Abstract
In this work, we immobilized ionic liquid 1,1,3,3-tetramethylguanidium lactate on two solid supports, bentonite and SBA-15, by different methods. The prepared materials were used to catalyze the reaction of propylene oxide and methanol to produce propylene glycol methyl ether. 1-Methoxy-2-propanol was the predominant product. The influence of the amount of the catalyst, molar ratio of the reactants, reaction temperature and time on the yield and selectivity was studied. The two catalysts were proved to be efficient and reusable catalysts for the reaction.
Graphical Abstract
1,1,3,3-Tetramethylguanidium lactate was supported on bentonite and SBA-15, which were effective and recyclable catalysts for the synthesis of propylene glycol methyl ether from methanol and propylene oxide.
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References
Welton T (1999) Chem Rev 99:2071
Earle MJ, Seddon KR (2000) Pure Appl Chem 72:1391
Wasserscheid P, Keim W (2000) Angew Chem Int Ed 39:3773
Sheldon R (2001) Chem Commun 23:2399
Dupont J, de Souza RF, Auarez PAZ (2002) Chem Rev 102:3667
Herrenmann WA (2001) Angew Chem Int Ed 41:1290
Mehnert CP, Dispenziere NC, Cook RA (2002) Chem Commun 15:1610
Zhao D, Fei Z, Geldbach TJ, Scopelliti R, Dyson PJ (2004) J Am Chem Soc 126:15876
Gao H, Han B, Li J, Jiang T, Liu Z, Wu W, Chang Y, Zhang J (2004) Synth Commun 34:3083
Jiang T, Gao H, Han B, Zhao G, Chang Y, Wu W, Gao L, Yang G (2004) Tetrahedron Lett 45:2699
Zhu A, Jiang T, Wang D, Han B, Liu L, Huang J, Zhang J, Sun D (2005) Green Chem 7:514
Zhu A, Jiang T, Han B, Huang J, Zhang J, Ma X (2006) New J Chem 30:736
Huang J, Jiang T, Gao H, Han B, Liu Z, Wu W, Chang Y, Zhao G (2004) Angew Chem Int Ed 43:1397
Ma XM, Zhou YX, Zhang JC, Zhu AL, Jiang T, Han BX (2008) Green Chem 10:59
Wu W, Han B, Gao H, Liu Z, Jiang T, Huang J (2004) Angew Chem Int Ed 43:2415
Xie H, Duan H, Li S, Zhang S (2005) New J Chem 29:1199
European Chemical Industry Ecology and Toxicological Center Report (1982) No. 4
Woods G (1990) The ICI polyurethanes book, 2nd edn. Wiley, Chichester
Parker RE, Isaacs NS (1959) Chem Rev 59:737
European Centre for Ecotoxicology and Toxicology of Chemicals (ECETOC) (1995) The toxicology of glycol ethers and its relevance to man. Technical Report No. 64:1
Martin PA, William T, Malama C (1992) Process for the preparation of glycol ethers. US Patent 5,110,992
Smith WJ, Malherbe FC (2001) Synthesis of glycol ethers. US Patent 6,291,720B1
Liu SG, Zhang XL, Li JP, Zhao N, Wei W, Sun YH (2008) Catal Commun 9:1527
Zhang WY, Wang H, Wei W, Sun YH (2005) J Mol Catal A Chem 231:83
Zhang WY, Wang H, Li QB, Dong QN, Zhao N, Wei W, Sun YH (2005) Appl Catal A Gen 294:188
Jiang T, Zhou Y, Liang S, Liu H, Han B (2009) Green Chem 11:1000
Kawabata T, Mizugaki T, Ebitani K, Kaneda K (2003) J Am Chem Soc 125:10486
Zhao D, Huo Q, Feng J, Chmelka BF, Stucky GD (1998) J Am Chem Soc 120:6024
Acknowledgments
The authors are grateful to the financial supports from the Ministry of Science and Technology of China (2006CB202504), Chinese Academy of Sciences (KJCX2.YW.H16) and National Natural Science Foundation of China (20932002, 20733010, 20633080).
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Liang, S., Zhou, Y., Liu, H. et al. Immobilized 1,1,3,3-Tetramethylguanidine Ionic Liquids as the Catalyst for Synthesizing Propylene Glycol Methyl Ether. Catal Lett 140, 49–54 (2010). https://doi.org/10.1007/s10562-010-0426-9
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DOI: https://doi.org/10.1007/s10562-010-0426-9