Ketalization of epoxidized methyl oleate using acidic resins

Pérez, William A.; Echeverri, David A.; Ríos, Luis Alberto

doi:10.1002/jctb.5030

Cited by 5 publications

(10 citation statements)

References 28 publications

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“…These values correspond to selectivities to epoxides of 75% and 66%, respectively. The acid strength of both resins is similar, however, their morphology is different since Amberlyst 15 has a macroreticular form while Amberlite IR‐120 is gel type 23 . Thus, Amberlyst‐15 maintains its granular form and porosity in solution with the most of acid sites located on the external surface 23–25 .…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, once epoxides are formed, they can be easily protonated and opened by water to form secondary products such as glycols. On the other hand, Amberlite IR‐120 swells depending on the solvent polarity with the acid sites immersed in the gel structure 23 . Once the epoxides are formed, the contact of them and the acid sites is hindered due to the bulkiness of fatty molecule.…”

Section: Resultsmentioning

confidence: 99%

“…The acid strength of both resins is similar, however, their morphology is different since Amberlyst 15 has a macroreticular form while Amberlite IR-120 is gel type. 23 Thus, Amberlyst-15 maintains its granular form and porosity in solution with the most of acid sites located on the external surface. [23][24][25] Therefore, once epoxides are formed, they can be easily protonated and opened by water to form secondary products such as glycols.…”

Section: Epoxidation and Carbonation Of Me-rammentioning

confidence: 99%

“…23 Thus, Amberlyst-15 maintains its granular form and porosity in solution with the most of acid sites located on the external surface. [23][24][25] Therefore, once epoxides are formed, they can be easily protonated and opened by water to form secondary products such as glycols. On the other hand, Amberlite IR-120 swells depending on the solvent polarity with the acid sites immersed in the gel structure.…”

Section: Epoxidation and Carbonation Of Me-rammentioning

confidence: 99%

“…On the other hand, Amberlite IR-120 swells depending on the solvent polarity with the acid sites immersed in the gel structure. 23 Once the epoxides are formed, the contact of them and the acid sites is hindered due to the bulkiness of fatty molecule. Therefore, secondary reactions of epoxides decrease using Amberlite IR-120.…”

Section: Epoxidation and Carbonation Of Me-rammentioning

confidence: 99%

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Synthesis of a new bifunctional molecule based on castor oil and CO₂ useful for polyurethanes

Cortés

Echeverri

Gomez

et al. 2022

J of Applied Polymer Sci

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A new bifunctional biobased molecule, the carbonated methyl ester of ricinoleic acid maleate (CME‐RAM), useful for polyurethanes, was obtained from castor oil and CO2. This molecule bears carbonate and maleate functionalities that can participate, respectively, in aza‐Michael and aminolysis reactions. Maleate moieties are strong Michael acceptors and they were introduced into the fatty molecule using mild conditions. The synthetic steps include maleinization of castor oil followed by the simultaneous esterification and transesterification at 60°C. The subsequent stages were the epoxidation with acidic resins and the carbonation with CO2. The best results for epoxidation were obtained using Amberlite IR‐120 as catalyst at 48°C (84% conversion of double bonds). The carbonation of the oxirane ring with CO2 at 130°C, 6 MPa CO2 and 6 h reaction afforded 98% conversion of epoxides. It was demonstrated that aza‐Michael reaction of maleate groups was faster than aminolysis of carbonate groups, using hexylamine as a model molecule. CME‐RAM was oligomerized with ethylenediamine and used in the formulation of a conventional rigid polyurethane. Petrochemical polyol and isocyanate can be partially replaced by this bio‐based oligomer, producing a rigid material with a high percentage of green component and good mechanical properties.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Epoxidation and Carbonation Of Me-rammentioning

confidence: 99%

Section: Epoxidation and Carbonation Of Me-rammentioning

confidence: 99%

Section: Epoxidation and Carbonation Of Me-rammentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of a new bifunctional molecule based on castor oil and CO₂ useful for polyurethanes

