CN117106108A - Supermolecule eutectic solvent and preparation method and application thereof - Google Patents
Supermolecule eutectic solvent and preparation method and application thereof Download PDFInfo
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- CN117106108A CN117106108A CN202311063955.7A CN202311063955A CN117106108A CN 117106108 A CN117106108 A CN 117106108A CN 202311063955 A CN202311063955 A CN 202311063955A CN 117106108 A CN117106108 A CN 117106108A
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- eutectic solvent
- edible oil
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- 230000005496 eutectics Effects 0.000 title claims abstract description 62
- 239000002904 solvent Substances 0.000 title claims abstract description 55
- 238000002360 preparation method Methods 0.000 title abstract description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 63
- 239000008157 edible vegetable oil Substances 0.000 claims abstract description 55
- 239000010949 copper Substances 0.000 claims abstract description 35
- 229910052802 copper Inorganic materials 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 34
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 33
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims abstract description 33
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000011701 zinc Substances 0.000 claims abstract description 32
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 32
- 239000011572 manganese Substances 0.000 claims abstract description 31
- 229910052742 iron Inorganic materials 0.000 claims abstract description 30
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 30
- 239000007788 liquid Substances 0.000 claims abstract description 24
- 230000029087 digestion Effects 0.000 claims abstract description 19
- 238000005516 engineering process Methods 0.000 claims abstract description 14
- 239000006185 dispersion Substances 0.000 claims abstract description 12
- 238000004853 microextraction Methods 0.000 claims abstract description 12
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 36
- 229910017604 nitric acid Inorganic materials 0.000 claims description 25
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 24
- 239000011573 trace mineral Substances 0.000 claims description 21
- 235000013619 trace mineral Nutrition 0.000 claims description 21
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 claims description 19
- 229960000448 lactic acid Drugs 0.000 claims description 18
- 238000010438 heat treatment Methods 0.000 claims description 15
- 229920000858 Cyclodextrin Polymers 0.000 claims description 8
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 239000010775 animal oil Substances 0.000 claims description 4
- 238000001514 detection method Methods 0.000 abstract description 16
- 238000000605 extraction Methods 0.000 abstract description 16
- 238000009616 inductively coupled plasma Methods 0.000 abstract description 13
- 230000008569 process Effects 0.000 abstract description 8
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 5
- 229910021654 trace metal Inorganic materials 0.000 abstract description 5
- 238000000295 emission spectrum Methods 0.000 abstract description 4
- 230000007547 defect Effects 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 27
- 238000004458 analytical method Methods 0.000 description 13
- 239000000523 sample Substances 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 238000011084 recovery Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000011550 stock solution Substances 0.000 description 8
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 7
- 229910021645 metal ion Inorganic materials 0.000 description 7
- 235000015112 vegetable and seed oil Nutrition 0.000 description 7
- 239000008158 vegetable oil Substances 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- 239000012488 sample solution Substances 0.000 description 6
- 235000019484 Rapeseed oil Nutrition 0.000 description 5
- -1 hydrogen ions Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 235000012424 soybean oil Nutrition 0.000 description 5
- 239000003549 soybean oil Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000012086 standard solution Substances 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 239000012491 analyte Substances 0.000 description 3
- 229960004543 anhydrous citric acid Drugs 0.000 description 3
- 238000013478 data encryption standard Methods 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000004993 emission spectroscopy Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000120 microwave digestion Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000002211 L-ascorbic acid Substances 0.000 description 2
- 235000000069 L-ascorbic acid Nutrition 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229910021642 ultra pure water Inorganic materials 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- 238000000209 wet digestion Methods 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 229910001297 Zn alloy Inorganic materials 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000004380 ashing Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 229940013688 formic acid Drugs 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000002957 persistent organic pollutant Substances 0.000 description 1
- 238000004094 preconcentration Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000002133 sample digestion Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000019614 sour taste Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000013582 standard series solution Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/71—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light thermally excited
- G01N21/73—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light thermally excited using plasma burners or torches
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Molecular Biology (AREA)
- Pathology (AREA)
- Immunology (AREA)
- General Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Plasma & Fusion (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
The application discloses a supermolecule eutectic solvent, a preparation method and application thereof, and belongs to the technical field of trace metal element detection. The application overcomes the defect of large organic reagent amount used in the traditional extraction technology, and provides a method for simultaneously detecting four microelements of copper, zinc, iron and manganese in edible oil by combining an ultra-molecular eutectic solvent-dispersion liquid microextraction technology and an inductively coupled plasma emission spectrum technology through an digestion process of indirectly removing edible oil through enrichment.
