Production of 5-(hydroxymethyl)-furfural from water-soluble carbohydrates and sugarcane molasses

Gomes, Gustavo R.; Rampon, Daniel S.; Ramos, Luiz Pereira

doi:10.1016/j.apcata.2017.07.049

Cited by 23 publications

(28 citation statements)

References 40 publications

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“…The HMF yields started to decrease at longer reaction times for both catalytic systems probably due to side reactions such as condensation to form water insoluble humins. 21,31 These undesirable side reactions took more time to occur in the ZnCl 2 /HCl system due to its lower acidic character, which slowed cellulose hydrolysis and decreased the availability of glucose for isomerization and dehydration to produce HMF.…”

Section: Resultsmentioning

confidence: 99%

“…The catalytic systems contained 0.3 mmol of each acid (ZnCl 2 or AlCl 3 and HCl) and the reaction was carried out at 180 o C for a total reaction time of 1 h. The presence of monosaccharides and organic acids in the reaction solvent (aqueous phase) was never observed and this was consistent with our previous work with sucrose and cane molasses, in which carbohydrates were totally consumed at temperatures of 180 °C. 21 By contrast, HMF and furfural were measured in the extraction solvent (THF) and their corresponding molar yields from glucans (equation 1) and xylans (equation 2) were determined in the extraction solvent (THF), respectively.…”

Section: Resultsmentioning

confidence: 99%

“…The total amount of NaCl required to form a biphasic system was 1.05 g and mechanical stirring was set at 1500 rpm. 21 The sugarcane bagasse samples were Wiley-milled to pass a 40-mesh screen. Kinetics of α-cellulose dehydration was profiled in both catalytic systems (ZnCl 2 /HCl and AlCl 3 /HCl) and this was done by withdrawing reaction aliquots at every 15 min for ZnCl 2 /HCl and 5 min for AlCl 3 /HCl.…”

Section: Hydrolysis and Dehydration In A Biphasic Systemmentioning

confidence: 99%

“…20 In our previous work, a THF/NaCl aq biphasic system was applied in the catalytic dehydration of water-soluble carbohydrates using a combination of Lewis and Brønsted acids. 21 AlCl 3 /HCl was best for glucose dehydration while ZnCl 2 /HCl gave higher HMF yields from sucrose and sugarcane molasses. Compared to synthetic mixtures containing the same amount of sugars, no matrix interference was observed during dehydration of sugarcane molasses.…”

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Production of Furan Compounds from Sugarcane Bagasse Using a Catalytic System Containing ZnCl2/HCl or AlCl3/HCl in a Biphasic System

Gomes¹,

Rampon²,

Ramos³

2018

J. Braz. Chem. Soc.

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In this work, two catalytic systems combining Lewis and Brønsted acids (ZnCl 2 /HCl and AlCl 3 /HCl) were applied in a tetrahydrofuran (THF)/NaCl aq biphasic system to produce furan compounds from plant polysaccharides. The following cellulosic matrices were applied for this purpose: α-cellulose, microcrystalline cellulose and both native and steam-exploded sugarcane bagasse. The AlCl 3 /HCl catalytic system afforded the best yields for α-cellulose conversion to furan compounds (hydrolysis followed by dehydration). The highest yields of 5-(hydroxymethyl)-furfural (HMF) and furfural were 44.0 and 92.2% for AlCl 3 /HCl and 36.5 and 81.4% for ZnCl 2 /HCl, respectively. Cellulosic materials with lower crystallinity indexes afforded the best performance in hydrolysis followed by dehydration, giving relatively high yields of HMF and furfural. The HMF yields were similar for both native and steam-exploded sugarcane bagasse and the presence of lignin had a negative effect on HMF production. The highest furfural yield from native sugarcane bagasse was 60.6% with AlCl 3 /HCl catalytic system. Keywords: acid-catalyzed dehydration, furans, cellulose, sugarcane bagasse, crystallinity IntroductionThe integral use of renewable feedstocks for fuels and chemicals is the key for the development of sustainable biorefineries. The International Energy Agency (IEA) defines biorefinery as the sustainable processing of biomass into a spectrum of products to be marketed as food, chemicals and supplies. In another definition, the American National Renewable Energy Laboratory (NREL) describes biorefinery as a facility that integrates equipment and processes for biomass conversion into fuels, energy and chemicals for industry. 1,2Sugarcane bagasse is an important agro-industrial byproduct for biorefining because large amounts are readily available at low cost in sugarcane-processing industrial facilities such as autonomous distilleries and sugar mills. Sugarcane bagasse is majorly composed of glucans (mostly cellulose), hemicelluloses (mostly xylans) and lignin and these macromolecular components are involved in a strong chemical association that reduces its accessibility to chemical conversion. 4 Different forms of pretreatment can break this strong association and increase the chemical accessibility of cane bagasse polysaccharides. One of the most interesting pretreatment technique is steam explosion, which combines chemical and physical processes to deconstruct the plant cell wall associative structure. 5,6 For this, the biomass is treated with saturated steam at temperatures between 170-230 °C for 2 to 30 min in the absence or presence of an exogenous catalyst. 7 The main feature of steam explosion is the total or partial acid hydrolysis of hemicelluloses to produce mono and oligosaccharides, which are intermediate chemicals for a variety of value-added products. In addition, changes in the lignin structure occur primarily due to the acid hydrolysis of aril-ether linkages, while both xylan and glucan degree of polymerization is decreas...

