From Glycerine via Acetals to new Amphiphils

Caused by the increasing setting up of bio fuels from renewable materials, it’s expected that there is an additional amount of 6 million tons of glycerine in 2010 on the global market. It arises as a by-product during the transesterification of natural oils and fats [1].
The traditional glycerine working industry is not able to use such an amount. In order to ensure a future value added and a stable global market price, new glycerine based products are searched [2-4].

Aim:

Find products that competitive both price and performance, which are synthesised from glycerine [2 – 4].

Results:

The hydroformylation of olefins leads to aldehydes, which reacts with glycerine to acetals [5] (Gl. 1). Those acetals contain a hydroxyl group, which could be used for chemical derivatisation leading to new amphiphils e.g. forming acid adducts.

Reference:

[1] M. Plagliaro et al Angew. Chem., 2007, 119, 45
[2] A. Behr et al. Chem. Ing. Techn., 2007, 79, 621 – 636
[3] R. Westendorf et al., Eur. Pat. Appl., 1996, 1996:501411)
[4] EP 11560242, 23.2.2006, CAO Corp.
[5] M. Beller, U. Kragl, E. Paetzold, L. Neubert, P. Kollmorgen, 2008, DE 10 2008 009 103.0