Description
Technical Field
The application belongs to the technical field of trace metal element detection, and particularly relates to an supermolecule eutectic solvent, a preparation method and application thereof.
Background
The edible vegetable oil is used as a key component in the dietary structure of residents in China, the safety of the edible vegetable oil is widely concerned, the content of trace elements in the vegetable oil plays an important role in the freshness, storage and safety of the edible vegetable oil, and some trace metals (such as Cu and Fe) can directly react with lipid to generate lipid alkyl free radicals to generate active oxygen, and the automatic oxidation of the edible vegetable oil can be accelerated through the decomposition of hydrogen peroxide. Therefore, detecting the content and the variety of trace elements in the vegetable oil plays an important role in correctly knowing the edible safety and the nutritional value of people.
In edible vegetable oil trace element determination, the traditional pretreatment method mainly comprises wet digestion, microwave digestion, high-pressure digestion tank digestion, dry ashing digestion and the like. The organic matter content of the vegetable oil such as peanut oil, soybean oil, rapeseed oil and the like is too high, and dangerous accidents such as explosion and the like are extremely easy to occur when perchloric acid and nitric acid are added for digestion in a wet method, even if nitric acid is added for pre-digestion overnight, the vegetable oil still has higher danger, and the digestion time is longer. In addition, the volume of the digested sample is too small, so that the accuracy is influenced, and the volume is too large, so that carbonization is easy, and the overall experimental process is influenced.
The eutectic solvent (Deep eutectic solvent, DES) is a novel green solvent formed by hydrogen bonding of a hydrogen bond donor (Hydrogen bond donor, HBD) and a hydrogen bond acceptor (Hydrogen bond acceptor, HBA) which are mixed at a certain molar ratio at a certain temperature. When using natural substances as components, the DES formed is called natural eutectic solvents (Natural deep eutectic solvent, NADES), and with further development in recent years, supermolecular deep eutectic solvents (Supramolecular deep eutectic solvents, SUPRADESs) have emerged, which are a novel subclass of eutectic solvents characterized by inclusion compounds, a new finding that has an important impact on green chemistry development.
SUPRADESs have a number of unique properties, as compared to common organic agents, such as literatureThe known SUPRADESs of (a) consists of a green component, which has physicochemical properties similar to those of conventional des, and which has supramolecular properties allowing selective binding of many compounds, in many applications SUPRADESs shows a higher efficiency than des. Due to the inclusion of cyclodextrins in their structure, these solvents are able to bind many compounds through the formation of hydrogen bonds while interacting with their host-guest mechanism. The combination of the environmental protection properties of DESs and cyclodextrin is expected to be a breakthrough in the field of green chemistry. SUPRADESs can be used as nano synthetic materials in the field of inorganic chemistry due to their excellent properties; in the field of organic chemistry, it can be used for CO 2 Absorbing; in the analytical chemistry field, the method can replace organic reagents to be used in the pretreatment process of samples, extract volatile or semi-volatile organic pollutants and the like. However, the application of SUPRADESs to the detection of trace elements in edible oil has been recently reported.
