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Office Patented Aug United States Patent 3,201,431 Office Patented Aug. 7, 1965 2 ing fatty acids from fatty oils by hydrogenating the oils 3,20,431 without causing an appreciable increase in saturation of SELECTWE HYDROGENATION OF MALWARLFC other unsaturated acids in the oils. AND STERCULC ACDS IN COTONSEED CHL Dwight R. Meaker, Chicago, and Karl F. Mattil, BDown Still another object of this invention is to provide a ers (Grove, B., assignors to Swift & Company, Chicago, process for hydrogenating cottonseed oils under special s E., a corporatiosa of linois conditions whereby the malvalic and sterculic acids pre No HDrawing. Filled Mar. 19, 1963, Ser. No. 266,214 sent in the oil are converted to the saturated forms with 10 Claims. (C. 260-409) out appreciable hydrogenation of the linoleic acid radi cals of the triglyceride. This invention relates to a method for the selective hy- l0 Other objects and advantages of this invention will be drogenation of cyclopropenyl double bonds in fatty acid come readily apparent to those skilled in the art from the esters present in some vegetable oils, and more particularly following detailed description. to the removal of Halphen acids from fatty oils. Generally, the instant invention comprises hydrogenat Malvalic and sterculic acids which contain cyclopro ing fatty oils which contain malvalic and sterculic acids, penyl double bonds have been found to be associated with 15 such as cottonseed oil, selectively to inactivate and re the triglycerides of certain vegetable oils. The concen move these Haiphen acids without appreciable hydrogena tration of these acids in cottonseed oils is said to be up to tion (and resultant increase in the saturation) of the un about 3%. The well-known Halphen test for cottonseed saturated acids present in the oil, and without appreciable oil is caused by the presence of these acids, and thus the trans acid formation. This selectivity may be effected by acids are then referred to as “Halphen' acids. This test 20 hydrogenation at higher than normal temperatures and is based on the development of a red color when malvalic lower than normal pressures, in the presence of a hydro or sterculic acids, or oils containing these acids are heat genation catalyst. In this method the temperature and ed with a solution of sulfur in carbon disulfide and iso pressure must be maintained within carefully controlled amyl alcohol. No Such red color is formed if these acids ranges, discussed more fully hereinafter. This selectivity are not present or if they have previously been hydro- 25 may be attained without the rigid criticality in tempera genated. The Halphen test is widely used to identify cot ture and pressure ranges by the use of a small amount of tonseed oil in mixtures with other vegetable oils, particu ammonia or ammonium hydroxide to regulate catalyst larly to detect the adulteration of olive oil with cotton activity, and thereby regulate the rate of reaction in the seed oil. selective hydrogenation. The greatest problems presented by the Halphen acids 30 Malvalic and sterculic acids are cyclopropane acids. arise in connection with the feeding of hens with a diet Malvalic acid is the 17-carbon methylene-substituted acid containing fat and oil containing materials. The presence similar to oleic acid and having the following structure: of the Halphen acids in oil-containing feeds adversely af fects the quality of the eggs produced. While lower levels of sterculic and malvalic acids, equivalent to that con- 85 tained in about 5 grams of oil per day, apparently do not adversely affect egg production levels, they may cause pink Sterculic acid has a very similar structure, having one egg-white discoloration in stored eggs; and ingestion of more carbon atom, as follows: higher levels of the acids rapidly reduces hatchability. Chicks incubated from such eggs have a high mortality 40 CHCH)-cs C-(CH),c O OE rate. In addition to possible pinking of the albumin, eggs CE from hens which have been fed Halphen acids show ele These acids give a positive reaction to the Halphen test. vated yolk pH, Salmon-colored yolks, and iron content On hydrogenation of the acids, however, the cyclopropene alterations, as well as unusually high saturated fat con rings of the acids are converted to dihydro and/or tetra tent of the egg lipides. All these undesirable character- 45 hydro products which react negatively to the Halphen istics in eggs are apparently caused by the presence of test. The ratio of malvalic to sterculic acid is on the order Halphen acids in the feed given the hens. of about 10 to 1 in cottonseed oil. The acids are not Although tests have not been conducted to determine present in the oils as free acids, but in the form of the toxicity of Halphen acids to humans, the acids are triglycerides. known to disturb the potassium