Catalytic functionalisation of fatty compounds

Catalytic Functionalisation of Fatty Compounds

Arno Behr

Chair of Technical Chemistry A, Technical University Dortmund,
Emil-Figge Str. 66, D-44227 Dortmund, Germany

Every year the chemical industry uses about 250 million tons of resources for the production of organic chemicals. Only 20 millions tons, that means only 8-10 %, are based on renewable re¬sources, especially on fat and oils. This contribution gives a short overview about the numerous possibilities to functionalise fatty compounds via homogeneous transition metal cataly¬sis.

Unsaturated fatty compounds contain one or more C=C-double bonds which can be easily functionalised via coordination to transition metal complexes [1]. Some important examples of these functionalisations are epoxi¬da¬tions, dihydroxylations, oxidative cleavage reactions, hydrosilylations [2-3], hydroformyla¬tions [4] and hydroaminomethylations [5]. Thus new carbon-oxygen-, carbon-silicon-, carbon-carbon- and carbon-nitrogen-bonds can be formed yielding a broad spectrum of chemical compounds with new properties and new applications. Further important examples are the rhodium-catalysed cooligomerisations [6-7] or the ruthenium-catalysed metathesis of fatty compounds with alkenes.

If fats and oils are transesterified with methanol glycerol is formed as an important by-product in oleochemistry. A great number of applications of glycerol are well known, how¬¬¬ever, the raising amounts of glycerol because of the enormous production of biodiesel can not be put into the market. Therefore new reactions are needed to transform glycerol into new products with new markets. Once again, homogeneous catalysis offers interesting possibilities [8-9]: Via catalytic oxidations glycerol acid or dihydroxyacetone can be formed. Dehydratisa¬tion yields acrolein which is further oxidised to acrylic acid. Further follow-up products of glycerol are for instance propanediols, epichlorohy¬drine, glycerol dimers or trimers, gly¬cerol carbonate, glycerol acetals or ketals. Another im¬por¬tant group of chemicals are the gly¬cerol ethers, for instance the glycerol tertiary butyl ethers [10] or the telomers of glycerol [11-14].
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References:
1. Behr, A.; Westfechtel, A.; Perez Gomes, J; Chemical Engineering and Technology, 2008, 31, 700.
2. Behr, A.; Naendrup, F.; Obst, D.; Eur. J. Lipid Sci. Technol., 2002, 104, 161.
3. Behr, A.; Naendrup, F.; Obst, D.; Adv. Synth. Catal., 2002, 344, 1142
4. Behr, A.; Obst, D.; Westfechtel, A.: Eur. J. Lipid Sci. Technol., 2005, 107, 213.
5. Behr, A. et al.; Eur. J. Lipid Sci. Technol., 2000, 102, 467
6. Behr, A.; Fängewisch, C.; J. Mol. Catal A: Chem, 2003, 197, 115
7. Behr, A.; Miao, Q.; J. Mol. Catal A: Chem, 2004, 222, 127
8. Behr, A.; Eilting, J.; Irawadi, K.; Leschinski, J.; Lindner, F.; Green Chem., 2008, 10, 13.
9. Behr, A.; Eilting, J.; Irawadi, K.; Leschinski, J.; Lindner, F.; Chemistry Today, 2008, 26, 32
10. Behr, A.; Obendorf, L.; Eng. Life Sci., 2003, 2, 185
11. Behr, A.; Urschey, M.; Adv. Synth. Catal., 2003, 345, 1242
12. Behr, A.; Leschinski, J.; Green Chem., 2009, in print
13. Behr, A.: Leschinski, J.; Awungacha, C.; Simic, S.; Knoth, T.; ChemSusChem, 2009, DOI:
10.1002/cssc.200800197
14. Behr, A.; Leschinski, J.; Prinz, A.; Stoffers, M.; Chem. Eng. Proc., submitted