Role of acid sites and selectivity correlation in solvent free liquid phase dehydration of sorbitol to isosorbide

Dabbawala, Aasif A.; Mishra, Dinesh Kumar; Huber, George W.; Hwang, Jung Yeon

doi:10.1016/j.apcata.2014.12.014

Cited by 77 publications

(48 citation statements)

References 46 publications

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“…The higher acid strength of such catalysts may also be another reason for their low selectivity. In our previous study using distinct homogeneous acid catalysts, we observed that the triflic acid having higher acid strength produced higher amount of side products than p-toluene sulfonic acid and methane sulfonic acid catalysts [24]. The above achieved results with distinct catalysts having different organoacid sites clearly point out important of type of functional acidic group and influence of ordered mesoporous structure in improvement of catalyst performance.…”

Section: Accepted Manuscriptmentioning

confidence: 73%

“…The sorbitol dehydration is influence by catalyst acid strength and nature of acid sites. The catalysts with Brönsted acid sites are more efficient for the production of isosorbide [24]. Ar/SBA-15 contains Brönsted acid site with high acid strength than Pr/SBA-15 (Fig.…”

Section: Catalytic Dehydration Of Sorbitolmentioning

confidence: 95%

“…After separating catalyst by centrifuge, the supernatant solution was titrated by a 0.01 M HCl solution using phenolphthalein as an indicator. The solvent free dehydration of sorbitol was performed in simple reactor setup under reduce pressure and the composition of products was analyzed using HPLC [24]. For catalyst reuse and regeneration, the water/ethanol was added to the reaction mixture to dissolve product and then filtered to separate solid catalyst from the product.…”

Section: Methodsmentioning

confidence: 99%

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Arenesulfonic acid functionalized ordered mesoporous silica as solid acid catalyst for solvent free dehydration of sorbitol to isosorbide

Dabbawala

Park

Valekar

et al. 2015

Catalysis Communications

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Section: Accepted Manuscriptmentioning

confidence: 73%

Section: Catalytic Dehydration Of Sorbitolmentioning

confidence: 95%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Arenesulfonic acid functionalized ordered mesoporous silica as solid acid catalyst for solvent free dehydration of sorbitol to isosorbide

Dabbawala

Park

Valekar

et al. 2015

Catalysis Communications

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“…As can be seen the optimal temperature was 130 °C, leading to 87 % yield of isosorbide. Temperatures below 130 °C led to slower reactions, whereas the isosorbide yield was reduced beyond 130 °C because of the formation of insoluble dark polymeric materials (“humins”).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Isosorbide Esters from Sorbitol with Heterogeneous Catalysts

Fraile

Saavedra

2017

ChemistrySelect

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Sulfonic solids of different nature (alkyl, aryl and perfluoroalkyl sulfonic) are able to catalyze the dehydration of sorbitol under solvent free conditions at moderate temperature (130 °C) under vacuum and the esterification of isosorbide with carboxylic acids, either acetic or octanoic acids. Yields around 80 % of isosorbide can be obtained from sorbitol with only 1 mol% catalyst after 24 h. Yields of dicarboxylates from isosorbide were in the range of 70–80 % for diacetate and up to 97 % for dioctanoate. The two‐step one‐pot process from sorbitol is highly efficient for isosorbide diacetate (up to 71 % yield), whereas the esterification with octanoic acid is more sensitive to the presence of by‐products (up to 57 % yield).

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“…11,12,13 More recently, 14 it was reported that conventional heating with NaHSO 4 only yielded 14% isosorbide and a 77% unresolved mixture of 1,4-and 1,5-sorbitans after 60 min at 180°C under 100 mm residual pressure with about 1.8% (mol) of catalyst in a solvent free system.…”

Section: Introductionmentioning

confidence: 98%

Solvent- and Microwave-Assisted Dehydrations of Polyols to Anhydro and Dianhydro Polyols

et al. 2015

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Carbohydrate polyol (sorbitol, mannitol and xylitol) dehydrations by both strong and weak acid catalysts were enhanced by microwave irradiation when performed in aqueous dioxane. Reaction conditions such as the percent of water, type and concentration of acid, reaction time, and temperature were varied. Reactions with different conditions were compared by using the Combined Severity parameter. An 88% yield of the dianhydropolyol isosorbide was achieved by heating sorbitol in a microwave for only 20 min at 205⁰C in 7% water/dioxane with H 2 SO 4 as the catalyst, while heating for 1.5 h at 210⁰C with the weak acid salt NaHSO 4 gave 74% isosorbide.An 85% yield of 1,4-anhydroxylitol was achieved by heating xylitol in a microwave, with H 2 SO 4 as the catalyst, for 15 min at 180⁰C in 28%water/dioxane. Increasing reaction severity in the presence of the H 2 SO 4 catalyst gave organic sulfate impurities due to solvent cleavage; in contrast, no solvent cleavage was observed with the weak acid catalyst NaHSO 4 .

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Role of acid sites and selectivity correlation in solvent free liquid phase dehydration of sorbitol to isosorbide

Cited by 77 publications

References 46 publications

Arenesulfonic acid functionalized ordered mesoporous silica as solid acid catalyst for solvent free dehydration of sorbitol to isosorbide

Arenesulfonic acid functionalized ordered mesoporous silica as solid acid catalyst for solvent free dehydration of sorbitol to isosorbide

Synthesis of Isosorbide Esters from Sorbitol with Heterogeneous Catalysts

Solvent- and Microwave-Assisted Dehydrations of Polyols to Anhydro and Dianhydro Polyols

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