Synthesis of N-Activated Aziridines of Long-Chain Fatty Acid Esters

Bottega, Diana P.; Martinelli, Márcia; Koetz, Mariana

doi:10.1055/s-0029-1218151

Cited by 4 publications

(2 citation statements)

References 13 publications

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“…Aziridines are another class of organic compounds that might be useful as plasticizers. Although various methods are available in the literature for making aziridines , an inexpensive synthetic procedure was adopted due to the end use application . Chloramine‐T (N‐chloro 4‐methylbenzenesulfonamide, sodium salt) is an inexpensive nitrogen source that can readily be converted to aziridine.…”

Section: Resultsmentioning

confidence: 99%

Functionalization of soy fatty acid alkyl esters as bioplasticizers

Kandula

Stolp

Graß

et al. 2015

Vinyl Additive Technology

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The combination of various functional groups, such as epoxy, acetoxy, methoxy, thiirane, and aziridine, on the fatty acyl chain of soy fatty acid alkyl esters have been synthesized and evaluated as plasticizers in poly(vinyl chloride) (PVC) applications. Numerous synthetic procedures, such as epoxidation, methoxylation, acetylation, thiiration, and aziridination, were used for synthesizing multifunctional soy fatty acid alkyl esters. Epoxidized soybean oil fatty acid alkyl ester served as the key intermediate for functionalization. Partial or complete ring opening of the epoxide by reacting with methanol and the subsequent etherification or acetylation of the hydroxyl function produced epoxy, alkoxy, and acetoxy derivatives. The nucleophilic substitution of epoxide with sulfur by reacting with ammonium thiocyanate produced thiirane and epoxy thiiranes. Although the aziridine derivatives were synthesized by reacting unsaturated fatty acid alkyl esters with chloramine-T, the compounds were fully characterized and their physical and analytical properties were determined. The high viscosity and darker color of aziridine and thiirane derivatives limit their usefulness, whereas the physical properties of the other derivatives were acceptable. The plasticizer evaluation of methoxy and acetoxy soy fatty acid esters (methyl and n-butyl) demonstrated good compatibility with PVC, high efficiency (Shore hardness), and gelling properties were comparable to commercial plasticizer, di-isoonyl phthalate. The abundant availability and cost-effectiveness of starting materials and the readily adoptable chemical processes make the fatty acid ester derivatives viable bioplasticizers to replace the fossil fuel-derived phthalates. J. VINYL ADDIT. TECH-

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Section: Resultsmentioning

confidence: 99%

Functionalization of soy fatty acid alkyl esters as bioplasticizers

Kandula

Stolp

Graß

et al. 2015

Vinyl Additive Technology

View full text Add to dashboard Cite

show abstract

“…113 Loreto and co-workers have described a route to spiroaziridine-oxindoles, 114 and the Bottega group have studied the aziridination of unsaturated fatty acids. 115…”

Section: Scheme 29 Scheme 30mentioning

confidence: 99%