CN108541707B - Application of star-shaped multi-cation-based compound as bactericide - Google Patents

Application of star-shaped multi-cation-based compound as bactericide Download PDF

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CN108541707B
CN108541707B CN201810272933.4A CN201810272933A CN108541707B CN 108541707 B CN108541707 B CN 108541707B CN 201810272933 A CN201810272933 A CN 201810272933A CN 108541707 B CN108541707 B CN 108541707B
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bactericide
star
reaction
cation
based compound
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CN108541707A (en
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王晨
王霞
辛燕
杨晓武
费贵强
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Kente Catalysts Inc.
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters

Abstract

The invention discloses application of a star multi-cation-based compound as a bactericide, and synthesizes a high-performance star multi-quaternary ammonium salt bactericide. The bactericide can effectively inhibit hydration expansion and dispersion migration of clay under extremely low dosage. The molecule of the cationic bactericide with dense charges contains eighteen quaternary ammonium salt groups, so that the cationic bactericide can simultaneously act on negatively charged clay particles at multiple points, and the adsorption degree is high, thereby achieving the purposes of low dosage and high anti-swelling rate. The cationic bactericide with dense charges can be widely applied to the treatment of oily sewage in oil fields.

Description

Application of star-shaped multi-cation-based compound as bactericide
Technical Field
The invention relates to the technical field of preparation of multi-quaternary ammonium salt cationic surfactants, and particularly relates to application of a star multi-cationic-group compound as a bactericide.
Background
The oilfield water injection system often contains a large amount of bacteria, such as sulfate reducing bacteria, iron bacteria, saprophytic bacteria and the like, which are widely existed in anaerobic slurry, sediments of fresh water, salt water and seawater habitats, metal conveying pipelines and other environments, and can corrode metal equipment, cause the increase of slime of a circulating water system, block pipelines, influence heat exchange efficiency, deteriorate water quality and reduce the treatment effect of water treatment agents, thus bringing inconvenience to production. At present, the method for controlling bacteria in oil fields is mainly to put in quaternary ammonium salt bactericides, such as dodecyl dimethyl benzyl ammonium chloride (1227), dodecyl trimethyl ammonium chloride (1231) and the like, and the sterilization mechanism of quaternary ammonium salt mainly damages plasma membranes for controlling cell permeability, so that bacteria are killed. However, the bactericide has many defects in an oilfield flooding system, and mainly has the defects of short effective duration of the bactericide, easy generation of drug resistance of microorganisms to the bactericide, large using dosage, high cost, more foams during use, difficult removal and the like. Therefore, research and production of a novel stable and strong-adaptability oil field bactericide for replacing the existing quaternary ammonium salt bactericide is an important and realistic research topic.
Disclosure of Invention
The invention aims to provide an application of a star-shaped multi-cation-based compound as a bactericide, which is applied to oil and gas exploitation by synthesizing a cation bactericide with dense charges.
In order to achieve the purpose, the invention adopts the following technical scheme:
the application of the star multi-cation-based compound as a bactericide has the structural formula:
Figure GDA0002418200880000021
wherein R1-is alkyl; r2-is-H or
Figure GDA0002418200880000022
Preferably, R1-is-CH3or-CH2CH3。
Preferably, R1-is C12～C18Alkyl group of (1).
The star-shaped multi-cation-based compound is applied as a bactericide, and the addition concentration is 10-50 mg/L.
The preparation method of the star-shaped multi-cation-based compound comprises the following steps:
adding trimethylolpropane-tris (3-aziridinyl propionate) reaction liquid into methylamine or ethylamine aqueous solution or long-chain fatty primary amine ethanol solution and an acid catalyst to perform aziridine ring-opening reaction, and reacting at 40-70 ℃ for 5-7 h;
under the alkalescent condition, adding methyl chloride or benzyl chloride reaction liquid into the reactant for quaternization, and reacting for 10-16 h at 50-70 ℃ under the protection of nitrogen; removing insoluble substances after the reaction is finished, concentrating the reaction solution, purifying and separating the product by using a toluene column chromatography, and drying in vacuum until the weight is constant to obtain the product.
In the aziridine ring opening reaction, trimethylolpropane-tris (3-aziridinylpropionate) and methylamine or ethylamine were in a molar ratio of 1: 3.
