CN115216330A - Method for separating nitrogen-containing compounds in oil products - Google Patents
Method for separating nitrogen-containing compounds in oil products Download PDFInfo
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- CN115216330A CN115216330A CN202210853623.8A CN202210853623A CN115216330A CN 115216330 A CN115216330 A CN 115216330A CN 202210853623 A CN202210853623 A CN 202210853623A CN 115216330 A CN115216330 A CN 115216330A
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- nitrogen
- oil
- containing compounds
- quaternary ammonium
- oil products
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- 238000000034 method Methods 0.000 title claims abstract description 38
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 239000000126 substance Substances 0.000 claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 13
- 238000000605 extraction Methods 0.000 claims abstract description 12
- 230000005496 eutectics Effects 0.000 claims abstract description 8
- 238000011084 recovery Methods 0.000 claims abstract description 8
- 238000002474 experimental method Methods 0.000 claims abstract description 5
- 230000000694 effects Effects 0.000 claims abstract description 3
- 230000035484 reaction time Effects 0.000 claims abstract description 3
- 238000004064 recycling Methods 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims description 9
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical class [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical class [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims 1
- 235000019743 Choline chloride Nutrition 0.000 claims 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical class [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 claims 1
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical class [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims 1
- 229960003178 choline chloride Drugs 0.000 claims 1
- 229910017464 nitrogen compound Inorganic materials 0.000 claims 1
- 150000002830 nitrogen compounds Chemical class 0.000 claims 1
- 238000000638 solvent extraction Methods 0.000 abstract description 2
- 238000000622 liquid--liquid extraction Methods 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 31
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 16
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 16
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 8
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 150000004767 nitrides Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- -1 nitrogen-containing compound Chemical class 0.000 description 3
- 238000004088 simulation Methods 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002199 base oil Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- PBVWVLGUNLKLLC-UHFFFAOYSA-N dodecane;methane Chemical compound C.CCCCCCCCCCCC PBVWVLGUNLKLLC-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Extraction Or Liquid Replacement (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
The invention discloses a method for separating nitrogen-containing compounds in oil products. In the method, one or more quaternary ammonium salts are used as an extracting agent, and nitrogen-containing substances are extracted from simulated oil through a liquid-liquid extraction experiment; the influence of the quaternary ammonium salt type, the agent-oil ratio, the reaction temperature and the reaction time on the removal effect of the nitrogen-containing compounds in the simulated oil and the influence of the type of the back-extraction agent and the recycling frequency on the recovery rate of the quaternary ammonium salt are researched, and the result shows that the eutectic synthesis method formed by the quaternary ammonium salt and the nitrogen-containing compounds in the oil is a green chemical method with high selectivity and high extraction efficiency for removing the nitrogen-containing substances in the oil product.
Description
[ technical field ] A method for producing a semiconductor device
The invention belongs to the field of chemical separation and purification, and particularly relates to a method for separating nitrogen-containing compounds in oil products.
[ background of the invention ]
Crude oil has been one of the major energy sources needed globally for many years. Crude oil, however, contains many impurities, one of the most common of which is nitrogen-containing species. The oil products contain rich nitrides, such as indole, aniline, pyridine, quinoline, and the like, the nitrogen-containing compounds are harmful impurities from the aspect of preparing liquid fuel by processing the oil products, can affect the properties of the oil products, and cause catalyst poisoning in the processing processes of cracking, hydrogenation, and the like, and meanwhile, the nitrogen-containing substances are organic chemical industrial raw materials and intermediates, and are widely applied to the synthesis of fibers and plastics, the preparation of pesticides and medicines, and other production fields of spices, dyes, and the like. The separation of nitrogen-containing species from oil products has therefore led to extensive research.
The traditional method for separating nitride from oil is an acid washing method, but the whole process consumes a large amount of acid-base solution, and can generate partial acid residue and alkali residue which are difficult to process subsequently, the solvent extraction method can separate the nitrogen-containing compound, but the selectivity is poor, the yield of refined oil is low, the energy consumption for recovering the solvent is large, the adsorption refining method is usually small in adsorption capacity, and the denitrification rate cannot meet the industrial requirement. It is necessary to research a novel method for separating the nitride in the oil product.
Organic solvents are traditional extractants, but the solvents have the defects of high toxicity, flammability and explosiveness and the like. With the development of science and technology and the requirement of national major development strategy, researchers find that eutectic solvents have many advantages as green solvents. The application of the low eutectic method has the characteristics of simple process, low cost, biodegradability of the generated eutectic, environmental friendliness, small volatility, insensitivity to water, strong designability and the like, and the method is really in line with the green chemical concept.
Therefore, providing a method for separating nitrogen-containing compounds from oil products has become an urgent technical problem in the art.
[ summary of the invention ]
[ problem to be solved ]
To address the above-described disadvantages and drawbacks, it is an object of the present invention to provide a method for separating nitrogen-containing compounds in an oil product.
In order to achieve the purpose, the invention provides a method for separating nitrogen-containing compounds in oil products, which selects four quaternary ammonium salts as extracting agents and separates nitrogen-containing substances in the oil by forming eutectic solvents with the nitrogen-containing compounds.
