Infrared Absorption Spectra of Some Epoxy Compounds

Shreve, O. D.; Heether, M. R.; Knight, H. B.; Swern, Daniel

doi:10.1021/ac60050a014

Cited by 118 publications

(41 citation statements)

References 13 publications

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“…The band at 1024 cm -1 could involve stretching of the C-O bond, as carbohydrates have many bands in this region [6]. The weak band at 856 cm -1 is proposed to be characteristic of the O-O linkage in hydroperoxides, even though its lack of intensity limits its usefulness [15]. The band at 721 cm -1 , similar to the one observed in the spectrum of fatty acids and triglycerides, could be assigned to the CH 2 rocking mode [9].…”

Section: Resultsmentioning

confidence: 99%

Spectroscopic Investigation of the Cashew Nut Kernel (Anacardium occidentale)

Barua¹,

Hazarika²,

Hussain³

et al. 2008

TOFSJ

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Fourier transform infrared and Fourier transform Raman spectra of the kernel of the cashew nut (Anacardium occidentale) are presented. Based on the correlations with the infrared spectra of its individual components and other compounds already published, assignments of the observed bands have been done. The infrared spectrum is shown to be very similar to that of triolein, a triglyceride of oleic acid a characteristic useful in reducing the low-density lipoprotein (LDL) cholesterol level of the person consuming it.

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Section: Resultsmentioning

confidence: 99%

Spectroscopic Investigation of the Cashew Nut Kernel (Anacardium occidentale)

Barua¹,

Hazarika²,

Hussain³

et al. 2008

TOFSJ

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“…22), 898 (C-C asymmetrical stretching of epoxy ring 21 ), 847, 834 and 818 ("12 micron band", typical of epoxy ring 21,22 ), and 719 (CH 2 rocking motions, characteristic for at least four linearly connected CH 2 groups). 1 H NMR (400 MHz, CDCl 3 ; d, in ppm): 2.9-3.2 (methine protons of the epoxy groups), 2.28-2.43 (a-CH 2 adjacent to -COOH), 1.72-1.90 (CH 2 protons between the epoxy groups), 1.60-1.72 (CH 2 b to -COOH), 1.45-1.60 (CH 2 a to the epoxy groups), 1.20-1.45 (protons of other methylene groups), 0.85-1.12 (protons of methyl groups).…”

Section: Methodsmentioning

confidence: 99%

“…The resulting mixture was bubbled with nitrogen for 2 min while stirring at 300 rpm and heating to 80 C. The reaction mixture was stirred at 80 C for 53 min to give a light green, homogeneous, and viscous resin. FTIR (neat, in cm À1 ): 3445 cm À1 (OH stretching), 2952 and 2871 (CH 3 stretching), 2923 and 2853 (CH 2 stretching), 1730 (ester carbonyl stretching), 1711 (-COOH carbonyl stretching), 1461 and 1378 (CH 2 bending), 1246 (ester C-O stretching), 1173 and 1112 (ester C-O-C stretching), 1073 and 1023 (C-OH stretching), 842 and 823 ("12 micron band" of epoxy ring 21,22 ).…”

Section: Methodsmentioning

confidence: 99%

Pressure-sensitive adhesives based on soybean fatty acids

2014

RSC Adv.

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A new class of renewable pressure-sensitive adhesive (PSA) designed and developed from soybean oil was reported in this study. Soybean oil was epoxidized and hydrolysed selectively on the ester groups to afford a mixture of epoxidized fatty acids (EFAs) which were characterized by FTIR and 1 H NMR spectroscopy. The EFA mixture without further purification was then polymerized directly in the presence and absence of a small amount of dicarboxylic acid compounds to afford hydroxyl-functionalized polymers. The peel strength, loop tack, shear strength and viscoelastic properties of the resulting (co)polymers revealed that the (co)polymers were suitable for PSA applications. The new PSAs could be fully bio-based and potentially biodegradable, and their preparation and application did not require the use of an organic solvent or a toxic chemical, thus being environmentally friendly.

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“…Experiments in which ['80]13-hydroperoxylinolenic acid was the substrate showed that only one of the hydroperoxy oxygen atoms was retained in the product. IR spectroscopy revealed absorptions at 1740 cm-' (ester carbonyl), 1700 and 1679 cm-' (a,f3-unsaturated ketone), 1635 cm-' (double bond a,f3 to a carbonyl), 980 cm-' (trans unsaturation), and 885 cm-' (trans epoxide) (14). NMR shifts were virtually identical to those reported by Gardner et al (4) for a mixture of 9,10-trans-epoxy-13-oxo-trans-11-and 12,13-trans-epoxy-9-oxo-trans-10-octadecenoic acids: 62.28 (t, methylene a to ester carbonyl), 62.93 (m, 1 H, epoxide proton a to methylene), 63.23 (dd, 1 H, epoxide proton a to a double bond), 66.45 (dd, 1 H, olefinic proton a to epoxide), 66.40 (s, 1 H, olefinic proton a to carbonyl), 62.51 (t, methylene a to conjugated carbonyl), multiplet centered on 65.44 (2 H, olefinic protons), 62.03 (m, methylene a to methyl and a to unsaturation).…”

Section: Identification Of Pentane or Pentenementioning

confidence: 99%

Metabolism of Fatty Acid Hydroperoxides by Chlorella pyrenoidosa

Vick¹,

Zimmerman²

1989

Plant Physiol.

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The green alga Chlorella pyrenoidosa was examined for its ability to metabolize 13-hydroperoxylinoleic and 13-hydroperoxylinolenic acids. The study showed that Chlorella extracts possessed hydroperoxide dehydrase and other enzymes of the jasmonic acid pathway. However, under normal laboratory conditions for culture growth, neither jasmonic acid nor metabolites of the jasmonic acid pathway were present in Chlorella. In vitro enzyme studies also revealed the presence of hydroperoxide lyase activity that cleaved 13-hydroperoxylinoleic or 13-hydroperoxylinolenic acid into two products, 13-oxo-cis-9,trans-11-tridecadienoic acid and pentane (from linoleic acid) or pentene (from linolenic acid). The lyase was heat-labile, insensitive to 50 millimolar KCN, and had an approximate molecular weight of 48,000 as estimated by gel filtration. Two other products, 13-hydroxy-cis-9,trans-11,cis-15-octadecatrienoic acid and 12,13-trans-epoxy-9-oxotrans-10,cis-15-octadecadienoic acid, were also observed. Because these compounds are also products of nonenzymic, Fe(ll)-catalyzed hydroperoxide decomposition reactions, their presence suggested that the observed lyase activity may occur via a homolytic decomposition mechanism.

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Infrared Absorption Spectra of Some Epoxy Compounds

Cited by 118 publications

References 13 publications

Spectroscopic Investigation of the Cashew Nut Kernel (Anacardium occidentale)

Spectroscopic Investigation of the Cashew Nut Kernel (Anacardium occidentale)

Pressure-sensitive adhesives based on soybean fatty acids

Metabolism of Fatty Acid Hydroperoxides by Chlorella pyrenoidosa

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