CN111849628A - Method for treating rice bran acidification oil - Google Patents
Method for treating rice bran acidification oil Download PDFInfo
- Publication number
- CN111849628A CN111849628A CN202010738848.XA CN202010738848A CN111849628A CN 111849628 A CN111849628 A CN 111849628A CN 202010738848 A CN202010738848 A CN 202010738848A CN 111849628 A CN111849628 A CN 111849628A
- Authority
- CN
- China
- Prior art keywords
- petroleum ether
- layer
- ethanol
- rice bran
- temperature
- 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.)
- Pending
Links
- 235000007164 Oryza sativa Nutrition 0.000 title claims abstract description 49
- 235000009566 rice Nutrition 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 23
- 230000020477 pH reduction Effects 0.000 title claims abstract description 6
- 240000007594 Oryza sativa Species 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 292
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 178
- 239000003208 petroleum Substances 0.000 claims abstract description 146
- 238000000605 extraction Methods 0.000 claims abstract description 62
- 241000209094 Oryza Species 0.000 claims abstract description 48
- GJJVAFUKOBZPCB-UHFFFAOYSA-N 2-methyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydrochromen-6-ol Chemical compound OC1=CC=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-UHFFFAOYSA-N 0.000 claims abstract description 47
- 229930003802 tocotrienol Natural products 0.000 claims abstract description 47
- 239000011731 tocotrienol Substances 0.000 claims abstract description 47
- 235000019148 tocotrienols Nutrition 0.000 claims abstract description 47
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical class COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 claims abstract description 43
- 239000000047 product Substances 0.000 claims abstract description 32
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 claims abstract description 29
- 229940114124 ferulic acid Drugs 0.000 claims abstract description 29
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 claims abstract description 29
- 235000001785 ferulic acid Nutrition 0.000 claims abstract description 29
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000000199 molecular distillation Methods 0.000 claims abstract description 28
- 239000012043 crude product Substances 0.000 claims abstract description 25
- 238000001914 filtration Methods 0.000 claims abstract description 23
- 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 abstract description 22
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 22
- 239000012141 concentrate Substances 0.000 claims abstract description 15
- 230000007062 hydrolysis Effects 0.000 claims abstract description 12
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229930003427 Vitamin E Natural products 0.000 claims abstract description 11
- 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 abstract description 11
- 235000019165 vitamin E Nutrition 0.000 claims abstract description 11
- 239000011709 vitamin E Substances 0.000 claims abstract description 11
- 229940046009 vitamin E Drugs 0.000 claims abstract description 11
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 6
- 238000002425 crystallisation Methods 0.000 claims abstract description 4
- 230000008025 crystallization Effects 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims abstract description 4
- 239000012535 impurity Substances 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 24
- 238000001816 cooling Methods 0.000 claims description 17
- 238000003756 stirring Methods 0.000 claims description 17
- 239000000706 filtrate Substances 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 229940114123 ferulate Drugs 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 229930182558 Sterol Natural products 0.000 claims description 7
- 239000012065 filter cake Substances 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 235000003702 sterols Nutrition 0.000 claims description 7
- 150000003432 sterols Chemical class 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 6
- 239000004327 boric acid Substances 0.000 claims description 6
- 239000012153 distilled water Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 238000009776 industrial production Methods 0.000 abstract description 5
- 239000000284 extract Substances 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 239000003921 oil Substances 0.000 description 38
- 235000019198 oils Nutrition 0.000 description 38
- 230000000052 comparative effect Effects 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 229930192734 Avilamycin Natural products 0.000 description 1
- 239000004190 Avilamycin Substances 0.000 description 1
- 235000019774 Rice Bran oil Nutrition 0.000 description 1
- XIRGHRXBGGPPKY-OTPQUNEMSA-N [(2r,3s,4r,6s)-6-[(2'r,3's,3ar,4r,4'r,6s,7ar)-6-[(2s,3r,4r,5s,6r)-2-[(2r,3s,4s,5s,6s)-6-[(2r,3as,3'ar,6'r,7r,7's,7ar,7'ar)-7'-acetyl-7'-hydroxy-6'-methyl-7-(2-methylpropanoyloxy)spiro[4,6,7,7a-tetrahydro-3ah-[1,3]dioxolo[4,5-c]pyran-2,4'-6,7a-dihydro-3ah- Chemical compound O([C@H]1[C@H](O)C[C@@H](O[C@@H]1C)O[C@H]1[C@H](O)CC2(O[C@]3(C)C[C@@H](O[C@H](C)[C@H]3O2)O[C@H]2[C@@H](OC)[C@@H](C)O[C@H]([C@@H]2O)O[C@H]2[C@H](O)[C@H](OC)[C@H](OC3[C@@H]([C@@H]4O[C@]5(O[C@H]4CO3)[C@@H]3OCO[C@H]3[C@@](O)([C@@H](C)O5)C(C)=O)OC(=O)C(C)C)O[C@@H]2COC)O[C@@H]1C)C(=O)C1=C(C)C(Cl)=C(O)C(Cl)=C1OC XIRGHRXBGGPPKY-OTPQUNEMSA-N 0.000 description 1
- 229960005185 avilamycin Drugs 0.000 description 1
- 235000019379 avilamycin Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 235000002378 plant sterols Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000008165 rice bran oil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
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
- C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- 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
- C11B3/006—Refining fats or fatty oils by extraction
-
- 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
- C11B3/12—Refining fats or fatty oils by distillation
-
- 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
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/08—Refining
- C11C1/10—Refining by distillation
-
- 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
- C11C1/10—Refining by distillation
- C11C1/103—Refining by distillation after or with the addition of chemicals
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for treating rice bran acidification oil, which comprises the following steps: (1) deacidifying rice bran acidification oil; (2) extracting to obtain an ethanol layer containing oryzanol; (3) extracting and back-extracting for many times to obtain a petroleum ether layer containing oryzanol; (4) distilling to obtain oryzanol crude product, hydrolyzing, and extracting to obtain three petroleum ether layers and ferulic acid salt layer for extracting ferulic acid; (5) performing cold separation, crystallization and filtration to obtain a crude product of the phytosterol and a tocotrienol concentrate; (6) quickly separating out, and filtering to obtain a refined phytosterol product; (7) carrying out molecular distillation on the tocotrienol concentrate to obtain ester impurities and vitamin E borate; (8) hydrolyzing vitamin E borate, and performing molecular distillation to obtain a refined tocotrienol product. The invention extracts the oryzanol from the acidified oil, and the product after the hydrolysis of the oryzanol is subjected to multiple extractions and molecular distillation to obtain high-purity refined phytosterol and refined tocotrienol, which can be continuously applied to industrial production.
