Chemical Modification of Camelina Oil based Unsaturated Fatty Acid for Renewable Biolubricant Base Stock

Abstract

A green and eco-friendly method for preparation of oleochemicals from Camelina oil was developed for possible application for bio-lubricant basestocks, The steps involved are consisting of epoxidation of Camelina oil based fatty acid followed by further branching with wide range of alcohol such as 2-propanol, n-butanol, isoamyl alcohol and 2-ethylhexanol. These products were evaluated with physico-chemical properties such as acid value, oxirane oxygen content (OOC), hydroxyl value, low temperature properties, viscosity at 40 and 100 °C, viscosity index and characterized by FTIR, 1H NMR. The appearance of peak at 824 cm–1 in the FTIR spectra was due to the formation of epoxy group and broad peak appeared at 3500-3300 cm–1 is for hydrogen bonded O-H stretching vibration of hydroxy group. The 1H NMR spectra showed a signal at 2.9-3.2 ppm region indicated CH-proton attached to the oxygen atom of the both epoxy group for epoxidized product, peaks for newly formed secondary alcohols emerged at 4.25-3.35 in alkoxy derivatives. The Camelina based synthetic product may find application in biolubricants base stock.

Valorization of camelina oil to biobased materials and biofuels for new industrial uses: a review

“…The authors observed interesting properties for the camelina derived alkoxy fatty acids which suggested their great potential for low temperature applications as bio-lubricant base stocks and good alternatives for synthetic and mineral oil derived lubricants. 112 In a recent report by Mauro and coworkers (2021), 119 they reported on the synthesis of reprocessable resins derived from epoxidized camelina oil when using antagonistic structures, either aromatic or aliphatic amines or acids, as hardeners. They explored two different combinations: the rst was a combination of aliphatic/aliphatic carboxylic acids (3,3 0 -dithiodipropionic acid, and 2,2 0 -dithiodibenzoic acid), while the second consisted of only aromatic structures with acid/amine functionality (4-aminophenyl disulde, and 2,2 0 -dithiodibenzoic acid).…”

“… 111 Moreover, ring opening of fully epoxidized camelina oil by reacting with a range of different alcohols to develop oleochemicals with potential application as bio-lubricant base stocks has also been investigated. 112 Derivatization of camelina oil by partial epoxidation using in situ performic acid followed by hydroxylation with an alcohol in the presence of acid catalyst is carried out to replace castor oil polyols. 113 Chemical functionalization of fully epoxidized camelina oil into partially acrylated triglycerides followed by their hydroxylation to develop dihydroxyl acrylated camelina oil, an acrylic polyol with one acrylate functional group, has also been shown to produce polymerizable materials.…”

“…The authors observed interesting properties for the camelina derived alkoxy fatty acids which suggested their great potential for low temperature applications as bio-lubricant base stocks and good alternatives for synthetic and mineral oil derived lubricants. 112 …”

Camelina sativa Composition, Attributes, and Applications: A Review

“…In most works, camelina oil was used. [89][90][91][92][93][94][95][96] However, some studies have also considered the camelina proteins. [93,94,97,98]…”

“…Sharma et al [96] chemically modified camelina oil for the preparation of renewable biolubricant base stock. The first step consisted in the epoxidation of camelina oil based fatty acid followed by further branching with 2-propanol, n-butanol, isoamyl alcohol or 2-ethylhexanol.…”