CN104445629A - Novel method for improving tyrosinase-based catalytic degradation of phenol pollutant - Google Patents
Novel method for improving tyrosinase-based catalytic degradation of phenol pollutant Download PDFInfo
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- CN104445629A CN104445629A CN201310419177.0A CN201310419177A CN104445629A CN 104445629 A CN104445629 A CN 104445629A CN 201310419177 A CN201310419177 A CN 201310419177A CN 104445629 A CN104445629 A CN 104445629A
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Abstract
The invention discloses a novel method for improving tyrosinase-based catalytic degradation of a phenol pollutant and relates to the technical field of phenol pollutant degradation. The novel method comprises the following steps that tyrosinase and 1-ethyl-3-methylimidazole alanine ionic liquid are mixed according to a ratio of 1: 80 to form a mixed solution, the mixed solution is added with a high-concentration phenol compound solution, a high-concentration phenol compound solution is added into tyrosinase with a concentration the same as that of tyrosinase used in the step a, experiment results of a 1-ethyl-3-methylimidazole alanine ionic liquid use group and a blank group are compared so that an o-dihydroxybenzene generation rate is obtained. The novel method has easy processes, is environmentally friendly, produces pollution-less catalytic degradation products and is economic and efficient.
Description
Technical field:
The present invention relates to the degradation technique field of phenol pollutent, be specifically related to a kind of novel method strengthening tyrosinase catalysis degradation of phenol pollutent.
Background technology:
Phenol is that Germanization scholar dragon lattice found in coal tar in 1834, therefore has another name called phenylic acid (Carbolic acid), is the simplest phenol organic matter, a kind of weak acid.Have off-odor, corrodibility is extremely strong, and its strong solution has strong impulse effect to skin.And during World War II, phenol is also used as in Nazi concentration camp to execute a convict.And phenol has strong corrosive nature to skin and mucous membrane, nervus centralis or infringement Liver and kidney function can be suppressed.Phenol acute poisoning, namely absorbs high concentration phenol steam and can cause the symptom such as headache, dizzy, weak, the dimness of vision, pulmonary edema, occur acute renal failure.Because phenol is to the toxicity of environment and human body, US Gov Env Protection Agency is classified as excellent control pollutent.Simultaneously, phenol is the intermediate of resol, water reducer, polycarbonate and dihydroxyphenyl propane downstream industry, relevant to terminal markets such as domestic construction industry, automobile industry, household electrical appliances, the development of these industries, causes the increase of domestic phenol yield (estimating can reach 3,400,000 tons in 2013).The phenol of excessive production pollutes water body and air, serious harm physical environment and human health, and therefore, in research water, the removal of phenol is very necessary.
In recent years, for improving the removal efficiency of phenol in water further, Chinese scholars has done a large amount of research work in water in phenol process, and develops multiple treatment process.At present, mainly the methods such as ultrasonic degradation phenol, ozone oxidation degradation of phenol, zeolite-loaded tellurium dioxide Photocatalytic Degradation of Phenol are adopted.Although the methods such as ultrasonic degradation and zeolite-loaded tellurium dioxide photocatalytic degradation can obtain good degradation efficiency, need the external world to provide light source, Ultrasonic Conditions, there is certain application limitation.And room temperature biocatalysis edman degradation Edman has operation more simply, the advantage of more environmental protection, has become one of the most promising persistence organic pollutant innoxious process for treating paid close attention to various countries.
Summary of the invention:
The object of this invention is to provide a kind of novel method strengthening tyrosinase catalysis degradation of phenol pollutent, it is easily prepared, environmental protection, catalyzed degradation product is pollution-free, and economical, efficient.
In order to solve the problem existing for background technology, the present invention is by the following technical solutions: its catalyzed degradation method steps is: a, mixed in the ratio of 1:80 with 1-ethyl-3-methylimidazole L-Ala ionic liquid by tyrosine oxidase, obtains the two mixing solutions;
B, in the two mixing solutions, add the oxybenzene compound solution of high density, a 240-360nm length scanning is carried out at interval for 4 minutes;
C, with the oxybenzene compound solution (concentration is identical with b) adding high density in same concentrations tyrosine oxidase in a, a 240-360nm length scanning is carried out at interval for 4 minutes, does control experiment;
D, contrast 1-ethyl-3-methylimidazole L-Ala ionic liquid add group and blank group experimental result, obtain pyrocatechol generating rate, thus systematic comparison 1-ethyl-3-methylimidazole L-Ala ionic liquid are on the impact of tyrosinase catalysis efficiency.