Wherein the ratio of the extracting agent to the nitrogen-containing substances is 2;
the extraction separation temperature was room temperature (25 ℃).
The invention is realized by the following technical scheme.
(1) Preparing simulation oil required by experiment
Taking n-dodecane and toluene as base oil, adding indole, aniline, pyridine and quinoline as target nitrides, and simultaneously adding biphenyl as an internal standard substance to prepare experimental simulation oil.
(2) Extraction Experimental Process
Adding a certain volume of simulated oil and a certain mass of quaternary ammonium salt into a conical flask with a condensing device, magnetically stirring at a constant temperature at a certain reaction temperature for reaction time, and standing for clear layering. And taking the upper oil layer for gas chromatographic analysis.
(3) Investigating optimum operating conditions
In the conical flask with condensing unit, the optimum experimental conditions were selected by varying the temperature, the ratio of extractant to simulated oil, and the extraction time.
The ratio of the extracting agent to the nitrogen-containing substances is 2.
(4) Efficiency of recovery
Proper amount of back extractant is selected to recover tetraethyl ammonium chloride as extractant, and the final recovery rate is 95.7%.
[ advantageous effects ]
Compared with the prior art, the invention has the following beneficial effects:
(1) The method adopts the eutectic solvent formed by the extracting agent and the nitrogen-containing compound to separate the nitrogen-containing substance in the oil, and the method directly uses the quaternary ammonium salt as the extracting agent to extract the nitrogen-containing compound, thereby effectively reducing the cost of the raw material of the extracting agent.
(2) The invention can make the recovery rate of the extracted quaternary ammonium salt reach more than 95 percent by using a simple recovery method.
(3) The invention uses quaternary ammonium salt as an extracting agent, and has the advantages of low energy consumption, simple process and the like. The method for forming the eutectic solvent by the extractant and the nitrogenous substance has the advantages of high extraction efficiency, environmental protection, low price and the like.
[ description of the drawings ]
FIG. 1 is a schematic diagram of the structure of an extraction experiment apparatus used in the present invention.
In the figures, the reference numerals are:
1. constant temperature reaction kettle
2. Condenser tube
3. Liquid-liquid reaction kettle
4. Stirring instrument
5. Stirrer
6. Extraction bottle
7. Iron stand
[ detailed description ] embodiments
Example 1:
the embodiment provides a method for separating nitrogen-containing compounds in oil products, which comprises the following steps:
taking 500ml of dodecane methane and toluene as base oil, adding a certain amount of indole, aniline, pyridine and quinoline, adding biphenyl as an internal standard substance to prepare experimental simulation oil, and enabling the mass fractions of the indole, the aniline, the pyridine and the quinoline to be respectively 500ug/g. The experimental process is as follows:
adding the simulated oil into a 500ml conical flask, wherein the conical flask is double-layer, circulating water is introduced into the outer layer to ensure that the temperature is constant in the extraction process, and a solvent is added into the inner layer. Adding an extractant (quaternary ammonium salt) which is prepared with the simulated oil according to a certain proportion into a conical flask at a fixed temperature (in a constant-temperature reaction kettle). Opening a constant temperature reaction kettle, and then carrying out an extraction denitrification experiment by using a magnetic stirrer. After a certain stirring time, the stirring was stopped. And after standing for a period of time, when obvious layering occurs on the upper layer and the lower layer of the solution, taking an upper layer sample for gas chromatography analysis.
Example 2:
the embodiment provides a method for separating nitrogen-containing compounds in oil products, which comprises the following steps:
adding 150ml of simulated oil into a 500ml conical flask, adding 50ml of extracting agent, controlling the temperature of a constant-temperature reaction kettle to be 30 ℃, opening the constant-temperature reaction kettle, and stirring for 20min by using a magnetic stirrer. After standing for a period of time, taking an upper layer sample for gas chromatography analysis.
The measurement result shows that: the upper nitrogen-containing substance comprises 98% of indole, 91.2% of aniline, 54% of pyridine and 60% of quinoline.
Example 3:
the embodiment provides a method for separating nitrogen-containing compounds in oil products, which comprises the following steps:
adding 150ml of simulated oil into a 500ml conical flask, adding 50ml of extracting agent, controlling the temperature of a constant-temperature reaction kettle to be 40 ℃, opening the constant-temperature reaction kettle, and stirring for 20min by using a magnetic stirrer. After standing for a period of time, the upper sample was taken for gas chromatography.
The measurement result shows that: the upper nitrogen-containing substance had a concentration of 96.7% indole, 89.6% aniline, 46.8% pyridine and 54.3% quinoline.
Example 4:
the embodiment provides a method for separating nitrogen-containing compounds in oil products, which comprises the following steps:
adding 150ml of simulated oil into a 500ml conical flask, adding 60ml of extracting agent, controlling the temperature of a constant-temperature reaction kettle to be 40 ℃, opening the constant-temperature reaction kettle, and stirring for 20min by using a magnetic stirrer. After standing for a period of time, the upper sample was taken for gas chromatography.
