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Catalytic Conversion of Glycerol

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A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Biomass Catalysis".

Deadline for manuscript submissions: closed (10 December 2022) | Viewed by 46934

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Special Issue Editors

Prof. Dr. Charles Xu

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Guest Editor

School of Energy and Environment, City University of Hong Kong, Kowloon, Hong Kong, China
Interests: catalytic conversion of lignocellulosic biomass for fuels; chemicals and materials; catalytic conversion of cellulose, starch or sugars into chemicals and materials; catalytic conversion of glycerol; green chemistry and engineering
Special Issues, Collections and Topics in MDPI journals

Dr. Tianliang Lu

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Guest Editor

School of Chemical Engineering, Zhengzhou University, Zhengzhou 450001, China
Interests: design of nano metal catalysts; heterogeneous catalytic selective oxidation; green synthesis of biomass-based fine chemicals from glycerol
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Glycerol is the core byproduct in the production of biodiesel. Recently, with the booming of the biodiesel industry, a huge amount of glycerol has been generated. Value-added applications of glycerol, e.g., as a low-cost raw material for chemicals and fuels, has attracted increasing attention. Due to the highly functionalized molecular structure of glycerol, it can be catalytically converted into many high-value chemicals/fuels including: citric acid, lactic acid, 1,3-dihydroxyacetone, 1,3-propanediol, 1,2-propanediol, dichloro-2-propanol, acrolein, solketal, hydrogen, ethanol, etc. To realize efficient and cost-effective production of these chemicals/fuels from glycerol, the development of proper heterogeneous catalysts or biocatalysts, and catalytic processes is essential. According to the target products, catalytic strategies for glycerol conversion can be classified into oxidation, dehydration, acetylation, esterification, reforming, reduction, etherification, ammoxidation, acetalization, gasification, etc. This Special Issue welcomes both review and original research articles on all aspects of glycerol conversion/utilization by catalysis in both heterogeneous and homogeneous systems. The potential topics include but are not limited to:

Catalytic oxidation of glycerol;
Catalytic dehydration of glycerol;
Catalytic reduction of glycerol;
Catalytic acetylation of glycerol;
Catalytic esterification of glycerol;
Catalytic reforming of glycerol;
Catalytic etherification, ammoxidation or acetalization of glycerol;
Photo-catalytic or electrocatalytic conversion of glycerol;
Catalytic gasification of glycerol into hydrogen or syngas.

Prof. Dr. Charles Xu
Prof. Dr. Tianliang Lu
Guest Editors

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Keywords

Glycerol conversion
Chemicals and fuels
Catalytic oxidation
Catalytic dehydration
Catalytic reduction
Catalytic acetylation
Catalytic esterification
Catalytic reforming
Catalytic etherification
Catalytic ammoxidation
Catalytic acetalization
Photo-catalytic conversion
Electrocatalytic conversion
Catalytic gasification.

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Published Papers (14 papers)

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Editorial

Jump to: Research, Review

3 pages, 175 KiB

Open AccessEditorial

New Trends in Catalytic Conversion of Glycerol

by Tianliang Lu and Chunbao Charles Xu

Catalysts 2023, 13(4), 701; https://doi.org/10.3390/catal13040701 - 4 Apr 2023

Cited by 1 | Viewed by 1614

Abstract

Glycerol is the core byproduct in the production of biodiesel [...] Full article

(This article belongs to the Special Issue Catalytic Conversion of Glycerol)

Research

Jump to: Editorial, Review

23 pages, 3869 KiB

Open AccessArticle

Aqueous-Phase Glycerol Conversion over Ni-Based Catalysts Synthesized by Nanocasting

by Adriana Morales-Marín, Unai Iriarte-Velasco, Miguel Ángel Gutiérrez-Ortiz and Jose Luis Ayastuy

