CN111411018A - Method for converting fatty acid into fatty acid ethyl ester - Google Patents
Method for converting fatty acid into fatty acid ethyl ester Download PDFInfo
- Publication number
- CN111411018A CN111411018A CN202010205258.0A CN202010205258A CN111411018A CN 111411018 A CN111411018 A CN 111411018A CN 202010205258 A CN202010205258 A CN 202010205258A CN 111411018 A CN111411018 A CN 111411018A
- Authority
- CN
- China
- Prior art keywords
- fatty acid
- rice bran
- oil
- conducting
- ethyl ester
- 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
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 38
- 239000000194 fatty acid Substances 0.000 title claims abstract description 38
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 38
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims abstract description 14
- 235000019774 Rice Bran oil Nutrition 0.000 claims abstract description 24
- 239000008165 rice bran oil Substances 0.000 claims abstract description 24
- 241000209094 Oryza Species 0.000 claims abstract description 14
- 235000007164 Oryza sativa Nutrition 0.000 claims abstract description 14
- 235000009566 rice Nutrition 0.000 claims abstract description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000001914 filtration Methods 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 239000005995 Aluminium silicate Substances 0.000 claims description 10
- 235000012211 aluminium silicate Nutrition 0.000 claims description 10
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 10
- 238000000605 extraction Methods 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000012065 filter cake Substances 0.000 claims description 3
- 239000003921 oil Substances 0.000 abstract description 10
- 235000019198 oils Nutrition 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 5
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract description 4
- 239000000796 flavoring agent Substances 0.000 abstract description 3
- 235000019634 flavors Nutrition 0.000 abstract description 3
- 201000001320 Atherosclerosis Diseases 0.000 abstract description 2
- 239000008280 blood Substances 0.000 abstract description 2
- 210000004369 blood Anatomy 0.000 abstract description 2
- FMMOOAYVCKXGMF-MURFETPASA-N ethyl linoleate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC FMMOOAYVCKXGMF-MURFETPASA-N 0.000 abstract description 2
- 229940031016 ethyl linoleate Drugs 0.000 abstract description 2
- 239000003205 fragrance Substances 0.000 abstract description 2
- FMMOOAYVCKXGMF-UHFFFAOYSA-N linoleic acid ethyl ester Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCC FMMOOAYVCKXGMF-UHFFFAOYSA-N 0.000 abstract description 2
- 230000001105 regulatory effect Effects 0.000 abstract description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- -1 fatty acid ester Chemical class 0.000 description 3
- 239000004519 grease Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 108090001060 Lipase Proteins 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- 102000004882 Lipase Human genes 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 235000019421 lipase Nutrition 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 108010084311 Novozyme 435 Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000009874 alkali refining Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001007 puffing effect Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
-
- 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
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
- C11B1/108—Production of fats or fatty oils from raw materials by extracting after-treatment, e.g. of miscellae
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for converting fatty acid into fatty acid ethyl ester, belongs to the technical processing field of oil, and solves the problem of low oil yield of the existing method for reducing fatty acid in rice bran. The rice bran oil has weaker fragrance after main fatty acid in the rice bran oil is converted into fatty acid ethyl ester, and the flavor of the rice bran oil can be improved. The ethyl linoleate has effects of regulating blood cholesterol, preventing and treating atherosclerosis, and resisting variation.
Description
Technical Field
The invention belongs to the technical field of grease processing, and particularly relates to a method for converting fatty acid into fatty acid ethyl ester.
Background
Crude rice bran oil extracted from rice bran contains a certain amount of fatty acids, which are caused by decomposition of the rice bran oil into fatty acids by lipase in rice bran after processing rice or millet. The longer the processed rice bran is stored, the more fatty acids are present. The normal eating of people is affected when the content of the fatty acid exceeds a certain range. In order to reduce the generation of fatty acid in rice bran, the lipase is generally inactivated by puffing fresh rice bran, so that the acid value of the rice bran crude oil can be greatly reduced. The crude rice bran oil acid value is usually 10-20 (mg/g), and the crude rice bran oil can be sold in the market only after deacidification treatment to make the acid value lower than 3 (mg/g). The conventional alkali refining neutralization deacidification method can generate a large amount of waste water, and can also cause hydrolysis of a part of grease in the refining process, thereby reducing the yield of refined oil. Zengqing enzyme and the like (journal of agricultural engineering, 2009,25(8): 215-219) adopt zinc oxide as a catalyst and a method for deacidifying glycerol and fatty acid ester to reduce the acid value from 38.14mg/g to 5.17 mg/g. CN10983713 adopts a method of catalyzing by Novozym435, ultrasonic assisting and deacidifying by glycerol and fatty acid ester, the acid value of the method is reduced from 27.6mg/g to 1.4mg/g, the effect is better, and the industrial cost needs to be considered. Kale V. et al (J.Am.oil.chem.Soc.,1999,76(6):723-777) used methanol to perform two-time extraction deacidification on high acid value rice bran oil, and the fatty acid content in the rice bran oil was reduced from 16.5% to 0.33%. The Huxian et al (Chinese food and oil science, 2013,28(8): 33-36.) studied the deacidification effect of rice bran oil by using 95% edible ethanol as an extractant, and after two times of extraction, the acid value of the rice bran oil is reduced from 18.9mg/g to 1.21mg/g, thus obtaining better effect. The disadvantage is that the yield of the grease is low.