Description
Technical Field
The invention relates to the technical field of residual oil treatment, in particular to a method for treating rice bran acidified oil.
Background
The rice bran acidified oil is low-price oil obtained by acidifying oil residue generated in the rice bran oil refining process, still contains low-content oryzanol, and can be further refined.
Because the rice bran acidified oil is waste liquid, the oryzanol content is low, the extraction difficulty is high, and most manufacturers choose to discard the rice bran acidified oil. Some manufacturers can adopt an extraction process to extract a oryzanol crude product from the rice bran acidified oil, so that the rice bran acidified oil is recycled.
The yield of the existing obtained crude oryzanol product is low and is only 30-50%, so that the oryzanol in the rice bran acidified oil is greatly lost, the oryzanol content is low, and the crude oryzanol product is difficult to be continuously applied to subsequent industrial production.
Disclosure of Invention
The invention aims to provide a comprehensive utilization method of rice bran acidified oil, which is used for extracting oryzanol from the rice bran acidified oil and further processing a oryzanol crude product into high-quality and high-value ferulic acid, tocotrienol and phytosterol.
A method for treating rice bran acidification oil comprises the following steps:
(1) deacidifying: adding water, ethanol and petroleum ether into the rice bran acidized oil, uniformly stirring, standing for layering to obtain a first petroleum ether layer on the upper layer and an alcohol layer on the lower layer, and extracting the alcohol layer with petroleum ether to obtain a petroleum ether layer and a first ethanol layer, wherein the petroleum ether layer is applied to the deacidification step of the next batch of materials;
(2) and (3) extraction: extracting the first ethanol layer by adopting petroleum ether to obtain an upper fatty acid-containing petroleum ether layer, adding ethanol and water into the first petroleum ether layer to perform primary extraction to obtain an upper petroleum ether layer, adding ethanol and water into the upper petroleum ether layer to perform secondary extraction, sleeving the lower ethanol layer on the first petroleum ether layer for extracting the lower batch, performing primary extraction on the first petroleum ether to obtain a lower alcohol layer, extracting the alcohol layer by using petroleum ether, and sleeving the obtained petroleum ether layer for the deacidification step, wherein the lower ethanol layer is a second ethanol layer;
(3) back extraction: extracting the second ethanol layer by adopting petroleum ether to obtain a third ethanol layer at the lower layer, and performing back extraction on the third ethanol layer by adopting petroleum ether for multiple times to obtain a second petroleum ether layer at the upper layer;
(4) removing the organic solvent: distilling the second petroleum ether layer, recovering petroleum ether to obtain a crude oryzanol product, hydrolyzing the crude oryzanol product under the condition of 0.2-0.5 Mpa, cooling to 20-40 ℃, and extracting by using petroleum ether to obtain a third petroleum ether layer at the upper layer and a ferulate layer at the lower layer;
(5) sterol extraction: cooling the third petroleum ether layer to 5-10 ℃, performing cold crystallization for 6-12 hours, filtering to obtain filtrate and a crude phytosterol product, and recovering the solvent from the filtrate to obtain a tocotrienol concentrate;
(6) sterol purification: adding petroleum ether into the crude phytosterol product, heating and stirring until the petroleum ether is completely dissolved, cooling, adding a mixture of ethanol and glycerol to quickly separate out the phytosterol, cooling, filtering and drying to obtain a refined phytosterol product;
(7) salt forming reaction and molecular distillation: carrying out first molecular distillation on the tocotrienol concentrate to obtain a tocotrienol crude product, adding boric acid into the tocotrienol crude product, stirring, reacting for 2-3 hours under a vacuum condition, then vacuumizing and dehydrating, and carrying out second molecular distillation to obtain light-phase ester impurities and heavy-phase vitamin E borate;
(8) hydrolysis reaction + molecular distillation: adding petroleum ether and distilled water into the vitamin E borate, carrying out hydrolysis reaction to obtain a fourth petroleum ether layer on the upper layer and a wastewater layer on the lower layer, vacuumizing the fourth petroleum ether layer to recover the petroleum ether and the water, and then carrying out third molecular distillation to obtain a light-phase tocotrienol refined product and heavy-phase residual oil.
