CN108611189B - Refining process for controlling bisphenol A and alkylphenol in grease - Google Patents
Refining process for controlling bisphenol A and alkylphenol in grease Download PDFInfo
- Publication number
- CN108611189B CN108611189B CN201611129741.5A CN201611129741A CN108611189B CN 108611189 B CN108611189 B CN 108611189B CN 201611129741 A CN201611129741 A CN 201611129741A CN 108611189 B CN108611189 B CN 108611189B
- Authority
- CN
- China
- Prior art keywords
- oil
- seed oil
- grease
- bisphenol
- content
- 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.)
- Active
Links
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
- C11B3/02—Refining fats or fatty oils by chemical reaction
- C11B3/06—Refining fats or fatty oils by chemical reaction with bases
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
- A23D9/04—Working-up
-
- 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
Abstract
The invention provides a method for reducing bisphenol A and/or alkylphenol in raw material grease, which comprises the steps of contacting the grease with alkali liquor at 0-10 ℃, shearing at high speed and separating solid from liquid. The method can obviously reduce the bisphenol A and/or alkylphenol in the raw material grease.
Description
Technical Field
The invention relates to the field of edible oil, in particular to a refining process for controlling bisphenol A and alkylphenol in oil.
Background
Bisphenol a and alkylphenols, such as NonylPhenol (NP) are among the environmental hormone pollutants. Alkylphenols and BisPhenol a (bistpenol a, BPA for short) are considered representative environmental endocrine disruptors.
Nonyl phenol, also known as nonyl phenol, is a generic name for several different isomers of the chemical formula C6H4 (OH) C9H 19. The average molecular weight is 220, the sludge is oily matter under certain temperature and pressure, has slight phenol smell, is not easy to dissolve in water, can be dissolved in alkaline solution and organic solvents such as methanol, acetone, dimethyl sulfoxide and the like, has very high oil-water distribution coefficient, is easy to deposit in sludge, and has quite stable property.
Bisphenol A, IUPAC 2, 2-bis (4-hydroxyphenyl) propane, bisphenol A is bisphenol propane for short, is slightly soluble in water (solubility at 25 ℃ is 0.3-0.381 g/L) and aliphatic hydrocarbon, is dissolved in organic solvents such as acetone, ethanol, toluene and the like, and is white to light brown flaky crystal or powder at normal temperature.
They are all easily soluble in grease, inner walls of oil storage tanks (phenolic resin coatings) in grease production, plastic oil pipelines, parts (rubber sealing rings and gaskets) in contact with grease, plastic containers and the like; the soil of the planting field of the raw material, the degree of pretreatment of the seed material, and the like may cause contamination of bisphenol a and long-chain alkylphenol (particularly nonylphenol).
At present, no detection standard of bisphenol A in grease and food and no determination standard of alkylphenol content in food exist. There is no article or patent related to reducing or controlling bisphenol a and alkylphenol contamination in grease and food. The relevant reports focus on the removal of bisphenol a and alkylphenols from environmental water or sludge, and the main methods are physical methods such as removal by adsorption routes, e.g. adsorbent orthogonal cyclodextrin polymers, activated carbon for BPA removal from water, reference: zhao Chang, mao and Liu Zong, etc. research on bisphenol A removal by activated carbon-embedded polymeric microspheres [ J ] research on water treatment technology, 2006,32 (5): 52-54.CN201410581507.0 removal of phenolic pollutants and the like in water by adopting a magnetic nano composite material; chemical methods, methods commonly employed for oxidation, such as photocatalytic oxidation, references: zhanyun, yanxi, yanghong, et al, study of influence of humus of natural water body on bisphenol A photodegradation [ J ]. Scientific report on Environment, 2005,25 (6): 816-820. Electrochemical oxidation method, reference: kuramitz H, nakata Y, kawasaki M, et al, electrochemical oxidation of bipolar A application to the removal of bipolar A using a carbon fiber electrode [ J ]. ChemOSPHER, 2001, 45. Ozone oxidation method, etc.; biological methods, such as microbial degradation, references: jiang jun degrading nonyl phenol and bisphenol a bacteria separation, identification and degradation property study [ D ], master academic thesis of university of east china, 2010.
The content of bisphenol a and alkylphenol in the conventional oil refining process cannot be well controlled, so that the process for processing edible oil needs to be improved to reduce the content.
Disclosure of Invention
The inventor of the invention discovers through research that at low temperature, a proper amount of alkali solution is added into the grease, and after shearing at high speed for at least 30min, solid-liquid separation is carried out, so that the clear oil with low content of bisphenol A and/or alkylphenol is obtained.
Accordingly, a first object of the present invention is to provide a method for reducing bisphenol a and/or alkylphenol in oils and fats.
The method provided by the invention comprises the steps of contacting raw material grease with alkali liquor at 0-10 ℃, shearing at high speed and separating solid from liquid.
In some examples of the present invention, the alkali in the alkali solution is used in an amount of 0.001 to 0.1% by weight of the raw oil and/or the alkali solution has a concentration of 1 to 30%, preferably 1 to 20%, more preferably 1 to 15%.
In some embodiments of the invention, the shear rate of the high shear is no more than 5000rpm, preferably 1000 to 5000rpm.
In some embodiments of the invention, the high shear time is greater than 30min, preferably 120-480min.
In some examples of the invention, the solid-liquid separation is one or more of centrifugation, sedimentation, filtration and/or ultrafiltration.
In some examples of the invention, the process further comprises one or more of a degumming step, a deacidification step, a water wash drying step, a decolorization step, and a deodorization step.
In some examples of the present invention, the oil or fat is an oil or fat having a high content of bisphenol a and/or alkylphenol, and preferably, the content of bisphenol a is not less than 40ppb and the content of alkylphenol is not less than 40ppb, based on the weight of the raw oil or fat.
In some examples of the invention, the deacidification step is an alkaline process deacidification.
The invention also provides grease with low content of bisphenol A and/or alkylphenol.
In the grease with low content of bisphenol A and/or alkylphenol provided by the invention, the content of the bisphenol A is less than 10ppb, preferably less than 1ppb, and/or the content of the alkylphenol is less than 10ppb, preferably less than 1ppb, based on the weight of the grease.
