Biodegradable base stock oils obtained from ricinoleic acid using C 8 alcohols and process integration into a biodiesel

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ORIGINAL ARTICLE

Biodegradable base stock oils obtained from ricinoleic acid using C8 alcohols and process integration into a biodiesel industry Ítalo C. Rios 1 & João Paulo Cordeiro 1 & Expedito J.S. Parente Jr 1 & Solange A. Quintella 1 & José Alemán 2 & Célio L. Cavalcante Jr 1 & F. Murilo T. Luna 1 Received: 28 April 2020 / Revised: 15 July 2020 / Accepted: 4 August 2020 # Springer-Verlag GmbH Germany, part of Springer Nature 2020

Abstract The strategies for sustainability and competitiveness of the biodiesel industry may be improved by adding value through coproducts, especially for novel biodegradable products from non-edible vegetable oils. In this study, the chemical modifications of ricinoleic acid obtained from castor oil were performed to obtain biodegradable base stock oils. The chemical route was carried out using C8 alcohols (octanol or 2-ethyl-hexanol) in esterification and oxirane rings opening reactions under commercial catalysts. All chemical modifications were monitored by nuclear magnetic resonance (1H NMR) and physicochemical properties of products. The biodegradability of synthesized samples was determined using a bio-kinetic model. The results indicated that the bio-based samples from 2-ethyl-hexanol had the lowest pour point (− 57 °C) and the highest oxidative stability. The biodegradability tests showed that all synthesized samples have half-life around 20–60 days. From these results, this studied route using ricinoleic acid and C8 alcohols was considered to be applied to an existing biodiesel industry. Finally, a multi-purpose flexible industrial configuration was proposed to be able to obtain both biodiesel and the biodegradable base stocks for lubricant oils. Keywords Biodegradable lubricants . Epoxidation . Biodegradability . Biodiesel industry

1 Introduction Mineral base lubricants oils are commonly obtained from petroleum processing usually treated by distillation and other refining processes [1]. They are used in several mechanical applications for reducing friction and preventing wear between two surfaces in relative motion, forming a liquid film that decreases heat generation, minimizing energy losses, and may increase equipment lifetime [2–4]. Depending on their application, they can also perform cooling, cleaning of moving parts, sealing, insulation, protection, as well as mechanical Electronic supplementary material The online version of this article (https://doi.org/10.1007/s13399-020-00942-4) contains supplementary material, which is available to authorized users. * F. Murilo T. Luna [email protected] 1

Departamento de Engenharia Química, Grupo de Pesquisa em Separações por Adsorção, Núcleo de Pesquisas em Lubrificantes, Universidade Federal do Ceará, Campus do Pici, Bl. 1010, Fortaleza, CE 60455-900, Brazil

2

Science Faculty, Organic Chemistry Department, Universidad Autónoma de Madrid, Module 01, 28049 Madrid, Spain

power transmission and additives to transfer certain physical and chemical characteristics to other products. Lubricants are important commercial product