Processes for preparing estolide base oils and biobased compounds that include ethyleneolysis

Patent metadata

Field	Value
Publication number	US-2016244397-A1
Application number	US-201615047112-A
Country	US
Kind code	A1
Filing date	Feb 18, 2016
Priority date	Feb 20, 2015
Publication date	Aug 25, 2016
Grant date	—

Abstract

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:

First claim

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.

Assignees

• Biosynthetic Technologies Llc

Inventors

• Forest Jeremy

Classifications

• C07C67/08 Primary

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• B01J31/2265 Primary

  Carbenes or carbynes, i.e.(image) · CPC title

• B01J31/2291

  Olefins · CPC title

• C07C67/465 Primary

  by oligomerisation · CPC title

• B01J2231/52

  Isomerisation reactions · CPC title