Enzymatic synthesis of a novel solid–liquid phase change energy storage material based on levulinic acid and 1,4-butanediol

Siyu Zhai , Lihe Zhang , Xi Zhao , Qian Wang , Yin Yan , Cui Li , Xu Zhang

Bioresources and Bioprocessing ›› 2022, Vol. 9 ›› Issue (1) : 12

PDF
Bioresources and Bioprocessing ›› 2022, Vol. 9 ›› Issue (1) : 12 DOI: 10.1186/s40643-022-00502-w
Research

Enzymatic synthesis of a novel solid–liquid phase change energy storage material based on levulinic acid and 1,4-butanediol

Author information +
History +
PDF

Abstract

The current energy crisis has prompted the development and utilization of renewable energy and energy storage material. In this study, levulinic acid (LA) and 1,4-butanediol (BDO) were used to synthesize a novel levulinic acid 1,4-butanediol ester (LBE) by both enzymatic and chemical methods. The enzymatic method exhibited excellent performance during the synthesis process, and resulted in 87.33% of LBE yield, while the chemical method caused more by-products and higher energy consumption. What’s more, the thermal properties of the obtained LBE as a phase change material (PCM) were evaluated. Differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) showed that the melting temperature, latent heat of melting, and pyrolysis temperature were 50.51 °C, 156.1 J/g, and 150–160 °C, respectively. Compared with the traditional paraffin, the prepared PCM has a superior phase transition temperature, a higher latent heat of melting, and better thermal stability. The thermal conductivity could be increased to 0.34 W/m/k after adding expanded graphite (EG). In summary, LBE has great potential in the application of energy storage as a low-temperature phase change energy storage material.

Keywords

Levulinic acid / Polyol ester / Thermal properties / Enzymatic method / Thermal reliability

Cite this article

Download citation ▾
Siyu Zhai, Lihe Zhang, Xi Zhao, Qian Wang, Yin Yan, Cui Li, Xu Zhang. Enzymatic synthesis of a novel solid–liquid phase change energy storage material based on levulinic acid and 1,4-butanediol. Bioresources and Bioprocessing, 2022, 9(1): 12 DOI:10.1186/s40643-022-00502-w

登录浏览全文

4963

注册一个新账户 忘记密码

References

[1]

Adeleye TA, Louis H, Akakuru OU, Joseph I, Enudi OC, Michael DP. A review on the conversion of levulinic acid and its esters to various useful chemicals. AIMS Energy, 2019, 7(2): 165-185.

[2]

Åkerman CO, Hagström AEV, Mollaahmad MA, Karlsson S, Hatti-Kaul R. Biolubricant synthesis using immobilised lipase: process optimisation of trimethylolpropane oleate production. Process Biochem, 2011, 46(12): 2225-2231.

[3]

Alegría A, Cuellar J. Esterification of oleic acid for biodiesel production catalyzed by 4-dodecylbenzenesulfonic acid. Appl Catal B-Environ, 2015, 179: 530-541.

[4]

Badgujar KC, Bhanage BM. The green metric evaluation and synthesis of diesel-blend compounds from biomass derived levulinic acid in supercritical carbon dioxide. Biomass Bioenergy, 2016, 84: 12-21.

[5]

Byrne FP, Assemat JMZ, Stanford AE, Farmer TJ, Comerford JW, Pellis A. Enzyme-catalyzed synthesis of malonate polyesters and their use as metal chelating materials. Green Chem, 2021, 23(14): 5043-5048.

[6]

Climent MJ, Corma A, Iborra S. Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels. Green Chem, 2014, 16(2): 516-547.

[7]

Dutta S, Yu IKM, Tsang DCW, Ng YH, Ok YS, Sherwood J. Green synthesis of gamma-valerolactone (GVL) through hydrogenation of biomass-derived levulinic acid using non-noble metal catalysts: a critical review. Chem Eng J, 2019, 372: 992-1006.

[8]

Jaiswal KS, Rathod VK. Green synthesis of amyl levulinate using lipase in the solvent free system: optimization, mechanism and thermodynamics studies. Catal Today, 2021, 375: 120-131.

[9]

Jeong H, Jang SK, Hong CY, Kim SH, Lee SY, Lee SM. Levulinic acid production by two-step acid-catalyzed treatment of Quercus mongolica using dilute sulfuric acid. Bioresour Technol, 2017, 225: 183-190.

[10]

Ji H, Wang B, Zhang X, Tan T. Synthesis of levulinic acid-based polyol ester and its influence on tribological behavior as a potential lubricant. RSC Adv, 2015, 5(122): 100443-100451.

[11]

Jones DR, Iqbal S, Ishikawa S, Reece C, Thomas LM, Miedziak PJ. The conversion of levulinic acid into γ-valerolactone using Cu–ZrO2 catalysts. Catal Sci Technol, 2016, 6(15): 6022-6030.

[12]

Kant K, Shukla A, Sharma A. Ternary mixture of fatty acids as phase change materials for thermal energy storage applications. Energy Rep, 2016, 2: 274-279.

[13]

Lăcătuş MA, Bencze LC, Toşa MI, Paizs C, Irimie FD. Eco-friendly enzymatic production of 2,5-bis(hydroxymethyl)furan fatty acid diesters, potential biodiesel additives. ACS Sustain Chem Eng, 2018, 6(9): 11353-11359.

[14]

Liang J, Zhang X, Ji J. Hygroscopic phase change composite material—a review. J Energy Storage, 2021

[15]

Liu W, Xiao B, Wang X, Chen J, Yang G. Solvent-free synthesis of phytosterol linoleic acid esters at low temperature. RSC Adv, 2021, 11(18): 10738-10746.

