CN108166090B - Preparation method of oxidized cellulose nanofibrils based on phosphoric acid and hydrogen peroxide - Google Patents
Preparation method of oxidized cellulose nanofibrils based on phosphoric acid and hydrogen peroxide Download PDFInfo
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- CN108166090B CN108166090B CN201810173527.2A CN201810173527A CN108166090B CN 108166090 B CN108166090 B CN 108166090B CN 201810173527 A CN201810173527 A CN 201810173527A CN 108166090 B CN108166090 B CN 108166090B
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title claims abstract description 34
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 229920002201 Oxidized cellulose Polymers 0.000 title claims abstract description 21
- 229940107304 oxidized cellulose Drugs 0.000 title claims abstract description 21
- 229910000147 aluminium phosphate Inorganic materials 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000002028 Biomass Substances 0.000 claims abstract description 16
- 239000002244 precipitate Substances 0.000 claims abstract description 12
- 239000002994 raw material Substances 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 235000019441 ethanol Nutrition 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 6
- 239000006228 supernatant Substances 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 241000609240 Ambelania acida Species 0.000 claims description 4
- 239000010905 bagasse Substances 0.000 claims description 4
- 241001494508 Arundo donax Species 0.000 claims description 3
- 244000166124 Eucalyptus globulus Species 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 23
- 238000005406 washing Methods 0.000 abstract description 5
- 238000000926 separation method Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- 239000002114 nanocomposite Substances 0.000 abstract description 2
- 229920002678 cellulose Polymers 0.000 description 18
- 239000001913 cellulose Substances 0.000 description 18
- 235000010980 cellulose Nutrition 0.000 description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 229920001046 Nanocellulose Polymers 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000000265 homogenisation Methods 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000010041 electrostatic spinning Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002121 nanofiber Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 108010059892 Cellulase Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 244000082204 Phyllostachys viridis Species 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- -1 bark Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001523 electrospinning Methods 0.000 description 1
- 230000005686 electrostatic field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000010297 mechanical methods and process Methods 0.000 description 1
- 230000005226 mechanical processes and functions Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 210000001724 microfibril Anatomy 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002159 nanocrystal Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008104 plant cellulose Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/02—Oxycellulose; Hydrocellulose; Cellulosehydrate, e.g. microcrystalline cellulose
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
The invention discloses a preparation method of oxidized cellulose nanofibrils based on phosphoric acid and hydrogen peroxide, which comprises the following operation steps: mixing a biomass raw material, concentrated phosphoric acid with the mass concentration of 85% and hydrogen peroxide with the mass concentration of 50%, stirring and reacting for 96 hours at the temperature of 5-35 ℃, then adding absolute ethyl alcohol to terminate the reaction, standing and layering the solution, pouring out the supernatant, retaining the lower-layer precipitate, sequentially washing the lower-layer precipitate with the absolute ethyl alcohol, the ethyl alcohol with the volume concentration of 50% and water, and treating by using a high-pressure homogenizer to obtain the oxidized cellulose nanofibril. The method has simple and convenient process, less chemical varieties and low price, and the prepared oxidized cellulose nano-fibril has wide application prospect in the fields of water treatment, oil-water separation, nano composite materials and the like.
Description
Technical Field
The invention belongs to the technical field of nanocellulose manufacturing, and particularly relates to a method for directly preparing oxidized cellulose nanofibrils from biomass.
Background
The nano-cellulose not only has the characteristics of renewable and biodegradable natural cellulose, but also has the advantages of large specific surface area, high hydrophilicity, high transparency, high strength, high Young modulus, low thermal expansion coefficient and the like, provides possibility for forming various functional composite materials, and has wide application prospect. The biomass has the advantages of wide source, abundant reserves, reproducibility and environmental friendliness. Starting from biomass, the acquisition of biomass resources in various morphologies, in particular the manipulation, design and assembly of natural cellulose in the nanometer size range, has become a hot topic of current research in the field.
