Sorbitol and derivs

Hexanitrosorbitol. See Sorbitol Hexanitrate under Sorbitol and Derivatives... 

See also D-Glucitol (Sorbitol) and Derivatives] Ref A. Tettamanzi 5c N. Arnaldi, AttiAccadSci-Torino 77, -271-77(1942) (An abbreviated transln is available at PicArsn Library)... 

Hexanitroinositol. See under Inositol and Derivatives in this Vol Hexanitrosorbitol. See Sorbitol Hexanitrate under Sorbitol and Derivatives... 

Conversion to acetates, trifluoroacetates (178), butyl boronates (179) trimethylsilyl derivatives, or cycHc acetals offers a means both for identifying individual compounds and for separating mixtures of polyols, chiefly by gas—Hquid chromatography (glc). Thus, sorbitol in bakery products is converted to the hexaacetate, separated, and determined by glc using a flame ionisation detector (180) aqueous solutions of sorbitol and mannitol are similarly separated and determined (181). Sorbitol may be identified by formation of its monobensylidene derivative (182) and mannitol by conversion to its hexaacetate (183). 

Polymerized Alcohols. Polyhydric alcohols (qv) such as pentaerythritol, sorbitol and glycerin can be used as the polyol component of polyethers (qv) which are used as expl and propint binders. Polyoxypropylene derivs of sorbitol have been employed extensively as components of polyurethane resins (qv), also employed as a propint binder... 

Dianhydro-n-mannitol or isomannide was first prepared many years ago by Fauconnier44 who obtained it by heating D-mannitol with hydrochloric acid. The dianhydrides of D-sorbitol and L-iditol were not prepared, however, until very recent times. Although isomannide is a crystalline substance forming well defined derivatives very little work has been carried out on it and its structure was not determined until 1945, but in that and the following years a flood of experiments having a... 

The rings in l,4 3,6-dianhydro-D-sorbitol have different stabilities. Montgomery and Wiggins66 treated the anhydride with hydrochloric acid under pressure and isolated some l,6-dichloro-l,6-didesoxy-D-sorbitol and much 6-chloro-6-desoxy-l,4-anhydro-D-sorbitol, both isolated as their benzylidene derivatives. No l-chloro-l-desoxy-3,6-anhydro-D-sorbitol was found. This experiment demonstrates that the 1,4-anhydro ring is more stable than the 3,6-ring in this substance. This is in agreement with the fact that partial dehydration of D-sorbitol in the 1,4-position can be preferentially effected and 1,4-anhydro-D-sorbitol isolated. 

The 5,6-anhydro derivatives of D-sorbitol and D-mannitol41 69 behave in like manner to the 5,6-anhydro-l,2-isopropylidene-D-glucofuranose of Freudenberg and coworkers.70 Thus, 5,6-anhydro-l,3 2,4-diethyli-dene-D-sorbitol (LXXXV) readily suffers ring scission with ammonia to give 6-amino 6-desoxy-l,3 2,4-diethylidene-D-sorbitol (LXXXVI)69 or with sodium methoxide to form 6-methyl-l,3 2,4-diethylidene-D-sorbitol.42 l,2 3,4-Diisopropylidene-5,6-anhydro-D-mannitol gives rise... 

Although the partial esters of sorbitol and D-mannitol have long been known and are the most important derivatives commercially, very little is known of their structure. With pure fatty acids now obtainable in the... 

Gas chromatography-mass spectrometry has also been used to detect sorbitol [37]. The components were converted to the trimethylsilyl derivatives and separated on a capillary column. Sorbofviranose, sorbopyranose, fructofuranose, fructopyranose, sorbitol, and 5-keto-sorbose were able to be identified in sorbose using the technique... 

Isosorbide and isomannide are important by-products of the starch industry, arising from dehydration of D-sorbitol and D-mannitol. These commercial starting materials provide an easy and inexpensive access to optically pure functionalized tetrahydrofurans like 04,05-isopropylidene-1-iodo-3,6-anhydro-1-deoxy-D-glucitol and 04,05-isopropylidene-l-iodo-3,6-anhydro-1-deoxy-Q-mannitol. This procedure describes a preparation of the former compound and the epoxide derived therefrom. 

Finally, curtain euriouw observations published recently by Vargha and Kawtremer 7 m of interest. Treatment of the I42 C,6-dianhydro-3, 0-vtapropy)jdene derivatives of o-mannitol, t>. sorbitol, and L-iditcd -with alkali unexpectedly gave the corresponding... 

Although glucose has some of the properties expected of an aldehyde, it lacks others. For example, it forms certain carbonyl derivatives (e.g., oxime and cyanohydrin), and can be reduced to the hexahydroxyhexane (sorbitol), and oxidized with bromine to gluconic acid (a monocarboxylic acid). (With nitric acid, oxidation proceeds further to give the dicarboxylic acid, D-glucaric acid.)... 

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