WO2007148889A1 - Edible plant oils from which saturated fatty acids were removed and manufacturing process thereof - Google Patents
Edible plant oils from which saturated fatty acids were removed and manufacturing process thereof Download PDFInfo
- Publication number
- WO2007148889A1 WO2007148889A1 PCT/KR2007/002865 KR2007002865W WO2007148889A1 WO 2007148889 A1 WO2007148889 A1 WO 2007148889A1 KR 2007002865 W KR2007002865 W KR 2007002865W WO 2007148889 A1 WO2007148889 A1 WO 2007148889A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- fatty acids
- saturated fatty
- edible plant
- plant oils
- Prior art date
Links
- 150000004671 saturated fatty acids Chemical class 0.000 title claims abstract description 88
- 235000003441 saturated fatty acids Nutrition 0.000 title claims abstract description 85
- 239000010773 plant oil Substances 0.000 title claims abstract description 42
- 235000018927 edible plant Nutrition 0.000 title claims abstract description 41
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 64
- 239000003921 oil Substances 0.000 claims abstract description 62
- 235000019198 oils Nutrition 0.000 claims abstract description 62
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000000194 fatty acid Substances 0.000 claims abstract description 41
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 40
- 229930195729 fatty acid Natural products 0.000 claims abstract description 40
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 40
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 32
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 30
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 30
- 239000004202 carbamide Substances 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 19
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 18
- 230000003197 catalytic effect Effects 0.000 claims abstract description 12
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 12
- 239000000944 linseed oil Substances 0.000 claims abstract description 9
- 235000021388 linseed oil Nutrition 0.000 claims abstract description 9
- 235000005687 corn oil Nutrition 0.000 claims abstract description 8
- 239000002285 corn oil Substances 0.000 claims abstract description 8
- 235000019482 Palm oil Nutrition 0.000 claims abstract description 7
- 150000004703 alkoxides Chemical class 0.000 claims abstract description 7
- 239000002540 palm oil Substances 0.000 claims abstract description 7
- 235000019489 Almond oil Nutrition 0.000 claims abstract description 6
- 240000008574 Capsicum frutescens Species 0.000 claims abstract description 6
- 235000002568 Capsicum frutescens Nutrition 0.000 claims abstract description 6
- 235000019487 Hazelnut oil Nutrition 0.000 claims abstract description 6
- 235000004347 Perilla Nutrition 0.000 claims abstract description 6
- 244000124853 Perilla frutescens Species 0.000 claims abstract description 6
- 235000019496 Pine nut oil Nutrition 0.000 claims abstract description 6
- 235000019484 Rapeseed oil Nutrition 0.000 claims abstract description 6
- 235000019774 Rice Bran oil Nutrition 0.000 claims abstract description 6
- 235000019485 Safflower oil Nutrition 0.000 claims abstract description 6
- 235000019486 Sunflower oil Nutrition 0.000 claims abstract description 6
- 239000008168 almond oil Substances 0.000 claims abstract description 6
- 239000010495 camellia oil Substances 0.000 claims abstract description 6
- 238000010668 complexation reaction Methods 0.000 claims abstract description 6
- 235000008524 evening primrose extract Nutrition 0.000 claims abstract description 6
- 239000010475 evening primrose oil Substances 0.000 claims abstract description 6
- 229940089020 evening primrose oil Drugs 0.000 claims abstract description 6
- 239000008169 grapeseed oil Substances 0.000 claims abstract description 6
- 239000010468 hazelnut oil Substances 0.000 claims abstract description 6
- 239000004006 olive oil Substances 0.000 claims abstract description 6
- 235000008390 olive oil Nutrition 0.000 claims abstract description 6
- 239000010490 pine nut oil Substances 0.000 claims abstract description 6
- 239000008165 rice bran oil Substances 0.000 claims abstract description 6
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- 239000003813 safflower oil Substances 0.000 claims abstract description 6
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- 239000002385 cottonseed oil Substances 0.000 claims abstract description 5
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- 239000010466 nut oil Substances 0.000 claims abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 37
- 230000008030 elimination Effects 0.000 claims description 34
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- 238000002360 preparation method Methods 0.000 claims description 2
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- OLEWRQVKIUHEJP-UHFFFAOYSA-N methyl 3-hydroxy-2-phenylpropanoate Chemical compound COC(=O)C(CO)C1=CC=CC=C1 OLEWRQVKIUHEJP-UHFFFAOYSA-N 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- MAYCICSNZYXLHB-UHFFFAOYSA-N tricaproin Chemical compound CCCCCC(=O)OCC(OC(=O)CCCCC)COC(=O)CCCCC MAYCICSNZYXLHB-UHFFFAOYSA-N 0.000 claims 1
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- PJHKBYALYHRYSK-UHFFFAOYSA-N triheptanoin Chemical compound CCCCCCC(=O)OCC(OC(=O)CCCCCC)COC(=O)CCCCCC PJHKBYALYHRYSK-UHFFFAOYSA-N 0.000 claims 1
- 229940078561 triheptanoin Drugs 0.000 claims 1
- YZWRNSARCRTXDS-UHFFFAOYSA-N tripropionin Chemical compound CCC(=O)OCC(OC(=O)CC)COC(=O)CC YZWRNSARCRTXDS-UHFFFAOYSA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
- C11B7/0025—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents containing oxygen in their molecule
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
- C11B7/0033—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents containing other heteroatoms in their molecule
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/08—Refining
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
Definitions
- the present invention is concerned with edible- plant oils from which saturated fatty acids were removed and a manufacturing process thereof.
