Isosorbide and dimethyl carbonate: a green match

被引：59
作者：
Arico, Fabio [1 ]
Tundo, Pietro [1 ]
机构：
[1] Ca Foscari Univ, Dept Environm Sci Informat & Stat, Sci Campus Via Torino 155, I-30170 Venice, Italy
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 12卷
关键词：
carbohydrate chemistry; D-sorbitol; dimethyl carbonate; green chemistry; isosorbide; LIQUID-PHASE DEHYDRATION; RENEWABLE RESOURCES; N-CARBONYLATION; SORBITOL; ACID; CONVERSION; CELLULOSE; POLYMERS; COPOLYCARBONATES; POLYCARBONATES;
D O I：
10.3762/bjoc.12.218
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this review the reactivity of the bio-based platform compounds D-sorbitol and isosorbide with green reagents and solvent dimethyl carbonate (DMC) is reported. Dehydration of D-sorbitol via DMC in the presence of catalytic amounts of base is an efficient and viable process for the preparation of the industrially relevant anhydro sugar isosorbide. This procedure is "chlorine-free", one-pot, environmental friendly and high yielding. The reactivity of isosorbide with DMC is equally interesting as it can lead to the formation of dicarboxymethyl isosorbide, a potential monomer for isosorbide-based polycarbonate, and dimethyl isosorbide, a high boiling green solvent. The peculiar reactivity of isosorbide and the non-toxic properties of DMC represent indeed a green match leading to several industrial appealing potential applications.
引用
收藏
页码：2256 / 2266
页数：11
相关论文
共 89 条
[1]   Liquid-phase dehydration of sorbitol to isosorbide using sulfated titania as a solid acid catalyst [J].
Ahmed, Imteaz ;
Khan, Nazmul Abedin ;
Mishra, Dinesh Kumar ;
Lee, Ji Sun ;
Hwang, Jin-Soo ;
Jhung, Sung Hwa .
CHEMICAL ENGINEERING SCIENCE, 2013, 93 :91-95
[2]  
Andrews M. A., 2004, Process for the manufacture of anhydro sugar alcohols with the assistance of a gas purge, Patent No. [US6,689,892B2, 6689892]
[3]   Synthesis of five- and six-membered heterocycles by dimethyl carbonate with catalytic amounts of nitrogen bicyclic bases [J].
Arico, F. ;
Evaristo, S. ;
Tundo, P. .
GREEN CHEMISTRY, 2015, 17 (02) :1176-1185
[4]   Dimethylcarbonate: a modern green reagent and solvent [J].
Arico, F. ;
Tundo, P. .
RUSSIAN CHEMICAL REVIEWS, 2010, 79 (06) :479-489
[5]  
Arico F., 2014, ScienceOpen Research, P1
[6]   Chemical Behavior and Reaction Kinetics of Sulfur and Nitrogen Half-Mustard and Iprit Carbonate Analogues [J].
Arico, Fabio ;
Evaristo, Serena ;
Tundo, Pietro .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (10) :1319-1325
[7]   Synthesis of Five-Membered Cyclic Ethers by Reaction of 1,4-Diols with Dimethyl Carbonate [J].
Arico, Fabio ;
Tundo, Pietro ;
Maranzana, Andrea ;
Tonachini, Glauco .
CHEMSUSCHEM, 2012, 5 (08) :1578-1586
[8]   Sulfur and Nitrogen Mustard Carbonate Analogues [J].
Arico, Fabio ;
Chiurato, Matteo ;
Peltier, Josephine ;
Tundo, Pietro .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (17) :3223-3228
[9]   Characterization of cyclic and non-cyclic poly-(ether-urethane)s bio-based sugar diols by a combination of MALDI-TOF and NMR [J].
Beldi, M. ;
Medimagh, R. ;
Chatti, S. ;
Marque, S. ;
Prim, D. ;
Loupy, A. ;
Delolme, F. .
EUROPEAN POLYMER JOURNAL, 2007, 43 (08) :3415-3433
[10]   Ionic liquid-phase asymmetric catalytic hydrogenation: hydrogen concentration effects on enantioselectivity [J].
Berger, A ;
de Souza, RF ;
Delgado, MR ;
Dupont, J .
TETRAHEDRON-ASYMMETRY, 2001, 12 (13) :1825-1828
123456789