PROCESSES FOR PREPARING ESTOLIDE BASE OILS AND BIOBASED COMPOUNDS THAT INCLUDE ETHYLENEOLYSIS
Provided herein are compounds prepared from processes that include ethyleneolysis. Exemplary processes include the preparation of terminally-unsaturated fatty acid reactant by ethyleneolysis catalyzed by a cyclic alkyl amino carbene ruthenium complex. The subsequent oligomerization of terminally-unsaturated fatty acid reatants provides estolide compounds, as exemplified by the process set forth below:
1 - 201 . (canceled)
202 . A process comprising
providing a terminally-unsaturated fatty acid reactant derived from a process that includes contacting one or more unsaturated fatty acid substrates having at least one internal site of unsaturation with a cyclic alkyl amino carbene ruthenium complex in the presence of ethylene; and
reacting the terminally-unsaturated fatty acid reactant with a second fatty acid reactant to provide at least one compound.
203 . (canceled)
204 . (canceled)
205 . (canceled)
206 . The process according to claim 202 , wherein the one or more unsaturated fatty acid substrate comprises a triglyceride having at least one oleic acid residue.
207 . (canceled)
208 . (canceled)
209 . The process according to claim 202 , wherein the terminally-unsaturated fatty acid reactant comprises 9-decenoic acid.
210 . The process according to claim 202 , wherein the second fatty acid reactant comprises at least one of a saturated fatty acid or an unsaturated fatty acid.
211 . (canceled)
212 . (canceled)
213 . The process according to claim 202 , further comprising esterifying the at least one compound with an alcohol to provide an esterified compound.
214 . The process according to claim 213 , further comprising hydrogenating the esterified compound to provide a hydrogenated compound.
215 . (canceled)
216 . (canceled)
217 . (canceled)
218 . (canceled)
219 . (canceled)
220 . (canceled)
221 . (canceled)
222 . The process according to claim 202 , wherein the cyclic alkyl amino carbene ruthenium complex comprises at least one compound selected from Formula B:
wherein
X 1 and X 2 are independently selected from alkoxy and halogen;
R 6 , R 7 and R 8 are independently selected from branched or unbranched alkyl;
R 5 is selected from branched or unbranched alkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted arylalkyl, and optionally substituted heteroarylalkyl, or
R 5 and R 6 are taken together with the carbon to which they are bound to form a 5-, 6-, or 10-membered cycloalkyl or heterocyclyl ring, each of which is optionally substituted;
R 12 is a branched or unbranched alkyl;
R 9 and R 11 are independently selected from hydrogen and branched or unbranched alkyl; and
R 10 is branched or unbranched alkyl.
223 . (canceled)
224 . The process according to claim 222 , wherein when R 11 is hydrogen, R 9 comprises a smaller number of atoms than R 10 .
225 . The process according to claim 222 , wherein when R 11 is hydrogen, R 9 is selected from unbranched alkyl and R 10 is selected from branched alkyl.
226 . The process according to claim 222 , wherein X 1 and X 2 are halogen.
227 . The process according to claim 226 , wherein X 1 and X 2 are chlorine.
228 . The process according to claim 222 , wherein R 12 is a branched C 3 to C 10 alkyl.
229 . The process according to claim 228 , wherein R 12 is isopropyl.
230 . (canceled)
231 . The process according to claim 222 , wherein R 6 , R 7 and R 8 are independently selected from methyl, ethyl, and propyl.
232 . (canceled)
233 . (canceled)
234 . The process according claim 222 , wherein R 11 is hydrogen.
235 . (canceled)
236 . The process according to claim 222 , wherein R 9 is selected from unbranched C 1 to C 10 alkyl.
237 . The process according to claim 236 wherein R 9 is selected from methyl, ethyl, and propyl.
238 . The process according to claim 222 wherein R 10 is selected from branched C 3 to C 10 alkyl.
239 . The process according to claim 238 , wherein R 10 is selected from isopropyl, isobutyl, and tert-butyl.
240 . The process according to claim 222 , wherein R 5 is aryl.
241 . The process according to claim 240 , wherein R 5 is phenyl.