Disclosure of Invention
The application aims to provide an supermolecule eutectic solvent, and a preparation method and application thereof, so as to solve the problems in the prior art. In order to reduce oxidation of edible oil in the processing and storage processes, the nutrition composition of essential trace elements in the edible oil is controlled as much as possible by detecting trace metal elements in the edible oil.
One of the technical schemes provided by the application is as follows:
the supermolecule eutectic solvent consists of cyclodextrin and organic acid, wherein the cyclodextrin is hydroxypropyl-beta-cyclodextrin, and the organic acid is DL-lactic acid.
Preferably, the mass ratio of the hydroxypropyl-beta-cyclodextrin to the DL-lactic acid is 1:4.
The second technical scheme provided by the application is as follows:
the preparation process of supermolecule eutectic solvent includes mixing hydroxypropyl-beta-cyclodextrin and DL-lactic acid, heating and stirring to homogeneous transparent liquid state.
Preferably, the heating temperature is 60-80 ℃ and the heating time is 20-30min.
The third technical scheme provided by the application is as follows:
the method for detecting trace elements in edible oil uses the supermolecule eutectic solvent as an extracting agent, and extracts copper, zinc, iron and manganese in the edible oil by using the supermolecule eutectic solvent-dispersion liquid microextraction technology.
The dispersion liquid-liquid microextraction technique (Dispersive liquid-liquid microextraction, DLLME) is a pretreatment method for miniaturized liquid-phase extraction. The extractant is dispersed into fine liquid drops in the sample solution through the strong dispersion capability of the extractant in the dispersing agent, so that an extractant-dispersing agent-sample solution three-phase emulsion system is formed, the contact area of the extractant and the analyte is increased, the analyte rapidly reaches the distribution balance between the sample solution and the extractant to complete extraction, and the extractant containing the analyte can be separated through centrifugation.
Preferably, the supermolecule eutectic solvent and the nitric acid solution are added into the edible oil, heated after vortex, centrifugally layered, digested by the mixed enrichment phase solution, and detected copper, zinc, iron and manganese in the edible oil extracted from the digestion solution.
The application adopts the supermolecule eutectic solvent-dispersion liquid microextraction technology to extract microelements in edible oil, wherein nitric acid solution is a dispersing agent, the supermolecule eutectic solvent shows strong dispersing ability in the nitric acid solution, and the nitric acid solution is dispersed into tiny liquid drops in the edible oil, so that a supermolecule eutectic solvent-nitric acid solution-edible oil three-phase emulsion system is formed, the contact area of the supermolecule eutectic solvent and the microelements is increased, the microelements are promoted to reach distribution balance between the edible oil and the supermolecule eutectic solvent rapidly, and the extraction is completed.
The hydrogen bond donor in the supermolecule eutectic solvent is DL-lactic acid, nitric acid solution is added during extraction, and the DL-lactic acid is used for abstracting hydrogen ions in carboxylic acid under an acidic environment, so that the number of carboxylate anions in a mixed water phase is increased, and coordination is easy to be generated with metal ions in edible oil. The hydroxypropyl-beta-cyclodextrin has a hydrophilic outer surface and a hydrophobic cavity, so that an inclusion compound can be formed in an aqueous solution, and a metal ion coordination product enters the cavity of the hydroxypropyl-beta-cyclodextrin, so that the solubility of the coordinated metal ion in a mixed aqueous phase is indirectly increased based on the host-guest interaction of the hydroxypropyl-beta-cyclodextrin, and the extraction stability of the metal ion is increased. In addition, the modified hydroxypropyl groups on the cyclodextrin derivative provide more complexing sites for metal ions, so that the adsorption capacity of the supermolecule eutectic solvent on the metal ions is further enhanced.
More preferably, the volume ratio of the edible oil, the supermolecule eutectic solvent and the nitric acid solution is 100-150:8:2.
The mass concentration of the nitric acid solution is 5wt%.
More preferably, the swirling time is 5min, the heating temperature is 75 ℃, and the heating time is 20min.
