Metathesis as a versatile tool in oleochemistry

Abstract

Olefin metathesis, awarded with the Nobel Prize in Chemistry 2005 for Chauvin, Grubbs and Schrock, has emerged as a powerful tool for organic as well as polymer chemistry. In oleochemistry, this reaction is well known and has been applied for many decades. Examples include the functionalization of the double bonds of different oleochemicals or the (direct) polymerization of plant oils via metathesis. More recent developments, particularly the development of better and more robust catalysts, allow for highly efficient cross-metathesis reactions opening new possibilities for the direct introduction of chemical functionalities. Within this contribution, the development of metathesis in oleochemistry will be discussed, covering selfmetathesis as well as more recent developments in the field of cross-metathesis that lead to desired platform chemicals.

Chemically Modifying Vegetable Oils to Prepare Green Lubricants

“…The invention is further related to telomerized triglyceride vegetable oils as a lubricating composition base stock substitute. Recently, relatively new polymerization methods such as acyclic diene metathesis polymerization [147] and ring-opening metathesis polymerization [148,149] of functionalized fatty alcohols have been employed to synthesize vegetable oil-based polymers as well. Polymerization of vegetable oils/derivatives in the presence of different organic or inorganic nanofillers produces polymer nano-composites, which are extensively applied in the automotive industry, especially as an antiwear coating/additive in lubricants [150].…”

Polymer precursors from catalytic reactions of natural oils

“…14 Value enhancement of triglycerides leads to the preparation of industrial products and mainly to surfactants, lubricants and polymers. [15][16][17][18] For instance, the production of surfactants being efficient and presenting interesting properties such as biocompatibility and biodegradability 19,20 is a successful example of industrial conversion of vegetable oils into valuable chemicals. [21][22][23] The area of industrial conversion of oils into chemicals being wide, the reader's attention will now be focused only in the field of polymers.…”

Heterotrophy of filamentous oleaginous microalgae Tribonema minus for potential production of lipid and palmitoleic acid

“…Moreover, palmitoleic acid is thought to be better to provide low temperature property than other saturated fatty acid when it was converted into biodiesel because of its carbon chain length and unsaturated double bond number (Knothe, 2010;Cao et al, 2014). Besides, palmitoleic acid could be used to produce 1-octene which is highly consumed in the expanding production of linear low density polyethylene (Rybak et al, 2008;Nguyen et al, 2010).…”