Sorbitol derivatives

VI) was hydrogenated to the corresponding sorbitol derivative (VII) in which the only groups unsubstituted were those situated at Cl and C4. Acid-catalyzed ring closure gave a product identical with the tetramethyl derivative of arlitan. 

The acetates of the l,4 3,6-dianhydrohexitols may also be useful as plasticizers both 2,5-diacetyl-l,4 3,6-dianhydro-D-mannitol and the analogous D-sorbitol derivative have been described.97... 

The hexitol anhydrides also have medicinal uses.97 Carr and Krantz98 found that l,4 3,6-dianhydro-D-mannitol was quite non-toxic to man and was a valuable diuretic. The dinitrates of both isomannide and isosorbide" have possible uses as agents for lowering blood pressure, though Burn and Stephenson100 found that the D-sorbitol derivative was twice as active as the D-mannitol derivative in this respect. 2,5-Diam-ino-2,5-didesoxy-l,4 3,6-dianhydro-D-mannitol and -D-sorbitol have been prepared and their sulfanilamido derivatives obtained.101 These however showed no outstanding bacteriostatic activity. 

Other renewable resources sorbitol (I), cellobiose (XXV), etc. can be used in similar ways as starting materials in the preparation of epoxy resins. We are now working on a direct two-step preparation of diepoxy sorbitol derivatives by direct halogenation of the two primary hydroxyl groups with the formation of 1,6-dichloro-1,6-dideoxy-sorbitol, (XXIII), followed by epoxy ring formation (1,2 5,6-dianhydrosorbitol (XXIV) ... 

Some interesting resins have been obtained from the dianhydrides through their acrylic or methacrylic esters. Thus, 2,5-dimethacrylyl-l,4 3,6-dianhydro-mannitol (XIX) was formed by treating dianhydro-mannitol with methacrylyl chloride in the presence of sodium hydroxide. The product, a crystalline compound, polymerized extremely rapidly to a colorless, transparent, infusible resin. The corresponding sorbitol derivative, however, was an oil which polymerized to a softer resin. On the other hand, 2,5-diacrylyl-l,4 3,6-dianhydro-sorbitol (XX) was a crystalline compound, which polymerized to a hard, infusible, glass-like resin. 

The dianhydrides of mannitol and sorbitol also form two crystalline dinitrates (XXI) and (XXII), both of which are blood-pressure depressants. Curiously enough the sorbitol derivative is twice as active as the mannitol derivative, although both are less active than glycerol trinitrate. Both anhydrides give rise to amino derivatives, 2,5-... 

A sirupy pentapropionate of L-sorbose was described by Hurd and Gordon.142 Crystalline esters of L-sorbose, such as the 1-benzoyl-,55 1-p-aminobenzoyl-148 and 1-tosyl-, 144,56 have also been synthesized. 1-p-Aminobenzoyl-L-sorbose was prepared as a possible substance for measuring the rate of glomerular filtration. It was synthesized by esterifying 2,3 4,6-diisopropylidene-L-sorbose with p-nitrobenzoyl chloride, with subsequent reduction of the nitrobenzoyl ester to 1-p-amino-benzoyl-2,3 4,6-diisopropylidene-L-sorbose. Removal of the isopropyli-dene groups by dilute acid hydrolysis furnished the desired product. 1-Tosyl-L-sorbose was independently prepared by two different methods. The first method,55 discussed on page 110, involves the oxidation of a properly substituted sorbitol derivative, while the latter method144 is similar to the one used for the preparation of the 1-p-aminobenzoyl derivative, namely esterification of 2,3 4,6-diisopropylidene-L-sorbose, followed by acid hydrolysis. This cyclic acetal has also been esterified to the crystalline l-mesyl-2,3 4,6-diisopropylidene-L-sorbofuranose by... 

Fig, 3, It should be emphasized that a careful examination of the cyclodextrin derivatives must be performed after the final purification. Several authors have indicated that incomplete derivatization may be the reason for irreproducible results. Except for thorough NMR investigations ( H- and C-NMR), the "reductive cleavage" of cyclodextrin derivatives and subsequent quantitative gas chromatographic analysis of the 1,5-anhydro-sorbitol derivatives as developed by Mischnick-Lubbecke and Krebber (35) have proved a sensitive and reliable method to detect even traces of under-or over-alkylated derivatives. 

On an industrial scale, the SFE-FTIR couple has been successfully used to determine aramid, polyamide and polyurethane-based fibres, which require a different finish for textile processing [127], By using CO, at 350 atm, 75°C and a flow-rate of 1.2 ml/min, the polyurethane finish [poly(dimethylsiloxane) oil] was thoroughly extracted within the first 10 min by contrast, less than 35% of sorbitol derivatives present in the aramid finish could be separated after 20 min. The separation efficiency for polyamide finish components varied between 74 and 100%, with relative standard deviations for the most extractable finishes — which were recovered by more than 98% — ranging from 5.7 to 21%. 

The sorbitol market is mature and will remain steady. Growth may come from the polymer industry with the use of sorbitol derivatives as plasticizers. 

When the carbonyl group of a sugar is reduced to a hydroxyl group, the resulting compound is one of the polyhydroxy alcohols known as alditols. Two compounds of this kind, xylitol and sorbitol, derivatives of the sugars xylulose and sorbose, respectively, have commercial importance as sweeteners in sugarless chewing gum and candy. 

Definition Ethoxylated sorbitol deriv. of beeswax with avg. 6 moles EO Properties Nonionic... 

Examples of clarifiers include a number of sorbitol derivatives such as bis (3, 4 dimethyl benzylidene) sorbitol diacetal, and alumiitium hydroxy bis (4-tert-butyl) benzoate. 

Most of the current clarifiers are sorbitol derivatives. They include Great Lakes Clearlite NU 005, and Ciba s Irgaclear additives, some of which are now manufactured by Roquette in France, as well as NC-4 sorbitol acetal clarifiers supplied by Mitsui Toatsu Chemicals in Japan. One exception is Dover Chemical s Doverlube FL-599, a polyethylene glycol ester offered for clarifying polypropylene and also as a process aid for high impact polystyrene. 

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