Preparation of Acetonides from Soybean Oil, Methyl Soyate, and Fatty Esters

Biswas, Atanu; Sharma, Brajendra K.; Vermillion, Karl E.; Willett, J. L.; Cheng, H. N.

doi:10.1021/jf1026229

Cited by 12 publications

(5 citation statements)

References 28 publications

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“…Conversion of epoxide to the ketal product is well documented in the literature [26][27][28]. However, the use of strong acids along with acetone such as hydrochloric acid, sulfuric acid or Lewis acid BF 3 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Functional Evaluation of Soy Fatty Acid Methyl Ester Ketals as Bioplasticizers

Kandula

Stolp

Graß

et al. 2014

J Americ Oil Chem Soc

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A facile synthesis of the soy fatty acid methyl ester ketal has been accomplished using acetone in the presence of catalytic anhydrous ferric chloride starting from commercially available soy biodiesel (soy fatty acid methyl ester) after evaluating various synthetic procedures. The soy ketal product was fully characterized by nuclear magnetic resonance, infra‐red and chromatography. The physical and analytical properties of soy ketal as determined by thermogravimetric analysis, viscosity acid and saponification values are acceptable for plasticizer applications. Soy ketal was compounded with polyvinyl chloride for evaluation of plasticizer properties such as efficiency, gelation, viscosity, volatility, thickening/aging behavior and stability. The thickening and aging behaviors of the soy ketal bioplasticizer are better than those of petroleum‐based plasticizers such as diisononyl phthalate and diisononyl‐cyclohexane dicarboxylate, but they need improvement in the areas of thermal stability and water extractability.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Functional Evaluation of Soy Fatty Acid Methyl Ester Ketals as Bioplasticizers

Kandula

Stolp

Graß

et al. 2014

J Americ Oil Chem Soc

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“…Examples of acetonide formation include ketalization of EMO, EML and ESO methyl esters with acetone in the presence of catalytic FeCl 3 for 3-24 h at room temperature (Biswas et al, 2011;Kandula et al, 2014;Riley et al, 2015). The resulting acetonides were more suitable as solvents for dissolution of nonpolar as well F I G U R E 3 0 Azide-alkyne cycloaddition to give substituted 1,2,3-triazoles.…”

Section: Ketalizationmentioning

confidence: 99%

“…Examples of acetonide formation include ketalization of EMO, EML and ESO methyl esters with acetone in the presence of catalytic FeCl 3 for 3–24 h at room temperature (Biswas et al, 2011; Kandula et al, 2014; Riley et al, 2015). The resulting acetonides were more suitable as solvents for dissolution of nonpolar as well as polar substances than unmodified SBO methyl esters (Riley et al, 2015) and were more effective as bioplasticizers in PVC than petroleum‐based plasticizers (Kandula et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

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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“…32 A heterogeneous polymer network is developed during curing process due to the large difference in the reactivity of secondary epoxy in ESO and terminal epoxy in DGEBA, which leads to phase-separated network structure. The epoxy ring opening reaction has been employed to obtain ESO grafted with various chemical moieties including, diamine, 33 azide, 34 fatty acids (FAs), 11 allyl group, 35 acrylates 36 diester, 37 ketals, 38,39 and others. 40,41 An epoxy toughener superior to that of ESO is needed to significantly improve the fracture properties while maintaining processing ease and thermal properties.…”

Section: Introductionmentioning

confidence: 99%

Toughening Anhydride-Cured Epoxy Resins Using Fatty Alkyl-Anhydride-Grafted Epoxidized Soybean Oil

Yadav

Scala

et al. 2018

ACS Omega

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The aim of this work is to develop a series of advanced biobased tougheners for thermosetting epoxy resins suitable for high-performance applications. These bio-rubber (BR) tougheners were prepared via a one-step chemical modification of epoxidized soybean oil using biobased hexanoic anhydride. To investigate their toughening performance, these BR tougheners were blended with diglycidyl ether of bisphenol A epoxy monomers at various weight fractions and cured with anhydride hardeners. Significant improvements in fracture toughness properties, as well as minimal reductions in glass transition temperature (Tg), were observed. When 20 wt % of a BR toughener was utilized, the critical stress intensity factor and critical strain energy release rate of a thermosetting matrix were enhanced by >200 and >500%, respectively, whereas the Tg was reduced by only 20 °C. The phase-separated domains were evenly dispersed across the fracture surfaces as observed through scanning electron microscopy and atomic force microscopy. Moreover, domain sizes were demonstrated to be tunable within the micrometer range by altering the toughener molecular structure and weight fractions. These BR tougheners demonstrate the possibility of achieving toughness while having the thermal properties of standard bisphenol epoxy thermosetting resins.

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Preparation of Acetonides from Soybean Oil, Methyl Soyate, and Fatty Esters

Cited by 12 publications

References 28 publications

Synthesis and Functional Evaluation of Soy Fatty Acid Methyl Ester Ketals as Bioplasticizers

Synthesis and Functional Evaluation of Soy Fatty Acid Methyl Ester Ketals as Bioplasticizers

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

Toughening Anhydride-Cured Epoxy Resins Using Fatty Alkyl-Anhydride-Grafted Epoxidized Soybean Oil

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