Cascade Synthesis of Five‐Membered Lactones using Biomass‐Derived Sugars as Carbon Nucleophiles

Yamaguchi, Sho; Matsuo, Tetsuji; Motokura, Ken; Miyaji, Akimitsu; Baba, Toshihide

doi:10.1002/asia.201600307

Cited by 8 publications

(4 citation statements)

References 47 publications

(10 reference statements)

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“…However, this result is inconsistent with the conversion of 3- or 6-carbon sugars into 2 . SnCl 4 has the best performance among tin halides (SnCl 4 , SnBr 4 , and SnI 4 ) for the production of 2 from 3- or 6-carbon sugars 24–27 . As chloride has the largest electronegativity among halogen atoms, the strong Lewis acidity of Sn in SnCl 4 seems to accelerate the retro aldol reaction, dehydration, and 1,2-hydride shift.…”

Section: Discussionmentioning

confidence: 99%

Development of New Carbon Resources: Production of Important Chemicals from Algal Residue

Yamaguchi

Kawada

Yuge

et al. 2017

Sci Rep

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Algal biomass has received attention as an alternative carbon resource owing not only to its high oil production efficiency but also, unlike corn starch, to its lack of demand in foods. However, algal residue is commonly discarded after the abstraction of oil. The utilization of the residue to produce chemicals will therefore increase the value of using algal biomass instead of fossil fuels. Here, we report the use of algal residue as a new carbon resource to produce important chemicals. The application of different homogeneous catalysts leads to the selective production of methyl levulinate or methyl lactate. These results demonstrate the successful development of new carbon resources as a solution for the depletion of fossil fuels.

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Section: Discussionmentioning

confidence: 99%

Development of New Carbon Resources: Production of Important Chemicals from Algal Residue

Yamaguchi

Kawada

Yuge

et al. 2017

Sci Rep

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“…The use of aldehydes instead of formaldehyde can yield a wide range of products in the multistep HBL preparation process. Indeed, our group reported the cascade synthesis of 5-membered lactones using a combination of DHA and various aldehydes [68] (Scheme 15). Such a synthetic route is particularly advantageous, as 5-membered lactones can be utilized not only as fine chemicals but also as raw materials.…”

Section: Cascade Synthesis Of 5-membered Lactones Using Biomass-dementioning

confidence: 99%

A Novel Strategy for Biomass Upgrade: Cascade Approach to the Synthesis of Useful Compounds via C-C Bond Formation Using Biomass-Derived Sugars as Carbon Nucleophiles

Yamaguchi

Baba

2016

Molecules

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Due to the depletion of fossil fuels, biomass-derived sugars have attracted increasing attention in recent years as an alternative carbon source. Although significant advances have been reported in the development of catalysts for the conversion of carbohydrates into key chemicals (e.g., degradation approaches based on the dehydration of hydroxyl groups or cleavage of C-C bonds via retro-aldol reactions), only a limited range of products can be obtained through such processes. Thus, the development of a novel and efficient strategy targeted towards the preparation of a range of compounds from biomass-derived sugars is required. We herein describe the highly-selective cascade syntheses of a range of useful compounds using biomass-derived sugars as carbon nucleophiles. We focus on the upgrade of C2 and C3 oxygenates generated from glucose to yield useful compounds via C-C bond formation. The establishment of this novel synthetic methodology to generate valuable chemical products from monosaccharides and their decomposed oxygenated materials renders carbohydrates a potential alternative carbon resource to fossil fuels.

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“…In addition to the after‐mentioned advantages, there are some drawbacks of using biomass alone as a feedstock. The major issues related to biomass include the presence of an excessive amount of water, oxygen and ash that contribute to decreasing the heating values, hence the efficiency of the process [4,5] …”

Section: Introductionmentioning

confidence: 99%

Apparent Kinetics of Co‐Gasification of Biomass and Vacuum Gas Oil (VGO)

Al‐Attas

Lucky

Hossain

2021

Chemistry An Asian Journal

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This communication reports the beneficial effects of co‐gasification of biomass and residual oil to produce syngas. In this regard, various blends of glucose (a biomass surrogate) to vacuum gas oil (VGO) have been employed to investigate the synergic effects on the gasification process. The non‐isothermal co‐gasification experiments were conducted in a thermogravimetric analyzer at different heating rates and gasifying agents. The analysis showed that the co‐gasification rate increased with the increase of glucose content in the feedstock. The presence of the oxygen in the biomass molecules helped the overall gasification process. The maximum gasification rate of 42.70 wt/min (DTGmax) was observed with 25 wt% glucose containing sample. The use of gasifying agents appeared to have some influence, especially during high temperature gasification of the glucose‐VGO blends. At a same gasification temperature, the co‐gasification rate of glucose‐VGO blends were found to be 125.7 wt/min and 98.59 wt%/min for N2 and CO2, respectively. The kinetics of the co‐gasification of glucose‐VGO blends was conducted based on modified random pore model using TGA experimental data and implemented in MATLAB. The estimated activation energy and rate constants were found to be consistent to the observed co‐gasification rates. The apparent activation energies of co‐gasification of VGO/biomass blends with different weight percentages shows values ranging 60.56–48.25 kJ/mol. The kinetics analysis suggested that the addition of biomass helped to increase the reaction rate by lowering the activation energy required for accomplishing the reactions compared with petroleum carbonaceous feedstocks. The reaction rate constants isotherms are plotted to show that the k‐values are exhibiting similar trends at moderate heating rates between 20 and 60 °C/min. This remark arises due to the nature of the reactions involved which are considered to be inherently similar in this range of heating rate.

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Cascade Synthesis of Five‐Membered Lactones using Biomass‐Derived Sugars as Carbon Nucleophiles

Cited by 8 publications

References 47 publications

Development of New Carbon Resources: Production of Important Chemicals from Algal Residue

Development of New Carbon Resources: Production of Important Chemicals from Algal Residue

A Novel Strategy for Biomass Upgrade: Cascade Approach to the Synthesis of Useful Compounds via C-C Bond Formation Using Biomass-Derived Sugars as Carbon Nucleophiles

Apparent Kinetics of Co‐Gasification of Biomass and Vacuum Gas Oil (VGO)

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