Cortés

Echeverri

Gomez

et al. 2022

J of Applied Polymer Sci

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A review of fatty epoxide ring opening reactions: Chemistry, recent advances, and applications

Moser

Cermak

Doll

et al. 2022

J Americ Oil Chem Soc

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Fatty epoxides are produced from the corresponding alkenes by oxidation in the presence of peracids or other oxidants. The classic method is the Prilezhaev epoxidation in which peracids are generated by in situ oxidation of formic or acetic acids with hydrogen peroxide. Epoxidized vegetable oils and esters are used directly as biobased plasticizers and stabilizers for poly(vinyl chloride) or as important platform chemicals for the oleochemical industry. Nucleophilic attack at the oxirane moiety affords a variety of ring opened monomeric or polymeric products, which in many cases undergo further synthetic modification to yield finished products. The most common nucleophiles include water, alcohols, carboxylic acids, acid anhydrides, and amines, although numerous others can also lead to valuable functionalized fatty derivatives. This review summarizes the chemistry of fatty epoxide ring opening reactions as well as applications of the resultant products. Literature from the last 20 years will be emphasized, although older publications of particular significance will be included. Important applications include biobased lubricants as well as polyols for subsequent production of polyurethanes. In addition, ring-opening reactions hitherto unreported on fatty oxiranes will be suggested to facilitate further advancements in the chemistry and utility of fatty epoxides. Finally, interest in fatty epoxides and their consequent products will continue to grow due to the simplicity, efficiency, and versatility of oxirane formation and ring opening as well as the continued societal transition away from petroleum to a sustainable, circular, low-carbon, and biobased economy.

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Synthesis of environment‐friendly, sustainable, and nontoxic bio‐lubricants: A critical review of advances and a path forward

Sancheti

Yadav

2022

Biofuels Bioprod Bioref

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Carbon neutral biosources are sought for the protection of the environment and to meet the energy needs of the growing population. For instance, lubricants are required in huge quantities. Synthesis of environment-friendly, sustainable and non-toxic bio-lubricants from renewable and bio-degradable feedstocks such as vegetable oils and animal fats will be most desirable. The thermal stability and lower volatility of these triglycerides make them suitable as precursors for lubricants. This review briefly covers the chemical modifications required to transform plant-and animal-based triglycerides into efficient biolubricants. Chemical modifications are required to improve one or more physicochemical or tribological properties of bio-lubricants such as low-temperature flow properties or the oxidation stability of fatty acids/oils for different applications. The use of heterogeneous catalysts makes the processes clean. The relationship between their molecular structures, physicochemical properties and lubrication performance is reviewed. Additives such as antioxidants, sulfides, phosphates, metal and metal oxide nanoparticles, and ionic liquids are used to enhance the lubricant properties. With proper modifications in a base oil, support and additives, bio-lubricants can perform similar to or even better than conventional lubricants. A further advantage is that they can be easily adapted using existing infrastructure and lubricant formulations.

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Ketalization of epoxidized methyl oleate using acidic resins

Cited by 5 publications

References 28 publications

Synthesis of a new bifunctional molecule based on castor oil and CO₂ useful for polyurethanes

Synthesis of a new bifunctional molecule based on castor oil and CO₂ useful for polyurethanes

A review of fatty epoxide ring opening reactions: Chemistry, recent advances, and applications

Synthesis of environment‐friendly, sustainable, and nontoxic bio‐lubricants: A critical review of advances and a path forward

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Ketalization of epoxidized methyl oleate using acidic resins

Cited by 5 publications

References 28 publications

Synthesis of a new bifunctional molecule based on castor oil and CO2 useful for polyurethanes

Synthesis of a new bifunctional molecule based on castor oil and CO2 useful for polyurethanes

A review of fatty epoxide ring opening reactions: Chemistry, recent advances, and applications

Synthesis of environment‐friendly, sustainable, and nontoxic bio‐lubricants: A critical review of advances and a path forward

Contact Info

Product

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About

Synthesis of a new bifunctional molecule based on castor oil and CO₂ useful for polyurethanes

Synthesis of a new bifunctional molecule based on castor oil and CO₂ useful for polyurethanes