CN113171752A - Method for eliminating biogenic amine by using metal organic framework material in fruit wine aging process - Google Patents
Method for eliminating biogenic amine by using metal organic framework material in fruit wine aging process Download PDFInfo
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- CN113171752A CN113171752A CN202110451030.4A CN202110451030A CN113171752A CN 113171752 A CN113171752 A CN 113171752A CN 202110451030 A CN202110451030 A CN 202110451030A CN 113171752 A CN113171752 A CN 113171752A
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- 150000001412 amines Chemical class 0.000 title claims abstract description 79
- 230000000035 biogenic effect Effects 0.000 title claims abstract description 57
- 230000032683 aging Effects 0.000 title claims abstract description 35
- 235000019990 fruit wine Nutrition 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 30
- 239000000463 material Substances 0.000 title claims abstract description 17
- 239000012621 metal-organic framework Substances 0.000 title claims abstract description 14
- 239000002105 nanoparticle Substances 0.000 claims abstract description 47
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 claims abstract description 44
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims abstract description 24
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims abstract description 24
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000005700 Putrescine Substances 0.000 claims abstract description 12
- 229960001340 histamine Drugs 0.000 claims abstract description 12
- 229960003732 tyramine Drugs 0.000 claims abstract description 12
- 230000008569 process Effects 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 238000001035 drying Methods 0.000 claims description 20
- 238000003483 aging Methods 0.000 claims description 14
- 239000002122 magnetic nanoparticle Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- 238000005406 washing Methods 0.000 claims description 11
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 8
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical group CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 5
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 5
- ZJKSNDSFYBPOFZ-UHFFFAOYSA-M ethyl-dimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;bromide Chemical compound [Br-].CC[N+](C)(C)CCOC(=O)C(C)=C ZJKSNDSFYBPOFZ-UHFFFAOYSA-M 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 4
- 229910000359 iron(II) sulfate Inorganic materials 0.000 claims description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- 239000008055 phosphate buffer solution Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 2
- 235000014101 wine Nutrition 0.000 abstract description 30
- 235000013305 food Nutrition 0.000 abstract description 6
- 238000000926 separation method Methods 0.000 abstract description 5
- 235000013334 alcoholic beverage Nutrition 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 abstract description 4
- 235000016709 nutrition Nutrition 0.000 abstract description 3
- 230000001953 sensory effect Effects 0.000 abstract description 3
- 230000008901 benefit Effects 0.000 abstract description 2
- 230000009257 reactivity Effects 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 18
- 238000000855 fermentation Methods 0.000 description 10
- 230000004151 fermentation Effects 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 239000008223 sterile water Substances 0.000 description 8
- 235000020104 cherry wine Nutrition 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- DMLLDBVPAZQXSS-UHFFFAOYSA-N 2-hydroxybutanedioic acid;2-hydroxypropanoic acid Chemical compound CC(O)C(O)=O.OC(=O)C(O)CC(O)=O DMLLDBVPAZQXSS-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 238000005352 clarification Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002077 nanosphere Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- 240000000249 Morus alba Species 0.000 description 2
- 235000008708 Morus alba Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 240000000851 Vaccinium corymbosum Species 0.000 description 2
- 235000003095 Vaccinium corymbosum Nutrition 0.000 description 2
- 235000017537 Vaccinium myrtillus Nutrition 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000021014 blueberries Nutrition 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WGTASENVNYJZBK-UHFFFAOYSA-N 3,4,5-trimethoxyamphetamine Chemical compound COC1=CC(CC(C)N)=CC(OC)=C1OC WGTASENVNYJZBK-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 208000000059 Dyspnea Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 244000111447 Rubus phoenicolasius Species 0.000 description 1
- 235000003963 Rubus phoenicolasius Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000009982 effect on human Effects 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 235000004280 healthy diet Nutrition 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 235000020061 kirsch Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- -1 nitrogen-containing organic bases Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000004729 solvothermal method Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000004916 vomit Anatomy 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/223—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material containing metals, e.g. organo-metallic compounds, coordination complexes
- B01J20/226—Coordination polymers, e.g. metal-organic frameworks [MOF], zeolitic imidazolate frameworks [ZIF]
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28002—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their physical properties
- B01J20/28009—Magnetic properties
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12H—PASTEURISATION, STERILISATION, PRESERVATION, PURIFICATION, CLARIFICATION OR AGEING OF ALCOHOLIC BEVERAGES; METHODS FOR ALTERING THE ALCOHOL CONTENT OF FERMENTED SOLUTIONS OR ALCOHOLIC BEVERAGES
- C12H1/00—Pasteurisation, sterilisation, preservation, purification, clarification, or ageing of alcoholic beverages
- C12H1/02—Pasteurisation, sterilisation, preservation, purification, clarification, or ageing of alcoholic beverages combined with removal of precipitate or added materials, e.g. adsorption material
- C12H1/04—Pasteurisation, sterilisation, preservation, purification, clarification, or ageing of alcoholic beverages combined with removal of precipitate or added materials, e.g. adsorption material with the aid of ion-exchange material or inert clarification material, e.g. adsorption material
- C12H1/0408—Pasteurisation, sterilisation, preservation, purification, clarification, or ageing of alcoholic beverages combined with removal of precipitate or added materials, e.g. adsorption material with the aid of ion-exchange material or inert clarification material, e.g. adsorption material with the aid of inorganic added material
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12H—PASTEURISATION, STERILISATION, PRESERVATION, PURIFICATION, CLARIFICATION OR AGEING OF ALCOHOLIC BEVERAGES; METHODS FOR ALTERING THE ALCOHOL CONTENT OF FERMENTED SOLUTIONS OR ALCOHOLIC BEVERAGES
- C12H1/00—Pasteurisation, sterilisation, preservation, purification, clarification, or ageing of alcoholic beverages
- C12H1/02—Pasteurisation, sterilisation, preservation, purification, clarification, or ageing of alcoholic beverages combined with removal of precipitate or added materials, e.g. adsorption material
- C12H1/04—Pasteurisation, sterilisation, preservation, purification, clarification, or ageing of alcoholic beverages combined with removal of precipitate or added materials, e.g. adsorption material with the aid of ion-exchange material or inert clarification material, e.g. adsorption material
- C12H1/0416—Pasteurisation, sterilisation, preservation, purification, clarification, or ageing of alcoholic beverages combined with removal of precipitate or added materials, e.g. adsorption material with the aid of ion-exchange material or inert clarification material, e.g. adsorption material with the aid of organic added material
Abstract
The invention discloses a method for eliminating biogenic amine by utilizing a metal organic framework material in the process of ageing fruit wine, which is characterized in that the metal organic framework material is added into the fruit wine in the process of ageing the fruit wine to remove biogenic amine in the fruit wine; the metal organic framework material is Fe3O4A nano-particle biological amine remover. The skeleton material has the advantages of high hydrophilicity, high reactivity, easy separation from a reaction system, repeatable utilization rate and the like, and can efficiently adsorb the wine body without negative influence on the nutritional composition and sensory characteristics of the wine bodyThe existence of histamine, putrescine and tyramine eliminates potential food safety hazards in fermented alcoholic beverages and enhances the market competitiveness of the products.
Description
Technical Field
The invention belongs to the field of ageing, and particularly relates to a method for eliminating biogenic amine by using a metal organic framework material in a fruit wine ageing process.
Background
Biogenic amines are a class of low molecular weight nitrogen-containing organic bases that are typically formed by decarboxylation of amino acids. Common alcoholic beverages such as wine, yellow wine, beer, etc. are rich in biogenic amines. The biogenic amines commonly existing in the fruit wine comprise histamine, tyramine, putrescine, phenethylamine, cadaverine and the like, and a proper amount of biogenic amines have certain promotion effect on human health, but when the content of biogenic amines is too high, the biogenic amines can generate toxic action on human bodies, so that the symptoms of hectic fever, blood pressure rise, arrhythmia, vomit, dyspnea, rash and the like appear on the human bodies, and even the life can be threatened. The three most toxic substances in the biogenic amines are histamine, tyramine and putrescine. In view of the toxicity and potential danger of biogenic amines, the development of relevant research on the strict control of biogenic amine content in food products is of great importance to ensure a healthy diet for people.
Magnetic Nanoparticles (MNPs) are a new type of nanomaterial that has been developed rapidly in recent decades, have good magnetic response under an applied magnetic field, are easy and convenient to prepare, are convenient for chemical modification, and have good biocompatibility, and are widely used in various industrial fields. The polymer Fe3O4 magnetic nanosphere is prepared from polymer and Fe3O4The compound with the size less than 100nm combined with the magnetic spheres has nanometer size, magnetic guidance and biocompatibility, is uniformly dispersed in a solution and can move along with the change of an external magnetic field, so that the compound can be quickly separated from a food system. In addition, the polymer can be connected with functional groups, so that the functionalization of the polymer magnetic nanospheres is quickly realized, the functions of the polymer magnetic nanospheres are widened, and the stability of the polymer magnetic nanospheres is enhanced.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a method for eliminating biogenic amine by using a metal organic framework material in the fruit wine aging process, so that the safety of the fruit wine is greatly improved, the market competitiveness of the product is enhanced, and the body health of a drinker is guaranteed.
The specific technical scheme is as follows:
a method for eliminating biogenic amine by using a metal organic framework material in the process of ageing fruit wine is different from the prior art in that the metal organic framework material is added into the fruit wine in the process of ageing the fruit wine to remove biogenic amine in the fruit wine; the metal organic framework material is Fe3O4A nano-particle biological amine remover.
The fruit wine is prepared by crushing fruits, squeezing, performing enzymolysis, performing alcoholic fermentation, performing malic acid and lactic acid fermentation (without the process, determined according to the characteristics of the fruit wine), clarifying, and aging.
Fruit wines sold in the market, including grape wine, cherry wine, blueberry wine, mulberry wine and the like, inevitably introduce or synthesize biogenic amine in the production process. The synthesis or accumulation of biogenic amine can be caused in multiple links of fruit wine brewing, such as raw material crushing, alcohol fermentation, malic acid lactic acid fermentation, clarification, aging and the like, but elimination in the link before aging can only ensure the effective control of a single link, and the recontamination of biogenic amine in the subsequent process cannot be controlled. Therefore, from the practical production point of view, the problem of biogenic amine accumulation caused by all the previous process steps (including raw material bringing, alcohol fermentation, malic acid lactic acid fermentation and clarification) can be solved at the same time in the process starting from the aging process.
The invention autonomously synthesizes a metal organic nanometer framework material, is characterized by being used for efficiently adsorbing histamine, tyramine and putrescine existing in a wine body in the aging process of the fruit wine on the premise of not having negative influence on the nutritional composition and the sensory characteristics of the wine body, has high efficiency and economy, eliminates potential food safety hazards in fermented alcoholic beverages, improves the safety of products, is an innovative proposal and a solution method for solving the problem that the biogenic amine content of the fruit wine exceeds the standard, and is worthy of popularization and application in the production process of the fruit wine.
Further, said Fe3O4The preparation method of the nano-particle biological amine remover comprises the following steps:
(1) preparation of Fe3O4Magnetic nanoparticles;
(2) preparation of functionalized Fe3O4Nanoparticles; the functional Fe3O4The nano particle is 3- (methacryloyloxy) propyl trimethoxy silane functionalized Fe3O4Nanoparticles;
(3) preparation of Fe with biogenic amine molecules as templates3O4A nano-particle biological amine remover.
Further, in the step (3), the biogenic amine molecules comprise one or more of histamine, tyramine and putrescine.
Further, step (1) is FeCl3·6H2O、FeSO4·4H2Preparation of Fe by taking O as raw material through solvothermal method3O4Magnetic nanoparticles; the specific working conditions are as follows:
the mass ratio of (2.5-2.8): 1 FeCl3·6H2O and FeSO4·4H2Dissolving O in water, adjusting the pH value to 11.0-12.0, stirring for 3-4 h at the temperature of 60-70 ℃, washing and separating the obtained product, and drying to obtain Fe3O4Magnetic nanoparticles.
Further, in the step (1), the pH is adjusted using ammonia water. The concentration of ammonia is preferably 25 wt%.
Still further, in the step (1), the washing is: washed three times with sterile water and ethanol in sequence.
Still further, in the step (1), the separation is: the product was isolated using a permanent magnet.
Still further, in the step (1), the drying is: drying in a drying oven at 40-45 ℃ for 6-12 h.
Still further, in the step (1), the water is preferably deionized water.
Further, the working conditions of the step (2) are as follows:
fe obtained in the step (1)3O4Dispersing magnetic nanoparticles in ethanol, adding 3- (methacryloyloxy) propyl trimethoxy silane, stirring at 35-45 ℃ for 10-12 h, washing, separating and drying the obtained product to obtain functional Fe3O4Nanoparticles.
Further, in the step (2), Fe3O4The dosage ratio of the magnetic nanoparticles to the 3- (methacryloyloxy) propyl trimethoxy silane is 100 mg: (2-3) mL.
Still further, in the step (2), the washing is: washed three times with sterile water and ethanol in sequence.
Still further, in the step (2), the separation is: the product was isolated using a permanent magnet.
Still further, in the step (2), the drying is: drying in a drying oven at 40-45 ℃ for 6-12 h.
Further, the working conditions of the step (3) are as follows:
functionalized Fe obtained in the step (2)3O4Mixing and dispersing nano particles, N-ethyl-2- (methacryloyloxy) -N, N-dimethylethylammonium bromide, acrylamide, N' -methylenebisacrylamide, ammonium persulfate, polyethylene glycol methyl methacrylate, tetramethylethylenediamine and biogenic amine molecules serving as a template in a phosphate buffer solution, continuously stirring for 24-28 h at 20-25 ℃, washing with sterile water to remove the template, separating out a product, and drying to obtain Fe3O4A nano-particle biological amine remover.
Further, in the step (3), Fe is functionalized3O4The dosage ratio of the nano particles, N-ethyl-2- (methacryloyloxy) -N, N-dimethylethylammonium bromide, acrylamide, N' -methylenebisacrylamide, ammonium persulfate, polyethylene glycol methyl methacrylate and tetramethylethylenediamine is 100 mg: (30-35) μ g: (150-165) mg: (10-11) mg: (9-10) mg: (15-17) μ L: (6-7) mu L.
Further, in the step (3), Fe is functionalized3O4The mass ratio of the nanoparticles to the biogenic amine molecules is (3-4) to 1.
Still further, in step (3), the phosphate buffer was 10.0mM and the pH was 7.0.
Further, in the step (3), Fe is functionalized3O4The dosage ratio of the nano particles to the phosphate buffer solution is 100 mg: (13-15) mL.
Still further, in the step (3), the washing is: washed three times with sterile water and ethanol in sequence.
Still further, in the step (3), the separation is: the product was isolated using a permanent magnet.
Still further, in the step (3), the drying is: drying in a drying oven at 40-45 ℃ for 6-12 h.
Further, said Fe3O4The specific using method of the nano-particle biological amine remover comprises the following steps:
in aging, adding 1-10 g/L Fe in terms of the volume of the fruit wine to be treated into the fruit wine3O4Reacting the nano-particle biogenic amine remover for 6-20h, and then using a permanent magnet to remove Fe3O4And recovering the nano-particle biological amine removing agent.
Further, adding Fe into the fruit wine 3-5 days before the aging3O4The nano-particle biological amine remover is used for removing biological amine.
Further, the recovered Fe3O4The nano-particle biological amine remover is washed with sterile water for 2-3 times, and can be used for removing biological amine and Fe in aged fruit wine3O4The nano-particle biological amine remover can be reused, and the total use times can reach 10-12 times.
Further, the fruit wine is grape wine, cherry wine, blueberry wine or mulberry wine.
The invention has the following beneficial effects:
the metal organic nanometer framework material is synthesized autonomously, is characteristically used in the aging process of fruit wine, has the advantages of high hydrophilicity, high reactivity, easy separation from a reaction system, repeatable utilization rate and the like, can efficiently adsorb histamine, putrescine and tyramine existing in wine on the premise of not having negative influence on the nutritional composition and sensory characteristics of the wine, eliminates potential food safety hazards in fermented alcoholic beverages, and enhances the market competitiveness of products. The invention is an innovative proposal and a solution for solving the problem of overproof biogenic amine content in fruit wine, and has wide application prospect in the field of food safety.
Detailed Description
The principles and features of this invention are described below in conjunction with examples, which are set forth to illustrate, but are not to be construed to limit the scope of the invention.
Example 1
1. Preparation of metal organic framework materials
(1) Preparation of Fe3O4Magnetic nanoparticles: 5.4g FeCl was weighed3·6H2O and 2.0g FeSO4·4H2O, dissolved in 100.0mL deionized water, and the pH is adjusted to 12.0 with ammonia (25 wt%); stirring the solution at 60 deg.C for 4h, sequentially washing the product with sterile water and ethanol for three times, separating the product with permanent magnet, and drying in drying oven at 40 deg.C for 12h to obtain Fe3O4Magnetic nanoparticles.
(2) Preparation of functionalized Fe3O4Nanoparticle: weighing 100mg of Fe obtained in step (1)3O4Dispersing the magnetic nanoparticles in 50.0mL of ethanol, and adding 2.0mL of 3- (methacryloyloxy) propyl trimethoxy silane to the solution; stirring the mixed solution at 45 ℃ for 10h, sequentially washing the product with sterile water and ethanol for three times, separating the product by using a permanent magnet, and drying the product in a drying oven at 40 ℃ for 12h to obtain functional Fe3O4Nanoparticles.
(3) Preparation of Fe3O4Nanoparticle biogenic amine remover: 100.0mg of functionalized Fe obtained in step (2)3O4Nanoparticles, 32.0. mu. g N-ethyl-2- (methacryloyloxy) -N, N-dimethylethylammonium bromide, 160.0mg acrylamide, 10mg N, N' -methylenebisacrylamide, 10.0mg ammonium persulfate, 16.0. mu.L polyethylene glycol methyl methacrylate, 6.4. mu.L tetramethylethylenediamine, 10mg histamine, 10mg tyramine, and 10mg putrescine were mixed and dispersed in 14.0mL phosphoric acid buffer (10.0mM, pH 7.0), continuously stirred at 20 ℃ for 28 hours, washed thoroughly, the template biogenic amine was removed, the product was isolated using a permanent magnet, and dried in a drying oven at 40 ℃ for 8 hours to obtain Fe3O4The nano-particle biological amine remover is named as Fe3O4@MIP。
2. Elimination of biogenic amines during wine aging
Selecting new wine obtained by crushing, squeezing, enzymolysis, alcoholic fermentation, malic acid lactic acid fermentation and clarification, and ageing the new wine at the temperature of 10 ℃. In that5g/L Fe in terms of the volume of the wine to be treated is added to the wine 5 days before the end of aging3O4Nanoparticle biogenic amine remover Fe3O4@ MIP, after 10h of reaction, the nanoparticle biogenic amine removal agent is recovered with a permanent magnet. The aging is carried out for 90 days.
Example 2
Fe obtained in example 1 was used3O4Nanoparticle biogenic amine remover Fe3O4@ MIP eliminates biogenic amines during the aging process of cherry wine.
Selecting new cherry wine obtained by crushing, squeezing, enzymolysis, alcoholic fermentation, malic acid lactic acid fermentation and clarification, and ageing the new cherry wine at the temperature of 15 ℃. Adding 8g/L Fe to the wine in terms of the volume of the wine to be treated 3 days before the end of aging3O4Nanoparticle biogenic amine remover Fe3O4@ MIP, after 8 hours of reaction, recovering the nano-particle biogenic amine removing agent by using a permanent magnet; the ageing lasts for 60 days.
Comparative example 1
Using the same wine as in example 1, aging was carried out at 10 ℃ for 90 days (the same aging conditions as in example 1) without carrying out the biogenic amine removal operation.
Comparative example 2
The same cherry wine as in example 2 was used and aged at 15 ℃ for 60 days (the same aging conditions as in example 2) without the removal of biogenic amine.
Test 1
The biogenic amine content of the wine bodies after aging of each example and each comparative example was tested and the results are shown in table 1.
TABLE 1 biogenic amine content after ageing of the examples and comparative examples
| Biogenic amines | Example 1 | Example 2 | Comparative example 1 | Comparative example 2 |
| Histamine (mg/L) | 0.68 | 0.54 | 2.93 | 2.71 |
| Tyramine (mg/L) | 0.97 | 0.7 | 5.33 | 4.48 |
| Putrescine (mg/L) | 0.25 | 0.33 | 1.8 | 2.15 |
The content of three biogenic amines in the example and comparative wine samples was tested. As is clear from the results of the examination, Fe was used in the examples3O4The nanoparticle biogenic amine remover causes the content of histamine, tyramine and putrescine to be reduced remarkably. Example 1 and comparative example 1 are both aged wines, and the amounts of histamine, tyramine and putrescine in example 1 are only 23.2%, 18.2% and 13.9% of comparative example 1, indicating that most of the biogenic amine has been Fe3O4Adsorbing by the nano-particle biological amine remover to remove. Example 2 and comparative example 2 are both aged kirschwasser, histamine, tyramine and putrescine in example 2Was only 19.9%, 15.6% and 15.3% of comparative example 2, again demonstrating Fe3O4Beneficial effects of the nanoparticle biogenic amine remover.
Test 2
The physicochemical indexes of the aged samples of the examples and the comparative examples were measured, and the results are shown in table 2.
TABLE 2 physicochemical indices after aging of examples and comparative examples
| Physical and chemical indexes | Example 1 | Example 2 | Comparative example 1 | Comparative example 2 |
| Total sugar (g/L) | 2.83 | 1.66 | 2.81 | 1.69 |
| Alcohol content (% vol) | 12.1 | 11.4 | 12.2 | 11.3 |
| pH | 3.40 | 3.68 | 3.41 | 3.67 |
| Total acid (g/L) | 5.15 | 8.05 | 5.22 | 8.14 |
| Volatile acid (g/L) | 0.43 | 0.39 | 0.50 | 0.43 |
Note: the total acid in wine (example 1 and comparative example 1) was calculated as tartaric acid and the total acid in cherry wine (example 2 and comparative example 2) was calculated as malic acid.
The basic physicochemical indexes of the wine samples of the examples and the comparative examples, including total sugar, alcohol content, pH, total acid and volatile acid, were examined. As can be seen from the results, the use of Fe compared to the naturally aged wine or cherry wine3O4All physical and chemical indexes of the wine sample treated by the nano-particle biological amine remover do not have obvious change, and only the indexes of total acid and volatile acid are slightly reduced, which shows that the metal framework organic material does not influence the composition and quality of the fruit wine.
Test 3
Carrying out Fe3O4The repeated use experiment of @ MIP verifies the repeated use effect.
Reference example 1 ageing conditions and Bioamine removal Process for Fe3O4Nanoparticle biogenic amine remover Fe3O4@ MIP was subjected to multiple use experiments. The experiment was carried out with wine fermented at the same time and aged at the same time, but in different aging tanks. Example 1 after completion of biogenic amine removal, Fe recovered3O4@ MIP was washed three times with sterile water and then used to ferment the same time, with simultaneous ageing, in other ageing pots without Fe being carried out3O4@ MIP treated wine was subjected to biogenic amine removal (for a longer time period, keeping biogenic amine removal occurring 5 days before the end of aging). By analogy, testing the repeatedly used Fe for many times3O4The effect of @ MIP on biogenic amine removal is shown in Table 3.
TABLE 3 Fe3O4Repeated use effect of @ MIP
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. A method for eliminating biogenic amine by using a metal organic framework material in the process of ageing fruit wine is characterized in that the metal organic framework material is added into the fruit wine in the process of ageing the fruit wine to remove biogenic amine in the fruit wine; the metal organic framework material is Fe3O4A nano-particle biological amine remover.
2. The method of claim 1, wherein said Fe is3O4The preparation method of the nano-particle biological amine remover comprises the following steps:
(1) preparation of Fe3O4Magnetic nanoparticles;
(2) preparation of functionalized Fe3O4Nanoparticles; the functional Fe3O4The nano particle is 3- (methacryloyloxy) propyl trimethoxySilane functionalized Fe3O4Nanoparticles;
(3) preparation of Fe with biogenic amine molecules as templates3O4A nano-particle biological amine remover.
3. The method according to claim 2, wherein in step (3), the biogenic amine molecules comprise one or more of histamine, tyramine, and putrescine.
4. The method according to claim 2, wherein the operating conditions of step (1) are:
the mass ratio of (2.5-2.8): 1 FeCl3·6H2O and FeSO4·4H2Dissolving O in water, adjusting the pH value to 11.0-12.0, stirring for 3-4 h at the temperature of 60-70 ℃, washing and separating the obtained product, and drying to obtain Fe3O4Magnetic nanoparticles.
5. The method of claim 2, wherein the operating conditions of step (2) are:
fe obtained in the step (1)3O4Dispersing magnetic nanoparticles in ethanol, adding 3- (methacryloyloxy) propyl trimethoxy silane, stirring at 35-45 ℃ for 10-12 h, washing, separating and drying the obtained product to obtain functional Fe3O4Nanoparticles.
6. The method of claim 5, wherein in step (2): fe3O4The dosage ratio of the magnetic nanoparticles to the 3- (methacryloyloxy) propyl trimethoxy silane is 100 mg: (2-3) mL.
7. The method according to claim 2, wherein the operating conditions of step (3) are:
functionalized Fe obtained in the step (2)3O4Nanoparticles, N-ethyl-2- (methacryloyloxy) -N, N-dimethylethylammonium bromide, acrylamide,Mixing and dispersing N, N' -methylene bisacrylamide, ammonium persulfate, polyethylene glycol methyl methacrylate, tetramethylethylenediamine and biogenic amine molecules serving as a template in a phosphate buffer solution, continuously stirring for 24-28 h at 20-25 ℃, washing with water to remove the template, separating a product, and drying to obtain Fe3O4A nano-particle biological amine remover.
8. The method of claim 7, wherein in step (3):
functionalized Fe3O4The dosage ratio of the nano particles, N-ethyl-2- (methacryloyloxy) -N, N-dimethylethylammonium bromide, acrylamide, N' -methylenebisacrylamide, ammonium persulfate, polyethylene glycol methyl methacrylate and tetramethylethylenediamine is 100 mg: (30-35) μ g: (150-165) mg: (10-11) mg: (9-10) mg: (15-17) μ L: (6-7) mu L;
functionalized Fe3O4The mass ratio of the nanoparticles to the biogenic amine molecules is (3-4) to 1.
9. A method according to any one of claims 1 to 8, wherein 1 to 10g/L Fe by volume of the fruit wine to be treated is added to the fruit wine during ageing3O4Reacting for 6-20h, and recovering the nano-particle biological amine remover by using a permanent magnet.
10. The method of claim 9, wherein the Fe is added to the fruit wine 3 to 5 days before the end of aging3O4The nano-particle biological amine remover is used for removing biological amine.
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| US20190329221A1 (en) * | 2018-07-25 | 2019-10-31 | Jiangnan University | Synthesis and application of A Nanomaterial for Removal of Patulin |
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| US20190329221A1 (en) * | 2018-07-25 | 2019-10-31 | Jiangnan University | Synthesis and application of A Nanomaterial for Removal of Patulin |
| CN111289481A (en) * | 2019-12-27 | 2020-06-16 | 中国农业科学院农业质量标准与检测技术研究所 | Biogenic amine coordination imprinted material, biogenic amine fluorescence array sensor, preparation method and application thereof |
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