- saturated and unsaturated fatty acids are bound in a mixed state on same triglyceride molecules, since they are randomly distributed in the triglyceride molecules. In other words, it will have rare possibilities of the presence of triglycerides composed of only one kind of saturated fatty acids as tripalmitin or tristearin in case when the content of saturated fatty acids in the oil are relatively low as the cases of edible plant oils. Therefore the conventional physical processes as low temperature fractional crystallization are not applicable for the elimination of saturated fatty acids from edible plant oils.
- the present invention differs from our previous invention in respect to the facts that 1) the saponification reaction in our former invention is replaced by the transesterification in the present invention to produce the mixture of alkylesters of fatty acids instead of the mixture of free fatty acids, 2) urea complexation of fatty acids is replaced by urea complexation of fatty acid-alkylester and 3) reconstruction of triglyceride via fatty-acyl-chloride activation through the reaction with oxalyl chloride is replaced by interesterification reaction of alkylesters of unsaturated fatty acids with triacetin under alkali metal or alkali-earth metal-C ⁇ C alkoxide catalyst.
- This new invention is easier and more convenient in the
- the most cost effective step of the present process is the transesterification step where the use of excessive amount of absolutely anhydrous C ⁇ C alkanol is obligatory. At the end of transesterification reaction, the neutralization of alkali-metal or alkali-earth metal C ⁇ C alkoxide to
- the three step chemical treatments for the edible oil to produce the invented product are not employing any chemical changes as oxidation or reduction on chemical entities of the edible oils except the partner change of ester bond and should not give any chemical remainings behind. More important things are that the taste and flavor of the invented product should be acceptable for human consumption and also that the chemical reactions for the invented production process should not alter the chemical entities of oil except for the elimination of saturated fatty acids and that no chemical residues should be remained after the necessary chemical treatments.
- the present invention concerned with the preparation of edible plant oils devoid of saturated fatty acids, consists of following three steps of conventional chemical processes: [15] 1) In the first step(step-A;transesterification), edible plant oil is treated to produce alkyl-esters of fatty acids by stirring with large excess of anhydrous C ⁇ C alkanol,
- alkali- or alkali-earth metal-C ⁇ C alkoxide preferably 0.01-0.1 mol % of sodium or potassium ethoxide
- the catalytic activity of sodium or potassium alkoxide is destroyed by the addition of equivalent amount of organic or inorganic acid at the end of transesterification reaction and then removed the absolute alkanol by distillation to obtain the mixture of alkyl-esters of fatty acids.
- the neutralization of reaction mixture by glacial acetic acid instead of dilute mineral acids such as d-HCl or d-H SO ensures the recovery of absolute alkanol for next uses by which the production cost will be highly reduced.
- step-B the mixture of alkyl-esters of fatty acids was treated with ethanol solution of urea in order to eliminate the urea complex of saturated fatty acid-alkylester as crystal.
- unsaturated fatty acid-alkylester could be obtained from the filtrate by conventional after-treatment as acidification, partition to organic solvent and followed by concentration.
- step-C the reconstruction of edible plant oil by triglyceride bond formation was accomplished by interesterification reaction in which the three molar alkylester of unsaturated fatty acids were mixed with one mole triglycerides of C ⁇ C fatty acid selected from the list of C ⁇ C -fatty acids (preferably triacetin) together with catalytic amount of alkali- or alkali earth metal-alkoxide and heated in an oil-bath(95 ⁇ 175°C) under reduced pressure until the distillation of ethylacetate is ceased.
- the reaction mixture is neutralized by d-HCl or d-H 2 SO 4 , extracted with hexane and concentrated to obtain final product of this invention.
- the present invention is illustrated in detail with the following examples and experiments,
- the list of edible plant oils tested for the applicability of present invention is as followings; 1) corn oil, 2)bean oil, 3) rapeseed oil, 4) grape seed oil, 5) flaxseed oil, 6) sesame oil, 7) olive oil, 8) perilla oil 9) wall nut oil, 10) pine-nut oil, 11) peanuts oil, 12) sunflower oil, 13) safflower oil, 14) cotton seed oil, 15) palm oil, 16) hot pepper oil, 17) rice bran oil, 18) pumpkin oil, 19) green tea seed oil, 20) almond oil, 21) evening primrose oil and 22) Hazelnut oil.
- the alkanol in the present invention denotes one of primary or secondary alkanol selected from C ⁇ C alkanol.
- Experiment 1-7 Elimination of saturated fatty acids from olive oil [42] A portion of olive oil(50.09 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 29.60 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. This sample needed increased amount of sodium-alkoxide and glacial acetic acid respectively 350 and 100 D for both transester- ification and interesterification reaction. The fatty acid composition of reconstructed triglyceride olive oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1.
- fatty acids were completely removed by the present invention is very useful as edible plant oil for human beings.
