CN111841438A - Solubilizing material for restoring PCE pollution in underground environment and preparation method thereof - Google Patents
Solubilizing material for restoring PCE pollution in underground environment and preparation method thereof Download PDFInfo
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- CN111841438A CN111841438A CN202010716010.0A CN202010716010A CN111841438A CN 111841438 A CN111841438 A CN 111841438A CN 202010716010 A CN202010716010 A CN 202010716010A CN 111841438 A CN111841438 A CN 111841438A
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- C07F7/02—Silicon compounds
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- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/0876—Reactions involving the formation of bonds to a Si atom of a Si-O-Si sequence other than a bond of the Si-O-Si linkage
- C07F7/0878—Si-C bond
- C07F7/0879—Hydrosilylation reactions
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- C09K17/00—Soil-conditioning materials or soil-stabilising materials
- C09K17/40—Soil-conditioning materials or soil-stabilising materials containing mixtures of inorganic and organic compounds
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Abstract
The invention relates to a solubilizing material for restoring PCE (Poly-Ether) pollution in an underground environment and a preparation method thereof. The trisiloxane surfactant is used for replacing the traditional hydrocarbon surfactant, and the solubilization capacity is larger compared with the traditional hydrocarbon surfactant solution or the mixed compound solution thereof by taking the mixed solution prepared from the cosurfactant, salt and water as a solubilization material; the invention can be used for repairing the chlorohydrocarbon pollution of underground water and soil and has wide application.
Description
Technical Field
The invention belongs to the technical field of environmental engineering, and particularly relates to a high-efficiency solubilizing material for chlorinated hydrocarbon pollutants in an underground environment and a synthetic method thereof, in particular to a solubilizing material for restoring PCE (Poly-acetyl-L-CoA synthetase) pollution in the underground environment and a preparation method thereof.
Background
Currently, chlorinated hydrocarbons are widely used as dry cleaning agents, metal degreasing solvents, refrigerator refrigerants, and the like. However, due to production, use, storage and improper disposal, chlorinated hydrocarbons can enter the environment through volatilization, leakage, waste water discharge, pesticide use, etc., and become a major source of pollution to the atmosphere, soil and water. Among them, Tetrachloroethylene (PCE) is an organic chemical that is difficult to degrade, colorless with fragrance, transparent, volatile, denser than water, has lower water solubility and higher interfacial tension, and belongs to heavy Non-water soluble Phase Liquid (DNAPL). After entering soil and underground water environment, the water can stay in the environment for a long time due to the adsorbability and the stability, so that long-term pollution is caused. Therefore, the exploration and development of efficient restoring technology for chlorinated hydrocarbon pollution are of great significance for protecting ecological environment and promoting human health.
The surfactant-enhanced remediation technology is widely considered as a method for effectively removing DNAPL, and the method utilizes the solubilization or flow-increasing effect of a surfactant material to improve the solubility or the fluidity of hydrophobic organic pollutants in a water phase, so as to remove the pollutants and achieve the remediation purpose. In the existing research and engineering repair, a non-ionic or anionic surfactant solution is often selected as a solubilizing material, such as Sodium Dodecyl Sulfate (SDS), Tween 80(Tween 80), and the like. The anionic surfactant is selected as a solubilizing material, although the adsorption loss is small when the anionic surfactant is applied underground, the anionic surfactant is limited by a krafft point, and the surfactant is volatilized in an underground low-temperature environment. Nonionic surfactants, while causing adsorptive losses in subterranean environments, are generally superior to anionic surfactants in low temperature resistance. However, the solubilizing ability is limited when a single nonionic or anionic surfactant solution or a mixed solution thereof is used as the solubilizing material.
The surfactant, cosurfactant and salt solution can spontaneously form a transparent dispersion system, namely microemulsion, with the oil phase. The microemulsion is a thermodynamically stable system, has a proper organic microenvironment, has a larger micelle size compared with a surfactant solution, can provide a larger storage space for an oil phase, has a strong stability-enhancing solubilization characteristic, and is expected to obtain a solubilization effect better than that of the surfactant solution. Therefore, if a non-ionic surfactant which is applicable to the underground low-temperature environment is selected, and the mixed solution of the cosurfactant, the salt and the water can spontaneously form a micro-emulsion system with the oil phase of the pollutant, the mixed solution as a solubilizing material has better solubilizing potential for the chlorinated hydrocarbon pollutant of the underground environment.
