Main achievements and innovations are summarised below.
Successful large field trials:
Field trials with camelina and crambe have been performed in Greece, Italy, Poland and The Netherlands to assess the potential of the crops. It was found that camelina can be grown both as a spring crop and as a winter crop in Mediterranean climates (Greece, Italy), which opens up additional options for farmers to fit camelina into rotation schemes. Furthermore, innovative double cropping systems have been explored as a means to generate better income for farmers.
New crambe and camelina varieties with increased value for animal feed and oleochemistry:
Non-transgenic modern plant breeding techniques have successfully been applied to significantly reduce the amounts of bitter tasting compounds in the seeds. These have a negative effect on animal growth and hence reduce the feed value of the seed residues remaining after seed oil extraction. Using the same techniques, COSMOS scientists were able to reduce the share of polyunsaturated FA in the oils, while at the same time increasing the levels of monounsaturated FA desired by the chemical industry. Hence, the potential of the oils to serve as a feedstock for the chemical industry, particularly to produce medium-chain oleochemicals, has increased greatly.
Novel enzymes with improved FA chain length selectivity:
Long-chain monounsaturated FA are interesting building blocks in the oleochemical industry. Specifically, gondoic (C20:1 cisΔ11) and erucic acid (C22:1 cisΔ13) are present in large amounts in camelina and crambe oil, respectively, and need to be isolated from the FA mixture of the oils. As a better alternative for conventional techniques, project partners University of Greifswald and the company Enzymicals developed an enzymatic method to isolate oil fractions with increased shares of gondoic and erucic acid. The method uses selective lipases that were designed to discriminate between very long-chain FA such as gondoic and erucic acid, and slightly shorter ones. The technology was particularly effective in enriching the levels of erucic acid in crambe oil, probably due to its longer chain length (22 carbons) compared to gondoic acid (20 carbons).
Conversion of crop residues by black soldier fly (BSF) larvae:
BSF larvae were able to turn camelina seed cake (remaining after pressing out the oil) into valuable insect fats and proteins. The fat extracted from the larvae was found to have a composition very similar to those of coconut and palm kernel oil; it contained large amounts of the medium-chain length lauric acid (C12). Calculations indicate that by growing BSF larvae on diets containing 50% of camelina press cake, oil yields per hectare can be increased indirectly by about 20%. The insect route provides an additional way to obtain the desired MCFA, apart from chemical cleavage. Additionally, since the protein from the larvae has a very high nutritional value in food and feed, the resources are fully valorised.
Advances in FA chain scission chemistry:
Project partner Arkema is interested to find alternative processes and oil sources for their bio-based polyamides, currently sourced from imported castor oil. Camelina has been identified as a potential source of gondoic acid (C20:1, delta-11), while crambe, which is high in monounsaturated FA, could be a source of non-food oleic acid (C18:1, delta-9). Specific chain-scission reactions (oxidative cleavage, ethenolysis and cross-metathesis with acrylonitrile) have been evaluated to produce the expected molecules from gondoic and oleic acid. Some impurities present in the oils and esters are still strongly affecting the metathesis catalysts which currently makes the route more challenging.
Novel ruthenium catalysts to cleave FA chains into MCFA derivatives
Project partner Apeiron has developed a new, safe and straightforward process for preparing a specific family of olefin metathesis catalysts. One member of this family, UltraCat, has been designed for metathesis with ethylene (“ethenolysis”) – a process that allows scission of long-chain FA derivatives to MCFA products of high interest. Moreover, UltraCat exhibits a good reactivity profile in other metathesis reactions. A related member of this family is UltraNitroCat which is very efficient in metathesis reaction with acrylonitrile – one of the most difficult metathesis substrates. Both UltraCat and UltraNitroCat are now available from Strem and Merck (patents pending WO2017/055945 and WO2018/087678).
Innovative hydraulic fluids:
Project partners Arkema and CPST have used MCFA and side products of the FA chain scission chemistry to prepare two new classes of lubricating base oils for high-performance hydraulic fluids. One class, derivatized polyol esters, utilizes more than 90% feedstocks from crambe or camelina. Another class of basestocks, novel mono-unsaturated dibasic esters, may contain over 50% of materials derived from crambe or camelina. They combine excellent fluidity at low temperatures, remarkable resistance to heat thinning, outstanding additive solvency and thermal conductivity with acceptable oxidation stability and other lubricant properties. Optimised formulations with functional additives showed good performance in standard tests when compared to brand name commercial hydraulic fluids. Both project partners have filed a joint application at the European Patent Office (EPO) under EP3483233 and PCT WP19091786. The technology is available for licensing.
