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(12) United States Patent (10) Patent No.: US 6,774,252 B2 Strohmaier Et Al

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(12) United States Patent (10) Patent No.: US 6,774,252 B2 Strohmaier Et Al USOO6774252B2 (12) United States Patent (10) Patent No.: US 6,774,252 B2 Strohmaier et al. (45) Date of Patent: Aug. 10, 2004 (54) METHOD FOR MANUFACTURING FATTY 5,425,963 A 6/1995 Lajoie ACID CALCUM SALTS FROM HIGH 6,229,031 B1 5/2001 Strohmaier ................. 544/156 GLYCERIDE CONTENT OILS 6,521.249 B2 2/2003 Blocket al. 2002/O127259 A1 9/2002 Orthoefer ................... 424/409 (75) Inventors: George K. Strohmaier, Medina, OH FOREIGN PATENT DOCUMENTS (US); Eiler D. Frederiksen, Henderson, NV (US); Nestor Daniel Luchini, EP 209509 9/1991 Naperville, IL (US) EP O678246 A1 10/1995 ............ A23K/1/OO GB 2007 O76 5/1979 .......... A23K/1/175 IL 125096/3 6/1998 (73) Assignee: Norel Acquisition Corp., Fairlawn, OH IL 125097/3 6/1998 (US) JP 8/275734 10/1996 JP 8/336360 12/1996 (*) Notice: Subject to any disclaimer, the term of this WO WO 97/42838 11/1997 ............ A23K/1/16 patent is extended or adjusted under 35 WO 99/66876 12/1999 U.S.C. 154(b) by 0 days. WO 99/66877 12/1999 WO O1/62698 8/2001 (21) Appl. No.: 10/316,486 * cited by examiner (22) Filed: Dec. 11, 2002 Primary Examiner Deborah D. Carr Prior Publication Data (74) Attorney, Agent, or Firm-Synnestvedt & Lechner (65) LLP US 2003/0092924 A1 May 15, 2003 (57) ABSTRACT Related U.S. Application Data A method for the preparation of fatty acid calcium Salts, (62) Division of application No. 09/990,784, filed on Nov. 14, which includes the steps of: 2001, now Pat. No. 6,576,667. (a) providing a fatty acid feedstock having a glyceride (51) Int. Cl................................................. C07C 51/00 content between about 30 and about 60% by weight; (b) adding to the feedstock from about 2 to about 3 (52) - - - - - - - - - - 554/156 equivalents of calcium oxide relative to the feedstock, (58) Field of Search .......................................... 554/156 So that a reactive admixture is formed; and (56) References Cited (c) adding to the reactive admixture from about 2 to about 5 equivalents of water relative to the calcium oxide So U.S. PATENT DOCUMENTS that the calcium oxide hydrates and neutralizes the fatty 4,642,317 A 2/1987 Palmquist et al. acids to form calcium Salts. Fatty acid calcium Salts 4,826,694 A 5/1989 McAskie containing eicosapentaenoic acid and decosahexaenoic 4,853.233 A 8/1989 McAskie acid are also disclosed, as well as methods for enhanc 4909,138 A 3/1990 McAskie ing ruminant fertility. 5,382,678 A 1/1995 Vinci et al. 5,391,787 A 2/1995 Vinci et al. 15 Claims, No Drawings US 6,774,252 B2 1 2 METHOD FOR MANUFACTURING FATTY the initial glyceride content of the fatty acid feed Stock is ACID CALCIUM SATS FROM HIGH above about 25 weight percent when using the process of GLYCERIDE CONTENT OLS U.S. Pat. No. 5,382,678. Hydrolyzing the glycerides to levels below 25 weight CROSS REFERENCE TO RELATED percent is not commercially feasible. Commercial omega-3 APPLICATION fatty acids in the free fatty acid form are So costly as to be commercially unfeasible. One can reduce the glyceride This application is a division of U.S. application Ser. No. content of the fish oil starting material by blending it with a 09/990,784, filed Nov. 14, 2001 now U.S. Pat. No. 6,576, low glyceride content fatty acid feedstock, Such as Palm 667 which is hereby incorporated by reference. Fatty Acid Distillate (PFAD), which has a glyceride content BACKGROUND OF THE INVENTION of about 15 to 20 weight percent. However, the quantity of PFAD that would have to be The present invention relates to a process for the produc added to fish oil to reduce the glyceride content to levels tion of rumen bypass feed Supplements. The proceSS con commercially feasible for use with the process of U.S. Pat. verts glyceride oils to their respective fatty acid calcium 15 No. 5,382,678 dilutes the concentration of desirable Salts. In particular, the present invention relates to a proceSS omega-3 fatty acid such as EPA and DHA to ineffective for the production of calcium Salts of unsaturated fatty acids levels. That is, the levels of DHA and EPA in the resulting derived from fish oil. The calcium salts of the present calcium Salt are So low that quantities of calcium Salt must invention, when fed to cattle, provide reproductive benefits, be added to the daily feed ration at levels above what is in particular, an increase in fertility as embodied in an considered acceptable by the dairy industry. increased rate of impregnation. The present invention there To be commercially viable, omega-3 fatty acid calcium fore also relates to methods for providing Such benefits in a salt feed supplements must have DHA and EPA concentra