Method of conjugating double bonds in drying oils
AssigneeArcher Daniels Midland Company
InventorRonald T. Sleeter
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Abstract
The invention provides a method of conjugating double bonded drying oil so that a relatively low cost linseed oil, for example, can replace the more expensive, naturally conjugated tung oil which has been used heretofore. The conjugation is brought about by the use of ruthenium as a catalyst, with formic or a similar acid providing a synergistic augmentation of the reaction. The conjugated oil may have many uses, but a major object is to provide a way to enhance a phenolic resin adhesive used on wood and wood products.
Claims32
A one phase method of conjugating methylene interrupted organic compounds comprising:
- solubilizing ruthenium in a methylene interrupted organic compound to a level which provides a homogenous catalysis;
- reacting methylene interrupted organic compounds, in the absence of oxygen and in the presence of an acid, with said solubilized ruthenium compound homogenous catalyst selected from the group consisting of organo-ruthenium complexes, soluble ruthenium metal, ruthenium salts, and ruthenium covalent compounds, said ruthenium being a metal which is about 5 ppm and not more than about 200 ppm, based upon the weight of the methylene interrupted organic compound.
A method of conjugating methylene interrupted organic compounds comprising:
- solubilizing ruthenium in methylene interrupted organic compound to a level which provides a homogenous catalysis;
- reacting methylene interrupted organic compounds, in the absence of oxygen and in the presence of an acid, and with said solubilized organo-ruthenium complexes, the ruthenium complex being selected from the group consisting of:
- dodecacarbonyl triruthenium, dichlorotris (triphenylphosphene) ruthenium (II) and ruthenium (III) 2,4-pentanedionate.
A method of conjugating methylene interrupted organic/compounds comprising:
- solubilizing ruthenium in a methylene interrupted organic compound to a level which provides homogenous catalysis;
- reacting methylene interrupted organic compounds, in the absence of oxygen and in the presence of an acid, with said solubilized a ruthenium compound selected from the group consisting of organoruthenium complexes, soluble ruthenium metal, ruthenium salts, and ruthenium covalent compounds;
- and a conventional antioxidant.
A method of conjugating methylene interrupted vegetable oils comprising:
- solubilizing ruthenium in a methylene interrupted organic compound to a level which provides homogenous catalysis;
- reacting methylene interrupted vegetable oils, in the absence of oxygen and in the presence of formic acid, with a ruthenium compound chosen from the group consisting of organoruthenium complexes, soluble ruthenium metal, ruthenium salts, and ruthenium covalent compounds.
A modified methylene interrupted common vegetable oil having an iodine value of at least 120, said oil being prepared by first solubilizing ruthenium in a methylene interrupted organic compound to a level which provides homogenous catalysis and then reacting the common vegetable oil in the absence of oxygen and in the presence of an acid, with a solubilized ruthenium compound chosen from the group consisting of organo-ruthenium complexes, soluble ruthenium metal, ruthenium salts, and ruthenium covalent compounds.
A method of conjugating methylene interrupted vegetable oils comprising the steps of:
- (a) selecting at least one methylene interrupted fatty acid oil from a group consisting of linseed, fish, soybean, tall, tung, corn, sunflower, safflower, castor, and oiticica;
- (b) reacting the oil selected in step (a) a ruthenium catalyst taken from a group consisting of organo-ruthenium complexes, soluble ruthenium metal, ruthenium salts, and ruthenium covalent compounds to form a homogeneous catalyst;
- (c) conducting the reaction of step (b) in an absence of oxygen;
- adding a methylene interrupted vegetable oil selected from the group consisting of linseed, soybean, corn, sunflower, safflower, castor, and oiticica;
- and
- (d) adding a synergistic reaction augmentation material taken from a group consisting of formic acid, gaseous hydrogen chlorine, benzoic acid, glacial acetic acid, oxalic acid, ethanol, glycerine, and triglycerol mono oleates.
Dependencies are inferred from the claim text.