125412-22-8Relevant articles and documents
Melting points and viscosities of fatty acid esters that are potential targets for engineered oilseed
Yao, Linxing,Hammond, Earl,Wang, Tong
, p. 77 - 82 (2008)
Our previous isolation of branched-chain fatty acid (BCFA) methyl esters from lanolin was improved and scaled up. Also, oleate esters of isopropanol, oleyl alcohol and normal alcohols of 1-12 carbons chain lengths were prepared. Esters were made by interesterification with sodium alcoholates and by esterification with Candida antarctica lipase. It proved easier to obtain pure esters by the enzymatic synthesis. Melting points and viscosities over the range of 0-70 °C were determined in order to better identify potential lubricant targets that might be produced by genetically modified oilseed crops. Isopropyl and butyl oleate have melting points of -33 and -32 °C, respectively and viscosities that range from ~17 cp (0 °C) to ~2.5 cp (70 °C). They should have suitable stability for lubricants. BCFA esters had viscosities similar to their straight chain analogs. Viscosities increased with alcohol chain length and decreased with temperature. The dependence of viscosity on temperature was fit with an equation based on Erying's rate equation. Some esters with branched acid or branched alcohol moieties, and some oleate esters might be utilized as biolubricants or biofuels on the basis of their melting points and viscosities.
Guanidine based task specific ionic liquids for the synthesis of biolubricant range esters under solvent-free condition
Porwal, Jyoti,Kumar, Subodh,Kaul, Savita,Jain, Suman L.
, p. 93640 - 93644 (2016)
Guanidine-based task specific ionic liquids (ILs) were synthesized from the reaction of 1,1,3,3-tetramethyl guanidine with protic acids and used for the synthesis of higher alcohol esters of fatty acids as biolubes under solvent free condition. The synthesized 1,1,3,3-tetramethylguanidinium hydrogen sulphate (TMG·HSO4) was found to be most effective among the different ILs including 1,1,3,3-tetramethylguanidinium acetate (TMG·Ac), 1,1,3,3-tetramethylguanidinium hydrogen phosphate (TMG·H2PO4) and 1,1,3,3-tetramethylguanidinium trifluoro acetate (TMG·TFA). The effect of various reaction parameters such as reaction temperature, reaction time, catalyst amount etc. has been studied. After completion the reaction the esterification product was isolated and the recovered IL was reused for several runs without loss in catalytic activity.
Preparation of Musk-Smelling Macrocyclic Lactones from Biomass: Looking for the Optimal Substrate Combination
Sytniczuk, Adrian,Leszczyńska, Agnieszka,Kajetanowicz, Anna,Grela, Karol
, p. 3157 - 3166 (2018/09/14)
Macrocyclic musk belongs to a well-known and valued class of the fragrance family. Originally, natural musks were obtained from rectal musk glands which often led to the death of the animals. Recently, a lot of effort was invested to obtain such macrocycles in a synthetic way. This research presents a study on the preparation of macrocyclic lactones with the musk scent by ring-closing metathesis (RCM) using biomass-derived starting materials: oleic and 9-decenoic acid. An experimental rule correlating the C–C double bond substitution pattern in the starting diene and the yield for the RCM macrocyclization was proposed.
Solvent- and base-free synthesis of wax esters from fatty acid methyl esters by consecutive one-pot, two-step catalysis
Nguyen,Raffa,Morin,Desset,Capet,Nardello-Rataj,Dumeignil,Gauvin
supporting information, p. 5665 - 5673 (2017/12/06)
The one-pot, two-step synthesis of wax esters was successfully conducted by consecutive homogeneous ruthenium-catalysed hydrogenation-dehydrogenation reactions of fatty acid methyl esters, in the absence of solvent and of base additive. Under optimized conditions, excellent conversion and selectivity were reached. Furthermore, physicochemical investigations revealed that the resulting compounds display properties similar to benchmark commercial products extracted from natural sources of lesser availability compared to the herein considered bioresources, making this chemical route very promising regarding further potential industrial implementation.