The measurement result shows that: the upper nitrogen-containing substance had a concentration of 99.4% indole, 93.1% aniline, 60.8% pyridine and 65.7% quinoline.
Example 5:
the embodiment provides a method for separating nitrogen-containing compounds in oil products, which comprises the following steps:
adding 150ml of simulated oil into a 500ml conical flask, adding 60ml of extracting agent, controlling the temperature of a constant-temperature reaction kettle to be 40 ℃, starting the constant-temperature reaction kettle, and stirring for 10min by using a magnetic stirrer. After standing for a period of time, taking an upper layer sample for gas chromatography analysis.
The measurement result shows that: the upper nitrogen-containing substance comprises 91.6% of indole, 82.2% of aniline, 40.8% of pyridine and 35.7% of quinoline.
Claims (6)
1. A method for separating nitrogen-containing compounds in oil products is characterized in that four quaternary ammonium salts are selected as extracting agents, and eutectic solvents are formed between the four quaternary ammonium salts and the nitrogen-containing compounds to separate the nitrogen-containing substances in the oil products;
wherein the ratio of the extracting agent to the nitrogen-containing substances is 2;
the extraction separation temperature was normal temperature (25 ℃).
2. The method of claim 1, wherein the ratio of the extractant to the nitrogen-containing species is 2.
3. The method of claim 1, wherein the basic and non-basic nitrogen compounds in the oil are separated by extraction.
4. The method for separating nitrogen-containing compounds in oil products according to claim 1, characterized in that four quaternary ammonium salts of choline chloride, tetramethylammonium chloride, tetraethylammonium chloride and hexadecyltrimethylammonium bromide are selected for denitrification experiments.
5. The method of claim 1, wherein the optimum denitrifying agent is tetraethylammonium chloride, and the optimum operating conditions are: the agent-oil ratio is 2, the reaction temperature is normal temperature, and the reaction time is 20min.
6. The method of claim 1, wherein the recovery and recycling of the extractant are high, the recovery effect of ethyl acetate on tetraethyl ammonium chloride is good, and the recovery rate of tetraethyl ammonium chloride after 5 times of circulation is 91.5%.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202210853623.8A CN115216330A (en) | 2022-07-11 | 2022-07-11 | Method for separating nitrogen-containing compounds in oil products |
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| CN202210853623.8A CN115216330A (en) | 2022-07-11 | 2022-07-11 | Method for separating nitrogen-containing compounds in oil products |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116836754A (en) * | 2023-05-29 | 2023-10-03 | 河南工业大学 | Method for removing heterocyclic amine from sesame oil |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5002655A (en) * | 1988-05-24 | 1991-03-26 | Director-General Of Agency Of Industrial Science And Technology | Process for the recovery of aromatic nitrogen-containing compounds |
| CN104762100A (en) * | 2015-03-30 | 2015-07-08 | 浙江大学 | Method for removing nitrogen-containing compounds in oil products by virtue of eutectic solvent extraction |
| CN106631967A (en) * | 2016-12-20 | 2017-05-10 | 北京化工大学 | Method for extraction separation of indole from washing oil by quaternary ammonium salt extraction agent |
| CN109181747A (en) * | 2018-09-21 | 2019-01-11 | 武汉工程大学 | A kind of eutectic solvent and its application method for fuel oil extraction denitrogenation |
| CN109679678A (en) * | 2018-12-27 | 2019-04-26 | 青岛科技大学 | Alkalinity/non basic nitrogen eutectic solvent and method are extracted from analog gasoline |
| CN109694723A (en) * | 2018-12-27 | 2019-04-30 | 青岛科技大学 | The eutectic solvent and method of non basic nitrogen are extracted from analog gasoline |
-
2022
- 2022-07-11 CN CN202210853623.8A patent/CN115216330A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5002655A (en) * | 1988-05-24 | 1991-03-26 | Director-General Of Agency Of Industrial Science And Technology | Process for the recovery of aromatic nitrogen-containing compounds |
| CN104762100A (en) * | 2015-03-30 | 2015-07-08 | 浙江大学 | Method for removing nitrogen-containing compounds in oil products by virtue of eutectic solvent extraction |
| CN106631967A (en) * | 2016-12-20 | 2017-05-10 | 北京化工大学 | Method for extraction separation of indole from washing oil by quaternary ammonium salt extraction agent |
| CN109181747A (en) * | 2018-09-21 | 2019-01-11 | 武汉工程大学 | A kind of eutectic solvent and its application method for fuel oil extraction denitrogenation |
| CN109679678A (en) * | 2018-12-27 | 2019-04-26 | 青岛科技大学 | Alkalinity/non basic nitrogen eutectic solvent and method are extracted from analog gasoline |
| CN109694723A (en) * | 2018-12-27 | 2019-04-30 | 青岛科技大学 | The eutectic solvent and method of non basic nitrogen are extracted from analog gasoline |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116836754A (en) * | 2023-05-29 | 2023-10-03 | 河南工业大学 | Method for removing heterocyclic amine from sesame oil |
| CN116836754B (en) * | 2023-05-29 | 2024-03-12 | 河南工业大学 | Method for removing heterocyclic amine from sesame oil |
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