Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 9, Issue 40, Pages 13424-13437Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.1c03523
Keywords
biolubricants; waste cooking oil; Friedel-Crafts acylation; biomass; model compounds
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Funding
- Alabama Agricultural Experiment Station
- Hatch program of the National Institute of Food and Agriculture, U.S. Department of Agriculture (USDA) [ALA014-119068]
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This study proposes a novel approach to produce biolubricants through the reaction between waste cooking oil and cyclic oxygenated hydrocarbons. The resulting biolubricants have long hydrocarbon chains, low unsaturation, naphthenic rings, and polar molecules, demonstrating good pour-point, viscosity, viscosity index, and volatility properties.
The present research and development for lubricant production from vegetable oils rely on traditional (trans)esterification, etherification, and/or chemical modifications of triglycerides and free fatty acids (FFAs). However, the final products suffer from at least one of the following: poor low-temperature characteristics, low oxidation stability, low viscosity index, or poor solubility of additives. This study presents a novel approach to produce biolubricants (BL) from the reaction of waste cooking oil (WCO) and cyclic oxygenated hydrocarbons (COHCs) (cyclopentanone, cyclopentanol, anisole, and 2-methylfuran) via a four-step pathway: hydrolysis, dehydration/ketonization, Friedel-Crafts (FC) acylation/alkylation, and hydrotreatment. Such reactions were successfully demonstrated using model compounds (oleic acid and stearic acid) and actual WCO feedstock. The process resulted in the production of novel BLs that were consisted of molecules with several mutual properties: (1) long and linear hydrocarbon chains, (2) low to zero unsaturation, (3) minimal branching, (4) naphthenic rings and cyclic structures, and (5) polar molecules. We showed that such BLs can be synthesized with pour-point, kinematic viscosity (at 40 degrees C), viscosity index, and Noack volatility of -12 degrees C, 47.5 cP, 186, and 17 wt %, respectively.
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