CN108982489B - Biomass cellulose-based Cu2+Preparation method and application of detection material - Google Patents

Biomass cellulose-based Cu2+Preparation method and application of detection material Download PDF

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CN108982489B
CN108982489B CN201810730946.1A CN201810730946A CN108982489B CN 108982489 B CN108982489 B CN 108982489B CN 201810730946 A CN201810730946 A CN 201810730946A CN 108982489 B CN108982489 B CN 108982489B
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朱红祥
张存智
熊建华
王磊
伍琪
陈文博
郭威
周士乐
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Guangxi University
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Abstract

The invention discloses biomass cellulose-based Cu2+The preparation method and the application of the detection material comprise the following steps: s1, oxidizing the biomass cellulose by using Tempo, and performing C6Oxidation of the hydroxyl group in position to a carboxyl group; then continuously adopting sodium periodate to oxidize the biomass cellulose, and obtaining the product C2、C3The hydroxyl on the position is oxidized into aldehyde group to prepare oxidized cellulose; s2, reacting at C through Schiff base2、C32, 5-dithio-diurea is grafted on the position to prepare modified cellulose; s3, performing amidation reaction on the mixture C6Grafting 2, 5-dithiodiurea on the position to prepare the biomass cellulose base Cu2+And (6) detecting the material. The material obtained by the method has the advantages of portability, high sensitivity and good stability, has an excellent selective recognition effect on copper ions, is not interfered by other heavy metal ions in the detection process, can detect the copper ions qualitatively and quantitatively, is suitable for field rapid detection, and has a good application prospect.

Description

Biomass cellulose-based Cu2+Preparation method and application of detection material
Technical Field
The invention relates to the technical field of heavy metal detection, and particularly relates to biomass cellulose-based Cu2+Preparation method of detection materialAnd application thereof.
Background
The heavy metal pollution problem is always the most urgent problem to be solved in water environment treatment. With the continuous development of economic society, reports about heavy metal pollution problems are frequently found in recent years. Moreover, heavy metal ions from industrial wastewater cannot be biodegraded and are easily enriched in human bodies, thereby causing damage to human organs and causing serious pathological changes. Among the existing heavy metal ions, Cu2+Has strong harmfulness, and Cu entering human body2+It can cause symptoms such as internal organ edema, and death in severe cases. There is no effective detoxification mechanism in human body, so once Cu is taken2+Stool accumulates mainly in the bones and liver, and Cu2+Poisoning does not have an effective antidote, and therefore its hazard is not negligible.
In view of Cu2+How to adopt effective detection means to the Cu with great harm to human body2+The detection is the problem which is the first solution at present. In conventional detection methods, such as Atomic Emission Spectrometry (AES), Atomic Absorption Spectrometry (AAS), inductively coupled plasma mass spectrometry (ICP-MS), Atomic Fluorescence Spectrometry (AFS), and the like, Cu is analyzed qualitatively, quantitatively, and accurately2+At the same time, it is necessary to do this in a laboratory, and at the same time, it requires expensive equipment and specialized technicians to support, which makes many field tests that need to be performed in the field impossible. Therefore, there is a need to develop new ways in which field testing can be achieved.
In recent years, researchers in various countries have developed a solid-based colorimetric functional material capable of realizing field detection, and the solid-based colorimetric functional material can realize naked eye identification by observing color change without any instrument, so as to further realize the detection of Cu2+The purpose of (1). At present, the solid-based colorimetric functional material is mainly applied to Cu by adopting a physical or chemical method2+The detection agent with color development recognition function is loaded on a paper substrate to prepare the Cu-doped copper2+The functional paper with color-developing identification is characterized in that when the detection agent is physically loaded on the paper, the detection agent is bonded on the paper baseThe detection agent is easy to fall off due to physical combination, so that the stability of the detection material is influenced; in the prior art, the problem of material detection stability is solved by chemically loading the material on the paper base, and the detection lower limit of the material is higher and the sensitivity is poorer due to less chemically loaded detection agent.
In addition to this, most solid substrates are currently used, such as: glass, silicon oxide, acrylic fiber cellulose and the like, have high price and poor plasticity, and are not beneficial to subsequent processing application or carrying.