Preferably, the edible oil comprises edible vegetable oil and edible animal oil.
Preferably, the method for detecting copper, zinc, iron and manganese in the edible oil extracted from the digestion liquid is to detect the copper, zinc, iron and manganese simultaneously by an inductively coupled plasma emission spectroscopy technology.
Inductively coupled plasma emission spectroscopy (Inductively Coupled Plasma Optical Emission Spectrometer, ICP-OES) is widely used in microelement analysis at present, and the method realizes simultaneous determination of multiple elements, has a wider linear range and has shorter analysis time. The ICP-OES can meet the requirement of simultaneous determination of the content of most trace metal elements in the edible oil, and is a common analysis method in the inorganic element analysis technology at home and abroad at present.
The application has the beneficial effects that:
in the determination of trace elements of edible oil, whether dry digestion or wet digestion is carried out, cold digestion is carried out on the edible oil, then actual sample digestion is carried out, and the time is long.
The application adopts the supermolecule eutectic solvent-dispersion liquid microextraction technology to overcome the defects of complicated and time-consuming traditional liquid-liquid distribution operation, large consumption of toxic and harmful solvents, easy pollution to the environment and the like, has the advantages of less solvent consumption, high enrichment factor, high extraction efficiency, simple and convenient operation, rapidness, easy combination with various analysis instruments and the like, and has wide application prospect.
The application overcomes the defect of large organic reagent amount in the traditional extraction technology, and provides a method for simultaneously detecting four microelements of copper, zinc, iron and manganese in vegetable oil by combining an ultra-molecular eutectic solvent-dispersion liquid microextraction technology and an inductively coupled plasma emission spectrum technology through a digestion process of indirectly removing edible oil by enrichment.
The detection method of trace elements in the edible oil provided by the application can be applied to detection of four trace metal elements (copper, zinc, iron and manganese) in common various edible vegetable oils (soybean oil, corn oil, rapeseed oil and the like) or animal oils (such as butter or fish oil).
Drawings
In order to more clearly illustrate the embodiments of the present application or the technical solutions of the prior art, the drawings that are needed in the embodiments will be briefly described below, it being obvious that the drawings in the following description are only some embodiments of the present application, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a standard curve of copper element in example 1;
FIG. 2 is a standard curve of zinc element in example 1;
FIG. 3 is a standard curve of the iron element in example 1;
FIG. 4 is a standard curve of manganese element in example 1;
fig. 5 is a schematic diagram of the extraction process in example 2.
Detailed Description
Various exemplary embodiments of the application will now be described in detail, which should not be considered as limiting the application, but rather as more detailed descriptions of certain aspects, features and embodiments of the application.
It is to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. In addition, for numerical ranges in this disclosure, it is understood that each intermediate value between the upper and lower limits of the ranges is also specifically disclosed. Every smaller range between any stated value or stated range, and any other stated value or intermediate value within the stated range, is also encompassed within the application. The upper and lower limits of these smaller ranges may independently be included or excluded in the range.
Unless otherwise defined, 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 application belongs. Although only preferred methods and materials are described herein, any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present application. All documents mentioned in this specification are incorporated by reference for the purpose of disclosing and describing the methods and/or materials associated with the documents. In case of conflict with any incorporated document, the present specification will control.
It will be apparent to those skilled in the art that various modifications and variations can be made in the specific embodiments of the application described herein without departing from the scope or spirit of the application. Other embodiments will be apparent to those skilled in the art from consideration of the specification of the present application. The specification and examples of the present application are exemplary only.
As used herein, the terms "comprising," "including," "having," "containing," and the like are intended to be inclusive and mean an inclusion, but not limited to.
The room temperature of the present application means 25.+ -. 2 ℃.
The embodiment of the application provides an supermolecule eutectic solvent, which consists of cyclodextrin and organic acid, wherein the cyclodextrin is hydroxypropyl-beta-cyclodextrin, and the organic acid is DL-lactic acid.
