Hydrothermal catalytic conversion of oleic acid to heptadecane over Ni/ZrO2
Abstract
There is growing interest in the substitution of expensive noble metal catalysts with low-cost earth-abundant metals in applications targeting biofuels production from waste organic feedstocks. Here, nickel (Ni) catalysts supported on zirconium dioxide (ZrO2), both with and without copper (Cu) as a co-metal, were tested in hydrothermal reactions of unsaturated and saturated C18 fatty acids as models for waste oil feedstocks. In contrast to recent reports, this study showed no enhancement of nickel's activity for fatty acid conversion to alkane products when Cu was present. Ni/ZrO2 prepared by metal coprecipitation methods converted 100% of oleic acid with 25% selectivity to heptadecane after 5h of reaction at 350 °C using methanol as a hydrogen donor source, increasing to 41% heptadecane after 20 h. Lower yields were observed with catalysts prepared by wet impregnation and using alternative hydrogen donor sources (glycerol, formic acid). Greater selectivity to heptadecane was also observed at higher temperatures (370 °C) and when the initial fatty acid had greater saturation. Longer term exposure to hydrothermal media led to metal sintering and catalyst deactivation. Findings support a path forward to the development of earth-abundant metal catalysts for the upgrading of waste organic feedstocks.
- Authors:
-
- Colorado School of Mines, Golden, CO (United States)
- National Renewable Energy Laboratory (NREL), Golden, CO (United States)
- Harbin Institute of Technology (China)
- Alder Fuels, Washington, D.C. (United States)
- Publication Date:
- Research Org.:
- National Renewable Energy Laboratory (NREL), Golden, CO (United States)
- Sponsoring Org.:
- National Science Foundation (NSF)
- OSTI Identifier:
- 1993431
- Report Number(s):
- NREL/JA-5100-87064
Journal ID: ISSN 2772-4166; MainId:87839;UUID:7713e8e7-dde7-42c4-9bb2-b80086221977;MainAdminID:70084
- Grant/Contract Number:
- AC36-08GO28308; CBET-1804513
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of Hazardous Materials Advances
- Additional Journal Information:
- Journal Volume: 10; Journal ID: ISSN 2772-4166
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 09 BIOMASS FUELS; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Drop-in fuel; Earth abundant metals; Linoleic acid; Subcritical; Waste valorization
Citation Formats
Cronmiller, L. Estelle, Crawford, James M., Zhang, Jing, Vardon, Derek R., and Strathmann, Timothy J. Hydrothermal catalytic conversion of oleic acid to heptadecane over Ni/ZrO2. United States: N. p., 2023.
Web. doi:10.1016/j.hazadv.2023.100273.
Cronmiller, L. Estelle, Crawford, James M., Zhang, Jing, Vardon, Derek R., & Strathmann, Timothy J. Hydrothermal catalytic conversion of oleic acid to heptadecane over Ni/ZrO2. United States. https://doi.org/10.1016/j.hazadv.2023.100273
Cronmiller, L. Estelle, Crawford, James M., Zhang, Jing, Vardon, Derek R., and Strathmann, Timothy J. Sun .
"Hydrothermal catalytic conversion of oleic acid to heptadecane over Ni/ZrO2". United States. https://doi.org/10.1016/j.hazadv.2023.100273. https://www.osti.gov/servlets/purl/1993431.
