di(n-butyl)tin glycerate | 90715-42-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 英文名称: di(n-butyl)tin glycerate
• 英文别名: di(n-butyl)tin(IV)glycerate；n-Bu2Sn(glycerol-2H)；(2,2-Dibutyl-1,3,2-dioxastannolan-4-yl)methanol；(2,2-dibutyl-1,3,2-dioxastannolan-4-yl)methanol
• CAS: 90715-42-7
• 化学式: C₁₁H₂₄O₃Sn
• 分子量: 323.02
• InChiKey: MADGUZJNKNHOBR-UHFFFAOYSA-N

物化性质

• 沸点：
  301.7±34.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 di(n-butyl)tin glycerate 以 甲苯 为溶剂， 生成 二丁基二甲氧基锡
  参考文献：
  名称：

  A study on the carboxylation of glycerol to glycerol carbonate with carbon dioxide: The role of the catalyst, solvent and reaction conditions

  摘要：

  Glycerol was reacted with CO2 (5 MPa) at 450 K in presence of Sn-catalysts (n-Bu2Sn(OMe)(2) 1, n-Bu2SnO 2 or Sn(OMe)(2) 3), using either glycerol or tetraethylene glycol dimethyl ether (tedmg) as reaction medium. 1 was much more active than 2. 1 was demonstrated to convert into n-Bu2Sn(glycerol-2H) 4 upon reaction with glycerol and elimination of MeOH. Monomeric 4 is proposed to be the active species in catalysis. It converted into a polymeric material with time with consequent reduction of its catalytic activity. Also, after the first catalytic cycle 4 was converted into an oligomeric material that did not contain glycerol. This also caused the reduction of the catalytic activity. 3 was able to uptake CO2 but was not able to promote the carboxylation of glycerol.1 and 2 also promoted the trans-esterification of dimethylcarbonate (DMC) with glycerol to afford glycerol carbonate, but at a lower rate than the direct carboxylation of glycerol. This fact seems to rule out that the carboxylation of glycerol may proceed through the preliminary formation of DMC and its subsequent trans-esterification. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2006.05.021
• 作为产物：
  描述：

  二正丁基氧化锡 、 甘油 以 甲醇 为溶剂， 以96%的产率得到di(n-butyl)tin glycerate
  参考文献：
  名称：

  Methanol assisted selective formation of 1,2-glycerol carbonate from glycerol and carbon dioxide using nBu2SnO as a catalyst

  摘要：

  Selectively 1,2-glycerol carbonate was obtained from glycerol and carbon dioxide in methanol using 1 mol% (Bu2SnO)-Bu-n (dibutyltin(IV)oxide, 1) as a catalyst. The reaction attained equilibrium in 4 h and the yield of 1,2-glycerol carbonate obtained was as high as 35%. We observed the rate of the reaction depends oil the amount of the catalyst and methanol used. During the reaction We Could trap the intermediates and identify it by C-13 NMR, IR and mass spectrum of the reaction mixture. The reaction proceeds upon activation of 1 by methanol forming dibutyltindimethoxide followed by dibutyltinglycerate which undergoes CO2 insertion to produce non-isolable 7-membered tin-glycerolcarbonato complex that finally yield glycerol carbonate. Catalyst 1 was found to be successful even with 1,2-propanediol and ethylene glycol yielding the corresponding cyclic carbonate. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2009.01.010

文献信息

• Methanol assisted selective formation of 1,2-glycerol carbonate from glycerol and carbon dioxide using nBu2SnO as a catalyst
  作者：Jimil George、Yogesh Patel、S. Muthukumaru Pillai、Pradip Munshi

  DOI：10.1016/j.molcata.2009.01.010

  日期：2009.5

  Selectively 1,2-glycerol carbonate was obtained from glycerol and carbon dioxide in methanol using 1 mol% (Bu2SnO)-Bu-n (dibutyltin(IV)oxide, 1) as a catalyst. The reaction attained equilibrium in 4 h and the yield of 1,2-glycerol carbonate obtained was as high as 35%. We observed the rate of the reaction depends oil the amount of the catalyst and methanol used. During the reaction We Could trap the intermediates and identify it by C-13 NMR, IR and mass spectrum of the reaction mixture. The reaction proceeds upon activation of 1 by methanol forming dibutyltindimethoxide followed by dibutyltinglycerate which undergoes CO2 insertion to produce non-isolable 7-membered tin-glycerolcarbonato complex that finally yield glycerol carbonate. Catalyst 1 was found to be successful even with 1,2-propanediol and ethylene glycol yielding the corresponding cyclic carbonate. (C) 2009 Elsevier B.V. All rights reserved.
• A study on the carboxylation of glycerol to glycerol carbonate with carbon dioxide: The role of the catalyst, solvent and reaction conditions
  作者：Michele Aresta、Angela Dibenedetto、Francesco Nocito、Carlo Pastore

  DOI：10.1016/j.molcata.2006.05.021

  日期：2006.9

  Glycerol was reacted with CO2 (5 MPa) at 450 K in presence of Sn-catalysts (n-Bu2Sn(OMe)(2) 1, n-Bu2SnO 2 or Sn(OMe)(2) 3), using either glycerol or tetraethylene glycol dimethyl ether (tedmg) as reaction medium. 1 was much more active than 2. 1 was demonstrated to convert into n-Bu2Sn(glycerol-2H) 4 upon reaction with glycerol and elimination of MeOH. Monomeric 4 is proposed to be the active species in catalysis. It converted into a polymeric material with time with consequent reduction of its catalytic activity. Also, after the first catalytic cycle 4 was converted into an oligomeric material that did not contain glycerol. This also caused the reduction of the catalytic activity. 3 was able to uptake CO2 but was not able to promote the carboxylation of glycerol.1 and 2 also promoted the trans-esterification of dimethylcarbonate (DMC) with glycerol to afford glycerol carbonate, but at a lower rate than the direct carboxylation of glycerol. This fact seems to rule out that the carboxylation of glycerol may proceed through the preliminary formation of DMC and its subsequent trans-esterification. (c) 2006 Elsevier B.V. All rights reserved.