Disclosure of Invention
The invention aims to solve the technical problem of providing biomass cellulose-based Cu2+Preparation method and application of detection material, and biomass cellulose base Cu obtained by using method2+The detection material is convenient to carry, high in sensitivity and good in stability, has an excellent selective recognition effect on copper ions, is not interfered by other heavy metal ions in the detection process, can detect the copper ions qualitatively and quantitatively, and is suitable for rapid field detection.
The invention solves the technical problems by the following technical scheme:
the invention relates to biomass cellulose-based Cu2+The preparation method of the detection material comprises the following steps:
s1, oxidizing the biomass cellulose by using Tempo, and performing C6Oxidation of the hydroxyl group in position to a carboxyl group; then continuously adopting sodium periodate to oxidize the biomass cellulose, and obtaining the product C2、C3The hydroxyl on the position is oxidized into aldehyde group to prepare oxidized cellulose;
s2, reacting at C through Schiff base2、C32, 5-dithio-diurea is grafted on the position to prepare modified cellulose;
s3, performing amidation reaction on the mixture C6Grafting 2, 5-dithiodiurea on the position to prepare the biomass cellulose base Cu2+And (6) detecting the material.
The biomass cellulose is bamboo pulp cellulose, bagasse pulp cellulose, softwood pulp cellulose or hardwood pulp cellulose.
The specific operation of step S1 of the present invention is: placing the Tempo and the biomass cellulose in an aqueous solution according to the mass ratio of 1: 2-5: 1, and carrying out oxidation reaction for 0.5-24 hours at the reaction temperature of 30-80 ℃; and then adding sodium periodate, wherein the mass ratio of the added sodium periodate to the biomass cellulose is 1: 2-5: 1, carrying out oxidation reaction for 0.5-24 hours at the reaction temperature of 30-80 ℃, and carrying out suction filtration to obtain the oxidized cellulose.
The specific operation of step S2 of the present invention is: and (3) placing the 2, 5-dithiodiurea and the oxidized cellulose obtained in the step (S1) in an aqueous solution according to the mass ratio of 1: 2-5: 1, reacting for 0.5-24 hours at the reaction temperature of 30-80 ℃ by using Schiff base, and performing suction filtration to obtain the modified cellulose.
The specific operation of step S3 of the present invention is: placing 2, 5-dithiodiurea and the modified cellulose obtained in the step S2 into an aqueous solution according to the mass ratio of 1: 2-5: 1, carrying out amidation reaction for 0.5-24 hours at the reaction temperature of 60-120 ℃, and obtaining the biomass cellulose base Cu2+And (6) detecting the material.
Biomass cellulose-based Cu of the invention2+Application of the detection material: cellulose base of biomass Cu2+The detection material is made into detection test paper, a detection film or a detection rod and is used for detecting copper ions in water or food.
The biomass cellulose base Cu prepared by the method2+The color development mechanism of the detection material is as follows: due to the introduction of 2, 5-dithiobiurea on biomass cellulose, C ═ S is broken through selective chelation with copper ions, copper sulfide is generated and deposited on the surface of the material, so that the material is changed in color, and the shade of the color is in positive correlation with the concentration of the copper ions in water.
Compared with the prior art, the invention has the following beneficial effects:
(1) c in biomass cellulose through Schiff base reaction2、C3On the basis of introduction of 2, 5-dithiodiurea in position, and then C62, 5-dithiodiurea is introduced at the position, three hydroxyl groups on a cellulose glucose unit are fully utilized, and Cu is introduced as much as possible2+The functional group is identified through color development, and the Cu content of the material is further improved2+The detection sensitivity of (3). Cu can be controlled by regulating the oxidation level of Tempo and sodium periodate2+The more the amount of the introduced color-developing recognition functional group is, the more Cu can be detected2+The lower the minimum concentration of (a), the higher the sensitivity of the material. Biomass cellulose base Cu obtained by the method2+The lower limit of the detection material on the detection of the copper ions in the water can reach 10-7mol/L。
(2) Grafting Cu by means of chemical bonding2+Biomass cellulose base Cu prepared by color development and functional group recognition2+The detection material has good chemical stability, the chromogenic identification functional group does not fall off when the detection material is applied to detecting copper ions in water, the detection stability is good, and the problem of poor physical load stability is solved.