Abstract
The present invention is concerned with an edible plant oils from which saturated fatty acids were removed and manufacturing process thereof. In order to remove saturated fatty acids from the edible plant oils; 1) Saturated and unsaturated fatty acids bound on same triglyceride molecules of edible plant oils were segregated each other as alkylestes of fatty acids by conventional transesterification reaction in which edible plant oils were treated with large excess of absolute C1 ~C8 alkanol under the presence of catalytic amount of alkali- or alkali-earth metal-C ~C o alkoxide. 2) The alkyl-esters of mixed fatty acids were treated with C1 ~C8 alkanol solution of urea to remove the alkylester of saturated fatty acids by conventional fractional crystallization as urea complexes of saturated fatty acid- alky lesters. 3) Finally the resulting alkylesters of unsaturated fatty acids, obtained by removal of saturated fatty acids by urea complexation procedure, was converted to reconstructed triglyceride oil to give edible plant oils completely devoid of saturated fatty acids. This new manufacturing process could be successfully applied to following 22 kinds of edible plant; 1) corn oil, 2)soybean oil, 3) rapeseed oil, 4) grape seed oil, 5) flaxseed oil, 6) sesame oil, 7) olive oil, 8) perilla oil 9) wall nut oil, 10) pine-nut oil, 11) peanuts oil, 12) sunflower oil, 13) safflower oil, 14) cotton seed oil, 15) palm oil, 16) hot pepper oil, 17) rice bran oil, 18) pumpkin oil, 19) green tea seed oil, 20) almond oil, 21) evening primrose oil and 22) hazelnut oil.
Description
Description
EDIBLE PLANT OILS FROM WHICH SATURATED FATTY ACIDS WERE REMOVED AND MANUFACTURING PROCESS
[ THEREOF ]
Technical Field It is well known facts that saturated fatty acids in the lipid-rich food especially from warm blooded animals will have risk to elicite various cardio-vascular diseases It is also well known facts that plant oils bad been used as edible oils without any further processing due to the relatively low content of saturated fatty acids and that warm blooded animal fats are less frequently used for the food processing, ϊt is well known fact that the polyunsaturated fatty acids(PUFA) in our diet reduce the bloσd level of cholesterol including neutral lipid level and further that saturated fatty acids are- antagonizing the beneficial activity of PUFA by elevating both parameter with twice potency compared to the loweririg activity of PMFA. fϊfenee it is necessary to establish a new method to remove- saturated fatty acids from edible plant oils.
Background Art The present invention is concerned with edible- plant oils from which saturated fatty acids were removed and a manufacturing process thereof. We can find an equimolar mixture of triolein and trilinolein listed in Sigma- Aldrich
Reagent Catalogue. This mixture of triglycerides composed of two unsaturated fatty acids, i.e., oleic acid and linoleie acid must be prepared by mixing two synthetically obtained triglycerides, i.e. triolein and trilinolien in-order to use as reference standards, for the retention time in the HPLC analysis of triglycerides and not prepared by elimination of saturated fatty acids from edible plant oik. Our previous invention on flaxseed oil (Korean patent Na. 10-0663063, date; 2004
1222) was also concerned with the elimination of saturated fatty acids together with two other toxic components in the oil and it/was also composed of three steps i.e., 1) saponification, 2) urea complexatiort and 3) reconstruction of triglyceride, via conventional condensing process of fatty-acyl chloride with glycerine. The present invention differs from our previous invention in respect to the facts that 1) saponification in our previous invention is replaced by transesterification and 2) recon- straction of triglceride via acyl-halide process is replaced by interesterification of al-
Technical Problem
[7] Generally, saturated and unsaturated fatty acids are bound in a mixed state on same triglyceride molecules, since they are randomly distributed in the triglyceride molecules. In other words, it will have rare possibilities of the presence of triglycerides composed of only one kind of saturated fatty acids as tripalmitin or tristearin in case when the content of saturated fatty acids in the oil are relatively low as the cases of edible plant oils. Therefore the conventional physical processes as low temperature fractional crystallization are not applicable for the elimination of saturated fatty acids from edible plant oils.
[8]
Technical Solution
[9] In order to remove saturated fatty acids from plant oil, following three conventional organic reactions are combined to establish a new simple and economic procedure; 1) saturated and unsaturated fatty acids bound to same triglyceride molecules should be segregated each other by transesterification reaction producing the mixture of alkyl- esters of saturated and unsaturated fatty acids, 2) the resulting alkyl-esters of saturated fatty acids are completely removed by fractional crystallization of urea complex of fatty acid-alkylesters and 3) reconstruction of triglyceride oil by interesterification reaction of alkyl-ester of unsaturated fatty acids with triacetin. The above three reactions; ie, transesterification, urea complexation of fatty acids and interesterification are all conventional processes in the lipid chemistry, however, these three conventional chemical processes had never been combined to remove saturated fatty acid from edible plant oils. In the previous references(US-patent No.05434278) of the interesterification reaction, it was conventionally applied for the mixture of triglycerides of long chain fatty acid and shorter chain fatty acids for the randomization of fatty-acid distribution in the triglyceride molecules in order to modify such physical properties as melting point of fat, but not for the reconstruction of triglycerides starting from unsaturated fatty acid-alkylesters for the purpose of complete elimination of saturated fatty acids from edible plant oils.
[10] The present invention differs from our previous invention in respect to the facts that
1) saponification in our previous invention is replaced by transesterification and 2) reconstruction of triglceride via acyl-halide process is replaced by interesterification of alkylester of unsaturated fatty acids with triacetin. This new invention is easier and more convenient in the reaction processes and also more economic to produce edible plant oils in which saturated fatty acids are completely removed.
[H]
Mode for the Invention
[12] Our previous invention on flaxseed oil(Korean patent No. 10-0663063, date; 2006,
12 22), was also concerned with the elimination of saturated fatty acids together with two other toxic components in the oil and it was also composed of three steps i.e., 1) saponfication, 2) urea complexation and 3) reconstruction of triglyceride via conventional condensing process of fatty-acyl chloride with glycerine. For the edible plant oils it has no need to eliminate or destroy any toxic components, hence it is necessary to establish some more convenient and economic procedure for the elimination of saturated fatty acids.