In some embodiments of the invention, the grease is prepared using the aforementioned methods of the invention.
The method can well reduce the content of bisphenol A and/or alkylphenol in the raw material grease. The method can be combined with the oil refining process, is simple, quick and effective, does not influence the original oil refining process, and is suitable for industrial production of oil. The problem of pollution of environmental hormone pollutants in the grease is effectively solved, and the safety of the grease is ensured.
Detailed Description
The present invention will be further described with reference to the following examples. It should be understood that the following preferred examples are illustrative only and are not intended to limit the scope of the invention.
The experimental methods of the following examples, which are not specified under specific conditions, are generally determined according to national standards. If there is no corresponding national standard, it is carried out according to the universal international standard, the conventional conditions, or the conditions recommended by the manufacturer.
Unless defined or stated otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In addition, any methods and materials similar or equivalent to those described herein can be used in the methods of the present invention.
As used herein, the term "comprising" or "includes" means that the various ingredients can be used together in a mixture or composition of the invention. Thus, the terms "consisting essentially of and" consisting of are encompassed by the terms "comprising" or "including".
The "ranges" disclosed herein are in the form of lower and upper limits. There may be one or more lower limits, and one or more upper limits, respectively. The given range is defined by selecting a lower limit and an upper limit. The selected lower and upper limits define the boundaries of the particular range. All ranges that can be defined in this manner are inclusive and combinable, i.e., any lower limit can be combined with any upper limit to form a range. For example, if the minimum range values 1 and 2 are listed, and if the maximum range values 3,4, and 5 are listed, the following ranges are all contemplated: 1-3, 1-4, 1-5, 2-3, 2-4, and 2-5.
In the present invention, the ranges of the contents of the components of the composition and the preferred ranges thereof may be combined with each other to form a new technical solution, unless otherwise specified.
In the present invention, unless otherwise specified, "combinations thereof" mean multicomponent mixtures of the individual elements mentioned, for example two, three, four and up to the maximum possible multicomponent mixtures.
In the present invention, all "parts" and percentages (%) refer to weight percentages unless otherwise indicated.
In the present invention, the sum of the percentages of the components in all compositions is 100%, unless otherwise specified.
In the present invention, unless otherwise stated, the numerical range "a-b" represents a shorthand representation of any combination of real numbers between a and b, including the endpoints, where a and b are both real numbers. For example, a numerical range of "0 to 5" indicates that all real numbers between "0 to 5" have been listed herein, and "0 to 5" is only a shorthand representation of the combination of these numbers.
The terms "a" and "an" as used herein mean "at least one" if not otherwise specified.
In the present invention, all embodiments and preferred embodiments mentioned herein may be combined with each other to form a new technical solution, if not specifically stated.
In the present invention, all the technical features mentioned herein and preferred features may be combined with each other to form a new technical solution, if not specifically stated.
The inventor of the invention discovers through research that at low temperature, a proper amount of alkali solution is added into the grease, and after shearing at high speed for at least 30min, solid-liquid separation is carried out, so that the clear oil with low content of bisphenol A and/or alkylphenol is obtained.
Method for reducing bisphenol A and/or alkylphenol in grease
The method for reducing bisphenol A and/or alkylphenol in raw material grease provided by the invention comprises the steps of contacting the raw material grease with alkali liquor at 0-10 ℃, shearing at high speed and separating solid from liquid.
In the following examples of the present invention, the raw material oil is contacted with the alkali solution at 0 to 10 ℃, the temperatures of the raw material oil and the alkali solution can be controlled to be 0 to 10 ℃ respectively, and the raw material oil and the alkali solution are contacted; or contacting the raw material oil with alkali liquor and controlling the temperature of the mixed liquor to be 0-10 ℃.
In some embodiments of the present invention, the alkali in the alkaline solution is used in an amount of 0.001 to 0.1% by weight of the oil. In the present invention, the amount of alkali in the lye refers to the amount of alkali (solute) added to the lye, e.g. sodium hydroxide solution, e.g. solid alkali, e.g. solid sodium hydroxide.
In some embodiments of the invention, the lye concentration is 1 to 30%, preferably 1 to 20%, more preferably 1 to 15%.
In some embodiments of the invention, the shear rate of the high shear is no more than 5000rpm, preferably 1000 to 5000rpm. When the shearing rate exceeds 5000rpm, grease is seriously emulsified, so that clear oil is not easy to separate, and subsequent detection and refining are influenced. Therefore, the shear rate in this experiment is preferably not more than 5000rpm.
The inventors have found that longer shear times favor BPA and NP removal. Thus, in some embodiments of the invention, the high shear time is greater than 30min, and preferably 120-480min, in view of removal efficiency and cost.
In the present invention, the solid-liquid separation method may be a method conventionally used in the art for solid-liquid separation in fats and oils, may be a method for solid-liquid separation, and may also be a combination of a plurality of methods for solid-liquid separation. In some examples of the invention, the solid-liquid separation may be one or more of centrifugation, sedimentation, filtration, and/or ultrafiltration.
In some examples of the invention, the method is used in or in conjunction with one or more steps in a fat refining process. The oil refining process optionally comprises one or more steps of degumming, deacidification, water washing and drying, decoloring and deodorizing.
In some examples of the present invention, the deacidification step is alkali refining deacidification, enzymatic deacidification, esterification deacidification, or the like.
In the following examples of the present invention, the degumming step is hydration degumming, enzymatic degumming, acid degumming (concentrated sulfuric acid or dilute sulfuric acid), adsorption degumming, electropolymerization degumming, thermal coagulation degumming, etc.
In the following examples of the present invention, the decoloring step is adsorption decoloring, light energy decoloring, heat energy decoloring, hydrogenation decoloring, oxidation decoloring, air decoloring, reagent decoloring, liquid-liquid extraction decoloring, or the like.
In the following examples of the invention, the deodorization step is steam stripping deodorization, molecular distillation deodorization, etc.
