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UNITED STATES PATENT Office Patented June 6, 1944 2,350,583 UNITED STATES PATENT office DRYNG OS Theodore F. Bradley, Stamford, Conn., assignor to American Cyananid Company, New York, N. Y., a corporation of Maine No Drawing. Application February 8, 1941, Seria No. 378,060 3 Claims. (C. 260-405.6) This invention relates to improvements in dry may be used for the isomerization of any unsat ing oils and the higher fatty acids which they urated fatty acid or acids the molecules of which contain. The invention includes the prepara contain at least two non-conjugated double tion of such oils by isomerizing polyunsaturated bonds. In most cases the isomerization treat higher fatty acids to bring about a relatively high ment will be applied to mixed fatty acids only content of conjugated double bonds therein foll Some of which are polyunsaturated as this is the lowed by esterification of the isomerized acids forn) in which these acids are found in vegetable with a polyhydric alcohol. The invention also and fish oils of relatively high iodine values. It includes a new and improved method of isomeriz is an important advantage of the invention, how ing polyunsaturated fatty acids as Well as cer 0. ever, that it can be applied with success to fatty tain new drying oils prepared therefron, acid mixtures containing relatively low percen It is known that the drying properties of poly tages of non-conjugated, polyunsaturated fatty unsaturated higher fatty acids, winen employed acids, as is the case in soya bean fatty acids, as in the form of triglycerides, oil-modified alkyd well as to the more highly polyunsaturated fatty resins and the like, are influenced by the posi 5 acid mixtures such as those of linseed oil. tions of their double bonds with respect to each My isomerization treatment is especially other. If these double bonds are in conjugation adapted for improving the drying properties of (i. e. Separated by only one single bond) the oil the polyhydric alcohol esters of the fatty acid has better drying properties than a similar oil mixtures obtained from such vegetable oils as lin having an equal number of non-conjugated 20 seed oil, SOya bean oil, chia seed oil, perilla oil, double bonds. Thus, for example, tung oil dries poppy seed oil, cottonseed oil, sunflower seed oil faster than linseed oil because the three double and the like as well as the polyunsaturated fatty bonds of the eleostearic acid found in tung oil acids of fish oils, and other polyunsaturated are in conjugation whereas the double bonds of fatty acids of 18 or more carbon atoms. As a the linoleic and linolenic acids of linseed oil are 25 practical matter the oils from which the fatty not. It is a principal object of the present in acids are obtained should have a relatively high vention to provide a relatively quick and inex iodine value, at least on the order of 110-130, as pensive method of isomerizing polyunsaturated otherwise there are not sufficient polyunsaturated higher fatty acids to bring the double bonds acids present to warrant the treatment. It thereof into conjugation so that the polyhydric 30 should also be noted that there is no advantage alcohol esters thereof will have improved drying in applying my isomerization process to eleo properties. stearic acid, or to oils such as tung oil or oiticica, I have found that the double bonds of poly oil which contains large quantities of polyun unsaturated higher fatty acids can be brought saturated acids having double bonds that are into conjugation within a few hours by heating 35 already in conjugation, although the treatment an aqueous solution of the soaps thereof with of such acids is not excluded from the invention excess alkali in a pressure vessel at temperatures in its broadest aspects. Thus, for example, I above about 200° C. and under the corresponding have heated a mixture of 75 parts by weight of autogenic pressures. I have found that by heat tung oil acids, 75 parts of potassium hydroxide ing the acids at these temperatures in the form 40 and 100 parts of distilled water in an autoclave of a solution of their soaps in water the iso at 225-230° C. for 2.5 hours and liberated the re merization or rearrangement of the double bonds suiting isomerized fatty acids from their potas proceeds much faster than would otherwise be sium soaps. The resulting amber colored acids the case, and an equilibrium favoring a relative were partly liquid at room temperature, where ly high content of conjugated double bonds is 45 as the original acids were crystalline, and frac reached in from one to three hours. The most tionation of the isomerized acids by distillation favorable temperature range appears to be from at 250-300° C. under 1 mm. pressure followed by 200° to 250° C., for above this range excessive analysis of the fractions showed