Synthesis of 5-(Hydroxymethyl)furfural Monoesters and Alcohols as Fuel Additives toward Their Performance and Combustion Characteristics in Compression Ignition Engines

Ob Nilaphai; Sukanya Thepwatee; Piriya Kaeopookum; Laksamee Chaicharoenwimolkul Chuaitammakit; Chonticha Wongchaichon; Onnicha Rodjang; Prapapron Pudsong; Wanida Singhapon; Thanakorn Burerat; Siriporn Kamtaw; Sathaporn Chuepeng; Sopanat Kongsriprapan

doi:10.1021/acsomega.3c02385

Synthesis of 5-(Hydroxymethyl)furfural Monoesters and Alcohols as Fuel Additives toward Their Performance and Combustion Characteristics in Compression Ignition Engines

ACS Omega. 2023 May 4;8(19):17327-17336. doi: 10.1021/acsomega.3c02385. eCollection 2023 May 16.

Affiliations

¹ ATAE Research Unit, Department of Mechanical Engineering, Faculty of Engineering at Sriracha, Kasetsart University, Thung Sukhla, Chon Buri 20230, Thailand.
² Department of Industrial Chemistry, Faculty of Applied Science, King Mongkut's University of Technology North Bangkok, Bangkok 10800, Thailand.
³ Nuclear Technology Research and Development Center, Thailand Institute of Nuclear Technology, Ongkarak, Nakhon Nayok 26120, Thailand.
⁴ Chemistry, Faculty of Science and Technology, Suratthani Rajabhat University, 272 Moo 9, Surat-Nasan Road, Khuntale, Muang, Surat Thani 84100, Thailand.
⁵ Department of Basic Science and Physical Education, Faculty of Science at Sriracha, Kasetsart University, Tung Sukla, Chon Buri 20230, Thailand.

Abstract

The synthesis of 5-(hydroxymethyl)furfural (HMF) and conversion to the corresponding HMF-monoesters upon certain treatment are presented with their properties that are validated in a diesel engine. With a collection of fatty acids (C8-C18) using cyanuric acid as a catalyst under mild reaction conditions, the subsequent reduction of the HMF-monoesters with NaBH₄ produced the corresponding alcohols. After purification, both HMF-monoesters and their alcohol derivatives were determined for their solubility, cetane index, heat of combustion, viscosity, and specific gravity. HMF-Capric (1-C10), HMF-Oleic (1-C18:1), HMF-Caprylic-OH (2-C8), and HMF-Oleic-OH (2-C18:1) were soluble in a neat diesel fuel. The observed highest cetane index and heat of combustion of 1-C10 and 1-C18:1 were evaluated for combustion characteristics in a single-cylinder compression ignition engine. The diesel fuel containing 3% 1-C10 displayed comparable properties during burning in terms of thermal efficiency, cylinder pressure, and heat release rate with respect to the neat diesel fuel (D100) for all usage engine speeds. In general, all tested fuels initiated their burning onset with a similar ignition delay period. The 3% 1-C10-blended diesel fuel emitted slightly higher smoke opacity but an equivalent nitric oxide level compared to those of D100. The HMF-Capric (1-C10) synthesized in this study represents a promising additive for diesel fuel. Blended fuel lubricity and other unregulated emissions upon broader engine test cycles are suggested to be accomplished in future work.