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2B
1 duo
Etherification of monosaccharide with isobutene:
A catalytic reaction towards new products.
Project Anorganische Chemie &Katalyse
Alkylation of polyhydroxyl alcohols has attracted attention as a useful way of valorization of
some bio-feedstock compounds. A recent example is etherification of glycerol and ethylene
glycol with isobutene over acidic catalysts. [1] [2] The reaction is straightforward thanks to
the facile formation of tertiary carbocation from isobutene, which subsequently reacts with the
alcohols.
O
cat.
OH +
HO
+ diethers +
O
monoethers
OH
O
In this project, a similar etherification will be attempted on monosaccharides, especially
D-glucose, due to its availability and low price. If the results are positive, the scope can be
expanded to reaction of D-glucose with 1-octene, which could give products with very
interesting properties. The reactions will be carried out in an autoclave.
RO
HO
O
HO
OH
HO
OH
+
cat.
O
RO
OR
RO
OR
R = t-butyl or H
The products, depending on the number of substituted OH groups, are expected to have
significantly different polarities. Therefore, they should be easily separated by
chromatography. Both the reaction mixture and the semi-crude or pure products can be
analyzed by HPLC and LC-MS, GC-MS. The project will focus on analytical methods and
interpretation of the results.
Literature:
1. R.S. Karinen and A.O.I. Krause 306, 7 2006, 128-133
2. Regina Palkovits, Ilenia Nieddu, Robertus J. M. Klein Gebbink, Bert M. Weckhuysen
DOI: 10.1002/cssc.200700147
Supervisor: Agnieszka Ruppert (Went Z217; tel. 030 253 7763, [email protected])