EP3292190A1 - Procédé de dégommage d'huiles triglycéridiques - Google Patents
Procédé de dégommage d'huiles triglycéridiquesInfo
- Publication number
- EP3292190A1 EP3292190A1 EP15891363.2A EP15891363A EP3292190A1 EP 3292190 A1 EP3292190 A1 EP 3292190A1 EP 15891363 A EP15891363 A EP 15891363A EP 3292190 A1 EP3292190 A1 EP 3292190A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- oil
- homogenization apparatus
- treated oil
- oil mixture
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 55
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 239000003921 oil Substances 0.000 title claims description 217
- 238000000265 homogenisation Methods 0.000 claims abstract description 93
- 235000019198 oils Nutrition 0.000 claims description 210
- 239000000203 mixture Substances 0.000 claims description 113
- 239000002253 acid Substances 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 20
- 239000008158 vegetable oil Substances 0.000 claims description 18
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 12
- 239000011574 phosphorus Substances 0.000 claims description 12
- 229910052698 phosphorus Inorganic materials 0.000 claims description 12
- 102000004190 Enzymes Human genes 0.000 claims description 10
- 108090000790 Enzymes Proteins 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 238000011144 upstream manufacturing Methods 0.000 claims description 6
- 239000012530 fluid Substances 0.000 abstract description 12
- 239000012535 impurity Substances 0.000 abstract description 12
- 238000000926 separation method Methods 0.000 abstract description 12
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 4
- 239000002585 base Substances 0.000 description 29
- 239000012071 phase Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 23
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 229910052742 iron Inorganic materials 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 8
- 235000012424 soybean oil Nutrition 0.000 description 8
- 239000003549 soybean oil Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 239000011260 aqueous acid Substances 0.000 description 5
- 238000007670 refining Methods 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000010779 crude oil Substances 0.000 description 4
- -1 e.g. Substances 0.000 description 4
- 235000021388 linseed oil Nutrition 0.000 description 4
- 239000000944 linseed oil Substances 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000019519 canola oil Nutrition 0.000 description 3
- 239000000828 canola oil Substances 0.000 description 3
- 235000005687 corn oil Nutrition 0.000 description 3
- 239000002285 corn oil Substances 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000004533 oil dispersion Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 235000019489 Almond oil Nutrition 0.000 description 2
- 235000004936 Bromus mango Nutrition 0.000 description 2
- 235000019492 Cashew oil Nutrition 0.000 description 2
- 235000003901 Crambe Nutrition 0.000 description 2
- 241000220246 Crambe <angiosperm> Species 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 235000019487 Hazelnut oil Nutrition 0.000 description 2
- 241000221089 Jatropha Species 0.000 description 2
- 241001072282 Limnanthes Species 0.000 description 2
- 235000018330 Macadamia integrifolia Nutrition 0.000 description 2
- 235000003800 Macadamia tetraphylla Nutrition 0.000 description 2
- 240000000912 Macadamia tetraphylla Species 0.000 description 2
- 235000014826 Mangifera indica Nutrition 0.000 description 2
- 240000007228 Mangifera indica Species 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- 235000019495 Pecan oil Nutrition 0.000 description 2
- 235000019496 Pine nut oil Nutrition 0.000 description 2
- 235000019497 Pistachio oil Nutrition 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- 235000019774 Rice Bran oil Nutrition 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- 235000009184 Spondias indica Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 2
- 241001135917 Vitellaria paradoxa Species 0.000 description 2
- 235000019498 Walnut oil Nutrition 0.000 description 2
- 239000010472 acai oil Substances 0.000 description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 2
- 239000008168 almond oil Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000010480 babassu oil Substances 0.000 description 2
- 235000021324 borage oil Nutrition 0.000 description 2
- 239000010474 borage seed oil Substances 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000010467 cashew oil Substances 0.000 description 2
- 229940059459 cashew oil Drugs 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 239000010636 coriander oil Substances 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 239000008169 grapeseed oil Substances 0.000 description 2
- 239000010468 hazelnut oil Substances 0.000 description 2
- 239000010460 hemp oil Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229940119170 jojoba wax Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000008164 mustard oil Substances 0.000 description 2
- 239000010466 nut oil Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 239000003346 palm kernel oil Substances 0.000 description 2
- 235000019865 palm kernel oil Nutrition 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 239000010470 pecan oil Substances 0.000 description 2
- 239000010490 pine nut oil Substances 0.000 description 2
- 239000010471 pistachio oil Substances 0.000 description 2
- 229940082415 pistachio oil Drugs 0.000 description 2
- 239000010491 poppyseed oil Substances 0.000 description 2
- 239000008165 rice bran oil Substances 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 229940057910 shea butter Drugs 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- 235000020238 sunflower seed Nutrition 0.000 description 2
- 239000003784 tall oil Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 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 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000008170 walnut oil Substances 0.000 description 2
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical class CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000009875 water degumming Methods 0.000 description 1
Classifications
-
- 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
- C11B3/16—Refining fats or fatty oils by mechanical means
-
- 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
- C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
-
- 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
- C11B3/02—Refining fats or fatty oils by chemical reaction
- C11B3/06—Refining fats or fatty oils by chemical reaction with bases
Definitions
- the invention relates to improved processes for refining oils, and more particularly, improved processes for degumming triglyceride oils having impurities.