The invention has the beneficial effects that: hydrolyzing the oryzanol crude product, and extracting and distilling the hydrolyzed product for multiple times to obtain high-purity refined phytosterol and refined tocotrienol, which can be continuously applied to industrial production.
In addition, the processing method of the rice bran acidified oil provided by the invention can also have the following additional technical characteristics:
further, in the step (1), the mass ratio of the rice bran acidified oil to the water to the ethanol to the petroleum ether is 10: 2-3: 1-3: 5-35, the temperature for uniformly stirring is 5-25 ℃, the pH is adjusted to 7.5-8, the petroleum ether is adopted for re-extraction, and the ratio of the petroleum ether to the rice bran acidified oil is 10: 5-20.
Further, in the step (2), before the first ethanol layer is extracted by using petroleum ether, the pH is adjusted to 6.5-7, the extraction temperature is 5-25 ℃, the lower ethanol layer is extracted by using petroleum ether, and the ratio of the petroleum ether to the rice bran acidified oil is 10: 5-20: 10, adding ethanol and water into the first petroleum ether layer for first extraction, wherein the extraction temperature is 5-20 ℃, the pH is 10.5-12.5, the ratio of the ethanol to the water to the acidified oil is 30-50: 1-2: 10, so as to obtain an upper petroleum ether layer, adding ethanol and water into the upper petroleum ether layer for second extraction, so as to obtain a first petroleum ether layer, wherein the lower ethanol layer is used for the extraction step of the next batch, and the ratio of the ethanol to the water to the acidified oil of rice bran is 30-50: 1-2: 10, and the pH is controlled to be 12-13.
Further, in the step (3), the amount of petroleum ether extracted by the second ethanol layer is the same as the amount of petroleum ether extracted in the step (1), in the step (3), the third ethanol layer is subjected to back extraction for 5 times, the back extraction temperature is 5-25 ℃, and the petroleum ether amount of the back extraction for 1-5 times is 40%, 30%, 10% of the petroleum ether amount extracted by the second ethanol layer.
Further, the method further comprises:
in the step (4), the hydrolysis pressure of the crude oryzanol is controlled by the hydrolysis temperature, the temperature is controlled to be 90-110 ℃, the corresponding pressure is 0.2-0.5 Mpa, the hydrolysis time is 5-8 hours, the ferulate layer in the step (4) is subjected to normal pressure distillation, alcohols are recovered, and a ferulate aqueous solution is obtained; the boiling range of petroleum ether is 60-90 ℃;
and adjusting the pH value of the ferulic acid aqueous solution to 4-5, standing for 3-5 hours at the temperature of 10-15 ℃, and filtering to obtain a ferulic acid crude product.
Further, the method further comprises:
adding pure water with the mass 5-8 times and active carbon with the mass 0.003-0.005 time into the ferulic acid crude product, heating to 70-80 ℃, reacting for 0.5-1 hour, filtering while hot, cooling the obtained filtrate to 30-40 ℃, adding 5-10% pure water with the temperature 5-10 ℃, stirring, standing, filtering, and drying the obtained filter cake to obtain the ferulic acid refined product.
Further, the temperature of the first molecular distillation is 240-280 ℃, the pressure is 1-10 pa, the temperature of the second molecular distillation is 280-300 ℃, the pressure is 1-10 pa, and the temperature of the third molecular distillation is 230-280 ℃, and the pressure is 1-10 pa.
Further, the adding amount of the petroleum ether in the step (6) is 3-10 times of the mass of the crude phytosterol, the mixture is heated and stirred to 70-80 ℃, the concentration of the added ethanol is 95%, the temperature is 5-15 ℃, the adding amount is 0.1-0.2 time of the mass of the crude phytosterol, the concentration of the added glycerol is 99%, and the temperature is 5-15 ℃.
Further, in the step (7), the adding amount of the boric acid is 2-3% of the mass of the crude tocotrienol product, the vacuum condition is 300-600 pa, and the temperature is 130-140 ℃.
Further, in the step (8), the adding amount of petroleum ether and distilled water is 1 time and 0.5 time of the volume of the vitamin E borate respectively, the hydrolysis reaction temperature is 80-90 ℃, and the reaction time is 2-3 hours.
Additional aspects and advantages of the invention will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the invention.
Drawings
The above and/or additional aspects and advantages of the present invention will become apparent and readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawings of which:
FIG. 1 is a flow chart of the extraction of a tocotrienol extract according to example 1 of the present invention;
FIG. 2 is a flow chart of the process for extracting a refined plant sterol according to example 1 of the present invention.