@article{osti_1993431,
title = {Hydrothermal catalytic conversion of oleic acid to heptadecane over Ni/ZrO2},
author = {Cronmiller, L. Estelle and Crawford, James M. and Zhang, Jing and Vardon, Derek R. and Strathmann, Timothy J.},
abstractNote = {There is growing interest in the substitution of expensive noble metal catalysts with low-cost earth-abundant metals in applications targeting biofuels production from waste organic feedstocks. Here, nickel (Ni) catalysts supported on zirconium dioxide (ZrO2), both with and without copper (Cu) as a co-metal, were tested in hydrothermal reactions of unsaturated and saturated C18 fatty acids as models for waste oil feedstocks. In contrast to recent reports, this study showed no enhancement of nickel's activity for fatty acid conversion to alkane products when Cu was present. Ni/ZrO2 prepared by metal coprecipitation methods converted 100% of oleic acid with 25% selectivity to heptadecane after 5h of reaction at 350 °C using methanol as a hydrogen donor source, increasing to 41% heptadecane after 20 h. Lower yields were observed with catalysts prepared by wet impregnation and using alternative hydrogen donor sources (glycerol, formic acid). Greater selectivity to heptadecane was also observed at higher temperatures (370 °C) and when the initial fatty acid had greater saturation. Longer term exposure to hydrothermal media led to metal sintering and catalyst deactivation. Findings support a path forward to the development of earth-abundant metal catalysts for the upgrading of waste organic feedstocks.},
doi = {10.1016/j.hazadv.2023.100273},
journal = {Journal of Hazardous Materials Advances},
number = ,
volume = 10,
place = {United States},
year = {Sun Mar 05 00:00:00 EST 2023},
month = {Sun Mar 05 00:00:00 EST 2023}
}
Works referenced in this record:
A war running on fossil fuels
journal, June 2022
- Schiffer, Marike
- Nature Human Behaviour, Vol. 6, Issue 6
Catalytic Reactivity of CuNi Alloys toward H 2 O and CO Dissociation for an Efficient Water–Gas Shift: A DFT Study
journal, December 2011
- Gan, Li-Yong; Tian, Ren-Yu; Yang, Xiao-Bao
- The Journal of Physical Chemistry C, Vol. 116, Issue 1
A review of catalytic aqueous-phase reforming of oxygenated hydrocarbons derived from biorefinery water fractions
journal, July 2016
- Coronado, I.; Stekrova, M.; Reinikainen, M.
- International Journal of Hydrogen Energy, Vol. 41, Issue 26
Controlling Heterogeneous Catalysis with Organic Monolayers on Metal Oxides
journal, October 2021
- Jenkins, Alexander H.; Medlin, J. Will
- Accounts of Chemical Research, Vol. 54, Issue 21
Role of Composition and Geometric Relaxation in CO2 Binding to Cu–Ni Bimetallic Clusters
journal, December 2013
- Yang, Yang; Cheng, Daojian
- The Journal of Physical Chemistry C, Vol. 118, Issue 1
In-Situ Synthesis and Characterization of Biodegradable Estolides via Epoxidation from Canola Biodiesel
journal, October 2018
- Borugadda, Venu; Dalai, Ajay
- Lubricants, Vol. 6, Issue 4
TPR studies of the effects of preparation conditions on supported nickel catalysts
journal, October 1990
- Mile, B.; Stirling, D.; Zammitt, M. A.
- Journal of Molecular Catalysis, Vol. 62, Issue 2
Ultrasmall Ni nanoparticles embedded in Zr-based MOFs provide high selectivity for CO 2 hydrogenation to methane at low temperatures
journal, January 2018
- Zhao, Zhi-Wei; Zhou, Xiao; Liu, Ya-Nan
- Catalysis Science & Technology, Vol. 8, Issue 12
Biodiesel production from waste oil feedstocks by solid acid catalysis
journal, November 2008
- Peng, Bao-Xiang; Shu, Qing; Wang, Jin-Fu
- Process Safety and Environmental Protection, Vol. 86, Issue 6, p. 441-447
Directly transforming copper (I) oxide bulk into isolated single-atom copper sites catalyst through gas-transport approach
journal, August 2019
- Yang, Zhengkun; Chen, Bingxu; Chen, Wenxing
- Nature Communications, Vol. 10, Issue 1
Hydrothermal decarboxylation of unsaturated fatty acids over catalysts
journal, September 2015
- Yeh, Thomas M.; Hockstad, Ryan L.; Linic, Suljo
- Fuel, Vol. 156
Comparative life cycle assessment of NAD(P)H regeneration technologies
journal, January 2021
- Burnett, Joseph W. H.; Sun, Ziying; Li, Jianwei
- Green Chemistry, Vol. 23, Issue 18
Hydrothermal Catalytic Deoxygenation of Fatty Acid and Bio-oil with In Situ H2
journal, February 2018
- Miao, Chao; Marin-Flores, Oscar; Dong, Tao
- ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 4
Transfer Hydrogenation of Fatty Acids on Cu/ZrO2: Demystifying the Role of Carrier Structure and Metal–Support Interface
journal, July 2020
- Zhang, Zihao; Jing, Meizan; Chen, Hao
- ACS Catalysis, Vol. 10, Issue 16
Thermochemical biofuel production in hydrothermal media: A review of sub- and supercritical water technologies
journal, January 2008
- Peterson, Andrew A.; Vogel, Frédéric; Lachance, Russell P.
