Serinol: a biosourced building block for better mechanical reinforcement and sustainable vulcanization of rubber compounds

Serinol and serinol derivatives were used to promote the mechanical reinforcement and the sulphur based crosslinking of rubber compounds. Reaction of serinol was performed with aldehydes and ketones, such as cinnamaldehyde, acetone, 2,5-hexanedione and camphor, obtaining the regiospecific synthesis of either imines or oxazolidines. Paal-Knorr reaction was as well carried out between serinol and 2,5-hexanedione, obtaining a serinol derivative containing a pyrrole ring, 2-(2,5-dimethyl-1H-pyrrol-1-yl)-1,3-propanediol, named as serinolpyrrole. All the reactions were performed in the absence of solvents and catalysts and were characterized by high and also quantitative yields. Thanks to the reactions’ specificity, pure substances were obtained, with controlled atoms hybridization. The aromatic pyrrole ring was exploited to form adducts of serinolpyrrole with carbon allotropes. Adducts of SP with carbon black promoted the reduction of filler networking in silica based compounds. Serinol and immine as well oxazolidine derivatives were efficient secondary accelerators in silica based compounds and are thus suitable substances for the replacement of DPG. Tuning of vulcanization kinetics was performed.