# US 8,541,626 B2 · Method for synthesis of ketones from plant oils > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,541,626 B2 - Document ID: US8541626B2 - Status: Granted - Kind: B2 - Application number: 13/356,731 - Filed: 2012-01-24 - Published: 2013-07-25 - Granted: 2013-09-24 - Earliest claimed: 2012-01-24 - Assignees: The United States of America as represented by the Secretary of Agriculture - Applicants: Michael A. Jackson; Steven C. Cermak - Inventors: Michael A. Jackson; Steven C. Cermak - Web page: https://patentgrep.com/patent/US8541626B2 ## CPC - C07C 45/48: involving decarboxylation - B01J 23/83: with rare earths or actinides - B01J 35/615: {100-500 m2/g} - B01J 35/633: {less than 0.5 ml/g} - B01J 35/647: {2-50 nm} - B01J 37/03: Precipitation; Co-precipitation - C01F 17/34: Aluminates, e.g. YAlO3 or Y3-xGdxAl5O12 - C01G 49/009: {Compounds containing iron, with or without oxygen or hydrogen, and containing two or more other elements} - C07C 29/095: {of esters of organic acids} - C01P 2004/62: Submicrometer sized, i.e. from 0.1-1 micrometer - C01P 2004/64: Nanometer sized, i.e. from 1-100 nanometer - C01P 2006/12: Surface area - C01P 2006/14: Pore volume - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS - C01F: COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS (metal hydrides {monoborane, diborane or addition complexes thereof} C01B6/00; salts of oxyacids of halogens C01B11/00; peroxides, salts of peroxyacids C01B15/00; sulfides or polysulfides of magnesium, calcium, strontium, or barium C01B17/42; thiosulfates, dithionites, polythionates C01B17/64; compounds containing selenium or tellurium C01B19/00; binary compounds of nitrogen with metals C01B21/06; azides C01B21/08; {compounds other than ammonia or cyanogen containing nitrogen and non-metals and optionally metals C01B21/082; amides or imides of silicon C01B21/087}; metal {imides or} amides C01B21/092, {C01B21/0923}; nitrites C01B21/50; {compounds of noble gases C01B23/0005}; phosphides C01B25/08; salts of oxyacids of phosphorus C01B25/16; carbides C01B32/90; compounds containing silicon C01B33/00; compounds containing boron C01B35/00; compounds having molecular sieve properties but not having base-exchange properties C01B37/00; compounds having molecular sieve and base-exchange properties, e.g. crystalline zeolites, C01B39/00; cyanides C01C3/08; salts of cyanic acid C01C3/14; salts of cyanamide C01C3/16; thiocyanates C01C3/20; {double sulfates of magnesium with sodium or potassium C01D5/12; with other alkali metals C01D15/00, C01D17/00}) - C01G: COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F (metal hydrides {monoborane, diborane or addition complexes thereof} C01B6/00; salts of oxyacids of halogens C01B11/00; peroxides, salts or peroxyacids C01B15/00; thiosulfates, dithionites, polythionates C01B17/64; compounds containing selenium, or tellurium C01B19/00; binary compounds of nitrogen with metals C01B21/06; azides C01B21/08; {compounds containing nitrogen, other non-metals and metal C01B21/082}; metal amides C01B21/092; nitrites C01B21/50; {compounds of noble gases C01B23/0005}; phosphides C01B25/08; salts of oxyacids of phosphorus C01B25/16; carbides C01B32/90; compounds containing silicon C01B33/00; compounds containing boron C01B35/00; compounds having molecular sieve properties but not having base-exchange properties C01B37/00; compounds having molecular sieve and base-exchange properties, e.g. crystalline zeolites, C01B39/00; cyanides C01C3/08; salts of cyanamide C01C3/16; thiocyanates C01C3/20) - C01P: INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS ## Abstract Ketones may be produced in high yields from glycerides of short chain fatty acids by reaction with a carboxylic acid. The reaction is conducted in the presence of a catalyst and under conditions effective for ketonization of decanoate with the carboxylic acid to produce free ketones. Reaction of a glyceride comprising at least one ester of decanoic acid with a carboxylic acid selected from acetic acid and/or propionic acid produces 2-undecanone and/or 3-dodecanone, respectively. Catalysts of the formula FemCenAlpOx, wherein m is between about 0.2 to about 0.6, n is about 0.2, p is between about 0.6 to about 0.2, and x is greater than 0, produce significantly higher yields of the ketones than other known metal oxides. ## Claims ### Claim 1 A method for production of ketones from glycerides comprising reacting a glyceride comprising at least one ester of decanoic acid with a carboxylic acid selected from the group consisting of acetic acid and propionic acid in the presence of a catalyst and under conditions effective for ketonization of decanoate with said carboxylic acid to produce a ketone comprising 2-undecanone or 3-dodecanone. ### Claim 2 (depends on 1) The method of claim 1 wherein said glyceride comprises a monoglyceride, diglyceride, triglyceride or combinations thereof. ### Claim 3 (depends on 2) The method of claim 2 wherein said glyceride comprises a triglyceride. ### Claim 4 (depends on 1) The method of claim 1 wherein said glyceride comprises a plant oil. ### Claim 5 (depends on 4) The method of claim 4 wherein said plant oil is selected from the group consisting of cuphea oil, palm oil and coconut oil. ### Claim 6 (depends on 1) The method of claim 1 wherein said carboxylic acid is present in a molar excess relative to said glyceride. ### Claim 7 (depends on 6) The method of claim 6 wherein said molar ratio of said carboxylic acid relative to said glyceride is greater than or equal to 15:1. ### Claim 8 (depends on 1) The method of claim 1 wherein said catalyst comprises a metal oxide or metal carbonate. ### Claim 9 (depends on 1) The method of claim 1 wherein said catalyst comprises FemCenAlpOx wherein m is between about 0.2 to about 0.6, n is about 0.2, p is between about 0.6 to about 0.2, and x is greater than 0. ### Claim 10 (depends on 9) The method of claim 9 wherein said catalyst comprises Fe0.5Ce0.2Al0.3Ox. ### Claim 11 (depends on 1) The method of claim 1 further comprising recovering said ketone. ### Claim 12 (depends on 11) The method of claim 11 wherein said reacting further produces glycerol and CO2 and said recovery comprises separating said ketone from said glycerol. ### Claim 13 (depends on 12) The method of claim 12 wherein said separating comprises distillation. ### Claim 14 (depends on 1) The method of claim 1 wherein said conditions comprise a temperature greater than approximately 350° C. and substantially in the absence of oxygen. ### Claim 15 (depends on 1) The method of claim 1 wherein said carboxylic acid comprises acetic acid and said ketone comprises 2-undecanone. ### Claim 16 (depends on 1) The method of claim 1 wherein said carboxylic acid comprises propionic acid and said ketone comprises 3-dodecanone. ### Claim 17 (depends on 1) The method of claim 1 wherein said reacting said glyceride with said carboxylic acid to produce said ketone is conducted in a single step. ### Claim 18 (depends on 17) The method of claim 17 wherein said reacting does not comprise hydrolyzing the glyceride to free decanoic acid. ### Claim 19 A metal oxide comprising FemCenAlpOx wherein m is between about 0.2 to about 0.6, n is about 0.2, p is between about 0.6 to about 0.2, and x is greater than 0. ### Claim 20 (depends on 19) The metal oxide of claim 19 comprising Fe0.5Ce0.2Al0.3Ox.