In some examples of the present invention, the raw material oil or fat used is an oil or fat having a high bisphenol a content and/or an alkylphenol content; preferably, the content of the bisphenol A is not less than 40ppb, and the content of the alkylphenol is not less than 40ppb based on the weight of the raw material grease. In some examples of the present invention, the raw oil or fat is a raw oil or fat derived from animal oil or fat or vegetable oil or fat which has not been treated by the method of the present invention. Non-limiting examples of the vegetable oil or fat or animal oil and fat include: rice oil (rice bran oil), sunflower seed oil, palm kernel oil, peanut oil, rapeseed oil, soybean oil, linseed oil, cottonseed oil, safflower seed oil, perilla seed oil, tea seed oil, castor bean oil, jojoba oil, olive oil, cocoa bean oil, chinese tallow tree seed oil, almond oil, apricot oil, tung seed oil, rubber seed oil, corn germ oil, wheat germ oil, sesame seed oil, evening primrose seed oil, hazelnut oil, pumpkin seed oil, walnut oil, grape seed oil, linseed oil, glass seed oil, sea buckthorn seed oil, tomato seed oil, macadamia nut oil, coconut oil, cocoa butter, algae oil, beef tallow, lard, mutton fat, chicken fat, fish oil, seal oil, whale oil, dolphin oil, oyster oil, lanolin, and the like or mixtures thereof.
The invention also provides grease with low content of bisphenol A and/or alkylphenol.
In the grease with low content of bisphenol A and/or alkylphenol provided by the invention, the content of the bisphenol A is less than 10ppb, preferably less than 1ppb, and/or the content of the alkylphenol is less than 10ppb, preferably less than 1ppb, based on the weight of the grease.
In some embodiments of the invention, the grease is prepared using the aforementioned methods of the invention.
In some embodiments of the present invention, the low bisphenol a and/or alkylphenol content grease provided by the present invention may further comprise an emulsifier, including but not limited to: polyglycerol fatty acid ester, sodium stearoyl lactate, calcium stearoyl lactate and sucrose fatty acid ester; antioxidants, including but not limited to: rosemary extract, tea polyphenol (aka vitamin polyphenol), tea polyphenol palmitate, butylated Hydroxyanisole (BHA), butylated Hydroxytoluene (BHT), glycyrrhiza antioxidant, ascorbyl palmitate, propyl Gallate (PG), hydroxystearin (aka stearin), tert-butylhydroquinone (TBHQ), vitamin E (dl-alpha-tocopherol, d-alpha-tocopherol, mixed tocopherol concentrate), phytic acid (aka phytic acid), sodium phytate, bamboo leaf antioxidant, theaflavin, ascorbyl palmitate (enzymatic process).
In the following examples of the present invention, the raw material was subjected to the mode of adding BPA and NP in reverse, and the content of BPA and NP in the raw material was measured after adding in reverse, the measurement method was referred to: jian Lu, jun Wu, peter J.Stoffella, and P.Chris Wilson.analysis of Bisphenol A, nonylphenol, and Natural Escherichia in vegetables and Natural Escherichia in vitro Chromatography with nucleic acids Chromatography-Tandem Mass Spectrometry [ J ]. J.Agrric.food Chem.2013,61,84-89.
In the following examples of the invention, the refined soybean oil feedstock, refined corn oil, used were purchased from a supermarket, and BPA and NP were added to the corresponding amounts in the examples.
The first embodiment is as follows: effect of different lye concentrations on the content of BPA and NP
Taking refined soybean oil, cooling to 5 ℃, and then adding a sodium hydroxide solution to react with the refined soybean oil according to the method shown in the table 1, wherein the mass of sodium hydroxide (solute) is 0.03 percent of the weight of the oil. High shear was started after addition of the lye, with a shear rate of 3000rpm. Maintaining the temperature at 5 ℃ for shearing reaction for 300min, and then centrifuging to obtain the soybean clear oil.
The final soybean oil was examined for BPA and NP content and the results are shown in Table 1.
TABLE 1
| Name of sample | BPA content (μ g/kg) | NP content (μ g/kg) |
| Raw materials: refined soybean oil | 848.30 | 42.81 |
| Soybean clear oil obtained when the concentration of NaOH solution is 1% | <1 (reduction rate)>99％) | <1 (reduction rate)>99％) |
| Soybean clear oil obtained when the concentration of NaOH solution is 5% | <1 (reduction rate)>99％) | <1 (reduction rate)>99％) |
| Soybean clear oil obtained when the concentration of NaOH solution is 15% | <1 (reduction rate)>99％) | <1 (reduction rate)>99％) |
| Soybean clear oil obtained when the concentration of NaOH solution is 20% | 9.35 (reduction ratio 99%) | 2.57 (reduction rate 94%) |
| Soybean clear oil obtained when the concentration of NaOH solution is 30% | 84.09 (reduction rate 90%) | 6.42 (reduction rate 85%) |
| Soybean clear oil obtained when the concentration of NaOH solution is 50% | 127.25 (reduction rate 85%) | 8.17 (reduction ratio 81%) |
As can be seen from Table 1, different lye concentrations under the above conditions can significantly reduce the BPA and NP content of the refined soybean oil. The reduction efficiency shows a gradually reduced trend along with the increase of the concentration of the alkali liquor.
Example two: effect of shear Rate on BPA and NP content
Taking refined soybean oil, cooling to 5 ℃, and then adding a sodium hydroxide solution to react with the refined soybean oil, wherein the concentration of the sodium hydroxide solution is 15%, and the mass of sodium hydroxide (solute) is 0.03% of the weight of the oil. High speed shearing is started after adding alkali liquor, and the shearing speed is 0-5000rpm. Maintaining the temperature at 5 ℃ for shearing reaction for 300min, and then centrifuging to obtain the soybean clear oil.
The final soybean oil was examined for BPA and NP content and the results are shown in Table 2.
TABLE 2
And (4) conclusion: as can be seen from table 2, high shear can significantly reduce BPA and NP levels of refined soybean oil. Decreasing efficiency tends to increase and decrease with increasing shear rate. When the shearing rate exceeds 5000rpm, grease is seriously emulsified, so that clear oil is not easy to separate, and subsequent detection and refining are influenced. Therefore, the shear rate in this experiment is preferably not more than 5000rpm.