[16]

Mazman M, Cabeza LF, Mehling H, Paksoy , Evliya H. Heat transfer enhancement of fatty acids when used as PCMs in thermal energy storage. Res Int J Energy Res, 2008, 32(2): 135-143.

[17]

Moon M, Yeon YJ, Park HJ, Park J, Park GW, Kim GH. Chemoenzymatic valorization of agricultural wastes into 4-hydroxyvaleric acid via levulinic acid. Bioresour Technol, 2021, 337: 125479.

[18]

Mukherjee A, Dumont M-J, Raghavan V. Review: Sustainable production of hydroxymethylfurfural and levulinic acid: challenges and opportunities. Biomass Bioenergy, 2015, 72: 143-183.

[19]

Oliveira BL, Teixeira da Silva V. Sulfonated carbon nanotubes as catalysts for the conversion of levulinic acid into ethyl levulinate. Catal Today, 2014, 234: 257-263.

[20]

Ortiz C, Ferreira ML, Barbosa O, dos Santos JCS, Rodrigues RC, Berenguer-Murcia,. Novozym 435: the “perfect” lipase immobilized biocatalyst?. Catal Sci Technol, 2019, 9(10): 2380-2420.

[21]

Paul J, Kadirgama K, Samykano M, Pandey AK, Tyagi VV. A comprehensive review on thermophysical properties and solar thermal applications of organic nano composite phase change materials. J Energy Storage, 2021

[22]

Qin Y-Z, Zong M-H, Lou W-Y, Li N. Biocatalytic Upgrading of 5-hydroxymethylfurfural (hmf) with levulinic acid to hmf levulinate in biomass-derived solvents. ACS Sustain Chem Eng, 2016, 4(7): 4050-4054.

[23]

Ravotti R, Fellmann O, Fischer LJ, Worlitschek J, Stamatiou A. Assessment of the thermal properties of aromatic esters as novel phase change materials. Curr Comput-Aided Drug Des, 2020, 10(10): 919.

[24]

Robles-Medina A, Gonzalez-Moreno PA, Esteban-Cerdan L, Molina-Grima E. Biocatalysis: towards ever greener biodiesel production. Biotechnol Adv, 2009, 27(4): 398-408.

[25]

Sari A. Thermal energy storage properties of mannitol–fatty acid esters as novel organic solid–liquid phase change materials. Energy Convers Manage, 2012, 64: 68-78.

[26]

Sarı A, Karaipekli A. Fatty acid esters-based composite phase change materials for thermal energy storage in buildings. Appl Therm Eng, 2012, 37: 208-216.

[27]

Sjöblom M, Risberg P, Filippova A, Öhrman OGW, Rova U, Christakopoulos P. In situ biocatalytic synthesis of butyl butyrate in diesel and engine evaluations. ChemCatChem, 2017, 9(24): 4529-4537.

[28]

Song M, Di X, Zhang Y, Sun Y, Wang Z, Yuan Z. The effect of enzyme loading, alcohol/acid ratio and temperature on the enzymatic esterification of levulinic acid with methanol for methyl levulinate production: a kinetic study. RSC Adv, 2021, 11(25): 15054-15059.

[29]

Stamatiou A, Obermeyer M, Fischer LJ, Schuetz P, Worlitschek J. Investigation of unbranched, saturated, carboxylic esters as phase change materials. Renew Energy, 2017, 108: 401-409.

[30]

Trombettoni V, Bianchi L, Zupanic A, Porciello A, Cuomo M, Piermatti O. Efficient catalytic upgrading of levulinic acid into alkyl levulinates by resin-supported acids and flow reactors. Catalysts, 2017, 7(8): 235.

[31]

Wang R, Ren M, Gao X, Qin L. Preparation and properties of fatty acids based thermal energy storage aggregate concrete. Constr Build Mater, 2018, 165: 1-10.

[32]

Wang Z, Li R, Hu J, Hu X, Gu Z. Experimental study on hybrid organic phase change materials used for solar energy storage. J Therm Sci, 2020, 29(2): 486-491.

[33]

Wu MY, Sung LY, Li H, Huang CH, Hu YC. Combining CRISPR and CRISPRi Systems for Metabolic Engineering of E coli and 1,4-BDO Biosynthesis. ACS Synth Biol, 2017, 6(12): 2350-2361.

[34]

Zhang Y, Wang L, Tang B, Lu R, Zhang S. Form-stable phase change materials with high phase change enthalpy from the composite of paraffin and cross-linking phase change structure. Appl Energy, 2016, 184: 241-246.

[35]

Zhang W, Zhang X, Huang Z, Yin Z, Wen R, Huang Y. Preparation and characterization of capric-palmitic-stearic acid ternary eutectic mixture/expanded vermiculite composites as form-stabilized thermal energy storage materials. J Mater Sci Technol, 2018, 34(2): 379-386.

[36]

Zhang W, Wu J, Yu S, Shen Y, Wu Y, Chen B. Modification and synthesis of low pour point plant-based lubricants with ionic liquid catalysis. Renew Energy, 2020, 153: 1320-1329.

[37]

Zhao Y, Zhang X, Hua W. Review of preparation technologies of organic composite phase change materials in energy storage. J Mol Liq, 2021

[38]

Zhu W, Liang F, Hou H, Chen Y, Liu X, Zhu X. Enzymatic synthesis of a polyol ester from levulinic acid and trimethylolpropane and its tribological behavior as potential biolubricant basestock. Polymers-Basel, 2020, 12(10): 2256.

Funding

the National Key Research and Development Program of China(2021YFC2101300)

AI Summary AI Mindmap
PDF

135

Accesses

0

Citation

Detail

Sections
Recommended

AI思维导图

/