(744c) Renewable Lubricant Alkanes from Biomass-Derived Platform Chemicals

Branched, high-carbon alkanes are important components in base-oils. Such lubricant alkanes are currently obtained by hydrocracking and hydroisomerization of long-chain n-paraffins or by oligomerization of olefins.^1-2 A cost-competitive and scalable method for lubricant-range, branched alkanes with tunable molecular structures has yet to be developed from biomass platform chemicals, although there are recent reports on the synthesis of renewable lubricants with cyclic structures from biomass furans or branched molecules from natural oils.^3-4 In this work, we describe a selective method for large alkanes’ synthesis from fatty acids and furans, biomass platform chemicals. We invoke C-C coupling paths, such as furan condensation and ketonization, and hydrodeoxygenation (HDO) reactions. Reaction conditions are selected to enhance the yield of products. Important properties (viscosity index, pour point, volatility, and thermal stability) of the synthesized alkanes are compared with those of commercial products. In conclusion, this work demonstrates a potential strategy for the synthesis of high-quality lubricant alkanes from renewable biomass.

References:

1. Calemma, V.; Peratello, S.; Stroppa, F.; Giardino, R.; Perego, C., Hydrocracking and hydroisomerization of long-chain n-paraffins. Reactivity and reaction pathway for base oil formation. Ind. Eng. Chem. Res. 2004, 43 (4), 934-940. [10.1021/ie0304309]
2. Ghosh, R.; Bandyopadhyay, A. R.; Jasra, R.; Gagjibhai, M. M., Mechanistic Study of the Oligomerization of Olefins. Ind. Eng. Chem. Res. 2014, 53 (18), 7622-7628. [10.1021/ie500688x]
3. Gu, M. Y.; Xia, Q. N.; Liu, X. H.; Guo, Y.; Wang, Y. Q., Synthesis of Renewable Lubricant Alkanes from Biomass-Derived Platform Chemicals. ChemSusChem 2017, 10 (20), 4102-4108. [10.1002/cssc.201701200]
4. Jadhav, D.; Grippo, A. M.; Shylesh, S.; Gokhale, A. A.; Redshaw, J.; Bell, A. T., Production of Biomass-Based Automotive Lubricants by Reductive Etherification. ChemSusChem 2017, 10 (11), 2527-2533. [10.1002/cssc.201700427]