Acid Catalyzed Competitive Esterification and Ketalization of Levulinic Acid with 1,2 and 1,3-Diols: The Effect of Heterogeneous and Homogeneous Catalysts

被引：22

作者：

Amarasekara, Ananda S. ^{[1
]}

Animashaun, Moriam A. ^{[1
]}

机构：

[1] Prairie View A&M Univ, Dept Chem, Prairie View, TX 77446 USA

来源：

CATALYSIS LETTERS | 2016年 / 146卷 / 09期

基金：

美国国家科学基金会;

关键词：

Levulinic acid; 1,2-Ethanediol; 1,2-Propanediol; 1,3-Propanediol; Acid-catalysis; ETHYLENE-GLYCOL; CONVERSION; LIQUEFACTION; CELLULOSE; PRODUCTS;

D O I：

10.1007/s10562-016-1812-8

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：

Condensation reactions of levulinic acid (LA) with 1,2-ethanediol (1,2-ED), 1,2-propanediol (1,2-PD), and 1,3-propanediol (1,3-PD) were studied using Amberlyst-15 as well as p-toluenesulfonic acid catalysts in benzene under Dean-Stark conditions. In Amberlyst-15 catalyzed reactions the products are ketals and ketal-esters, whereas p-toluenesulfonic acid catalyzed reactions produce esters and ketal-esters as products. In p-toluenesulfonic acid catalyzed reactions with 1,2-ED and 1,3-PD, LA monoester product is formed as the major product after 180 min in 75 and 97 % yields respectively. Unlike the previously reported acid catalyzed ketalization of ethyl levulinate with diols, combined ketalization-esterification of LA with diols is a complex process.

引用

页码：1819 / 1824

页数：6

共 50 条

[21] EXTRACTION OF BORIC-ACID WITH ALIPHATIC 1,3-DIOLS AND OTHER CHELATING-AGENTS
EGNEUS, B
UPPSTROM, L
ANALYTICA CHIMICA ACTA, 1973, 66 (02) : 211 - 229
[22] Selective Monobenzoylation of 1,2-and 1,3-Diols Catalyzed by Me2SnCl2 in Water (Organic Solvent Free) under Mild Conditions
Muramatsu, Wataru
William, Julius M.
Onomura, Osamu
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01): : 754 - 759
[23] Liquid phase esterification of acrylic acid with 1-butanol catalyzed by solid acid catalysts
Chen, X
Xu, Z
Okuhara, T
APPLIED CATALYSIS A-GENERAL, 1999, 180 (1-2) : 261 - 269
[24] ACID-CATALYZED DEHYDRATION OF 2,2-DIMETHYL AND RELATED 2,2-DISUBSTITUTED PROPANE 1,3-DIOLS .3. DEHYDRATION OF ALIPHATIC BETA-DIOLS
YVERNAUL.T
MAZET, M
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1969, (02): : 638 - &
[25] CYTOTOXIC COMPOUNDS .12. SOME 3-ARYLTHIOPROPANE-1,2-DIOLS AND 2-ARYLTHIOPROPANE-1,3-DIOLS - REARRANGEMENT OF 1,3-DIMETHANESULPHONATES TO 1,2-ISOMERS
KHAN, MS
OWEN, LN
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (08): : 1442 - &
[26] CO2(CO)8-CATALYZED REACTION OF CYCLIC ORTHO ESTERS WITH A HYDROSILANE AND CARBON-MONOXIDE - NOVEL METHOD FOR HOMOLOGATION OF 1,2-DIOLS, 1,3-DIOLS, AND 1,4-DIOLS
CHATANI, N
KAJIKAWA, Y
NISHIMURA, H
MURAI, S
ORGANOMETALLICS, 1991, 10 (01) : 21 - 23
[27] Hydrogenation of Cyclic 1,3-Diones to Their 1,3-Diols Using Heterogeneous Catalysts: Toward a Facile, Robust, Scalable, and Potentially Bio-Based Route
van Slagmaat, Christian A. M. R.
Verzijl, Gerard K. M.
Quaedflieg, Peter J. L. M.
Alsters, Paul L.
De Wildeman, Stefaan M. A.
ACS OMEGA, 2021, 6 (06): : 4313 - 4328
[28] Homologation of Boronic Esters with Lithiated Epoxides for the Stereocontrolled Synthesis of 1,2- and 1,3-Diols and 1,2,4-Triols
Vedrenne, Emeline
Wallner, Olov A.
Vitale, Maxime
Schmidt, Frank
Aggarwal, Varinder K.
ORGANIC LETTERS, 2009, 11 (01) : 165 - 168
[29] Regioselective synthesis of 1,2-and 1,3-diols from ω-hydroxy allyl acetates and carbonates via Pd complexes using boric acid and trialkyl borates
Cluzeau, J
Capdevielle, P
Cossy, J
TETRAHEDRON LETTERS, 2005, 46 (40) : 6945 - 6948
[30] MALIC-ACID AS A CHIRAL SYNTHON - SYNTHESIS OF 1,2 AND 1,3 OPTICALLY-ACTIVE DIOLS
THIAM, M
SLASSI, A
CHASTRETTE, F
AMOUROUX, R
SYNTHETIC COMMUNICATIONS, 1992, 22 (01) : 83 - 95

← 1 2 3 4 5 →