Detailed Description
In order to make the objects, features and advantages of the present invention comprehensible, embodiments accompanied with figures are described in detail below. Several embodiments of the invention are presented in the drawings. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Example 1
Referring to fig. 1 and 2, a method for treating rice bran sulfated oil comprises the following steps:
(1) deacidifying: adding water, ethanol and petroleum ether into the rice bran acidized oil, uniformly stirring, standing for layering to obtain a first petroleum ether layer on the upper layer and an alcohol layer on the lower layer, and extracting the alcohol layer with petroleum ether to obtain a petroleum ether layer and a first ethanol layer, wherein the petroleum ether layer is applied to the deacidification step of the next batch of materials;
(2) and (3) extraction: extracting the first ethanol layer by adopting petroleum ether to obtain an upper fatty acid-containing petroleum ether layer, adding ethanol and water into the first petroleum ether layer to perform primary extraction to obtain an upper petroleum ether layer, adding ethanol and water into the upper petroleum ether layer to perform secondary extraction, sleeving the lower ethanol layer on the first petroleum ether layer for extracting the lower batch, performing primary extraction on the first petroleum ether to obtain a lower alcohol layer, extracting the alcohol layer by using petroleum ether, sleeving the obtained petroleum ether layer for the deacidification step, and using the lower ethanol layer as a second lower ethanol layer;
(3) back extraction: extracting the second ethanol layer by adopting petroleum ether to obtain a third ethanol layer at the lower layer, and performing back extraction on the third ethanol layer by adopting petroleum ether for multiple times to obtain a second petroleum ether layer at the upper layer;
(4) removing the organic solvent: distilling the second petroleum ether layer, recovering petroleum ether to obtain a crude oryzanol product, hydrolyzing the crude oryzanol product under the condition of 0.3Mpa, cooling to 30 ℃, and extracting by using petroleum ether to obtain a third petroleum ether layer at the upper layer and a ferulate layer at the lower layer;
(5) sterol extraction: cooling the third petroleum ether layer to 8 ℃, performing cold separation and crystallization for 9 hours, filtering to obtain filtrate and a crude phytosterol product, and recovering the solvent from the filtrate to obtain a tocotrienol concentrate;
(6) sterol purification: adding petroleum ether into the crude phytosterol product, heating and stirring until the petroleum ether is completely dissolved, cooling, adding a mixture of ethanol and glycerol to quickly separate out the phytosterol, cooling and filtering to obtain a refined phytosterol product in a filter cake state;
(7) salt forming reaction and molecular distillation: carrying out first molecular distillation on the tocotrienol concentrate to obtain a tocotrienol crude product, adding boric acid into the tocotrienol crude product, stirring, reacting for 2.5 hours under a vacuum condition, vacuumizing, dehydrating, and carrying out second molecular distillation to obtain light-phase ester impurities and heavy-phase vitamin E borate;
(8) hydrolysis reaction + molecular distillation: adding petroleum ether and distilled water into the vitamin E borate, carrying out hydrolysis reaction to obtain a fourth petroleum ether layer on the upper layer and a wastewater layer on the lower layer, vacuumizing the fourth petroleum ether layer to recover the petroleum ether and the water, and then carrying out third molecular distillation to obtain a light-phase tocotrienol refined product and heavy-phase residual oil. In this embodiment, the oryzanol crude product is hydrolyzed, and the hydrolyzed product is subjected to multiple extractions, back extractions and molecular distillation to obtain a high-purity refined phytosterol and refined tocotrienol, which can be continuously applied to industrial production.
Specifically, the hydrolysis is carried out under the condition of 0.3Mpa, and alcohols with 5 times of the volume of the oryzanol crude product are adopted, wherein the alcohols are ethanol, in other embodiments, the alcohols can also be n-butanol or isopropanol, methanol cannot be selected, and the methanol is easy to react with materials in the hydrolysis process due to low molecular weight.
In this embodiment, the pressure of the hydrolysis reaction is adjusted by temperature, that is, under a closed condition, the pressure of the environment can be changed by changing the temperature of the environment, when the temperature is 110 ℃, the system pressure is 0.5Mpa, the system pressure is 0.35Mpa at 100 ℃, and the system pressure is 0.25Mpa at 90 ℃, the pressure change is realized without repeatedly injecting gas or extracting gas; in addition, the temperature and the pressure can be adjusted simultaneously, namely, the temperature can be adjusted once without respectively adjusting the temperature and the pressure.
In this embodiment, in step (1), the rice bran acidified oil contains 5% of oryzanol and 0.5% of tocotrienol, the acid value is 116mg KOH/g, the mass ratio of the rice bran acidified oil to water to ethanol to petroleum ether is 10:2:2:10, the temperature for uniformly stirring is 15 ℃, the PH is adjusted to 8, in step (2), before the first ethanol layer is extracted by using petroleum ether, the PH is adjusted to 7, the extraction temperature is 25 ℃, the extraction temperature is 15 ℃, the lower ethanol layer is extracted by using petroleum ether, and the ratio of the petroleum ether to the rice bran acidified oil is 10:15: 10; adding ethanol and water into the first petroleum ether layer for first extraction, wherein the extraction temperature is 15 ℃, the pH value is 11, the ratio of the ethanol to the water to the acidified oil is 40:1.5:10 to obtain an upper petroleum ether layer, adding the ethanol to the upper petroleum ether layer and the water to perform secondary extraction to obtain a lower ethanol layer which is sleeved on the first petroleum ether layer used for the extraction step of the next batch, wherein the ratio of the ethanol to the water to the acidified oil of rice bran is 40:1.5:10, and the pH value is controlled to be 12.
Specifically, the petroleum ether used in the step (3) is the same as the petroleum ether used in the step (1), the third ethanol layer is subjected to back extraction for 5 times in the step (3), the back extraction temperature is 15 ℃, and the petroleum ether used in the back extraction for 1-5 times is 40%, 30%, 10%, respectively.