- Vegetable oils are typically oils that have been pressed or extracted, such as from a vegetable source. Many vegetable oils contain some form of phosphatides (e.g., hydratable or non-hydratable), commonly known as gums. For instance, soybean oil contains about 1-3%, corn oil 0.6-0.9%, sunflower oil 0.5-0.9%), and canola oil (crude) 1-3% of gums.
- phosphatides e.g., hydratable or non-hydratable
- Gums can be partially or totally removed from vegetable oils through several different known degumming processes.
- the most commonly used processes in the industry are water degumming, acid degumming, caustic refining and enzymatic degumming, for example, as disclosed in U.S. Pat. Nos. 4,049,686; 5,239,096; 5,264,367; 5,286,886; 6,001,640; 6,033,706; 7,494,676 and 7,544,820, and U.S. Pat. Pub. Nos. 2007/0134777; 2008/0182322 and
- a method disclosed in U.S. Pat. No. 4,240,972 discloses adding an acid to a heated stream of crude vegetable oil and then immediately passing the mixture through a static mixer to produce an acid-in-oil dispersion, and then separating the dispersion into an oil phase and an aqueous phase containing the phosphatides.
- U.S. Pat. No. 4,240,972 discloses adding an acid to a heated stream of crude vegetable oil and then immediately passing the mixture through a static mixer to produce an acid-in-oil dispersion, and then separating the dispersion into an oil phase and an aqueous phase containing the phosphatides.
- 4,698,185 describes a vegetable oil refining method with the steps of dispersing an aqueous organic acid in a water-degummed oil to form an acid-in-oil dispersion, allowing the phases to remain in contact for a time sufficient to decompose metal salts of phosphatidic acid, adding a base to the acid-in- oil dispersion to increase pH to above 2.5 without substantial formation of soap, and finally separating the dispersion into an oil phase and an aqueous phase containing the phosphatides.
- U.S. Pat. Nos. 4,698,185 and 6,0159,15 describe processes for degumming vegetable oil using a high shear Ultra-Turax rotor /stator apparatus.
- U.S. Pat. No. 6,172,248 describes a method for refining vegetable oils and byproducts thereof. In an organic acid refining process, vegetable oil is combined with a dilute aqueous organic acid solution and subjected to high shear to finely disperse the acid solution in the oil.
- High shear rotor/stator apparatus are known to be used to generate hydrodynamic cavitation in fluids.
- Cavitation has a tendency to release dissolved gases in an oil mixture and generate post cavitation gas fields of tiny bubbles in the fluid flow. Those bubbles become coagulation centers for the soap stock particles, entrap oil in the larger agglomerates and can decrease phase boundary in the oil-acid/base solution. As a result, the rate of hydrolysis of phosphatides, and the degree of removal thereof, in the purification process will decrease as the fields of bubbles persist in the fluid. Entrapment of the oil in the larger agglomerates can also increase oil yield losses.
- 2014/0087042 involves mixing crude oil with degumming agents, e.g., water or acid, and passing the mixture through a hydrodynamic cavitation device.
- degumming agents e.g., water or acid
- Numerous flow-through hydrodynamic apparatuses are known, for example, those disclosed in U.S. Pat. Nos. 5,810,052; 5,971,601; 5,969,207; 6,035,897; 6,502,979; 6,705,396; 7,338,551 and 7,207,712.
