Oxidative Esterification of Homologous 1,3-Propanediols
- 360 Downloads
The oxidative esterification of a homologous series of diols (1,3-propanediol,2-methyl-propanediol and 2,2-dimethyl-1,3-propanediol) with methanol has been investigated using titania-supported gold, palladium and gold–palladium catalysts using molecular oxygen. The gold–palladium catalysts showed the highest activity and 1,3-propanediol was the most reactive while the additional methyl groups decreased the reactivity. However, it is possible to achieve high selectivity to methyl 3-hydroxypropionate and 2-methyl-3-hydroxyisobutyrate by mono-oxidations.
KeywordsGold catalysis Gold palladium alloy nanoparticles Oxidative esterification Diol oxidation
This work formed part of the Glycerol Challenge and Tennants Fine Chemicals Ltd and the Technology Strategy Board are thanked for their financial support. This project is co-funded by the Technology Strategy Boards Collaborative Research and Development programme, following an open competition. The Technology Strategy Board is an executive body established by the Government to drive innovation. It promotes and invests in research, development and the exploitation of science, technology and new ideas for the benefit of business—increasing sustainable economic growth in the UK and improving quality of life. For more information visit www.innovateuk.org.
- 2.Larock RC (1999) Comprehensive organic transformations: a guide to functional group preparations, 2nd edn. Wiley–VCH, New YorkGoogle Scholar
- 3.Mulzer J (1991) Comprehensive organic synthesis. Pergamon Press, OxfordGoogle Scholar
- 8.Taarning E, Nielsen IS, Egeblad K, Madsen R, Christensen CH (2008) Chem Sus Chem 1:75Google Scholar
- 9.Kunugi Y (1969) Kogyokagakuzasshi 72:1282Google Scholar
- 10.Kunugi Y (1972) Nihonkagakukaishi 2265Google Scholar
- 12.Tagawa Y, Fujimori Y, Mori K, Sasaki Y (2001) JP 2001131122 A 20010515Google Scholar
- 13.Hong Z, Yu Y (2001) Pige Huagong 18:38Google Scholar
- 22.Yoshikazu S, Shuji E, Mariko A (1996) EP 0722929 (A1)Google Scholar
- 23.Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03, revision C.02. Gaussian Inc., WallingfordGoogle Scholar