Among the surfactants, silicone surfactants are those having a hydrophobic group of silicone instead of a hydrocarbon chain in a hydrocarbon surfactant, and hydrophilic groups of other groups such as a polyoxyethylene chain, a carboxyl group, a ketone group, an amino group, and an epoxy group. Compared with the hydrophobic skeleton of the hydrophobic group of the hydrocarbon surfactant and methylene, the siloxane skeleton of the hydrophobic group of the siloxane surfactant has high flexibility, methyl is spread on an oil/water interface in an umbrella-shaped structure, and the siloxane surfactant has the advantages of compact interface arrangement, high surface activity, excellent wettability, large hydrophobic group space, environmental friendliness and no toxic or side effect. In addition, the branched structure of the trisiloxane can improve the surface activity of the interface, reduce the overlapping of tail chains and have stronger steric hindrance, so that the flocculation effect among microemulsion drops of a microemulsion system formed by taking the trisiloxane surfactant as a main material is weakened, and the stable microemulsion is more favorably formed. The siloxane surfactant is widely used in the aspects of textiles, plastics, agricultural additives, chemicals, medicines, automobiles and the like, and the research of applying the synthesized organosilicon double-end-capped surfactant to oil displacement is reported, but the research of applying the siloxane surfactant to the remediation of chlorinated hydrocarbon pollutants is not seen yet.
At present, most solubilizing materials for chlorinated hydrocarbon pollutants are hydrocarbon surfactants or mixed and compounded solutions thereof, and a micro-emulsion system formed by the solubilizing materials and the pollutants is rarely reported. Chinese patent CN 102601110A discloses a device and a method for remedying tetrachloroethylene soil pollution, which use single and mixed surfactants SDS and Tween 80 as solubilizing reagents for PCE to wash soil columns. However, the optimal mixed surfactant is better than the solubilizing effect of a single surfactant solution in comparison with the solubilizing effect of the PCE, but the solubility of the optimal mixed surfactant in the PCE solution is not more than 2 orders of magnitude higher than that of the PCE solution, and the solubilizing capability is limited.
Therefore, the method has practical application significance for restoring the chlorinated hydrocarbon pollution in the underground environment by exploring and developing the chlorinated hydrocarbon pollutant solubilizing material which is efficient, safe, low-temperature resistant and simple in preparation method.
Disclosure of Invention
The invention aims to provide a solubilizing material for restoring PCE (Poly-axial-flow computed tomography) pollution in an underground environment, which overcomes the defects that the conventional solubilizing material for chlorinated hydrocarbon pollutants has limited solubilizing capability and cannot be applied to restoring PCE pollution in the underground low-temperature environment. Also provided is a method for preparing a solubilizing material for restoration of PCE contamination in underground environment, which is a siloxane surfactant (NSS-EO)n-OH, n is 7,10) is used as a main material, a mixed solution of Isopropanol (IPA), sodium chloride (NaCl) and water is used as a solubilizing material, PCE is wrapped by utilizing the ultralow interfacial tension of an interfacial film formed by the solubilizing material, a stable microemulsion system is spontaneously formed, the solubility of a chlorinated hydrocarbon water phase is improved, the solubilization of the PCE is realized, and the repair efficiency is further improved.
The purpose of the invention is realized by the following technical scheme:
a solubilizing material for repairing PCE pollution in an underground environment comprises the following components in percentage by mass:
said N isSS-EOn-OH is a nonionic polyether modified trisiloxane surfactant, structural formula:
further, the solubilizing material for repairing PCE pollution comprises the following components in percentage by mass:
the preparation method of the solubilizing material for restoring the PCE pollution in the underground environment comprises the following steps:
A. preparation of nonionic polyether-modified trisiloxane surfactant (NSS-EOn-OH, n ═ 7, 10):
activating allyl polyether and platinum catalyst under vacuum nitrogen condition, and then carrying out hydrosilylation reaction with 1,1,1,3,5,5, 5-heptamethyltrisiloxane to generate colorless transparent oily liquid NSS-EOn-OH(n＝7,10)；
B. And B, mixing the nonionic polyether modified trisiloxane surfactant synthesized in the step A with co-surfactant Isopropanol (IPA), NaCl and water according to mass fraction to obtain the solubilizing material.
Further, step a, the platinum catalyst is a Speier catalyst or a Karstedt catalyst.
Further, step A, the activation temperature is 80 ℃, and the activation time is 30 minutes.
Further, in the step A, the reaction temperature of the addition reaction is 94 ℃, and the reaction time is 2-3 hours.
Further, the molar ratio of the heptamethyltrisiloxane to the allyl polyether is 1: 0.93.
further, the amount of the catalyst used was 0.0015% by mass of heptamethyltrisiloxane in terms of platinum content.
