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Open AccessArticle

Application of Phase Transfer Catalysis in the Esterification of Organic Acids: The Primary Products from Ring Hydrocarbon Oxidation Processes

by Hui Wang 1,2,*,†, Hongfei Lin 2,†, Xiaohu Li 2,3, Rui Ren 2,3, Jianglong Pu 1, Haiping Zhang 4, Ying Zheng 2,5,*, Jianshe Zhao 3, Siauw Ng 6 and Hui Zhang 4,5
1
College of Biological, Chemical Sciences and Engineering, Jiaxing University, 118 Jiahang Road, Jiaxing 314001, China
2
Department of Chemical Engineering, University of New Brunswick, 15 Dineen Drive, Fredericton, NB E3B 5A3, Canada
3
College of Chemistry and Materials Science, Northwest University, Xi’an 710069, China
4
Department of Chemical Engineering & Technology, Tianjin University, Tianjin 300072, China
5
Department of Chemical and Biochemical Engineering, Western University, 1151 Richmond Street, London, ON N6A 3K7, Canada
6
National Centre for Upgrading Technology, Canmet ENERGY-Devon, 1 Oil Patch Drive, Edmonton, AB T9G 1A8, Canada
*
Authors to whom correspondence should be addressed.
As the co-first author.
Catalysts 2019, 9(10), 851; https://doi.org/10.3390/catal9100851
Received: 11 September 2019 / Revised: 8 October 2019 / Accepted: 9 October 2019 / Published: 13 October 2019
For enhancing the cetane number (CN) of diesel fraction, the selective oxidative ring opening method was applied to upgrade ring hydrocarbons. Organic acids, one of the main products from this oxidative reaction, being esterified by the phase transfer catalysis (PTC) approach were studied. Adipic acid, benzoic acid, and phthalic acid were used as model compounds. Reaction time, reaction temperature, the amount of water, and the amount of catalyst in the esterification process were investigated and optimized using orthogonal experimental design method. The kinetics of esterification process was then conducted under the optimal condition. The types of catalysts and organic acids, the amount of catalyst and water were also investigated. The PTC esterification was one rate controlling reaction on the interface between the aqueous phase and the oil phase. Hydrophobicity is a key factor for converting benzoic acid, adipic acid, and phthalic acid to the corresponding esters. It was found that around 5–8% water is the optimal quantity for the given reaction system. Two cases of esterification processes of PTC were proposed. View Full-Text
Keywords: cetane number enhancement; phase transfer catalysis; organic acid esterification; reaction kinetics; orthogonal experimental method cetane number enhancement; phase transfer catalysis; organic acid esterification; reaction kinetics; orthogonal experimental method
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Wang, H.; Lin, H.; Li, X.; Ren, R.; Pu, J.; Zhang, H.; Zheng, Y.; Zhao, J.; Ng, S.; Zhang, H. Application of Phase Transfer Catalysis in the Esterification of Organic Acids: The Primary Products from Ring Hydrocarbon Oxidation Processes. Catalysts 2019, 9, 851.

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