(3) The invention adopts the biomass cellulose as the Cu prepared by the matrix2+The detection material can be directly used as a matrix of detection paper, and the problems of poor binding force between the functional group and the paper base and poor stability when the functional group is loaded on the paper base by physical impregnation are solved.
(4) Biomass cellulose base Cu prepared by the invention2+The detection material has the advantages that 2, 5-dithiobiurea is introduced to the biomass cellulose, so that the detection material has selective chelation with copper ions, C-S fracture is caused, copper sulfide is generated and deposited on the surface of the material, the color of the material is changed, the detection material has an excellent selective recognition effect on the copper ions, and the detection material is not interfered by other heavy metal ions.
(5) Biomass cellulose base Cu prepared by the invention2+The color depth of the color development of the detection material on the copper ions is in positive correlation with the concentration of the copper ions in the water, so that the detection material not only can qualitatively detect the copper ions in the water, but also can quantitatively detect the concentration of the copper ions in the water.
(6) Biomass cellulose base Cu prepared by the invention2+The detection material can be processed into detection test paper, detection membrane and detection rod, and has wide application range and convenient carrying.
(7) In practical application, the material is only required to be soaked in an aqueous solution to be detected, and the copper ions in the water can be rapidly detected through visual observation.
(8) The biomass cellulose which is most abundant in reserves in the nature, has the widest existence range and low price is used as the raw material, has the advantages of simplicity, easy obtainment and low cost, and can meet the large demands of the market.
Detailed Description
The following examples are presented to further illustrate the present invention and should not be construed as limiting the invention. It is within the scope of the present invention to make simple modifications or alterations to the methods, procedures or conditions of the present invention without departing from the spirit and substance of the invention; unless otherwise specified, the technical means used in the examples are conventional means well known to those skilled in the art.
Reagents, methods and apparatus used in the present invention are conventional in the art unless otherwise indicated. Unless otherwise indicated, reagents and materials used in the present invention are commercially available.
Example 1: biomass cellulose based Cu2+Preparation of detection Material
(1) Firstly, placing Tempo and bamboo pulp cellulose in an aqueous solution according to the mass ratio of 0.5:1, carrying out oxidation reaction for 0.5 hour at the reaction temperature of 30 ℃, adding sodium periodate into the aqueous solution, carrying out oxidation reaction for 0.5 hour at the reaction temperature of 30 ℃ and carrying out suction filtration to obtain the oxidized cellulose, wherein the mass ratio of the added sodium periodate to the bamboo pulp cellulose is 1: 2.
(2) And (2) placing the 2, 5-dithiobiurea and the oxidized cellulose obtained in the step (1) in an aqueous solution according to the mass ratio of 1:2, reacting for 0.5 hour by using Schiff base at the reaction temperature of 30 ℃, and performing suction filtration to obtain the modified cellulose.
(3) Placing 2, 5-dithiodiurea and the modified cellulose obtained in the step (2) in an aqueous solution according to the mass ratio of 1:2, carrying out amidation reaction for 0.5 hour at the reaction temperature of 60 ℃, and thus obtaining the biomass cellulose base Cu2+And (6) detecting the material.
Example 2: biomass cellulose based Cu2+Preparation of detection Material
(1) Firstly, mixing Tempo and bagasse cellulose according to a mass ratio of 5:1, placing the mixture in an aqueous solution, carrying out oxidation reaction for 24 hours at the reaction temperature of 80 ℃, adding sodium periodate into the aqueous solution, carrying out oxidation reaction for 24 hours at the reaction temperature of 80 ℃ according to the mass ratio of the added sodium periodate to the bamboo pulp cellulose of 5:1, and carrying out suction filtration to obtain the oxidized cellulose.
(2) And (2) placing 2, 5-dithiobiurea and the oxidized cellulose obtained in the step (1) in an aqueous solution according to the mass ratio of 5:1, reacting for 24 hours at the reaction temperature of 80 ℃ by using Schiff base, and performing suction filtration to obtain the modified cellulose.