Example three: effect of other parameters on the content of BPA and NP
Adding sodium hydroxide solution into refined soybean oil to react with the refined soybean oil, wherein the concentration of the sodium hydroxide solution is 15 percent, and the mass of sodium hydroxide (solute) is 0.001 to 0.1 percent of the weight of the oil. High shear was started after addition of the lye, with a shear rate of 3000rpm. Keeping the temperature at 5 ℃ for shearing reaction for 30-480 min, and then centrifuging to obtain the soybean clear oil.
The BPA and NP contents of the finally obtained soybean oil were measured, and the results are shown in Table 3.
TABLE 3
And (4) conclusion: the temperature is low, the BPA and NP removal effect is good, but when the temperature is lower than 0 ℃, the grease is in a frozen state and is not beneficial to centrifugal separation; a small amount of sodium hydroxide is added, so that the effect of removing BPA and NP can be achieved; the longer the shear time, the more favorable the removal of BPA and NP.
Example four: effect of other oil species on the content of BPA and NP
Taking refined corn oil, adding sodium hydroxide solution to react with the refined corn oil, wherein the concentration of the sodium hydroxide solution is 15%, and the mass of sodium hydroxide (solute) is 0.03% of the weight of the oil. High shear was started after addition of the lye, with a shear rate of 3000rpm. Maintaining the temperature at 5 ℃ for shearing reaction for 300min, and then centrifuging to obtain the corn clear oil.
The final corn clear oil was tested for BPA and NP content and the results are shown in Table 4.
TABLE 4
| Name of sample | BPA content (. Mu.g/kg) | NP content (μ g/kg) |
| Raw materials: refined corn oil | 50.39 | 53.97 |
| Treated sample | <1 | <1 |
And (4) conclusion: the use of refined corn oil with high shear also results in a very significant reduction in the BPA and NP levels.
Example five: in the process of oil and fat refining
(1) Degumming
500g of crude soybean oil was weighed into a 1000ml beaker, heated to 80 ℃ with stirring, and 0.5g of phosphoric acid (phosphoric acid was added slowly at 0.1% by weight of the oil) was added. Stirring and heating are continued for 30min, and finally centrifugation is carried out for 10min at the rotating speed of 4500 r/min. Obtaining the degummed soybean oil.
(2) Alkali refining
Weighing degummed soybean oil in a beaker, stirring and heating to 50 ℃, and stirring at the speed of 450r/min. Then adding alkali liquor (the calculation formula of the alkali adding amount is W) NaOH ＝7.13*AV*W Oil(s) * (1 + excess base)/10000, the calculation formula of the solution is: w NaOH 0.15, calculated as 20% of the oil weight). Stirring and reacting for 40min, centrifuging the reacted oil in a centrifuge at the speed of 4500r/min for 10min, and separating oil soap to obtain the soap-removed soybean oil.
(3) Washing and drying
The centrifuged soybean oil was washed with hot water (10% by weight of the oil) and finally dehydrated under vacuum. (heating to 105 ℃ C., maintaining for 15min until no bubbles are present).
(4) High speed shearing
Taking the washed and dried soybean oil, cooling to 5 ℃, and then adding a proper amount of sodium hydroxide solution to react with the refined soybean oil, wherein the concentration of the sodium hydroxide solution is 15%, and the mass of sodium hydroxide (solute) is 0.03% of the weight of the oil. High shear was started after addition of the lye, with a shear rate of 3000rpm. Maintaining the temperature at 5 ℃ for shearing reaction for 300min, and then freezing and centrifuging to obtain the soybean clear oil.
(5) Decolorizing
Placing the clear oil in a flat-bottom three-neck flask, stirring and heating on a magnetic stirring table at the stirring speed of 750r/min, heating to 105 ℃ under a vacuum condition, adding 1% acid activated clay, continuously decoloring for 30min, and performing suction filtration to obtain the decolored soybean oil.
(6) Deodorization
Heating the obtained decolorized oil to 210 deg.C under vacuum nitrogen-filled condition, deodorizing for 60min, and cooling to 70 deg.C under nitrogen-filled vacuum condition to obtain deodorized soybean oil.
(7) The final deodorized soybean oil was tested for BPA and NP content. The results are shown in Table 5.
TABLE 5
| Sample name | BPA content (μ g/kg) | NP content (μ g/kg) |
| Crude soybean oil | 3429 | 1624 |
| Deodorized soybean oil | <1 (reduction rate)>99％) | <1 (reduction rate)>99％) |
And (4) conclusion: by adopting the patented steps, the content of BPA and NP in the grease can be obviously reduced, and the grease is not influenced by raw materials or other refining steps.
Comparative example one: conventional refining step
(1) Degumming:
500g of crude soybean oil was weighed into a 1000ml beaker, heated to 80 ℃ with stirring, and 0.5g of phosphoric acid (phosphoric acid was added slowly at 0.1% by weight of the oil) was added. Stirring and heating are continued for 30min, and finally centrifugation is carried out for 10min at the rotating speed of 4500 r/min. And obtaining the degummed soybean oil.
(2) Alkali refining:
weighing degummed soybean oil in a beaker, stirring and heating to 50 ℃, wherein the stirring speed is 450r/min. Then adding alkali liquor (the calculation formula of the alkali adding amount is W) NaOH ＝7.13*AV*W Oil * (1 + excess base)/10000, the calculation formula of the solution is: w NaOH 0.15, calculated as 20% of the oil weight). Stirring for 40min, centrifuging the reacted oil in a centrifuge at 4500r/min for 10min, and separating oil soap to obtain the soap-removed soybean oil.
(3) Washing and drying:
the centrifuged soybean oil was washed with hot water (10% by weight of the oil) and finally dehydrated under vacuum. (heating to 105 ℃ C., maintaining for 15min until no bubbles are present).
(4) And (3) decoloring:
placing the clear oil in a flat-bottom three-neck flask, stirring and heating on a magnetic stirring table at the stirring speed of 750r/min, heating to 105 ℃ under a vacuum condition, adding 1% of acid activated argil, continuously decoloring for 30min, and then performing suction filtration to obtain the decolored soybean oil.