Too much hydroxypropyl-beta-cyclodextrin is added to increase the viscosity of the obtained supermolecule eutectic solvent, which is unfavorable for the distribution of the subsequent supermolecule eutectic solvent in the sample solution, and too little hydroxypropyl-beta-cyclodextrin is added to decrease the extraction capacity of the obtained supermolecule eutectic solvent, so that the mass ratio of the hydroxypropyl-beta-cyclodextrin to the DL-lactic acid is preferably 1:4 in the embodiment of the application.
The embodiment of the application also provides a preparation method of the supermolecule eutectic solvent, which is to uniformly mix the hydroxypropyl-beta-cyclodextrin and the DL-lactic acid, heat and stir the mixture to a uniform transparent liquid state to obtain the supermolecule eutectic solvent.
Too low a heating temperature or too short a heating time may prevent adequate mixing of the hydroxypropyl-beta-cyclodextrin and the DL-lactic acid, and when the heating temperature exceeds 80 ℃ or the heating time exceeds 30min, the mixing degree of the hydroxypropyl-beta-cyclodextrin and the DL-lactic acid is not increased any more, so that in some preferred embodiments of the present application, the heating temperature is 60-80 ℃ for 20-30min.
According to the method, other supermolecule eutectic solvents are prepared, hydroxypropyl-beta-cyclodextrin is used as a hydrogen bond acceptor, DL-lactic acid, DL-malic acid, formic acid, acetic acid, anhydrous citric acid, L-ascorbic acid and the like are respectively used as hydrogen bond donors to synthesize various supermolecule eutectic solvents, experiments are carried out, the prepared different supermolecule eutectic solvents are placed for more than one week, the crystallization phenomenon of the DL-malic acid and the L-ascorbic acid occurs, and the supermolecule eutectic solvents prepared from the DL-lactic acid, the formic acid, the acetic acid and the anhydrous citric acid are proved to have good stability; however, formic acid and acetic acid have a sharp sour taste; in the synthesis process of anhydrous citric acid, a certain amount of aqueous solution is required to be added, and the comprehensive consideration is given to the fact that DL-lactic acid has the most remarkable effects of being simple and convenient to prepare, safe, green and the like.
The embodiment of the application also provides a detection method of trace elements in the edible oil, which takes the supermolecule eutectic solvent as an extractant, and extracts copper, zinc, iron and manganese in the edible oil by a supermolecule eutectic solvent-dispersion liquid microextraction technology.
In a preferred embodiment of the application, the supermolecule eutectic solvent and the nitric acid solution are added into edible oil, heated after vortex, centrifugally layered, the mixed enrichment phase solution is digested, and copper, zinc, iron and manganese in the edible oil extracted from the digestion solution are detected.
The excessive amount of nitric acid solution added will compete with the supermolecule eutectic solvent for metal ions, affecting the stability of the coordination product, and in order to achieve a higher preconcentration coefficient and shorter centrifugation time for the process, the volume ratio of edible oil, supermolecule eutectic solvent and nitric acid solution in the preferred embodiment of the present application is 100-150:8:2.
The mass concentration of the nitric acid solution in the preferred embodiment of the application is 5wt%.
Too short a vortex time does not favor the distribution of the eutectic solvent in the sample solution, too long a vortex time lengthens the detection procedure, so in some preferred embodiments of the application the vortex time is 5 minutes, the heating temperature is 75 ℃ and the heating time is 20 minutes.
In a preferred embodiment of the present application, the edible oil is edible vegetable oil or edible animal oil.
The reagents used in the examples of the present application were:
hydroxypropyl-beta-cyclodextrin, DL-lactic acid (racemization), nitric acid solution, copper element standard stock solution, zinc element standard stock solution, iron element standard stock solution, manganese element standard stock solution, perchloric acid, nitric acid, high-purity argon; all reagents were analytically pure and the whole experimental water was ultrapure water.