that the degree losses of the acids by polymerization may OCCur. of triple conjugation characteristic of eleostearic Insofar as I have been able to determine, my 50 acid had been substantially reduced while cor invention is perfectly general in character and responding quantities of acids having only dou 2,850,588 ble conjugation had been formed. While this have been isomerized to this extent exhibit faster constitutes further proof that the conditions ob and better drying properties as well as heat taining during the heating step brought about bodying characteristics than are possessed by the equilibrium favoring double conjugation, ester original oils from which these acids were ob fication of the isomerized tung oil acids with tained, and since the isomerization equilibrium . glycerine did not give as good a drying oil as the can be attained rapidly in ordinary equipment Original tung oil. this improvement is relatively inexpensive. In many cases it is feasible to subject higher When my isomerization treatment is applied fatty acid mixtures having a relatively low Con to the fatty acids of linseed oil and to dehydrated tent of polyunsaturated fatty acids to a prelim castor oil fatty acids, I find that the resulting inary treatment that will separate out the more fatty acid mixtures have very similar properties. highly saturated fatty acids such as stearic acid, By preparing the esters of the isomerized fatty palmitic acid and the like. Thus, for example, acids from these two sources with glycerine, the crude fatty acids obtainable by saponifica pentaerythritol and dipentaerythritol I have ob tion of soya bean oil, upon refrigeration at about S tained new drying oils which contain about 40% 4 to 12 below zero, centigrade, for 24 hours will of esterified octadecadienic acids in which the crystallize out substantial quantities of stearic two double bonds are in conjugation. These oils and palmitic acids, which can be removed by fill have excellent drying properties, and are in tration, and the percentage of doubly unsatu ed as specific features of the present inven rated fatty acids in the remaining oil is of course O increased substantially. The invention will be illustrated in greater de The content of fatty acids having conjugated tail by reference to the following specific exam double bonds can also be increased by vacuum ples. The results obtained in these examples distilation of the isomerized fatty acid mixtures. were evaluated by the spectroscopic method re I have found that the acids in which conjugation ferred to in volume 37 of the Biochemical Jour has occurred have slightly higher boiling points na, pages 138-141 (1937) and described in great at reduced pressures than the corresponding non er detail by the present applicant in Industrial conjugated acids, so that fractions rich in con and Engineering Chemistry, volume 32 (1940), jugated acids can be separated by this method. page 963. By this means it was possible to make Ordinarily a flash distillation is preferred, as con 30 quantitative determinations of the content of siderable polymerization of the conjugated acids doubly, triply and quadruply conjugated higher is encountered if they are maintained at ele fatty acids in fatty acid mixtures within very wated temperatures for too long a time. narrow limits of error. It should be understod, Another feature of the invention which is im however, that while these examples may describe portant from a commercial point of view resides 35 in detail some of the more specific features of the in the direct treatment of glyceride oils them invention, they are given primarily for purposes selves by my alkali isomerization process. When of illustration and the invention in its broader such triglycerides as soya bean oil, linseed oil, aspects is not limited thereto. perilla oil and the like are charged into an auto In Examples 2, 3, 4 and 7 some of the isom clave and heated with an aqueous solution of an erized fatty acids have been described by name. alkali the oil is immediately saponified and the It is quite possible, however, that the conjugated soaps of its fatty acids are formed. When the double bond systems of these acids may be one solution contains an excess of alkali over that or two carbon atoms removed from the positions necessary to saponify all the fatty acids and suf assigned, and therefore these examples should cient water to dissolve the resulting Soaps it be regarded as indicative of the results obtained is unnecessary to carry out the saponification as a rather than as proof of the exact structural for separate step, but the autoclave may be directly mulas of these compounds. heated to 200-250 C. and the contents main Eacample 1 tained at these temperatures until conjugation of the double bonds of the fatty acids is effected.
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