In addition, the temperature of the first molecular distillation is 260 ℃ and the pressure is 5pa, the temperature of the second molecular distillation is 290 ℃ and the pressure is 5pa, and the temperature of the third molecular distillation is 200 ℃ and the pressure is 5 pa.
In the step (4), the obtained crude oryzanol product has the content of 48 percent, the acid value of 45mg KOH/g and the content of tocotrienol of 4.8 percent.
In the step (5), the content of crude sterol is 42%, and the content of tocotrienol in the obtained tocotrienol concentrate is 11.0%.
Specifically, the adding amount of the petroleum ether in the step (6) is 7 times of the mass of the crude phytosterol, the mixture is heated and stirred to 75 ℃, the concentration of the added ethanol is 95%, the temperature is 10 ℃, the adding amount of the petroleum ether is 0.1 time of the mass of the crude phytosterol, the concentration of the added glycerol is 99%, and the temperature is 5-15 ℃.
In addition, in the step (7), the adding amount of the boric acid is 2% of the mass of the crude tocotrienol, the vacuum condition is 300pa, the temperature is 130 ℃, and the content of tocotrienol in the crude tocotrienol is 18.0%.
In addition, in the step (8), the addition amounts of petroleum ether and distilled water are respectively 1 time and 0.5 time of the volume of the vitamin E borate, the hydrolysis reaction temperature is 80 ℃, and the reaction time is 2 hours.
The pH adjustment was carried out using 25% sodium hydroxide solution and 50% dilute sulfuric acid.
Example 2
This embodiment is substantially the same as embodiment 1 except that:
in the step (1), the rice bran acidified oil contains 7% of oryzanol, 0.6% of tocotrienol and 123mg KOH/g of acid value, and the mass ratio of the rice bran acidified oil to the water to the ethanol to the petroleum ether is 10:3:3: 35.
In the step (5), the content of tocotrienol in the obtained tocotrienol concentrate is 13.2%.
Example 3
This embodiment is substantially the same as embodiment 1 except that:
in the step (1), the rice bran acidified oil contains 8% of oryzanol and 0.5% of tocotrienol, and the acid value is 135mg KOH/g;
in the step (5), the content of tocotrienol in the obtained tocotrienol concentrate is 11.5%.
Example 4
This embodiment is substantially the same as embodiment 3 except that:
in the step (1), the rice bran acidified oil contains 9% of oryzanol and 0.4% of tocotrienol, and the acid value is 115mg KOH/g;
in the step (4), the hydrolysis pressure of the crude oryzanol is controlled by the hydrolysis temperature, the temperature is controlled at 100 ℃, the corresponding pressure is 0.3Mpa, the hydrolysis time is 7 hours, the normal pressure distillation is carried out on the ferulate layer in the step (4), and alcohols are recovered to obtain the aqueous solution of ferulate;
adjusting the pH value of the ferulic acid aqueous solution to 4, standing for 4 hours at the temperature of 10 ℃, and filtering to obtain a ferulic acid crude product.
In the step (5), the content of tocotrienol in the obtained tocotrienol concentrate is 8.5%.
Adding pure water 7 times the mass of the ferulic acid crude product and active carbon 0.004 times the mass of the ferulic acid crude product, heating to 75 ℃, reacting for 1 hour, filtering while hot, cooling the obtained filtrate to 35 ℃, adding a 5% ethanol and 25% ethanol mixed solution at 5 ℃, stirring, standing, filtering, and drying the obtained filter cake to obtain the ferulic acid refined product.
It can be understood that, in this embodiment, while the refined phytosterol and the refined tocotrienol are extracted, the refined ferulic acid can be obtained through preparation, extraction and purification, and the industrial utilization value is improved.
Example 5
This embodiment is substantially the same as embodiment 3 except that:
in the step (1), the rice bran acidified oil contains 3.8% of oryzanol and 0.4% of tocotrienol, and the acid value is 122mg KOH/g;
distilling the ferulic acid salt layer in the step (4) at normal pressure, and recovering alcohols to obtain a ferulic acid salt aqueous solution;
adjusting the pH value of the ferulic acid aqueous solution to 5, standing for 5 hours at the temperature of 15 ℃, and filtering to obtain a ferulic acid crude product.
Adding 8 times of pure water and 0.005 time of activated carbon into the ferulic acid crude product, heating to 80 ℃, reacting for 1 hour, filtering while hot, cooling the obtained filtrate to 40 ℃, adding 10% ethanol and 30% ethanol mixed solution at 10 ℃, stirring, standing, filtering, and drying the obtained filter cake to obtain the ferulic acid refined product.
In the step (5), the content of tocotrienol in the obtained tocotrienol concentrate is 8.5%.
Example 6
This embodiment is substantially the same as embodiment 3 except that: distilling the ferulic acid salt layer in the step (4) at normal pressure, and recovering alcohols to obtain a ferulic acid salt aqueous solution;
adjusting the pH value of the ferulic acid aqueous solution to 4, standing for 3 hours at the temperature of 10 ℃, and filtering to obtain a ferulic acid crude product.