The apparatus used in the embodiment of the application is:
1) Inductively coupled plasma emission spectrometer ICP-OES: an Optima8000 inductively coupled plasma emission spectrometer, manufactured by PerkinElmer corporation, usa, was used, equipped with a TND1-10 type automatic ac voltage regulator, a W120D oil-free air compressor, a POLYSCIENCE WHISPERCOOL refrigerator; inductively coupled plasma emission spectroscopy conditions: sample lifting amount: 1mL; plasma gas flow rate: 15.0L/min; helper flow rate: 0.2L/min; atomizer gas flow rate: 0.55L/min; radio frequency power 1300W; analysis line: cu (324.752), zn (206.200), fe (259.939), mn (257.610);
2) A magnetic stirrer;
3) A constant temperature water bath kettle;
4) A vortex mixer;
5) 10mL pipette, 1000. Mu.L and 10. Mu.L pipette;
6) A microwave digestion instrument;
7) A 20mL centrifuge tube;
8) Refrigerated centrifuge.
Example 1
Method for detecting four microelements of copper, zinc, iron and manganese by inductively coupled plasma emission spectrometer ICP-OES (inductively coupled plasma-optical emission Spectrometry)
Drawing of a Standard Curve
Four trace element standard stock solutions of copper, zinc, iron and manganese with the concentration of 10mg/L are added into 5 50mL volumetric flasks of 0.05, 0.25, 0.50, 1.00, 2.50 and 5.00mL respectively, and 5wt% nitric acid is added to fix the volume, so that four trace element linear standard solutions of copper, zinc, iron and manganese with the concentration of 0.01, 0.05, 0.10, 0.20, 0.50 and 1.00mg/L are obtained.
Under the optimal working state of the inductively coupled plasma emission spectrum, the linear standard solutions with the concentrations are respectively put on a machine, the concentrations are measured for 3 times in parallel, the spectral line intensity y is taken as an ordinate, the concentration x is taken as an abscissa, a standard curve is drawn, a linear equation, a correlation coefficient and a linear range are shown in a table 1, fig. 1 is a standard curve of copper element, fig. 2 is a standard curve of zinc element, fig. 3 is a standard curve of iron element, and fig. 4 is a standard curve of manganese element.
TABLE 1
Labeling recovery and precision testing
In order to evaluate the accuracy and precision of detecting four microelements of copper, zinc, iron and manganese by an inductively coupled plasma emission spectrometer ICP-OES, four microelement standard solutions of copper, zinc, iron and manganese with low concentration and high concentration are prepared, and each standard solution is measured for 5 times and the recovery rate is calculated.
RSD of recovery obtained by parallel analysis of 5 times of the labeled sample within 1 day for intra-day precision, RSD of recovery obtained by repeated analysis of the labeled sample for 5 consecutive days for inter-day precision.
As can be seen from Table 2, the recovery rates of copper, zinc and manganese are 99.2-123.8%, the recovery rate of iron is 52.0-66.4%, the daily RSD is 1.4-3.7%, the daily RSD is 2.6-5.4%, and the daily RSD is less than 5.4%.
TABLE 2
Example 2
The four microelements of copper, zinc, iron and manganese in the vegetable oil are measured by combining an ultra-molecular eutectic solvent-dispersion liquid microextraction technology with an inductively coupled plasma emission spectrometer.
Preparation of supermolecule eutectic solvent: 1g of hydroxypropyl-beta-cyclodextrin (purchased from Shanghai Meilin Biotechnology Co., ltd.) and 4g of DL-lactic acid were weighed, added into a 5mL volumetric flask, mixed well, heated and stirred at 60 ℃ for 20min by a constant temperature magnetic stirrer until a pale yellow, uniform and transparent liquid state was formed, cooled to room temperature, and a supermolecule eutectic solvent was obtained for later use.