[13] When we compare the processes of two inventions, i.e., the former invention for flax seed oil and the present invention for edible plant oils, the present invention differs from our previous invention in respect to the facts that 1) the saponification reaction in our former invention is replaced by the transesterification in the present invention to produce the mixture of alkylesters of fatty acids instead of the mixture of free fatty acids, 2) urea complexation of fatty acids is replaced by urea complexation of fatty acid-alkylester and 3) reconstruction of triglyceride via fatty-acyl-chloride activation through the reaction with oxalyl chloride is replaced by interesterification reaction of alkylesters of unsaturated fatty acids with triacetin under alkali metal or alkali-earth metal-C ~C alkoxide catalyst. This new invention is easier and more convenient in the
1 8 reaction processes and also more economic to produce edible plant oils in which saturated fatty acids are completely removed. The market price of edible plant oil is very cheap and the quantity of consumption must be very great, hence simpler process for the production of the invented product would be better and the production cost of invented product should be as low as possible. The most cost effective step of the present process is the transesterification step where the use of excessive amount of absolutely anhydrous C ~C alkanol is obligatory. At the end of transesterification reaction, the neutralization of alkali-metal or alkali-earth metal C ~C alkoxide to
1 8 destroy its catalytic activity by glacial acetic acid instead of dilute mineral acid enables us to recover absolute alkanol without any compositional changes. This simple modification will be cost reducing process, since the recovered absolute alkanol will be recycled for same purpose. The three step chemical treatments for the edible oil to produce the invented product are not employing any chemical changes as oxidation or reduction on chemical entities of the edible oils except the partner change of ester bond and should not give any chemical remainings behind. More important things are that the taste and flavor of the invented product should be acceptable for human consumption and also that the chemical reactions for the invented production process should not alter the chemical entities of oil except for the elimination of saturated fatty acids and that no chemical residues should be remained after the necessary chemical treatments. All chemical reagent including urea and triacetin used in this invention
may be acceptable as the chemical reagent for the food processing, since these are found in GRAS-list of U.S.-FDA(Generally Recognized As Safe for Food). [14] The present invention, concerned with the preparation of edible plant oils devoid of saturated fatty acids, consists of following three steps of conventional chemical processes: [15] 1) In the first step(step-A;transesterification), edible plant oil is treated to produce alkyl-esters of fatty acids by stirring with large excess of anhydrous C ~C alkanol,
1 8 preferably ethanol), and catalytic amount of alkali- or alkali-earth metal-C ~C alkoxide (preferably 0.01-0.1 mol % of sodium or potassium ethoxide) until the interfaces of oil in alkanol will be disappeared. The catalytic activity of sodium or potassium alkoxide is destroyed by the addition of equivalent amount of organic or inorganic acid at the end of transesterification reaction and then removed the absolute alkanol by distillation to obtain the mixture of alkyl-esters of fatty acids. The neutralization of reaction mixture by glacial acetic acid instead of dilute mineral acids such as d-HCl or d-H SO ensures the recovery of absolute alkanol for next uses by which the production cost will be highly reduced.
[16] 2) In the second step(step-B), the mixture of alkyl-esters of fatty acids was treated with ethanol solution of urea in order to eliminate the urea complex of saturated fatty acid-alkylester as crystal. After removal of crystalline urea complex of saturated fatty acid-alkylesters by filtration, unsaturated fatty acid-alkylester could be obtained from the filtrate by conventional after-treatment as acidification, partition to organic solvent and followed by concentration.
[17] 3) In the final step of this invention(step-C), the reconstruction of edible plant oil by triglyceride bond formation was accomplished by interesterification reaction in which the three molar alkylester of unsaturated fatty acids were mixed with one mole triglycerides of C ~C fatty acid selected from the list of C ~C -fatty acids (preferably triacetin) together with catalytic amount of alkali- or alkali earth metal-alkoxide and heated in an oil-bath(95~175°C) under reduced pressure until the distillation of ethylacetate is ceased. The reaction mixture is neutralized by d-HCl or d-H 2 SO 4 , extracted with hexane and concentrated to obtain final product of this invention.
[18] In order to confirm the correct reconstruction of edible triglyceride oil, the fatty acid composition of the final invented product was analyzed by GLC, and also confirmed the disappearance of alkyl proton peaks in the proton NMR. The proton-NMR peaks of invented product were reasonably assigned to the mixture of unsaturated fatty acids and alkoxy protons of glycerol moiety of reconstructed triglyceride oil.
[19] The present invention is illustrated in detail with the following examples and experiments, The list of edible plant oils tested for the applicability of present invention is as followings; 1) corn oil, 2)bean oil, 3) rapeseed oil, 4) grape seed oil, 5) flaxseed
oil, 6) sesame oil, 7) olive oil, 8) perilla oil 9) wall nut oil, 10) pine-nut oil, 11) peanuts oil, 12) sunflower oil, 13) safflower oil, 14) cotton seed oil, 15) palm oil, 16) hot pepper oil, 17) rice bran oil, 18) pumpkin oil, 19) green tea seed oil, 20) almond oil, 21) evening primrose oil and 22) Hazelnut oil. However, these examples do not limit the scope of the present invention. The alkanol in the present invention denotes one of primary or secondary alkanol selected from C ~C alkanol.
