Modified triglyceride oil through reactions with phenyltriazolinedione

JAOCS, Journal of the American Oil Chemists' Society

Volumn 91, Issue 1, 2014, Pages 125-131

  Biswas, Atanu ^a   Cheng, H N ^b   Kim, Sanghoon ^a   Liu, Zengshe ^a  

^a NATIONAL CENTER FOR AGRICULTURAL UTILIZATION RESEARCH   (United States)

^b SOUTHERN REGIONAL RESEARCH CENTER   (United States)

Author keywords

2 4 triazoline 3; 4 Phenyl 1; 5 dione (PTAD); Diels Alder reaction; Ene reaction; Fatty acid methyl ester; Soybean oil; Triglyceride

Indexed keywords

2-4-TRIAZOLINE-3; 4-PHENYL-1; 5-DIONE (PTAD); DIELS-ALDER REACTION; ENE REACTION; FATTY ACID METHYL ESTER; TRIGLYCERIDE;

CURING; ESTERS; MIXTURES; REACTION PRODUCTS; SOYBEAN OIL;

ESTERIFICATION;

ALNUS; GLYCINE MAX;

EID: 84892560088     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-013-2326-9     Document Type: Article

References (20)

1. Xia Y, Larock RC (2010) Vegetable oil-based polymeric materials: synthesis, properties, and applications. Green Chem 12:1893-1909
2. Meier ARM, Metzger JO, Schubert US (2007) Plant oil renewable resources as green alternatives in polymer science. Chem Soc Rev 36:1788-1902
3. Guner SF, Yagci Y, Erciyes AT (2006) Polymers from triglyceride oils. Prog Polym Sci 31:633-670
4. Biswas A, Sharma BK, Willett JL, Vermillion K, Erhan SZ, Cheng HN (2007) Novel modified soybean oil containing hydrazino-ester: synthesis and characterization. Green Chem 9:85-89
5. Biswas A, Adhvaryu A, Gordon SH, Erhan SZ, Willett JL (2005) Synthesis of diethylamine functionalized soybean oils. J Agric Food Chem 53(24):9485-9490
6. Biswas A, Sharma BK, Doll KM, Erhanm SZ, Cheng HN (2009) Synthesis of an amine-oleate derivative using an ionic catalyst. J Agric Food Chem 57:8136-8141
7. Biswas A, Sharma BK, Willett JL, Erhan SZ, Cheng HN (2008) Azide derivatives of soybean oil and fatty esters. J Agric Food Chem 56:5611-5616
8. Biswas A, Sharma BK, Klasson KT, Cheng HN (2011) New biobased materials from soybean oil: amination and click reactions. ACS Polym Prepr 52(1):78-79
9. Biswas A, Sharma BK, Willett JL, Erhan SZ, Cheng HN (2008) Soybean oil as a renewable feedstock for nitrogen-containing derivatives. Energy Environ Sci 1:639-644
10. Ohashi S, Leong KW, Matyjaszewski K, Butler GB (1980) Ene reaction of triazolinediones with alkenes. 1. Structures and properties of products. J Org Chem 45:3467-3471
11. Desimoni G, Faita G, Righetti PP, Sfulcini A, Tsyganov D (1994) Solvent effect in pericyclic reactions 9. The ene reaction. Tetrahedron 50(6):1821-1832
12. Hunter NB, Krawchuk BP, Shiloff JD (1982) Ene-type adducts from the reaction of 4-phenyl-1,2,4-triazoline-3,5-dione with balkyl s-cis enone. Can J Chem 60:835-839
13. Smonou I, Khan S, Foote CS, Elemes Y, Mavridis IM, Pantidou A, Orfanopoulos M (1995) Reactions of phenyltriazolinedione with alkenes. Stereochemistry of methanol adducts to aziridinium imide intermediates. J Amer Chem Soc 117:7081-7087
14. Celius TC (2010) Fast hetero-Diels-Alder reactions using 4-phenyl-1,2-4-triazoline-3,5-dione (PTAD) as the dienophile. J Chem Ed 87(11):1236-1237
15. Alberti MN, Orfanopoulos M (2009) Concerning the reactivity of PTAD with isomeric dienes: the mechanism of the Diels-Alder cycloaddition. Org Lett 11(7):1659-1662
16. McLellan JF, Mortier RM, Orszulik ST, Paton RM (2000) Tandem ene addition/Diels-Alder cycloaddition reactions of methyl linoleate with 4-phenyl-1,2,4-triazoline-3,5-dione and diethyl azodicarboxylate. J Chem Res (S) 2000:339-341
17. McLellan JF, Mortier RM, Orszulik ST, Paton RM (1993) Ene reactions of jojoba oil with 4-phenyl-1,2,4-triazoline-3,5-dione and diethyl azodicarboxylate. Chem Ind (Lond) 1993:94-95
18. Guillen MD, Ruiz A (2005) Monitoring the oxidation of unsaturated oils and formation of oxygenated aldehydes by proton NMR. Eur J Lipid Sci Technol 107:36-47
19. Guillen MD, Ruiz A (2006) Study by means of 1H NMR of the oxidation process undergone by edible oils of different natures submitted to microwave action. Food Chem 96:665-674
20. Korobitsyna IK, Khlikova AV, Rodina LL, Shusherina NP (1983) 4-Phenyl-1,2,4-triazoline-3,5-dione in organic synthesis (review). Khim Getero Soedin 2:147-169