In the aziridine ring-opening reaction, the acidic catalyst is a phosphoric acid aqueous solution with the mass fraction of 85 percent, and the dosage of the acidic catalyst is 1 percent of the total mass of the raw materials.
In the quaternization reaction, under the alkalescent condition, the pH value is 9-10, and K is used for reaction liquid2CO3And adjusting to alkalescence.
In the quaternization reaction, the amount of methyl chloride or benzyl chloride is 6 times as much as trimethylolpropane-tris (3-aziridinyl propionate).
Compared with the prior art, the invention has the following advantages:
the invention redesigns the molecular structure of the quaternary ammonium salt bactericide to synthesize the multi-cation-based star bactericide. The multi-cation-based star bactericide has stronger bactericidal activity, and because the molecules have a plurality of quaternary ammonium salt groups, the density of positive charges on nitrogen atoms in the molecules is increased through the induction action, so that the bactericide molecules are favorably adsorbed on the surfaces of bacteria, the permeability of cell walls is changed, and the thalli are broken; in addition, after the bactericide is adsorbed to the surface of thallus, three long-chain hydrophobic groups are arranged in the molecule, which is favorable for leading the hydrophobic groups and the hydrophilic groups to respectively penetrate into a lipoid layer and a protein layer of thallus cells to cause enzyme inactivation and protein denaturation, and the cationic bactericide with dense charges has stronger bactericidal capability due to the combined effect of the two functions. The bactericide is expected to replace the existing quaternary ammonium salt bactericide and oxidation type bactericide, and plays a great role in the sterilization process of the oilfield water injection system.
The star-shaped bactericide has stronger bactericidal ability. Because the surface of a microbial cell is negatively charged, and phospholipid and some membrane protein contained in the cell membrane are also negatively charged by hydrolysis, the invention designs the star-shaped bactericide containing six quaternary ammonium salt groups, increases the positive charge density, is favorable for the adsorption of bactericide molecules on the surface of bacteria, thereby changing the permeability of cell walls, breaking thalli and improving the sterilization effect.
Because the molecules contain a plurality of quaternary ammonium salt groups, the positive charge density of nitrogen atoms in the molecules is increased through induction, which is beneficial to the adsorption of bactericide molecules on the surface of bacteria, thereby changing the permeability of cell walls and breaking thalli; in addition, after the bactericide is adsorbed to the surface of thallus, three long-chain hydrophobic groups are arranged in the molecule, which is favorable for leading the hydrophobic groups and the hydrophilic groups to respectively penetrate into a lipoid layer and a protein layer of thallus cells to cause enzyme inactivation and protein denaturation, and the cationic bactericide with dense charges has stronger bactericidal capability due to the combined effect of the two functions. The bactericide is expected to replace the existing quaternary ammonium salt bactericide and oxidation type bactericide, and plays a great role in the sterilization process of the oilfield water injection system.
Detailed Description
The invention adopts the following technical scheme:
Figure GDA0002418200880000041
wherein R1-is-CH3or-CH2CH3Or R1is-CH3or-CH2CH3；R2-is-H or
Figure GDA0002418200880000042
According to the reaction mechanism, the invention adopts the following technical scheme
A star-shaped multi-quaternary ammonium salt bactericide has a structural formula as follows:
Figure GDA0002418200880000043
wherein R1-is-CH3or-CH2CH3Or R1is-CH3or-CH2CH3；R2-is-H or
Figure GDA0002418200880000051
The method for preparing the star-shaped multi-quaternary ammonium salt bactericide comprises the following steps:
loading 20-70% by mass of methylamineDropwise adding trimethylolpropane-tris (3-aziridinyl propionate) reaction liquid into an (or ethylamine) water solution or a reaction bottle filled with a long-chain aliphatic primary amine ethanol solution and an acid catalyst to perform aziridine ring-opening reaction, wherein the molar ratio of the trimethylolpropane-tris (3-aziridinyl propionate) to methylamine (or ethylamine) is 1:3, and reacting for 5-7 h at 40-70 ℃; then using K to react the reaction solution2CO3And (3) adjusting the pH value to be alkalescent (9-10), adding methyl chloride (or benzyl chloride) reaction liquid to perform a second-step quaternization reaction, wherein the amount of the methyl chloride (or benzyl chloride) is 6 times of that of trimethylolpropane-tris (3-aziridinyl propionate), and reacting at 50-70 ℃ for 10-16 h under the protection of nitrogen. Removing insoluble substances after the reaction is finished, concentrating the reaction solution, purifying and separating the product by using a toluene column chromatography, and drying in vacuum until the weight is constant to obtain the product.