Adding pure water with the mass 5 times and active carbon with the mass 0.003 times of the mass of the ferulic acid crude product into the ferulic acid crude product, heating to 70 ℃, reacting for 0.5 hour, filtering while hot, cooling the obtained filtrate to 30 ℃, adding a 5% ethanol and 20% ethanol mixed solution with the temperature 5 ℃, stirring, standing, filtering, and drying the obtained filter cake to obtain the ferulic acid refined product.
In the step (5), the content of tocotrienol in the obtained tocotrienol concentrate is 11.5%.
Comparative example 1
This comparative example 1 was substantially the same as example 4 except that:
the petroleum ether used in the step (3) and the petroleum ether used in the step (1) are used in the same amount, and the third ethanol layer is subjected to back extraction for 1 time in the step (3), wherein the back extraction temperature is 15 ℃.
Comparative example 2
This comparative example is substantially the same as example 4 except that:
the petroleum ether used in the step (3) is the same as the petroleum ether used in the step (1), the third ethanol layer is subjected to back extraction for 3 times in the step (3), the back extraction temperature is 15 ℃, and the petroleum ether used in the back extraction for 1-3 times is 70%, 20% and 10% respectively.
Comparative example 3
This comparative example is substantially the same as example 4 except that:
the concentration of the glycerol in the step (6) is 60%.
Comparative example 4
This comparative example is substantially the same as example 4 except that:
in the step (1) of the comparative example, the petroleum ether layer is not used for the deacidification of the next batch of materials, the lower ethanol layer is not used for the extraction of the first petroleum ether layer in the step (2), and the obtained petroleum ether layer is not used for the deacidification.
To further illustrate the present invention, 1000kg of rice bran acidified oil is extracted by the methods of the above examples and comparative examples, according to the relative molecular mass of oryzanol of 602.8861, the relative molecular mass of avilamycin of 194.18, the theoretical yield of ferulic acid of 32.21%, and the calculation formula of the yield of ferulic acid is: the content of fine ferulic acid/the mass of rice bran acidified oil/the content of oryzanol in rice bran acidified oil/32.21%, and the results obtained by purification are shown in table 1.
TABLE 1
As can be seen from Table 1, examples 1 to 6 all achieve good purification effect, the net content is more than 80%, the oryzanol can be applied to industrial production, the yield of oryzanol is high, and in addition, high-purity ferulic acid is obtained in example 4;
as can be seen from comparative examples 1 and 2, when the number of back extractions is less than 5, the yield of oryzanol is low;
as can be seen from comparative example 3, the concentration of glycerol significantly affected the content of the phytosterol concentrate;
as can be seen from comparative example 4, the yield of oryzanol was significantly reduced when the use of the formulation was not performed.
In the description herein, references to the description of the term "one embodiment," "some embodiments," "an example," "a specific example," or "some examples," etc., mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (10)
1. A method for treating rice bran acidification oil is characterized by comprising the following steps:
(1) deacidifying: adding water, ethanol and petroleum ether into the rice bran acidized oil, uniformly stirring, standing for layering to obtain a first petroleum ether layer on the upper layer and an alcohol layer on the lower layer, and extracting the alcohol layer with petroleum ether to obtain a petroleum ether layer and a first ethanol layer, wherein the petroleum ether layer is applied to the deacidification step of the next batch of materials;
(2) and (3) extraction: extracting the first ethanol layer by adopting petroleum ether to obtain an upper fatty acid-containing petroleum ether layer, adding ethanol and water into the first petroleum ether layer to perform primary extraction to obtain an upper petroleum ether layer, adding ethanol and water into the upper petroleum ether layer to perform secondary extraction, sleeving the lower ethanol layer on the first petroleum ether layer for extracting the lower batch, performing primary extraction on the first petroleum ether to obtain a lower alcohol layer, extracting the alcohol layer by using petroleum ether, sleeving the obtained petroleum ether layer for the deacidification step, and using the lower ethanol layer as a second lower ethanol layer;
(3) back extraction: extracting the second ethanol layer by adopting petroleum ether to obtain a third ethanol layer at the lower layer, and performing back extraction on the third ethanol layer by adopting petroleum ether for multiple times to obtain a second petroleum ether layer at the upper layer;
(4) removing the organic solvent: distilling the second petroleum ether layer, recovering petroleum ether to obtain a crude oryzanol product, hydrolyzing the crude oryzanol product under the condition of 0.2-0.5 Mpa, cooling to 20-40 ℃, and extracting by using petroleum ether to obtain a third petroleum ether layer at the upper layer and a ferulate layer at the lower layer;
(5) sterol extraction: cooling the third petroleum ether layer to 5-10 ℃, performing cold crystallization for 6-12 hours, filtering to obtain filtrate and a crude phytosterol product, and recovering the solvent from the filtrate to obtain a tocotrienol concentrate;
(6) sterol purification: adding petroleum ether into the crude phytosterol product, heating and stirring until the petroleum ether is completely dissolved, cooling, adding a mixture of ethanol and glycerol to quickly separate out the phytosterol, cooling and filtering to obtain a refined phytosterol product in a filter cake state;
(7) salt forming reaction and molecular distillation: carrying out first molecular distillation on the tocotrienol concentrate to obtain a tocotrienol crude product, adding boric acid into the tocotrienol crude product, stirring, reacting for 2-3 hours under a vacuum condition, then vacuumizing and dehydrating, and carrying out second molecular distillation to obtain light-phase ester impurities and heavy-phase vitamin E borate;
(8) hydrolysis reaction + molecular distillation: and adding petroleum ether and distilled water into the vitamin E borate, carrying out hydrolysis reaction to obtain a fourth petroleum ether layer on the upper layer and a water layer on the lower layer, vacuumizing the fourth petroleum ether layer to recover the petroleum ether and the water, and then carrying out third molecular distillation to obtain a light-phase tocotrienol refined product and heavy-phase residual oil.