- Energy & Environmental Science, Vol. 1, Issue 1, p. 32-65
Catalytic Decarboxylation and Aromatization of Oleic Acid over Ni/AC without an Added Hydrogen Donor
journal, June 2018
- Zhang, Zihao; Chen, Zhe; Gou, Xin
- Industrial & Engineering Chemistry Research, Vol. 57, Issue 25
Efficient Conversion of Cellulose to Levulinic Acid by Hydrothermal Treatment Using Zirconium Dioxide as a Recyclable Solid Acid Catalyst
journal, June 2014
- Joshi, Sunil S.; Zodge, Amit D.; Pandare, Kiran V.
- Industrial & Engineering Chemistry Research, Vol. 53, Issue 49
Nickel-catalysed asymmetric hydrogenation of oximes
journal, June 2022
- Li, Bowen; Chen, Jianzhong; Liu, Dan
- Nature Chemistry, Vol. 14, Issue 8
Climate policies for freight transport: Energy and emission projections through 2050
journal, June 2021
- Yan, Shiyu; de Bruin, Kelly; Dennehy, Emer
- Transport Policy, Vol. 107
Role of Solvent in Catalytic Conversion of Oleic Acid to Aviation Biofuels
journal, June 2017
- Tian, Qiurong; Zhang, Zihao; Zhou, Feng
- Energy & Fuels, Vol. 31, Issue 6
Advances in biotechnological applications of waste cooking oil
journal, December 2021
- Awogbemi, Omojola; Kallon, Daramy Vandi Von; Aigbodion, Victor Sunday
- Case Studies in Chemical and Environmental Engineering, Vol. 4
Catalytic hydrothermal gasification of biomass
journal, January 2008
- Elliott, Douglas C.
- Biofuels, Bioproducts and Biorefining, Vol. 2, Issue 3
Effect of operating parameters on the selective catalytic deoxygenation of palm oil to produce renewable diesel over Ni supported on Al2O3, ZrO2 and SiO2 catalysts
journal, December 2020
- Papageridis, K. N.; Charisiou, N. D.; Douvartzides, S. L.
- Fuel Processing Technology, Vol. 209
Recent Advances in Hydroliquefaction of Biomass for Bio-oil Production Using In Situ Hydrogen Donors
journal, June 2020
- Zhao, Bojun; Hu, Yulin; Gao, Jihui
- Industrial & Engineering Chemistry Research, Vol. 59, Issue 39
Aqueous-phase reforming of methanol over nickel-based catalysts for hydrogen production
journal, November 2017
- Coronado, Irene; Stekrova, Martina; García Moreno, Lourdes
- Biomass and Bioenergy, Vol. 106
Dielectric properties of edible oils and fatty acids as a function of frequency, temperature, moisture and composition
journal, September 2008
- Lizhi, Hu; Toyoda, K.; Ihara, I.
