WO2014158011A1 - A process for refining palm-pressed fibre oil (ppfo) to produce refined oil and the refined oil thereof - Google Patents
A process for refining palm-pressed fibre oil (ppfo) to produce refined oil and the refined oil thereof Download PDFInfo
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- WO2014158011A1 WO2014158011A1 PCT/MY2014/000042 MY2014000042W WO2014158011A1 WO 2014158011 A1 WO2014158011 A1 WO 2014158011A1 MY 2014000042 W MY2014000042 W MY 2014000042W WO 2014158011 A1 WO2014158011 A1 WO 2014158011A1
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- Prior art keywords
- ppfo
- refined
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- process according
- oil
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 44
- 239000000835 fiber Substances 0.000 title claims abstract description 15
- 238000007670 refining Methods 0.000 title claims abstract description 9
- 239000003921 oil Substances 0.000 claims abstract description 39
- 235000005473 carotenes Nutrition 0.000 claims abstract description 27
- 150000001746 carotenes Chemical class 0.000 claims abstract description 27
- 238000002156 mixing Methods 0.000 claims abstract description 9
- 238000005194 fractionation Methods 0.000 claims abstract description 8
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 54
- 235000019198 oils Nutrition 0.000 claims description 34
- 229930003427 Vitamin E Natural products 0.000 claims description 27
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 27
- 235000019165 vitamin E Nutrition 0.000 claims description 27
- 239000011709 vitamin E Substances 0.000 claims description 27
- 229940046009 vitamin E Drugs 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 238000004061 bleaching Methods 0.000 claims description 25
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 18
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 18
- 229910052698 phosphorus Inorganic materials 0.000 claims description 18
- 239000011574 phosphorus Substances 0.000 claims description 18
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims description 17
- 238000009875 water degumming Methods 0.000 claims description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 235000021588 free fatty acids Nutrition 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 239000012153 distilled water Substances 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 claims description 4
- 235000006008 Brassica napus var napus Nutrition 0.000 claims description 4
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 claims description 4
- 244000188595 Brassica sinapistrum Species 0.000 claims description 4
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 4
- 244000068988 Glycine max Species 0.000 claims description 4
- 235000010469 Glycine max Nutrition 0.000 claims description 4
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 4
- 239000008158 vegetable oil Substances 0.000 claims description 4
- 230000006866 deterioration Effects 0.000 claims description 2
- 239000007844 bleaching agent Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UPYKUZBSLRQECL-UKMVMLAPSA-N Lycopene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1C(=C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=C)CCCC2(C)C UPYKUZBSLRQECL-UKMVMLAPSA-N 0.000 description 3
- 235000021466 carotenoid Nutrition 0.000 description 3
- 150000001747 carotenoids Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 3
- 235000019482 Palm oil Nutrition 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000019519 canola oil Nutrition 0.000 description 2
- 239000000828 canola oil Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
- GJJVAFUKOBZPCB-ZGRPYONQSA-N (r)-3,4-dihydro-2-methyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2h-1-benzopyran-6-ol Chemical class OC1=CC=C2OC(CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-ZGRPYONQSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- 241001677259 Acanthophoenix rubra Species 0.000 description 1
- 240000003133 Elaeis guineensis Species 0.000 description 1
- 235000001950 Elaeis guineensis Nutrition 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 125000002640 tocopherol group Chemical class 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 229930003802 tocotrienol Natural products 0.000 description 1
- 239000011731 tocotrienol Substances 0.000 description 1
- 229940068778 tocotrienols Drugs 0.000 description 1
- 235000019148 tocotrienols Nutrition 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
-
- 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
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
- C11B3/04—Refining fats or fatty oils by chemical reaction with acids
-
- 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
- C11B3/00—Refining fats or fatty oils
- C11B3/10—Refining fats or fatty oils by adsorption
Definitions
- the present invention provides a process for refining palm-pressed fibre oil (PPFO) to produce refined oil and the refined oil thereof.
- PPFO palm-pressed fibre oil
- Palm pressed-fibre is a by-product obtained from the oil extraction process of oil palm fruits in palm oil mills. Conventionally, the PPF is burned as fuel to provide energy for the mill operations.
- the residual oil extracted from PPF contains high concentrations of carotenoids, vitamin E and sterols (Choo et ai, 1996).
- the PPFO has been reported as a good source of health supplements to fulfil certain daily vitamin requirements including carotenes (pro-vitamin A), vitamin E (tocopherols and tocotrienols), squalene, sterols and phospholipids (Choo et al, 1996, 2003; Lau et al, 2008 and Rusnani et al, 2012).
- the phospholipids composition in palm-pressed fiber oil has also been well-studied and reported (Choo et al, 2004). All these studies had suggested that PPFO has a wide range of applications in pharmaceuticals, food and cosmetics industries.
- the present invention provides a refining technology for PPFO to enable greater market application of the oil and value addition.
