Investigations on heterogeneously catalysed condensations of glycerol to cyclic acetals

被引:278
作者
Deutsch, J. [1 ]
Martin, A. [1 ]
Lieske, H. [1 ]
机构
[1] Univ Rostock, Leibniz Inst Catalysis, Brance Berlin, D-12489 Berlin, Germany
关键词
solid acids; glycerol; acetalisation; transacetalisation; cyclic acetals;
D O I
10.1016/j.jcat.2006.11.006
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The acid-catalysed condensation of glycerol, a chemical from renewable materials, with benzaldehyde, formaldehyde, acetone (acetalisation), and their dimethyl acetals (transacetalisation) to mixtures of [1,3]dioxan-5-ols and [1, 3]dioxolan-4-yl-methanols was investigated. Various solid acids were evaluated as heterogeneous catalysts for the desired glycerol conversion into these potential novel platform chemicals. [1, 3]dioxan-5-ols are of particular interest as precursors for 1, 3-propanediol derivatives. Therefore, the reported investigations were focused on the identification of reaction conditions that promote the formation of [1, 3]dioxan-5-ols and suppress the formation of [1, 3] dioxol an-4-yl -methanols. (c) 2006 Elsevier Inc. All rights reserved.
引用
收藏
页码:428 / 435
页数:8
相关论文
共 22 条
[1]   STUDIES OF CYCLIC ACETAL AND KETAL ISOMERS OF GLYCEROL [J].
AKSNES, G ;
ALBRIKTS.P ;
JUVVIK, P .
ACTA CHEMICA SCANDINAVICA, 1965, 19 (04) :920-&
[2]   Binding of tetramethylammonium to polyether side-chained aromatic hosts. Evaluation of the binding contribution from ether oxygen donors [J].
Bartoli, S ;
De Nicola, G ;
Roelens, S .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (21) :8149-8156
[3]   DEVELOPMENT AND APPLICATION OF A CONTINUOUS MICROWAVE REACTOR FOR ORGANIC-SYNTHESIS [J].
CABLEWSKI, T ;
FAUX, AF ;
STRAUSS, CR .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3408-3412
[4]   Synthesis of benzylidene-protected dihydroxyacetone [J].
Carlsen, PHJ ;
Sorbye, K ;
Ulven, T ;
Aasbo, K .
ACTA CHEMICA SCANDINAVICA, 1996, 50 (02) :185-187
[5]   Syntheses and antiviral activities of 1,3-dioxolanyl-, 1,3-oxathiolanyl- and 1,3-dithiolanylnucleosides with 2-hydroxymethyl substituents [J].
Chun, MW ;
Shin, DH ;
Moon, HR ;
Lee, JW ;
Park, H ;
Jeong, LS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (11) :1475-1480
[6]   Acylation of naphthalenes and anthracene on sulfated zirconia [J].
Deutsch, J ;
Prescott, HA ;
Müller, D ;
Kemnitz, E ;
Lieske, H .
JOURNAL OF CATALYSIS, 2005, 231 (02) :269-278
[7]   Acetylation and benzoylation of various aromatics on sulfated zirconia [J].
Deutsch, J ;
Trunschke, A ;
Müller, D ;
Quaschning, V ;
Kemnitz, E ;
Lieske, H .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 207 (01) :51-57
[8]  
Forbes DC, 1998, SYNTHESIS-STUTTGART, P879
[9]   CATIONIC PALLADIUM(II), PLATINUM(II), AND RHODIUM(I) COMPLEXES AS ACETALIZATION CATALYSTS [J].
GORLA, F ;
VENANZI, LM .
HELVETICA CHIMICA ACTA, 1990, 73 (03) :690-697
[10]   TRANSACETALATION OF TRIOLS FROM DIMETHOXYMETHANE - SELECTIVITY AND SYNTHETIC APPLICATIONS [J].
GRAS, JL ;
NOUGUIER, R ;
MCHICH, M .
TETRAHEDRON LETTERS, 1987, 28 (52) :6601-6604