- Cavitational processing provides the highest shear to oil degumming processes but at the same time extracts dissolved gases from liquids and generates post cavitation gas fields of tiny bubbles in the flow. Accordingly, there is a continuing need for a method for degumming that can provide the highest shear to the process but at the same time eliminate the cavitational degassing problem observed in known methods.
- a method for degumming a triglyceride oil can include the steps of mixing an aqueous base solution with an acid-treated oil to form a pre -treated oil mixture comprising an oil phase and a water phase.
- the pre-treated oil mixture at a pre-determined inlet pressure can be passed through two homogenization apparatuses in series with one another, for example, a first homogenization apparatus and a second homogenization apparatus, to form a treated oil mixture.
- the first and second homogenization apparatuses each include at least three flow constrictions in series for dispersing the contents, such as acid, base and water, of the pre-treated oil mixture.
- the pre-treated oil mixture is subjected to a pressure drop across each flow constriction in the first and second homogenization apparatuses in the range of 25 to 50 percent of the upstream pressure of the pre-treated oil mixture before each flow constriction.
- the pressure drop across each flow constriction is such that hydrodynamic cavitation in the pre-treated oil mixture is entirely avoided and suppressed in both the first and second homogenization apparatuses.
- the treated oil mixture can be further processed by separating the water phase from the oil phase to form a purified oil.
- the method can further include a step of mixing a triglyceride oil with an aqueous acid solution to form the acid-treated oil to be mixed with the base.
- the triglyceride oil can be mixed with the aqueous acid in a tank prior to mixing with the aqueous base solution with the acid-treated oil.
- the pre-determined inlet pressure of the pre-treated oil mixture prior to being passed through the first flow constriction in the first homogenization apparatus can be in the range of 800 to 2,000 psi.
- constrictions contained therein can be in the range of 60 to 80% of the pre-determined inlet pressure.
- the pressure drop in the pre-treated oil mixture across each flow constriction in the first homogenization apparatus can be at least 100 psi. In another example, the pressure drop in the pre-treated oil mixture across each flow constriction in the second homogenization apparatus can be not more than 100 psi.
- the pre-treated oil mixture enters the second homogenization apparatus at a second inlet pressure
- the pressure drop in the pre-treated oil mixture across the second homogenization apparatus for example across all flow constrictions contained there, can be in the range of 60 to 80% of the second inlet pressure.
- the treated oil mixture exiting the second homogenization apparatus can be at a pressure less than 10% of the pre-determined inlet pressure, e.g., in the range of 800 to 2,000 psi.
- the pre-treated oil mixture in the first homogenization apparatus and the second homogenization apparatus can have a cavitation number in the range of greater than 2 and less than 5.
- the flow constrictions in the first and second homogenization apparatuses can be valves.
- the valves can have a sharp edge surface for providing shear to the oil mixture, such as the valves having a knife edge.
- the flow constrictions can be arranged in the first or second homogenization apparatuses radially in series or axially in series.
- the method for degumming a triglyceride oil can yield a purified oil having a phosphorus content of less than 10 ppm.
- the method can include an enzyme being added to the pre-treated oil mixture prior to the mixture being passed through the first and second homogenization apparatuses.
- the triglyceride oil in the pre-treated oil mixture can be crude vegetable oil or water- degummed vegetable oil.
- the crude vegetable oil or water-degummed vegetable oil can be selected from the group consisting of acai oil, almond oil, babassu oil, blackcurrent seed oil, borage seed oil, canola oil, cashew oil, castor oil, coconut oil, coriander oil, corn oil, cottonseed oil, crambe oil, flax seed oil, grape seed oil, hazelnut oil, hempseed oil, jatropha oil, jojoba oil, linseed oil, macadamia nut oil, mango kernel oil, meadowfoam oil, mustard oil, neat's foot oil, olive oil, palm oil, palm kernel oil, palm olein, peanut oil, pecan oil, pine nut oil, pistachio oil, poppy seed oil, rapeseed oil, rice bran oil, safflower oil, sasanqua oil, sesame oil
- the acid-treated oil can include an acid selected from the group consisting phosphoric acid, hydrochloric acid, sulfuric acid, ascorbic acid, acetic acid, citric acid, fumaric acid, maleic acid, tartaric acid, succinic acid, glycolic acid or a mixture thereof.