In the present invention, amino acid ion liquid strengthens the principle of tyrosinase catalysis degradation of phenol pollutent: amino acid ion liquid provides a biocompatibility microenvironment by the mode such as electrostatic attraction, ionic bonding forces for tyrosine oxidase, keeps tyrosine oxidase biological activity and stability.Tyrosine oxidase has oxygenase and desaturase two kinds of activity, the hydroxylation of catalysis of phenol compound selective can generate the lower pyrocatechol of toxicity (catechol is the organic phenol usually existed in fruit and vegetables, belongs to vegetable tannin composition).
The present invention adds 1-3mg mL
-11-ethyl-3-methylimidazole L-Ala ionic liquid is to 0.02-0.05mg mL
-1tyrosine oxidase (enzyme activity>=1000unit mg
-1) in solution, compare 1-ethyl-3-methylimidazole L-Ala ionic liquid to tyrosinase catalysis degradation of phenol Pollutant effects by UV, visible light method system.
Due in ultraviolet-visible wavelength scope (240-360nm), 0.25mmol L
-1phenol solution uv-absorbing very weak (can ignore).And newly-generated pyrocatechol is at 275nm wavelength place, there is larger ultraviolet absorption peak; And pyrocatechol grows out of nothing, sensitivity is higher, therefore selects monitoring pyrocatechol as monitoring peak.The degradation rate of phenol is indirectly reflected from the generating rate of pyrocatechol.
The degradation rate of phenol is obtained by the generating rate indirect calculation of pyrocatechol, with the generating rate assessment 1-ethyl-3-methylimidazole L-Ala ionic liquid of pyrocatechol on the impact of tyrosinase catalysis efficiency, and the raising multiple of catalytic efficiency can be calculated.
The testing process of tyrosinase catalysis degradation of phenol is divided into following step:
In the applying unit time of the present invention, the increasing amount of pyrocatechol absorption peak evaluates the size of tyrosinase catalysis ability: n is pyrocatechol ultraviolet absorption peak strength, the i.e. absorbance of pyrocatechol; M is pyrocatechol ultraviolet absorption peak strength under original state, the absorbance (original state do not have pyrocatechol to generate be designated as 0) of pyrocatechol when namely phenol has just added tyrosinase solution; T is phenol and tyrosine oxidase action time; W is that tyrosinase catalysis generates pyrocatechol rate value (i.e. tyrosinase catalysis degradation of phenol rate value).Tyrosinase catalysis degradation of phenol rate value calculation formula is as follows:
w=(n-m)/t
Described 1-ethyl-3-methylimidazole L-Ala ionic liquid, its chemical general formula is C
9h
18o
2n
3, English full name is 1-ethyl-3-methyl imidazolium Alanine (Emimn [Ala]), and positively charged ion is C6H11N2 (1-ethyl-3-methylimidazole), and negatively charged ion is C3H7O2N (L-Ala).
The chemical general formula of described ionic liquid is C
9h
18o
2n
3.
Described catalyzer adopts following process to prepare, first the bromic ether of mol ratio 1:1 and nitrogen Methylimidazole is got in round-bottomed flask under 50 degrees Celsius after reaction, vacuum condition goes down except moisture, has prepared ionic liquid intermediate 1-ethyl-3-methyllimidazolium bromide; Hydroxide 1-ethyl-3-methylimidazole is prepared subsequently by 100 centimetres of ion exchange resin; Hydroxide salt and L-Ala underpressure distillation are stirred 12 hours, filters rear 80 DEG C of vacuum-dryings 2 days.
Described tyrosine oxidase and the 1-ethyl-3-methylimidazole L-Ala ionic liquid catalysis of phenol that acts synergistically is degraded.
Relative to prior art, tool of the present invention has the following advantages:
1, tyrosine oxidase and amino acid ion liquid are mainly derived from nature amino acid and tyrosine oxidase, and raw material is green and cheap and easy to get, belongs to green catalyst.
2, utilize amino acid ion liquid and tyrosine oxidase concerted catalysis degradation of phenol efficiency high.
3, equipment is simple, after catalyzer simply mixes with phenol pollutent, or processes further and is immobilizedly positioned in phenol environment, just can reach the object of degraded under cold condition.
