Isosorbide diesters

Preparation of trans-isosorbide diester bromo ether intermediate... 

The isosorbide diester 167 acts as an excellent antioxidant and heat stabilizer for several polymers.261... 

Synthetic variation is limited only by the availability of the alkanoic acids. Depending on whether the alkanoic acid is linear or branched and the chain length, the alkanoic acid can be derived from either petrochemical or renewable resources. Over 15 different types of isosorbide diesters have been synthesised. 

It was found that isosorbide diesters are functionally comparable with the equivalent phthalates. Required properties, such as volatility, can be tuned by variation of the ester groups. Extensive testing in PVC formulations has shown that isosorbide diesters are primary plasticisers, are highly compatible with PVC, have good thermal stability, have excellent optical properties and have good migration/extraction characteristics. 

Cation-exchange resin such as Amberlyst 15 has been used for the esterification of isosorbide with -octanoic acid [132], giving the corresponding diesters in 98% yield. 

Some special esters of isohexides (prepared conventionally, however) have been described, including diesters of several long-chain fatty acids121,122 and dicarboxylic acids,123 isomannide-mono-oleate,124 isosorbide dinicotin-ate,125 and perfluorinated long-chain fatty acid diesters of isosorbide and isomannide.126 Bis(chloroformate)s of isosorbide and isomannide, and the... 

In the mid-sixties, Atlas Chemical Industries investigated the reaction of epoxides with isohexides. Transformation of isosorbide (3) by ethylene oxide affords polyoxyethylene isosorbide (62), which was treated with oleic acid to afford the corresponding diesters (63), and these were further transformed into epoxidized products167 (64) (see Scheme 12). On treating all three iso-... 

By addition of each of several diesters of isosorbide, isomannide, and isoidide to a nematic phase, cholesteric phases can be produced. All compounds exhibit a large twisting power. In the cholesteric phase, helix inversion, large or small temperature-dependencies of the pitch, and broad blue phases were achieved.183... 

Isosorbide, an l,4 3,6-dianhydrohexitol, is readily obtained from the double dehydration of sorbitol. Amongst other chemical derivatives, diesters and diethers of sorbitol have already found application as solvents or plasticizers. Functionalization of the two alcohols groups attached to the rather rigid V-shaped framework of the two... 

---