- the pre-treated oil mixture can include a base selected from the group consisting of sodium hydroxide, potassium
- hydroxide sodium silicate, sodium carbonate, calcium carbonate or a mixture thereof.
- FIG. 1 shows a block flow diagram of an oil degumming method using first and second homogenization apparatus to reduce phosphatide levels in the oil being treated.
- a range such as 5-25 (or 5 to 25) is given, this means preferably at least 5 and, separately and independently, preferably not more than 25. In an example, such a range defines independently not less than 5, and separately and independently, not less than 25.
- a method has been discovered for an efficient, cost-effective oil degumming process by use of a first and second homogenization apparatus combination.
- the oil to be treated is mixed with an acid, base and water. It has been found that a multi-stage flow constriction homogenization apparatus in series with another multi-stage flow constriction homogenization apparatus can improve reduction in phosphatide content with a higher oil yield.
- the first and second homogenization apparatuses contain multiple flow constrictions for dispersing the oil, acid, base and water such that hydrodynamic cavitation is suppressed in both homogenization apparatuses.
- one embodiment of a method for degumming oils can include multiple stages. As shown in the drawing, pipes, hoses, or other conventional, industrial equipment can be used to facilitate the fluid communication of the elements and streams discussed below.
- Oil is shown as stream 1 in FIG. 1.
- the oils that can be degummed include vegetable oils, such as crude vegetable oil or water-degummed oil.
- vegetable oils can include, for example, acai oil, almond oil, babassu oil, blackcurrent seed oil, borage seed oil, canola oil, cashew oil, castor oil, coconut oil, coriander oil, corn oil, cottonseed oil, crambe oil, flax seed oil, grape seed oil, hazelnut oil, hempseed oil, jatropha oil, jojoba oil, linseed oil, macadamia nut oil, mango kernel oil, meadowfoam oil, mustard oil, neat's foot oil, olive oil, palm oil, palm kernel oil, palm olein, peanut oil, pecan oil, pine nut oil, pistachio oil, poppy seed oil, rapeseed oil, rice bran oil, safflower oil, sasanqua oil, sesame oil, shea butter,
- the phosphatide or phosphorus content of the oil 1 can be in the range of 30 to 1 ,200 ppm.
- the phosphatide content (or also referred to as phospholipid content), as used herein, is expressed as ppm phosphorus in oil.
- the phosphatide content of crude oil, such as vegetable crude oil can be in the range of 200 to 1,200 ppm phosphorus.
- the phosphatide content of previously water-degummed oil, such as water-degummed vegetable oil can be in the range of 30 to 200 ppm phosphorus.
- the oil 1 can be heated prior to the degumming method (not shown), such as prior to acid being added to form an acid-treated oil.
- the oil can be passed through a heat exchanger, such as a plate and frame heat exchanger, to increase or decrease the temperature of the oil as desired.
- the oil can be heated to a temperature in the range of 20 to 100° C, or at least to 30, 40, 50, 60, 70, 80, 90 or 100° C.
- the oil is maintained at a temperature in the range of 40 to 95° C during the degumming process as deemed suitable to one skilled in the art.
- An acid such as an aqueous acid solution
- Acids can promote hydration of the non-hydrated phosphatides contained in the oil.
- the acid is shown as stream 2.
- the acid can include an inorganic or organic acid, for example, phosphoric acid, hydrochloric acid, sulfuric acid, ascorbic acid, acetic acid, citric acid, fumaric acid, maleic acid, tartaric acid, succinic acid, glycolic acid or a combination or mixture thereof.
- the acid is used in range from about 50 to 500 ppm as measured by weight of the oil.
- a high concentration acid in water solution can be used, such as a 75 weight percent phosphoric acid water solution.
- the aqueous acid solution can be stored in a working or holding tank prior to being added to the oil 1.
- the acid-treated oil 3 can optionally be passed through a mixer to disperse the acid 2 in the oil 1.
- a mixer Any suitable mixer can be used, for example, the use of a dynamic mixer is preferred to disperse the acid in the oil.
- Using a dynamic mixer can provide more effective mixing and promote the use of concentrated acid solutions, which can reduce the volume of acid solution being added to the oil. Examples of mixers that can be used include centrifugal pumps or in-line mixers.
- the acid-treated oil 3 can be optionally transferred to a holding or mixing tank 4.
- the tank 4 can store or further mix the acid-treated oil for a suitable predetermined amount of time.