Accompanying drawing illustrates:
Fig. 1 is that in the inventive method, 1-ethyl-3-methylimidazole L-Ala ionic liquid and tyrosine oxidase concerted catalysis degradation of phenol simulate schematic diagram;
Fig. 2 is the ultraviolet-visible spectrogram of pyrocatechol in the present invention;
Fig. 3 is the time m-absorption intensity figure that in the present invention, tyrosine oxidase concerted catalysis degradation of phenol generates pyrocatechol.
Embodiment:
Referring to figs. 1 through Fig. 3, this embodiment by the following technical solutions: the catalyzed degradation method steps that it comprises is: a, mixed in the ratio of 1:80 with 1-ethyl-3-methylimidazole L-Ala ionic liquid by tyrosine oxidase, obtains the two mixing solutions;
B, in the two mixing solutions, add the oxybenzene compound solution of high density, a 240-360nm length scanning is carried out at interval for 4 minutes;
C, with the oxybenzene compound solution (concentration is identical with b) adding high density in same concentrations tyrosine oxidase in a, a 240-360nm length scanning is carried out at interval for 4 minutes, does control experiment;
D, contrast 1-ethyl-3-methylimidazole L-Ala ionic liquid add group and blank group experimental result, obtain pyrocatechol generating rate, thus systematic comparison 1-ethyl-3-methylimidazole L-Ala ionic liquid are on the impact of tyrosinase catalysis efficiency.
In this embodiment, amino acid ion liquid strengthens the principle of tyrosinase catalysis degradation of phenol pollutent: amino acid ion liquid provides a biocompatibility microenvironment by the mode such as electrostatic attraction, ionic bonding forces for tyrosine oxidase, keeps tyrosine oxidase biological activity and stability.Tyrosine oxidase has oxygenase and desaturase two kinds of activity, the hydroxylation of catalysis of phenol compound selective can generate the lower pyrocatechol of toxicity (catechol is the organic phenol usually existed in fruit and vegetables, belongs to vegetable tannin composition).
This embodiment adds 1-3mg mL
-11-ethyl-3-methylimidazole L-Ala ionic liquid is to 0.02-0.05mg mL
-1tyrosine oxidase (enzyme activity>=1000unit mg
-1) in solution, compare 1-ethyl-3-methylimidazole L-Ala ionic liquid to tyrosinase catalysis degradation of phenol Pollutant effects by UV, visible light method system.
Due in ultraviolet-visible wavelength scope (240-360nm), 0.25mmol L
-1phenol solution uv-absorbing very weak (can ignore).And newly-generated pyrocatechol is at 275nm wavelength place, there is larger ultraviolet absorption peak; And pyrocatechol grows out of nothing, sensitivity is higher, therefore selects monitoring pyrocatechol as monitoring peak.The degradation rate of phenol is indirectly reflected from the generating rate of pyrocatechol.
The degradation rate of phenol is obtained by the generating rate indirect calculation of pyrocatechol, with the generating rate assessment 1-ethyl-3-methylimidazole L-Ala ionic liquid of pyrocatechol on the impact of tyrosinase catalysis efficiency, and the raising multiple of catalytic efficiency can be calculated.
The testing process of tyrosinase catalysis degradation of phenol is divided into following step:
In this embodiment applying unit time, the increasing amount of pyrocatechol absorption peak evaluates the size of tyrosinase catalysis ability: n is pyrocatechol ultraviolet absorption peak strength, the i.e. absorbance of pyrocatechol; M is pyrocatechol ultraviolet absorption peak strength under original state, the absorbance (original state do not have pyrocatechol to generate be designated as 0) of pyrocatechol when namely phenol has just added tyrosinase solution; T is phenol and tyrosine oxidase action time; W is that tyrosinase catalysis generates pyrocatechol rate value (i.e. tyrosinase catalysis degradation of phenol rate value).Tyrosinase catalysis degradation of phenol rate value calculation formula is as follows:
w=(n-m)/t
Described 1-ethyl-3-methylimidazole L-Ala ionic liquid, its chemical general formula is C
9h
18o
2n
3, English full name is 1-ethyl-3-methyl imidazolium Alanine (Emim [Ala]), and positively charged ion is C6H11N2 (1-ethyl-3-methylimidazole), and negatively charged ion is C3H7O2N (L-Ala).
The chemical general formula of described ionic liquid is C
9h
18o
2n
3.