The preparation of the nano-cellulose comprises the following steps: preparation of nano microcrystalline cellulose (NCC). The NCC is obtained by hydrolyzing strong acid or cellulase to remove an amorphous area of cellulose and reserving a compact crystalline area, has a needle-shaped whisker structure (the diameter is 5-70 nm, the length is 100-400 nm), and has high crystallinity (60-90%). And (II) preparing hairy cellulose nano crystal (HC-NC), wherein amorphous regions are obtained by cutting by chemical agents, crystalline regions are similar to NCC (the diameter is 5-10 nm, the length is 100-200 nm), and amorphous regions at two ends have a plurality of polymer high molecular chains (the length is about 100 nm). However, the high-intensity hydrolysis can cause a great amount of cellulose degradation, the product yield is low, and the requirement on equipment is high. (III) preparation of microfibrillated cellulose (MFC). MFC is also called nanofibril cellulose and cellulose nanofiber, is in a fibrillar shape, has the diameter of 5-60 nm and the length of 1000-10000 nm, has flexibility, and has a molecular structure consisting of a crystalline region and an amorphous region alternately. The method has the following defects: (1) MFC is typically prepared by mechanical processes (e.g., high pressure homogenization), where cellulose is extracted from the feedstock by chemical pretreatment, followed by high-intensity mechanical forces (e.g., high pressure homogenization, high shear, microfluidization, milling, etc.) to break and fibrillate the cellulose. The preparation process of the high-pressure homogenization method generally has less pollution to the environment, but has high requirements on equipment and huge energy consumption. (2) MFC is prepared by a TEMPO oxidation method, TEMPO (piperidine nitroxide radical) -NaBr-NaClO is used for selectively oxidizing hydroxyl at the C6 position on a glucose unit into carboxyl, and electrostatic repulsion force of ionization of the carboxyl on the surface of the fiber is used for promoting the separation of the fiber. Other methods for preparing nanocellulose, such as etherification, oxidation, esterification, carboxymethylation, etc., have a similar principle to the TEMPO oxidation method. The method has mild reaction conditions and simple operation, and is the most commonly adopted method at present. The disadvantages of these methods are that raw materials need to be pretreated (including cooking, multi-stage bleaching, etc.), and the whole process consumes a lot of resources such as electricity, heat, chemical reagents and water. (3) The MFC is prepared by an electrostatic spinning method, and the concentrated cellulose solution passes through a metal needle-shaped injector and is stably extruded under the induction action of a high-voltage electrostatic field to prepare the nano-cellulose. The nano-fiber obtained by electrostatic spinning has smooth surface, uniform diameter distribution and indefinite length. Electrospinning nanocellulose is an energy intensive process and dissolution of cellulose is difficult. (IV) preparation of Bacterial Nanocellulose (BNC). BNC is produced by biological polymerization of glucose by bacteria under the action of biological enzyme, has crystallinity higher than that of plant cellulose, indefinite length, diameter of 20-100 nm, high tensile strength and good shape maintaining capability. The bacterial method can regulate and control the structure, crystal form, particle size distribution and the like of the prepared cellulose, and in addition, the method has low energy consumption and no pollution. However, domestic research is still in the primary stage, and the problems of low yield, high cost, long production period, difficult regulation and control of processing technology and the like exist, so that large-scale industrialization is difficult to realize.
The oxidized cellulose nano-fibril has large length-diameter ratio, good dispersibility and functional groups such as carboxyl and the like, and is an important natural cellulose derivative. Oxidized cellulose nanofibrils are currently the most commonly used method for preparation by means of TEMPO oxidation, which uses TEMPO (piperidine nitroxide radical) -NaBr-NaClO to selectively oxidize the hydroxyl group at the C6 position on the glucose unit to a carboxyl group, and uses electrostatic repulsion of the ionization of the carboxyl group on the surface of the filaments to facilitate the separation of the filaments. Other methods for preparing nanocellulose, such as etherification, oxidation, esterification, carboxymethylation, etc., have a similar principle to the TEMPO oxidation method. The disadvantages of these methods are that raw materials need to be pretreated (including cooking, multi-stage bleaching, etc.), the whole process consumes a lot of electricity, heat, chemical reagents, water, etc., and the high-strength pretreatment process results in that the natural microfibril structure is broken to different degrees, and the polymerization degree of cellulose is greatly reduced.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a preparation method of oxidized cellulose nanofibrils based on phosphoric acid and hydrogen peroxide, and the method is based on a phosphoric acid dissolving system, introduces a hydrogen peroxide oxidizing reagent and can directly prepare the oxidized cellulose nanofibrils from biomass.
The invention solves the technical problems by the following technical scheme:
the invention relates to a preparation method of oxidized cellulose nanofibrils based on phosphoric acid and hydrogen peroxide, which comprises the following operation steps: mixing a biomass raw material, concentrated phosphoric acid with the mass concentration of 85% and hydrogen peroxide with the mass concentration of 50%, stirring and reacting for 96 hours at the temperature of 5-35 ℃, then adding absolute ethyl alcohol to terminate the reaction, standing and layering the solution, pouring out the supernatant, retaining the lower-layer precipitate, sequentially washing the lower-layer precipitate with the absolute ethyl alcohol, the ethyl alcohol with the volume concentration of 50% and water, and treating by using a high-pressure homogenizer to obtain the oxidized cellulose nanofibril.