- the acid-treated oil can be held for a period of 1 minute to 24 hours.
- the tank can be equipped with a mixer or stirrer for maintaining a homogenous mixture.
- the tank can be jacketed or equipped with another heating apparatus, such as coils, for maintaining a desired holding temperature (not shown).
- a base such as in an aqueous base solution, can be added to and mixed with the acid- treated oil 6 to form a pre-treated oil mixture 8, for example before being passed through a first homogenization apparatus 10.
- the base can be added to neutralize the acid-oil mixture, for instance, to bring the pH of the mixture to a range of 5 to 8, and preferably 6 to 7.
- the base can promote the neutralization of free fatty acids contained in the acid-oil mixture.
- the base can be stored in a working or holding tank prior to being added to the acid-treated oil. The base is shown as stream 7.
- the base 7 can include sodium hydroxide, potassium hydroxide, sodium silicate, sodium carbonate, calcium carbonate, or combinations thereof.
- the base can be used in range from 0.02 to 0.2 percent by weight based on total weight of the oil in the acid-treated oil.
- Concentrated base solutions for instance, between 30 and 50 weight percent, can be used to reduce the amount of volume of base solution being added. Beyond the stoichiometric amount of base required to neutralize the acid and free fatty acids in the acid-oil mixture, surplus base can be added, for example, to adjust for certain oils to be degummed and the quality thereof.
- the pre-treated oil mixture 8, containing an oil phase and a water phase, is passed to a first homogenizer or homogenization apparatus 10.
- the pre-treated oil mixture 8 can be fed to the apparatus 10 by a pump.
- the pre-treated oil mixture 8 is fed to the apparatus 10 at a pre-determined inlet pressure, for example, in the range of 800 to 2,000 psi, or at least 900, 1,000, 1,250 or 1,500 psi.
- the first homogenization apparatus 10 can have multiple flow constrictions and preferably at least three flow constrictions in series.
- the pre-treated oil mixture 8 under pressure and at low velocity, is forced through each flow constriction where the velocity is increased and a corresponding decrease in pressure in the pre-treated oil mixture 8 results.
- the construction or design of the flow constriction can accelerate the mixture 8 radially. Passage through the flow constrictions, and the increase in velocity and pressure drop, releases energy that causes turbulence and localized pressure fluctuations that finely disperse the oil, acid, base and water mixture to promote an acid-oil interface for transferring impurities in the oil to the water phase.
- the first homogenization apparatus 10 can be a high pressure valve homogenizer apparatus.
- the first homogenization apparatus 10 can have a sharp edge or knife edge element in close proximity with a ring or seat surface of a valve acting as the flow constriction.
- Knife edge valves are valves with a so called “sharp edge” or “knife edge” profile.
- the valve has an impact surface, for instance a ring structure, surrounding a portion of the adjustable edge or knife edge of the valve.
- Homogenizer valves having a sharp or knife edge can generate high turbulence and shear conditions in the pre -treated oil mixture, which combined with compression, velocity acceleration, pressure drop and flow impact cause the formation of fine emulsion droplets while suppressing and avoiding flow -induced cavitation in the mixture.
- the sharp edge or knife edge element can be adjustable to control the pressure drop of the pre-treated oil mixture across the flow constriction. For example, by adjusting the gap between the sharp edge or knife edge element and the seat of the valve, the flow area in the flow constriction of the homogenizing apparatus 10 is controlled and the resulting pressure drop in the pre-treated oil mixture is regulated such that the dispersion of fluids is magnified without subjecting the mixture to cavitation and degassing drawbacks thereof.
- the mixture 8 flows through the flow constriction, e.g., exiting the valve around the seat or ring member, it can form a radial jet that strikes an impact surface such as an impact ring, for example, a ring member positioned on the valve seat and surrounding the sharp edge or knife edge portion closest to the seat.
- the impact surface blocks or creates an obstruction to the flow of the mixture near the gap between the seal and adjustable knife edge or sharp edge element of the valve.
- the first homogenization apparatus 10 can be the high pressure homogenization devices supplied by APV Rannie.
- Other homogenization apparatuses can be used, such as those manufactured by Bran+Leubbe or Niro Soavi that can produce high pressure, high shear homogenization in fluids.