- Journal of Food Engineering, Vol. 88, Issue 2
Hydrogen rich gas production via supercritical water gasification of sugarcane bagasse using unpromoted and copper promoted Ni/CNT nanocatalysts
journal, March 2015
- Rashidi, Masih; Tavasoli, Ahmad
- The Journal of Supercritical Fluids, Vol. 98
MOF-Derived Co3O4 Nanoparticles Catalyzing Hydrothermal Deoxygenation of Fatty Acids for Alkane Production
journal, September 2022
- Zeng, Defu; Li, Yalin; Xia, Tao
- ACS Omega, Vol. 7, Issue 37
Influence of ZrO 2 Structure and Copper Electronic State on Activity of Cu/ZrO 2 Catalysts in Methanol Synthesis from CO 2
journal, September 2014
- Samson, K.; Śliwa, M.; Socha, R. P.
- ACS Catalysis, Vol. 4, Issue 10
Comparative analysis of waste vegetable oil versus transesterified waste vegetable oil in diesel blend as alternative fuels for compression ignition engine
journal, July 2020
- Dey, Pritam; Ray, Srimanta
- Clean Technologies and Environmental Policy, Vol. 22, Issue 7
Production of Synthetic Diesel by Hydrotreatment of Jatropha Oils Using Pt−Re/H-ZSM-5 Catalyst
journal, April 2010
- Murata, Kazuhisa; Liu, Yanyong; Inaba, Megumu
- Energy & Fuels, Vol. 24, Issue 4
Nickel: The “Spirited Horse” of Transition Metal Catalysis
journal, February 2015
- Ananikov, Valentine P.
- ACS Catalysis, Vol. 5, Issue 3
The significant role of oxygen vacancy in Cu/ZrO2 catalyst for enhancing water–gas-shift performance
journal, January 2014
- Chen, Chongqi; Ruan, Chunxiao; Zhan, Yingying
- International Journal of Hydrogen Energy, Vol. 39, Issue 1
Mechanistic details of methane dry reforming on copper-nickel bimetallic surfaces
journal, January 2020
- Boualouache, Adel; Boucenna, Ali
- Chemical Physics Letters, Vol. 739
Dispersed Nickel Boosts Catalysis by Copper in CO2 Hydrogenation
journal, July 2020
- Wang, Ling-Xiang; Guan, Erjia; Wang, Zhiqiang
- ACS Catalysis, Vol. 10, Issue 16
Steam reforming of phenol-ethanol to produce hydrogen over bimetallic Ni Cu catalysts supported on sepiolite
journal, November 2017
- Liang, Tian; Wang, Yishuang; Chen, Mingqiang
- International Journal of Hydrogen Energy, Vol. 42, Issue 47
Fatty Acids Composition of Vegetable Oils and Its Contribution to Dietary Energy Intake and Dependence of Cardiovascular Mortality on Dietary Intake of Fatty Acids
journal, June 2015
- Orsavova, Jana; Misurcova, Ladislava; Ambrozova, Jarmila
- International Journal of Molecular Sciences, Vol. 16, Issue 12
Ni-containing Cu/SiO2 catalyst for the chemoselective synthesis of ethanol via hydrogenation of dimethyl oxalate
journal, November 2016
- Zhao, Yujun; Zhao, Shuo; Geng, Yaochen
- Catalysis Today, Vol. 276
Circular economy approach of enhanced bifunctional catalytic system of CaO/CeO2 for biodiesel production from waste loquat seed oil with life cycle assessment study
journal, May 2021
- Al-Muhtaseb, Ala'a H.; Osman, Ahmed I.; Murphin Kumar, Paskalis Sahaya
- Energy Conversion and Management, Vol. 236
High-temperature adsorption of carbon monoxide and hydrocarbon gases over nickel and platinum catalysts
journal, January 1998
- David Jackson, S.; Hussain, Naseem; Shona Munro, and
- Journal of the Chemical Society, Faraday Transactions, Vol. 94, Issue 7
In situ hydrogenation and decarboxylation of oleic acid into heptadecane over a Cu–Ni alloy catalyst using methanol as a hydrogen carrier
journal, January 2018
- Zhang, Zihao; Yang, Qiwei; Chen, Hao
- Green Chemistry, Vol. 20, Issue 1
Liquid-phase catalytic transfer hydrogenation and cyclization of levulinic acid and its esters to γ-valerolactone over metal oxide catalysts
journal, January 2011
- Chia, Mei; Dumesic, James A.