2. The method for treating rice bran acidified oil as claimed in claim 1, wherein in the step (1), the mass ratio of the rice bran acidified oil to the water to the ethanol to the petroleum ether is 10: 2-3: 1-3: 5-35, the temperature for uniformly stirring is 5-25 ℃, the pH is adjusted to 7.5-8, and the re-extraction is performed by using the petroleum ether, wherein the ratio of the petroleum ether to the rice bran acidified oil is 10: 5-20.
3. The method for treating rice bran acidified oil as claimed in claim 1, wherein in the step (2), before the first ethanol layer is extracted with petroleum ether, the PH is adjusted to 6.5-7, the extraction temperature is 5-25 ℃, the lower ethanol layer is extracted with petroleum ether, and the ratio of petroleum ether to rice bran acidified oil is 10: 5-20: 10, adding ethanol and water into the first petroleum ether layer for first extraction, wherein the extraction temperature is 5-20 ℃, the pH is 10.5-12.5, the ratio of the ethanol to the water to the acidified oil is 30-50: 1-2: 10, so as to obtain an upper petroleum ether layer, adding ethanol and water into the upper petroleum ether layer for second extraction, so as to obtain a first petroleum ether layer, wherein the lower ethanol layer is used for the extraction step of the next batch, and the ratio of the ethanol to the water to the acidified oil of rice bran is 30-50: 1-2: 10, and the pH is controlled to be 12-13.
4. The method for treating rice bran acidified oil according to claim 1, wherein the amount of petroleum ether extracted by petroleum ether in the second ethanol layer in the step (3) is the same as the amount of petroleum ether used in the step (1), the third ethanol layer is subjected to 5 times of back extraction in the step (3), the back extraction temperature is 5-25 ℃, and the amount of petroleum ether used in the 1-5 times of back extraction is 40%, 30%, 10% of the amount of petroleum ether extracted by petroleum ether in the second ethanol layer.
5. The rice bran acidified oil treatment method of claim 1, further comprising:
in the step (4), the hydrolysis pressure of the crude oryzanol is controlled by the hydrolysis temperature, the temperature is controlled to be 90-110 ℃, the corresponding pressure is 0.2-0.5 Mpa, the hydrolysis time is 5-8 hours, the ferulate layer in the step (4) is subjected to atmospheric distillation, alcohols, petroleum ether and low-boiling-point substances are recovered, and the aqueous solution of ferulate is obtained; the boiling range of petroleum ether is 60-90 ℃;
and adjusting the pH value of the ferulic acid aqueous solution to 4-5, standing for 3-5 hours at the temperature of 10-15 ℃, and filtering to obtain a ferulic acid crude product.
6. The rice bran acidified oil treatment method of claim 5, further comprising:
adding pure water with the mass 5-8 times and active carbon with the mass 0.003-0.005 time into the ferulic acid crude product, heating to 70-80 ℃, reacting for 0.5-1 hour, filtering while hot, cooling the obtained filtrate to 30-40 ℃, adding 5-10% pure water with the temperature 5-10 ℃, stirring, standing, filtering, and drying the obtained filter cake to obtain the ferulic acid refined product.
7. The method for treating rice bran acidified oil according to claim 1, wherein the temperature of the first molecular distillation is 240-280 ℃ and the pressure is 1-10 pa, the temperature of the second molecular distillation is 280-300 ℃ and the pressure is 1-10 pa, and the temperature of the third molecular distillation is 230-280 ℃ and the pressure is 1-10 pa.
8. The method for treating rice bran acidified oil according to claim 1, wherein the petroleum ether is added in the step (6) in an amount of 3 to 10 times the mass of the crude phytosterol, the mixture is heated and stirred to 70 to 80 ℃, the concentration of the added ethanol is 95% and the temperature is 5 to 15 ℃, the addition amount of the added ethanol is 0.1 to 0.2 times the mass of the crude phytosterol, and the concentration of the added glycerol is 99% and the temperature is 5 to 15 ℃.
9. The method for treating rice bran acidified oil as claimed in claim 1, wherein in the step (7), the amount of boric acid added is 2-3% of the crude tocotrienol, the vacuum condition is 300-600 pa, and the temperature is 130-140 ℃.