Preparation of 5wt% nitric acid solution: accurately sucking 5mL of nitric acid (high-grade pure), placing into a volumetric flask containing 50mL of ultrapure water, and uniformly mixing to 100mL.
Preparing a standard mixed solution of four microelements of copper, zinc, iron and manganese: the volumes of copper, zinc, iron and manganese listed in the volumes of the stock solutions required for preparing the standard series solutions are accurately absorbed by the standard stock solutions of each element (the concentration is 1000 mug/mL, a single standard purchased by the national standard center), the standard stock solutions are placed in a 100mL volumetric flask, the volume is accurately fixed by using a 5wt% nitric acid solution to prepare an intermediate solution of 1 mug/mL, and then the intermediate solution is absorbed by the volumes of copper, zinc, iron and manganese listed in Table 3 to prepare a standard mixed solution of copper, zinc, iron and manganese. And transferring the obtained standard mixed solution into a polyethylene bottle, and placing the polyethylene bottle in a refrigerator for light-shielding preservation.
TABLE 3 Table 3
5 series concentration gradient solutions of four trace elements of copper, zinc, iron and manganese are prepared according to the concentration gradients of the four trace elements of copper, zinc, iron and manganese in table 4, detection is carried out, standard graphs of the elements are drawn according to the obtained data, and the normal line performance is good in the range of 0-5000 mug/L due to the wider linearity of ICP-OES, and the correlation coefficient reaches more than 0.999.
TABLE 4 Table 4
And drawing a standard curve, then sampling and detecting sample analysis liquid, and comparing the obtained result with the standard curve of each element to obtain the concentration of the liquid to be detected.
The edible oil used in this embodiment is: fresh soybean oil (purchased in local supermarket) and rapeseed oil (obtained by mechanical pressing)
Extraction procedure: copper, zinc, iron and manganese in the extracted edible oil are taken through a supermolecule eutectic solvent-dispersion liquid microextraction technology, 10mL of the edible oil is absorbed by using a 10mL pipetting gun, the edible oil is placed into a 20mL transparent centrifuge tube, 800 mu L of supermolecule eutectic solvent (extractant) and 200 mu L of 5wt% nitric acid solution (dispersing agent) are added, vortex is carried out for 5min (whole is cream yellow), the mixture is heated by a constant temperature water bath kettle at 75 ℃ for 20+/-2 min until the oil phase and supermolecule eutectic solvent phase are primarily layered, then centrifugal layering (800 rpm,5 min) is carried out, after the mixture is stabilized, immediately, 0.2mL of lower mixed enriched phase solution is absorbed by using a 1000 mu L pipetting gun and placed into a digestion tube, 8mL of nitric acid and 2mL of perchloric acid are added for microwave digestion, the digestion solution is finally subjected to constant volume to 10mL by pure water, so as to obtain sample analysis liquid, the sample analysis liquid is subjected to element analysis by an inductive coupling plasma emission spectrum system, the trace element content in the sample solution is calculated through the standard curve, and the extraction process is shown in figure 5.
Detection result: the content of trace elements in the edible oil sample is calculated by using the content of each element in the sample analysis liquid, the dilution factor and the moisture content in the sample, and the result is shown in Table 5.
TABLE 5
| Copper (mug/g) | Zinc (mug/g) | Iron (mu g/g) | Manganese (mug/g) | |
| Fresh soybean oil | 2.64 | 4.45 | 21.20 | 0.48 |
| Rapeseed oil | 2.62 | 4.33 | 21.77 | 0.47 |
Determination of detection and quantification limits
The detection limit and the quantitative limit are calculated according to the standard deviation of 3 times and 10 times, and the calculation method comprises the following steps: the standard deviation was calculated by the instrument by repeating the detection of the blank substrate after the standard curve was drawn, the standard deviation was converted into the concentration as the detection limit by 3 times, and the concentration as the quantitative limit by 10 times, as shown in table 6.
