Chemocatalytic value addition of glucose without carbon–carbon bond cleavage/formation reactions: an overview

Abstract

Recent advances on the production and applications of major C6 products from glucose have been reported in this review. The preparation and derivative chemistry of sorbitol, sorbitan, 5-(hydroxymethyl)furfural, and isosorbide have been elaborated.

Greening the Synthesis of Biorenewable Fuels and Chemicals by Stoichiometric Reagentless Organic Transformations

“…83,84 More importantly, all the synthetic steps of synthesizing IS from cellulose can be made reagentless without any carbon− carbon (C−C) bond cleavage reactions (Scheme 5). 85 Analogous synthetic pathways form isomannide (IM) and isoidide (II), starting from mannose and idose, respectively. IS can also be converted into IM and II by isomerization under catalytic conditions, which can also be termed reagentless synthesis since no reagent gets consumed during the process.…”

Selective One-Pot Synthesis of Sorbitans (1,4-Sorbitan and 3,6-Sorbitan) from Glucose via Catalytic Hydrogenation and CO2-Mediated Dehydration

“…Industrially, 1,4-sorbitan is a major product obtained through the monodehydration of sorbitol using a potent acid catalyst . Sorbitol itself is derived from the hydrogenation of glucose, primarily obtained through starch hydrolysis but also from sources like sucrose or cellulose. − Consequently, the valorization of cellulose can be achieved by a one-pot conversion process to produce 1,4-sorbitan.…”

Methyl isobutyl ketone-enabled selective dehydration–esterification of sorbitol to isosorbide esters over the H-beta catalyst

“…12,13 In this respect, sorbitol can be upgraded to diol isosorbide or isosorbide derivatives by selective removal and functionalization of the hydroxyl groups, which retains the original carbon skeleton, resulting in the efficient utilization of the sorbitol polyhydroxyl structure. 14,15 Of particular significance in the downstream derivatives are valuable isosorbide esters due to their wide applications as plasticizers, surfactants, lubricants, emulsifiers, solvents, pharmaceutical intermediates or polymer monomers. [16][17][18][19][20] In particular, isosorbide diesters are promising biobased green plasticizers to replace traditional petro-based phthalates for the production of polyvinyl chloride products requiring safety and non-toxicity, such as children's toys, medical devices or food packaging.…”

“…[21][22][23] Isosorbide esters are currently produced via esterification starting from isosorbide and carboxylic acids by enzymatic or acid-catalyzed routes. 15,24 Lipase-catalyzed esterification has been investigated for the selective synthesis of isosorbide esters from isosorbide with several fatty acids such as octanoic acid and oleic acid. [25][26][27] However, this method is hindered due to long reaction times and high-cost enzymes.…”

“…Given the advantages of the one-step strategy, 33 direct dehydration-esterification of sorbitol to isosorbide esters is a green and atom-economical process featuring simplified process operation and high efficiency. However, in spite of the extensive literature concerning separate reactions of sorbitol dehydration [34][35][36] and isosorbide esterification, 15 respectively, literature on the dehydration-esterification of sorbitol to isosorbide esters is extremely scarce. In particular, the dehydration-esterification of sorbitol with short-chain fatty acids requires a two-step process to access the corresponding isosorbide esters, which suffered from cumbersome and time-consuming multiple reaction steps and unsatisfactory efficiency.…”