13042-39-2Relevant articles and documents
Volatile short-chain amphiphiles derived from isosorbide: Hydrotropic properties of esters vs. ethers
Lavergne, Aurelie,Moity, Laurianne,Molinier, Valerie,Aubry, Jean-Marie
, p. 5997 - 6007 (2013)
Two series of short-chain isosorbide monoalkanoates, differing from the free hydroxyl position, were synthesized and evaluated as volatile non-ionic hydrotropes, also known as solvo-surfactants . Their aqueous solubilities, solubilizing efficiencies and volatilities were evaluated and compared to the corresponding 5-O-alkylisosorbides. Whatever the acylation position (5-O- or 2-O-), isosorbide monoalkanoates are poorly water-soluble for acyl chains longer than four carbons, whereas 5-O-alkylisosorbides are completely miscible with water up to a pentyl chain, which seems to indicate that an ether link brings more hydrophilicity than an ester bond for these types of molecules. The shorter isosorbide monoalkanoates are completely miscible with water and the butanoates are particularly efficient in terms of aqueous solubilization of hydrophobic compounds. In addition, all hydrotropes exhibit some volatility albeit being non-VOC and contrarily to their ethers homologues, isosorbide alkanoates are easily hydrolysed in basic medium, which suggests a good biodegradability.
Method for synthesizing isohexitol ester
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Paragraph 0010; 0043-0050; 0055-0056, (2021/05/05)
The invention discloses a method for synthesizing isohexitol ester, which is characterized in that a material containing hexitol and an esterifying agent is contacted with a solid acid catalyst in the presence of an aprotic solvent, and the isohexitol ester is obtained through one-pot one-step reaction. The method is especially suitable for the reaction of directly synthesizing the isohexitol ester, especially isosorbide ester, from hexitol, especially sorbitol, the total yield of the obtained isohexitol ester is 80% or above, and the yield of the isosorbide dicarboxylate reaches 60% or above.
Development of a Practical Enzymatic Synthesis of Isosorbide-2-acetate
Zhu, Shi-Guo,Huang, Jia-Xin,Zhang, Gui-Min,Chen, Shao-Xin,Zhang, Fu-Li
, p. 1548 - 1552 (2018/11/25)
Using immobilized lipase, we developed an enzymatic synthesis of isosorbide-2-acetate (1), a key intermediate in the preparation of isosorbide-5-mononitrate. 1 was prepared in high yield (~92%) with excellent regioselectivity (>99.5% d.e.) through hydrolysis (Novozym 435) or alcoholysis (lipase PS IM) of isosorbide-2,5-diacetate. The conditions for the enzymatic process were optimized. The substrate concentration could be 400-500 g/L, and the enzyme to substrate ratio was 10 wt %. The feasibility of enzyme recycling was also demonstrated. In addition, the enzymatic process was carried out on a kilogram scale and was proved to be scalable, efficient, and economical.