[20]
[21] Experiment 1
[22]
[23] Experiment 1-1 : Elimination of saturated fatty acids from corn oil
[24] The reaction mixture of 50.34 g corn oil, completely dehydrated in advance by heating in 1050C silicon oil-bath under reduced pressure, 250 D absolute ethanol and catalytic amount(250 D) of 28%-sodium-methoxide solution was mixed well by magnetic stirring for 5 hours at room temperature until the homogenous solution was obtained due to the progress of transesterification reaction. The catalytic acitivity of sodium methoxide in the reaction mixture was destroyed by the addition of 70 D glacial acetic acid. To the reaction mixture 80 g urea and 250 D ethanol was added and heated in a water-bath until the urea is completely dissolved and stored overnight at room temperature to crystallize urea complex of saturated fatty acids-methyl ester. The crystalline urea complexes were filtered off by suction. The filtrate was concentrated to obtain amorphous urea complex of unsaturated fatty acid-methyl ester and to recover absolute ethanol for the next recycling. The acidification of amorphous urea complex with d-HCl followed by hexane extraction and concentration gave 32.64 g methyl ester of unsaturated fatty acids. When the fatty acid composition of corn oil was assayed by GLC before and after the elimination of saturated fatty acids as shown in Table- 1, saturated fatty acids of corn oil were completely eliminated together with a part of oleic acid, hence the content of linoleic acid was rather increased from 48.1% to 76.43%. In order to synthetize reconstructed triglyceride oil by interesterification reaction, 8 g of triacetin and 250 D of 28% sodium-methoxide solution were added to the above methylester of unsaturated fatty acid and heated to 95~125°C in a silicone oil bath under reduced pressure (< 50 mmHg) to remove ethyl-acetate produced by the interesterification. After the cease of ethyl-acetate gas evolvement, the reaction mixture was neutralized with 70 D glacial acetic acid and diluted with water. The resulting triglyceride oil was extracted with hexane and finally concentrated to give 32.60 g triglyceride corn oil composed of only unsaturated fatty acids.
[25]
[26] Experiment 1-2 : Elimination of saturated fatty acids from soybean oil
[27] A portion of soybean oil(50.34 g) was treated by the same experimental procedures
as described in Experiment 1-1 to give 31.34 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. The fatty acid composition of reconstructed triglyceride soybean oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1.
[28]
[29] Experiment 1-3 : Elimination of saturated fatty acids from rapeseed oil]
[30] A portion of rapeseed oil(50.91 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 42.62 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. The fatty acid composition of reconstructed triglyceride rapeseed oil was analyzed by GLC as described in [Experiment 2] 1 and the data are tabulated in Table- 1.
[31]
[32] Experiment 1-4 : Elimination of saturated fatty acids from grapeseed oil
[33] A portion of grapeseed oil(50.21 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 38.04 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. The fatty acid composition of reconstructed triglyceride grapeseed oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1.
[34]
[35] Experiment 1-5 : Elimination of saturated fatty acids from flaxseed oil
[36] A portion of flaxseed oil(49.86 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 42.10 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. However, this sample needed increased amount of sodium- alkoxide and glacial acetic acid respectively 320 and 90 D for both transesterification and interesterification reaction. The fatty acid composition of reconstructed triglyceride flaxseed oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1.
[37]
[38] Experiment 1-6 : Elimination of saturated fatty acids from sesame seed oil
[39] A portion of sesame seed oil(50.71 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 43.02 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. This sample, however, needed increased amount of sodium-alkoxide and glacial acetic acid respectively 850 and 240 D for both transesterification and interesterification reaction. The fatty acid composition of reconstructed triglyceride sesame oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1.
[40]
[41] Experiment 1-7 : Elimination of saturated fatty acids from olive oil
[42] A portion of olive oil(50.09 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 29.60 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. This sample needed increased amount of sodium-alkoxide and glacial acetic acid respectively 350 and 100 D for both transester- ification and interesterification reaction. The fatty acid composition of reconstructed triglyceride olive oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1.
[43]
[44] Experiment 1-8 : Elimination of saturated fatty acids from perilla oil
[45] A portion of perilla oil(50.33 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 41.35 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. This sample needed increased amount of sodium-alkoxide and glacial acetic acid respectively 400 and 110 D for both transester- ification and interesterification reaction. The fatty acid composition of reconstructed triglyceride perilla oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1.
[46]
[47] Experiment 1-9 : Elimination of saturated fatty acids from walnut oil
[48] A portion of walnut oil(50.06 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 29.86 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. This sample needed increased amount of sodium-alkoxide and glacial acetic acid respectively 400 and 110 D for both transester- ification and interesterification reaction. The fatty acid composition of reconstructed triglyceride walnut oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1.
[49]
[50] Experiment 1-10 : Elimination of saturated fatty acids from pine-nut oil
[51] A portion of pine-nut oil(50.34 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 39.28 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. This sample needed increased amount of sodium-alkoxide and glacial acetic acid respectively 300 and 80 D for both transester- ification and interesterification reaction. The fatty acid composition of reconstructed triglyceride pine-nut oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1.
