Kazuyuki Hattori

Dissolution of polystyrene into p -cymene and related substances in tree leaf oils

We examined the dissolution of polystyrene into p-cymene and related substances to develop an alternative method for the recycling of expanded polystyrene. The dissolving power of p-cymene [212.0 g (100 g solvent)−1] to polystyrene at 50°C compared favorably with those of 2-p-cymenol [156.7 g (100 g solvent)−1], (R)-limonene and its structural isomers [181.7–197.1 g (100 g solvent)−1], and Abies leaf oil [84.7 g (100 g solvent)−1]. The favorable solubility of polystyrene into p-cymene can be explained by the solubility parameter. p-Cymene and polystyrene can be recovered almost quantitatively from the polystyrene solution by simple steam distillation.

Inhibitory effects of l-pipecolic acid from the edible mushroom, Sarcodon aspratus, on angiotensin I-converting enzyme

The aqueous extract of the edible mushroom Sarcodon aspratus showed inhibitory effects against angiotensin I-converting enzyme (ACE). l-Pipecolic acid (l-piperidine-2-carboxylic acid) was isolated from a hot-water extract in a 0.02% yield as an active principle. The mode of inhibition of l-pipecolic acid was found to be competitive, whereas its d-isomer showed no significant inhibitory effects against ACE, suggesting that the configuration of the carboxyl group in the molecule plays an important role in the enzyme inhibition.

Electrooxidative Cyclization of Hydroquinolyl Alcohols, Hydroquinolylamines, and Dimethyl Aminomalonates

Several hydroquinolyl alcohols and amines were electrochemically oxidized in methanol in the presence of sodium methoxide and potassium iodide to afford the corresponding intramolecular cyclization products. Furthermore, several amino malonates were electrochemically oxidized to yield the corresponding heterocyclic compounds through an intramolecular carbon–carbon bond formation in the presence of sodium cyanide in methanol.

Synthesis of oligosaccharide-branched ribofuranan by ring-opening polymerization of a new anhydroribo trisaccharide monomer.

A new anhydroribotrisaccharide monomer, A2B3LR (1), was synthesized and ROP was carried out to elucidate the polymerizability and to obtain oligosaccharide-branched polysaccharides with defined structures. The new trisaccharide monomer was found to be polymerized readily with BF(3) . OEt(2) as a catalyst at -40 degrees C to give a lactose-branched polymer. Copolymerization with ADBR gave the corresponding copolymers in good yields. After removal of protective benzyl groups, D-lactose-branched ribofuranans with free hydroxyl groups were obtained in good yields. The structure of polymers was analyzed by (1)H, 13C, and two-dimensional NMR measurements, suggesting that D-lactose-branched ribofuranans had (1 --> 5)-alpha stereoregularity.

Anodic Oxidation of Ketone Allylhydrazones into the Corresponding Azines

Abstract Several ketone allylhydrazones were electrochemically oxidized in methanol in the presence of sodium methoxide and potassium iodide to afford the corresponding azines. The electro-oxidation involves formation of a new carbon–nitrogen double bond between an allylic carbon atom and the nitrogen atom of a hydrazone to afford a conjugated system. Optimal yields were obtained when 0.5 equivalents of sodium methoxide and a catalytic amount of potassium iodide were used as the supporting electrolyte at room temperature. Presumably, the electro-oxidation involves a two-electron oxidation process where the iodide ion functions as electron carrier.

Acyclic monoterpenes in tree essential oils as a shrinking agent for waste-expanded polystyrene

We examined the dissolution of polystyrene (PS) into acyclic monoterpenes present in tree essential oils, to develop an environmentally friendly shrinking agent for waste-expanded polystyrene (EPS). The dissolving powers of geranyl acetate, geranylacetone, and geranyl formate [221.8–241.2 g PS (100 g solvent)−1] compared favorably with that of (R)-limonene [181.7 g PS (100 g solvent)−1]. Their favorable dissolving powers for PS can be explained by their flexible linear structures, which may be more accessible to the inside of bulk PS compared with cyclic monoterpenes. These acyclic monoterpenes and PS were recovered almost quantitatively by simple steam distillation of the PS solution.