Example 1
(1) In a reactor containing 20% by mass of methylamine water solution (23.25g, containing 4.65g, 0.15mol of methylamine) and acidic catalyst (85% H)3PO40.30g), heated to 40 ℃, and then added dropwise with a 70% by mass fraction aqueous solution (35.42g, containing 21.25g, 0.05mol of trimethylolpropane-tris (3-aziridinyl propionate) over 40 min. After the dropwise addition, the temperature is raised to 70 ℃ for reaction for 5 hours.
(2) Using K as the reaction solution2CO3Adjusting to be alkalescent (pH is 9-10), dropwise adding a chloromethane ethanol solution (25.25g, wherein the chloromethane is 15.15g and 0.30mol) with the mass fraction of 60% under the protection of nitrogen, and reacting at 50 ℃ for 10 hours; removing insoluble substances after the reaction is finished, concentrating the reaction solution, purifying and separating the product by using a toluene column chromatography, and drying in vacuum to constant weight to obtain the product.
The structural formula of the product obtained in example 1 is:
Figure GDA0002418200880000061
1H NMR(300MHz，DMSO)：δ3.91(s，6H)，3.67(m，18H)，3.26(m，33H)，2.70(t，6H)，1.67(m，2H)，1.27(t，36H)，0.84(t，3H)ppm。
13C NMR(300MHz，DMSO)：δ173.5，66.1，54.1～56.8，49.5，35.7，27.3，23.0，7.9～8.3ppm。
example 2
(1) In a 70% ethylamine water solution (9.54g, containing 6.75g of ethylamine and 0.15mol) and an acid catalyst (85% H)3PO40.30g), heated to 50 ℃, and then added dropwise with a 70% by mass fraction aqueous solution (35.42g, containing 21.25g, 0.05mol of trimethylolpropane-tris (3-aziridinyl propionate) over 40 min. After the dropwise addition, the temperature is raised to 70 ℃ for reaction for 7 hours.
(2) Using K as the reaction solution2CO3Adjusting to be alkalescent (pH is 9-10), dropwise adding 80% benzyl chloride ethanol solution (47.48g, wherein 37.98g of benzyl chloride is contained, 0.30mol) under the protection of nitrogen, and reacting at 70 ℃ for 16 h; removing insoluble substances after the reaction is finished, concentrating the reaction solution, purifying and separating the product by using a toluene column chromatography, and drying in vacuum until the weight is constant to obtain the product.
The structural formula of the product obtained in example 2 is:
Figure GDA0002418200880000071
1H NMR(300MHz，DMSO)：δ7.16～7.25(m，60H)，4.50(s，24H)，3.94(s，6H)，3.63～3.68(m，18H)，3.28(m，6H)，2.70(t，6H)，1.69(m，2H)，1.25(t，12H),0.83(t，3H)ppm。
13C NMR(300MHz，DMSO)：δ173.1，125.3～131.6，65.9，60.4，54.2～56.6，35.7，27.3，23.0，7.7～8.3ppm。
evaluation of Performance
According to the oil and gas standard SY/T5329-2012 'water quality index and analysis method for clastic rock oil reservoir water injection', a secondary repetition method is adopted to test the sterilization effect of the sample of the embodiment on the oily sewage. The liquid in the test bottle turns black or has black precipitate, namely Sulfate Reducing Bacteria (SRB) is present; the liquid in the test bottle turns yellow or turbid from red, which indicates that the liquid contains saprophytic bacteria (TGB). The bactericidal effect of the samples of examples 1 and 2 is shown in tables 1 and 2.
Table 1 evaluation results of bactericidal effect of sample of example 1
Figure GDA0002418200880000072
Table 2 evaluation results of bactericidal effect of sample of example 2
Figure GDA0002418200880000073
Figure GDA0002418200880000081
Tables 1 and 2 show that the samples of examples 1 and 2 have good bactericidal effects against bactericidal effects such as Sulfate Reducing Bacteria (SRB) and saprophytic bacteria (TGB) in oily sewage.