10. The method for treating rice bran acidified oil as claimed in claim 1, wherein in the step (8), the petroleum ether and distilled water are added in an amount of 1 time and 0.5 time of the volume of the vitamin E borate, the hydrolysis reaction temperature is 80-90 ℃, and the reaction time is 2-3 h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010738848.XA CN111849628A (en) | 2020-07-28 | 2020-07-28 | Method for treating rice bran acidification oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010738848.XA CN111849628A (en) | 2020-07-28 | 2020-07-28 | Method for treating rice bran acidification oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111849628A true CN111849628A (en) | 2020-10-30 |
Family
ID=72948129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010738848.XA Pending CN111849628A (en) | 2020-07-28 | 2020-07-28 | Method for treating rice bran acidification oil |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111849628A (en) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1008767A (en) * | 1961-06-01 | 1965-11-03 | Eastman Kodak Co | Improvements in or relating to sterols and tocopherols |
| CN1093698A (en) * | 1993-12-20 | 1994-10-19 | 蔡克忠 | A kind of method for preparing forulic acid, Sodium Ferulate, sterol from ferulic acid ester |
| CN101255344A (en) * | 2007-03-02 | 2008-09-03 | 中国农业科学院油料作物研究所 | Method for co-production of bio-diesel and vitamin E, phytosterol by using plant oil |
| CN101984028A (en) * | 2010-10-29 | 2011-03-09 | 湖南农业大学 | High-oryzanol rice bran oil two-phase extraction de-acidification refining technology |
| CN103435677A (en) * | 2013-08-24 | 2013-12-11 | 浙江得乐康食品股份有限公司 | Novel method for extracting oryzanol from crude rice bran oil |
| CN105585553A (en) * | 2014-11-18 | 2016-05-18 | 陕西秦岭生物工程有限公司 | Natural tocopherol extract method |
| CN111393400A (en) * | 2020-04-23 | 2020-07-10 | 湖南华诚生物资源股份有限公司 | Method for preparing squalene, vitamin E and sterol from fructus momordicae seed kernels |
-
2020
- 2020-07-28 CN CN202010738848.XA patent/CN111849628A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1008767A (en) * | 1961-06-01 | 1965-11-03 | Eastman Kodak Co | Improvements in or relating to sterols and tocopherols |
| CN1093698A (en) * | 1993-12-20 | 1994-10-19 | 蔡克忠 | A kind of method for preparing forulic acid, Sodium Ferulate, sterol from ferulic acid ester |
| CN101255344A (en) * | 2007-03-02 | 2008-09-03 | 中国农业科学院油料作物研究所 | Method for co-production of bio-diesel and vitamin E, phytosterol by using plant oil |
| CN101984028A (en) * | 2010-10-29 | 2011-03-09 | 湖南农业大学 | High-oryzanol rice bran oil two-phase extraction de-acidification refining technology |
| CN103435677A (en) * | 2013-08-24 | 2013-12-11 | 浙江得乐康食品股份有限公司 | Novel method for extracting oryzanol from crude rice bran oil |
| CN105585553A (en) * | 2014-11-18 | 2016-05-18 | 陕西秦岭生物工程有限公司 | Natural tocopherol extract method |
| CN111393400A (en) * | 2020-04-23 | 2020-07-10 | 湖南华诚生物资源股份有限公司 | Method for preparing squalene, vitamin E and sterol from fructus momordicae seed kernels |
Non-Patent Citations (3)
| Title |
|---|
| 池永红等: "《发酵工程设备》", 31 December 2014, 重庆大学出版社 * |
| 邵国武等: "高谷维素米糠油双相萃取脱酸精炼工艺研究", 《粮食科技与经济》 * |
| 陈星等: "分子蒸馏法从大豆油脚中提取维生素E的研究", 《粮食加工》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103588837B (en) | Tylosin tartrate or Webel Tylan Premix is extracted from anti-stripping agent | |
| CN111171103B (en) | Method for extracting oryzanol by multiple solvents | |
| WO2009036674A1 (en) | A method for recovering sulfuric acid from concentrated acid hydrolyzate of plant cellulose material | |
| CN107337593B (en) | Preparation method of coenzyme Q10 pure product | |
| CN107446966A (en) | A kind of preparation method of D pantolactones | |
| CN105669879A (en) | Preparation method of xylooligosaccharide | |
| CN109369389A (en) | The preparation process of high-purity alpha-linolenic acid ethyl ester | |
| CN105037473A (en) | Purification and refining method of sterol from tall oil | |
| CN110791376B (en) | Supercritical CO 2 Method for removing free fatty acid in camellia seed oil by microemulsion | |
| CN102329221B (en) | Method for preparing isostearic acid | |
| CN111849628A (en) | Method for treating rice bran acidification oil | |
| CN110819444A (en) | Method for extracting tea oil and tea saponin from camellia seeds | |
| CN108976270B (en) | Preparation method of high-purity doramectin | |
| CN107759467B (en) | Preparation method for improving carnosic acid content in rosemary lipid-soluble antioxidant | |
| CN109485559A (en) | A method of extracting shikimic acid from illiciumverum | |
| CN102633642B (en) | Method for preparing pleuromutilin crystal | |
| CN108164398A (en) | A kind of improved method of hydroxytyrosol synthesis technology | |
| US20230219872A1 (en) | Industrial extraction method of cannabidiol | |
| CN101417917A (en) | Method for preparing high-purity all-trans lycopene crystal | |
| CN106431895A (en) | Method for extracting lactic acid from fermentation liquor through combination of molecular distillation and extraction | |
| CN113912480A (en) | Extraction method of coenzyme Q10 | |
| CN110862427B (en) | Purification method of gentamicin C1a | |
| WO2009065504A1 (en) | Preparation of alcohols from a biomass by means of in situ distillation | |
| CN104557515A (en) | Method for extracting and separating L-lactic acid from ammonium lactate fermentation material liquid | |
| CN108424352B (en) | Refining method of biodiesel byproduct glycerol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20201030 |
|
| RJ01 | Rejection of invention patent application after publication |