Reduction of high oleic sunflower oil to glyceryl trioleyl ether

被引:11
作者
Biermann, Ursula [1 ]
Metzger, Juergen O. [1 ,2 ]
机构
[1] Carl von Ossietzky Univ Oldenburg, Inst Chem, D-26111 Oldenburg, Germany
[2] Abiosus eV, Oldenburg, Germany
关键词
GaBr3; Glyceryl triether; High oleic sunflower oil; InBr3; Renewable; Triglycerides; 1; 3; 3-tetramethyldisiloxane; ALIPHATIC METHANESULFONATES; CARBOXYLIC-ACIDS; ESTERS; CONVERSION; TRIGLYCERIDES; ALKYLATION; LACTONES;
D O I
10.1002/ejlt.201300320
中图分类号
TS2 [食品工业];
学科分类号
0832 ;
摘要
High oleic sunflower oil was converted into the respective triether using InBr3 or GaBr3 as catalysts and triethylsilane or 1,1,3,3-tetramethyldisiloxane (TMDS) as reducing agent in solvent-free reactions. GaBr3/TMDS was found to be the most efficient reduction system enabling to carry out the reduction at room or moderately elevated temperature using stoichiometric amounts of TMDS and low amounts of the catalyst (0.005-0.01eq. Ga/ester functionality). The conversion of the starting material was 100% yielding 80% of glyceryl trioleyl ether 2.
引用
收藏
页码:74 / 79
页数:6
相关论文
共 28 条
[1]   REACTIONS OF ALIPHATIC METHANESULFONATES .2. SYNTHESES OF LONG-CHAIN DI- AND TRIALKYL GLYCERYL ETHERS [J].
BAUMANN, WJ ;
MANGOLD, HK .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (02) :498-+
[2]   REACTIONS OF ALIPHATIC METHANESULFONATES .I. SYNTHESES OF LONG-CHAIN GLYCERYL-(1) ETHERS [J].
BAUMANN, WJ ;
MANGOLD, HK .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (10) :3055-&
[3]   NEW CONVERSION OF ESTERS TO ETHERS AND ITS APPLICATION TO THE PREPARATION OF FURANO-18-CROWN-6 [J].
BAXTER, SL ;
BRADSHAW, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (04) :831-832
[4]   Synthesis of Ethers by GaBr3-Catalyzed Reduction of Carboxylic Acid Esters and Lactones by Siloxanes [J].
Biermann, Ursula ;
Metzger, Juergen O. .
CHEMSUSCHEM, 2014, 7 (02) :644-649
[5]   Synthesis of ethers from esters via Fe-catalyzed hydrosilylation [J].
Das, Shoubhik ;
Li, Yuehui ;
Junge, Kathrin ;
Beller, Matthias .
CHEMICAL COMMUNICATIONS, 2012, 48 (87) :10742-10744
[6]   1,1,3,3-Tetramethyldisiloxane [J].
Deng, Jia .
SYNLETT, 2011, (14) :2102-2103
[7]   SYNTHESIS OF LONG-CHAIN ALKYL GLYCERYL ETHERS FROM TRIGLYCERIDES USING BORON-TRIFLUORIDE ETHERATE AND LITHIUM ALUMINUM-HYDRIDE [J].
GO, HC ;
BRANEN, AL .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1975, 52 (10) :427-429
[9]   Convenient two-step conversion of lactones into cyclic ethers [J].
Hansen, MC ;
Verdaguer, X ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) :2360-2361
[10]   THE SYNTHESIS OF SOME ETHERS AND MIXED ETHER ESTERS OF GLYCEROL [J].
JOLL, CA ;
MORTIMER, BC ;
REDGRAVE, TG ;
STICK, RV .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (08) :1445-1448