Catalysts 2022, 12(6), 668; https://doi.org/10.3390/catal12060668 - 18 Jun 2022

Cited by 2 | Viewed by 2175

Abstract

A morphological strategy consisting of nanocasting synthesis of nickel aluminate spinel precursor was addressed. Two nanocasted catalysts were synthesized involving different template-removal procedures (i.e., Teflon-assisted calcination vs. NaOH washing) for spinel recovery. As a reference, spinel NiAl₂O₄ supported by SBA-15 and bare nickel aluminate spinel were selected. The obtained solids were characterized in detail, examining their textural, acid–base, structural and compositional characteristics, either in the calcined or reduced forms. The as-obtained catalysts’ performance was evaluated in the aqueous-phase reforming of glycerol at 235 °C and 35 bar. Exhausted samples were also characterized to enlighten changes in catalyst properties during the aqueous-phase reaction. NiAl/SBA-15 and NiAl-NCF catalyst showed very poor catalytic performance for the glycerol transformation. NiAl-NCN catalyst presented improved activity with respect to NiAl, with a 20% higher hydrogen production rate but, as a drawback, higher methane formation for a whole range of glycerol conversions. Exhausted catalyst indicated nickel oxidized in liquid phase reaction. Full article

(This article belongs to the Special Issue Catalytic Conversion of Glycerol)

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16 pages, 5169 KiB

Open AccessArticle

The Inorganic Perovskite-Catalyzed Transfer Hydrogenation of Cinnamaldehyde Using Glycerol as a Hydrogen Donor

by Tafadzwa Precious Mabate, Reinout Meijboom and Ndzondelelo Bingwa

Catalysts 2022, 12(2), 241; https://doi.org/10.3390/catal12020241 - 21 Feb 2022

Cited by 9 | Viewed by 2628

Abstract

Catalytic transfer hydrogenation reactions (CTHs) produce value-added chemicals in the most economical, safe, green, and sustainable way. However, understanding the reaction mechanism and developing stable, selective, and cheap catalysts has been a significant challenge. Herein, we report on the hydrogenation of cinnamaldehyde utilizing glycerol as a hydrogen donor and metal-oxides (SnO₂, LaFeO₃, and LaSnO₃) as heterogeneous catalysts. The perovskite types were used because they are easy to synthesize, the metal components are readily available, and they are good alternatives to noble metals. The catalysts were synthesized through the nanocasting (hard-template) method with SiO₂ (KIT-6) as a template. The template was synthesized using the soft-template (sol-gel) method resulting in a high surface area of 624 m²/g. Furthermore, catalytic evaluations gave high cinnamaldehyde percentage conversions of up to 99%. Interestingly, these catalysts were also found to catalyze the etherification of glycerol in one pot. Therefore, we propose competitive surface catalytic reactions driven by the transition metal cations as the binding sites for the cinnamaldehyde and the sacrificial glycerol. Full article

(This article belongs to the Special Issue Catalytic Conversion of Glycerol)

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10 pages, 1329 KiB

Open AccessArticle

Tuning the Catalytic Activity of Recyclable Heterogeneous Catalysts for the Direct Etherification Reaction of Glycerol Using Antagonistic Additives

by Je Seung Lee, Eunji Jang, Dae Won Kim and Seo Kyung Park

Catalysts 2022, 12(2), 220; https://doi.org/10.3390/catal12020220 - 15 Feb 2022

Cited by 2 | Viewed by 2353

Abstract

Using zeolite as a heterogeneous catalyst, the reaction conditions were optimized to increase the yield and selectivity of diglycerol (DG) and triglycerol (TG) in the direct etherification reaction of glycerol. By the addition of weakly acidic alkali metal-based inorganic salts (NaHSO₄ and KHSO₄), the selectivities and yields of DG and TG increased. Although the conversion of glycerol was lowered due to the role of the additive as an inhibitor, the reaction conditions were optimized by controlling the amounts and reaction times of the additives to increase the yields of DG and TG. Under the optimized condition, the glycerol conversion was as high as 85.4%, and the highest yields of DG and TG were observed as 54.1% and 21.3%, respectively. The recyclability of the catalysts was much enhanced by the influence of the additives suppressing the formation of oligomers. Full article

(This article belongs to the Special Issue Catalytic Conversion of Glycerol)