(3) Putting 2, 5-dithiodiurea and the modified cellulose obtained in the step (2) into an aqueous solution according to the mass ratio of 5:1, carrying out amidation reaction for 24 hours at the reaction temperature of 120 ℃, and thus obtaining the biomass cellulose base Cu2+And (6) detecting the material.
Example 3: biomass cellulose based Cu2+Preparation of detection Material
(1) Firstly, placing Tempo and softwood pulp cellulose in an aqueous solution according to the mass ratio of 2:1, carrying out oxidation reaction for 12 hours at the reaction temperature of 50 ℃, then adding sodium periodate into the aqueous solution, carrying out oxidation reaction for 12 hours at the reaction temperature of 50 ℃ and carrying out suction filtration to obtain the oxidized cellulose, wherein the mass ratio of the added sodium periodate to the bamboo pulp cellulose is 2: 1.
(2) And (2) placing the 2, 5-dithiobiurea and the oxidized cellulose obtained in the step (1) in an aqueous solution according to the mass ratio of 2:1, reacting for 12 hours at the reaction temperature of 50 ℃ by using Schiff base, and performing suction filtration to obtain the modified cellulose.
(3) Placing 2, 5-dithiodiurea and the modified cellulose obtained in the step (2) in an aqueous solution according to the mass ratio of 2:1, carrying out amidation reaction for 12 hours at the reaction temperature of 90 ℃, and thus obtaining the biomass cellulose base Cu2+And (6) detecting the material.
Example 4: preparation of Standard colorimetric card
Preparing Cu with accurate concentration2+Standard solution, Cu2+Respectively at a concentration of 10-1mol/L，10-2mol/L，10-3mol/L， 10-4mol/L，10-5mol/L，10-6mol/L，10-7mol/L, biomass cellulose base Cu prepared in examples 1, 2 and 32+Detection material pair Cu2+The standard liquid is displayed and identified according to the materialAnd drawing standard color comparison cards according to the colors identified by the standard solution, and respectively marking the standard color comparison cards as a standard color comparison card 1, a standard color comparison card 2 and a standard color comparison card 3.
Example 5: biomass cellulose based Cu2+Detection material for Cu in water2+Detection of (2)
1. The detection method comprises the following steps: the biomass cellulose base Cu prepared in the embodiment 1 of the invention2+Processing the detection material into detection test paper, cutting the detection test paper into a rectangular paper strip with the length of 3cm and the width of 1cm, directly soaking the detection test paper into an aqueous solution to be detected, observing the color change of the detection test paper by naked eyes after soaking the detection test paper for 0.5 hour, and then comparing the color change with a standard colorimetric card 1.
2. Detection process and results: taking equal-volume solutions to be detected as 7 standard solutions of silver nitrate, copper sulfate, lead nitrate, chromium chloride, zinc chloride, magnesium sulfate and manganese sulfate, wherein the concentrations are 10-4mol/L of Biomass cellulose based Cu prepared in example 12+The detection test paper processed by the detection material is directly immersed in the solution to be detected for 0.5 hour, only the color of the detection test paper immersed in the standard copper nitrate solution is changed from white to black gray, and the concentration of copper ions in the solution is 10 by comparing with a standard colorimetric card 1-4mol/L, consistent with the concentration of the standard solution.
Example 6: biomass cellulose based Cu2+Detection material for Cu in water2+Detection of (2)
1. The detection method comprises the following steps: the biomass cellulose base Cu prepared in the embodiment 2 of the invention2+Processing the detection material into detection test paper, cutting the detection test paper into a rectangular paper strip with the length of 3cm and the width of 1cm, directly soaking the detection test paper into a to-be-detected aqueous solution for 24 hours, observing the color change of the detection test paper by naked eyes, and comparing the color change with a standard colorimetric card 2.
2. Detection process and results: respectively taking 7 standard solutions of equal volume of silver nitrate, copper sulfate, lead nitrate, chromium chloride, zinc chloride, magnesium sulfate and manganese sulfate, and uniformly mixing, wherein the concentration of copper ions is 10-4mol/L of Biomass cellulose based Cu prepared in example 22+Detecting processed materialThe test paper is directly immersed into the mixed standard solution, after being immersed for 24 hours, the color of the test paper is changed from white to black and gray, and the test paper is compared with a standard colorimetric card 2 to obtain the test paper with the copper ion concentration of 10-4mol/L, consistent with the concentration of the mixed standard solution.