The biomass raw material, the concentrated phosphoric acid and the hydrogen peroxide are in the following ratio: 10g biomass raw material, 30ml concentrated phosphoric acid: 20-60 ml of hydrogen peroxide.
The biomass raw materials comprise bagasse, arundo donax slices and eucalyptus bark slices.
Compared with the prior art, the invention has the following beneficial effects:
(1) the preparation process is simple and convenient, does not need high-strength pretreatment, and is suitable for large-scale industrial production;
(2) the raw materials used in the invention comprise all available biomass, such as bagasse, bark, bamboo and the like, and also comprise biomass such as unutilized weeds, shrubs and the like;
(3) the invention has the advantages that the adopted chemicals are few in types and easy to obtain and low in price;
(4) the oxidized cellulose nano-fibril prepared by the invention has wide application prospect in the fields of water treatment, oil-water separation, nano composite materials and the like.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims.
Example 1
Adding 10g of bagasse, 30ml of phosphoric acid with the mass concentration of 85% and 20ml of hydrogen peroxide with the mass concentration of 50% into a 500ml three-neck flask, stirring and reacting for 96h at 5 ℃, adding absolute ethyl alcohol to stop the reaction, transferring the solution into a 500ml measuring cylinder, standing and layering, pouring out the supernatant, retaining the precipitate at the lower layer, sequentially washing the precipitate at the lower layer with the absolute ethyl alcohol, the ethyl alcohol with the volume concentration of 50% and the water, and treating by a high-pressure homogenizer to obtain the oxidized cellulose nanofibril.
The diameter of the obtained oxidized cellulose nano-fibril is 20-100 nm, and the carboxyl content is 0.653 mmol/g.
Example 2
Adding 10g of arundo donax linn, 30ml of concentrated phosphoric acid with the mass concentration of 85% and 60ml of hydrogen peroxide with the mass concentration of 50% into a 500ml three-neck flask, stirring and reacting for 96 hours at 25 ℃, adding absolute ethyl alcohol to stop the reaction, transferring the solution into a 500ml measuring cylinder, standing and layering, pouring out the supernatant, retaining the lower-layer precipitate, sequentially washing the lower-layer precipitate with the absolute ethyl alcohol, the ethyl alcohol with the volume concentration of 50% and the water, and treating by a high-pressure homogenizer to obtain the oxidized cellulose nanofibrils.
The diameter of the obtained oxidized cellulose nano-fibril is 20-100 nm, and the carboxyl content is 0.734 mmol/g.
Example 3
Adding 10g of eucalyptus bark slices, 30ml of concentrated phosphoric acid with the mass fraction of 85% and 45ml of hydrogen peroxide with the mass concentration of 50% into a 500ml three-neck flask, stirring and reacting for 96 hours at 35 ℃, adding absolute ethyl alcohol to stop the reaction, transferring the solution into a 500ml measuring cylinder, standing and layering, pouring out the supernatant, retaining the precipitate at the lower layer, sequentially washing the precipitate at the lower layer with the absolute ethyl alcohol, the ethyl alcohol with the volume concentration of 50% and the water, and treating by a high-pressure homogenizer to obtain the oxidized cellulose nanofibrils.
The diameter of the obtained oxidized cellulose nano-fibril is 20-100 nm, and the carboxyl content is 0.819 mmol/g.
Claims (1)
1. A preparation method of oxidized cellulose nanofibrils based on phosphoric acid and hydrogen peroxide is characterized by comprising the following operation steps: mixing a biomass raw material, concentrated phosphoric acid with the mass concentration of 85% and hydrogen peroxide with the mass concentration of 50%, stirring and reacting for 96 hours at the temperature of 5-35 ℃, adding absolute ethyl alcohol to stop the reaction, standing and layering the solution, pouring out supernatant, retaining lower-layer precipitates, sequentially cleaning the lower-layer precipitates with the absolute ethyl alcohol, the ethyl alcohol with the volume concentration of 50% and water, and treating by using a high-pressure homogenizer to obtain oxidized cellulose nanofibrils;
the biomass raw material, the concentrated phosphoric acid and the hydrogen peroxide are in the following ratio: 10g biomass raw material, 30ml concentrated phosphoric acid: 20-60 ml of hydrogen peroxide;
the biomass raw materials comprise bagasse, arundo donax slices and eucalyptus bark slices.
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