1. Field of the Invention
The present invention relates to a novel and very advantageous process for the rational synthesis of serinol on an industrial scale, as well as of serinol derivatives substituted at the nitrogen atom obtained from the process.
2. Description of the Prior Art
Serinol (1,3-dihydroxy-isopropylamine), may be synthesized by the reduction of the oxime of 1,3-dihydroxyacetone. As a result of isomerization, however, a mixture of serinol and 2,3-dihydroxy-propylamine results which is extremely difficult to separate. Serinol is therefore generally synthesized from nitromethane. For this purpose, nitromethane is reacted in an alkaline solution with formaldehyde to form 2-nitro-1,3-propanediol which is then catalytically reduced to serinol. However, undesirable side reactions may also occur in this process. In this connection, reference is made to Schmidt et al, Ber. dtch. chem. Ges., 52, 389, Langenbeck et al, Naturwissenschaften 42, (1955), 389-90; Schipper et al, J. Org. Chem. 26 (1961), 4145-8; Pfeiffer, German Auslegeschrift No. 2,742,981 (Schering A. G.).
This method requires handling the highly explosive nitromethane and the even more dangerous 2-nitro-1,3-propanediol or its sodium salt. Accidents with nitroalkanes have led to such restrictive Government regulations that aliphatic nitro compounds may now be used only in highly safeguarded, far-removed plants, whose equipment and operation is profitable only for large scale products.
As a result, it is difficult to buy serinol in sufficient amounts or to have it synthesized from nitromethane since no one was willing or permitted to take such high risks.