9-Decenoic acid, methyl ester synthesis
- Product Name:9-Decenoic acid, methyl ester
- CAS Number:25601-41-6
- Molecular formula:C11H20O2
- Molecular Weight:184.28
Yield: 78%
Reaction Conditions:
Stage #1:Methyl oleate with tetraethylammonium iodide in toluene at 20; for 1 h;Inert atmosphere;Glovebox;
Stage #2:ethene with C50H59Br2Cl2N3O2SiW in toluene;benzene at 50; under 7600.51 Torr; for 18 h;Autoclave;Inert atmosphere;Reagent/catalyst;Concentration;
Steps:
10
Compounds according to the invention were tested in ethenolysis of methyl oleate.The substrate was purified using triethylaluminum (TEAI) according to methods known from WO 2014/139679 (XiMo). Methyl oleate was mixed with 700 ppmwt TEAI and the mixture was stirred at room temperature for 4 hours.In a nitrogen gas filled glovebox, fatty acid methyl ester was measured into 30 mL glass vials and mixed with the stock solution of triethylaluminum (23 %wt in toluene). The optimal triethylaluminum amount was determined previously and was found to be 700ppm. Mixtures were stirred at r.t. for 1 hour. Catalysts were added as a stock solution (0.01 M in benzene) The vial was placed into a stainless steel autoclave equipped with an alublock and was stirred at 50°C under 10 atm of ethylene gas overpressure for 18 hours. Five reactions were performed in the same autoclave with common gas space. The excess of ethylene was let out. From the reaction mixture 2.0 pi was taken out and diluted to 1.5 ml with n-pentane and analyzed by GCMS-FID, (Shimadzu 2010 Plus, column: Zebron ZB-35FIT INFERNO, 30 m x 0.25 mm x 0.25 pm.reaction with 12-rac was prepared in 250 ml_ scale as the catalyst was portioned to it as a powder due to its insolubilityQuantification of the liquid phase by GC indicated the conversion given in Table 3 below:Under comparable conditions, the ethenolysis of methyl oleate using the Mo analog of compound 4 resulted in a yield of 9-DAME of around 30 % and a total conversion of around 40 %
References:
VERBIO VEREINIGTE BIOENERGIE AG;ONDI, Levente;HEGEDüS, Csaba;BUCSAI, ágota;VARGA, Jeno;VAKULYA, Benedek;LORINCZ, Krisztian;GULYAS, Henrik;MEHDI, Hasan WO2020/239859, 2020, A1 Location in patent:Paragraph 00228-00232
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