Formation of aminium lactates in lactic acid fermentation. Fermentative production of 1,4‐piperazinium‐(L,L)‐dilactate and its use as a starting material for the synthesis of dilactide (Part 2)

Abstract

AbstractA fermentation process for manufacturing 1,4‐piperazinium‐(L,L)‐dilactate from renewable raw materials and a method for processing this product into L,L‐dilactide are described. Lactic acid fermentation with Lactobacillus paracasei was modified in such a way that pH control occurred by using an aqueous solution of piperazine as a correcting agent instead of sodium hydroxide solution. The production of a stoichiometrically composed piperazinium lactate was possible when the pH was 5.0. From 5.0 kg of glucose and 2.15 kg of piperazine, 6.65 kg of 1,4‐piperazinium‐(L,L)‐dilactate were formed in the fermentation process. Separation from fermentation broth, purification and concentration of the product in aqueous solutions were carried out by means of ultrafiltration, nanofiltration and electrodialysis. Total product retention by the membranes used was about 33%. The crystalline salt was obtained by vacuum evaporation. Processing of the 1,4‐piperazinium‐(L,L)‐dilactate into L,L‐dilactide was performed in a special glass reactor. A product yield of 70% was achieved. The purified product was characterized by elementary analysis, as well as solubility behaviour, polarity and spectroscopic data. An overall process consisting of the stages fermentation, purification and concentration of piperazinium dilactate as well as cyclization of the latter to dilactide is described.