Processing microalgae: beyond lipids

Cross-metathesis approach to produce precursors of nylon 12 and nylon 13 from microalgae

“…Thus these reaction conditions were adopted for the subsequent studies (Table 6). The base additive is essential in this catalyst system, and 30 mol% of potassium tert-butoxide was sufficient to ensure the full reaction conversion (entries 1 and 2 vs. [3][4][5][6][7][8][9][10][11]. The catalyst loading of >2 mol% was found essential for good conversion (entries 3-5; 8-10).…”

“…While the starting material, oleic acid, can be supplied economically from many renewable resources, our method would be particularly useful if a crude lipid extracts from microalgae could be directly used. [4][5][6] Thus, the cross-metathesis reaction was tested using a mixture of fatty acid methyl esters (FAMEs) obtained from algal biomass by our recently developed reactive-extraction technology which enables recovery of algal lipids as FAMEs in a single step. 30 We are pleased to nd that both cross-metathesis with acrylonitrile and allyl cyanide proceeded smoothly consuming only unsaturated FAMEs and leaving the saturated FAMEs behind (Table 7 and Fig.…”

“…3 As such, synthetic approaches that use natural fatty acids and esters from plant-or algae-derived feedstocks are especially attractive. [4][5][6] Among the natural fatty acids, oleic acid is the predominant component of lipids in a large variety of vegetable oils (e.g. soy or canola) as well as oleaginous microorganisms such as algae.…”

Efficient Conversion of Renewable Unsaturated Fatty Acid Methyl Esters by Cross-Metathesis with Eugenol

“…1−11 One of the recent promising applications in the olefin metathesis is the utilization of renewable bio-source materials to complement or replace petroleum-based specialty chemicals. 12−16 In particular, CM of unsaturated fatty acid esters (shown in Scheme 1), which are obtained from plant oils or algae-derived feedstocks, 1−3,17−20 has been considered as a promising subject in terms of both green chemistry and oleochemistry. 12−16,21−41 Methyl oleate (MO) is the predominant component of fatty acid methyl esters of the triglycerides in many vegetable oils, such as olive, canola oil, or Jatropha oil, 17−20 and is usually obtained from the transesterification of vegetable oils with alcohol.…”

Toward Sustainable Synthesis of PA12 (Nylon-12) Precursor from Oleic Acid Using Ring-Closing Metathesis

“…There has been increasing appreciation for the use of renewable biosourced materials to complement or replace petroleum-based specialty chemicals. , In particular, olefin metathesis is regarded as an effective tool for refining biobased lipids for this purpose. , In this context, we have recently reported , new approaches for synthesizing high-order polyamide (PA, nylon) precursors from oleic acid ( 1 ), an abundant feedstock available from various renewable sources. One of our approaches involves three steps using ring-closing metathesis to provide macrolactams having carbon length ranging from 11 to 13, monomers of PA11–13 (Scheme ).…”