Synthesis of Glycerol Monostearate with High Purity

Yu, Che; Lee, Youn-Sik; Cheon, Byung Soo; Lee, Sangeun

doi:10.5012/bkcs.2003.24.8.1229

Cited by 58 publications

(10 citation statements)

References 11 publications

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“…In several reports, however, the authors have indeed addressed the purity status of their products adequately by critical evaluation after separation by the use of argentation chromatography. 40 The final step involved deprotection of the isopropylidene protective group and was readily brought about by treatment with acidic Amberlyst-15 ion-exchange resin in gently refluxing ethanol 41 to accomplish the target molecule MEL 3 in a 91% yield of satisfactory chemical and stereoisomeric purity. Our previous results involving the use of the head piece 4 in the synthesis of MELs 1 and 2 18 along with the quite comparable methodology strongly imply that the excellent enantio-and diastereopurity in terms of the two chiral centers were retained in the MEL 3 synthesis.…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Synthesis of Methoxylated Ether Lipids: Total Synthesis of n-3 Polyunsaturated Docosahexaenoic Acid-Like Methoxylated Ether Lipid

et al. 2022

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The first total synthesis of a docosahexaenoic acid (DHA)-like methoxylated ether lipid (MEL) is reported. This compound constitutes an all-cis methylene skipped hexaene framework identical to that present in DHA, the well-known omega-3 polyunsaturated fatty acid. The polyene C22 hydrocarbon chain, bearing a methoxyl group in the 2-position and Rconfiguration at the resulting chiral center, is attached by an ether linkage to the pro-S hydroxymethyl group (sn-1 position) of a glycerol backbone. The asymmetric synthesis is highly convergent and based on the polyacetylene approach involving iterative copper-promoted coupling reactions of propargyl bromides with terminal alkynes and semihydrogenation of the resulting hexayne. Starting from enantiopure R-solketal and racemic epichlorohydrin, the targeted MEL was accomplished in an 8.2% yield over eight steps (longest linear sequence) involving an enantio-and diastereopure glyceryl glycidyl ether key C6-building blocks from which the polyynes were constructed.

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Section: Resultsmentioning

confidence: 99%

Asymmetric Synthesis of Methoxylated Ether Lipids: Total Synthesis of n-3 Polyunsaturated Docosahexaenoic Acid-Like Methoxylated Ether Lipid

et al. 2022

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“…Triacetin (purity >99%), diacetin (purity 50%), and molecular sieves 5 Å were purchased from Fluka (Seelze, Germany). Monoacetin and solketalacetin were synthesized via a previously reported method (purity >95%), , and Purolite PD 206 was obtained from Purolite Co. (USA). Methanol and 2-ethyl-1-hexanol was purchased from Merck Co. (Germany).…”

Section: Methodsmentioning

confidence: 99%

Optimization of Solketalacetin Synthesis as a Green Fuel Additive from Ketalization of Monoacetin with Acetone

Gorji

Ghaziaskar

2016

Ind. Eng. Chem. Res.

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An economical and easy to scale up method for glycerol conversion to solketalacetin (i.e., (2,2-dimethyl-1,3-dioxolan-4-yl)methyl acetate) as a valuable fuel additive is described, for the first time. Monoacetin was synthesized by reacting glycerol with acetic acid, and then solketalacetin was produced from the reaction of monoacetin with acetone using Purolite PD 206 as a catalyst. The central composite design was employed for the experimental design and then response surface methodology was used for the optimization of variables for the second stage of the reaction. The optimum operating conditions for the second stage of the reaction were as follows: acetone to monoacetin mole ratio, 5; reaction temperature, 20 °C; pressure, 45 bar; flow rate, 0.2 mL•min −1 ; and catalyst, 2.0 g. Yield of the second stage of the reaction at the experimental design conditions and at the acetone to monoacetin mole ratio of 9 was obtained as 69% and 100%, respectively.

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“…Based on the analysis of 1 H-NMR results of IGA, it was shown by the presence of peaks 1 and 2, which were geminal methyl groups exhibiting chemical shifts δ 1.36 and δ 1.42 ppm from the -CCH3CH3 proton with a singlet signal appearance. The proton peak on the carbon atom of the geminal methyl group (-CH3) was also visible at a chemical shift of δ 1.36 ppm with a singlet signal appearance in the synthesis of IGA with a purity of 99% and a yield of 97% [14]. The peak shift patterns of 1 and 2 are located in the upfield or shielded region because geminal methyl groups were not bonded to electronegative atoms.…”

Section: Ridlo Et Almentioning

confidence: 98%

“…This suggests the possibility of a cyclic reaction leading to the formation of IGA and the presence of a proton from the chiral centre formed in the cyclic chain. Furthermore, the absorption of proton peaks at a shift of δ 4.32 ppm with a multiplet signal appearance indicates the presence of protons on the chiral centre atom [14].…”

Section: Ridlo Et Almentioning

confidence: 99%

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Synthesis and Characterization of Isopropylidene Glycerol Acetate and Isopropylidene Glycerol Propanoate Compounds

Ridlo,

Choirunnisa,

Rahmawati

et al. 2023

Indones. J. Chem. Stud.

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Isopropylidene Glycerol Acetate (IGA) and Isopropylidene Glycerol Propanoate (IGP) as ester compounds using acetic and propanoic acids have been synthesized, characterized, and studied for their antibacterial properties. The IGA was synthesized from ethyl acetate (EtOAc) and 1,2-O-isopropyliden glycerol (IPG) with a mole ratio of 1:8 through a transesterification reaction. Meanwhile, the IGP was synthesized using ethyl propanoate (EP) with the same ratio and method as IGA. All materials in this study were identified using FT-IR, GC-MS, 1H-NMR, and 13C-NMR. The characterization results indicated that the compounds of EP, IPG, IGA, and IGP had been successfully formed and identified. It was also revealed that the compounds of EP, IPG, IGA, and IGP were successfully synthesized with yields of 37.72, 27.78, 70.11, and 63.83%, respectively. The antibacterial activity test revealed that neither IGA nor IGP inhibited the growth of Staphylococcus aureus or Escherichia coli at concentrations of 62.5; 125; 250; 500; and 1000 ppm. Therefore, it was asserted that ester compounds synthesized with short-chain carboxylic acids, such as propanoic and acetic acids, lacked antibacterial properties.

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Synthesis of Glycerol Monostearate with High Purity

Cited by 58 publications

References 11 publications

Asymmetric Synthesis of Methoxylated Ether Lipids: Total Synthesis of n-3 Polyunsaturated Docosahexaenoic Acid-Like Methoxylated Ether Lipid

Asymmetric Synthesis of Methoxylated Ether Lipids: Total Synthesis of n-3 Polyunsaturated Docosahexaenoic Acid-Like Methoxylated Ether Lipid

Optimization of Solketalacetin Synthesis as a Green Fuel Additive from Ketalization of Monoacetin with Acetone

Synthesis and Characterization of Isopropylidene Glycerol Acetate and Isopropylidene Glycerol Propanoate Compounds

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