Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Reexamination Certificate
2000-12-07
2004-02-03
Carr, Deborah D. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
C554S195000, C554S206000
Reexamination Certificate
active
06686487
ABSTRACT:
STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT
Not Applicable.
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates generally to triacylglycerol oligomer products and methods of making, using and producing same.
2. Description of the Related Art
Triacylglycerols(TAGS) are lipids of plant or animal origin. They include such common substances as safflower oil, canola oil, peanut oil, corn oil, cottonseed oil, sunflowerseed oil, linseed oil, soybean oil, tung oil, etc. Those TAGS that are liquids at room temperature are generally known as oils; those that are solids are usually known as fats. TAGS are simply the fatty acid esters of the triol glycerol. The general structure of TAGS is:
The fatty acids, R1, R2, R3, that are obtained by hydrolysis of naturally occurring fats and oils are long, straight-chain carboxylic acids with about 12 to 20 carbon atoms. Most fatty acids contain even number of carbon atoms. Some of these common fatty acids are saturated, while others have one or more elements of unsaturation; generally carbon—carbon double bonds.
TAGS naturally occur in some plants and can be obtained in relative pure forms by various processing methods. Substances such as free fatty acids and phospholipids are removed during processing. TAGS resulting from a single plant source after processing is a mixture made up of TAGS with differing percentages of saturated and unsaturated fatty acids. Table 1 lists the approximate composition of the fatty acids obtained from hydrolysis of some TAGS.
TABLE 1
Fatty Acid Composition Obtained by Hydrolyhsis of Common Triacylglycerols*
ELEO-
TAG
MYRISTIC
PALMITIC
STEARIC
OLEIC
LINOLEIC
STEARIC
LINOLENIC
SOYBEAN
1-2
6-10
2-4
20-30
50-58
5-10
COTTON
1-2
18-25
1-2
17-38
45-55
SEED
CORN
1-2
7-11
3-4
25-35
50-60
LINSEED
4-7
2-4
14-30
14-25
45-60
SUNFLOWER
6-7
1-2
21-22
66-67
TUNG
80
TABLE 2
list the supply of major TAGS produced in the United States.
TRIACYLGLYCEROL
PRODUCTION (POUNDS)
SOYBEAN
20,220,000,000
COTTONSEED
1,210,000,000
SUNFLOWERSEED
1,196,772,000
CORN
1,283,200,000
TAGS containing multiple double bonds within their carboxylic acid moieties will undergo thermal polymerization to form oligomers which are low molecular weight polymers. Triacylglycerol Oligomers(TAGOS) were first described by Schieber (1928).
Several investigators, Schieber (1928, 1929), Kappelmier (1933, 1938), Kurz (1936), Bradley (1940), Phalnikar and Bhide (1944), Bradley (1947), Barker, Crawford, and Hilditch (1951), Wisenblatt, Wells, and Common (1953), Wells and Common (1953), Pascual and Detera (1966), Boelhouwer, Knegiel, and Tels (1967), Saha and Bandyopadhyay (1974), Sarma (1984)) have suggested mechanisms for thermal polymerization of vegetable oils. Scheiber (1928, 1929) and Kappelmeier (1933, 1938) proposed a Diels-Alder diene synthesis as a basis for explaining the polymerization of vegetable oils which is often referred to in the literature. Most investigators agree with the formation of hydroxy unsaturated dimeric acids during thermal polymerization which are connected by means of a cyclic compound.
SUMMARY OF THE INVENTION
In one embodiment, the present invention is a method for degumming triacylglycerols. This method includes the steps of: (A) providing a degummer assembly including a tank member haveing an inlet and an outlet, and an interior reaction chamber. The inlet and the outlet are in open fluid communication with the interior reaction chamber. Step B introduces a triacylglycerol mixture into the interior reaction chamber of the degummer assembly via the inlet. Step C introduces a liquid medium at a predetermined temperature into the triacylglycerol mixture in the interior reaction chamber of the tank member, thereby causing at least two reaction products to form. Step D separates at least two reaction products resulting from the triacylglycerol mixture and the liquid medium. Step E removes at least two reaction products from the interior reaction chamber of the tank member via the outlet in the tank member.
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De Greyt, Kellens, and Huyghebaert, “Polymeric and oxidized triglyceride content of crude and refined vegetable oils”, Fett/Lipid (1997), 99(8): 287-90.
Dijkstra and Van Opstal, “The Total Degumming Process,” J.Am. Oil Chem. Soc. 66(7): 1002-1009 (Jul. 1989).
Diosady, L.L. “Scale-up of Canola Oil Degumming.” Journal of American Oil Chemists Society, 61, Aug. 1984: No. 8.
Huang, Vegetable Oil-Based News Printing Ink Developed by continuous Polymerization Reaction, School of Chemical Engineering, Oklahoma State University, Stillwater, OK, May 1994.
Morrison and Boyd, Organic Chemistry, 5thEd., p. 1271.
Dunlap Codding & Rogers
Franks Research Labs, Inc.
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