- suitable homogenization apparatuses can include the devices disclosed in U.S. Patent Nos. 3,243,157; 3,515,370; 4,060,099; 5,451,106; 6,550,956 and 6,299,342.
- Cavitation in the first homogenization apparatus 10 is suppressed by maintaining the pressure drop across each flow constriction at a level to avoid inducing or generating a cavitation bubble in the mixture 8, which eliminates degassing of fluid components.
- Each flow constriction in the apparatus 10 has an inlet pressure immediately upstream of the flow constriction and an exit pressure immediately downstream of the flow constriction, which defines a total pressure drop in the pre-treated mixture across a particular flow constriction.
- the pressure drop in the pre-treated oil mixture 8 across any flow constriction can be in the range of 25 to 50, or 30 to 40 percent of the upstream inlet pressure to the flow constriction.
- the pressure drop in the mixture 8 across a flow constriction can be at least 30, 35, 40 or 45 percent of the upstream inlet pressure. In another embodiment, the pressure drop in the mixture 8 across a flow constriction can be in the range of 100 to 500 psi, or at least 125, 150. 175 or 200 psi.
- the pressure drop in the pre-treated oil mixture 8 can be measured across the first homogenization apparatus 10, which includes the pressure drop across all flow constrictions contained therein.
- the pressure drop in the pre-treated oil mixture across the first homogenization apparatus 10 includes the pressure drop across all flow constrictions contained therein.
- homogenization apparatus can be in the range of 60 to 80 percent of the pre-determined inlet pressure to the apparatus, or at least 65, 70 or 75 percent.
- the pressure drop in the pre-treated oil mixture across the first homogenization apparatus can be at least 250, 500 or 750 psi.
- the pre-treated oil mixture 8 exits the first homogenization apparatus 10 in stream 12 and enters a second homogenization apparatus 14 at a second inlet pressure.
- the second inlet pressure of the pre-treated oil mixture 12 can be in the range of 100 to 1,000 psi, or at least 150, 200, 250, 300, 350 or 400 psi.
- the pressure drop in the mixture 12 across a flow constriction in the second apparatus 14 can be at least 30, 35, 40 or 45 percent of the upstream inlet pressure to the constriction.
- the pressure drop in the mixture 12 across a flow constriction can be in the range of 25 to 250 psi, or at least 30, 40, 50, 60, 70 or 80 psi.
- the pressure drop in the pre-treated oil mixture 12 can be measured across the second homogenization apparatus 14, which includes the pressure drop across all flow constrictions contained therein.
- homogenization apparatus can be in the range of 60 to 80 percent of the second inlet pressure to the apparatus 14, or at least 65, 70 or 75 percent.
- the pressure drop in the pre-treated oil mixture 12 across the second homogenization apparatus can be at least 100, 125, 140, 150, 175 or 200 psi.
- the second homogenization apparatus 14 can have multiple flow constrictions and preferably at least three flow constrictions in series.
- the second homogenization apparatus 14 can be the same apparatus as the first homogenization apparatus 10.
- all of the features of the second homogenization apparatus 14 can be the same as described above for the first homogenization apparatus 10, for example, the flow constrictions of the second apparatus 14 can be knife edge valves.
- the second homogenization apparatus 14 further disperses the oil phase and the water phase to promote oil degumming. Turbulence in the pre-treated oil mixture 12 and pressure drop of the mixture 12 through the second homogenization apparatus 14 is controlled in order to suppress the formation of cavitation bubbles in the mixture 12 throughout its entire passage through the apparatus 14.
- the pre-treated oil mixtures 8, 12 can be characterized at points within each of the first and second homogenization apparatuses 10, 14 by a cavitation number.
- a cavitation number above 1 indicates that cavitation does not occur in a fluid.
- the cavitation number should be above 1 but not high enough to reduce turbulence and mixing of the oil and reagents.
- the pre-treated oil mixtures 8, 12 in the first and second homogenization apparatuses 10, 14 are continuously characterized by a cavitation number above 1 , 1.5 or 2 such that cavitation is suppressed during processing of the mixture in the first and second homogenization apparatuses.
- the mixtures 8, 12 can have a cavitation number in the range of 2 to 5 within the first and second homogenization apparatuses, or greater than 2.2, 2.5, 2.8, 3, 3.2, 3.5 or 3.7.
- the cavitation number of the mixture can be below 5, 4.5, 4, 3.5 or 3.
