Catalytic Activities of Dialkyltin Compounds Containing Silicon to the Condensation Reaction of Acetal(Ketal)-Alcohol

doi:10.3724/SP.J.1095.2013.20211

Chinese Journal of Applied Chemistry

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Catalytic Activities of Dialkyltin Compounds Containing Silicon to the Condensation Reaction of Acetal(Ketal)-Alcohol

LIN Sen^*, GUO Yangyang, DENG Ruihong, HUANG Zhiqiang

(Department of Chemistry,Nanchang University,Nanchang 330031,China)

Received:2012-05-22 Revised:2012-07-20 Published:2013-03-10 Online:2013-03-10

Abstract

Abstract: The catalytic activities of ten dialkyltin compounds containing silicon were investigated through the condensation reaction of acetal(ketal)-alcohol. Factors such as amount of catalyst, reaction time, molar ratio of aldehyde(ketone) to alcohol and solvent kind were studied toward the yield of reaction. The results show that, except one catalyst, nine compounds are good in catalytic activities for the acetalization and ketalization. The yield reached 92% and 86% under optimal compounds: catalyst dosage was 1.4% based on the mass of the reactants, the molar ratio of the aldehyde to goycol was 1∶1.3, ketone to goycol was 1∶1.9, cyclohexane was used as the water carrying agent, and the reaction was refluxed for 3 h.

Key words: dialkyltin containing silicon, catalytic activity, acetalization, ketalization

CLC Number:

O627.4

LIN Sen*, GUO Yangyang, DENG Ruihong, HUANG Zhiqiang. Catalytic Activities of Dialkyltin Compounds Containing Silicon to the Condensation Reaction of Acetal(Ketal)-Alcohol[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2013.20211.

References

[1] Maki T, Iikawa S, Mogami G, et al. Efficient Oxidation of 1,2-Diols into α- Hydroxyketones Catalyzed by Organotin Compounds [J]. Chem Eur J, 2009, 15: 5364 - 5370 .
[2] Zhenhuan Li, Kunmei Su b, Bowen Cheng, et al. Promotion of organotin modi?ed SBA-15 in the selective carboxylation of BPA with DMC [J]. Catalysis Communications, 2011, (12):932–935.
[3] Blanka Kasna, Libor Dostal, Ivana Cisarova, et al. Structure and Catalytic Activity in Alcohol Acetylation [J]. Organometallics, 2007, 26, 4080-4082.
[4] Patai S, Rappoport Z. The Chemistry of Organic Silicon Compounds [M]. New York: John Wiley& Sons, Inc,1989 .
[5] Marcel Gielen, Alwyn Davies, Keith Pannell et al. Tin Chemistry: Fundamentals, Frontiers, and Applications [M]. John Wiley & Sons, Ltd., 2008
[6] Muhammad A, Mahboob A, Salma S, et al. Synthesis and structure elucidation of new series of organotin(IV) esters with bio-screening activity and catalytic study. Inorg Chem Commun [J], 2011, 14:5-12.
[7] WANG Hongshe, YANG Jiankui, QIN Haicuo. Study on Synthetic M ethod of Acetal and Ketal Perfume [J]. Guangxi Chem Ind,2000, 29(4):27-30(in Chinese).
王宏舍,杨建奎,覃海错. 缩醛(酮)类香料的合成方法研究[J]. 广西化工, 2000, 29(4):27-30.
[8] Bejoy Thomas, Vasanthakumar Ganga Ramu, Sanjay Gopinath, et al. Catalytic acetalization of carbonyl compounds over cation (Ce3+,Fe3+ and Al3+)exchanged montmorillonites and Ce3+-exchanged Y zeolites [J]. Applied Clay Science,2011, (53): 227–235.
[9] HE Xiaoli, LIN Sen, GUO Xuan, et al. Synthesis and Catalytic Properties of Tetraorganodistannoxanes Containing Silicon [J]. Chinese J Appl Chem, 2007, 24(11):1268-1272(in Chinese).
何小立, 林森, 郭璇, 陆路德, 汪信, 杨绪杰. 含硅四烃基而锡氧烷的合成及其催化性能[J]. 应用化学, 2007, 24(11):1268-1272.
[10] LIN Sen, GUO Xuan, WANG Guoyong, et al. Study on catalytic synthesis of esterification by organotin compounds containing silicon [J]. Chem Reag, 2006, 28(6):351-353(in Chinese).
林森, 郭璇, 王国永, 等. 含硅有机锡化合物在酯化反应中的催化性能研究[J]. 化学试剂, 2006, 2(6):351-353.
[11] LIN Sen, DENG Ruihong, LU Zhiqiang, et al. Synthesis and Characterization of Bis[(trimethylsilyl)methyl]tin Arylcarboxylates [J]. Chinese J Org Chem, 2005, 25(10):1298-1301(in Chinese).
林森, 邓瑞红, 卢志强,等. 二(三甲硅亚甲基)锡二芳香羧酸酯的合成和结构表征[J].有机化学,2005, 25(10):1298-1301.
[12] LIN Sen, FU Zhifei, HE Xiaoli, et al. Synthesis, Structure and ANtitumour Activity of Phenyl-(trimethylsilylmethyl) tin Arylcarboxylates [J]. Chinese J Org Chem, 2006, 26(6): 856-859(in Chinese).
林森,付志飞,何小立, 等. 苯基(三甲基硅基亚甲基)锡化合物二芳香羧酸酯的合成、结构和抗癌活性[J], 2006, 26(6):856-859.
[13] AN De_lei, PENG Zhi hong, ORITA A, et al. Organotin perfluorooctanesulfonates as air stable lewis acid catalysts: synthesis, characterization, and catalysis [J]. Chem Eur J, 2006, 12(6): 1642-1647.

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Catalytic Activities of Dialkyltin Compounds Containing Silicon to the Condensation Reaction of Acetal(Ketal)-Alcohol

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