Disclosure of Invention
Aiming at the problem of low oil yield of the conventional method for reducing fatty acid in rice bran, the invention provides a method for converting fatty acid into fatty acid ethyl ester, which is simple to operate, high in yield and low in cost.
The invention is supported by the scientific and technological achievements of high schools in Shanxi province and the like.
Kaolin contains a large amount of alumina and silicon oxide, a small amount of iron oxide and titanium oxide, and trace elements such as sodium, potassium, calcium, magnesium and the like, has physicochemical properties such as high whiteness, soft texture, easy dispersion and suspension in water, good adsorbability, chemical stability and the like, and can also be used for preparing catalysts with different characteristics.
In order to reduce fatty acid in rice bran oil, the invention uses kaolin as a catalyst to convert fatty acid and ethanol into fatty acid ethyl ester. The rice bran oil has weaker fragrance after main fatty acid in the rice bran oil is converted into fatty acid ethyl ester, and the flavor of the rice bran oil can be improved. The ethyl linoleate has effects of regulating blood cholesterol, preventing and treating atherosclerosis, and resisting variation.
The invention adopts the following technical scheme:
a process for the conversion of fatty acids to fatty acid ethyl esters comprising the steps of:
adding rice bran and edible alcohol into a reaction bottle according to the mass ratio of 1:3, heating to 60 ℃ for extraction for 3 hours under the protection of nitrogen, filtering, putting a filter cake into the reaction bottle, adding the edible alcohol with the same mass, heating to 60 ℃ for extraction for 3 hours under the protection of nitrogen, filtering, combining the two filtrates, standing, layering, taking an upper-layer ethanol phase, adding kaolin and the edible alcohol into the ethanol phase according to the mass ratio of 1:100, heating to 60-65 ℃ under the protection of nitrogen, carrying out T L C following the reaction end point, stopping stirring when the acid value is less than 3mg/g, filtering, and recovering the solvent to obtain the deacidified and decolored rice bran oil.
The invention has the following beneficial effects:
1. the deacidification condition is mild: kaolin catalyzes esterification reaction at 60-65 ℃.
2. The operation is simple: after the reaction rice bran, the edible alcohol and the kaolin are mixed, the deacidification and the decoloration of the rice bran oil are completed in one step.
3. The cost is low: the fatty acid ethyl ester obtained by esterifying fatty acid with ethanol can be mixed with the neutral rice bran oil at the lower layer, so that the yield of the rice bran oil is increased, and the kaolin is low in price.
4. The flavor and health care function of the rice bran oil are increased.
Detailed Description
The invention provides a method for converting fatty acid into fatty acid ethyl ester, which takes kaolin as a catalyst, and the fatty acid reacts with ethanol to generate the fatty acid ethyl ester so as to reduce the fatty acid in rice bran oil.
Adding rice bran and edible ethanol into a reaction bottle according to the mass ratio of W: W =1.00:3.00, heating to 60 ℃ for extraction for 3h under the protection of nitrogen, filtering, repeating the previous experiment, extracting once again, filtering, combining the two filtrates, standing, layering, separating the lower layer to obtain a neutral oil phase and the upper layer to obtain an ethanol phase, adding kaolin and the edible ethanol into the ethanol phase according to the mass ratio of W: W =1.00:100.00, heating to 60-65 ℃ under the protection of nitrogen, tracking the reaction end point by T L C, stopping stirring when the acid value is less than 3mg/g (the acid value is determined according to the oil grade), filtering, and recovering the solvent to obtain the deacidified and decolored rice bran oil.