- the cavitation number of the pre-treated oil mixture 8 in the first homogenization apparatus 10 at each flow constriction can be lower than the cavitation number of the pre-treated mixture 12 in the second homogenization apparatus 14 at each flow constriction.
- the pre-treated mixture 8 can have a cavitation number in the range of 2 to 3 within the first homogenization apparatus 10, for example at each flow constriction in the apparatus 10, and the pre-treated mixture 12 can have a cavitation number in the range of 3 to 5 or 3 to 4 within the second homogenization apparatus 14, for example at each flow constriction in the apparatus 14.
- cavitation in the oil mixture can present disadvantages as discussed above.
- flow-induced cavitation has the tendency for extracting dissolved gases from liquids and can generate post-cavitation gas fields of tiny cavitation bubbles in the liquid flow.
- the cavitation bubbles become coagulation centers for soap stock particles and impurities.
- the bubbles can further entrap oil in the larger agglomerates and can decrease phase boundary contact between the oil and acid/base solution.
- the rate of hydrolysis of phosphatides, and the degree of removal thereof, in the oil degumming process will decrease because the intensity of the mass transfer at the interface or phase boundary contact area associated with the supply rate of the reactants, e.g., water, acid, base, through the phase interface will likewise decrease.
- the removal rate of the impurities of the catalytic reaction can decrease in the event of cavitation in the fluid. Suppressing flow-induced cavitation in homogenizer apparatuses can avoid these problems and promote a decrease oil yield losses as compared to cavitation methods.
- phosphatides is almost instantaneous or at least almost completed within seconds.
- a fine dispersion is also needed for neutralization reaction with a base.
- aqueous base droplets are finely dispersed, the interface area between the base and the oil and acid will increase, and diffusion distances will decrease, which will increase the overall neutralization reaction.
- its intensification occurs, there results in an increase in efficiency of the method of degumming a triglyceride oil.
- the oil 1 can be mixed with an enzyme for degumming the oil.
- the pre -treated oil mixture 8 can further include an enzyme as known in the art for use in degumming oils. Solutions or mixtures of enzymes in water can be dilute with low concentrations of enzyme, and those enzyme solutions are generally more dilute than aqueous solutions of acid or base as used in oil degumming. On a molar basis, the dispersion of the enzyme solution or mixture should be fine since the low concentration of enzymes and enzyme stearic requirements can lead to a lower Arrhenius factor for enzymatic reactions.
- the dispersed oil being passed through the first and second homogenization apparatuses can be further processed.
- the treated oil 16 exiting the second homogenization apparatus 14 can be transferred to one or more separation phases to remove the added water, acid, base or other component or a portion thereof and impurities from the oil phase to create a purified oil product.
- the treated oil 16 Prior to separation, can be transferred to a holding tank 18.
- the oil 16 can be mixed or allowed to rest in the holding tank as desired. From the holding tank, the treated oil 18, containing a water phase and an oil phase, can be processed to separate 22 the phases.
- Separation of the water phase from the oil phase can be done with a decanter, centrifuge, hydrocyclone or similar separation equipment.
- the differences in densities of water and oil allows for a rapid and distinct separation of the two components.
- the separator is a gravity tank with a mixer or agitator, the residence time can be selected to allow for gravitational separation of the heavy phase and light phase as desired.
- the separation temperature in a separation vessel can be adjusted as desired, for example, the separation temperature can be in the range of 20° C to 150° C, 30° C to 100° C or 40° C to 80° C.
- the water and oil mixture can be introduced into a separation vessel at a temperature in the range of 20° C to 60° C.
- a water phase 24 and a purified oil 26 are formed.
- the purified oil 26 can be subjected to further processing steps known in the art including bleaching or deodorizing, as may be necessary or desirable depending on the end use for which the degummed oil product is intended.
- the oil degumming methods described herein can be carried out at different temperatures, for instance, at any temperature deemed suitable by one of skill in the art.
- the temperature during the process is in the range from about 20° C to 110° C. In certain embodiments, the temperature during the process is about 20, 30, 40, 50 60, 70, 80, 90, 100 or 110° C.
- the purified oil 26 resulting from separation of water and impurities, such as soaps and phosphatides, has an improved quality.