Compared with the prior art, the invention has the beneficial effects that:
1. book (I)NSS-EO as the main material of solubilizing material of the inventionn-OH (n is 7,10), the preparation method is simple and convenient, has no high-temperature and high-pressure conditions, short reaction time, greenness, no toxicity, low price and easy industrial production;
2. the main material of the solubilizing material of the present invention, NSS-EOn-OH (n-7, 10), which has good surface activity and can effectively reduce the surface tension of an aqueous solution;
3. the solubilizing material is simple to prepare, clear and transparent, and the components are nontoxic and low in price;
4. the solubilizing material is contacted with the pollutant PCE, and a transparent and thermodynamically stable microemulsion system is formed in a short time;
5. after the solubilizing material and the PCE form microemulsion, the solubility of the PCE in water is increased, and in the optimal mass ratio, the concentration of the PCE is 27.9g/L which is 186 times of the solubility (150mg/L,25 ℃) of the PCE in clear water;
6. the solubilizing material of the invention can be suitable for underground low-temperature environment;
7. the invention can optimize the quality ratio suitable for the actual pollution situation according to the actual PCE pollution situation, for example, the PCE can be used for the pollution remediation of soil or underground water, and has good popularization prospect.
Drawings
FIG. 1 is a schematic representation of example 2NSS-EO of the present inventionn-infrared spectrum of OH surfactant;
FIG. 2 is example 3NSS-EO of the present inventionn-a plot of the surface tension change of aqueous solutions of a range of concentrations of OH (n-7, 10) surfactant;
FIG. 3 is a technical scheme of the preparation method of the solubilizing material for repairing PCE contamination in underground environment of the present invention.
Detailed Description
The present invention will be described in further detail with reference to specific embodiments below:
example 1
Preparation of NSS-EOn-OH(n＝7,10)
A dry three-neck flask with a reflux condenser pipe, a constant pressure dropping funnel and a magnetic stirrer is filledNitrogen for 10 min; adding allyl polyether into a dry three-neck flask, adding chloroplatinic acid (Speier catalyst) diluted by isopropanol or Karstedt platinum catalyst as a catalyst, heating to 80 ℃ in an oil bath magnetic stirrer, activating for 30 minutes, and then heating to 94 ℃; gradually dripping 1,1,1,3,5,5, 5-heptamethyltrisiloxane by using a constant-pressure funnel to perform hydrosilylation reaction for 2-3 hours; cooling, adding 2% of activated carbon to adsorb and separate out the platinum catalyst, and performing color removal and suction filtration; distilling under reduced pressure to remove solvent and low boiling point substances (unreacted heptamethyltrisiloxane and allyl polyether) to obtain colorless transparent oily liquid NSS-EOn-OH (n ═ 7, 10). The molar ratio of heptamethyltrisiloxane to allyl polyether is 1: 0.93; the catalyst (calculated as platinum content) was 0.0015% by mass of heptamethyltrisiloxane.
Example 2
Taking the colorless transparent oily liquid in the example 1, mixing with potassium bromide, grinding, tabletting and performing infrared spectrum measurement, wherein: 2250-2100 cm of trisiloxane polyoxyethylene ether-1The stretching vibration absorption peak of Si-H disappears; 3392cm-1Is positioned at 2872cm of-OH stretching vibration absorption peak-1Is represented by-CH2Has a stretching vibration absorption peak of 1646cm-1is-CH ═ CH21107cm as the peak of the stretching vibration absorption-1The peak is the vibration absorption peak of Si-O-Si, which proves the synthesis of the trisiloxane polyoxyethylene ether. Conform to NSS-EOnStructural features of-OH, as shown in figure 1.
Example 3
The product NSS-EO of example 1 was takenn(ii) preparing an aqueous solution having a mass concentration of-OH (n-7, 10) of 0.05g/L, 0.1g/L, 0.2g/L, 0.3g/L, 0.4g/L, 0.5g/L, 1.0g/L, 2.0g/L, 3.0g/L, and measuring the NSS-EOnSurface tension of-OH (n ═ 7,10) solution to give NSS-EO7The Critical Micelle Concentration (CMC) of-OH was 0.5g/L (8.7X 10)-4mol/L) and a surface tension of about 22mN/m to obtain NSS-EO10Critical Micelle Concentration (CMC) of-OH is 0.4g/L (5.5X 10-4mol/L), a surface tension of about 17mN/m is shown in FIG. 2.
Example 4
With NSS-EOn-OH(n＝7) Formulation of solubilizing Material for principal Material
Preparing 9 colorimetric tubes with covers, wherein the mass ratio of oil to water is 1: 1, modulation of NSS-EOn-OH (n ═ 7), IPA, NaCl, three factor concentration levels.