[52]
[53] Experiment 1-11 : Elimination of saturated fatty acids from peanut oil
[54] A portion of peanut oil(50.29 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 27.22 g of reconstructed triglyceride oil which is
completely free of saturated fatty acids. This sample needed increased amount of sodium- alkoxide and glacial acetic acid respectively 400 and 110 D for both transester- ification and interesterification reaction. The fatty acid composition of reconstructed triglyceride peanut oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1. [55]
[56] Experiment 1-12 : Elimination of saturated fatty acids from sunflower oil
[57] A portion of sunflower oil(50.17 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 35.19 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. This sample needed increased amount of sodium- alkoxide and glacial acetic acid respectively 500 and 140 D for both transester- ification and interesterification reaction. The fatty acid composition of reconstructed triglyceride sunflower oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1. [58]
[59] Experiment 1-13 : Elimination of saturated fatty acids from safflower oil
[60] A portion of safflower oil(50.18 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 28.50 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. This sample needed increased amount of sodium- alkoxide and glacial acetic acid respectively 600 and 170 D for both transester- ification and interesterification reaction. The fatty acid composition of reconstructed triglyceride safflower oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1. [61]
[62] Experiment 1-14 : Elimination of saturated fatty acids from cotton seed oil
[63] A portion of cotton seed oil(50.01 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 25.11 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. This sample needed increased amount of sodium- alkoxide and glacial acetic acid respectively 200 and 50 D for both transesterification and interesterification reaction. The fatty acid composition of reconstructed triglyceride cotton oil was analyzed by GLC as described in [Experiment 2 ] and the data are tabulated in Table- 1. [64]
[65] Experiment 1-15 : Elimination of saturated fatty acids from palm oil
[66] The reaction mixture of 51.01 g palm oil, completely dehydrated in advance by heating in 1050C silicon oil-bath under reduced pressure, 250 D absolute ethanol and catalytic amount( 850 D) of 21%-sodium-ethoxide solution was mixed well by magnetic stirring for 5 hours at room temperature until the homogenous solution was obtained
due to the progress of transesterification reaction. The catalytic acitivity of sodium ethoxide in the reaction mixture was destroyed by the addition of 200 D glacial acetic acid. To the reaction mixture 260 g urea and 500 D ethanol was added and heated in a water-bath until the urea is completely dissolved and stored overnight at room temperature to crystallize urea complex of saturated fatty acids-ethyl ester. The crystalline urea complexes were filtered off by suction. The filtrate was concentrated to obtain amorphous urea complex of unsaturated fatty acid-ethylester and to recover absolute ethanol for the next recycling. The acidification of amorphous urea complex with d-HCl followed by hexane extraction and concentration gave 3.4 g ethylester. of unsaturated fatty acids. When the fatty acid composition of palm oil was assayed by GLC before and after the elimination of saturated fatty acids as shown in Table- 1, saturated fatty acids of palm oil were completely eliminated together with a part of oleic acid, hence the content of linoleic acid was rather increased from 10.40% to 66.88%. In order to synthetize reconstructed triglyceride oil by interesterification reaction, one gram of triacetin and 50 D of 21%- sodium-ethoxide solution were added to the above ethylester of unsaturated fatty acid and heated to 95~125°C in a silicone oil bath under reduced pressure (< 50 mmHg) to remove ethyl-acetate produced by the interesterification. After the cease of ethyl-acetate gas evolvement, the reaction mixture was neutralized with 15 D glacial acetic acid and diluted with water. The resulting triglyceride oil was extracted with hexane and finally concentrated to give 2.91 g triglyceride oil composed of only unsaturated fatty acids. [67]
[68] Experiment 1-16 : Elimination of saturated fatty acids from hot pepper oil
[69] A portion of hot pepper oil(50.03 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 28.56 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. This sample needed increased amount of sodium- alkoxide and glacial acetic acid respectively 400 and 110 D for both transesterification and interesterification reaction. The fatty acid composition of reconstructed triglyceride hot pepper oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1. [70]
[71] Experiment 1-17 : Elimination of saturated fatty acids from rice bran oil
[72] A portion of rice bran oil(50.28 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 29.26 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. This sample needed increased amount of sodium- alkoxide and glacial acetic acid respectively 400 and 110 D for both transesterification and interesterification reaction. The fatty acid composition of reconstructed triglyceride rice bran oil was analyzed by GLC as described in [Experiment 2] and the
10 WO 2007/148889 PCT/KR2007/002865
data are tabulated in Table- 1. [73] [74] Experiment 1-18 : Elimination of saturated fatty acids from pumpkin oil
[75] A portion of pumpkin seed oil(50.96 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 36.67 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. This sample, however, needed increased amount of sodium- alkoxide and glacial acetic acid respectively 300 and 80 D for both transesterification and interesterification reaction. The fatty acid composition of reconstructed triglyceride pumpkin seed oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1.
[76]
[77] Experiment 1-19 : Elimination of saturated fatty acids from green tea seed oil
[78] A portion of green tea seed oil(50.35 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 28.68 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. This sample needed increased amount of sodium- alkoxide and glacial acetic acid respectively 400 and 110 D for both transesterification and interesterification reaction. The fatty acid composition of reconstructed triglyceride green tea seed oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1.
[79]
[80] Experiment 1-20 : Elimination of saturated fatty acids from almond oil
[81] A portion of almond oil(50.75 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 41.78 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. This sample needed increased amount of sodium-alkoxide and glacial acetic acid respectively 200 and 50 D for both transesterification and interesterification reaction. The fatty acid composition of reconstructed triglyceride almond oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1.
[82]
[83] Experiment 1-21 : Elimination of saturated fatty acids from evening primrose oil(EPO)
[84] A portion of evening primrose oil(50.23 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 42.34 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. This sample, however, needed increased amount of sodium-alkoxide and glacial acetic acid respectively 300 and 80 D for both transesterification and interesterification reaction. The fatty acid composition of reconstructed triglyceride evening primrose oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1.