to sodium ratio in the 50 Since it is desirable to maintain the maximum pos blood of rats, and are apparently toxic to non-ruminants. sible unsaturation in cottonseed oils and also to avoid it is known that hydrogenation of an oil containing trans acid formation, standard hydrogenation processes cyclopropenyl double bonds in the fatty acid will convert are unsuitable for the inactivation of the malvalic and malvalic and sterculic acids to saturated derivatives. How sterculic acids from the oils by converting these acids to ever, under normal conditions of hydrogenation in the the dihydro derivatives. However by selectively hy case of cottonseed oil, there is considerable conversion drogenating under carefully controlled reaction conditions of linoleic acids to oleic acid as well as trans isomer for the desired result can be achieved. mation. Thus, if cottonseed oil is hydrogenated under In one embodiment of the invention, the hydrogenation conventional conditions at a temperature of 120 to 200 is carried out at a higher than normal temperature used C. and a positive hydrogen pressure of 0 to 50 pound 60 in cembination with a lower than normal pressure. The gauge with 0.1 to 0.2% reduced nickel catalyst until the reaction is conducted with agitation, for a very short Halphen test is negative, the oil will contain approxi period of time, and in the presence of a hydrogenation mately 20-45% linoleic acid and 10-40% trans acid. catalyst. The operating temperature range, using this Even under normal conditions of selective hydrogenation, method, is 200 to 300° C. and preferably about 220 170-200° C. and 0-5 pounds gauge pressure, consider- 65 230° C. Apparently this abnormally high temperature able linoleic acid (about 10%) is hydrogenated before activates the Halphen acids for selective hydrogenation the Halphen acids are completely inactivated. to the dihydro and tetrahydro branched-chain derivatives. It is therefore an object of the instant invention to The selectivity necessary for this reaction can be achieved provide an improved process for inactivating the Halphen with an active nickel catalyst and a limited amount of acids present in fatty materials. 70 hydrogen. Another object of the instant invention is to provide an The amount of catalyst used may vary between about improved process for inactivating cyclopropenyl contain 0.01 and 1.0% based on the oil being hydrogenated, - - - 3, 201431 3 4. however, about 0.1-0.2% is preferred when a nickel cata to 180 minutes are generally sufficient to produce the desired Halphen acid-free product without causing ap lyst is used. Although nickel is the preferred catalyst, platinum or palladium may also be used. preciable saturation in the oil. This enbodiment of The limited amount of hydrogen necessary to pro instant invention is illustrated by the following specific mote the desired selectivity is supplied by carrying out 5 examples. the hydrogenation at subatmospheric pressures. While Example I/ any negative hydrogen pressure facilitates successful se lective hydrogenation, pressures below about 10 pounds A Sample of refined bleached cottonseed oil contail per Square inch absolute (5 pounds gauge below atmos ing 52% linoleic acid and 3% trans acid was hydrogezai pheric) are preferred. The only lower limit cn the re O ed at 235 C. and 30 pounds gauge pressure for 30 nin . duced pressures which can be used is that dictated by utes in the presence of 0.15% nickel catalyst and 0.5% equipment limitations. ammoniuin hydroxide. The hydrogenated oil contained Hydrogenation reactions under the above conditions 50.8% linoieic acid and 5.2% trans acid, and gave a may generally be carried cut by passing hydrogen into negative Halphen test. the oil and agitating and heating the oil for a period of about 0.1 to 10 minutes, a period of about 30 seconds Examiple V to one minute being preferred. This reaction title pro duces an oil which does not react to the Halphen test, A sampie of refined bleached cottonseed oil contaiting and yet does not have appreciable amounts of its unsat 53% linoleic acid and 3.3% trans acid was hydrogenated urated inoleic acids hydrogenated to more saturated acids. at 200° C. and 100 pounds gauge pressure for 45 min he following specific examples are designed to illus utes in the presence of 0.3% nickel catalyst and 0.3% trate the above described process, and should be consid ammonium hydroxide. The hydrogenated oil, which ered illustrative only and not limiting of the instant in contained 52% linoleic acid and 5% trans acid gave a vention. negative Haiphen test. Exainple I Example VI A sample of refined bleached cottonseed oil contain A sample of refined bleached cotton seed oil containing ing 53% linoleic acid and 3.3% trans acid was hy 53% linoleic acid and 3.3% trans acid was hydrogenated drogenated at 235 C.
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