TABLE 6
| Microelements | Detection limit (μg/L) | Quantitative limit (μg/L) |
| Copper (Cu) | 0.98 | 3.23 |
| Zinc alloy | 1.24 | 4.09 |
| Iron (Fe) | 4.50 | 14.85 |
| Manganese (Mn) | 1.30 | 4.29 |
As shown in Table 6, four microelements of copper, zinc, iron and manganese in vegetable oil are measured by the supermolecule eutectic solvent-dispersion liquid microextraction technology combined with an inductively coupled plasma emission spectrometer, the detection limit is 0.98-4.50 mug/L, and the quantitative limit is 3.23-14.85 mug/L. According to the method, a small amount of supermolecule eutectic solvent is added to enrich trace elements in the oil sample, and a trace amount of 5wt% nitric acid solution is added to reduce the viscosity of the supermolecule eutectic solvent, so that the cold digestion process of the digestion program on the edible oil is removed, the operation steps are simplified, meanwhile, the direct digestion on the edible oil is avoided, and the enrichment factor (the concentration of the sample before extraction divided by the concentration of the extraction phase after extraction) of the established method is 10, so that the method has better sensitivity and lower detection limit.
Recovery and precision determination by labelling recovery
10mL of fresh soybean oil and rapeseed oil samples were transferred to centrifuge tubes, respectively, and copper, zinc, manganese and iron standard mixed solutions of low, medium and high concentrations were added respectively as shown in Table 7, and the extraction procedure was performed as described above, and the average value was calculated three times for each concentration, and the average recovery rate was obtained, and the results are shown in Table 7.
TABLE 7
As is clear from Table 7, the recovery rates of copper, zinc and manganese were 99.1% or more, and the maximum iron content was 64.2%.
The above embodiments are only illustrative of the preferred embodiments of the present application and are not intended to limit the scope of the present application, and various modifications and improvements made by those skilled in the art to the technical solutions of the present application should fall within the protection scope defined by the claims of the present application without departing from the design spirit of the present application.
Claims (9)
1. The supermolecule eutectic solvent consists of cyclodextrin and organic acid, and is characterized in that the cyclodextrin is hydroxypropyl-beta-cyclodextrin and the organic acid is DL-lactic acid.
2. An supramolecular eutectic solvent according to claim 1, wherein the mass ratio of hydroxypropyl- β -cyclodextrin to DL-lactic acid is 1:4.
3. A method for preparing a supermolecule eutectic solvent, which is characterized in that the hydroxypropyl-beta-cyclodextrin and DL-lactic acid in claim 1 or 2 are uniformly mixed, heated and stirred to be in a uniform transparent liquid state, so as to obtain the supermolecule eutectic solvent.
4. A method for preparing an supramolecular eutectic solvent according to claim 3, wherein the heating temperature is 60-80 ℃ for 20-30min.
5. The method for detecting trace elements in edible oil is characterized in that the supermolecule eutectic solvent as claimed in claim 1 or 2 is used as an extractant, and copper, zinc, iron and manganese in the edible oil are extracted by the supermolecule eutectic solvent-dispersion liquid microextraction technology.
6. The method for detecting trace elements in edible oil according to claim 5, wherein the supermolecule eutectic solvent and the nitric acid solution are added into the edible oil, heated after vortex, centrifugally layered, and the mixed enrichment phase solution is digested, so that copper, zinc, iron and manganese in the edible oil extracted from the digestion solution are detected.
7. The method for detecting trace elements in edible oil according to claim 6, wherein the volume ratio of the edible oil, the supermolecule eutectic solvent and the nitric acid solution is 100-150:8:2.
8. The method for detecting trace elements in edible oil according to claim 6, wherein the vortex time is 5min, the heating temperature is 75 ℃, and the heating time is 20min.
9. The method for detecting trace elements in edible oil according to claim 6, wherein the edible oil comprises edible vegetable oil and edible animal oil.
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