Methods for preparing phenolic branched chain alkyl fatty acids or esters thereof and methods for killing microorganisms
Inventors
Lew, HELEN N. • Wagner, Karen • Fan, Xuetong • Nunez, Alberto • Moreau, Robert A. • Haas, Michael J. • YAN, ZONGCHENG
Assignees
US Department of Agriculture USDA
Publication Number
US-10144694-B2
Publication Date
2018-12-04
Expiration Date
2036-03-01
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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.
Core Innovation
The invention relates to methods for preparing phenolic branched chain fatty acids or alkyl esters thereof by subjecting at least one phenolic compound, unsaturated fatty acids (6 to 25 carbon atoms) or their alkyl esters, and H-ferrierite zeolite catalyst in a pressurized container with distilled water or alcohol and a nitrogen atmosphere at about 100° C. to 400° C. and a pressure of about 10 to 1000 psi. The process yields saturated phenolic branched chain fatty acids or alkyl esters with yields greater than about 70 wt % where at least one phenolic group is attached on the fatty acid alkyl chain.
The problem addressed is the instability of unsaturated fatty acids at elevated temperatures, limiting their applications. There is a need for biobased industrial fluids with improved properties such as lower melting points, better lubricity, thermal and oxidative stability, and biodegradability. Existing methods for the production of branched chain fatty acids use homogeneous catalysts or give low yields or produce undesirable byproducts. Previous heterogeneous catalytic systems gave moderate yields and could not be efficiently recycled or reused. Further, there is a concern over the effectiveness and environmental impact of current sanitizers for foodborne pathogens, necessitating development of novel, environmentally friendly antimicrobials derived from renewable resources.
The invention also discloses methods for killing microorganisms on or in objects by contacting them with an effective microorganisms killing amount of compositions comprising the phenolic branched chain fatty acids or alkyl esters produced by these methods. The phenolic branched chain fatty acids show antimicrobial properties, particularly against Gram-positive bacteria, thus addressing the need for more effective and environmentally friendly antimicrobials.
Claims Coverage
The patent contains seven inventive features corresponding to independent claims related to methods for preparing phenolic branched chain fatty acids or alkyl esters and their use for killing microorganisms.
Method for preparing phenolic branched chain fatty acids or alkyl esters in a pressurized container
Subjecting (a) at least one phenolic compound, (b) unsaturated fatty acids having 6 to 25 carbon atoms or their alkyl esters, and (c) H-ferrierite zeolite catalyst in the presence of distilled water or alcohol and a nitrogen atmosphere at about 100° C. to 400° C. and about 10 to 1000 psi pressure, isolating saturated phenolic branched chain fatty acids or alkyl esters with yields greater than about 70 wt %, where at least one phenolic is on the fatty acid alkyl chain and the ratio of phenolic compound to unsaturated fatty acids or esters is about 100 to about 1.
Method for producing phenolic branched chain fatty acids with specific unsaturation and phenol numbers
Using a mixture of unsaturated fatty acids having 6 to 25 carbon atoms (number of unsaturated bonds is 3) and at least one phenolic compound, catalyzed by H-ferrierite zeolite as above, producing phenolic branched chain fatty acids or esters having one, two, or three phenols on the fatty acid alkyl chain.
Method for killing microorganisms using a composition comprising phenolic branched chain fatty acids or alkyl esters
Contacting an object with an effective microorganisms killing amount of a composition comprising phenolic branched chain fatty acids or alkyl esters thereof, optionally with a carrier, where the phenolic branched chain fatty acids or esters may be produced by the specified catalytic method.
Targeting broad range microorganisms including Gram-positive and Gram-negative bacteria
The composition comprising phenolic branched chain fatty acids or alkyl esters is effective against microorganisms selected from Gram-positive bacteria, Gram-negative bacteria, or mixtures thereof.
Usage of phenolic branched chain fatty acid or alkyl ester mixtures
The composition used in the microorganism killing method can be a mixture of phenolic branched chain fatty acids or alkyl esters thereof produced by the catalytic method as defined.
The claims cover methods for producing phenolic branched chain fatty acids or esters via catalytic processes using H-ferrierite zeolite and their use in methods to kill microorganisms. The inventive features emphasize the production conditions, compositions with varied phenol substitutions, and applications for antimicrobial compositions effective against specific microorganism groups.
Stated Advantages
The phenolic branched-chain fatty acids have improved antimicrobial properties particularly against Gram-positive bacteria, which are stronger than mixtures of phenol and oleic acid.
The method achieves high yields (greater than about 70 wt %) and high conversions (greater than 85%) of phenolic branched-chain fatty acids with minimized byproducts such as dimers and linear chain fatty acids.
The heterogeneous catalytic process uses a recyclable, reusable H-ferrierite zeolite catalyst, providing an efficient production method.
The phenolic branched-chain fatty acids have lower melting and cloud points, improving their performance in biobased industrial applications requiring fluidity at lower temperatures.
Documented Applications
Use as antimicrobial agents for killing microorganisms on or in objects, including food surfaces, fresh-cut produce, meats, poultry, seafood, eggs, nuts, fruits, vegetables, drinks, food-packages, cosmetics, pharmaceuticals, sanitizers, and non-food products.
Treatment and improvement of microbial safety of foods by applying compositions comprising the phenolic branched-chain fatty acids or esters.
Potential use in treating skin diseases caused by Propionibacterium acnes.
Applications as coating materials, corrosion inhibitors, lubricants, aqueous rust inhibitors, fuel additives, and stain treatment agents for textiles.
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