CN112646081A - Preparation of novel boric acid functionalized macroporous resin and application of novel boric acid functionalized macroporous resin in selective adsorption of stevioside - Google Patents
Preparation of novel boric acid functionalized macroporous resin and application of novel boric acid functionalized macroporous resin in selective adsorption of stevioside Download PDFInfo
- Publication number
- CN112646081A CN112646081A CN202011418663.7A CN202011418663A CN112646081A CN 112646081 A CN112646081 A CN 112646081A CN 202011418663 A CN202011418663 A CN 202011418663A CN 112646081 A CN112646081 A CN 112646081A
- Authority
- CN
- China
- Prior art keywords
- resin
- macroporous resin
- stevioside
- parts
- initiator
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000011347 resin Substances 0.000 title claims abstract description 96
- 229920005989 resin Polymers 0.000 title claims abstract description 96
- 235000019202 steviosides Nutrition 0.000 title claims abstract description 69
- UEDUENGHJMELGK-HYDKPPNVSA-N Stevioside Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O UEDUENGHJMELGK-HYDKPPNVSA-N 0.000 title claims abstract description 64
- OHHNJQXIOPOJSC-UHFFFAOYSA-N stevioside Natural products CC1(CCCC2(C)C3(C)CCC4(CC3(CCC12C)CC4=C)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C(=O)OC7OC(CO)C(O)C(O)C7O OHHNJQXIOPOJSC-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 229940013618 stevioside Drugs 0.000 title claims abstract description 64
- 238000001179 sorption measurement Methods 0.000 title claims abstract description 38
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 239000004327 boric acid Substances 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000003999 initiator Substances 0.000 claims abstract description 28
- 239000000463 material Substances 0.000 claims abstract description 27
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 17
- YOCIJWAHRAJQFT-UHFFFAOYSA-N 2-bromo-2-methylpropanoyl bromide Chemical compound CC(C)(Br)C(Br)=O YOCIJWAHRAJQFT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000178 monomer Substances 0.000 claims abstract description 6
- 238000010558 suspension polymerization method Methods 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- QWMJEUJXWVZSAG-UHFFFAOYSA-N (4-ethenylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=C)C=C1 QWMJEUJXWVZSAG-UHFFFAOYSA-N 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 9
- 238000004140 cleaning Methods 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 9
- 238000010557 suspension polymerization reaction Methods 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000002952 polymeric resin Substances 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- 229920003002 synthetic resin Polymers 0.000 claims description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 5
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 5
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 5
- 239000004383 Steviol glycoside Substances 0.000 claims description 5
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 5
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 5
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 5
- 235000019411 steviol glycoside Nutrition 0.000 claims description 5
- 229930182488 steviol glycoside Natural products 0.000 claims description 5
- 150000008144 steviol glycosides Chemical class 0.000 claims description 5
- PSYGHMBJXWRQFD-UHFFFAOYSA-N 2-(2-sulfanylacetyl)oxyethyl 2-sulfanylacetate Chemical compound SCC(=O)OCCOC(=O)CS PSYGHMBJXWRQFD-UHFFFAOYSA-N 0.000 claims description 4
- 238000012986 modification Methods 0.000 claims description 4
- 230000004048 modification Effects 0.000 claims description 4
- 239000007810 chemical reaction solvent Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 238000011049 filling Methods 0.000 claims description 3
- 238000007710 freezing Methods 0.000 claims description 3
- 230000008014 freezing Effects 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000008213 purified water Substances 0.000 claims description 3
- 238000002791 soaking Methods 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 238000009736 wetting Methods 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims 3
- 238000010526 radical polymerization reaction Methods 0.000 claims 3
- 238000003786 synthesis reaction Methods 0.000 claims 3
- 238000000926 separation method Methods 0.000 abstract description 7
- 238000000746 purification Methods 0.000 abstract description 4
- 238000011084 recovery Methods 0.000 abstract description 3
- 238000005411 Van der Waals force Methods 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000001512 FEMA 4601 Substances 0.000 description 8
- HELXLJCILKEWJH-SEAGSNCFSA-N Rebaudioside A Natural products O=C(O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@]1(C)[C@@H]2[C@](C)([C@H]3[C@@]4(CC(=C)[C@@](O[C@H]5[C@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@H](O)[C@@H](CO)O5)(C4)CC3)CC2)CCC1 HELXLJCILKEWJH-SEAGSNCFSA-N 0.000 description 8
- HELXLJCILKEWJH-UHFFFAOYSA-N entered according to Sigma 01432 Natural products C1CC2C3(C)CCCC(C)(C(=O)OC4C(C(O)C(O)C(CO)O4)O)C3CCC2(C2)CC(=C)C21OC(C1OC2C(C(O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1O HELXLJCILKEWJH-UHFFFAOYSA-N 0.000 description 8
- 235000019203 rebaudioside A Nutrition 0.000 description 8
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HELXLJCILKEWJH-NCGAPWICSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- RPYRMTHVSUWHSV-CUZJHZIBSA-N rebaudioside D Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RPYRMTHVSUWHSV-CUZJHZIBSA-N 0.000 description 4
- QSRAJVGDWKFOGU-WBXIDTKBSA-N rebaudioside c Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]1(CC[C@H]2[C@@]3(C)[C@@H]([C@](CCC3)(C)C(=O)O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)CC3)C(=C)C[C@]23C1 QSRAJVGDWKFOGU-WBXIDTKBSA-N 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 3
- -1 Stevia glycosides Chemical class 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 229960004793 sucrose Drugs 0.000 description 3
- ICNCZFQYZKPYMS-UHFFFAOYSA-N 2-methylpropanoyl bromide Chemical compound CC(C)C(Br)=O ICNCZFQYZKPYMS-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CANAPGLEBDTCAF-QHSHOEHESA-N Dulcoside A Natural products C[C@@H]1O[C@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2O[C@]34CC[C@H]5[C@]6(C)CCC[C@](C)([C@H]6CC[C@@]5(CC3=C)C4)C(=O)O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H](O)[C@H]1O CANAPGLEBDTCAF-QHSHOEHESA-N 0.000 description 2
- CANAPGLEBDTCAF-NTIPNFSCSA-N Dulcoside A Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@]23C(C[C@]4(C2)[C@H]([C@@]2(C)[C@@H]([C@](CCC2)(C)C(=O)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)CC4)CC3)=C)O[C@H](CO)[C@@H](O)[C@@H]1O CANAPGLEBDTCAF-NTIPNFSCSA-N 0.000 description 2
- 239000001776 FEMA 4720 Substances 0.000 description 2
- RLLCWNUIHGPAJY-RYBZXKSASA-N Rebaudioside E Natural products O=C(O[C@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O2)[C@@H](O)[C@@H](O)[C@H](CO)O1)[C@]1(C)[C@@H]2[C@@](C)([C@@H]3[C@@]4(CC(=C)[C@@](O[C@@H]5[C@@H](O[C@@H]6[C@@H](O)[C@H](O)[C@@H](O)[C@H](CO)O6)[C@H](O)[C@@H](O)[C@H](CO)O5)(C4)CC3)CC2)CCC1 RLLCWNUIHGPAJY-RYBZXKSASA-N 0.000 description 2
- 244000228451 Stevia rebaudiana Species 0.000 description 2
- 235000006092 Stevia rebaudiana Nutrition 0.000 description 2
- OMHUCGDTACNQEX-OSHKXICASA-N Steviolbioside Natural products O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(O)=O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O OMHUCGDTACNQEX-OSHKXICASA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 235000019658 bitter taste Nutrition 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- JLPRGBMUVNVSKP-AHUXISJXSA-M chembl2368336 Chemical compound [Na+].O([C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C([O-])=O)[C@@H]1O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]1O JLPRGBMUVNVSKP-AHUXISJXSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- RLLCWNUIHGPAJY-SFUUMPFESA-N rebaudioside E Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RLLCWNUIHGPAJY-SFUUMPFESA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DRSKVOAJKLUMCL-MMUIXFKXSA-N u2n4xkx7hp Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(O)=O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DRSKVOAJKLUMCL-MMUIXFKXSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 101710141544 Allatotropin-related peptide Proteins 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 241000544066 Stevia Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
-
- 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
- B01J20/26—Synthetic macromolecular compounds
- B01J20/264—Synthetic macromolecular compounds derived from different types of monomers, e.g. linear or branched copolymers, block copolymers, graft copolymers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/256—Polyterpene radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Analytical Chemistry (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention discloses a preparation method of a stevioside selective adsorption material, and relates to the technical field of stevioside purification. The invention comprises the following steps: preparing acrylic macroporous resin by a suspension polymerization method; forming a bromo-active site on the surface of the acrylic macroporous resin by introducing an initiator BIBB to obtain an initiator functionalized resin; adding the initiator functional resin into a polymerization solution dissolved with the boric acid functional monomer, and grafting the initiator functional resin on the bromo-active site on the surface of the acrylic macroporous resin to obtain the stevioside selective adsorption material. According to the invention, through Van der Waals force and hydrogen bond acting force, the resin with good affinity and high adsorption capacity to stevioside is formed, and then boric acid site grafting is carried out on the surface of the resin by utilizing the characteristic that the specific adsorption capacity of boric acid to cis-diol is utilized, so that the enrichment, recovery and separation capacity of the resin to stevioside is effectively increased.
Description
Technical Field
The invention belongs to the technical field of stevioside purification, and particularly relates to a preparation method of a stevioside selective adsorption material.
Background
Stevioside is a mixture of several stevioside extracted from the leaves of stevia rebaudiana and is a natural sweetener, the sweetness of the stevioside is about 300 times that of cane sugar, and the stevioside has the advantages of high sweetness, low calorie, no toxicity, no side effect and the like, so the stevioside is popular among people, some artificially synthesized sweeteners are replaced in food additives, but the stevioside has bitter taste compared with the sweetness and the purity of cane sugar, the application effect is influenced to a certain extent, and the bitter taste needs to be removed.
Stevia glycosides are mixtures of eight diterpene glycosides, which are: stevioside (STV), steviolbioside (steviolbioside), Rebaudioside A (RA), Rebaudioside B (RB), Rebaudioside C (RC), Rebaudioside D (RD), Rebaudioside E (RE), dulcoside A (dulcoside A, Dul-A).
Wherein, STV and RA are main stevioside components in stevia rebaudiana Bertoni, which account for about 90 percent of the total stevioside content, and the taste of untreated stevioside is closer to that of stevioside and is far from that of cane sugar because the STV and RA account for more components. Therefore, the effective separation of STV from stevioside is an effective way to improve the mouthfeel of stevioside.
Currently, the effect of separating STV from stevioside is general, and therefore a material with higher separation efficiency is required.
Disclosure of Invention
The invention aims to provide a preparation method of a stevioside selective adsorption material, which solves the problem that the effect of separating STV from stevioside is limited in the prior art.
In order to solve the technical problems, the invention is realized by the following technical scheme:
the invention relates to a preparation method of a stevioside selective adsorption material, which comprises the following steps:
step S01: preparing hydroxyl-containing acrylate macroporous resin by a suspension polymerization method;
step S02: introducing the acrylic macroporous resin into an initiator BIBB to form brominated active sites on the surface of the acrylic macroporous resin, so as to obtain initiator functionalized resin;
step S03: adding the initiator functionalized resin into the polymerization solution, and grafting the initiator functionalized resin on the bromo-active sites on the surface of the acrylic macroporous resin to obtain the stevioside selective adsorption material.
Preferably, in step S01, the acrylic macroporous resin comprises the following components by weight: 1.072 parts of acrylates, 1.072 parts of GDMA-5.555 parts of ethyl acetate, 6.627 parts of ethyl acetate, 26.506 parts of AIBN-26.506 parts of HPMC-0.133 parts of the raw materials; wherein, the acrylate is a monomer, the EGDMA is a cross linker, the ethyl acetate is a pore-forming agent, the HPMC is a dispersant, and the AIBN is an initiator;
the preparation method of the acrylic macroporous resin comprises the following steps:
step SS 11: adding acrylate, GDMA, acetate, AIBN and HPMC into a reaction kettle in sequence, and stirring and dispersing the mixture evenly in purified water;
step SS 12: heating the reaction kettle to 65-80 ℃ to carry out suspension polymerization reaction for 9h to obtain a suspension polymerization reactant;
step SS 13: cooling the reaction kettle to normal temperature, cleaning the suspension polymerization reactant, and drying in vacuum to obtain the acrylic macroporous resin.
Preferably, in step S02, the method for forming the brominated active sites on the surface of the acrylic macroporous resin includes the following steps:
step SS 21: pre-wetting the prepared acrylic macroporous resin in methanol for 10-15min to obtain pre-wetted macroporous resin;
step SS 22: soaking the pre-wet macroporous resin in water for 2 times, removing methanol, and drying the cleaned pre-wet macroporous resin in a vacuum drying oven to obtain macroporous resin to be reacted;
step SS 23: putting the macroporous resin to be reacted into a reaction solvent, and stirring for 24 hours at normal temperature to obtain initiator functionalized resin;
step SS 24: and thoroughly cleaning the initiator functionalized resin by using pure water.
Preferably, the components of the reaction solution in the step SS23 comprise 2-bromoisobutyryl bromide, triethylamine and anhydrous tetrahydrofuran, and the weight ratio of the macroporous resin, the 2-bromoisobutyryl bromide and the triethylamine is 4.39:2.3: 1.01;
wherein the mass concentration of 2-bromoisobutyryl bromide is 10mmol/L, and the mass concentration of triethylamine is 10 mmol/L; reacting the 2-bromine isobutyryl bromide with carboxyl on the macroporous resin to be reacted to fix the bromine initiation group on the surface of the macroporous resin to be reacted.
Preferably, the pure water is second-grade RO water and pure water with the purity above.
Preferably, the polymerization solution in the step S03 includes, by weight group, 4-vinylphenylboronic acid-1.48 parts, CuCl-0.00297 parts, 2-bipyridine-0.01024 parts, and anhydrous methanol-31.64 parts; wherein, 4-vinyl phenylboronic acid is taken as a monomer, CuCl is taken as a catalyst, and 2-bipyridine and anhydrous methanol are taken as solvents;
the configuration method comprises the following steps: dissolving 4-vinylphenylboronic acid in absolute methanol, deoxidizing by circulating through a freezing pump for 3 times, and filling the vacuumized part with nitrogen after each vacuumizing; then uniformly stirring the treated anhydrous methanol solution dissolved with the 4-vinyl phenylboronic acid, CuCl and 2-bipyridyl in an oxygen-free environment to obtain a polymerization solution;
the method for grafting the bromo-active sites on the surface of the acrylic macroporous resin comprises the following steps:
step SS 31: under the room temperature and oxygen-free condition, the initiator functionalized resin is placed in the polymerization solution to react for 48 hours to obtain polymerization resin;
step SS 32: putting the obtained polymeric resin into a container filled with secondary RO water, stirring and cleaning for three times, wherein the first time is cleaned for 30 minutes at room temperature, the second time is cleaned for 60 minutes at 60 ℃, and the third time is cleaned for 30 minutes at room temperature;
step SS 33: and drying the washed polymeric resin at the temperature of 45 ℃ overnight to obtain the stevioside selective adsorption material.
The invention has the following beneficial effects:
according to the invention, through Van der Waals force and hydrogen bond acting force, the resin with good affinity and high adsorption capacity to stevioside is formed, and then boric acid site grafting is carried out on the surface of the resin by utilizing the characteristic of specific adsorption capacity of boric acid to cis-diol, so that the enrichment recovery and separation capacity of the resin to stevioside is effectively increased, high selectivity is realized on the basis of ensuring high adsorption quantity, and the separation and purification effects of stevioside are improved.
Of course, it is not necessary for any product in which the invention is practiced to achieve all of the above-described advantages at the same time.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings used in the description of the embodiments will be briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art that other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a schematic diagram of the ATRP grafting process of hydroxyl-containing acrylate resin according to the present invention;
fig. 2 is a graph of infrared absorption spectrum test performed on the steviol glycoside selective adsorbent material of the present invention.
Fig. 3 is an XPS test chart performed on the steviol glycoside selective adsorbent material of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Referring to fig. 1, the present invention is a method for preparing a selective steviol glycoside adsorption material, which includes the following steps:
step S01: preparing acrylic macroporous resin by a suspension polymerization method;
step S02: introducing the acrylic macroporous resin into an initiator BIBB to form brominated active sites on the surface of the acrylic macroporous resin, so as to obtain initiator functionalized resin;
step S03: adding the initiator functionalized resin into the polymerization solution, and grafting the initiator functionalized resin on the bromo-active sites on the surface of the acrylic macroporous resin to obtain the stevioside selective adsorption material.
Preferably, in step S01, the acrylic macroporous resin comprises the following components by weight: 1.072 parts of acrylates, 1.072 parts of GDMA-5.555 parts of ethyl acetate, 6.627 parts of ethyl acetate, 26.506 parts of AIBN-26.506 parts of HPMC-0.133 parts of the raw materials; wherein, acrylic ester is a monomer, GDMA is a cross-linking agent, ethyl acetate is a pore-forming agent, HPMC is a dispersing agent, and AIBN is an initiator;
the preparation method of the acrylic macroporous resin comprises the following steps:
step SS 11: adding acrylate, GDMA, acetate, AIBN and HPMC into a reaction kettle in sequence, and stirring and dispersing the mixture evenly in purified water;
step SS 12: heating the reaction kettle to 65-80 ℃ to carry out suspension polymerization reaction for 9h to obtain a suspension polymerization reactant;
step SS 13: cooling the reaction kettle to normal temperature, cleaning the suspension polymerization reactant, and drying in vacuum to obtain the acrylic macroporous resin.
Preferably, in step S02, the method for forming the brominated active sites on the surface of the acrylic macroporous resin comprises the following steps:
step SS 21: pre-wetting the prepared acrylic macroporous resin in methanol for 10-15min to obtain pre-wetted macroporous resin;
step SS 22: soaking the pre-wet macroporous resin in water for 2 times, removing methanol, and drying the cleaned pre-wet macroporous resin in a vacuum drying oven to obtain macroporous resin to be reacted;
step SS 23: putting the macroporous resin to be reacted into a reaction solvent, and stirring for 24 hours at normal temperature to obtain initiator functionalized resin;
step SS 24: and thoroughly cleaning the initiator functionalized resin by using pure water.
Preferably, the components of the reaction solution in step SS23 include 2-bromoisobutyryl bromide, triethylamine and anhydrous tetrahydrofuran, and the weight ratio of the macroporous resin, the 2-bromoisobutyryl bromide and the triethylamine is 4.39:2.3: 1.01;
wherein the mass concentration of 2-bromoisobutyryl bromide is 10mmol/L, and the mass concentration of triethylamine is 10 mmol/L; reacting the 2-bromine isobutyryl bromide with carboxyl on the macroporous resin to be reacted to fix the bromine initiation group on the surface of the macroporous resin to be reacted.
Preferably, the pure water is second-grade RO water and pure water of the above purity.
Preferably, the polymerization solution in step S03 includes, in terms of weight group, 4-vinylphenylboronic acid-1.48 parts, CuCl-0.00297 parts, 2-bipyridine-0.01024 parts, and anhydrous methanol-31.64 parts; wherein, 4-vinyl phenylboronic acid is taken as a monomer, CuCl is taken as a catalyst, and 2-bipyridine and anhydrous methanol are taken as solvents;
the configuration method comprises the following steps: dissolving 4-vinylphenylboronic acid in absolute methanol, deoxidizing by circulating through a freezing pump for 3 times, and filling the vacuumized part with nitrogen after each vacuumizing; then uniformly stirring the treated anhydrous methanol solution dissolved with the 4-vinyl phenylboronic acid, CuCl and 2-bipyridyl in an oxygen-free environment to obtain a polymerization solution;
the method for grafting the bromo-active sites on the surface of the acrylic macroporous resin comprises the following steps:
step SS 31: under the room temperature and oxygen-free condition, the initiator functionalized resin is placed in the polymerization solution to react for 48 hours to obtain polymerization resin;
step SS 32: putting the obtained polymeric resin into a container filled with secondary RO water, stirring and cleaning for three times, wherein the first time is cleaned for 30 minutes at room temperature, the second time is cleaned for 60 minutes at 60 ℃, and the third time is cleaned for 30 minutes at room temperature;
step SS 33: and drying the washed polymeric resin at the temperature of 45 ℃ overnight to obtain the stevioside selective adsorption material.
The first embodiment is as follows:
the embodiment provides application of the stevioside selective adsorption material in adsorption of stevioside.
Weighing 0.1g of stevioside selective adsorption material, placing the stevioside selective adsorption material into an erlenmeyer flask, then transferring 50ml of prepared stevioside solution (STV: RA ═ 1:1) with the concentration of 6g/L, adding the stevioside solution into the erlenmeyer flask, sealing the erlenmeyer flask, placing the erlenmeyer flask into a constant-temperature oscillation box, oscillating at the constant temperature of 30 ℃, and calculating the equilibrium adsorption quantity Qe of stevioside according to the following formula:
wherein Qe is the equilibrium adsorption capacity of the selective adsorption material to stevioside, and the unit is mg/g; v is the volume of the stevioside solution in mL; c0Is the initial concentration of the stevioside solution in g/L; ct is the concentration of stevioside in the supernatant after adsorption equilibrium, and the unit is g/L; and m is the mass of the composite adsorbing material PMAA/PAS and the unit is g.
The selectivity a for STV versus RA in steviol glycosides was calculated by the formula:
wherein a is the selectivity of the resin to STV, QSTV，QRAAdsorption amounts of STV and RA, respectivelyIn units of mg/g, C in solutionSTV,CRAThe concentrations of STV and RA in the adsorbed solution are respectively in mg/ml.
In the application, the optimal adsorption temperature is 30 ℃, the adsorption pH is 9, the maximum adsorption capacity is 75.23mg/g, the highest selectivity is 10.42, and the boric acid functionalized resin has stronger selective adsorption capacity on stevioside.
Example two:
as shown in FIG. 2, the IR spectra of the original hydroxyl-containing acrylic resin and the grafted resin microspheres obtained in this example show that 1350cm in the spectrum of the boric acid functionalized grafted resin-1A new B-O bond characteristic absorption peak appears, which proves that VPBA is successfully grafted to the surface of the acrylate resin;
as shown in figure 3, XPS test is carried out on grafted acrylate resins with different particle sizes, and the test result shows that the highest grafting amount of boron can reach 6.36%, so that the stevioside selective adsorption material prepared by the method provided by the invention is helpful for improving the enrichment, recovery and separation capacity of stevioside, has higher selectivity on the basis of ensuring higher adsorption amount, and has better effect in the separation and purification of stevioside.
In the description herein, references to the description of "one embodiment," "an example," "a specific example" or the like are intended to mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The preferred embodiments of the invention disclosed above are intended to be illustrative only. The preferred embodiments are not intended to be exhaustive or to limit the invention to the precise embodiments disclosed. Obviously, many modifications and variations are possible in light of the above teaching. The embodiments were chosen and described in order to best explain the principles of the invention and the practical application, to thereby enable others skilled in the art to best utilize the invention. The invention is limited only by the claims and their full scope and equivalents.
Claims (6)
1. A preparation method of a stevioside selective adsorption material is characterized in that boric acid functionalized grafting modification is directly carried out by an atomic radical polymerization (ATRP) method on the basis of hydroxyl resin synthesis, and comprises the following steps:
step S01: preparing hydroxyl-containing acrylate macroporous resin by a suspension polymerization method;
step S02: introducing the acrylic macroporous resin into an initiator BIBB to form brominated active sites on the surface of the acrylic macroporous resin, so as to obtain initiator functionalized resin;
step S03: adding the initiator functional resin into a polymerization solution dissolved with the boric acid functional monomer, and grafting the initiator functional resin on the bromo-active site on the surface of the acrylic macroporous resin to obtain the stevioside selective adsorption material.
2. The method for preparing a steviol glycoside selective adsorption material according to claim 1, wherein in the step S01, the components of the acrylic macroporous resin comprise, by weight: 1.072 parts of acrylate, 1.072 parts of EGDMA-5.555 parts of acetate, 6.627 parts of acetate, 26.506 parts of AIBN-26.506 parts of HPMC-0.133 part of the mixture;
the preparation method of the acrylic macroporous resin comprises the following steps:
step SS 11: adding acrylate, GDMA, acetate, AIBN and HPMC into a reaction kettle in sequence, and stirring and dispersing the mixture evenly in purified water;
step SS 12: heating the reaction kettle to 65-80 ℃ to carry out suspension polymerization reaction for 9h to obtain a suspension polymerization reactant;
step SS 13: cooling the reaction kettle to normal temperature, cleaning the suspension polymerization reactant, and drying in vacuum to obtain the acrylic macroporous resin.
3. The method for preparing the stevioside selective adsorption material according to claim 1, wherein the boric acid functionalized grafting modification is directly performed by an atomic radical polymerization (ATRP) method on the basis of hydroxyl resin synthesis, and the method for forming the brominated active sites on the surface of the acrylate macroporous resin in the step S02 comprises the following steps:
step SS 21: pre-wetting the prepared acrylic macroporous resin in methanol for 10-15min to obtain pre-wetted macroporous resin;
step SS 22: soaking the pre-wet macroporous resin in water for 2 times, removing methanol, and drying the cleaned pre-wet macroporous resin in a vacuum drying oven to obtain macroporous resin to be reacted;
step SS 23: putting the macroporous resin to be reacted into a reaction solvent containing an initiator, and stirring for 24 hours at normal temperature to obtain initiator functionalized resin;
step SS 24: and thoroughly cleaning the initiator functionalized resin by using pure water.
4. The preparation method of the stevioside selective adsorption material according to claim 3, wherein the boric acid functionalized grafting modification is directly carried out by an atomic radical polymerization (ATRP) method on the basis of hydroxyl resin synthesis, the components of the reaction solution in the step SS23 comprise 2-bromoisobutyryl bromide, triethylamine and anhydrous tetrahydrofuran, and the weight ratio of the hydroxyl-containing macroporous resin, the 2-bromoisobutyryl bromide and the triethylamine is 4.39:2.3: 1.01.
5. The method according to claim 3, wherein the pure water is second-stage RO water or pure water having a purity higher than that of the second-stage RO water.
6. The method of claim 1, wherein the polymerization solution in step S03 comprises, by weight, 1.48 parts of 4-vinylphenylboronic acid, 1.48 parts of CuCl-0.00297 parts of 2-bipyridine-0.01024 parts of anhydrous methanol-31.64 parts of the polymerization solution;
the configuration method comprises the following steps: dissolving 4-vinylphenylboronic acid in absolute methanol, deoxidizing by circulating through a freezing pump for 3 times, and filling the vacuumized part with nitrogen after each vacuumizing; then uniformly stirring the treated anhydrous methanol solution dissolved with the 4-vinyl phenylboronic acid, CuCl and 2-bipyridyl in an oxygen-free environment to obtain a polymerization solution;
the method for grafting the bromo-active sites on the surface of the acrylic macroporous resin comprises the following steps:
step SS 31: under the room temperature and oxygen-free condition, the initiator functionalized resin is placed in the polymerization solution to react for 48 hours to obtain polymerization resin;
step SS 32: putting the obtained polymeric resin into a container filled with secondary RO water, stirring and cleaning for three times, wherein the first time is cleaned for 30 minutes at room temperature, the second time is cleaned for 60 minutes at 60 ℃, and the third time is cleaned for 30 minutes at room temperature;
step SS 33: and drying the washed polymeric resin at the temperature of 45 ℃ overnight to obtain the stevioside selective adsorption material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011418663.7A CN112646081A (en) | 2020-12-07 | 2020-12-07 | Preparation of novel boric acid functionalized macroporous resin and application of novel boric acid functionalized macroporous resin in selective adsorption of stevioside |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011418663.7A CN112646081A (en) | 2020-12-07 | 2020-12-07 | Preparation of novel boric acid functionalized macroporous resin and application of novel boric acid functionalized macroporous resin in selective adsorption of stevioside |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112646081A true CN112646081A (en) | 2021-04-13 |
Family
ID=75350336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011418663.7A Pending CN112646081A (en) | 2020-12-07 | 2020-12-07 | Preparation of novel boric acid functionalized macroporous resin and application of novel boric acid functionalized macroporous resin in selective adsorption of stevioside |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112646081A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114031694A (en) * | 2021-12-23 | 2022-02-11 | 云南三七科技有限公司 | Extraction method of pseudo-ginseng polysaccharide |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080234208A1 (en) * | 2005-07-14 | 2008-09-25 | National Institute Of Pharmaceutical R&D Co., Ltd | Medical Composition Containing Ginseng Secondary Glycosides, Its Preparation Method and Application |
| CN102060891A (en) * | 2009-11-13 | 2011-05-18 | 中国科学院兰州化学物理研究所 | Technological process for preparing stevioside from stevia rebaudiana bertoni |
| KR101277476B1 (en) * | 2012-09-10 | 2013-06-21 | 오양우 | Preparation of moleculary imprinting polymer porous particles |
| CN103319550A (en) * | 2013-07-12 | 2013-09-25 | 兰州理工大学 | Method for separating and purifying stevioside in crude stevia rebaudiana |
| CN103755567A (en) * | 2014-01-06 | 2014-04-30 | 巨化集团技术中心 | Preparation method of acrylic acid serial perfluoroeneoxy ester |
| JP2014114289A (en) * | 2013-12-13 | 2014-06-26 | Showa Denko Kk | Cosmetic and skin external preparation |
| CN105924558A (en) * | 2016-06-28 | 2016-09-07 | 中南大学 | Preparation method and application of hypercrosslinked resin with controllable polarity and pore structure |
| CN108929408A (en) * | 2018-07-20 | 2018-12-04 | 中北大学 | A kind of preparation method and application of stevioside imprinted material |
| CN108976361A (en) * | 2018-05-04 | 2018-12-11 | 江苏大学 | A kind of preparation method and application of the affine imprinted polymer of the hollow boron of single hole |
| CN109550373A (en) * | 2019-01-29 | 2019-04-02 | 艾易西(中国)环保科技有限公司 | One kind is except base material and preparation method thereof |
-
2020
- 2020-12-07 CN CN202011418663.7A patent/CN112646081A/en active Pending
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080234208A1 (en) * | 2005-07-14 | 2008-09-25 | National Institute Of Pharmaceutical R&D Co., Ltd | Medical Composition Containing Ginseng Secondary Glycosides, Its Preparation Method and Application |
| CN102060891A (en) * | 2009-11-13 | 2011-05-18 | 中国科学院兰州化学物理研究所 | Technological process for preparing stevioside from stevia rebaudiana bertoni |
| KR101277476B1 (en) * | 2012-09-10 | 2013-06-21 | 오양우 | Preparation of moleculary imprinting polymer porous particles |
| CN103319550A (en) * | 2013-07-12 | 2013-09-25 | 兰州理工大学 | Method for separating and purifying stevioside in crude stevia rebaudiana |
| JP2014114289A (en) * | 2013-12-13 | 2014-06-26 | Showa Denko Kk | Cosmetic and skin external preparation |
| CN103755567A (en) * | 2014-01-06 | 2014-04-30 | 巨化集团技术中心 | Preparation method of acrylic acid serial perfluoroeneoxy ester |
| CN105924558A (en) * | 2016-06-28 | 2016-09-07 | 中南大学 | Preparation method and application of hypercrosslinked resin with controllable polarity and pore structure |
| CN108976361A (en) * | 2018-05-04 | 2018-12-11 | 江苏大学 | A kind of preparation method and application of the affine imprinted polymer of the hollow boron of single hole |
| CN108929408A (en) * | 2018-07-20 | 2018-12-04 | 中北大学 | A kind of preparation method and application of stevioside imprinted material |
| CN109550373A (en) * | 2019-01-29 | 2019-04-02 | 艾易西(中国)环保科技有限公司 | One kind is except base material and preparation method thereof |
Non-Patent Citations (7)
| Title |
|---|
| FAYIN YE 等: "Adsorption characteristics of stevioside and rebaudioside A from aqueous solutions on 3-aminophenylboronic acid-modified poly(divinylbenzene-co-acrylic acid)", 《SEPARATION AND PURIFICATION TECHNOLOGY》, vol. 118, 30 October 2013 (2013-10-30), pages 1 * |
| 孔令义: "《中药制药化学》", 30 April 2007, 中国医药科技出版社, pages: 34 * |
| 樊花: "功能化磁性微球对顺式二羟基物质的分离富集性能", 《中国博士学位论文全文数据库工程科技Ⅰ辑》 * |
| 樊花: "功能化磁性微球对顺式二羟基物质的分离富集性能", 《中国博士学位论文全文数据库工程科技Ⅰ辑》, no. 6, 15 June 2017 (2017-06-15), pages 87 - 90 * |
| 缪勇 等: "《中草药植物提取与深加工新技术实用手册 第2卷》", 天津电子出版社, pages: 666 * |
| 顾觉奋 等: "《离子交换与吸附树脂在制药工业上的应用》", 30 April 2008, 中国医药科技出版社, pages: 209 * |
| 齐慧敏: "甲基丙烯酸羟乙酯系列多孔材料的合成、改性及其应用研究", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》, no. 8, pages 016 - 170 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114031694A (en) * | 2021-12-23 | 2022-02-11 | 云南三七科技有限公司 | Extraction method of pseudo-ginseng polysaccharide |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112646081A (en) | Preparation of novel boric acid functionalized macroporous resin and application of novel boric acid functionalized macroporous resin in selective adsorption of stevioside | |
| JPS59159791A (en) | Decomposition of arabinose by selective adsorption to zeolite molecular sieve | |
| CN112341579B (en) | Adsorption resin for stevioside separation and purification and application thereof | |
| PL196962B1 (en) | Chromatographic fractionation of vegetable material | |
| Shi et al. | Synthesis of bifunctional polymeric adsorbent and its application in purification of Stevia glycosides | |
| CN112500538B (en) | Molecularly imprinted material for separating and purifying stevioside RA and application thereof | |
| CN111318184A (en) | Click chemical grafting functionalized polyimide CO2Method for producing separation membrane | |
| CN111704693B (en) | Pseudo template molecularly imprinted polymer and application thereof | |
| CN108467415B (en) | Purification method of industrial stevioside crystallization mother liquor | |
| Xu et al. | Preparation of modified cotton cellulose in ionic liquid and its adsorption of Cu (II) and Ni (II) from aqueous solutions | |
| CN115228426A (en) | Modified silicon dioxide adsorbent for trapping medium-low concentration carbon dioxide | |
| CN106967218B (en) | Amino-terminated hyperbranched polyamide oxidation modified peanut shell and application thereof in separation and detection of sunset yellow in food | |
| JPS5852999B2 (en) | Stevioside Noseiseihou | |
| CN113797899B (en) | Preparation method of P (Allyl-beta-CD)/PSA microspheres and application of P (Allyl-beta-CD)/PSA microspheres in adsorption of cinchonine | |
| CN113214531B (en) | Hydrophobic/hydrophilic interpenetrating network resin and preparation and application thereof | |
| US4937295A (en) | Boron resins of high selective absorbent power | |
| CN112500440B (en) | Method for extracting rebaudioside-A from stevia rebaudiana | |
| CN108752400B (en) | Preparation method of naringin dihydrochalcone | |
| CN112300231A (en) | Method for extracting high-purity stevioside | |
| JP3883236B2 (en) | Separation method of sesaminol triglucoside | |
| CN111589429A (en) | Phenanthroline polymer and preparation method and application thereof | |
| Sreenivasan | Solvent effect on the interaction of steroids with a novel methyl β‐cyclodextrin polymer | |
| CN107129581B (en) | Amino-terminated hyperbranched polyamide chlorinated modified peanut shell and application thereof in separation and detection of sunset yellow in food | |
| CN116199563B (en) | Synthesis method for idecalcitol 20S isomer | |
| KR101933957B1 (en) | Method for crystallization and purification of tagatose by using hydrophilic solvent from mixture of fructose-tagatose |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20210413 |
|
| RJ01 | Rejection of invention patent application after publication |