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29 pages, 3417 KiB

Open AccessFeature PaperArticle

Mechanistic Kinetic Modelling Framework for the Conversion of Waste Crude Glycerol to Value-Added Hydrogen-Rich Gas

by Anita Odoom, Michael Fabrik, Amgad Salama, Ezeddin Shirif and Hussameldin Ibrahim

Catalysts 2022, 12(2), 200; https://doi.org/10.3390/catal12020200 - 7 Feb 2022

Cited by 3 | Viewed by 3037

Abstract

The kinetics for crude glycerol autothermal reforming was studied over S/C ratio of 2.6 and O₂/C ratio of 0.125 using 5% Ni/CeZrCa catalyst. Both power law and mechanistic kinetic models were studied. The overall power law model for crude glycerol autothermal reforming was investigated with a pre-exponential factor of 4.3 × 10¹⁰ mol/g_cat·min and activation energy of 8.78 × 10⁴ J/mol. The reaction orders with respect to crude glycerol, water and oxygen are 1.04, 0.54 and 1.78 respectively. The power law model presented an absolute average deviation of 5.84%, which showed a good correlation between the predicted and experimental rate. Mechanistic models were developed for crude glycerol autothermal reforming. For steam reforming, the Eley–Rideal approach best described the reaction rate with the surface reaction being the rate-determining step (AAD < 10%). The kinetics of the total oxidation reaction was best described by the power law model with an AAD of less than 1%, whereas for the TOR process, the molecular adsorption of crude glycerol with an AAD of 14.6% via Langmuir Hinshelwood Hougen-Watson approach was best. CO₂ methanation resulted in an AAD of 5.8% for the adsorption of carbon dioxide (CO₂) by the Eley–Rideal mechanism. Full article

(This article belongs to the Special Issue Catalytic Conversion of Glycerol)

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15 pages, 2790 KiB

Open AccessFeature PaperArticle

Catalytic Conversion of Glycerol to Methyl Lactate over Au-CuO/Sn-Beta: The Roles of Sn-Beta

by Ying Duan, Qianqian Luo, Renfeng Nie, Jianshe Wang, Yongsheng Zhang, Tianliang Lu and Chunbao Xu

Catalysts 2022, 12(1), 104; https://doi.org/10.3390/catal12010104 - 17 Jan 2022

Cited by 6 | Viewed by 2789

Abstract

The production of methyl lactate as a degradable polymer monomer from biomass was an important topic for a sustainable society. In this manuscript, glycerol was oxidated to methyl lactate catalyzed by the combination of Au-CuO and Sn-Beta. The influence of Sn content, Sn source, and the preparation conditions for Sn-β was studied. The Au content in Au/CuO was also investigated by varying the Au content in Au/CuO. The catalysts were characterized by XRD, FTIR spectroscopy of pyridine adsorption, and TEM to study the role of Sn and the influence of different parameters for catalyst preparation. After the optimization of reaction parameters, the yield of methyl lactate from glycerol reached 59% at 363 K after reacting in 1.6 MPa of O₂ for 6 h. Full article

(This article belongs to the Special Issue Catalytic Conversion of Glycerol)

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12 pages, 3585 KiB

Open AccessArticle

Acetalization of Glycerol with Citral over Heteropolyacids Immobilized on KIT-6

by José Castanheiro

Catalysts 2022, 12(1), 81; https://doi.org/10.3390/catal12010081 - 12 Jan 2022

Cited by 7 | Viewed by 2297

Abstract

Glycerol acetalization with citral was studied using a heteropolyacid (tungstophosphoric acid) supported on KIT-6, as a catalyst, at 100 °C. Different catalysts were synthesized. Catalysts were characterized by scanning electron microscopy (SEM), inductively coupled plasma (ICP), X-ray diffraction (XRD), attenuated total refletion-Fourier transform infrared spectroscopy (ATR-FTIR), and potentiometric titrations. At a fixed time, the glycerol conversion increased with the H₃PW₁₂O₄₀ (PW) on KIT-6. PW4-KIT-6 material had a higher conversion than other catalysts. The optimization of glycerol’s acetalization with citral was studied under the PW4-KIT-6 catalyst. After 5 h, it was found that, at T = 100 °C, with m = 0.3 g of solid, molar glycerol:citral = 1:2.25, the conversion of glycerol was 89%. Moreover, the PW4-KTI-6 catalyst showed good catalytic stability. Full article

