10334-28-8Relevant academic research and scientific papers
Efficient and selective aqueous photocatalytic mono-dehydration of sugar alcohols using functionalized yttrium oxide nanocatalysts
Cheng, Yu,Fan, Chao,Guo, Lina,Huang, Benhua,Li, Xiaoyong,Luque, Rafael,Ma, Xiaomo,Meng, Xu,Pan, Cheng,Sun, Yang,Yang, Juncheng,Zhang, Junjie,Zhang, Weining,Zheng, Aqun
, p. 5333 - 5344 (2020)
The mono-dehydration of sugar alcohols such as d-sorbitol and d-mannitol generates 1,4-sorbitan and 1,4-mannitan, respectively, which are relevant platform molecules for the synthesis of detergents and pharmaceuticals. Most reported catalytic systems provided access to di-dehydrated products, while mono-dehydration required special efforts, particularly regarding selectivity and reaction temperature. A series of functionalized yttrium oxides were prepared via sol-gel synthesis in this work, which not only showed an interesting micropipe-like morphology, but also contained functional components. These materials were investigated as photocatalysts in the dehydration of d-sorbitol and d-mannitol, exhibiting high selectivity to mono-dehydration. The effects of solvent, temperature and catalyst were fully discussed. A catalytic mechanism was proposed based on the experimental results and calculations.
Liquid-phase dehydration of sorbitol under microwave irradiation in the presence of acidic resin catalysts
Khan, Nazmul Abedin,Mishra, Dinesh Kumar,Hwang, Jin-Soo,Kwak, Young-Woo,Jhung, Sung Hwa
, p. 1231 - 1238 (2011)
Liquid-phase dehydration of sorbitol has been investigated in wide reaction conditions especially under microwave irradiation in the presence of acidic resin catalysts. From the selectivity for sorbitan and isosorbide, it can be understood that the dehydration is a consecutive reaction (sorbitol to sorbitan, and finally to isosorbide) and that the sorbitan is an intermediate of the dehydration. By using microwave irradiation, the dehydration can be accelerated by around 20-34 times compared with the rate by conventional electric heating at the same temperature, or the reaction temperature can be decreased by around 40 °C for the comparable conversion in a similar reaction time. However, the microwaves do not have noticeable effects on the selectivity for isosorbide or sorbitan. The accelerated dehydration under microwaves is mainly due to decreased activation energy.
Br?nsted acidic ionic liquid-catalyzed dehydrative formation of isosorbide from sorbitol: Introduction of a continuous process
Deng, Jie,Xu, Bao-Hua,Wang, Yao-Feng,Mo, Xian-En,Zhang, Rui,Li, You,Zhang, Suo-Jiang
, p. 2065 - 2073 (2017)
A highly efficient synthesis of isosorbide from sorbitol was developed using Br?nsted acidic ionic liquids (BILs) as the catalyst for the first time. The structure-performance relationship was discussed extensively and a proper value of the Gutmann acceptor number (AN) rather than the inherent of acidity was found to be essential for an optimized yield of isosorbide. In addition, the excellent behavior of preferred BIL-4 in the consecutive recycling tests renders the construction of a continuous process probable. Systematic optimization demonstrated that a yield of 82% of isosorbide with a purity of 99.3% could be reached at balance.
Arenesulfonic acid functionalized ordered mesoporous silica as solid acid catalyst for solvent free dehydration of sorbitol to isosorbide
Dabbawala, Aasif A.,Park, Jung J.,Valekar, Anil H.,Mishra, Dinesh K.,Hwang, Jin-Soo
, p. 207 - 211 (2015)
Abstract Organosulfonic acid functionalized ordered mesoporous silicas with different moieties have been synthesized and used as solid acid catalysts for solvent free dehydration of sorbitol to isosorbide. In screening experiments with distinct solid acids, the arenesulfonic acid functionalized SBA-15 (Ar/SBA-15) showed higher catalyst performance as compared to propyl and fluorosulfonic acid sites. Under optimum reaction condition, Ar/SBA-15 afforded 100% sorbitol conversion with 71% isosorbide selectivity in 2 h at moderate temperature of 170°C. The high activity of catalyst ascribed to its ordered mesoporous structure and ease to access Br?nsted acid sites with high acid strength.
Role of acid sites and selectivity correlation in solvent free liquid phase dehydration of sorbitol to isosorbide
Dabbawala, Aasif A.,Mishra, Dinesh K.,Huber, George W.,Hwang, Jin-Soo
, p. 252 - 261 (2015)
A number of Br?nsted acids (methanesulfonic acid, p-toluene sulfonic acid, triflic acid, sulfamic acid, citric acid, NaHSO4, and boric acid) and Lewis acids (metal sulfate/triflates) were employed in solvent free dehydration of sorbitol and their influence on anhydroalcohols selectivity has been investigated. The outcome indicated that all the acid catalysts produced first mono-dehydrated product sorbitan followed by second dehydration of 1,4-sorbitan to isosorbide. However, the formation and yield isosorbide were found to depend on the nature of acid sites and their acidic strength. The Br?nsted acids are more efficient to convert sorbitol to isosorbide than Lewis acids. The Br?nsted acids having lower pKa value (i.e. strong acid) exhibited high catalytic activity as well as yield of isosorbide. In the case of Lewis acids, the catalytic activity and selectivity were radically depended on which metal used and their stability during the reaction. The water formed during reaction induced Br?nsted acidity on Lewis acid metal site. The Lewis-assisted Br?nsted acid site enabled high yield of isosorbide up to 70% at moderate temperature (160°C).