- the phosphatide content of the purified oil can be less than 100, 90, 80, 70, 60, 50, 40, 35, 30, 20, 15, 10 or 5 ppm, whereas the starting
- phosphatide content of the oil being fed to the homogenization apparatuses can be in the range of 200 to 1200 for crude oils and 30 to 200 for water degummed oils.
- the degumming method described herein can result in a purified oil product having a reduction in phosphatide content of at least 80, 85, 90, 95, 97, 97.5, 98 or 98.5 weight percent, as compared to the oil being fed to the process or being used to form the acid-oil mixture.
- the iron content of the purified oil can be less than 0.15, 0.12, 0.10, 0.09, 0.08, 0.07, 0.06, 0.05, 0.04 or 0.03 ppm, whereas the starting iron content of the oil being fed to the homogenization apparatuses can be in the range of 0.4 to 5 ppm.
- the degumming method described herein can result in a purified oil product having a reduction in iron content of at least 80, 85, 90, 93, 94, 95, 96, 97, 97.5 or 98 weight percent, as compared to the oil being fed to the process or being used to form the acid-oil mixture.
- the pre-treated oil mixture was pressurized and followed by one pass at an inlet pressure of 1,000 psi through two three-stage knife edge valves high-pressure valve homogenizers (design similar to the sown in Fig 5 US Patent 6,550,956) arranged in series (a first and second homogenization).
- a pressure drop across each homogenizing valve was about 40% from static pressure of the pre-treated oil mixture before each valve.
- Pressure drops across each valve in the first homogenizer were 400, 240 and 145 psi.
- pressure drop across each homogenizing valve was about 30% from static pressure of the pre-treated oil mixture before each valve.
- Pressure drops across each valve in the second homogenizer were 65, 45 and 30 psi.
- the cavitation number C v for the pre-treated oil mixture across each homogenizing valve was 2.34, 2.40 and 2.44 and, accordingly, flow-induced cavitation was suppressed.
- the cavitation number C v for the pre-treated oil mixture across each homogenizing valve was 3.53, 3.72 and 3.73 and, accordingly, flow-induced cavitation was suppressed.
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Abstract
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BR112019024641B1 (pt) | 2017-05-24 | 2023-01-10 | Poet Research, Inc | Método para alterar uma ou mais propriedades do asfalto, composição de mistura de asfalto e composição de mistura de aglutinante de asfalto |
CN107557152B (zh) * | 2017-10-18 | 2020-12-22 | 宁夏君星坊食品科技有限公司 | 一种改进的连续亚麻油脱胶工艺 |
WO2019157334A1 (fr) | 2018-02-09 | 2019-08-15 | Poet Research, Inc. | Procédés de raffinage d'une composition d'huile de grains pour fabriquer un ou plusieurs produits d'huile de grains, et systèmes associés |
HUE060558T2 (hu) | 2018-06-11 | 2023-03-28 | Poet Res Inc | Eljárások gabonaolaj-készítmény nyersanyag finomítására és ezzel kapcsolatos rendszerek készítmények és alkalmazások |
US10808202B2 (en) | 2019-01-25 | 2020-10-20 | N.V. Desmet Ballestra Engineering S.A. | In line degumming and neutralization of oils and fats using hydrodynamic flow-through cavitation reactors |
EP4192964A1 (fr) | 2020-08-06 | 2023-06-14 | POET Research, Inc. | Lipase endogène pour la réduction de métaux dans l'huile de maïs de distillerie |
CN116445558B (zh) * | 2023-02-24 | 2024-06-07 | 江南大学 | 一种甘油二酯油的制备方法 |
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US6844458B2 (en) * | 1998-11-20 | 2005-01-18 | Ip Holdings, L.L.C. | Vegetable oil refining |
US6172248B1 (en) * | 1998-11-20 | 2001-01-09 | Ip Holdings, L.L.C. | Methods for refining vegetable oils and byproducts thereof |
CA2644085A1 (fr) * | 2006-03-01 | 2007-09-13 | Cargill, Incorporated | Procede de demucilagination d'huiles triglycerides |
WO2009148919A1 (fr) * | 2008-06-06 | 2009-12-10 | Cargill, Incorporated | Procédés de raffinage d’huile |
US8945644B2 (en) * | 2009-06-15 | 2015-02-03 | Cavitation Technologies, Inc. | Process to remove impurities from triacylglycerol oil |
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EP3292190B1 (fr) | 2020-08-19 |
EP3292190A4 (fr) | 2018-12-19 |
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