Examples
Adding rice bran (100.00 g) and edible alcohol (300.00 g, 6.5 mol) into a reaction bottle, heating to 60 ℃ under the protection of nitrogen, extracting for 3h, filtering, putting a filter cake into the reaction bottle, adding edible alcohol (300.00 g, 6.5 mol) into the reaction bottle, heating to 60 ℃ under the protection of nitrogen, extracting for 3h, filtering, combining the two filtrates, standing, layering, wherein the lower layer is neutral oil and the upper layer is an ethanol phase, separating, adding kaolin (6.00 g) into the ethanol phase, heating to 60-65 ℃ under the protection of nitrogen, tracking the reaction end point by T L C, stopping stirring when the acid value is less than 3mg/g (determining the acid value according to the grade of an oil product), filtering, recovering the solvent, and obtaining the acid-reduced and decolored rice bran oil.
Claims (1)
1. A method for converting fatty acid into fatty acid ethyl ester is characterized by comprising the following steps of adding rice bran and edible alcohol into a reaction bottle according to a mass ratio of 1:3, conducting nitrogen protection, heating to 60 ℃ for extraction for 3 hours, conducting filtering, placing a filter cake into the reaction bottle, adding edible alcohol with the same mass, conducting nitrogen protection, heating to 60 ℃ for extraction for 3 hours, conducting filtering, combining two filtrates, standing, layering, taking an upper layer of ethanol phase, adding kaolin and the edible alcohol into the ethanol phase according to a mass ratio of 1:100, conducting nitrogen protection, heating to 60-65 ℃, conducting T L C following a reaction end point, stopping stirring when an acid value is less than 3mg/g, conducting filtering, recovering a solvent, and obtaining the acid-reduced and decolored rice bran oil.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010205258.0A CN111411018A (en) | 2020-03-23 | 2020-03-23 | Method for converting fatty acid into fatty acid ethyl ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010205258.0A CN111411018A (en) | 2020-03-23 | 2020-03-23 | Method for converting fatty acid into fatty acid ethyl ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111411018A true CN111411018A (en) | 2020-07-14 |
Family
ID=71487706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010205258.0A Pending CN111411018A (en) | 2020-03-23 | 2020-03-23 | Method for converting fatty acid into fatty acid ethyl ester |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111411018A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101058771A (en) * | 2007-05-30 | 2007-10-24 | 吴江市方霞企业信息咨询有限公司 | Removal process for free fatty acid |
| CN101319167A (en) * | 2008-06-13 | 2008-12-10 | 合肥工业大学 | High-acid value rice bran oil esterification depickling process |
| CN102453613A (en) * | 2010-10-14 | 2012-05-16 | 姚昂 | Method for producing diesel oil by esterification deacidification of rice bran oil |
| CN102618383A (en) * | 2012-04-19 | 2012-08-01 | 北镇市五峰米业加工有限公司 | Production method and system of deacidification rice bran oil |
| CN108048223A (en) * | 2017-12-27 | 2018-05-18 | 袁祥龙 | A kind of production method of little rice bran edible oil |
-
2020
- 2020-03-23 CN CN202010205258.0A patent/CN111411018A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101058771A (en) * | 2007-05-30 | 2007-10-24 | 吴江市方霞企业信息咨询有限公司 | Removal process for free fatty acid |
| CN101319167A (en) * | 2008-06-13 | 2008-12-10 | 合肥工业大学 | High-acid value rice bran oil esterification depickling process |
| CN102453613A (en) * | 2010-10-14 | 2012-05-16 | 姚昂 | Method for producing diesel oil by esterification deacidification of rice bran oil |
| CN102618383A (en) * | 2012-04-19 | 2012-08-01 | 北镇市五峰米业加工有限公司 | Production method and system of deacidification rice bran oil |
| CN108048223A (en) * | 2017-12-27 | 2018-05-18 | 袁祥龙 | A kind of production method of little rice bran edible oil |
Non-Patent Citations (4)
| Title |
|---|
| AIDAN M. DOYLE 等: ""Biodiesel production by esterification of oleic acid over zeolite Y prepared from kaolin", 《RENEWABLE ENERGY》 * |
| 刘军海: "米糠油在甲醇和乙醇中的原位酯化作用", 《四川粮油科技》 * |
| 李宇凡 等: "醇法提取小米糠油工艺优化", 《中国油脂》 * |
| 胡晓军 等: "乙醇萃取米糠油脱酸脱蜡工艺研究", 《中国粮油学报》 * |
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