(5) Deodorizing:
heating the obtained decolorized oil to 210 deg.C under vacuum nitrogen-filled condition, deodorizing for 60min, and cooling to 70 deg.C under nitrogen-filled vacuum condition to obtain deodorized soybean oil.
(6) The final deodorized soybean oil was tested for BPA and NP content. The results are shown in Table 6.
TABLE 6
| Name of sample | BPA content (μ g/kg) | NP content (μ g/kg) |
| Crude soybean oil | 3429 | 1624 |
| Deodorized soybean oil | 2068(40％) | 910(44％) |
And (4) conclusion: the conventional refining cannot obviously reduce the content of BPA and NP in the grease.
Comparative example two: conventional dewaxing step
Weighing the soybean oil after washing and drying in a beaker, slowly cooling to 5 ℃, and slowly stirring (50 rpm) for growing the crystal for 300min. Then filtering at low temperature of about 5 ℃ to obtain the soybean oil clear oil. The clear oils were tested for BPA and NP content and the results are shown in Table 7.
TABLE 7
| Sample name | BPA content (μ g/kg) | NP content (μ g/kg) |
| Dried soybean oil | 3413 | 1658 |
| Conventional dewaxed soybean oil | 3515 | 1569 |
And (4) conclusion: conventional dewaxing cannot reduce the content of BPA and NP in grease.
Claims (8)
1. A method for reducing bisphenol A and/or alkylphenol in raw material grease is characterized in that the grease is contacted with alkali liquor at 0-10 ℃, high-speed shearing and solid-liquid separation are carried out, the dosage of alkali in the alkali liquor is 0.001-0.1%, the concentration of the alkali liquor is 1-15%, the content of bisphenol A in the raw material grease is not less than 40ppb, and/or the content of alkylphenol is not less than 40ppb; the raw material oil is rice oil, sunflower seed oil, peanut oil, rapeseed oil, soybean oil, linseed oil, cottonseed oil, safflower seed oil, perilla seed oil, tea seed oil, castor seed oil, jojoba oil, olive oil, chinese tallow tree seed oil, almond oil, apricot oil, tung oil, rubber seed oil, corn germ oil, wheat germ oil, sesame seed oil, evening primrose seed oil, hazelnut oil, pumpkin seed oil, walnut oil, grape seed oil, linseed oil, glass chicory seed oil, sea buckthorn seed oil, tomato seed oil, macadamia nut oil, algae oil or a mixture thereof; optionally, one or more steps of degumming, deacidification, washing and drying, decoloring and deodorizing are also included before the raw material oil is contacted with the alkali liquor.
2. The method of claim 1, wherein the high shear rate is no more than 5000rpm.
3. The method of claim 1, wherein the high shear has a shear rate of 1000 to 5000rpm.
4. The method of claim 1, wherein the high shear time is greater than 30min.
5. The method of claim 1, wherein the high shear time is from 120 to 480min.
6. The method of claim 1, wherein the solid-liquid separation is one or more of centrifugation, sedimentation, filtration and/or ultrafiltration.
7. The method according to any one of claims 1 to 6, further comprising one or more of a degumming step, a deacidification step, a water wash drying step, a decolouration step and a deodorization step.
8. The method of claim 7, wherein said deacidifying step is alkaline deacidifying.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611129741.5A CN108611189B (en) | 2016-12-09 | 2016-12-09 | Refining process for controlling bisphenol A and alkylphenol in grease |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611129741.5A CN108611189B (en) | 2016-12-09 | 2016-12-09 | Refining process for controlling bisphenol A and alkylphenol in grease |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108611189A CN108611189A (en) | 2018-10-02 |
| CN108611189B true CN108611189B (en) | 2023-02-21 |
Family
ID=63657340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201611129741.5A Active CN108611189B (en) | 2016-12-09 | 2016-12-09 | Refining process for controlling bisphenol A and alkylphenol in grease |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108611189B (en) |
Citations (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2677700A (en) * | 1951-05-31 | 1954-05-04 | Wyandotte Chemicals Corp | Polyoxyalkylene surface active agents |
| US3870670A (en) * | 1972-06-19 | 1975-03-11 | Reichhold Albert Chemie Ag | Process for the manufacture of dispersions of thermosetting reaction products |
| US3871896A (en) * | 1971-10-11 | 1975-03-18 | Kansai Paint Co Ltd | Precoated metal sheets and manufacture thereof |
| US4030935A (en) * | 1976-04-20 | 1977-06-21 | Shults Mikhail M | Glass |
| EP0034387A2 (en) * | 1980-02-14 | 1981-08-26 | THE PROCTER & GAMBLE COMPANY | Mulls containing chain structure clay suspension aids |
| JPS6327448A (en) * | 1986-07-17 | 1988-02-05 | Daicel Chem Ind Ltd | Production of high-purity di-alkali metallic salt of bisphenol |
| JPH02246150A (en) * | 1989-03-20 | 1990-10-01 | Hitachi Ltd | Semiconductor integrated circuit device, its formation and apparatus for producing it |
| CN1062680A (en) * | 1991-11-04 | 1992-07-15 | 中国石油化工总公司 | The basic compound catalysis alkyl phenolic alkoxy of calcium |
| CN1066648A (en) * | 1991-05-16 | 1992-12-02 | 时明水 | Purifying bisphenol a solvent by chemical extraction |
