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

Abstract

Transition-metal trifluoromethane-sulphonatesrecyclable catalysts for the synthesis of branched fatty derivatives by Diels-Alder reactions at unsaturated fatty esters Diels-Alder reactions of conjugated linoleic acid ethyl ester (1) with different quinones and with a variety of α/β-unsaturated 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.

Maleinisation of monounsaturated fatty acids by Rh‐catalysis

“…, CH --CH); 3.69 (s, 6H, 2ÂCHCOOCH 3 ); 3.66 (s, 3H, CH 2 COOCH 3 ); 3.08 (d, 2H, 2 J HH ¼ 6.5 Hz, 2ÂCHCOOCH 3 ) 2.41-2.43 (m, 2H, 2xCHCH 2 ); 2.29 (t, 2H, 3 J HH ¼ 7.4 Hz, CH 2 COOCH 3 ); 1.57-1.63 (qui, 2H, 3 J HH ¼ 7.4 Hz, CH 2 CH 2 COO); 1.26-1.52 (m, 20H, 10ÂCH 2 ); 0.88 (t, 3H, 3 J HH ¼ 6.9 Hz, CH 2 CH 3 ); 13 (17); 378 (6); 346 (94); 328 (22); 318 (22); 296 (4); 287 (29); 279 (55); 269 (12); 247 (100); 233 (17); 215 (13); 203 (14); 189 (42); 175 (10); 145 (61); 119 (11); 113 (37); 105 (34); 91 (31); 79 (14); 69 (15); 55 (28); 43 (21); syn-Trimethyl-3-octyl-(E)-undec-4-ene-1,2,11-tricarboxylate (5a) and syn-Trimethyl-(E)-3-(non-1-ene-1-yl)decane-1,2,10-tricarboxylate(6a) [1,2] : 1 (10); 348 (93); 335 (25); 316 (25); 303 (15); 294 (14); 265 (11); 263 (11); 247 (12); 219 (12); 205 (15); 189 (9); 175 (7); 161 (7); 149 (13); 146 (100); 135 (11); 121 (14); 114 (37); 97 (20); 95 (23); 81 (30); 67 (30); 55 (41); 44 (30); anti-Trimethyl- We have previously reported on the maleinisation of linoleic acid [26], where we found that Rh(OAc) 2 shows a higher activity and leads to higher yields compared to RhCl 3 (H 2 O) 3 . The same tendency was found for 2, which is consistent with the results of Behr and Handwerk [28].…”

Silylation of triacylglycerol: an easy route to new biosiloxanes

“…fatty acid derivatives (Behr et al, 2000(Behr et al, , 2003. The products possess interesting chemical and physical properties making them attractive for many industrial applications (Behr, 1990).…”

Hydroaminomethylation of fatty acids with primary and secondary amines — A new route to interesting surfactant substrates

“…However, only little work has been done on the synthesis of such compounds [1][2][3][4][5]. Recently we have published our results on the ene-reaction and the Diels-Alder reaction of unsaturated fatty esters [6][7][8].…”