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100 Organic Chemistry and Catalysis Catalytic production of 1,3-butadiene from erythritol Suresh Raju, S.Raju@uu.nl, Phone: 06 - 26837541 Sponsor: CatchBio, since October 2010 Supervisors: Prof. dr. Robertus J. M. Klein Gebbink and dr. J.T.B.H. Jastrzebski NMR, GC, GC-MS, IR, ESI-MS, XRD Since fossil feed stocks are further depleting and increasing in price, it is essential to find an alternative source to produce energy, fuels and chemicals. Therefore renewable sources (biomass) are currently considered to be used as the feedstock towards the sustainable production of chemicals for the industries. After the pre-treatment of biomass, lignocellulosic biomass is obtained as the major component. This contains various polymeric compounds such as starch, cellulose and lignin. By breaking these polymers into smaller monomeric molecules, sugars, polyols and aromatic compounds are obtained. In particular the sugars and polyols contain many hydroxyl group functionalities and, accordingly, have a high oxygen content. In order to arrive at some of the main chemical building blocks, e.g. olefins, the challenge is to remove the hydroxyl groups. In principle, one can obtain the polyols by decarbonylation [1,2] of C and/or C sugars. Partial or 5 6 complete dehydroxylation of polyols then leads to the formation of olefins. The removal of hydroxyl groups can then be accomplished by means of dehydration [3] and deoxygenation [4] methods, or even deoxydehydration methods to arrive at olefins. Because rhenium has the tendency to attract and release oxygen atoms, rhenium oxo complexes have been considered for these types of reactions. Different ligated trioxo rhenium complexes have been reported in recent years for the conversion of polyols into their corresponding olefins [5]. Amongst those systems, we anticipate that the Cp*based catalyst [6] has the potential to be improved further through an optimization of electronic and steric ligand properties. Now we are working on the synthesis and catalytic performance of different substituted Cp-based trioxo rhenium complexes. Scheme 1: Deoxydehydration of 1-phenyl-1,2-ethanediol. [1] Sun J. and Liu H., Green chem. 13 (2011) 135. [2] Fabre L., Gallezot P. and Perrard A., J. of Catalysis 208 (2002) 247. [3] Korstanje T.J., Jastrzebski J.T.B.H. and Klein Gebbink R.J.M., ChemSusChem 3 (2010) 695. [4] Gable K. P. and Brown E., Organometallics 19 (2000) 944. [5] Ahmad I., Chapman G., and Nicholas K. M., Organometallics 30 (2011) 2810. [6] Cook G. K. and Andrews M. A., J. Am. Chem. Soc. 118 (1996) 9448.
Organic Chemistry and Catalysis Oxidative cleavage of olefins towards aldehydes and carboxylic acids Peter Spannring, P.Spannring@uu.nl, phone: 030 - 253 20 78 Sponsor: Utrecht University, since mid-May 2009 Supervisors: Prof. dr. Robertus J.M. Klein Gebbink, Prof. dr. B. M. Weckhuysen and dr. P.C.A. Bruijnincx ESI-MS, NMR, GC, FTIR Olefins can be found in nature as terpenes or unsaturated fatty acids, which are derived from vegetable oils and animal fats. Such alkenes can be oxidatively cleaved into mono-or dicarbonyls, i.e. aldehydes or carboxylic acids (Figure 1), which can be used in polymer, plasticizer, and stabilizer production. These products are also useful as intermediate building blocks for subsequent reactions. Expensive and often toxic transition-metal complexes derived from Ru,[1] W,[2] or Os[3] are known to catalyze these specific oxidative cleavages, with the help of reactive and relatively hazardous oxidants like NaIO or ozone. First-row transition-metal complexes are only known to cleave very 4 activated substrates like styrene-derivatives.[4] Permanganate may also be used for these reactions, yet it has to be used in stoichiometric amounts. Here, we present a study towards the use of more benign methods to oxidatively cleave internal double bonds. Ultimately, such procedures can be seen as green alternatives for the production of chemical building blocks from renewable vegetable oils and animal fats. Figure 1: General reaction equation of the oxidative cleavage of an alkene towards aldehydes and carboxylic acids. [1] Rup, S., Zimmermann, F., Meux, E., Schneider, M., Sindt, M. and Oget, N., Ultras. Sonoch. 16 (2009) 266. [2] Turnwald, S.E., Lorier, M.A., Wright, L.J. and Mucalo, M.R, J. Mat. Sci. Lett. 17 (1998) 1305. [3] Ley, S.V., Ramarao, C., Lee, A.L., Oostergaard, N., Smith, S.C., Shirley, I.M., Org. Lett. 5 (2003) 185 [4] Dhakshinamoorthy, A., Pitchumani, K., Tetrah. 62 (2006) 9911 101
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Debye Institute for Nanomaterials S
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Introduction This book gives an ove
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Chemical Biology and Organic Chemis
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Condensed Matter and Interfaces Ani
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Self assembly of nanocrystals into
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Condensed Matter and Interfaces Syn
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Condensed Matter and Interfaces Dev
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Condensed Matter and Interfaces Syn
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ZnO nanowire lasers Dr. (Lam)Bert v
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Chemical Biology and Organic Chemis
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Inorganic Chemistry and Catalysis I
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Highly active and stable methanol s
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Inorganic Chemistry and Catalysis R
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Inorganic Chemistry and Catalysis I
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Inorganic Chemistry and Catalysis S
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Inorganic Chemistry and Catalysis N
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Preparation of easy regenerable sor
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Inorganic Chemistry and Catalysis N
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Aliphatic olefins from fatty acids
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Inorganic Chemistry and Catalysis S
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Inorganic Chemistry and Catalysis T
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Inorganic Chemistry and Catalysis F
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Techniques Index 153
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