- Chemical Communications, Vol. 47, Issue 44
Liquefaction of Biomass and Upgrading of Bio-Oil: A Review
journal, June 2019
- Zhang, Shiqiu; Yang, Xue; Zhang, Haiqing
- Molecules, Vol. 24, Issue 12
Modelling the Sintering of Nickel Particles Supported on γ-Alumina under Hydrothermal Conditions
journal, December 2020
- Champon, Isabelle; Bengaouer, Alain; Chaise, Albin
- Catalysts, Vol. 10, Issue 12
Synthesis of acetic acid via methanol hydrocarboxylation with CO2 and H2
journal, May 2016
- Qian, Qingli; Zhang, Jingjing; Cui, Meng
- Nature Communications, Vol. 7, Issue 1
Continuous Catalytic Deoxygenation of Waste Free Fatty Acid-Based Feeds to Fuel-Like Hydrocarbons Over a Supported Ni-Cu Catalyst
journal, January 2019
- Loe, Ryan; Lavoignat, Yasmeen; Maier, Miranda
- Catalysts, Vol. 9, Issue 2
Activity and coke formation of nickel and nickel carbide in dry reforming: A deactivation scheme from density functional theory
journal, March 2014
- Wang, Ziyun; Cao, X. -M.; Zhu, Jinghao
- Journal of Catalysis, Vol. 311
Conversion of higher fatty acids or higher fatty acid esters to long-chain alkanes by acid added metal catalyst under mild hydrothermal conditions
journal, January 2022
- Cai, Xin; Zhang, Zhaoxia; Ye, Yueyuan
- Biomass and Bioenergy, Vol. 156
Life cycle assessment of a catalytic converter for passenger cars
journal, October 2001
- Amatayakul, Wathanyu; Ramnäs, Olle
- Journal of Cleaner Production, Vol. 9, Issue 5
Hydrothermal catalytic deoxygenation of palmitic acid over nickel catalyst
journal, February 2016
- Miao, Chao; Marin-Flores, Oscar; Davidson, Stephen D.
- Fuel, Vol. 166
Chemical Processing in High-Pressure Aqueous Environments. 8. Improved Catalysts for Hydrothermal Gasification
journal, May 2006
- Elliott, Douglas C.; Hart, Todd R.; Neuenschwander, Gary G.
- Industrial & Engineering Chemistry Research, Vol. 45, Issue 11
Hydrogen production via aqueous-phase reforming of methanol over nickel modified Ce, Zr and La oxide supports
journal, April 2018
- Stekrova, Martina; Rinta-Paavola, Aleksi; Karinen, Reetta
- Catalysis Today, Vol. 304
Hydrogenolysis of glycerol to propylene glycol in continuous system without hydrogen addition over Cu-Ni catalysts
journal, January 2018
- Freitas, Isabelle C.; Manfro, Robinson L.; Souza, Mariana M. V. M.
- Applied Catalysis B: Environmental, Vol. 220
Evaluation of a rapid method for the quantitative analysis of fatty acids in various matrices
journal, November 2008
- Araujo, Pedro; Nguyen, Thu-Thao; Frøyland, Livar
- Journal of Chromatography A, Vol. 1212, Issue 1-2
Bio-oil upgrading with catalytic pyrolysis of biomass using Copper/zeolite-Nickel/zeolite and Copper-Nickel/zeolite catalysts
journal, May 2019
- Kumar, Ravinder; Strezov, Vladimir; Lovell, Emma
- Bioresource Technology, Vol. 279
Hydrothermal catalytic processing of saturated and unsaturated fatty acids to hydrocarbons with glycerol for in situ hydrogen production
journal, January 2014
- Vardon, Derek R.; Sharma, Brajendra K.; Jaramillo, Humberto
- Green Chemistry, Vol. 16, Issue 3, p. 1507-1520
Decarboxylation of stearic acid over Ni/MOR catalysts
journal, October 2019
- Crawford, James M.; Zaccarine, Sarah F.; Kovach, Nolan C.
