Enhancement of cyclic ether formation from polyalcohol compounds in high temperature liquid water by high pressure carbon dioxide

Yamaguchi, Aritomo; Hiyoshi, Norihito; Sato, Osamu; Bando, Kyoko K.; Shirai, Masayuki

doi:10.1039/b812318g

Cited by 62 publications

(60 citation statements)

References 17 publications

(10 reference statements)

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“…Figure 7 shows the THFA and 3-HTHP formation rates as a function of square root of carbon dioxide pressure for 1,2,5-PTO dehydration. The formation rates also increased with an increase in square root of carbon dioxide pressure over 9 MPa of carbon dioxide pressure [7]. Linear relations between the ester formation rates and square root of carbon dioxide pressure were not obtained for the dehydration of 1,2,4-BTO and 1,2,5-PTO, indicating that the ester formation reaction is not the first order of proton concentration, unlike the glycerol dehydration.…”

Section: Dehydration Of Glycerol In High-temperaturecontrasting

confidence: 48%

“…The combination of water and carbon dioxide are environmentally benign because the added carbon dioxide can be separated easily by simple depressurization after the reaction. We reported the dehydration reactions of glycerol [6], 1,2,4-BTO, and 1,2,5-PTO [7] in high-temperature liquid water under high-pressure carbon dioxide. In this contribution, we focused on the comparison of the carbon dioxide effects on their dehydration reactions.…”

Section: Introductionmentioning

confidence: 99%

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Dehydration of Triol Compounds in High-Temperature Liquid Water Under High-Pressure Carbon Dioxide

et al. 2010

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High-temperature liquid water treatment of triol compounds [1,2,3-propanetriol (glycerol), 1,2,4-butanetriol (1,2,4-BTO), and 1,2,5-pentanetriol (1,2,5-PTO)] was carried out using a batch reactor. Intramolecular dehydration to hydroxyacetone from glycerol, 3-hydroxytetrahydrofuran from 1,2,4-BTO, and both tetrahydrofurfuryl alcohol and 3-hydroxytetrahydropyran from 1,2,5-PTO proceeded in water at 573 K. The dehydration rates were enhanced by the addition of high-pressure carbon dioxide.

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Section: Dehydration Of Glycerol In High-temperaturecontrasting

confidence: 48%

Section: Introductionmentioning

confidence: 99%

Dehydration of Triol Compounds in High-Temperature Liquid Water Under High-Pressure Carbon Dioxide

et al. 2010

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“…Similar results were also obtained in carbonate buffers (0.0667 M, NaHCO 3 -Na 2 CO 3 , pH 8.2; 13.8% ethylene glycol, 16.0% propylene glycol, 14.4% 1,2,5-pentanetriol at 46.0% cellulose conversion). 1,2,5-pentanetriol, like ethylene glycol and propylene glycol and hexitols, is also a very significant precursor, which can be used to synthesize branched polyurethanes, value-added chemicals such as tetrahydrofurfuryl alcohol and 3-hydroxytetrahydropyran [21], and compounds with biological activity [22]. The best yield of 1,2,5-pentanetriol reported to date, to our knowledge, is 25.8% from furfural reaction [23].…”

Section: Resultsmentioning

confidence: 94%

Cellulose conversion to polyols on supported Ru catalysts in aqueous basic solution

2010

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It is of great significance and challenge to achieve direct conversion of cellulose to specific polyols, e.g., ethylene glycol and propylene glycol. For such selective conversion, a novel one-pot approach was studied by combination of alkaline hydrolysis and hydrogenation on supported Ru catalysts. A wide range of bases including solid bases, e.g., Ca(OH) 2 and La 2 O 3 , and phosphate buffers were examined in the cellulose reaction in water, and the cellulose conversions and polyol products depended largely on the basicity or pH values in the aqueous solutions. Ethylene glycol, 1,2-propanediol, and especially 1,2,5-pentanetriol were obtained with selectivities of 15%, 14% and 22%, respectively, at 38% cellulose conversion at pH 8 in phosphate buffer solution. These preliminary results provide potentials for efficient conversion of cellulose to targeted polyols by using the advantages of bases. cellulose, polyols, Ru catalysts, solid bases, aqueous basic solutions

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“…One of the side reactions is the dehydration to 1,4-anhydroerythritol, and this reaction can proceed easily under acidic conditions [63]. It has been reported that Re-Pd/C + Nafion/SiO 2 gave 50% yield of tetrahydrofuran from erythritol via 1,4-anhydroerythritol in dioxane [64].…”

Section: Glycerol Erythritolmentioning

confidence: 99%

Selective Hydrogenolysis of C–O Bonds Using the Interaction of the Catalyst Surface and OH Groups

Tomishige

Nakagawa

Tamura

2014

Topics in Current Chemistry

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Hydrogenolysis of C-O bonds is becoming more and more important for the production of biomass-derived chemicals. Since substrates originated from biomass usually have high oxygen content and various kinds of C-O bonds, selective hydrogenolysis is required. Rhenium or molybdenum oxide modified rhodium and iridium metal catalysts (Rh-ReO(x), Rh-MoO(x), and Ir-ReO(x)) have been reported to be effective for selective hydrogenolysis. This review introduces the catalytic performance and reaction kinetics of Rh-ReO(x), Rh-MoO(x), and Ir-ReO(x) in the hydrogenolysis of various substrates, where selectivity is especially characteristic. Based the model structure of the catalysts and the reaction mechanism, the role of the oxide components is to make the interaction between the OH groups in the substrates and the catalyst surface, and the role of metal components is to dissociate hydrogen molecule heterolytically to give hydride and proton.

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Enhancement of cyclic ether formation from polyalcohol compounds in high temperature liquid water by high pressure carbon dioxide

Cited by 62 publications

References 17 publications

Dehydration of Triol Compounds in High-Temperature Liquid Water Under High-Pressure Carbon Dioxide

Dehydration of Triol Compounds in High-Temperature Liquid Water Under High-Pressure Carbon Dioxide

Cellulose conversion to polyols on supported Ru catalysts in aqueous basic solution

Selective Hydrogenolysis of C–O Bonds Using the Interaction of the Catalyst Surface and OH Groups

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