89825-36-5

Basic information

• Product Name: isosorbide
• Synonyms: isosorbide
• CAS NO: 89825-36-5
• Molecular Weight: 146.143
• Mol File: 89825-36-5.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: isosorbide(CAS DataBase Reference)
• NIST Chemistry Reference: isosorbide(89825-36-5)
• EPA Substance Registry System: isosorbide(89825-36-5)

Safety Data

• Hazardous Substances Data: 89825-36-5(Hazardous Substances Data)

Upstream product

• 641-74-7 1,4:3,6-dianhydro-D-mannitol 
• 652-67-5 Isosorbide 
• 24808-18-2 di-O-acetyl-1,4;3,6-dianhydro-L-iditol 
• 470-15-5 α-L-sorbopyranose 
• 50-70-4 D-sorbitol 
• 616-38-6 carbonic acid dimethyl ester 
• 100-46-9 benzylamine 
• 54522-28-0 (3R,3aS,6R,6aS)-hexahydrofuro[3,2-b]furan-3,6-diyl bis(4-methylbenzenesulfonate) 
• 488-45-9 L-iditol 
• 7664-93-9 sulfuric acid 
• 64-17-5 ethanol 
• 7647-01-0 hydrogenchloride 
• 48107-55-7 (3R,3aR,6S,6aR)-hexahydrofuro[3,2-b]furan-3,6-diamine 
• 67-56-1 methanol 

Downstream Products

• 196812-16-5 1,6-dichloro-1,6-dideoxy-mannitol 
• 3014-56-0 (3S,3aR,6S,6aR)-6-(benzoyloxy)hexahydrofuro[3,2-b]furan-3-yl benzoate 
• 24808-19-3 (3S,3aS,6S,6aS)-6-[(methylsulfonyl)oxy]hexahydrofuro[3,2-b]furan-3-yl methanesulfonate 
• 54522-28-0 1,4:3,6-dianhydro-2,5-di-O-p-tosyl-D-iditol 

Relevant articles and documents

One-Pot Preparation of Dimethyl Isosorbide from d-Sorbitol via Dimethyl Carbonate Chemistry

Direct synthesis of dimethyl isosorbide (DMI) from d-sorbitol via dimethyl carbonate (DMC) chemistry is herein first reported. High yield of DMI was achieved using the nitrogen superbase 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as catalyst and performing the reaction in a stainless steel autoclave by increasing the temperature from 90 to 200 °C. In this procedure, DMC features its full capacity acting in the different steps of the process as carboxymethylating, leaving-group (cyclization), and methylating agent; DMC is also employed as the reaction media.

Unravelling the Mechanism of the Ru/C-Catalysed Isohexide and Ether Isomerization by Hydrogen Isotope Exchange

In this article we show that the catalytic isomerization of isohexide sugar alcohols as well as their respective ethers can occur by a hydride-based mechanism rather than a dehydrogenation/re-hydrogenation. C?H bonds in α-position to hydroxy and ether groups are activated using Ru/C as solid catalyst at temperatures as high as 160 °C and above. Hydrogen isotope exchange experiments proved that a full hydride exchange and isomerization is possible for isohexides but unexpectedly also for their methyl ethers. This is of great importance as it proves the co-existence of the both mechanisms for reactions that were so far assumed to occur solely by a dehydrogenation/re-hydrogenation. Hence, this co-existence should be taken into account for kinetic investigations of such reaction systems especially in the conversion of biomass-based chemicals under hydrogenation conditions. (Figure presented.).

ISOIDIDE MANUFACTURE AND PURIFICATION

Methods are provided for the conversion of isosorbide to isoidide, wherein the isosorbide contains sorbitan impurities. The impurities in the isosorbide subjected to epimerization are converted to hydrodeoxygenation products. A method for synthesizing isoidide, comprising, providing an isosorbide containing one or more sorbitans; and, epimerizing the isosorbide to form an epimerization product comprising isoidide and hydrodeoxygenation products.