- the present invention provides a process for refining palm-pressed Fibre oil (PPFO) to produce refined oil, the process includes the steps of (a) water-degumming of the PPFO using water like distilled water at a temperature ranging from 70°C to 110°C preferably at 80°C for a period of less than 40 minutes, (b) acidic water-degumming of the PPFO using acid like phosphoric acid at a temperature ranging from 70°C to 110°C preferably at 80°C for a period of less than 40 minutes, (c) dry degumming of PPFO at a temperature ranging from 70°C to 110°C preferably at 80°C for a period of less than 40 minutes, (d) bleaching of PPFO using bleaching earth at a temperature ranging from 90°C to 115°C preferably at 105°C for a period of less than 40 minutes, (e) high vacuum deacidification of PPFO is conducted at a temperature less than 200°C and pressure less than 0.01 mbar
- the present invention provides a process for refining palm-pressed fibre oil [PPFO) to produce refined oil, the process includes the steps of (a) water-degumming of the PPFO using water like distilled water at a temperature ranging from 70°C to 110°C preferably at 80°C for a period of less than 40 minutes, (b) acidic water-degumming of the PPFO using acid like phosphoric acid at a temperature ranging from 70°C to 110°C preferably at 80°C for a period of less than 40 minutes, (c) dry degumming of PPFO at a temperature ranging from 70°C to 110°C preferably at 80°C for a period of less than 40 minutes, (d) bleaching of PPFO using bleaching earth at a temperature ranging from 90°C to 115°C preferably at 105°C for a period of less than 40 minutes, (e) high vacuum deacidification of PPFO is conducted at a temperature less than 200°C and pressure less than 0.01 mbar,
- PPFO is treated using a combination of processes comprising degumming and bleaching in order to the produce RPPFO.
- Acid degumming is applied to complete the degumming process followed by bleaching.
- all minor components such as carotenoids and palm vitamin E are reserved in the RPPFO.
- Different types of bleaching agents with various dosages in the range of 0.1 to 1.0 %wt are investigated. Significantly high amount of carotenoids is retained for all types of bleaching agents used in the bleached oil.
- Silica-based bleaching agent is found to reduce vitamin E content at high dosage treatment.
- the process of the present invention may also include step of fractionation of refined PPFO to produce refined PPFO olein enriched with high concentration carotenes and vitamin E.
- the process of the present invention may also include step of blending of refined PPFO olein with refined, bleached and deodorised RBD palm olein (RBDPOo) and other refined vegetable oils e.g. canola, soyabean, rapeseed oils and others.
- RBDPOo bleached and deodorised RBD palm olein
- the blending ratio between refined PPFO olein with the RBDPOo and other refined vegetable oils e.g. canola, soyabean, rapeseed oils and others is more than 30% refined PPFO olein.
- the bleaching earth is selected from natural bleaching earth, acid activated bleaching earth and silica based bleaching earth or any combination thereof. It is preferred that the PPFO used in the present invention to have DOBI value of more than 2.0 and/or to have phosphorus content value of less than 30 ppm and/or to have free fatty acid (FFA) value of less than 0.2%wt and/or to have the PFFO to be enriched with minor components such as carotenes and vitamin E.
- DFA free fatty acid
- the final stage of refining process is high vacuum deacidification in order to remove fatty acid and residual oxidation products under controlled conditions.
- the RPPFO is further refined via fractionation process in order to produce refined red palm fibre olein (RRedPFO olein) fractions with high phytonutrients contents.
- the fractionated RRedPFO olein can then be blended with other oils to produce the red blended oil rich in carotenes and vitamin E.
- Step 1 Water-degumming 82 2.01
- the water-degummed fibre oil was subjected to dry degumming process by adding 0.05%wt of phosphoric acid in aqueous solution and heated to 90°C for 10 min. About 0.1%of bleaching earth was added to the mixture and stirred at 105°C for 15 min under nitrogen blanketing. The bleaching earth was filtered and the oil was dried under vacuum. The refined PPFO was analysed for its carotenes and vitamin E content. The results were shown in Table 4. The carotenes and vitamin E were retained in the water- degummed fibre oil.
- the water-degummed Fibre oil was subjected to dry degumming process by adding 0.05%wt of phosphoric acid in aqueous solution and heated to 90°C for 10 min. About 0.1%of bleaching earth was added to the mixture and stirred at 105°C for 15 min under nitrogen blanketing. The bleaching earth was Filtered and subjected to high vacuum distillation using short path distiller at 180°C and 0.01 mbar. The reFined PPFO was analysed for the phosphorous content, DOBI, free fatty acid (FFA), carotenes and vitamin E content. The results were shown in Table 5. The carotenes and vitamin E were retained in the Final reFined PPFO. The FFA content was reduced to 0.15%wt. DOBI has been increased from 1.99 to 2.87.
- Step 1 Water-degumming 100 1358 1097 2.6189 -
- Step 2 Water-degumming 62 1323 1048 2.6544 -
- Example 5 The refined PPFO obtained in Example 5 was subjected to dry fractionation for cooling period of 10 hours. The final holding temperature was 24°C. The cooled refined PPFO was filter at pressure of 15 barg. The filtrate and solid were collected and analysed for their carotenes and vitamin E content. The yield of filtrate was 78% based on feed. The results were shown in Table 7.
