The biorefinery is an important approach for the current needs of energy and chemical building blocks for a diverse range of applications, that gradually may replace current dependence on fossil-fuel resources. Among other primary renewable building blocks, 5-hydroxymethylfurfural (HMF) is considered an important intermediate due to its rich chemistry and potential availability from carbohydrates such as fructose, glucose, sucrose, cellulose and inulin. In recent years, considerable efforts have been made on the transformation of carbohydrates into HMF. In this critical review we provide an overview of the effects of HMF on microorganisms and humans, HMF production and functional group transformations of HMF to relevant target molecules by taking advantage of the primary hydroxyl, aldehyde and furan functionalities.

Toxicological evaluation of a new group of ionic liquids was performed on human colon cancerous cells—CaCo-2. They belong to different classes of cations: imidazolium (IM), dimethyl-guanidinium (dmg) and tetramethyl-guanidinium (tmg), methyl-pyrrolidinium (MPyr), 2-methyl-1-ethyl-pyridinium (2-MEPy), quaternary ammonium (benzyltriethyl-ammonium–BzTEA; phenyltrimethyl-ammonium–PhTMA; tri-n-octyl-methylammonium-Aliquat) and tri-n-hexyl-tetra-n-decylphosphonium (P6,6,6,14). The new results were compared with data obtained in previous reported studies performed in our lab, and we clearly saw that toxicity can vary significantly with the type of anion. Dicyanoamide-[DCA] and bis(trifluoromethanesulfonyl)amide-[NTf₂] were seen to visibly change the impact of some cations. Some were considerably less harmful for CaCo-2 monolayer when the anion was [DCA] or [NTf₂ ], while others induced an abnormal increase of cellular metabolism when [NTf₂ ] was present and therefore, they were considered toxic. However, some cations induced similar responses in the presence of a broad number of anions as (1-butyl-3-methylimidazolium)-[C₄MIM] (with the exception of [FeCl₄ ]), (1-(2-hydroxyethyl)-3-methylimidazolium)-[C₂OHMIM] and [C₄MPyr] and did not cause toxicity. Consequently, they are considered promising cations for building human friendlier solvents. But, a reasonable number of other combinations involving different classes of cations were also seen to not significantly affect viability of the CaCo-2 monolayer.

Several specific synthetic protocols were developed for the preparation from cyanuric chloride of a range of symmetric and non-symmetric di- and tri-substituted 1,3,5-triazines containing alkyl, aromatic, hindered, chiral and achiral hydroxyalkyl, ester and imidazole groups via sequential nucleophilic substitution of the C-Cl bond by C-O, C-N and C-S bonds.

An extended study on the solubility of the carbohydrates glucose, fructose, sucrose and lactose in twenty eight different ionic liquids (ILs) was performed. These ILs were based on the combination of tetraalkylammonium, tetraalkylphosphonium, 1-methyl-3-alkylimidazolium and dimethyl-tetraalkylguanidinium cations containing alkyl and ether pendant substituent groups, and anions of chloride, dicyanamide, saccharine, acesulfame, acetate or thiocyanate. It was possible to achieve solubilities, at 35 °C, of each carbohydrate up to 43.9, 49.0, 17.1 and 16.6% (g of carbohydrate per 100 g of IL), respectively. The possibility to extract carbohydrates from an aqueous phase by hydrophobic ILs was also demonstrated. Besides, some selectivity for a mixture of two carbohydrates was also observed.