Described catalyzer adopts following process to prepare, first the bromic ether of mol ratio 1:1 and nitrogen Methylimidazole is got in round-bottomed flask under 50 degrees Celsius after reaction, vacuum condition goes down except moisture, has prepared ionic liquid intermediate 1-ethyl-3-methyllimidazolium bromide; Hydroxide 1-ethyl-3-methylimidazole is prepared subsequently by 100 centimetres of ion exchange resin; Hydroxide salt and L-Ala underpressure distillation are stirred 12 hours, filters rear 80 DEG C of vacuum-dryings 2 days.
Described tyrosine oxidase and the 1-ethyl-3-methylimidazole L-Ala ionic liquid catalysis of phenol that acts synergistically is degraded.
This embodiment tool has the following advantages:
1, tyrosine oxidase and amino acid ion liquid are mainly derived from nature amino acid and tyrosine oxidase, and raw material is green and cheap and easy to get, belongs to green catalyst.
2, utilize amino acid ion liquid and tyrosine oxidase concerted catalysis degradation of phenol efficiency high.
3, equipment is simple, after catalyzer simply mixes with phenol pollutent, or processes further and is immobilizedly positioned in phenol environment, just can reach the object of degraded under cold condition.
Embodiment:
In Fig. 2, dotted portion represents that tyrosine oxidase degradation of phenol generates the ultraviolet-visible spectrogram of pyrocatechol; Bold portion represents that 1-ethyl-3-methylimidazole L-Ala ionic liquid and tyrosine oxidase concerted catalysis degradation of phenol generate the ultraviolet-visible spectrogram of pyrocatechol, and the reaction times is 0,4,8,12,16,20 minute from top to bottom successively;
In Fig. 3, curve a represents that tyrosine oxidase degradation of phenol generates the time m-absorption intensity figure of pyrocatechol, and curve b represents that 1-ethyl-3-methylimidazole L-Ala ionic liquid and tyrosine oxidase concerted catalysis degradation of phenol generate the time m-absorption intensity figure of pyrocatechol.
1, the preparation of 1-ethyl-3-methylimidazole L-Ala ionic liquid
1) first get equimolar ratio bromic ether and nitrogen Methylimidazole joins in round-bottomed flask, react 3 hours at 50 DEG C, subsequently in a vacuum by moisture evaporative removal, prepared ionic liquid intermediate 1-ethyl-3-methyllimidazolium bromide;
2) by 100 centimetres of ion exchange resin, bromide anion is exchanged removal and prepare alkali ionic liquid (hydroxide 1-ethyl-3-methylimidazole);
3) by hydroxide salt (alkali ionic liquid) and the reaction of L-Ala ion generation acid-base neutralisation, underpressure distillation stirs 12 hours, obtain 1-ethyl-3-methylimidazole L-Ala ionic liquid, subsequent filtration, 80 DEG C of vacuum-drying 2 days, obtains the 1-ethyl-3-methylimidazole L-Ala ionic liquid removing moisture.
2, tyrosinase catalysis degradation of phenol generates pyrocatechol
By 1.6mg mL
-1tyrosine oxidase (50 μ L) join in the quartz colorimetric utensil of 3mL, add the phosphoric acid buffer of 2.4mL pH7.0 subsequently (containing 0.25mmol L
-1phenol), after shaking up, namely start to carry out UV-Vis scans, scanning wavelength scope is 250 ~ 370nm, and scanning interval is 1nm.Every 4 minutes, carry out single pass.Finally using the absorption peak strength at Catechol 2 75nm place as absorption value, carried out a data gathering every 4 minutes.Degradation rate value is calculated according to image data result.
3,1-ethyl-3-methylimidazole L-Ala ionic liquid strengthens tyrosinase catalysis degradation of phenol generation pyrocatechol
By 500 μ L12.9mg mL
-11-ethyl-3-methylimidazole L-Ala ionic liquid and 50 μ L1.6mg mL
-1tyrosine oxidase mixing, under electrostatic attraction and hydrogen bond action, the two combines composition mixture, joins in the quartz colorimetric utensil of 3mL subsequently by mixture, continues to add the phosphoric acid buffer of 2.4mL pH7.0 (containing 0.25mmol L
-1phenol), after shaking up, namely start to carry out UV-Vis scans, scanning wavelength scope is 250 ~ 370nm, and scanning interval is 1nm.Every 4 minutes, carry out single pass.Finally using the absorption peak strength at Catechol 2 95nm place as absorption value (because adding of amino acid ion liquid causes the absorption peak of pyrocatechol to there occurs Red Shift Phenomena), carried out a data gathering every 4 minutes.Degradation rate value is calculated according to image data result.The speed of tyrosinase catalysis degradation of phenol before and after contrast 1-ethyl-3-methylimidazole L-Ala ionic liquid adds, the catalysis obtaining 1-ethyl-3-methylimidazole L-Ala ionic liquid increases multiple.