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Hydrolysis and Dehydration In A Biphasic Systemmentioning

confidence: 99%

mentioning

confidence: 99%

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Production of Furan Compounds from Sugarcane Bagasse Using a Catalytic System Containing ZnCl2/HCl or AlCl3/HCl in a Biphasic System

Gomes¹,

Rampon²,

Ramos³

2018

J. Braz. Chem. Soc.

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“…As far as the source of biomass is concerned, sugarcane is one of the most economically viable cultures for biorefinery applications and accounts for nearly 75% of the global sugar production . The main byproduct of sugar production is molasses from the sucrose crystallization process in the concentrated sugarcane juice . It is a low-cost feedstock that has a high concentration of carbohydrates, containing about 52% reducing sugars, mainly sucrose .…”

Section: Introductionmentioning

confidence: 99%

Ash Influence on the Ethyl Levulinate Production from Sugarcane Molasses Mediated by Taurine Hydrogen Sulfate

Gomes

Breitkreitz

Pastre

2021

ACS Sustainable Chem. Eng.

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Ethyl levulinate (EL) is an important biobased building block obtained from a sugar platform to produce chemicals, pharmaceuticals, solvents, plasticizers, and biofuels. In this work, a biobased amino acid derivative, taurine hydrogen sulfate, was applied as a Brønsted-acid catalyst for the conversion of sugarcane molasses to ethyl levulinate under microwave irradiation. Experimental designs were carried out for the three main carbohydrates present in the molasses (fructose, sucrose, and glucose), and under the optimized conditions, EL was obtained in 76% yield from fructose (180 °C, 60 min, Cat. 5 mol %), 54% yield from sucrose (180 °C, 60 min, Cat. 40 mol %), and 53% yield from glucose (180 °C, 120 min, Cat. 100 mol %). A control experiment using a synthetic medium showed that EL could be obtained in up to 80% yield at 180 °C for 2 h with 100 mol % taurine hydrogen sulfate. However, EL yields were extremely low (5%) at the same conditions using the raw feedstock, the drop in the yield correlating with the inorganic matter (ashes) content of the molasses. Several adsorbents were tested, and Dowex 50WX2 exhibited the best performance to remove the ash content. Indeed, two sequential percolations could reduce the ashes from 7.5% to 0.25%, resulting in a matrix able to produce EL in 82% yield, completely eliminating the matrix effect observed for sugarcane molasses. Our findings could be useful for other applications including the use of this abundant raw material for the preparation of other key industrial intermediates.

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Sn doping on partially dealuminated Beta zeolite by solid state ion exchange for 5‐hydroxymethylfurfural (5‐HMF) production from glucose

Zhang

Shen

Kong

et al. 2022

J of Chemical Tech & Biotech

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BACKGROUND: The conversion of glucose into 5-hydroxymethylfurfural (5-HMF) involves the isomerization of glucose to fructose catalyzed by Lewis acid and subsequent dehydration of fructose catalyzed by Brönsted acid. In this work, in order to obtain a high yield of 5-HMF, a series of Sn-Al-Beta catalysts containing both Lewis and Brönsted acid sites were prepared by a convenient solid state ion exchange (SSIE) method using partially dealuminated Beta zeolite and tin(II) acetate. RESULTS:The obtained bifunctional catalysts were investigated for one-pot production of 5-HMF from glucose in the ionic liquid (IL) [C 4 mim]Cl. Among various catalysts, Sn-Al-Beta-4-8 exhibited the best catalytic performance, giving a 5-HMF yield of 54% under optimal reaction conditions (393 K, 2 h), along with a glucose conversion of 81%. The Sn-Al-Beta-4-8 catalyst and IL were regenerated by the extraction of 5-HMF, and the reactivity was reserved after five runs of recycling. In addition to glucose, the Sn-Al-Beta-4-8/[C 4 mim]Cl system was also proven to have the potential to effectively convert other carbohydrates into 5-HMF. CONCLUSION:The results suggested that the catalyst is convenient to prepare and has preferable efficiency and stability in the conversion of carbohydrates into 5-HMF.

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Production of 5-(hydroxymethyl)-furfural from water-soluble carbohydrates and sugarcane molasses

Cited by 23 publications

References 40 publications

Production of Furan Compounds from Sugarcane Bagasse Using a Catalytic System Containing ZnCl2/HCl or AlCl3/HCl in a Biphasic System

Production of Furan Compounds from Sugarcane Bagasse Using a Catalytic System Containing ZnCl2/HCl or AlCl3/HCl in a Biphasic System

Ash Influence on the Ethyl Levulinate Production from Sugarcane Molasses Mediated by Taurine Hydrogen Sulfate

Sn doping on partially dealuminated Beta zeolite by solid state ion exchange for 5‐hydroxymethylfurfural (5‐HMF) production from glucose

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