Epoxidation of natural triglycerides with ethylmethyldioxirane

被引:23
作者
Sonnet, PE
Foglia, TA
机构
[1] USDA, AAS, ERRC, Philadelphia
[2] USDA, ARS, ERRC, Philadelphia, PA 19118
关键词
biphasic epoxidation; epoxides; oils and fats; oxirane; phase-transfer catalyzed;
D O I
10.1007/BF02523919
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Phase-transfer catalyzed biphasic epoxidation of a series of fats and oils with ethylmethyldioxirane in 2-butanone was conducted. The series of glycerides studied varied from monounsaturated (olive) to highly polyunsaturated (flaxseed) oils. Best conversions for polyunsaturate-containing oils were obtained with a molar ratio of 2.5:1 (oxidant/oil) with two-step addition of oxidant. Conversion to epoxides was monitored by gas-liquid chromatography, and oxirane content was determined by titration. The effect of phase-transfer catalyst or solvent used for the epoxidation reaction also was investigated.
引用
收藏
页码:461 / 464
页数:4
相关论文
共 10 条
[1]  
*AM OIL CHEM SOC, 1983, OFF METH REC PRACT A
[2]   EPOXIDATION OF ALKENES BY DIOXIRANE INTERMEDIATES GENERATED IN THE REACTION OF POTASSIUM CAROATE WITH KETONES [J].
CURCI, R ;
FIORENTINO, M ;
TROISI, L ;
EDWARDS, JO ;
PATER, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) :4758-4760
[3]  
FORMO MW, 1982, BAILEYS IND OIL FAT, P343
[4]   ANALYSIS OF EPOXIDIZED SOYBEAN OIL BY GAS-CHROMATOGRAPHY [J].
HAN, LMT ;
SZAJER, G .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1994, 71 (06) :669-670
[5]   EPOXIDATION OF METHYL LINOLEATE .2. 2 ISOMERS OF METHYL 9,10 - 12,13-DIEPOXYSTEARATE [J].
MAERKER, G ;
HAEBERER, ET ;
HERB, SF .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1966, 43 (08) :505-&
[6]   DIOXIRANES - SYNTHESIS AND REACTIONS OF METHYLDIOXIRANES [J].
MURRAY, RW ;
JEYARAMAN, R .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16) :2847-2853
[7]   ION CHROMATOGRAPHIC DETERMINATION OF PHOSPHORUS AND TUNGSTEN IN EPOXIDIZED SOYBEAN OIL [J].
QUAGLINO, M ;
BOTTAZZINI, N ;
QUERCI, C ;
RICCI, M ;
CAVALLI, S .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1992, 69 (12) :1248-1250
[8]   CHEMISTRY OF DIOXIRANES .21. THERMAL-REACTIONS OF DIOXIRANES [J].
SINGH, M ;
MURRAY, RW .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4263-4270
[9]   REACTIONS OF DIOXIRANES WITH SELECTED OLEOCHEMICALS [J].
SONNET, PE ;
LANKIN, ME ;
MCNEILL, GP .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1995, 72 (02) :199-204
[10]   QUATERNARY AMMONIUM TETRAKIS(DIPEROXOTUNGSTO)PHOSPHATES(3-) AS A NEW CLASS OF CATALYSTS FOR EFFICIENT ALKENE EPOXIDATION WITH HYDROGEN-PEROXIDE [J].
VENTURELLO, C ;
DALOISIO, R .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (07) :1553-1557