1 1 WO 2007/148889 PCT/KR2007/002865
[85]
[86] Experiment 1-22 : Elimination of saturated fatty acids from hazelnut oil
[87] A portion of hazelnut oil(50.48 g) was treated by the same experimental procedures as described in Experiment 1-1 to give 32.14 g of reconstructed triglyceride oil which is completely free of saturated fatty acids. This sample needed increased amount of sodium- alkoxide and glacial acetic acid respectively 400 and 110 D for both transester- ification and interesterification reaction. The fatty acid composition of reconstructed triglyceride hazelnut oil was analyzed by GLC as described in [Experiment 2] and the data are tabulated in Table- 1.
[88]
[89] All edible plant oils were treated by the same ways as described above in Experiment
1-1 except that the quantities of urea used to eliminate saturated fatty acids were appropriately modified depending on the total quantities of saturated fatty acid contents in the oils.
[90]
[91] Experiment 2
[92]
[93] Gaschromatographic analysis of fatty acid composition of oils
[94] Each twenty microliter of edible plant oils and their reconstructed triglyceride oil were mixed with 100 D of 28% sodium methoxide in MeOH and mixed well with 100 D hexane and centrifuged. for 10 minutes at 12000 rpm. Each five microliters hexane- layer was taken and diluted with 95 D hexane. Each ten microliters portion of diluted hexane layer was injected for the gas-chromatographic analysis. Gas-chromatograpic conditions; Hewlett-Packard 5890-11 Series(HP Co., Wilmington, DE, USA), detector; FID, coloumn; DB-23 capillary(60 m, 0.25 D ID, 0.25 D), temp; oven; initial 1300C, programmed 2.7°C/min. to final 2300C, injector; 2700C, carrier gas; nitrogen, flow rate; 30 D/min. The results of GLC-analysis for each untreated edible plant oil and each reconstructed triglyceride oils are tabulated in Table- 1.
[95] [PMR peak assignments for the reconstructed flaxseed triglyceride oil obtained by the elimination of saturated fatty acid]; The proton-NMR spectra of reconstructed flaxseed triglyceride oil was measured and assigned carefully for all proton peaks to the partial structure of composing fatty acids. Integration of every peak areas is correctly supporting the composition of unsaturated fatty acids in the oil. . NMR, 300 MHz(TMS, CDCl δ) ; 0.96(methyl, 9H, t, J = 7.5Hz), 1.296(aliphatic methylenes, 36-38H, br, s.), 1.497(carboxyl adjacent methylene, 6H, t, J = 7.5Hz), 2.046(olefine adjacent methylene, 12H, m), 2.302(=CHCHaHbCH=, 6H, m), 2.795(=CHCHaHb CH=, 6H, m), 4.136(glyceryl CHaHbO-,2H, m, J = 6.0Hz, 16Hz), 4.287(glyceryl CH3 13^0-,2H, m, J = 6.0Hz, 16Hz), 5.259(glyceryl CH2(O-)CH(O-)CH2(O-), 2H, m, / =
12
WO 2007/148889 PCT7KR2007/002865
6.0Hz, 16Hz), 5.35(olefinic, =CH-, 14-16H, m). The structural assignments of the above proton peaks are well accorded to the compositions(GLC-data) of unsaturated fatty acids of finally reconstructed triglyceride.
[96] [97] Table-1. Fatty acid composition of various edible plant oils before and after the elimination of saturated fatty acids(%, w/w); saturated fatty acid contents are the sum of stearic acid and palmitic acid
[98]
[99]
Industrial Applicability
[100] Edible plant oils reconstructed only by unsaturated fatty acids from which saturated
13 WO 2007/148889 PCT/KR2007/002865
fatty acids were completely removed by the present invention is very useful as edible plant oil for human beings.
Claims
[1] A method for preparing edible plant oils composed of unsaturated fatty acids devoid of saturated fatty acids, starting from ordinary edible plant oils by combination of following three steps of chemical reactions; Step-A (transesterification; preparation of alkyl-ester of fatty acids from edible plant oil); Edible plant oil is subjected to transesterification by mixing with excessive amount of anhydrous C ~C alkanol with catalytic amount of alkali- or alkali-earth metal C 1 ~C 8 alkoxide and stirred until the oil / alkanol interface are disappeared. At the end of the transesterification reaction, the reaction mixture is neutralized by the addition of equi-molar amount of C ~C organic acid or dilute mineral acid to destroy catalytic activity of alkoxide. Anhydrous alkanol may be recovered for recycling by distillation of neutralized reaction mixture and the remaining residue is extracted with organic solvent to obtain the mixture of alkylesters of saturated and unsaturated fatty acids by conventional after treatment.
Step-B(urea complexation of fatty acid-alkyl ester); The alkylester of fatty acids, obtained by step-A, are heated with C ~C alkanol solution of urea to form the
1 8 urea-fatty acid- alkylester and then to eliminate the crystalline complex of urea- saturated fatty acid- alkylester complex by filtration. The alkylester of unsaturated fatty acids are obtained by the such conventional after-treatment on the filtrate as acidification, extraction by organic solvent and concentration. Step-C(interesterification); The three molar amount of anhydrous alkylester of unsaturated fatty acids, obtained from step-B, are mixed with equi-molar amount of C ~C fatty acyl-triglyceride selected among C ~C -fatty acyl-triglycerides
I o I o together with catalytic amount of alkali- or alkali-earth metal C ~C alkoxide and b J 1 8 treated the reaction mixture to remove the fatty acyl(C ~C )-alkylester produced
1 8 by the interesterification. After the end of interesterification, the reaction mixture is neutralized and extracted with organic solvent, followed by concentration to give final product, edible reconstructed plant oils composed of unsaturated fatty acids only.