| EP0524027A3 (en) * | 1991-07-18 | 1993-03-31 | Sanyo Chemical Industries, Ltd. | Polyester resin and its use as a toner binder |
| EP0228085B1 (en) * | 1985-12-26 | 1993-06-09 | Fuji Photo Film Co., Ltd. | Light-sensitive material containing silver halide, reducing agent and polymerizable compound, and image-forming method employing the same |
| CN1086843A (en) * | 1992-09-01 | 1994-05-18 | 普罗格特-甘布尔公司 | The liquid or the glue that contain alkyl both sexes carboxylic acid and magnesium or calcium ion are washed the dish detergent composition |
| CN1188075A (en) * | 1997-01-14 | 1998-07-22 | 武汉大学 | Preparation of high pure globular amorphous silicon powder |
| CN1198734A (en) * | 1996-08-23 | 1998-11-11 | 北美埃尔夫爱托化学股份有限公司 | Novel poly(monoperoxycarbonates) |
| CN1245185A (en) * | 1998-08-18 | 2000-02-23 | 科莱恩有限公司 | Flow enhanced pigment preparation for offset printing |
| CN1271715A (en) * | 1999-04-27 | 2000-11-01 | 布兰科尼尔有机合成研究院 | Method for obtaining biphenol A |
| CN1353746A (en) * | 1999-06-02 | 2002-06-12 | 英国石油勘探运作有限公司 | Process for reducing acidity of oil |
| EP1254936A2 (en) * | 2001-05-04 | 2002-11-06 | Rohm And Haas Company | Method for preparing a laminate |
| CN1558924A (en) * | 2001-07-24 | 2004-12-29 | ͨ�õ�����˾ | Method of polycarbonate preparation |
| CN1778460A (en) * | 2004-11-26 | 2006-05-31 | 刘春德 | Surface activator containing bisphenol, its formula system and use for triple oil extraction |
| CN1796424A (en) * | 2004-12-21 | 2006-07-05 | 天津渤天化工有限责任公司 | Method for fabricating mixing resin of chloroacetic copolymerization in use for polyvinyl chloride paste |
| JP2007009195A (en) * | 2005-05-31 | 2007-01-18 | Sanyo Chem Ind Ltd | Agent for increasing fluidity of fuel oil and fuel oil composition |
| EP1820896A3 (en) * | 2001-11-07 | 2007-10-10 | Bayer MaterialScience LLC | Process for dip-dyeing molded articles from polycarbonate |
| CN101125299A (en) * | 2007-08-31 | 2008-02-20 | 上海理工大学 | Ti/13X/MCM-41 composite material |
| CN101470366A (en) * | 2007-12-28 | 2009-07-01 | 夏普株式会社 | Toner, two-component developer, developing device, and image forming apparatus |
| CN101535201A (en) * | 2006-12-14 | 2009-09-16 | 帝斯曼知识产权资产管理有限公司 | D1370 r radiation curable secondary coating for optical fiber |
| CN101549524A (en) * | 2009-04-30 | 2009-10-07 | 巨化集团公司 | Water-soluble grease concrete releasing agent and preparation method thereof |
| CN101679077A (en) * | 2007-06-15 | 2010-03-24 | Omya发展股份公司 | Surface-reacted calcium carbonate in combination with hydrophobic adsorbent for water treatment |
| CN101709554A (en) * | 2009-08-18 | 2010-05-19 | 石狮市万峰盛漂染织造有限公司 | Surfactant for woven fabric dye-bath retreat process and preparation method thereof |
| CN102088823A (en) * | 2009-12-07 | 2011-06-08 | 山荣化学株式会社 | Printed wiring board and method for producing the same |
| CN102161618A (en) * | 2011-03-11 | 2011-08-24 | 南通星辰合成材料有限公司 | Method for removing acid in process of bisphenol A production |
| CN102183606A (en) * | 2011-03-02 | 2011-09-14 | 北京师范大学 | Method for detecting estrogen, nonyl phenol, octyl phenol and bisphenol A in water body sediment together |
| CN102283295A (en) * | 2010-06-17 | 2011-12-21 | 丰益(上海)生物技术研发中心有限公司 | Edible blend oil as well as preparation method and application thereof |
| CN102471567A (en) * | 2009-07-16 | 2012-05-23 | 出光兴产株式会社 | Portable electronic device case |
| CN103242971A (en) * | 2013-05-03 | 2013-08-14 | 武汉理工大学 | Green efficient thick oil dirt nearly-neutral water-based cleaning agent without adding any acid-base |
| CN103732667A (en) * | 2011-08-03 | 2014-04-16 | 沙特基础创新塑料Ip私人有限责任公司 | Glass filled copolymer products for thin wall and high surface gloss articles |
| CN104058652A (en) * | 2014-05-29 | 2014-09-24 | 安徽华塑股份有限公司 | High-strength concrete and preparation method thereof |
| WO2015031598A2 (en) * | 2013-08-30 | 2015-03-05 | Yale University | Therapeutic dnp derivatives and methods using same |
| CN104642326A (en) * | 2015-02-16 | 2015-05-27 | 河南科技学院 | Fungicidal composition containing penflufen and carvacrol and use of fungicidal composition |
| WO2015105514A1 (en) * | 2014-01-13 | 2015-07-16 | Unipixel Displays, Inc. | Coated nano-particle catalytically active composite inks |
| CN104862072A (en) * | 2015-05-08 | 2015-08-26 | 湖南红星盛康油脂股份有限公司 | Tea seed oil refining process |
| CN104968737A (en) * | 2012-12-17 | 2015-10-07 | 赢创德固赛有限公司 | Use of substituted benzyl alcohols in reactive epoxy systems |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1338288C (en) * | 1989-02-07 | 1996-04-30 | Jai Gopal Bansal | Method for the production of long chain hydrocarbyl substituted mono- or dicarboxylic acid materials |
| CN1050740A (en) * | 1989-10-05 | 1991-04-17 | 大连生物化学制药厂 | The production method of refined mink fat |
| US6660442B2 (en) * | 2001-04-03 | 2003-12-09 | Kao Corporation | Nonmagnetic black toner for reversal development |
| US7160667B2 (en) * | 2003-01-24 | 2007-01-09 | Fuji Photo Film Co., Ltd. | Image forming material |
| CN1313445C (en) * | 2004-03-24 | 2007-05-02 | 中国石油天然气股份有限公司 | Prepn process of high-alkalinity alkylphenol calcium sulfonate additive |
