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01.02.2009 | Ausgabe 1/2009

Cellulose 1/2009

Synthesis of the perdeuterated cellulose solvents N-methylmorpholine N-oxide (NMMO-d11 and NMMO-15N-d11), N,N-dimethylacetamide (DMAc-d9 and DMAc-15N-d9), 1-ethyl-3-methylimidazolium acetate (EMIM-OAc-d14) and 1-butyl-3-methylimidazolium acetate (BMIM-OAc-d18)

Zeitschrift:
Cellulose > Ausgabe 1/2009
Autoren:
Christian Adelwöhrer, Yuko Yoneda, Toshiyuki Takano, Fumiaki Nakatsubo, Thomas Rosenau

Abstract

The syntheses of several perdeuterated substances—some of them isotopically labeled (15N) in addition—are described, which act as direct solvents of cellulose either on their own, such as N-methylmorpholine N-oxide (NMMO), 1-butyl-3-methylimidazolium acetate (BMIM-OAc), or 1-ethyl-3-methylimidazolium acetate (EMIM-OAc), or in combination with auxiliaries, such as N,N-dimethylacetamide (DMAc—for the cellulose solvent DMAc/LiCl). NMMO-d11 (9) was obtained in an eight-step approach from non-labeled diglycolic acid (1) via diethylene glycol-d8 (4) and its bis-tosylate (5), which underwent ring closure with benzylamine to N-benzylmorpholine-d8 (6). Debenzylation, methylation and oxidation completed the synthetic sequence, which was also able to provide the 15N-labeled product (9a) by usage of 15N-benzylamine. DMAc-d9 (14) was obtained from deuterated acetic acid (10) and dimethylamine-d6–carbon dioxide complex (13) in a solvent-free gas-solid reaction with acidic alumina as the catalyst. Employing the CO2-complex of 15N-dimethylamine-d6 afforded the 15N-labeled product 15N-DMAc-d9 (14a) in a similar way. The two ionic liquids EMIM-OAc (21) and BMIM-OAc (22) were obtained from imidazole in three-step sequences starting with butylation and ethylation, respectively. The resulting 1-alkyl imidazoles were purified, and subsequently methylated according to a novel protocol using dimethylcarbonate-d6. Addition of acetic acid-d4 caused traceless degradation of the methylcarbonate anions and exchange for acetate. In all syntheses, the reaction steps were optimized with non-labeled compounds towards high yields and high reproducibility before entering the “hot runs” with deuterated and otherwise isotopically labeled material.

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