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Le, Duy, et al. ACS omega, 2018, 3(9), 11041-11049.
The cross-metathesis (CM) reaction of renewable fatty acid methyl esters, such as methyl oleate (MO), methyl petroselinate (MP), and methyl erucate (ME, methyl cis-13-docosenoate), with eugenol (UG) can be achieved through a ruthenium carbene catalyst Successfully carried out under environmentally friendly conditions.
Cross-Metathesis Reaction of Fatty Acid Methyl Esters
· The second generation Grubbs catalyst [RuCl2(PCy3)(H2IMes)(CHPh)], known as G2, was carefully weighed (1.7 mg, 0.1 mol %, 0.0020 mmol) in a 10 mL vial while under a nitrogen atmosphere.
· Fatty acid methyl esters (MO (593 mg, 2.00 mmol), ME (706 mg, 2.00 mmol), MP (593 mg, 2.00 mmol), or MU (397 mg, 2.00 mmol)) along with UG (3.284 g, 20.0 mmol, 10 equiv) were dissolved in a solvent and then quickly added to the vial containing the catalyst. The mixture was stirred at 50 °C for 10 minutes before being filtered through a packed column of Celite.
· Methyl heptadecanoate (10 mg) was included in the filtrate as an internal standard for GC analysis. The resulting mixture was then analyzed using gas chromatography equipped with flame ionization detection (GC-FID) and gas chromatography mass spectrometry (GC-MS).
Stempfle, Florian, et al. Green chemistry, 2014, 16(4), 2008-2014.
Using methyl cis-13-docosenoate as the starting material, long-chain linear aliphatic diester monomer (dimethyl-1,23-tricosanedioate) can be obtained through isomerization alkoxycarbonylation. The prepared monomers are further subjected to a polycondensation reaction to obtain polyesters, which can be used for film extrusion or blending with thermoplastics.
Monomer synthesis and polycondensation
· Methyl erucate (175 mL) was dissolved in 500 mL of methanol and transferred into the pressure reactor under a nitrogen atmosphere using a cannula.
· A solution of the catalyst precursor [(dtbpx)Pd(OTf)2] (687 mg, 0.86 mmol) in another 50 mL of methanol was then added to the reactor, which was pressurized with 20 bar of CO and heated to 90 °C for 120 h reaction.
· The obtained crude product was dissolved, filtered, solvent removed under vacuum, and recrystallized to obtain pure 1,23-eicosanedioic acid dimethyl ester (96.0 g, yield 54%, purity 99.6%).
· The monomers (20.0 mmol of diethyl-1,23-tricosanedioate and 20.0 mmol of the corresponding α,ω-diol) were placed in the reaction vessel under a static argon atmosphere and melted by heating to 120 °C.
· A 0.6 mL aliquot of a 0.028 M titanium(IV) butoxide solution in toluene was then added, and the temperature was gradually increased to 200 °C over 8 hours. The polymer melt was stirred at this temperature for approximately 16 hours under reduced pressure (0.01 mbar).
What is the melting point of cis-13-docosenoic acidmethyl ester?
The melting point of cis-13-docosenoic acidmethyl ester is -1.16-1.20℃.
What is the solubility of cis-13-docosenoic acidmethyl ester in ethanol?
The solubility of cis-13-docosenoic acidmethyl ester in ethanol is 100mg/ml.
What is the main application of cis-13-docosenoic acidmethyl ester?
cis-13-Docosenoic acidmethyl ester is mainly used for the production of erucamide, erucamide and other derivatives.
What is the stability of cis-13-docosenoic acidmethyl ester?
cis-13-Docosenoic acidmethyl ester is sensitive to light and needs to be stored in a brown bottle in the dark.
What is the form of cis-13-docosenoic acidmethyl ester?
At room temperature, cis-13-docosenoic acidmethyl ester exists in the form of liquid.
What is the flash point of cis-13-docosenoic acidmethyl ester?
The flash point of cis-13-docosenoic acidmethyl ester is 33℃.
What is the molecular formula of cis-13-docosenoic acidmethyl ester?
The molecular formula of cis-13-docosenoic acidmethyl ester is C23H44O2.
What is the boiling point of cis-13-docosenoic acidmethyl ester?
The boiling point of cis-13-docosenoic acidmethyl ester is 172-175℃.
What is the EC number of cis-13-docosenoic acidmethyl ester?
The EC number of cis-13-docosenoic acidmethyl ester is 214-305-3.
What are the storage conditions of cis-13-docosenoic acidmethyl ester?
cis-13-Docosenoic acidmethyl ester needs to be sealed and stored in the environment of 2-8℃ away from light.
