Aziridination of Methyl Long-chain Alkenoates Using Chloramine-T

Rauf, Abdul; Ahmad, Shafi

doi:10.3184/0308234054506802

Cited by 7 publications

(4 citation statements)

References 29 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 [35], an inexpensive synthetic procedure was adopted due to the end use application [36,37]. Chloramine-T (N-chloro 4-methylbenzenesulfonamide, sodium salt) is an inexpensive nitrogen source that can readily be converted to aziridine.…”

Section: Synthesis Of N-tosyl Aziridine Soy Fatty Acid Methylmentioning

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: Synthesis Of N-tosyl Aziridine Soy Fatty Acid Methylmentioning

confidence: 99%

Functionalization of soy fatty acid alkyl esters as bioplasticizers

Kandula

Stolp

Graß

et al. 2015

Vinyl Additive Technology

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“…9 Recently, chloramine-T, in the presence of iodine as catalyst, has been proposed as an alternative nitrogen source for the introduction of a substituted aziridine ring into an unsaturated long chain fatty acid. 10 Thus, commercially available methyl oleate and methyl (9Z,12R)-12-hydroxyoctadec-9-enoate (methyl ricinoleate), isolated from the seed oil of Ricinus communis, were converted into their corresponding aziridine derivatives in 64% and 81% yield, respectively (Scheme 1, path c).…”

mentioning

confidence: 99%

“…The identity of the aziridine derivative 1 was confirmed by comparison of the 1 H NMR spectrum with that described in the literature. 10 The spectrum of purified 1 (Figure 1 trans-product. The 1 H NMR spectra of the crude products revealed that there was preferential (80-90%) formation of the cis-product.…”

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confidence: 99%

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

Bottega¹,

Martinelli²,

Koetz³

2009

Synthesis

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An alternative one-step synthesis of N-activated aziridines of naturally occurring fatty acid esters from olive oil and sunflower oil has been achieved. N-Tosylaziridine derivatives were obtained in yields ranging from 8.5 to 97.5%. Methyl cis-and trans-8-(3-octyl-1-tosylaziridin-2-yl)octanoates were formed with transesterified olive oil as substrate, and methyl cis-and trans-(Z)-11-(3pentyl-1-tosylaziridin-2-yl)undec-9-enoates were produced when transesterified sunflower oil was the substrate.

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“…The present work is in continuation of our study on the synthesis of heterocycles from such acids. Tetrazoles, [27,28] pyrazolines [29], tetrazines [30,31], spiro [oxathiolane-2,29-dihydrotetrazoles] [32], aziridines [33], and triazines [34] have been previously prepared in our lab. Cyanoethoxy and morpholine derivatives of hydroxy long-chain acids [35] and fatty esters [36] showed significant antifungal and antibacterial activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antibacterial and Antifungal Activity of Some Novel 3,5‐Disubstituted‐1H‐1,2,4‐triazoles

Sharma

Gangal

Rauf³

et al. 2008

Archiv der Pharmazie

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A rapid and efficient one-pot condensation reaction of long-chain alkyl and alkenyl acid hydrazides and nitriles was carried out to afford 3,5-disubstituted-1H-1,2,4-triazoles. The compounds 5a-o were screened for in-vitro antibacterial activity against the representative panel of two Gram-positive and two Gram-negative bacteria. All the synthesized compounds were also tested for their inhibitory action against five strains of fungi. The various compounds show potent inhibitory action against test organisms. The compounds 5a-o were characterized on the basis of elemental analysis and spectral data.

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Aziridination of Methyl Long-chain Alkenoates Using Chloramine-T

Cited by 7 publications

References 29 publications

Functionalization of soy fatty acid alkyl esters as bioplasticizers

Functionalization of soy fatty acid alkyl esters as bioplasticizers

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

Synthesis, Antibacterial and Antifungal Activity of Some Novel 3,5‐Disubstituted‐1H‐1,2,4‐triazoles

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