Diels‐alder adducts from safflower fatty acids: III. Acrylic and related acid dienophiles

Sastry, G. S. R.; Murthy, B. G. K.; Aggarwal, J. S.

doi:10.1007/bf02633794

Cited by 9 publications

(3 citation statements)

References 7 publications

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“…Safflower oil was isomerized to arrange the C-C double bonds into conjugated configuration and used in DA reactions, in earlier works dating back to 1971 and 1972 [27][28][29]. Esters of the modified oil were successfully reacted with maleic anhydride, styrene, and acrylic acid as dienophiles [27][28][29]. Another interesting raw material is tung oil, which naturally contains conjugated trienes.…”

Section: Introductionmentioning

confidence: 99%

Thermally Reversible Polymeric Networks from Vegetable Oils

et al. 2020

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Low cross-link density thermally reversible networks were successfully synthesized from jatropha and sunflower oils. The oils were epoxidized and subsequently reacted with furfurylamine to attach furan groups onto the triglycerides, preferably at the epoxide sites rather than at the ester ones. Under the same reaction conditions, the modified jatropha oil retained the triglyceride structure more efficiently than its sunflower-based counterpart, i.e., the ester aminolysis reaction was less relevant for the jatropha oil. These furan-modified oils were then reacted with mixtures of aliphatic and aromatic bismaleimides, viz. 1,12-bismaleimido dodecane and 1,1′-(methylenedi-4,1-phenylene)bismaleimide, resulting in a series of polymers with Tg ranging between 3.6 and 19.8 °C. Changes in the chemical structure and mechanical properties during recurrent thermal cycles suggested that the Diels–Alder and retro-Diels–Alder reactions occurred. However, the reversibility was reduced over the thermal cycles due to several possible causes. There are indications that the maleimide groups were homopolymerized and the Diels–Alder adducts were aromatized, leading to irreversibly cross-linked polymers. Two of the polymers were successfully applied as adhesives without modifications. This result demonstrates one of the potential applications of these polymers.

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Section: Introductionmentioning

confidence: 99%

Thermally Reversible Polymeric Networks from Vegetable Oils

et al. 2020

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“…Moreover, we have already reported on the synthesis of Diels-Alder-like cycloadducts directly from mono-unsaturated [28] and non-conjugated fatty acids [29], as well as mixtures thereof by Rh-catalysis. Herein, we have focused so far on the catalytic addition of maleic anhydride (3). In this article, we are going to report on the Rh-catalysed addition of maleic acid-(4), fumaric acid-(5) and acetylene dicarboxylic acid dimethyl ester (9).…”

Section: Introductionmentioning

confidence: 99%

“…The application of CLAs as dienes in Diels–Alder reaction with maleic anhydride ( 3 ) as dienophile was mentioned first by Böeseken and Hoevers in 1930 . Teeter et al and Sastry et al used further dienophiles, like acrylic acid, acrolein or crotonic acid, but for sufficient yields high temperatures had to be applied, which caused several side reactions. Von Mikusch has figured out that the reason for the high‐reaction temperatures is the E , Z ‐configuration of the used CLAs.…”

Section: Introductionmentioning

confidence: 99%

Rhodium‐catalysed cyclisation by addition of unsaturated 1,4‐dicarbonyl compounds to oleic acid methyl ester

Eschig

Schirp

2015

Euro J Lipid Sci & Tech

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The Rh-catalysis allows the one-step synthesis of Diels–Alder-like cycloadducts from mono-unsaturated fatty acid and 1,4-dicarbonyl components. In this article we report on the addition of maleic acid-, fumaric acid- and acetylene dicarboxylic acid dimethyl ester to oleic acid methyl ester. In previous studies, Rh(OAc)2 showed the highest selectivity of the investigated catalysts towards the 3,6-disubstituted-1,2,3,6-tetrahydro-phthalic acid derivatives (THPA) for the addition of maleic anhydride to oleic acid. Thus, it was also used in this study. The relative configurations of the final products were identified by comparison with the Diels–Alder products, resulting from conjugated linoleic acid methylester (CLAMe) and the mentioned 1,4-dicarbonyl compounds

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Transition-metal trifluoromethane-sulphonates-recyclable catalysts for the synthesis of branched fatty derivatives byDiels-Alder reactions at unsaturated fatty esters

Behr¹,

Fiene²,

Naendrup³

et al. 2000

Eur. J. Lipid Sci. Technol.

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Diels‐Alder reactions of conjugated linoleic acid ethyl ester (1) with different quinones and with a variety of α/βunsaturated aldehydes and ketones are described in this paper. Using Sc(OTf)3 or Cu(OTf)2 as catalysts the reactions can be carried out at 25—40 °C with good yields. For the first time in oleochemistry it is possible to prepare Diels‐Alder cycloadditions with catalyst concentrations of 10 mol‐% instead of stoichiometric amounts of Lewis acids. Furthermore, the reaction time was partly shortened drastically. The catalyst Sc(OTf)3 can be removed by a simple extraction of the organic layer with water. After evaporation of the aqueous phase to dryness the catalyst can be reused without loss of yield.

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Diels‐alder adducts from safflower fatty acids: III. Acrylic and related acid dienophiles

Cited by 9 publications

References 7 publications

Thermally Reversible Polymeric Networks from Vegetable Oils

Thermally Reversible Polymeric Networks from Vegetable Oils

Rhodium‐catalysed cyclisation by addition of unsaturated 1,4‐dicarbonyl compounds to oleic acid methyl ester

Transition-metal trifluoromethane-sulphonates-recyclable catalysts for the synthesis of branched fatty derivatives byDiels-Alder reactions at unsaturated fatty esters

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