Example 7: biomass cellulose based Cu2+Detection material for Cu in water2+Detection of (2)
1. The detection method comprises the following steps: the biomass cellulose-based Cu2+ detection material prepared in the embodiment 3 of the invention is processed into detection test paper, the detection test paper is cut into a rectangular paper strip with the length of 3cm and the width of 1cm, then the rectangular paper strip is directly immersed into an aqueous solution to be detected, after the rectangular paper strip is immersed for 12 hours, the color change of the detection test paper is observed by naked eyes, and then the detection test paper is compared with a standard colorimetric card 3.
2. Detection process and results: respectively taking copper sulfate standard solutions with the same volume and different concentrations, wherein the copper ion concentration is 10-1， 10-2mol/L，10-3mol/L，10-4mol/L，10-5mol/L，10-6mol/L，10-7mol/L of Biomass cellulose based Cu prepared in example 32+The detection test paper processed by the detection material is directly immersed in the aqueous solution to be detected for 12 hours, the color of the detection test paper is changed from white to black gray, and the detection test paper is compared with a standard colorimetric card 3 to obtain the detection test paper with the copper ion concentration of 10-1mol/L，10-2mol/L，10-3mol/L，10-4mol/L，10-5mol/L，10-6mol/L，10-7mol/L, consistent with the concentration of the standard solution.
Example 8: biomass cellulose based Cu2+Detection material for Cu in water2+Detection of (2)
1. The detection method comprises the following steps: the biomass cellulose base Cu prepared in the embodiment 1 of the invention2+Detection of material at pH<7, soaking the test paper in the acid solution for 12 hours, then processing the test paper into test paper, cutting the test paper into a rectangular paper strip with the length of 3cm and the width of 1cm, then directly soaking the test paper into the aqueous solution to be tested, observing the color change of the test paper by naked eyes after soaking the test paper for 12 hours, and then comparing the test paper with a standard colorimetric card 1.
2. Detection process and results: respectively taking copper sulfate standard solutions with the same volume and different concentrations, wherein the copper ion concentration is 10-1mol/L，10-2mol/L，10-3mol/L，10-4mol/L，10-5mol/L，10-6mol/L，10-7mol/L of Biomass cellulose based Cu prepared in example 12+The detection material is firstly pH-adjusted<7 soaking in the acid solution for 12 hours, processing into test paper, directly soaking in the aqueous solution to be tested for 12 hours, changing the color of the test paper from white to black gray, and comparing with the standard colorimetric card 1 to obtain the test paper with the copper ion concentration of 10-1mol/L，10-2mol/L，10-3mol/L，10-4mol/L， 10-5mol/L，10-6mol/L，10-7mol/L, consistent with the concentration of the standard solution.
Example 9: biomass cellulose based Cu2+Detection material for Cu in water2+Detection of (2)
1. The detection method comprises the following steps: the biomass cellulose base Cu prepared in the embodiment 2 of the invention2+Detection of material at pH>7, soaking the test paper in the alkaline solution for 12 hours, then processing the test paper into test paper, cutting the test paper into a rectangular paper strip with the length of 3cm and the width of 1cm, then directly soaking the test paper into the aqueous solution to be tested, observing the color change of the test paper by naked eyes after soaking the test paper for 12 hours, and then comparing the test paper with a standard colorimetric card 2.
2. Detection process and results: respectively taking copper sulfate standard solutions with the same volume and different concentrations, wherein the copper ion concentration is 10-1mol/L，10-2mol/L，10-3mol/L，10-4mol/L，10-5mol/L，10-6mol/L，10-7mol/L of Biomass cellulose based Cu prepared in example 22+Detection of material at pH>7 soaking in the alkaline solution for 12 hours, processing into test paper, directly soaking in the aqueous solution to be tested for 12 hours, changing the color of the test paper from white to black gray, and comparing with a standard colorimetric card 2 to obtain the test paper with the copper ion concentration of 10-1mol/L，10-2mol/L，10-3mol/L，10-4mol/L， 10-5mol/L，10-6mol/L，10-7mol/L, consistent with the concentration of the standard solution.