(This article belongs to the Special Issue Catalytic Conversion of Glycerol)

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11 pages, 2692 KiB

Open AccessArticle

Catalytic Prebiotic Formation of Glycerol Phosphate Esters and an Estimation of Their Steady State Abundance under Plausible Early Earth Conditions

by Maheen Gull and Matthew A. Pasek

Catalysts 2021, 11(11), 1384; https://doi.org/10.3390/catal11111384 - 17 Nov 2021

Cited by 5 | Viewed by 3051

Abstract

The emergence of biological phosphate esters of glycerol could have been a crucial step in the origin and evolution of life on the early Earth as glycerol phosphates today play a central role in biochemistry. We investigate here the formation of the glycerol phosphates by employing various rock samples, salts, and minerals as potential catalysts to aid the phosphorylation process. We report the synthesis of various phosphate esters of glycerol including glycerol-1-phosphate, glycerol-2-phosphate, cyclic glycerol-monophosphate as well as various diphosphate esters. Furthermore, the decomposition rates of glycerol phosphate under mild heating were also studied while keeping the pH constant. It was observed that glycerol phosphate starts decomposing quickly under mild heating conditions into inorganic orthophosphate and pyrophosphate, and a steady state concentration of ~0.5 M of glycerol phosphate may have been reasonable in ponds with abundant glycerol, phosphate, urea, and catalytic minerals. Full article

(This article belongs to the Special Issue Catalytic Conversion of Glycerol)

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12 pages, 1665 KiB

Open AccessArticle

Direct Etherification Reaction of Glycerol Using Alkali Metal Cation (Li⁺, Na⁺ and K⁺) Containing X-Type Zeolites as Heterogeneous Catalysts: Optimization of the Reaction Conditions

by Seo Kyung Park, Dae Won Kim, Su Yeon Lee and Je Seung Lee

Catalysts 2021, 11(11), 1323; https://doi.org/10.3390/catal11111323 - 30 Oct 2021

Cited by 7 | Viewed by 2022

Abstract

X-type zeolite (XZ-Na) containing Na⁺ as a cation was synthesized, and XZ-Li and XZ-K were prepared by exchanging the cations of XZ-Na with Li⁺ and K⁺, respectively. The specific surface areas, structures, and chemical compositions of the prepared zeolites were analyzed by BET, XRD, and SEM-EDX. The activity of the direct and selective etherifications of glycerol to diglycerol (DG) and triglycerol (TG) were investigated using each zeolite XZ-M (M = Li, Na or K) as a basic heterogeneous catalyst. The etherification reactions of glycerol were carried out at atmospheric pressure while controlling the reaction temperature, reaction time, and the amount of each zeolite. As the amount of each zeolite, reaction time, and reaction temperature increased, the conversion of glycerol also increased, but the selectivities of DG and TG decreased due to the increase in the production of oligomers. When each zeolite was used as a catalyst, the catalytic activity for the conversion of glycerol was observed as XZ-K > XZ-Li > XZ-Na, but the selectivities of DG and TG were observed as XZ-Li > XZ-Na > XZ-K. Especially, 3 wt.% of XZ-Li exhibited the excellent catalytic performance when the etherification of glycerol was optimized and carried out at 280 °C for 2 h: the conversion of glycerol was 89.6% and the yields of DG and TG were 61.2 and 21.2%, respectively. Full article

(This article belongs to the Special Issue Catalytic Conversion of Glycerol)

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31 pages, 7306 KiB

Open AccessFeature PaperArticle

Glycerol Hydrogenolysis to Produce 1,2-Propanediol in Absence of Molecular Hydrogen Using a Pd Promoted Cu/MgO/Al₂O₃ Catalyst

by Yuanqing Liu, Michael Wu, Garry L. Rempel and Flora T.T. Ng

Catalysts 2021, 11(11), 1299; https://doi.org/10.3390/catal11111299 - 28 Oct 2021