Enhanced catalytic performance in dehydration of sorbitol to isosorbide over a superhydrophobic mesoporous acid catalyst
Zhang, Jian,Wang, Liang,Liu, Fujian,Meng, Xiangju,Mao, Jianxin,Xiao, Feng-Shou
, p. 249 - 254 (2015)
A superhydrophobic mesoporous polymer-based acid catalyst (P-SO3H) was synthesized from solvothermal co-polymerization. The N2 sorption isotherms indicate the rich porosity of P-SO3H, confirmed by the TEM image. The IR spectra indicate the presence of sulfonic acid groups. Interestingly, P-SO3H gives contact angle of water droplet on the sample surface at 154°, suggesting its superhydrophobicity. More importantly, P-SO3H is highly efficient catalyst for dehydration of sorbitol to isosorbide, giving sorbitol conversion higher than 99.0% and isosorbide yield at 87.9%. In addition, P-SO3H exhibits excellent recyclability. After recycles for 5 times, the isosorbide yield is still 77.7%. In contrast, conventional acid catalyst of Amberlyst-15 shows the yield at only 15.4% after recycles for 3 times. The unique catalytic properties are reasonably related to the superhydrophobicity and porosity of P-SO3H. The sample large porosity offers a high degree of the exposed acidic sites to the reactants, and the sample superhydrophobicity would keep the water formed in the dehydration away from the catalyst, promoting the reaction equilibrium. As a result, the catalytic performance in dehydration of sorbitol to isosorbide over the superhydrophobic P-SO3H catalyst is significantly enhanced, compared with conventional acid catalyst of Amberlyst-15.
Selective conversion of concentrated microcrystalline cellulose to isosorbide over Ru/C catalyst
Liang, Guanfeng,Wu, Chaoyong,He, Limin,Ming, Jun,Cheng, Haiyang,Zhuo, Linhai,Zhao, Fengyu
, p. 839 - 842 (2011)
Highly concentrated microcrystalline cellulose was directly converted to isosorbide with yields of 35-50%, providing a new approach for producing important fine chemicals from biomass. The Royal Society of Chemistry.
Selective dehydration of sorbitol to 1,4-anhydro-d-sorbitol catalyzed by a polymer-supported acid catalyst
Xiu, Yuhe,Chen, Angjun,Liu, Xuerui,Chen, Chen,Chen, Jizhong,Guo, Li,Zhang, Ran,Hou, Zhenshan
, p. 28233 - 28241 (2015)
Novel polymer-supported Bronsted acid polymer catalysts have been successfully synthesized by radical polymerization, followed by a simple solvothermal route and ion exchange step. The as-synthesized co-polymers were characterized by Elemental Analysis, FT-IR spectroscopy, thermogravimetric analysis and scanning electron microscopy and then were employed as a heterogeneous catalyst for dehydration of sorbitol. Especially, the polymer catalysts have a unique advantage of adjustable Bronsted acidity, and the polymer with 1.82 mmol g-1 of Bronsted acidity was a very efficient catalyst for highly selective dehydration of sorbitol into 1,4-anhydro-d-sorbitol. The dehydration reaction can be completed within 4 h and the selectivity of 1,4-anhydro-d-sorbitol achieved 90%. Moreover, the present catalysts resisted acid-leaching and can be recycled in five consecutive cycles without obvious loss of activity. This journal is
PERFLUOROALKYLATED MONOESTERS OF 1,4-D-SORBITAN, ISOSORBIDE AND ISOMANNIDE: NEW SURFACTANTS FOR BIOMEDICAL APPLICATIONS
Zarif, Leila,Greiner, Jacques,Riess, Jean G.
, p. 73 - 86 (1989)
A one step selective synthesis of pure 1,4-D-Sorbitan monoesters 4 was achieved by treating 1,4-D-Sorbitan 1 with RF9CH2)nCOCl (RF=C4F9, C5F11, C8F17; n=2, 10) in pyridine at room temperature. (13)C NMR establishes that esterification occured on carbon 6 only.While isomannide, 3, gives only one monoester, 8, the less symmetrical isosorbide 2 leads to two monoesters displaying significantly different physical properties.These compounds display moderate surface activities and do not perturb the growth and viability of Namalva lymphoblastold cell cultures.
Dehydration of sorbitol to isosorbide over sulfonic acid resins under solvent-free conditions
Ginés-Molina, María José,Moreno-Tost, Ramón,Santamaría-González, José,Maireles-Torres, Pedro
, p. 66 - 73 (2017)
Different commercial sulfonic acid resins (Purolite and Amberlyst type) have been evaluated as acid catalysts for the dehydration of sorbitol to isosorbide. These acidic resins differ in their acid properties, as well as in their thermal and mechanical stabilities. Dehydration of sorbitol has been carried out under solvent-free conditions, by melting sorbitol. At the beginning of reaction, different sorbitans (monodehydration products) were detected, whose dehydration and subsequent cyclization lead to the formation of isosorbide. A maximum yield of 75% is reached after 12?h at 413?K, by using a 5?wt% of Purolite CT269, at atmospheric pressure. This resin maintains its catalytic activity after four runs, and the stability is corroborated by the negligible presence of sulphur species (coming from sulfonic acid leaching) in the reaction medium. This suitable catalytic performance can be explained by its high acid capacity (5.2?meq?g?1) and mechanical and thermal stabilities associated to the macroreticular structure.