Example 10: biomass cellulose based Cu2+Detection material for Cu in water2+Detection of (2)
1. The detection method comprises the following steps: the biomass cellulose base Cu prepared in the embodiment 3 of the invention2+The detection material is soaked in an organic solvent for 12 hours and then processed into detection test paper, the detection test paper is cut into a rectangular paper strip with the length of 3cm and the width of 1cm, then the rectangular paper strip is directly soaked into a to-be-detected aqueous solution, after the detection test paper is soaked for 12 hours, the color change of the detection test paper is observed by naked eyes, and then the detection test paper is compared with a standard colorimetric card 3.
2. Detection process and results: respectively taking copper sulfate standard solutions with the same volume and different concentrations, wherein the copper ion concentration is 10-1mol/L，10-2mol/L，10-3mol/L，10-4mol/L，10-5mol/L，10-6mol/L，10-7mol/L of Biomass cellulose based Cu prepared in example 32+Soaking the detection material in an organic solvent for 12 hours, processing the detection material into detection test paper, directly soaking the detection test paper into an aqueous solution to be detected for 12 hours, changing the color of the detection test paper from white to black gray, and comparing the detection test paper with a standard colorimetric card 3 to obtain the copper ion concentrations of 10-1mol/L，10-2mol/L，10-3mol/L，10-4mol/L，10- 5mol/L， 10-6mol/L，10-7mol/L, consistent with the concentration of the standard solution.
The detection results of the examples 5-10 show that the biomass cellulose base Cu prepared by the method2+Detection material pair Cu2+Has excellent selective recognition function, is not interfered by other heavy metal ions in the detection process, has high detection sensitivity, and has the lower limit of 10 for detecting copper ions in water-7mol/L, has good stability, and can still treat Cu after being soaked in acidic solution, alkaline solution and organic solvent2+Has excellent selective recognition function, can realize qualitative and quantitative detection of copper ions in water, and is suitable for on-site rapid detection.

Claims (2)

1. Biomass cellulose-based Cu2+The preparation method of the detection material is characterized by comprising the following steps:
s1, oxidizing the biomass cellulose by using Tempo, and performing C6Oxidation of the hydroxyl group in position to a carboxyl group; then continuously adopting sodium periodate to oxidize the biomass cellulose, and obtaining the product C 2、C3The hydroxyl on the position is oxidized into aldehyde group to prepare oxidized cellulose; the biomass cellulose is bamboo pulp cellulose, bagasse pulp cellulose, softwood pulp cellulose or hardwood pulp cellulose;
s2, reacting at C through Schiff base2、C32, 5-dithio-diurea is grafted on the position to prepare modified cellulose;
s3, performing amidation reaction on the mixture C6Grafting 2, 5-dithiodiurea on the position to prepare the biomass cellulose base Cu2+Detecting the material;
the specific operation of step S1 is: placing the Tempo and the biomass cellulose in an aqueous solution according to the mass ratio of 1: 2-5: 1, and carrying out oxidation reaction for 0.5-24 hours at the reaction temperature of 30-80 ℃; then adding sodium periodate, wherein the mass ratio of the added sodium periodate to the biomass cellulose is 1: 2-5: 1, carrying out oxidation reaction for 0.5-24 hours at the reaction temperature of 30-80 ℃, and carrying out suction filtration to obtain oxidized cellulose;
the specific operation of step S2 is: placing 2, 5-dithiodiurea and the oxidized cellulose obtained in the step S1 in an aqueous solution according to the mass ratio of 1: 2-5: 1, reacting for 0.5-24 hours at the reaction temperature of 30-80 ℃, and performing suction filtration to obtain modified cellulose;
the specific operation of step S3 is: placing 2, 5-dithiodiurea and the modified cellulose obtained in the step S2 into an aqueous solution according to the mass ratio of 1: 2-5: 1, carrying out amidation reaction for 0.5-24 hours at the reaction temperature of 60-120 ℃, and obtaining the biomass cellulose base Cu2+And (6) detecting the material.
2. The biomass cellulose-based Cu of claim 12+Of materials to be testedUse of a cellulose base of biomass, Cu2+The detection material is made into detection test paper, a detection film or a detection rod and is used for detecting copper ions in water or food.
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