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Article

Heterogeneously Catalyzed γ-Valerolactone Hydrogenation into 1,4-Pentanediol in Milder Reaction Conditions

by
Irina Simakova
1,2,*,
Yulia Demidova
1,2,
Mikhail Simonov
1,2,
Sergey Prikhod’ko
1,2,
Prashant Niphadkar
3,
Vijay Bokade
3,
Paresh Dhepe
3 and
Dmitry Yu. Murzin
4,*
1
Boreskov Institute of Catalysis, pr. Lavrentieva, 5, 630090 Novosibirsk, Russia
2
Novosibirsk State University, Pirogova 2, 630090 Novosibirsk, Russia
3
CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India
4
Johan Gadolin Process Chemistry Centre, Åbo Akademi University, Biskopsgatan 8, FI-20500 Turku/Åbo, Finland
*
Authors to whom correspondence should be addressed.
Reactions 2020, 1(2), 54-71; https://doi.org/10.3390/reactions1020006
Submission received: 20 September 2020 / Revised: 12 October 2020 / Accepted: 14 October 2020 / Published: 16 October 2020
(This article belongs to the Special Issue Mechanism and Kinetics of Complex Reactions— 2020 Selected Papers from Reactions’ Editorial Board Members)
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Abstract

Hydrogenation of γ-valerolactone (GVL) in polar solvents (n-butanol, 1,4-dioxane) to 1,4-pentanediol (PDO) and 2-methyltetrahydrofuran (MTHF) was performed at 363–443 K in a fixed bed reactor under overall H2 pressure of 0.7–1.3 MPa. Preliminary screening in a batch reactior was performed with a series of Ru, Ir, Pt, Co, and Cu catalysts, earlier efficiently applied for levulinic acid hydrogenation to GVL. The fresh catalysts were analyzed by transmission electron microscopy (TEM), X-ray fluorescent analysis (XRF), temperature programmed reduction by H2 (H2-TPR), and N2 physisorption. Cu/SiO2 prepared by reduction of copper hydroxosilicate with chrysocolla mineral structure provided better selectivity of 67% towards PDO at 32% GVL conversion in a continuous flow reactor. This catalyst was applied to study the effect of temperature, hydrogen pressure, and contact time. The main reaction products were PDO, MTHF, and traces of pentanol, while no valeric acid was observed. Activity and selectivity to PDO over Cu/SiO2 did not change over 9 h, indicating a fair resistance of copper to leaching.
Keywords: 1,4-pentanediol; γ-valerolactone; hydrogenation; biodiols; Cu; Co; Ir; Re; Pt; Ru; biomass conversion 1,4-pentanediol; γ-valerolactone; hydrogenation; biodiols; Cu; Co; Ir; Re; Pt; Ru; biomass conversion
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MDPI and ACS Style

Simakova, I.; Demidova, Y.; Simonov, M.; Prikhod’ko, S.; Niphadkar, P.; Bokade, V.; Dhepe, P.; Murzin, D.Y. Heterogeneously Catalyzed γ-Valerolactone Hydrogenation into 1,4-Pentanediol in Milder Reaction Conditions. Reactions 2020, 1, 54-71. https://doi.org/10.3390/reactions1020006

AMA Style

Simakova I, Demidova Y, Simonov M, Prikhod’ko S, Niphadkar P, Bokade V, Dhepe P, Murzin DY. Heterogeneously Catalyzed γ-Valerolactone Hydrogenation into 1,4-Pentanediol in Milder Reaction Conditions. Reactions. 2020; 1(2):54-71. https://doi.org/10.3390/reactions1020006

Chicago/Turabian Style

Simakova, Irina, Yulia Demidova, Mikhail Simonov, Sergey Prikhod’ko, Prashant Niphadkar, Vijay Bokade, Paresh Dhepe, and Dmitry Yu. Murzin. 2020. "Heterogeneously Catalyzed γ-Valerolactone Hydrogenation into 1,4-Pentanediol in Milder Reaction Conditions" Reactions 1, no. 2: 54-71. https://doi.org/10.3390/reactions1020006

APA Style

Simakova, I., Demidova, Y., Simonov, M., Prikhod’ko, S., Niphadkar, P., Bokade, V., Dhepe, P., & Murzin, D. Y. (2020). Heterogeneously Catalyzed γ-Valerolactone Hydrogenation into 1,4-Pentanediol in Milder Reaction Conditions. Reactions, 1(2), 54-71. https://doi.org/10.3390/reactions1020006

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