Technol, Lab Biocatalysis & Organ Chem, NL-2628 BL Delft, Netherlands
[3] Univ Zaragoza, Fac Ciencias, Inst Univ Catalisis Homogenea, E-50009 Zaragoza, Spain
关键词
SOLVATOCHROMIC COMPARISON METHOD; SOLVATION ENERGY RELATIONSHIPS; FLUORINATED ALCOHOLS; OLEFIN EPOXIDATION; ENVIRONMENTAL ASSESSMENT; PI-STAR; ACTIVATION; OXIDATION; SELENOXIDE; CONVERSION;
D O I
10.1039/b913052g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A family of glycerol-based solvents, consisting of eighteen 1,3-dialkoxy-2-propanols and 1,2,3-trialkoxypropanes, both symmetrically and unsymmetrically substituted at terminal positions, has been tested as new solvents in cyclooctene epoxidation with hydrogen peroxide, using a diselenide catalyst, but also without a catalyst. A quantitative relationship between the reactivity and solvent polarity properties has been developed through statistical linear regression analyses, and the predictive ability of the resulting equation has been demonstrated.
引用
收藏
页码:1605 / 1609
页数:5
相关论文
共 41 条
[1]   LINEAR SOLVATION ENERGY RELATIONSHIPS .31. ON BEKAREK MODIFICATIONS OF THE SOLVATOCHROMIC PARAMETERS [J].
ABBOUD, JLM ;
TAFT, RW ;
KAMLET, MJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1985, (06) :815-819
[2]  
ABBOUD JLM, 1981, PROG PHYS ORG CHEM, V13, P485
[3]  
[Anonymous], 1998, Green Chemistry: Frontiers in Benign Chemical Synthesis and Process
[4]   An efficient didehydroxylation method for the biomass-derived polyols glycerol and erythritol. Mechanistic studies of a formic acid-mediated deoxygenation [J].
Arceo, Elena ;
Marsden, Peter ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL COMMUNICATIONS, 2009, (23) :3357-3359
[5]   Kinetic studies of olefin epoxidation with hydrogen peroxide in 1,1,1,3,3,3-hexafluoro-2-propanol reveal a crucial catalytic role for solvent clusters [J].
Berkessel, A ;
Adrio, JA .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (2-3) :275-280
[6]   Dramatic acceleration of olefin epoxidation in fluorinated alcohols: Activation of hydrogen peroxide by multiple H-bond networks [J].
Berkessel, Albrecht ;
Adrio, Jens A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (41) :13412-13420
[7]   Unveiling the "booster effect" of fluorinated alcohol solvents:: Aggregation-induced conformational changes and cooperatively enhanced H-bonding [J].
Berkessel, Albrecht ;
Adrio, Jens A. ;
Huettenhain, Daniel ;
Neudoerfl, Jorg M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (26) :8421-8426
[8]   ANIMAL TOXICITY OF 2,2,2-TRIFLUOROETHANOL [J].
BLAKE, DA ;
CASCORBI, HF ;
ROZMAN, RS ;
MEYER, FJ .
TOXICOLOGY AND APPLIED PHARMACOLOGY, 1969, 15 (01) :83-&
[9]  
Brink G.T., 2001, J CHEM SOC, P224
[10]   What is a green solvent?: A comprehensive framework for the environmental assessment of solvents [J].
Capello, Christian ;
Fischer, Ulrich ;
Hungerbuehler, Konrad .
GREEN CHEMISTRY, 2007, 9 (09) :927-934