| CN100595242C (en) * | 2005-09-07 | 2010-03-24 | 鹤壁百运佳大豆油墨科技有限公司 | Prepn of green offset ink with waste soybean oil |
| US8747650B2 (en) * | 2006-12-21 | 2014-06-10 | Chevron Oronite Technology B.V. | Engine lubricant with enhanced thermal stability |
| CN102304204B (en) * | 2011-05-20 | 2014-09-10 | 中科院广州化学有限公司 | Fluorine-containing bi-functional microspheres and application thereof |
| CN102586013B (en) * | 2011-11-22 | 2013-09-11 | 郑州远洋油脂工程技术有限公司 | Dephenolizing and decoloring refining process and device for cottonseed oil |
| CN104694250B (en) * | 2013-12-10 | 2020-02-04 | 丰益(上海)生物技术研发中心有限公司 | Method for reducing 3-MCPD ester and/or glycidyl ester in grease |
| CN103740463B (en) * | 2014-01-10 | 2016-06-01 | 陈汉卿 | A kind of lipin deacidifying equipment and acid stripping method |
| WO2015116842A1 (en) * | 2014-02-03 | 2015-08-06 | Agxplore International | Urease inhibitor formulations |
| CN105016552B (en) * | 2014-04-22 | 2017-08-22 | 中国石油化工股份有限公司 | A kind of processing method of oil refinery spent lye |
| CN104277912A (en) * | 2014-09-27 | 2015-01-14 | 赖建辉 | Processing method for refining tea seed oil by one-step process |
| CN104621340B (en) * | 2015-01-30 | 2017-11-07 | 武汉轻工大学 | Cold press produces dephenolization cottonseed protein method |
| CN108239575B (en) * | 2016-12-23 | 2022-02-11 | 丰益(上海)生物技术研发中心有限公司 | Oil scavenger, method for scavenging phenolic substances in oil, treated oil and food using the same |
| CN107494765A (en) * | 2017-08-31 | 2017-12-22 | 安徽天祥粮油食品有限公司 | A kind of soybean ready-mixed oil and preparation method thereof |
| CN110305556A (en) * | 2019-06-12 | 2019-10-08 | 黄琳 | A kind of preparation method of quick-drying water-repellent paint |
-
2016
- 2016-12-09 CN CN201611129741.5A patent/CN108611189B/en active Active
Patent Citations (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2677700A (en) * | 1951-05-31 | 1954-05-04 | Wyandotte Chemicals Corp | Polyoxyalkylene surface active agents |
| US3871896A (en) * | 1971-10-11 | 1975-03-18 | Kansai Paint Co Ltd | Precoated metal sheets and manufacture thereof |
| US3870670A (en) * | 1972-06-19 | 1975-03-11 | Reichhold Albert Chemie Ag | Process for the manufacture of dispersions of thermosetting reaction products |
| US4030935A (en) * | 1976-04-20 | 1977-06-21 | Shults Mikhail M | Glass |
| EP0034387A2 (en) * | 1980-02-14 | 1981-08-26 | THE PROCTER & GAMBLE COMPANY | Mulls containing chain structure clay suspension aids |
| EP0228085B1 (en) * | 1985-12-26 | 1993-06-09 | Fuji Photo Film Co., Ltd. | Light-sensitive material containing silver halide, reducing agent and polymerizable compound, and image-forming method employing the same |
| JPS6327448A (en) * | 1986-07-17 | 1988-02-05 | Daicel Chem Ind Ltd | Production of high-purity di-alkali metallic salt of bisphenol |
| JPH02246150A (en) * | 1989-03-20 | 1990-10-01 | Hitachi Ltd | Semiconductor integrated circuit device, its formation and apparatus for producing it |
| CN1066648A (en) * | 1991-05-16 | 1992-12-02 | 时明水 | Purifying bisphenol a solvent by chemical extraction |
| EP0524027A3 (en) * | 1991-07-18 | 1993-03-31 | Sanyo Chemical Industries, Ltd. | Polyester resin and its use as a toner binder |
| CN1062680A (en) * | 1991-11-04 | 1992-07-15 | 中国石油化工总公司 | The basic compound catalysis alkyl phenolic alkoxy of calcium |
| CN1086843A (en) * | 1992-09-01 | 1994-05-18 | 普罗格特-甘布尔公司 | The liquid or the glue that contain alkyl both sexes carboxylic acid and magnesium or calcium ion are washed the dish detergent composition |
| CN1198734A (en) * | 1996-08-23 | 1998-11-11 | 北美埃尔夫爱托化学股份有限公司 | Novel poly(monoperoxycarbonates) |
| CN1188075A (en) * | 1997-01-14 | 1998-07-22 | 武汉大学 | Preparation of high pure globular amorphous silicon powder |
| CN1245185A (en) * | 1998-08-18 | 2000-02-23 | 科莱恩有限公司 | Flow enhanced pigment preparation for offset printing |
| CN1271715A (en) * | 1999-04-27 | 2000-11-01 | 布兰科尼尔有机合成研究院 | Method for obtaining biphenol A |
| CN1353746A (en) * | 1999-06-02 | 2002-06-12 | 英国石油勘探运作有限公司 | Process for reducing acidity of oil |
| EP1254936A2 (en) * | 2001-05-04 | 2002-11-06 | Rohm And Haas Company | Method for preparing a laminate |
| CN1558924A (en) * | 2001-07-24 | 2004-12-29 | ͨ�õ�����˾ | Method of polycarbonate preparation |
| EP1820896A3 (en) * | 2001-11-07 | 2007-10-10 | Bayer MaterialScience LLC | Process for dip-dyeing molded articles from polycarbonate |
| CN1778460A (en) * | 2004-11-26 | 2006-05-31 | 刘春德 | Surface activator containing bisphenol, its formula system and use for triple oil extraction |
| CN1796424A (en) * | 2004-12-21 | 2006-07-05 | 天津渤天化工有限责任公司 | Method for fabricating mixing resin of chloroacetic copolymerization in use for polyvinyl chloride paste |
| JP2007009195A (en) * | 2005-05-31 | 2007-01-18 | Sanyo Chem Ind Ltd | Agent for increasing fluidity of fuel oil and fuel oil composition |
| CN101535201A (en) * | 2006-12-14 | 2009-09-16 | 帝斯曼知识产权资产管理有限公司 | D1370 r radiation curable secondary coating for optical fiber |
| CN101679077A (en) * | 2007-06-15 | 2010-03-24 | Omya发展股份公司 | Surface-reacted calcium carbonate in combination with hydrophobic adsorbent for water treatment |
