# US 2017/0253552 A1 · Methods for Preparing Phenolic Branched Chain Alkyl Fatty Acids or Esters Thereof and Methods for Killing Microorganisms > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2017/0253552 A1 - Document ID: US20170253552A1 - Status: Published application - Kind: A1 - Application number: 15/057,632 - Filed: 2016-03-01 - Published: 2017-09-07 - Earliest claimed: 2016-03-01 - Assignees: The United States of America as represented by the Secretary of Agriculture - Applicants: The United States of America, as represented by the Secretary of Agriculture; School of Chemistry and Chemical Engineering, South China University of Technology - Inventors: HELEN N. Lew; KAREN WAGNER; XUETONG FAN; ALBERTO NUNEZ; ROBERT A. MOREAU; MICHAEL J. HAAS; ZONGCHENG YAN - Web page: https://patentgrep.com/patent/US20170253552A1 ## CPC - C07C 51/353: by isomerisation; by change of size of the carbon skeleton - A01N 37/02: Saturated carboxylic acids or thio analogues thereof; Derivatives thereof - A01N 37/38: having at least one oxygen or sulfur atom attached to an aromatic ring system - C07C 51/367: by introduction of functional groups containing oxygen only in singly bound form - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS ## Abstract Disclosed are methods for preparing phenolic branched chain fatty acids or alkyl esters thereof, involving subjecting in a pressurized container (a) at least one phenolic compound, (b) unsaturated fatty acids having 6 to 25 carbon atoms, alkyl esters thereof, or mixtures thereof, and (c) H-ferrierite zeolite catalyst in the presence of distilled water or alcohol and a nitrogen atmosphere at a temperature of about 100° C. to about 400° C. and a pressure of about 10 to about 1000 psi, and isolating saturated phenolic branched chain fatty acids or alkyl esters thereof or mixtures thereof. Also disclosed are methods for killing microorganisms on or in an object, involving contacting said object with an effective microorganisms killing amount of a composition comprising phenolic branched chain fatty acids or alkyl esters thereof, and optionally a carrier; the phenolic branched chain fatty acids or alkyl esters thereof may be produced by the methods described herein. ## Claims ### Claim 1 A method for preparing phenolic branched chain fatty acids or alkyl esters thereof, said process comprising subjecting in a pressurized container (a) at least one phenolic compound, (b) unsaturated fatty acids having 6 to 25 carbon atoms, alkyl esters thereof, or mixtures thereof, and (c) H-ferrierite zeolite catalyst in the presence of distilled water or alcohol and a nitrogen atmosphere at a temperature of about 100° C. to about 400° C. and a pressure of about 10 to about 1000 psi, and isolating saturated phenolic branched chain fatty acids or alkyl esters thereof or mixtures thereof; wherein the ratio of said at least one phenolic compound: said unsaturated fatty acids or alkyl esters thereof is about 100 to about 1, wherein the yield of said saturated phenolic branched chain fatty acids is greater than about 70 wt %, and wherein there is at least one phenolic on the fatty acid alkyl chain. ### Claim 2 (depends on 1) The method according to claim 1, wherein the ratio of said at least one phenolic compound: said unsaturated fatty acids or alkyl esters thereof is about 100 to about 1. ### Claim 3 (depends on 1) The method according to claim 1, wherein said unsaturated fatty acids have 10 to 22 carbon atoms. ### Claim 4 (depends on 1) The method according to claim 1, wherein said unsaturated fatty acids have 16 to 22 carbon atoms. ### Claim 5 (depends on 1) The method according to claim 1, wherein the number of unsaturated bonds in said unsaturated fatty acids is 1 to 3. ### Claim 6 (depends on 1) The method according to claim 1, wherein the yield of dimers is less than about 15 wt %. ### Claim 7 (depends on 1) The method according to claim 1, wherein the yield of linear chain fatty acid is less than about 18 wt %. ### Claim 8 (depends on 1) The method according to claim 1, wherein the conversion of said unsaturated fatty acids or alkyl esters thereof is greater than about 85%. ### Claim 9 (depends on 1) The process according to claim 1, wherein said process further comprises recycling said catalyst. ### Claim 10 (depends on 9) The process according to claim 9, wherein said process further comprises washing said catalyst with an acid solution or solvent and heating said catalyst. ### Claim 11 (depends on 10) The process according to claim 10, wherein said solvent is a polar solvent or non-polar solvent. ### Claim 12 (depends on 9) The process according to claim 9, wherein said catalyst is heated in an acid solution at about 55° C. for about 24 hours. ### Claim 13 (depends on 10) The process according to claim 10, wherein said catalyst is dried at about 115° C. for about 20 hours. ### Claim 14 (depends on 10) The process according to claim 10, wherein said catalyst is calcined at about 500° C. for at least 5 hours. ### Claim 15 (depends on 1) The process according to claim 1, said process comprising subjecting in a pressurized container (a) at least two phenolic compounds, (b) unsaturated fatty acids having 6 to 25 carbon atoms, alkyl esters thereof, or mixtures thereof, and (c) H-ferrierite zeolite catalyst in the presence of distilled water or alcohol and a nitrogen atmosphere at a temperature of about 100° C. to about 400° C. and a pressure of about 10 to about 1000 psi, and isolating saturated phenolic branched chain fatty acids or alkyl esters thereof or mixtures thereof; wherein the ratio of said at least one phenolic compound: said unsaturated fatty acids or alkyl esters thereof is about 100 to about 1, wherein the yield of said saturated phenolic branched chain fatty acids is greater than about 70 wt %, and wherein there is at least one phenol on the fatty acid alkyl chain. ### Claim 16 A method for killing microorganisms on or in an object, said method comprising contacting said object with an effective microorganisms killing amount of a composition comprising phenolic branched chain fatty acids or alkyl esters thereof, and optionally a carrier. ### Claim 17 (depends on 16) The method according to claim 16, wherein said phenolic branched chain fatty acids or alkyl esters thereof is produced by a method comprising subjecting in a pressurized container (a) at least one phenolic compound, (b) unsaturated fatty acids having 6 to 25 carbon atoms, alkyl esters thereof, or mixtures thereof, and (c) H-ferrierite zeolite catalyst in the presence of distilled water or alcohol and a nitrogen atmosphere at a temperature of about 100° C. to about 400° C. and a pressure of about 10 to about 1000 psi, and isolating saturated phenolic branched chain fatty acids or alkyl esters thereof or mixtures thereof; wherein the ratio of said at least one phenolic compound : said unsaturated fatty acids or alkyl esters thereof is about 100 to about 1, wherein the yield of said saturated phenolic branched chain fatty acids is greater than about 70 wt %, and wherein there is at least one phenolic on the fatty acid alkyl chain. ### Claim 18 (depends on 16) The method according to claim 16, where said microorganisms are selected for the group consisting of Gram-positive bacteria, Gram-negative bacteria, and mixtures thereof. ### Claim 19 (depends on 16) The method according to claim 16, where said microorganisms are Gram-positive bacteria. ### Claim 20 (depends on 16) The method according to claim 16, where said microorganisms are Gram-negative bacteria.