Example 5
Adding a solubilizing material into each colorimetric tube, correspondingly adding PCE, and standing at room temperature for 10 hours. After standing, the microemulsion phase state was observed, the formed microemulsion was taken, and the PCE concentration was determined.
Experimental results show that except the experimental groups No. 6 and No. 7, the solubilizing materials in the other experimental groups have solubilizing effect on the PCE, and the solubility of the PCE in water is 0.150g/L higher than the concentration (25 ℃) of the PCE in clean water.
Example 6
With NSS-EOn-OH (n-10) as main material
Preparing 12 colorimetric tubes with covers, wherein the mass ratio of oil to water is 1: 1, modulation of NSS-EOn-OH (n ═ 10), IPA, NaCl, three factor concentration levels.
Example 7
Adding a solubilizing material into each colorimetric tube, correspondingly adding PCE, and standing at room temperature for 10 hours. After standing, the microemulsion phase state was observed, the formed microemulsion was taken, and the PCE concentration was determined.
Experimental results show that the solubilizing materials in the experimental groups have solubilizing effects on the PCE, and the solubility of the PCE in water is 0.150g/L higher than the concentration (25 ℃) of the PCE in clean water. In the experiment group No. 16, the solubilizing material and the PCE form Winsor III type microemulsion, and the solubility of the PCE is the highest.
Example 8
Preparing 3 colorimetric tubes with covers, taking solubilizing materials of Winsor III type microemulsion formed by experimental groups 16, 19 and 21 and PCE, adding the solubilizing materials into each colorimetric tube, correspondingly adding the PCE, and standing at room temperature for 10 hours. After standing, the microemulsion phase was observed and the volume of each phase was recorded.
Example 9
The experimental groups No. 22, 23 and 24 in the example 8 are taken and put into a thermostat with the temperature of 10 ℃, the microemulsion is kept stand, the phase state of the microemulsion is observed, and the volume of each phase is recorded.
The experimental result shows that in the experimental group colorimetric tube in the 10 ℃ incubator, the volume of the middle phase is slightly reduced compared with that of the normal temperature, the volume of the PCE phase is almost unchanged, and the solubilizing effect is still achieved in the low-temperature environment.
Claims (8)
1. The solubilizing material for restoring PCE (prestressed soil engineering) pollution in the underground environment is characterized by comprising the following components in percentage by mass:
the NSS-EOn-OH is a nonionic polyether modified trisiloxane surfactant, and the structural formula of the surfactant is as follows:
n＝7,10。
2. the solubilizing material for restoration of PCE pollution in the underground environment as claimed in claim 1, which is characterized by consisting of the following components in percentage by mass:
3. the preparation method of the solubilizing material for restoration of PCE pollution in the underground environment, as claimed in claim 1, comprises the following steps:
A. preparation of nonionic polyether modified trisiloxane surfactant:
activating allyl polyether and a platinum catalyst under the vacuum nitrogen condition, and then carrying out hydrosilylation reaction on the activated allyl polyether and 1,1,1,3,5,5, 5-heptamethyltrisiloxane to generate NSS-EOn-OH (n is 7,10) which is colorless transparent oily liquid;
B. and B, mixing the nonionic polyether modified trisiloxane surfactant synthesized in the step A with a cosurfactant IPA, NaCl and water according to mass fraction to obtain the solubilizing material.
4. The preparation method of the solubilizing material for restoration of PCE pollution in the underground environment, as claimed in claim 1, wherein: step A, the platinum catalyst is a Speier catalyst or a Karstedt catalyst.
5. The preparation method of the solubilizing material for restoration of PCE pollution in the underground environment as claimed in claim 1, characterized by the following steps A: the activation temperature is 80 ℃, and the activation time is 30 minutes.
6. The preparation method of the solubilizing material for restoration of PCE pollution in the underground environment, as claimed in claim 1, wherein: and step A, the reaction temperature of the addition reaction is 94 ℃, and the reaction time is 2-3 hours.
7. The preparation method of the solubilizing material for restoration of PCE pollution in the underground environment, as claimed in claim 1, wherein: the molar ratio of the heptamethyltrisiloxane to the allyl polyether is 1: 0.93.
8. the preparation method of the solubilizing material for restoration of PCE pollution in the underground environment, as claimed in claim 1, wherein: the amount of the catalyst is 0.0015% of the mass of the heptamethyltrisiloxane in terms of platinum content.
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| CN113816983A (en) * | 2021-11-04 | 2021-12-21 | 枣阳市华威硅氟材料有限公司 | Method for catalyzing hydrosilylation reaction by using p-cymene ruthenium dichloride dimer |
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