From experimental result, the interpolation of 1-ethyl-3-methylimidazole L-Ala ionic liquid makes the efficiency of tyrosine oxidase degradation of phenol improve 10 times, its major cause is: 1,1-ethyl-3-methylimidazole L-Ala ionic liquid by electrostatic adsorption force by near phenol rich to tyrosine oxidase molecule, can add the concentration of phenol near tyrosine oxidase; 2,1-ethyl-3-methylimidazole L-Ala ionic liquid good biocompatibility, adds stability and the biological activity of tyrosine oxidase; 3, according to the literature, 1-ethyl-3-methylimidazole L-Ala ionic liquid also has low-temperature catalyzed activity.For above-mentioned reasons, 1-ethyl-3-methylimidazole L-Ala ionic liquid clearly enhances the ability of tyrosinase catalysis degradation of phenol.
Claims (5)
1. one kind strengthens the novel method of tyrosinase catalysis degradation of phenol pollutent, it is characterized in that its catalyzed degradation method steps is: (a), mixed in the ratio of 1:80 with 1-ethyl-3-methylimidazole L-Ala ionic liquid by tyrosine oxidase, obtain the two mixing solutions; (b), in the two mixing solutions, add the oxybenzene compound solution of high density, a 240-360nm length scanning is carried out at interval for 4 minutes; (c), with (a) in add the oxybenzene compound solution of high density in same concentrations tyrosine oxidase, a 240-360nm length scanning is carried out at interval for 4 minutes, does control experiment; D (), contrast 1-ethyl-3-methylimidazole L-Ala ionic liquid add group and blank group experimental result, obtain pyrocatechol generating rate, thus systematic comparison 1-ethyl-3-methylimidazole L-Ala ionic liquid is on the impact of tyrosinase catalysis efficiency.
2. a kind of novel method strengthening tyrosinase catalysis degradation of phenol pollutent according to claim 1, it is characterized in that described amino acid ion liquid strengthens the principle of tyrosinase catalysis degradation of phenol pollutent: amino acid ion liquid by the mode such as electrostatic attraction, ionic bonding forces for tyrosine oxidase provides a biocompatibility microenvironment, keep tyrosine oxidase biological activity and stability, tyrosine oxidase has oxygenase and desaturase two kinds of activity, the hydroxylation of catalysis of phenol compound selective can generate the lower pyrocatechol of toxicity.
3. a kind of novel method strengthening tyrosinase catalysis degradation of phenol pollutent according to claim 1, it is characterized in that described 1-ethyl-3-methylimidazole L-Ala ionic liquid, its chemical general formula is C
9h
18o
2n
3, positively charged ion is C6H11N2, and negatively charged ion is C3H7O2N.
4. a kind of novel method strengthening tyrosinase catalysis degradation of phenol pollutent according to claim 1, it is characterized in that described catalyzer adopts following process to prepare, first the bromic ether of mol ratio 1:1 and nitrogen Methylimidazole is got in round-bottomed flask under 50 degrees Celsius after reaction, vacuum condition goes down except moisture, has prepared ionic liquid intermediate 1-ethyl-3-methyllimidazolium bromide; Hydroxide 1-ethyl-3-methylimidazole is prepared subsequently by 100 centimetres of ion exchange resin; Hydroxide salt and L-Ala underpressure distillation are stirred 12 hours, filters rear 80 DEG C of vacuum-dryings 2 days.
5. a kind of novel method strengthening tyrosinase catalysis degradation of phenol pollutent according to claim 1, is characterized in that described tyrosine oxidase and the 1-ethyl-3-methylimidazole L-Ala ionic liquid catalysis of phenol that acts synergistically is degraded.
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Cited By (1)
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| CN113968949A (en) * | 2020-07-24 | 2022-01-25 | 博特新材料泰州有限公司 | High-adaptability water reducing agent based on biological amino acid and preparation method and application thereof |
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| CN113968949A (en) * | 2020-07-24 | 2022-01-25 | 博特新材料泰州有限公司 | High-adaptability water reducing agent based on biological amino acid and preparation method and application thereof |
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Application publication date: 20150325 |