Production of tetrahydrofuran by dehydration of 1,4-butanediol using Amberlyst-15: Batch kinetics and batch reactive distillation

Shinde, V. M.; Patil, Ganesh N.; Katariya, Amit; Mahajan, Yogesh S.

doi:10.1016/j.cep.2015.06.016

Cited by 36 publications

(15 citation statements)

References 20 publications

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“…This low score is the same as that for tetrahydrofuran, which is a solvent with a molecular structure very similar to that of 2-MeTHF. However, tetrahydrofuran is industrially produced from fossil resources via the dehydration of 1,4-butanediol . On the other hand, 2-MeTHF is easily obtained from renewable resources via the hydrogenation of furfural at a viable cost if produced in large quantities .…”

Section: Resultsmentioning

confidence: 99%

“…However, tetrahydrofuran is industrially produced from fossil resources via the dehydration of 1,4-butanediol. 58 On the other hand, 2-MeTHF is easily obtained from renewable resources via the hydrogenation of furfural at a viable cost if produced in large quantities. 19 In view of its renewable origin, another solvent selection guide favors the use of 2-MeTHF.…”

Section: Resultsmentioning

confidence: 99%

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Process Design and Technoeconomic Assessment of the Extraction of Levulinic Acid from Biomass Hydrolysate Using n-Butyl Acetate, Hexane, and 2-Methyltetrahydrofuran

Silva

Filho

Maciel

2020

Ind. Eng. Chem. Res.

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Levulinic acid, a chemical produced during the hydrolysis of biomass, has various applications in the chemical and fuel markets that are unexplored because of several problems related to its large-scale production. Recovery of levulinic acid is challenging because of its low volatility, the presence of other chemicals in the biomass hydrolysate, and the desire to recycle the catalyst. In this work, the recovery cost of levulinic acid from biomass hydrolysate was evaluated and optimized in a complete recovery process, including the evaporation of hydrolysate, extraction, and solvent recycling. Three solvents with different classifications in solvent selection guides were considered: n-butyl acetate, hexane, and 2-methyltetrahydrofuran. In the optimized scenarios, the recovery cost using 2-methyltetrahydrofuran was $0.156 kg −1 (17% lower than that of n-butyl acetate and 32% lower than that of hexane). The simulation results, based on a group contribution method, present a methodology suitable for the early-stage assessment of separation processes to recover renewable chemicals in biorefineries.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Process Design and Technoeconomic Assessment of the Extraction of Levulinic Acid from Biomass Hydrolysate Using n-Butyl Acetate, Hexane, and 2-Methyltetrahydrofuran

Silva

Filho

Maciel

2020

Ind. Eng. Chem. Res.

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“…The high solubility of these adducts in these solvents was previously observed by Hronec et al ., proposing the use of methanol or tetrahydrofuran . Nevertheless, both solvents are considered as toxic and incompatible with Green Chemistry principles …”

Section: Introductionmentioning

confidence: 99%

“…13 Nevertheless, both solvents are considered as toxic and incompatible with Green Chemistry principles. 19,20 Taking into account that alcohols and organic esters dissolve the condensation adducts, 21 ethanol and ethyl acetate are proposed as valuable alternatives. Ethyl acetate is considered as a green solvent (low toxicity, stable, biodegradable, etc.)…”

Section: Introductionmentioning

confidence: 99%

Enhancement of furfural–cyclopentanone aldol condensation using binary water–ethanol mixtures as solvent

Cueto

Faba

Dı́az

et al. 2018

J of Chemical Tech & Biotech

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BACKGROUND Cyclopentanone (CPO) – furfural (FFL) aldol condensation is a very interesting reaction for upgrading the furfural obtained in the depolymerization – dehydration reaction of cellulosic materials. Reaction is faster with cyclopentanone than with other ketones, and resulting condensation adducts are attractive for manufacturing drop‐in fuels. However, the most important problem is that these adducts present low water solubility. RESULTS Binary systems combining water (needed to promote aldol condensation) and ethanol (for enhancing the condensation adducts solubility) at different ratios have been tested. Operation parameters, such as water/ethanol ratio, temperature and reaction time, were optimized for this reaction. Best results (global yield to condensation adducts higher than 36%) were achieved using 1:2 water/ethanol ratio, and working at 303 K. Higher water ratios lead to the precipitation of condensation products, whereas higher ethanol concentrations hinder the catalyst performance. A reaction mechanism, considering a first‐order kinetic model on cyclopentanone concentration, was proposed. Kinetic constants have been empirically correlated with ethanol concentration in the reaction medium. CONCLUSIONS The use of binary ethanol–water binary mixtures with controlled solvent ratios can avoid the precipitation of condensation adducts. This precipitation leads to important operation problems in the reactor as well as to catalyst deactivation. The negative effect of the presence of ethanol on the reaction kinetics can be overcome by increasing reaction temperature. © 2017 Society of Chemical Industry

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“…One commercial THF production method is based on a well-known technology that uses strongly inorganic acids as catalysts for cyclodehydration of butane-1,4-diol [22 -27]. Recent advances in the synthesis of substituted THF rings have been achieved using different synthetic methods with novel catalysts and alternative starting materials [28][29][30][31][32][33]. Additionally, reports of cyclodehydration of 1,n-diols to cyclic ethers have been published; this is essentially a dehydration reaction between two hydroxy groups to yield an ether (figure 1 ref.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of cyclic ethers by cyclodehydration of 1, n -diols using heteropoly acids as catalysts

Sun¹,

Huang²,

Li³

et al. 2018

R. Soc. open sci.

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Heteropoly acids were used as catalysts for cyclodehydration of various 1,n-diols. Cyclodehydration of butane-1,4-diol, pentane-1,5-diol and hexane-1,6-diol catalysed by H3PW12O40 gave tetrahydrofuran, tetrahydropyran and oxepane, respectively. Cyclodehydration of diethylene glycol, triethylene glycol, diethylene glycol monomethyl ether and polyethylene glycol 200 catalysed by H3PW12O40 gave 1,4-dioxane. In particular, cyclodehydration of hexane-1,6-diol gave an excellent yield of oxepane (80%). The selectivity exhibited by the H3PW12O40 catalyst was even better than that exhibited by other reported catalyst systems for similar cyclodehydration reactions.

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Production of tetrahydrofuran by dehydration of 1,4-butanediol using Amberlyst-15: Batch kinetics and batch reactive distillation

Cited by 36 publications

References 20 publications

Process Design and Technoeconomic Assessment of the Extraction of Levulinic Acid from Biomass Hydrolysate Using n-Butyl Acetate, Hexane, and 2-Methyltetrahydrofuran

Process Design and Technoeconomic Assessment of the Extraction of Levulinic Acid from Biomass Hydrolysate Using n-Butyl Acetate, Hexane, and 2-Methyltetrahydrofuran

Enhancement of furfural–cyclopentanone aldol condensation using binary water–ethanol mixtures as solvent

Synthesis of cyclic ethers by cyclodehydration of 1, n -diols using heteropoly acids as catalysts

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