- Example 7 The refined PPFO obtained in Example 7 was blended with refined, bleached and deodorised palm olein (RBDPOo) at ratio of PPFO to RBDPOo of 1:1, 2:1 and 1:2. The experiment was repeated by blending refined PPFO with refined canola oil at similar ratio. The blended oils were tested for their carotenes and vitamin E content. The results were shown in Table 8. The blended oils with different concentrations of carotenes and vitamin E were obtained.
- RBDPOo bleached and deodorised palm olein
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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BR112015024681-8A BR112015024681B1 (en) | 2013-03-27 | 2014-03-25 | process for refining palm pressed fiber oil |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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MYPI2013001075 | 2013-03-27 | ||
MYPI2013001075 | 2013-03-27 |
Publications (1)
Publication Number | Publication Date |
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WO2014158011A1 true WO2014158011A1 (en) | 2014-10-02 |
Family
ID=51624859
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/MY2014/000042 WO2014158011A1 (en) | 2013-03-27 | 2014-03-25 | A process for refining palm-pressed fibre oil (ppfo) to produce refined oil and the refined oil thereof |
Country Status (2)
Country | Link |
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BR (1) | BR112015024681B1 (en) |
WO (1) | WO2014158011A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10851327B2 (en) | 2018-06-11 | 2020-12-01 | Poet Research, Inc. | Methods of refining a grain oil composition feedstock, and related systems, compositions and uses |
US11008531B2 (en) | 2018-02-09 | 2021-05-18 | Poet Research, Inc. | Methods of refining a grain oil composition to make one or more grain oil products, and related systems |
US11987832B2 (en) | 2020-08-06 | 2024-05-21 | Poet Research, Inc. | Endogenous lipase for metal reduction in distillers corn oil |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4089880A (en) * | 1975-03-13 | 1978-05-16 | Sullivan Systems Inc. | Proces for refining fatty oils |
US4623489A (en) * | 1985-04-02 | 1986-11-18 | Rivers Jr Jacob B | Method of refining edible oil for preventing auto-oxidation of the oil |
US4981620A (en) * | 1984-07-30 | 1991-01-01 | Cpc International Inc. | In-line dewaxing of edible vegetable oils |
CN101805667A (en) * | 2010-04-02 | 2010-08-18 | 安徽省思润谷物油精炼有限公司 | Method for dry degumming and refining of edible rice bran oil |
WO2011002275A1 (en) * | 2009-06-30 | 2011-01-06 | Sime Darby Malaysia Berhad | Process for manufacturing palm oil fractions containing virtually no 3-monochloropropanediol fatty acid esters |
-
2014
- 2014-03-25 WO PCT/MY2014/000042 patent/WO2014158011A1/en active Application Filing
- 2014-03-25 BR BR112015024681-8A patent/BR112015024681B1/en active IP Right Grant
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4089880A (en) * | 1975-03-13 | 1978-05-16 | Sullivan Systems Inc. | Proces for refining fatty oils |
US4981620A (en) * | 1984-07-30 | 1991-01-01 | Cpc International Inc. | In-line dewaxing of edible vegetable oils |
US4623489A (en) * | 1985-04-02 | 1986-11-18 | Rivers Jr Jacob B | Method of refining edible oil for preventing auto-oxidation of the oil |
WO2011002275A1 (en) * | 2009-06-30 | 2011-01-06 | Sime Darby Malaysia Berhad | Process for manufacturing palm oil fractions containing virtually no 3-monochloropropanediol fatty acid esters |
CN101805667A (en) * | 2010-04-02 | 2010-08-18 | 安徽省思润谷物油精炼有限公司 | Method for dry degumming and refining of edible rice bran oil |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11008531B2 (en) | 2018-02-09 | 2021-05-18 | Poet Research, Inc. | Methods of refining a grain oil composition to make one or more grain oil products, and related systems |
US10851327B2 (en) | 2018-06-11 | 2020-12-01 | Poet Research, Inc. | Methods of refining a grain oil composition feedstock, and related systems, compositions and uses |
US11530369B2 (en) | 2018-06-11 | 2022-12-20 | Poet Research, Inc. | Methods of refining a grain oil composition |
US11912958B2 (en) | 2018-06-11 | 2024-02-27 | Poet Research, Inc. | Methods of refining a grain oil composition |
US11952553B2 (en) | 2018-06-11 | 2024-04-09 | Poet Research, Inc. | Methods of refining a grain oil composition |
US11987832B2 (en) | 2020-08-06 | 2024-05-21 | Poet Research, Inc. | Endogenous lipase for metal reduction in distillers corn oil |
Also Published As
Publication number | Publication date |
---|---|
BR112015024681B1 (en) | 2021-01-26 |
BR112015024681A2 (en) | 2017-07-18 |
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