Cellulose p-toluenesulfonate

K. Rahn, M. Diarrrantoglou, D. Klemm, H. Berghmans, T. Heinze, Homogeneous synthesis of cellulose p-toluenesulfonates in N,N-dimethylacetamide/IiQ solvent system. Die Angew. Makromolek. Chem. 238 (1) (1996) 143-163. 

Rahn, K., Diamantoglou, M., Klemm, D., Bergmans, H., Heinze, T., 1996, Homogmeous synthesis of cellulose p-toluenesulfonates in N,N-dimediyl acetamide/LiCl solvent system. Angew. Makromol. Chem. 238 143-163. 

A number of investigations have been made on the conversion of cellulose to the 6-thio derivative, with a view to formation of disulfide cross-links. Some of the more-useful properties of wool are believed to be due to such cross-links. p-Toluenesulfonated, acetylated cellulose reacted with thiosulfate ion to give the thiosulfonate derivative (Bunte salt), which was readily oxidized to the disulfide by oxidation with iodine, according to the following equation. 

The most frequently synthesized and used cellulose sulfonates are the p-toluenesulfonates (tosylates), methanesulfo-nates (mesylates), p-bromobenzenesulfonates (brosylates), and ttifluoromethanesulfonates (Inflates). The synthesis of sulfonates through simple esterification of the -OH groups of cellulose with the corresponding sulfonic acid chlorides or anhydride is a way to attach nucleofuge groups to... 

Using the solvent system propanol-pyridine-acetic acid-water (15 10 3 12) on cellulose powder, TLC plates gave excellent separations of the water-soluble antibiotics according to Ito et al. A ninhydrin reagent or an oxidized nitroprusside reagent was used as the identification system. Based on and color, 20 basic antibiotics were separated. For six closely related compounds, in terms of Rp, the solvent system consisting of water-saturated butanol plus 2% p-toluenesulfonic acid was successful in differentiation. 

Methyl acetate forms as an intermediate in the acetic acid synthesis from methanol and carbon monoxide and is used as a solvent for cellulose, nitrates, esters and ethers. When this ester is produced via esterification of acetic acid with methanol, generally mineral acids like sulfuric acid, hydrogen chloride and aryl sulfonic acid (such as p-toluenesulfonic acid) are used as homogenous acid catalysts, while cation exchange resin and zeolites are used as heterogeneous catalysts. The relevant literature on this subject is summarized in Chapter-1. Some important studies on esterification of acetic acid with methanol are summarized below. 

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