# US 9,040,752 B2 · Process for producing ketones from fatty acids > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,040,752 B2 - Document ID: US9040752B2 - Status: Granted - Kind: B2 - Application number: 13/486,097 - Filed: 2012-06-01 - Published: 2013-12-05 - Granted: 2015-05-26 - Earliest claimed: 2012-06-01 - Assignees: Chevron U.S.A. Inc. - Applicants: Sven Ivar Hommeltoft; Ann Jia-Bao Liang - Inventors: Sven Ivar Hommeltoft; Ann Jia-Bao Liang - Web page: https://patentgrep.com/patent/US9040752B2 ## CPC - C10M 105/20: Aldehydes; Ketones - C07C 45/41: by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof - C07C 45/48: involving decarboxylation - C10M 2207/085: used as base material - C10N 2080/00: Special pretreatment of the material to be lubricated, e.g. phosphatising or chromatising of a metal - Y02P 20/582: Recycling of unreacted starting or intermediate materials - 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) - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS - Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS ## Abstract The invention relates to a process for producing ketones or hydrocarbon base oil from fatty acids preferably derived from a biological origin or other renewable source. The process is directed at making an aliphatic ketone or a mixture of aliphatic ketones having 14 to 52 carbon atoms, comprising a ketonization reaction of a fatty acid in a vapor phase with a decarboxylation-coupling catalyst to provide ketones, which can be deoxygenated to give saturated hydrocarbons, unsaturated hydrocarbons, and mixtures thereof. Base oils and transportation fuels may be produced from the process herein. ## Claims ### Claim 1 A process for making an aliphatic ketone or a mixture of aliphatic ketones having about 14 to 52 carbon atoms, comprising: reaction of a fatty acid in a vapor phase with a decarboxylation-coupling catalyst in a decarboxylation-coupling zone, wherein a decarboxylation-coupling zone temperature is between about 20° C. to 100° C. above the condensation point of the fatty acid at the partial pressure of the fatty acid in the decarboxylation-coupling zone. ### Claim 2 (depends on 1) The process of claim 1, wherein the decarboxylation-coupling zone temperature is at least about 20° C., 25° C., 30° C., 35° C., 40° C., 45° C., 50° C., 55° C., 60° C. or 65° C. above the condensation point at the partial pressure of the fatty acid in the decarboxylation-coupling zone. ### Claim 3 (depends on 1) The process of claim 1, wherein the partial pressure of the fatty acid is between about 75 psia to 1 psia. ### Claim 4 A process for making an aliphatic ketone or a mixture of aliphatic ketones having about 14 to 52 carbon atoms, comprising: reaction of a fatty acid in a vapor phase with a decarboxylation-coupling catalyst in a decarboxylation-coupling zone, wherein a partial pressure of the fatty acid is between 1% and 90% of the partial pressure at the condensation point at a given decarboxylation-coupling zone temperature. ### Claim 5 (depends on 4) The process of claim 4, wherein the decarboxylation-coupling zone temperature is between about 100° C. to 500° C. ### Claim 6 (depends on 4) The process of claim 4, wherein the partial pressure of the fatty acid is no more than 90%, 75%, 50%, 25%, 10%, 5% or 2% of the partial pressure at the condensation point at the given decarboxylation-coupling zone temperature. ### Claim 7 (depends on 1, 4) The process of claim 1 or 4, wherein the partial pressure of the fatty acid is lowered relative to the pressure in the decarboxylation-coupling zone by the addition of an inert diluent selected from the group consisting of nitrogen, hydrogen, carbon monoxide, water, carbon dioxide, C1-C18 aliphatic hydrocarbon, and mixtures thereof. ### Claim 8 (depends on 1, 4) The process of claim 1 or 4, wherein the decarboxylation-coupling catalyst is selected from the group consisting of alumina, supported metal carbonates, supported metal hydroxides, supported metal oxides, and combinations thereof. ### Claim 9 (depends on 1, 4) The process of claim 1 or 4, wherein the fatty acid is selected from the group consisting of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, palmitolic acid, oleic acid, palm kernel oil acids, palm oil acids, coconut oil acids, soy bean oil acids, rape seed oil fatty acids, poultry fat derived fatty acids, beef tallow derived fatty acids, and combinations thereof. ### Claim 10 (depends on 1, 4) The process of claim 1 or 4, further comprising a fatty acid conversion to the ketone of between about 70% to 100%. ### Claim 11 (depends on 1, 4) The process of claim 1 or 4, further comprising a fatty acid conversion selectivity to the ketone of between about 30% to 100%. ### Claim 12 (depends on 1, 4) The process of claim 1 or 4, further comprising a step of distilling, hydrocracking, hydroisomerization dewaxing, hydrofinishing, and combinations thereof. ### Claim 13 (depends on 1, 4) The process of claim 1 or 4, further comprising a step of blending the aliphatic ketone or mixture of aliphatic ketones with a base oil selected from the group consisting of Group I oils, Group II oils, Group III oils, and combinations thereof to provide a lubricant composition.