ruminant. tions high enough to confer the beneficial effects of these Dairy cows must be impregnated once a year to maintain omega-3 fatty acids when quantities of the calcium Salt are a lactation cycle in which milk is produced for ten months 25 added to feed ration at levels considered acceptable to the at a time with two month rest periods in between during cattle industry. Therefore, a need exists for a process by which the cow is dry. Given the gestation period of a dairy which calcium Salts may be prepared from fish oils having cow, the objective is to impregnate the cow within 83 days high concentrations of omega-3 fatty acid with the calcium after calving. The efficient management of a dairy herd thus Salts produced with reduced levels of unreacted glycerides in requires that the cows be maintained at the peak of fertility a free-flowing and Stable form easily handled by customers. to ensure re-impregnation within 83 dayS. Accordingly, there exists a need for nutritional Supple SUMMARY OF THE INVENTION ments that promote dairy cow fertility. Fish oil fatty acids This need is met by the present invention. It has now been have become the focus of numerous research programs that discovered that fatty acid calcium Salts having acceptable Seek to capitalize on their nutritional and physiological 35 levels of residual glycerides can be prepared from high properties. WO99/66877 discloses the use of omega-3 fatty glyceride content Starting materials by using elevated levels acids of fish oil origin to increase fertility in animals of calcium oxide, making it possible to prepare fatty acid including cattle. Among the omega-3 fatty acids disclosed calcium Salts from feedstockS containing levels of fish oil are eicosapentaenoic acid (EPA) and decosahexaenoic acid effective to provide useful concentrations of omega-3 fatty (DHA). 40 acids in the finished product. Unsaturated fatty acids, however, undergo hydrogenation Therefore, according to one aspect of the present to Saturated fatty acids by microbial action in the rumen and invention, a method is provided for the preparation of fatty must be fed to ruminants in a protected form. The most acid calcium Salts, which includes the Steps of providing a familiar form in which fatty acids in general are protected 45 fatty acid feedstock having a glyceride content between from microbial action in the rumen are the fatty acid calcium about 30 and about 60% by weight; adding to the feedstock salts disclosed by U.S. Pat. Nos. 4,642,317; 4,826,694, from about 2 to about 3 equivalents of calcium oxide relative 4,853,233; 4.853,233 and 4,909,138. This form of fatty acid to the feedstock, So that a reactive admixture is formed; and protection is widely accepted in the dairy industry. adding to the reactive admixture from about 2 to about 5 Fish oils have a glyceride content of 100%. That is, all of 50 equivalents of water relative to the calcium oxide, So that the the fatty acids in fish oils are in the glyceride form. Fatty calcium oxide hydrates and neutralizes the fatty acids to acid glycerides do not readily react to form calcium Salts form calcium Salts. using the processes disclosed by the above-listed patents. The method of the present invention thus includes the use For a product to be commercially feasible, glyceride levels of feedstocks derived from fish oils diluted to glyceride below about 5 weight percent are desirable to produce a 55 contents between about 30 and about 60 weight percent with free-flowing and Stable product. low glyceride content fatty acid feedstocks, such as PFAD. U.S. Pat. No. 5,382,678 discloses a process that report Other Suitable Sources of low glyceride content fatty acids edly can be used to prepare fatty acid calcium Salts from include fatty acids from Soy, cottonseed, corn and other feedstocks having glyceride contents as high as 40 weight vegetable fatty acid distillates, tallow, yellow grease or other percent, with the resulting product having a residual glyc 60 animal or fish derived free fatty acid Sources produced by eride content of less than about 5 weight percent. Products deodorization, refining, hydrolyzation or other processes with residual glyceride contents above 5 weight percent lack common in the fats and oil industry. Storage Stability, and are Susceptible to oxidation, post Thus, the method of the present invention obtains fatty heating, melting, Subsequent product Solidification, and a acid calcium Salts having useful concentration of omega-3 tendency to form lumpS upon Storage. Under industrial 65 fatty acids and acceptable levels of residual glycerides that conditions, however, it has not been possible to consistently heretofore could not be obtained on a commercial Scale obtain residual glyceride levels below 5 weight percent once using prior art manufacturing techniques.
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