Downstream processing of serinol from a glycerol-based fermentation broth and transfer to other amine containing molecules

Abstract

A possible application of glycerol, which is produced in large amounts as a by-product from the biodiesel industry, is its fermentation to serinol (2-amino-1,3-propanediol), a glycerol derivative. The downstream processing of this glycerol-based fermentation broth was investigated. The challenge of the isolation of serinol was the complex media and the solubility of the desired substance in aqueous media. In this study, the isolation of serinol was investigated by an appropriate reversible derivatization method. Serinol was isolated by protecting the amino group with diethyl ethoxymethylenemalonate directly in the aqueous phase, followed by extraction of the 2,2-bis(ethoxycarbonyl)vinyl-serinol (BECV-serinol) with ethyl acetate resulting in an isolated yield of 63%. We demonstrate the possibility of isolation of a hydroscopic amino alcohol from the fermentation broth and the comparison of the products in water as well as the cleavage of the 2,2-bis(ethoxycarbonyl)vinyl group (BECV group). The procedure can also be used for other amino group containing molecules, such as serine, glucosamine, hexylamine and amino methyl laureate.

Keywords: Amino alcohol isolation; Downstream processing; Fermentation broth; Glycerol; Protecting group; Serinol.