(n-Bu2Sn)2O(CO3): An active, robust and recyclable organotin(IV) for the direct synthesis of linear organic carbonates from carbon dioxide and alcohols

被引:8
作者
Sanapureddy, Sreevardhan Reddy [1 ]
Plasseraud, Laurent [1 ]
机构
[1] Univ Bourgogne Franche Comte, ICMUB, CNRS, UMR 6302, 9 Ave A Savary, F-21078 Dijon, France
关键词
alcohol conversion; carbon dioxide utilization; carbonato complex; diorganotin(IV); linear organic carbonates; DIMETHYL CARBONATE; NMR-SPECTROSCOPY; CO2; METHANOL; 2-OXAZOLIDINONES; REACTIVITY; FEEDSTOCK; CATALYSIS; CHEMICALS; SYSTEM;
D O I
10.1002/aoc.3807
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Organotin(IV) compounds are known to promote the direct synthesis of organic carbonates from carbon dioxide and alcohols. In the past, structural studies have highlighted that the carbonato moiety is a recurring ligand of tin species collected during CO2 pressurized reactions. In a mimetic approach and in order to achieve an available and recyclable precursor, the title compound (n-Bu2Sn)(2)O(CO3) (1) was prepared in a single step by reacting commercial di-n-butyltin dichloride with an aqueous solution of sodium carbonate. Compound 1 was characterized using infrared spectroscopy and thermogravimetric and elemental analyses. Multinuclear NMR investigations in solution were also conducted. Compound 1 was then evaluated for the direct carbonation of alcohols (methanol, ethanol, n-butanol and isopropanol) under CO2 pressure. Recycling experiments were performed showing the efficient reuse of 1 without loss of activity. Furthermore, the infrared fingerprint of 1 was preserved even after several runs demonstrating a good stability. The effects of pressure and of reaction time on dimethyl carbonate formation were also studied.
引用
收藏
页码:2335 / 2342
页数:8
相关论文
共 57 条
[31]   Reaction of dibutyltin oxide with methanol under CO2 pressure relevant to catalytic dimethyl carbonate synthesis [J].
Kohno, Kazufumi ;
Choi, Jun-Chul ;
Ohshima, Yoshihiro ;
Yili, Abulimiti ;
Yasuda, Hiroyuki ;
Sakakura, Toshiyasu .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (07) :1389-1392
[32]   THE STRUCTURE OF ((ISO-BU)3N)2CO3 AND (ME3SN)2CO3 IN SOLUTION AND IN THE SOLID-STATE STUDIED BY C-13/SN-119 NMR-SPECTROSCOPY AND X-RAY-DIFFRACTION [J].
KUMMERLEN, J ;
SEBALD, A ;
REUTER, H .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 427 (03) :309-323
[33]   High-pressure NMR spectroscopy: An in situ tool to study tin-catalyzed synthesis of organic carbonates from carbon dioxide and alcohols. Part 2 [1] [J].
Laurenczy, Gabor ;
Dalebrook, Andrew F. ;
Picquet, Michel ;
Plasseraud, Laurent .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2015, 796 :53-58
[34]   Di-n-butyltin(IV)-catalyzed dimethyl carbonate synthesis from carbon dioxide and methanol: An in situ high pressure 119Sn{1H} NMR spectroscopic study [J].
Laurenczy, Gabor ;
Picquet, Michel ;
Plasseraud, Laurent .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (09) :1904-1909
[35]   A novel chiral 3D supramolecular framework based on organooxotin cluster [J].
Li, Shun-Li ;
Ping, Guang-Ju ;
Liu, Jie ;
Ma, Jian-Fang ;
Su, Zhong-Min .
INORGANIC CHEMISTRY COMMUNICATIONS, 2008, 11 (02) :220-224
[36]   Using carbon dioxide as a building block in organic synthesis [J].
Liu, Qiang ;
Wu, Lipeng ;
Jackstell, Ralf ;
Beller, Matthias .
NATURE COMMUNICATIONS, 2015, 6
[37]   Reversible CO2 fixation by intramolecularly coordinated diorganotin(IV) oxides [J].
Mairychova, Barbora ;
Dostal, Libor ;
Ruzicka, Ales ;
Benes, Ludvik ;
Jambor, Roman .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 699 :1-4
[38]   Recent Advances in the Catalytic Preparation of Cyclic Organic Carbonates [J].
Martin, Carmen ;
Fiorani, Giulia ;
Kleij, Arian W. .
ACS CATALYSIS, 2015, 5 (02) :1353-1370
[39]   Tin Tetra(tert-butoxide) with Acid-Base Additives: Valid Catalyst Precursors for Direct Synthesis of Dimethyl Carbonate from CO2 and CH3OH [J].
Masui, Yoichi ;
Haga, Shunsuke ;
Onaka, Makoto .
CHEMISTRY LETTERS, 2011, 40 (12) :1408-1410
[40]   Recent developments in carbon dioxide utilization for the production of organic chemicals [J].
Omae, Iwao .
COORDINATION CHEMISTRY REVIEWS, 2012, 256 (13-14) :1384-1405