- Journal of Chemical Technology & Biotechnology, Vol. 95, Issue 1
Synergistic geometric and electronic effects for electrochemical reduction of carbon dioxide using gold–copper bimetallic nanoparticles
journal, September 2014
- Kim, Dohyung; Resasco, Joaquin; Yu, Yi
- Nature Communications, Vol. 5, Issue 1
Catalytic hydrothermal deoxygenation of palmitic acid
journal, January 2010
- Fu, Jie; Lu, Xiuyang; Savage, Phillip E.
- Energy & Environmental Science, Vol. 3, Issue 3
Aerobic granular sludge: characterization, mechanism of granulation and application to wastewater treatment
journal, October 2010
- Gao, Dawen; Liu, Lin; Liang, Hong
- Critical Reviews in Biotechnology, Vol. 31, Issue 2
Highly active and stable Ni/Ce–ZrO2 catalyst for H2 production from methane
journal, March 2002
- Roh, H.
- Journal of Molecular Catalysis A: Chemical, Vol. 181, Issue 1-2
Metal oxide supported Ni-impregnated bifunctional catalysts for controlling char formation and maximizing energy recovery during catalytic hydrothermal liquefaction of food waste
journal, January 2021
- Cheng, Feng; Tompsett, Geoffrey A.; Fraga Alvarez, Daniela Valeska
- Sustainable Energy & Fuels, Vol. 5, Issue 4
Kinetics and mechanism for hydrothermal conversion of polyhydroxybutyrate (PHB) for wastewater valorization
journal, January 2019
- Li, Yalin; Strathmann, Timothy J.
- Green Chemistry, Vol. 21, Issue 20
Kinetically Controlled Coprecipitation for General Fast Synthesis of Sandwiched Metal Hydroxide Nanosheets/Graphene Composites toward Efficient Water Splitting
journal, November 2017
- Tang, Tang; Jiang, Wen-Jie; Niu, Shuai
- Advanced Functional Materials, Vol. 28, Issue 3
Catalytic Deoxygenation of Fatty Acids and Their Derivatives
journal, January 2007
- Mäki-Arvela, Päivi; Kubickova, Iva; Snåre, Mathias
- Energy & Fuels, Vol. 21, Issue 1, p. 30-41
Efficient and stable Cu-Ni/ZrO2 catalysts for in situ hydrogenation and deoxygenation of oleic acid into heptadecane using methanol as a hydrogen donor
journal, October 2018
- Zhang, Zihao; Chen, Hao; Wang, Changxue
- Fuel, Vol. 230
Synthesis and characterization of biodegradable palm palmitic acid based bioplastic
journal, June 2021
- Japir, Abd Al-Wali; Salih, Nadia; Salimon, Jumat
- TURKISH JOURNAL OF CHEMISTRY, Vol. 45, Issue 3
War and the Politics of Energy and Climate Change
journal, April 2022
- O’Riordan, Tim; Sandford, Bob
- Environment: Science and Policy for Sustainable Development, Vol. 64, Issue 3
Hydrothermal Decarboxylation and Hydrogenation of Fatty Acids over Pt/C
journal, January 2011
- Fu, Jie; Lu, Xiuyang; Savage, Phillip E.
- ChemSusChem, Vol. 4, Issue 4
Unraveling the surface state and composition of highly selective nanocrystalline Ni–Cu alloy catalysts for hydrodeoxygenation of HMF
journal, January 2017
- Luo, Jing; Monai, Matteo; Wang, Cong
- Catalysis Science & Technology, Vol. 7, Issue 8
Influence of the support structure and composition of Ni–Cu-based catalysts on hydrogen production by methanol steam reforming
journal, August 2015
- Lytkina, A. A.; Zhilyaeva, N. A.; Ermilova, M. M.
- International Journal of Hydrogen Energy, Vol. 40, Issue 31