Cited by 6 | Viewed by 2850

Abstract

The catalytic process of glycerol hydrogenolysis to produce 1,2-propandiol (1,2-PD) in the absence of external hydrogen addition has been investigated. The methanol present in the crude glycerol from a biodiesel production process is used to provide in situ hydrogen produced via methanol steam reforming for the glycerol hydrogenolysis process. This process can reduce the additional cost for the transportation and storage of molecular hydrogen and also reduce the safety risks related to using high hydrogen pressure. It was found that the introduction of Pd onto a Cu/MgO/Al₂O₃ catalyst significantly improved the glycerol conversion and 1,2-PD selectivity. The pseudo-first-order kinetic results suggested that the promoting effect of Pd is primarily attributed to the enhanced activity for the hydrogenation of acetol, which is the intermediate formed via glycerol dehydration. A 2⁷⁻³ fractional factorial design experiment was carried out to investigate the impacts of seven single factors and their binary effects on two responses, namely 1,2-PD selectivity and glycerol conversion. The results showed that the glycerol feed concentration has the most significant effect on the 1,2-PD selectivity, such that the 1,2-PD selectivity is lower if a more concentrated glycerol is used as the feedstock; stirring speed, inert gas pressure and water to methanol molar ratio have insignificant effects on the reaction system. The addition of Pd, higher temperature and higher catalyst loading are the essential factors in order to obtain a high selectivity of 1,2-PD and a high glycerol conversion. Full article

(This article belongs to the Special Issue Catalytic Conversion of Glycerol)

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9 pages, 2329 KiB

Open AccessArticle

Positive Effect of Antagonistic Additives on the Homogeneous Catalytic Etherification Reaction of Glycerol

by Taeyoul Han and Je Seung Lee

Catalysts 2021, 11(8), 1000; https://doi.org/10.3390/catal11081000 - 19 Aug 2021

Cited by 4 | Viewed by 2028

Abstract

Various compounds prepared using glycerol, diglycerol (DG), and triglycerol (TG) have been gaining increasing attention due to their wide range of applications. To increase the yield and selectivity of DG and TG syntheses, previous studies investigated a variety of catalysts with different basicity and variable reaction temperatures. In this study, we introduced additives that act as inhibitors to increase the selectivity of the etherification reaction for DG and TG production and depress the formation of higher oligomers by moderating the activity of the catalyst. By adding weakly acidic alkali metal-based inorganic salts (NaHSO₄ and KHSO₄), the selectivity of DG and TG formation could be enhanced, although the conversion of glycerol decreased due to the reduced activity of catalyst. We found that the decrease in the activity of the catalyst caused by the additives could be recovered and that side reactions were reduced if the reaction was carried out at an increased temperature of 280 °C and if the reaction time was shortened to 2 h to suppress the formation of oligomers. The dependence of the reaction on the amount of the additive, the reaction time, and the reaction temperature was investigated to elucidate the role of the additive. Full article

(This article belongs to the Special Issue Catalytic Conversion of Glycerol)

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Review

Jump to: Editorial, Research

30 pages, 6495 KiB

Open AccessReview

Critical Review of the Various Reaction Mechanisms for Glycerol Etherification

by Prakas Palanychamy, Steven Lim, Yeow Hong Yap and Loong Kong Leong

Catalysts 2022, 12(11), 1487; https://doi.org/10.3390/catal12111487 - 21 Nov 2022

Cited by 15 | Viewed by 6835

Abstract

This review provides in-depth coverage of numerous mechanisms available for the etherification process of glycerol, including alcohol solvent, olefin solvent and solvent-free routes along with products that are formed at various stages of the reaction. Mono tert-butyl glycerol ether (MTBG), di tert-butyl glycerol ether (DTBG), and tri tert-butyl glycerol ether (TTBG) are the three general ether compounds obtained through tert-butyl alcohol (TBA) etherification. Glycerol etherification with n-butanol results in the formation of glycerol ether products that are linked to the substituted butyl groups. These products include two mono-butyl glycerol ethers, two di-butyl glycerol ethers and a tri-butyl glycerol ether. Two mono-benzyl glycerol ether isomers, two di-benzyl glycerol ether isomers and tri-benzyl glycerol ether are the most reported results when benzyl alcohol is used as a solvent in the etherification reaction. The etherification of glycerol with 1-butene involves a series of equilibrium reactions to produce mono-ethers, di-ethers, and tri-ethers, whereas the etherification of glycerol with isobutene is carried out via tert-butylation of glycerol, yielding similar glycerol ether products when TBA is used as a solvent. As the by-product may be easily removed, the solvent-free glycerol etherification approach may have several advantages over the other conventional methods. Therefore, further studies on base-catalyzed glycerol etherification that employs a solvent-free reaction route may reveal a method for improving the conversion, selectivity, and yield of reaction products. This review study is crucial in improving knowledge of numerous mechanisms and how they relate to the effectiveness of the product’s catalytic process. Full article

(This article belongs to the Special Issue Catalytic Conversion of Glycerol)

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28 pages, 1244 KiB

Open AccessReview

Chemicals Production from Glycerol through Heterogeneous Catalysis: A Review

by Parvaneh Koranian, Qian Huang, Ajay Kumar Dalai and Ramaswami Sammynaiken

Catalysts 2022, 12(8), 897; https://doi.org/10.3390/catal12080897 - 15 Aug 2022

Cited by 30 | Viewed by 6044

Abstract

Utilization of biofuels generated from renewable sources has attracted broad attention due to their benefits such as reducing consumption of fossil fuels, sustainability, and consequently prevention of global warming. The production of biodiesel causes a huge amount of by-product, crude glycerol, to accumulate. Glycerol, because of its unique structure having three hydroxyl groups, can be converted to a variety of industrially valuable products. In recent decades, increasing studies have been carried out on different catalytic pathways to selectively produce a wide range of glycerol derivatives. In the current review, the main routes including carboxylation, oxidation, etherification, hydrogenolysis, esterification, and dehydration to convert glycerol to value-added products are investigated. In order to achieve more glycerol conversion and higher desired product selectivity, acquisition of knowledge on the catalysts, the type of acidic or basic, the supports, and studying various reaction pathways and operating parameters are necessary. This review attempts to summarize the knowledge of catalytic reactions and mechanisms leading to value-added derivatives of glycerol. Additionally, the application of main products from glycerol are discussed. In addition, an overview on the market of glycerol, its properties, applications, and prospects is presented. Full article

(This article belongs to the Special Issue Catalytic Conversion of Glycerol)

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32 pages, 2871 KiB

Open AccessFeature PaperReview

Catalytic Conversion of Glycerol into Hydrogen and Value-Added Chemicals: Recent Research Advances

by Yulin Hu, Quan He and Chunbao Xu

Catalysts 2021, 11(12), 1455; https://doi.org/10.3390/catal11121455 - 29 Nov 2021

Cited by 21 | Viewed by 4954

Abstract

In recent decades, the use of biomass as alternative resources to produce renewable and sustainable biofuels such as biodiesel has gained attention given the situation of the progressive exhaustion of easily accessible fossil fuels, increasing environmental concerns, and a dramatically growing global population. The conventional transesterification of edible, nonedible, or waste cooking oils to produce biodiesel is always accompanied by the formation of glycerol as the by-product. Undeniably, it is essential to economically use this by-product to produce a range of valuable fuels and chemicals to ensure the sustainability of the transesterification process. Therefore, recently, glycerol has been used as a feedstock for the production of value-added H₂ and chemicals. In this review, the recent advances in the catalytic conversion of glycerol to H₂ and high-value chemicals are thoroughly discussed. Specifically, the activity, stability, and recyclability of the catalysts used in the steam reforming of glycerol for H₂ production are covered. In addition, the behavior and performance of heterogeneous catalysts in terms of the roles of active metal and support toward the formation of acrolein, lactic acid, 1,3-propanediol, and 1,2-propanediol from glycerol are reviewed. Recommendations for future research and main conclusions are provided. Overall, this review offers guidance and directions for the sufficient and economical utilization of glycerol to generate fuels and high value chemicals, which will ultimately benefit industry, environment, and economy. Full article

(This article belongs to the Special Issue Catalytic Conversion of Glycerol)

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