[2] A method for preparing edible plant oils composed of unsaturated fatty acids devoid of saturated fatty acids according to claim 1 wherein edible plant oils is selected from the group composed of 1) Corn oil, 2) Soybean oil,
3) Rapeseed oil, 4) Grape seed oil, 5) Flaxseed oil, 6) Sesame oil, 7) Olive oil, 8) Perilla oil, 9) Wall nut oil, 10) Pine-nut oil, 11) Peanut oil, 12) Sunflower oil, 13) Safflower oil, 14) Cotton seed oil, 15) Palm oil, 16) Hot pepper oil, 17) Rice bran oil, 18) Pumpkin oil, 19) Tea seed oil 20) Almond oil 21) Evening primrose oil(EPO),
15 WO 2007/148889 PCT/KR2007/002865
22) Hazelnut oil. [3] A method for preparing edible plant oils composed of unsaturated fatty acids devoid of saturated fatty acids according to claim 1 wherein alkali-or alkali-earth metal-C 1 ~C 8 alcoxide in step A or step C is selected from the group composed of sodium alkoxide, lithium alkoxide, potassium alkoxide, magnesium alkoxide and calcium alkoxide.
[4] A method for preparing edible plant oils composed of unsaturated fatty acids devoid of saturated fatty acids according to claim 1 wherein organic or inorganic acid in step-A is selected from the group composed of formic acid, acetic acid, propionic acid, butyric acid, hydrochloric acid, sulfuric acid, phosphoric acid and nitric acid.
[5] A method for preparing edible plant oils composed of unsaturated fatty acids devoid of saturated fatty acids according to claim 1 wherein C ~C fatty-acyl griglyceride in step C in claim 1 is selected from the group composed of glycerol-triformate, glycerol-triacetate (triacetin), glycerol-tripropionate, glycerol-tributyrate (tributyrin), glycerol- trivalerate (trivalerin), glycerol-tr- icaproate (tricaproin), glycerol-trihepanoate (triheptanoin), glycerol-tricaprylate (tricaprylin).
[6] Edible plant oils of reconstructed triglycerides composed only of unsaturated fatty acids which are obtained by complete elimination of saturated fatty acids, starting from conventional edible plant oils by a manufacturing procedures in Claim 1-5.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
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| JP2009516392A JP5132679B2 (en) | 2006-06-22 | 2007-06-14 | Edible oil from which saturated fatty acids have been removed, and method for producing the same (EDIBLEPLANTOILSROMWHICHSATURATEDFATTYACIDSWIREREMOVEEDANDAMUNDFACTURINGPROCESSTHEREOF) |
| CN200780023227.6A CN101472483B (en) | 2006-06-22 | 2007-06-14 | Edible plant oils from which saturated fatty acids were removed and manufacturing process thereof |
| US12/305,364 US8133518B2 (en) | 2006-06-22 | 2007-06-14 | Edible plant oils from which saturated fatty acids were removed and manufacturing process thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2006-0056521 | 2006-06-22 | ||
| KR20060056521 | 2006-06-22 | ||
| KR10-2007-0028768 | 2007-03-23 | ||
| KR1020070028768A KR100741406B1 (en) | 2006-06-22 | 2007-03-23 | Edible plant oil which were removed saturated fatty acid therefrom and chemical process thereof |
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| WO2007148889A1 true WO2007148889A1 (en) | 2007-12-27 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104255949A (en) * | 2014-09-19 | 2015-01-07 | 广东润科生物工程有限公司 | Peanut blend oil containing docosahexaenoic acid (DHA), and preparation method thereof |
| CN104255952A (en) * | 2014-09-19 | 2015-01-07 | 广东润科生物工程有限公司 | DHA-containing corn blend oil and preparation method thereof |
| CN105316107A (en) * | 2014-07-02 | 2016-02-10 | 贵州周以晴生物科技有限公司 | Separation method of oleic acid and linoleic acid in tea seed oil |
| CN108690710A (en) * | 2018-07-27 | 2018-10-23 | 河南省口岸食品检验检测所 | A kind of preparation method of rapeseed oil |
| CN109943611A (en) * | 2019-02-25 | 2019-06-28 | 周国尧 | A kind of preparation method and applications of three seeds peptide and threeway oil |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105316107A (en) * | 2014-07-02 | 2016-02-10 | 贵州周以晴生物科技有限公司 | Separation method of oleic acid and linoleic acid in tea seed oil |
| CN104255949A (en) * | 2014-09-19 | 2015-01-07 | 广东润科生物工程有限公司 | Peanut blend oil containing docosahexaenoic acid (DHA), and preparation method thereof |
| CN104255952A (en) * | 2014-09-19 | 2015-01-07 | 广东润科生物工程有限公司 | DHA-containing corn blend oil and preparation method thereof |
| CN108690710A (en) * | 2018-07-27 | 2018-10-23 | 河南省口岸食品检验检测所 | A kind of preparation method of rapeseed oil |
| CN108690710B (en) * | 2018-07-27 | 2022-04-05 | 河南省食品检验研究院 | Preparation method of rapeseed oil |
| CN109943611A (en) * | 2019-02-25 | 2019-06-28 | 周国尧 | A kind of preparation method and applications of three seeds peptide and threeway oil |
| CN109943611B (en) * | 2019-02-25 | 2021-03-30 | 周国尧 | Preparation method and application of three-seed peptide and three-way oil |
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