| CN101125299A (en) * | 2007-08-31 | 2008-02-20 | 上海理工大学 | Ti/13X/MCM-41 composite material |
| CN101470366A (en) * | 2007-12-28 | 2009-07-01 | 夏普株式会社 | Toner, two-component developer, developing device, and image forming apparatus |
| CN101549524A (en) * | 2009-04-30 | 2009-10-07 | 巨化集团公司 | Water-soluble grease concrete releasing agent and preparation method thereof |
| CN102471567A (en) * | 2009-07-16 | 2012-05-23 | 出光兴产株式会社 | Portable electronic device case |
| CN101709554A (en) * | 2009-08-18 | 2010-05-19 | 石狮市万峰盛漂染织造有限公司 | Surfactant for woven fabric dye-bath retreat process and preparation method thereof |
| CN102088823A (en) * | 2009-12-07 | 2011-06-08 | 山荣化学株式会社 | Printed wiring board and method for producing the same |
| CN102283295A (en) * | 2010-06-17 | 2011-12-21 | 丰益(上海)生物技术研发中心有限公司 | Edible blend oil as well as preparation method and application thereof |
| CN102183606A (en) * | 2011-03-02 | 2011-09-14 | 北京师范大学 | Method for detecting estrogen, nonyl phenol, octyl phenol and bisphenol A in water body sediment together |
| CN102161618A (en) * | 2011-03-11 | 2011-08-24 | 南通星辰合成材料有限公司 | Method for removing acid in process of bisphenol A production |
| CN103732667A (en) * | 2011-08-03 | 2014-04-16 | 沙特基础创新塑料Ip私人有限责任公司 | Glass filled copolymer products for thin wall and high surface gloss articles |
| CN104968737A (en) * | 2012-12-17 | 2015-10-07 | 赢创德固赛有限公司 | Use of substituted benzyl alcohols in reactive epoxy systems |
| CN103242971A (en) * | 2013-05-03 | 2013-08-14 | 武汉理工大学 | Green efficient thick oil dirt nearly-neutral water-based cleaning agent without adding any acid-base |
| WO2015031598A2 (en) * | 2013-08-30 | 2015-03-05 | Yale University | Therapeutic dnp derivatives and methods using same |
| WO2015105514A1 (en) * | 2014-01-13 | 2015-07-16 | Unipixel Displays, Inc. | Coated nano-particle catalytically active composite inks |
| CN104058652A (en) * | 2014-05-29 | 2014-09-24 | 安徽华塑股份有限公司 | High-strength concrete and preparation method thereof |
| CN104642326A (en) * | 2015-02-16 | 2015-05-27 | 河南科技学院 | Fungicidal composition containing penflufen and carvacrol and use of fungicidal composition |
| CN104862072A (en) * | 2015-05-08 | 2015-08-26 | 湖南红星盛康油脂股份有限公司 | Tea seed oil refining process |
Non-Patent Citations (4)
| Title |
|---|
| Development and comparison of two dispersive liquid-liquid microextraction techniques coupled to high performance liquid chromatography for the rapid analysis of bisphenol A in edible oils;Shuhui Liu等;《Journal of Chromatography A》;20131231;摘要，表2 * |
| Silica from hydrolysis and condensation of sodium metasilicate in bicontinuous microemulsions;K. Zhang等;《Materials Chemistry and Physics》;19971231;第164-170页 * |
| 沉积物中***及壬基酚、辛基酚、双酚 A 的测定;吴唯等;《环境科学》;20130228;第725页第2段，第730页第3结论 * |
| 液相色谱-串联质谱法测定ARA & DHA油脂中的壬基酚;李翔宇;《食品科技》;20161231;第41卷(第4期);第292页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108611189A (en) | 2018-10-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6166231A (en) | Two phase extraction of oil from biomass | |
| US9745537B2 (en) | Process for the extraction of lipids from algal biomass | |
| US8535397B2 (en) | Process for the extraction of fatty acids from algal biomass | |
| US20100227042A1 (en) | Enzyme-Assisted De-Emulsification of Aqueous Lipid Extracts | |
| CN104694250B (en) | Method for reducing 3-MCPD ester and/or glycidyl ester in grease | |
| AU2020217361B2 (en) | Oil purification process | |
| Wroniak et al. | Comparison of the quality of cold pressed and virgin rapeseed oils with industrially obtained oils | |
| JP2014534567A (en) | Liquid compositions used as insulation and heat transfer means, electrical devices containing said compositions, and methods for preparing such compositions | |
| EP1624047A1 (en) | Oil recuperation process | |
| Choi et al. | Acid-catalyzed hot-water extraction of docosahexaenoic acid (DHA)-rich lipids from Aurantiochytrium sp. KRS101 | |
| CN102504950A (en) | Method for decolorizing tea seed oil | |
| WO2001062880A1 (en) | Process for preparing blown vegetable oil | |
| CN103131529B (en) | A kind of method extracting microbial oil | |
| EP3519539B1 (en) | Water treatment of lipid material | |
| CN108611189B (en) | Refining process for controlling bisphenol A and alkylphenol in grease | |
| Evangelista | Oil extraction from lesquerella seeds by dry extrusion and expelling | |
| CN105733803B (en) | Method for treating grease | |
| Ghouila et al. | Vegetable oils and fats: Extraction, composition and applications | |
| CN113755240A (en) | Method for removing trichloropropanol ester and glycidyl ester in palm oil | |
| Bahmaei et al. | Development of a method for chlorophyll removal from canola oil using mineral acids | |
| CN105010721A (en) | Multi-step coupling method to prepare concentrated phospholipids with a high transparency | |
| Peri | The olive oil refining process | |
| US9296977B2 (en) | Method for producing fatty acid composition | |
| CN110923058A (en) | Method for controlling harmful substances in edible vegetable oil | |
| CN103540410B (en) | A kind of preparation method of main byproduct of rice oil |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |