CN106179239A - The preparation method and applications of pomelo peel modified amido functionalization adsorbent - Google Patents
The preparation method and applications of pomelo peel modified amido functionalization adsorbent Download PDFInfo
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- CN106179239A CN106179239A CN201610550185.2A CN201610550185A CN106179239A CN 106179239 A CN106179239 A CN 106179239A CN 201610550185 A CN201610550185 A CN 201610550185A CN 106179239 A CN106179239 A CN 106179239A
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- pomelo peel
- adsorbent
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- modified amido
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- 239000003463 adsorbent Substances 0.000 title claims abstract description 67
- 238000007306 functionalization reaction Methods 0.000 title claims abstract description 43
- 125000003368 amide group Chemical group 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 240000000560 Citrus x paradisi Species 0.000 title claims abstract 24
- 238000001179 sorption measurement Methods 0.000 claims abstract description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000003344 environmental pollutant Substances 0.000 claims abstract description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 26
- 231100000719 pollutant Toxicity 0.000 claims abstract description 23
- 239000000463 material Substances 0.000 claims abstract description 17
- 229910001385 heavy metal Inorganic materials 0.000 claims abstract description 16
- 239000000843 powder Substances 0.000 claims abstract description 14
- 239000011651 chromium Substances 0.000 claims abstract description 11
- 239000010949 copper Substances 0.000 claims abstract description 10
- 230000004048 modification Effects 0.000 claims abstract description 10
- 238000012986 modification Methods 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 8
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 7
- 229910052802 copper Inorganic materials 0.000 claims abstract description 7
- 238000007142 ring opening reaction Methods 0.000 claims abstract description 4
- 244000276331 Citrus maxima Species 0.000 claims description 67
- 238000010521 absorption reaction Methods 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 9
- 239000002351 wastewater Substances 0.000 claims description 8
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000004040 coloring Methods 0.000 claims description 4
- 238000006735 epoxidation reaction Methods 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- 238000007605 air drying Methods 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
- 238000003795 desorption Methods 0.000 claims description 2
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 claims description 2
- 230000010355 oscillation Effects 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 1
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 abstract description 11
- 229960000907 methylthioninium chloride Drugs 0.000 abstract description 11
- 239000001045 blue dye Substances 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 5
- 125000000524 functional group Chemical group 0.000 abstract description 5
- -1 amino, hydroxyl Chemical group 0.000 abstract description 4
- 150000001450 anions Chemical class 0.000 abstract description 2
- 150000001768 cations Chemical class 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 238000007873 sieving Methods 0.000 abstract description 2
- 238000010298 pulverizing process Methods 0.000 abstract 1
- 235000001759 Citrus maxima Nutrition 0.000 description 10
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 8
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 8
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 239000001913 cellulose Substances 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000356 contaminant Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 4
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- 229960002216 methylparaben Drugs 0.000 description 4
- 238000011017 operating method Methods 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 4
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 4
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 229920002488 Hemicellulose Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 229960001617 ethyl hydroxybenzoate Drugs 0.000 description 3
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 3
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 3
- 230000036541 health Effects 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229960003742 phenol Drugs 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000001814 pectin Substances 0.000 description 2
- 229920001277 pectin Polymers 0.000 description 2
- 235000010987 pectin Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- YWNYZQTZOONLGU-UHFFFAOYSA-N C(CC)Cl.[O] Chemical compound C(CC)Cl.[O] YWNYZQTZOONLGU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- WGKMWBIFNQLOKM-UHFFFAOYSA-N [O].[Cl] Chemical compound [O].[Cl] WGKMWBIFNQLOKM-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 238000009303 advanced oxidation process reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000000701 coagulant Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000013325 dietary fiber Nutrition 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 244000144992 flock Species 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 230000003188 neurobehavioral effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 231100001239 persistent pollutant Toxicity 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 238000007146 photocatalysis Methods 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229920001221 xylan Polymers 0.000 description 1
- 150000004823 xylans Chemical group 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
- B01J20/24—Naturally occurring macromolecular compounds, e.g. humic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/286—Treatment of water, waste water, or sewage by sorption using natural organic sorbents or derivatives thereof
-
- 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
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
- B01J2220/48—Sorbents characterised by the starting material used for their preparation
- B01J2220/4812—Sorbents characterised by the starting material used for their preparation the starting material being of organic character
- B01J2220/4825—Polysaccharides or cellulose materials, e.g. starch, chitin, sawdust, wood, straw, cotton
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/10—Inorganic compounds
- C02F2101/20—Heavy metals or heavy metal compounds
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/10—Inorganic compounds
- C02F2101/20—Heavy metals or heavy metal compounds
- C02F2101/22—Chromium or chromium compounds, e.g. chromates
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
- C02F2101/308—Dyes; Colorants; Fluorescent agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Water Treatment By Sorption (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The present invention discloses the preparation method and applications of a kind of pomelo peel modified amido functionalization adsorbent.Preparation process is: with pomelo peel as raw material, cleaned, carry out after drying pulverizing, sieving, obtaining the pomelo peel powder of pretreatment, one kettle way is substituted, ring-opening reaction carries out surface-functionalized modification to material in employing, finally gives the pomelo peel adsorbing material that amino functional is modified；The product that the present invention obtains is powder, and sundown has compact structure of fibrous tissue, and inside exists substantial amounts of hole；Rich in functional groups such as amino, hydroxyl and carbonyls, parabens emerging pollutant, the heavy metal copper that exceeds standard, chromium and methylene blue dye etc. in water there is excellent adsorption effect.It is simple that the present invention has preparation method, with low cost, resulting materials is cheap and easy to get, good biocompatibility, environmental friendliness, containing the chelating group of a large amount of functionalization, it is possible to achieve anion, cation adsorb simultaneously with remove and there is advantages such as can being recycled for multiple times.
Description
Technical field
The present invention relates to a kind of methods and applications technology utilizing useless pomelo peel to prepare amino functional adsorbent, be specially
The preparation method of pomelo peel modified amido functionalization adsorbent, and utilize pomelo peel amino functional absorption prepared by the present invention
Exceed standard in water novel environmental pollutant, the heavy metal copper that exceeds standard, chromium and methylene blue dye pigment etc. are removed in agent, reach innoxious place
Manage and realize the purposes such as fwaater resources protection.
Background technology
Emerging pollutant (emerging contaminants, ECs) refer to " new identification or the most unconfirmed ", " not by method
Rule specification " and the chemical pollutant of " health and ecological environment are had potential or essence threat ".The kind of emerging pollutant
Class mainly includes Pharmaceuticals and personal care products, incretion interferent, persistent pollutant, perfluorochemical, drinking water disinfection
By-product and other industrial chemical matter etc..Though the existence concentration that emerging pollutant are in the environment is low (generally at μ g/L to ng/L
Between), but can persistently be present in environment, accumulated by Food chain and human health is caused adverse effect, there is height
Poison, persistently, biological accumulation, the characteristic such as Long-distance Migrating.By biological accumulation effect, pass to be positioned at the people on biological chain top
During class, the toxicity of these materials can be amplified to 70,000 times, enter people know from experience cause that neurobehavioral is not normal, endocrine regulation, reproduction
The increase etc. of system and immune system destruction, abnormal development and tumor.But, in the design of tradition water treatment technology usually not
In view of the removal of emerging pollutant, research energy is efficient, high selectivity material, and is applied to remove emerging pollutant in water
(ECs) have great importance.
The pigment such as heavy metal and dyestuff that exceeds standard is widely present in water environment, and has latent to water environment and human health
In impact, also result in the extensive concern of people in recent years.Currently for emerging pollutant and exceed standard heavy metal and dyestuff isochrome
The removal technique of element mainly has: coagulant sedimentation, active carbon adsorption, membrane process, advanced oxidation processes (ozone oxidation, chlorine oxygen
Change, photocatalysis) etc..But removal efficiency is the highest, and advanced oxidation, nanofiltration/reverse osmosis even depth process process energy consumption and cost
The most of a relatively high.There is challenge in the research about their minimizing technology the most always.
Biological adsorption agent, compared with traditional adsorbent, has a following principal character: (1) wide adaptability, can be at multiple pH
Operate under value, temperature and the course of processing；(2) metal selective is high, can from solution Adsorption of Heavy Metal Ions and not by alkali metal
The interference of ion；(3) concentration of metal ions impact is little, at low dense (< 10mg L-1) and high concentration (> 100mg L-1All have under)
There is good metal adsorption ability；(4) good to Organic substance tolerance, Organic Pollution (≤5000mg L-1) do not affect metal from
The absorption of son；(5) regeneration capacity is strong, step is simple, and after regeneration, absorbability is without substantially reducing.But utilize former slag to carry out absorption to deposit
Relatively low at absorbability, the problems such as chemical oxygen consumption (COC) increase are caused in water owing to soluble organic matter dissolves.Therefore, have
Necessity carries out chemical modification to improve adsorption capacity and chemical stability to it.
Fructus Citri grandis is one of China's main fruit, a large amount of plantation in many areas in south.Pomelo peel account for full weight 55%～
54%.Generally pomelo peel is not utilized just abandons, and causes significant wastage.Owing to the white flock layer inside pomelo peel containing
Substantial amounts of cellulose, family is commonly used to deodorant for refregerator.Pomelo peel contains a large amount of cellulose, hemicellulose, lignin and pectin, institute
Can be used in theory prepare adsorbent, in order to remove the pollutant of environment.But by its direct applied adsorption efficiency also
The highest.Such as pomelo peel is 169.5mg/g to dye adsorption amounts such as methylene blues.If useless pomelo peel can be carried out functional group to repair
Decorations, it is possible to become the adsorbent with good adsorption properties, undoubtedly in resource regeneration and recycling, turn waste into wealth
Etc. aspect there is important and positive meaning.
At present, although people have done certain research to from the modified technique of pomelo peel, but dietary fiber is focused primarily upon
Thick extraction, how it is chemically modified and less for the research of environmental contaminants adsorbent." changing of the report such as Xu Zheng
Property fruit peel to Cr VI Study on adsorption properties in water " (scientific and technological information, 2013,5,66-68) with 1% TGA soak also
Pomelo peel, and Cr VI absorption in the water are modified in stirring, and adsorption efficiency there are no is obviously improved.Huang Donglan, " the Fructus Citri grandis of report
Sub-skin saponification is cross-linking modified and to Cu in aqueous solution2+Study on adsorption properties " (food industry technology, 2015,36 (10),
225-228) use ethanol, NaOH and MgCl2During pomelo peel is processed, the most not unmodified and its activity modified
Group, therefore absorption property and the selectivity of target contaminant are not improved significantly by resulting materials；And reaction time is relatively
Long, complex operation, functional group's ratio is wayward, and therefore, its application is by bigger restriction.
Summary of the invention
The present invention is directed to the above-mentioned deficiency of prior art, it is provided that a kind of simple to operate, efficiency is high, toxicity is low and more environmentally-friendly
The preparation method of pomelo peel modified amido functionalization adsorbent.
In order to solve above-mentioned technical problem, the technical solution used in the present invention is: a kind of pomelo peel modified amido functionalization
The preparation method of adsorbent, with useless pomelo peel as raw material, through over cleaning, is dried, pulverizes, sieves, and then uses one kettle way through taking
Generation, ring-opening reaction carry out surface-functionalized modification to material, finally give pomelo peel modified amido functionalization adsorbent (amino merit
The pomelo peel adsorbing material that energyization is modified).
A kind of preparation method of the pomelo peel modified amido functionalization adsorbent of the present invention, concrete preparation process includes:
(1) pomelo peel is carried out roguing, pulverizes after drying, sieve, obtain the pomelo peel powder of pretreatment；
(2) weigh the pomelo peel powder of step (1) gained, distribute it to the epoxychloropropane that volume ratio is 0.5～4:1
With (V in the mixed solution of organic solventEpoxychloropropane: VOrganic solvent=0.5～4:1)；The pomelo peel powder of step (1) gained and epoxy
The solid-to-liquid ratio of chloropropane is the 20～500g:100mL (shaddock peel powder of the epoxychloropropane corresponding 20～500g of i.e. every 100ml
End)；Then 0.5-10h is reacted at 50-100 DEG C under stirring, it is achieved hydroxyl (hydroxyl on its surface herein, the tool to its surface
Body is the surface hydroxyl of the chemical composition in pomelo peel powder) carry out epoxidation modification；
(3) in the reaction system of step (2) epoxidation modification, organic polyamine is added so that organic multicomponent amine is whole
The volume fraction of reaction system solution is 10-50%；Then proceeding at 50-100 DEG C of stirring reaction 0.5-10h, sucking filtration, under room temperature
Distillation washing is washed to pH=7；By gained solid 40-100 DEG C of drying, obtain amino functional adsorbent.
In step of the present invention (1), being dried of pomelo peel can use natural air drying or 50-100 DEG C of drying in an oven
2～24 hours；The sieve used that sieves is 40-150 mesh sieve.
Organic solvent used in step of the present invention (2) is in ethanol, propylene glycol, glycerol, N,N-dimethylformamide
One.
Epoxychloropropane and organic solvent volume ratio preferably 1～2:1 in step of the present invention (2)；Pomelo peel powder and ring
The solid-to-liquid ratio of oxygen chloropropane is preferably 50～200g:100mL.
Organic multicomponent amine used in step of the present invention (3) is in ethylenediamine, Diethylenetriamine, three second tetramines, tetren
A kind of；Organic multicomponent amine is preferably 15-25% in the volume fraction of whole solution；Reaction temperature is preferably 60～90 DEG C, reaction
Time is preferably 1～4h, and stir speed (S.S.) is 150～300 revs/min, and (above-mentioned reaction temperature, time and stir speed (S.S.) are equally applicable to
Step (2))；Preferred 40-80 DEG C of drying baker baking temperature.
The application in absorption pollutant of the pomelo peel modified amido functionalization adsorbent of the present invention, concrete may be used for
Parabens emerging pollutant, the heavy metal copper that exceeds standard, chromium and the absorption of coloring matter and removal in water.
Preferred according to the present invention, the application of described sub-skin modified amido functionalization adsorbent, for p-Hydroxybenzoate
The absorption of the pigments such as class emerging pollutant, the heavy metal copper that exceeds standard, chromium and methylene blue dye and removal.Method is as follows: in room temperature
Under oscillating condition, putting into the amino functional modification pomelo peel adsorbing material of the present invention, dosage is adsorbent in every liter of waste water
Content is 0.5～5g, and oscillation rate is 100～300 revs/min, and the time is 30～180 minutes；Parabens in water
Emerging pollutant can be more than 99% with the clearance of coloring matter.
Pomelo peel modified amido functionalization adsorbent of the present invention remove the pH condition of p-Hydroxybenzoate in water be 1.0～
12.0, preferably pH are 6.0～8.0；The pH condition of heavy metal copper (II) of exceeding standard in water is 1.0～6.0, preferably pH be 3.0～
4.0；The pH condition of chromium (VI) is 1.0～12.0, and preferably pH is 2.0～4.0；The pH condition of methylene blue dye pigment is 1.0
～12.0, preferably pH is 8.0～10.0.After the most above-mentioned pH is input pomelo peel modified amido functionalization adsorbent of the present invention
The pH of waste water.
Pomelo peel modified amido functionalization adsorbent of the present invention can remove the dirt of water cationic and anionic simultaneously
Dye thing.When pH is 3.0～4.0, to the going of chromium (VI) solution containing copper (II) that concentration is 100mg/L and 200mg/L simultaneously
Except rate is up to 99%.
Pomelo peel modified amido functionalization adsorbent of the present invention can regenerate, and adsorbent acid or alkali after using take off
Attached, after 5 times recycle adsorption efficiency remain to keep about 90% or more than.
Advantages of the present invention and beneficial effect:
1. the present invention is with pomelo peel as raw material, by cleaning, be dried, pulverize, sieving, is substituted further, ring-opening reaction
Material is carried out surface-functionalized modification, finally gives the pomelo peel adsorbing material that amino functional is modified.；The inventive method obtains
The product obtained is powder, and sundown has compact structure of fibrous tissue, and inside exists substantial amounts of hole (see accompanying drawing 2 institute
Show)；Rich in functional group'ss (shown in accompanying drawing 3) such as amino, hydroxyl and carbonyls；This raw material is easy to get, good biocompatibility, environment friend
Well, can realize turning waste into wealth, and containing the chelating group of a large amount of amino functionals, it is possible to achieve novel environmental pollutant, color
Element and anion, cation heavy metal contaminants adsorb simultaneously and remove, and have advantages such as can being recycled for multiple times.
2. the pomelo peel modified amido functionalization adsorbent of the present invention, is experimentally confirmed: this invention operating procedure is simple,
Pomelo peel modified amido functionalization adsorbent even particle size distribution with low cost, that obtain, stable in properties；To para hydroxybenzene in water
Formate ester novel environmental pollutant, heavy metal and methylene blue pigment etc. have high adsorption capacity, are effectively to remove waste water
The potential adsorbent of middle harmful substance.Amino functional modification pomelo peel adsorbing material of the present invention can regenerate, after using
Adsorbent acid or alkali desorption, after 5 times recycle, adsorption efficiency remains to keep about 90%.
Accompanying drawing explanation
Fig. 1 is that the pomelo peel that utilizes of the present invention prepares the schematic flow sheet of amino functional adsorbent.
Fig. 2 is according to embodiments of the present invention, the scanning electron microscope (SEM) of the pomelo peel modified amido functionalization adsorbent obtained
Photo.
Fig. 3 is according to embodiments of the present invention, the infrared spectrogram of the pomelo peel modified amido functionalization adsorbent obtained.
Fig. 4 is that the pomelo peel modified amido functionalization adsorbent prepared of the embodiment of the present invention is in water 4 kinds of para hydroxybenzene first
The adsorption isothermal curve of acid esters.
Fig. 5 be pomelo peel modified amido functionalization adsorbent prepared by the embodiment of the present invention be Cu to heavy metal ion in water
(II) adsorption isothermal curve.
Fig. 6 be pomelo peel modified amido functionalization adsorbent prepared by the embodiment of the present invention be Cr to heavy metal ion in water
(VI) adsorption isothermal curve；
Fig. 7 is that the pomelo peel modified amido functionalization adsorbent prepared of the embodiment of the present invention is to water Methylene Blue dyestuff
Adsorption isothermal curve.
Fig. 8 is that different pH value amino functional shaddock peel adsorbent is adsorbed containing the copper (II) that concentration is 100mg/L simultaneously
Adsorption rate curve with the waste water of the chromium (VI) of 200mg/L；
Fig. 9 is that the pomelo peel modified amido functionalization adsorbent prepared of the embodiment of the present invention is in water 4 kinds of para hydroxybenzene first
The sorption cycle of acid esters uses figure.
Detailed description of the invention
Below in conjunction with the accompanying drawings and present disclosure is described further by specific embodiment, the purpose of the present invention and effect are made
Fruit becomes apparent from, but the present invention is not limited solely to following example.Preparation technology flow chart of the present invention is as it is shown in figure 1, concrete
Step is with reference to each embodiment.
Embodiment 1
(1) pulverize after useless pomelo peel being carried out roguing, natural air drying, cross 100 mesh sieves, obtain the Fructus Citri grandis of pretreatment
Sub-corium farinosum end；
(2) weighing 10g step (1) gained pretreated pomelo peel powder, distributing it to 20mL volume ratio is 1.2:1
Epoxychloropropane and ethanol mixed solution in, stir under 250 revs/min, react 1h at 75 DEG C, the hydroxyl on its surface is carried out
Epoxidation modification；Adding 4mL ethylenediamine further, continue to react 2h, sucking filtration at 75 DEG C, under room temperature, distillation washing is repeatedly to pH=
7；Gained solid is placed in drying baker 60 DEG C of drying, obtains amino functional adsorbent.
The operating procedure of embodiment 2～6 is shown in Table 1 institute with embodiment 1, raw material, composition of raw materials and preparation condition parameter
Show.
Table 1 embodiment of the present invention 1～6 raw material components and preparation parameter
Pomelo peel modified amido functionalization sample of sorbent prepared by the embodiment of the present invention by scanning electron microscope (SEM),
It is characterized by the means such as infrared spectrum (FTIR), and is applied to p-Hydroxybenzoate in water, heavy metal and methylene blue
Deng absorption and removal.
Fig. 2 and Fig. 3 is the scanning of the pomelo peel modified amido functionalization adsorbent that 1 obtains according to embodiments of the present invention respectively
Electromicroscopic photograph and infrared spectrum；
As shown in Figure 2, the amino functional adsorbent utilizing pomelo peel waste material to prepare gained has compact fibrous tissue
Structure, there is substantial amounts of hole in inside；From the infrared spectrum of Fig. 3 sample it can be seen that amino functional adsorbent～
3418cm-1Wide and strong adsorption peak occurs ,-the OH ,-COOH and-NH of material surface can be attributed to2Absworption peak；～2929cm-1
For saturated C-H stretching vibration adsorption peak ,～1734cm-1Place is C=O stretching vibration, illustrates that pomelo peel contains carbonyl, because Fructus Citri grandis
Sub-skin contains a large amount of cellulose, hemicellulose, lignin and pectin, so these carbonyls are very likely from acid or ester.~
1634cm-1For C=O contracting vibration, it it is xylan hemicellulose character peak；1438～1253cm-1For the saturated CH of cellulose2Scissors are shaken
Dynamic characteristic peak and the skeletal vibration of sugar ring；～1058cm-1For cellulose C-O-C stretching vibration characteristic peak；～612cm-1For sugar ring
Deformation vibration characteristic peak.Above-mentioned sign illustrates that this invention operating procedure is simple, with low cost, the amino functional absorption obtained
Agent is evenly distributed, stable in properties.
Embodiment 1 is presented herein below carries out adsorption applications to p-Hydroxybenzoate, copper, chromium and methylene blue dye etc. in water
Example.
Application examples 1:
Embodiment 1 gained amino functional shaddock peel adsorbent is applied to absorption to the methyl parahydroxybenzoate in water
(MPB), ethylparaben (EPB), propyl p-hydroxybenzoate (PPB), butyl p-hydroxybenzoate (BPB) 4 kinds are newly
Type pollutant.PH value 6.5, adsorption time 30min, to the methyl parahydroxybenzoate (MPB) in water, P-hydroxybenzoic acid
Ethyl ester (EPB), propyl p-hydroxybenzoate (PPB), the saturated extent of adsorption of butyl p-hydroxybenzoate (BPB) are respectively 680mg/
G, 685mg/g, 685mg/g, 690mg/g.
Application examples 2:
Embodiment 1 gained amino functional shaddock peel adsorbent is applied to absorption to copper (II) ion in water.PH takes
Value 4.0, adsorption time 30min, the saturated extent of adsorption to copper (II) ion is 128mg/g.
Application examples 3:
Embodiment 1 gained amino functional shaddock peel adsorbent is applied to absorption to chromium (VI) ion in water.PH takes
Value 2.5, adsorption time 30min, the saturated extent of adsorption to chromium (VI) ion is 370mg/g.
Application examples 4:
Embodiment 1 gained amino functional shaddock peel adsorbent is applied to absorption to the methylene blue dye in water.pH
Value 8.0, adsorption time 60min, the saturated extent of adsorption to methylene blue dye is 156mg/g.
Fig. 3-7 is that (Fig. 4 is 4 kinds of p-Hydroxybenzoates to amino functional ABSORBENTS ABSORPTION metal ion, and Fig. 5 is Cu
(II), Fig. 6 be Cr (VI), Fig. 7 be the adsorption isothermal curve of methylene blue dye.)
Application examples 5:
Embodiment 1 gained amino functional shaddock peel adsorbent is applied to process to contain concentration be 100mg/L's simultaneously
The waste water of the chromium (VI) of copper (II) and 200mg/L.PH value 3.0, adsorption time 60min, to copper (II) and chromium (VI) clearance
It is respectively 99.8% and 99.5%.
Fig. 8 is that different pH value amino functional shaddock peel adsorbent is adsorbed containing the copper (II) that concentration is 100mg/L simultaneously
Adsorption rate curve with the waste water of the chromium (VI) of 200mg/L.
Application examples 6: by the P-hydroxybenzoic acid of embodiment 1 gained amino functional shaddock peel adsorbent absorption 100mg/L
After ester, the HCl of the material 0.1mol/L after absorption is that desorbing agent carries out eluting, and investigates its recycling effect.Fig. 9 is ammonia
The recycling figure of base functionalization shaddock peel adsorbent absorption p-Hydroxybenzoate.Result shows pomelo peel amino functional warp
After recycling for 5 times, the adsorption efficiency of p-Hydroxybenzoate remains to keep about 90%, and material can be recycled for multiple times.
Pomelo peel modified amido functionalization adsorbent of the present invention, is experimentally confirmed: this invention operating procedure is simple,
With low cost, the pomelo peel modified amido functionalization adsorbent obtained has compact structure of fibrous tissue, and internal existence is a large amount of
Hole；Rich in the functional groups such as amino, hydroxyl and carbonyl, stable in properties；To p-Hydroxybenzoate, heavy metal and methylene in water
Base cyanine etc. has high adsorption capacity, is effectively to remove the potential adsorbent of harmful substance in waste water.Amino merit of the present invention
The modified pomelo peel adsorbing material of energyization can regenerate, and after 5 times recycle, adsorption efficiency remains to keep about 90%.
Claims (10)
1. the preparation method of a pomelo peel modified amido functionalization adsorbent, it is characterised in that: with useless pomelo peel as raw material, warp
Over cleaning, it is dried, pulverizes, sieves, then use replacement, ring-opening reaction that material is carried out surface-functionalized modification, finally give
Pomelo peel modified amido functionalization adsorbent.
The preparation method of pomelo peel modified amido functionalization adsorbent the most according to claim 1, it is characterised in that: concrete
Preparation process includes:
(1) pomelo peel is carried out, is dried, pulverizes, sieves, obtain the pomelo peel powder of pretreatment；
(2) weigh the pomelo peel powder of step (1) gained, distribute it to epoxychloropropane that volume ratio is 0.5～4:1 and have
In the mixed solution of machine solvent；The pomelo peel powder of step (1) gained and the solid-to-liquid ratio of epoxychloropropane are 20～500g:
100mL；Then 0.5-10h is reacted at 50-100 DEG C under stirring；
(3) in the reaction system of step (2) epoxidation modification, organic polyamine is added so that organic multicomponent amine is in whole reaction
The volume fraction of system solution is 10-50%；Then at 50-100 DEG C of stirring reaction 0.5-10h, sucking filtration, it is washed to pH=7；Will
Gained solid, 40-100 DEG C of drying, obtains amino functional adsorbent.
The preparation method of pomelo peel modified amido functionalization adsorbent the most according to claim 2, it is characterised in that: described
In step (1) pomelo peel dry employing natural air drying or in an oven 50-100 DEG C dry 2～24 hours；Sieve the sieve used
Son is 40-150 mesh sieve.
The preparation method of pomelo peel modified amido functionalization adsorbent the most according to claim 2, it is characterised in that: step
(2) organic solvent described in is the one in ethanol, propylene glycol, glycerol, N,N-dimethylformamide；Epoxy in step (2)
Chloropropane is 1～2:1 with organic solvent volume ratio；Pomelo peel powder is 50～200g with the solid-to-liquid ratio of epoxychloropropane:
100mL。
The preparation method of pomelo peel modified amido functionalization adsorbent the most according to claim 2, it is characterised in that: step
(3) organic multicomponent amine used in is a kind of in ethylenediamine, Diethylenetriamine, three second tetramines, tetren；Organic multicomponent amine is whole
The volume fraction of individual reaction system solution is 15-25%.Reaction temperature is 60～90 DEG C, and the response time is 1～4h, stir speed (S.S.)
Being 150～300 revs/min, drying baker baking temperature is 40-80 DEG C.
6. the pomelo peel modified amido functionalization adsorbent application in absorption pollutant.
The pomelo peel modified amido functionalization adsorbent the most according to claim 6 application in absorption pollutant, it is special
Levy and be: concrete parabens emerging pollutant, the heavy metal copper that exceeds standard, chromium, coloring matter and water in water
The absorption of the pollutant of cationic and anionic and removal.
The pomelo peel modified amido functionalization adsorbent the most according to claim 7 application in absorption pollutant, it is special
Levy and be: adsorb as follows with the method removed: under the conditions of shaken at room temperature, put into pomelo peel modified amido functionalization adsorbent,
Dosage is that in every liter of waste water, adsorbent content is 0.5～5g, and oscillation rate is 100～300 revs/min, and the time is 30～180 points
Clock.
The pomelo peel modified amido functionalization adsorbent the most according to claim 8 application in absorption pollutant, it is special
Levy and be: pomelo peel modified amido functionalization adsorbent is removed the pH condition of parabens emerging pollutant in water and is
1.0～12.0, the pH removing in water the heavy metal copper that exceeds standard is 1.0～6.0, remove the pH of chromium in water is 1.0～12.0, removes water
The pH of the pollutant that the pH condition of middle coloring matter is 1.0～12.0, remove water cationic and anionic is 3.0～4.0.
The pomelo peel modified amido functionalization adsorbent the most according to claim 8 application in absorption pollutant, it is special
Levy and be: described pomelo peel modified amido functionalization adsorbent can regenerate, the adsorbent acid after using or alkali desorption,
Through 5 times recycle after adsorption efficiency keep 90% or more than.
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