# US 2013/0158277 A1 · Processes for preparing estolide base oils and oligomeric compounds that include cross metathesis > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2013/0158277 A1 - Document ID: US20130158277A1 - Status: Published application - Kind: A1 - Application number: 13/707,480 - Filed: 2012-12-06 - Published: 2013-06-20 - Earliest claimed: 2011-12-19 - Assignees: Biosynthetic Technologies, LLC - Inventors: Travis Thompson; Kelly Parson; Jakob Bredsguard; Jeremy Forest - Web page: https://patentgrep.com/patent/US20130158277A1 ## CPC - C07C 69/604: Polycarboxylic acid esters, the acid moiety containing more than two carboxyl groups - C07C 67/347: by addition to unsaturated carbon-to-carbon bonds - C07C 69/602: Dicarboxylic acid esters having at least two carbon-to-carbon double bonds - C07C 69/67: of saturated acids - C07C 69/675: of saturated hydroxy-carboxylic acids - C10M 105/04: aliphatic - C10M 105/36: of polycarboxylic acids - C10M 105/42: Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids - C10M 107/32: Condensation polymers of aldehydes or ketones; Polyesters; Polyethers - C10M 177/00: Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes - C08G 63/06: derived from hydroxycarboxylic acids - C10M 2207/281: of (cyclo)aliphatic monocarboxylic acids - C10M 2207/282: of (cyclo)aliphatic oolycarboxylic acids - C10M 2207/2825: used as base material - C10M 2207/301: used as base material - C10M 2209/1023: used as base material - C10N 2020/013: {Iodine value} - C10N 2030/02: Pour-point; Viscosity index - C10N 2030/10: Inhibition of oxidation, e.g. anti-oxidants - C10N 2030/64: {Environmental friendly compositions} - C10N 2070/00: Specific manufacturing methods for lubricant compositions - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS ## Abstract Provided herein are estolide base oils and oligomeric compounds prepared from processes that include cross metathesis. Exemplary processes include the preparation of terminally-unsaturated fatty acids by cross metathesis, and the subsequent oligomerization of terminally-unsaturated fatty acids to provide estolide compounds, such as the process set forth below: ## Claims ### Claim at position 1 1-41. (canceled) ### Claim 42 A process of producing an estolide base oil comprising: providing at least one triglyceride having at least one fatty acid residue with at least one internal site of unsaturation; providing at least one alpha olefin having at least three carbon atoms; contacting the at least one triglyceride with the at least one alpha olefin in the presence of a metathesis catalyst to provide an olefin product and a metathesized fatty acid product; hydrolyzing the metathesized fatty acid product into at least one first fatty acid product, wherein the at least one first fatty acid product comprises at least one fatty acid having an internal site of unsaturation and at least one fatty acid having a terminal site of unsaturation; providing an oligomerization catalyst; and oligomerizing at least a portion of the at least one first fatty acid product in the presence of the oligomerization catalyst to produce an estolide base oil, wherein said oligomerizing comprises forming a covalent bond between an oxygen of a carboxylic group of a first fatty acid and a carbon of a site of unsaturation of a second fatty acid. ### Claim 43 (canceled) ### Claim 44 (canceled) ### Claim 45 (depends on 42) The process according to claim 42, wherein the oligomerization catalyst is selected from a Bronsted acid and a Lewis acid. ### Claim at position 6 46-51. (canceled) ### Claim 52 (depends on 42) The process according to claim 42, wherein the oligomerization catalyst is a Bronsted acid. ### Claim at position 8 53-63. (canceled) ### Claim 64 (depends on 42) The process according to claim 42, wherein the at least one alpha olefin is selected from one or more of propene, 1-butene, 1-pentene, 1-hexene, 1-heptene, or 1-octene. ### Claim 65 (depends on 42) The process according to claim 42, wherein the metathesis catalyst is an osmium or ruthenium alkylidene metathesis catalyst. ### Claim 66 (depends on 65) The process according to claim 65, wherein the metathesis catalyst is a first generation or second generation Grubbs'-type metathesis catalyst. ### Claim 67 (depends on 42) The process according to claim 42, wherein the at least one triglyceride comprises at least one fatty acid residue selected from oleic acid, linoleic acid, and linolenic acid. ### Claim 68 (depends on 42) The process according to claim 42, wherein the olefin product comprises at least one terminal olefin and at least one internal olefin. ### Claim 69 (canceled) ### Claim 70 (depends on 68) The process according to claim 68, wherein the at least one internal olefin is 3-dodecene. ### Claim 71 (canceled) ### Claim 72 (depends on 68) The process according to claim 68, wherein the at least one terminal olefin is 1-decene. ### Claim 73 (canceled) ### Claim 74 (canceled) ### Claim 75 (depends on 42) The process according to claim 42, wherein the metathesized fatty acid product comprises at least one fatty acid residue having a terminal site of unsaturation. ### Claim at position 21 76-78. (canceled) ### Claim 79 (depends on 75) The process according to claim 75, wherein the metathesized fatty acid product is a triglyceride comprising at least one 9-decenoic acid residue. ### Claim 80 (depends on 42) The process according to claim 42, wherein the metathesized fatty acid product comprises at least one fatty acid residue having an internal site of unsaturation. ### Claim at position 24 81-83. (canceled) ### Claim 84 (depends on 80) The process according to claim 80, wherein a metathesized fatty acid product is a triglyceride comprising at least one 9-dodecenoic acid residue. ### Claim at position 26 85-94. (canceled) ### Claim 95 (depends on 42) The process according to claim 42, further comprising esterifying the resulting estolide base oil with at least one alcohol to provide an esterified estolide base oil. ### Claim at position 28 96-164. (canceled) ### Claim 165 At least one compound according to Formula III: wherein n is an integer equal to or greater than 0; R1 is an optionally substituted, branched or unbranched alkyl that is saturated or unsaturated; R2 is selected from hydrogen and optionally substituted alkyl that is saturated or unsaturated, and branched or unbranched; and R3 and R4, independently for each occurrence, are selected from wherein R3 and R4 are independently optionally substituted and z is, independently for each occurrence, an integer selected from 0 to 40. ### Claim at position 30 166-197. (canceled) ### Claim 198 (depends on 42) The process according to claim 42, wherein the at least one fatty acid having an internal site of unsaturation is 9-dodecenoic acid. ### Claim 199 (depends on 42) The process according to claim 42, wherein the at least one fatty acid product having a terminal site of unsaturation is 9-decenoic acid. ### Claim 200 (canceled) ### Claim 201 (depends on 42) The process according to claim 42.