Example 3
(1) In a mixture of an 80% ethanol solution (34.69g, containing 27.75g, 0.15mol of primary dodecylamine) of a primary dodecylamine and an acidic catalyst (85% H)3PO40.50g), heated to 50 ℃, and then 70 percent by mass of trimethylolpropane-tris (3-aziridinyl propionate) ethanol solution (35.42g, which contains 21.25g of trimethylolpropane-tris (3-aziridinyl propionate) and 0.05mol) is added dropwise for 40 min. After the dropwise addition, the temperature is raised to 70 ℃ for reaction for 6 hours.
(2) Using K as the reaction solution2CO3Adjusting to be alkalescent (pH is 9-10), dropwise adding a chloromethane ethanol solution (25.25g, wherein the chloromethane is 15.15g and 0.30mol) with the mass fraction of 60% under the protection of nitrogen, and reacting at 50 ℃ for 10 hours; removing insoluble substances after the reaction is finished, concentrating the reaction solution, purifying and separating the product by using a toluene column chromatography, and drying in vacuum to constant weight to obtain the product.
The structural formula of the product obtained in example 3 is:
Figure GDA0002418200880000082
1H NMR(300MHz，DMSO)：δ3.94(s，6H)，3.63～3.68(m，18H)，3.30(s，36H)，3.22(t，6H)，2.69(t，6H)，1.68～1.71(m，8H)，1.26～1.29(s，54H)，0.83～0.88(m，12H)ppm。
13C NMR(300MHz，DMSO)：δ173.1，65.9，64.4，61.8，58.8～59.1，52.0～52.3，35.7，31.9，29.3～29.6，26.8，25.4，22.7，14.1，7.3ppm。
example 4
(1) In a reaction vessel containing 80% by mass of an ethanol solution of primary octadecylamine (50.53g, containing 40.43g, 0.15mol of primary octadecylamine) and an acidic catalyst (85% H)3PO40.60g), heated to 50 ℃, and then 70 percent by mass of trimethylolpropane-tris (3-aziridinyl propionate) ethanol solution (35.42g, which contains 21.25g of trimethylolpropane-tris (3-aziridinyl propionate) and 0.05mol) is added dropwise for 40 min. After the dropwise addition, the temperature is raised to 50 ℃ for reaction for 8 hours.
(2) Using K as the reaction solution2CO3Adjusting to be alkalescent (pH is 9-10), dropwise adding 80% benzyl chloride ethanol solution (47.48g, wherein 37.98g of benzyl chloride is contained, 0.30mol) under the protection of nitrogen, and reacting at 70 ℃ for 16 h; removing insoluble substances after the reaction is finished, concentrating the reaction solution, purifying and separating the product by using a toluene column chromatography, and drying in vacuum until the weight is constant to obtain the product.
The structural formula of the product obtained in example 4 is:
Figure GDA0002418200880000091
1H NMR(300MHz，DMSO)：δ7.16～7.25(m，60H)，4.5(s，24H)，3.63～3.68(m，18H)，3.22(t，6H)，2.69(t，6H)，1.69～1.71(m，8H)，1.26～1.29(s，90H)，0.83(t，12H)ppm。
13C NMR(300MHz，DMSO)：δ173.1，125.7～131.6，65.9，60.8～54.6，35.7，22.7～31.9，14.1，7.1ppm。
example 5
(3) In a solution of 80% by mass of an ethanol solution of a primary tetradecyl amine (40.03g, containing 32.03g of a primary tetradecyl amine, 0.15mol) and an acidic catalyst (85% H)3PO40.50g), heated to 50 ℃, and then 70 percent by mass of trimethylolpropane-tris (3-aziridinyl propionate) ethanol solution (35.42g, which contains 21.25g of trimethylolpropane-tris (3-aziridinyl propionate) and 0.05mol) is added dropwise for 40 min. After the dropwise addition, the temperature is raised to 60 ℃ for reaction for 7 hours.
(4) Using K as the reaction solution2CO3Adjusting to be alkalescent (pH is 9-10), dropwise adding 80% benzyl chloride ethanol solution (47.48g, wherein 37.98g of benzyl chloride is contained, 0.30mol) under the protection of nitrogen, and reacting at 60 ℃ for 12 h; removing insoluble substances after the reaction is finished, concentrating the reaction solution, purifying and separating the product by using a toluene column chromatography, and drying in vacuum until the weight is constant to obtain the product.
Example 6
(1) In a solution containing 80% by mass of an ethanol solution of primary hexadecylamine (45.29g, containing 36.23g, 0.15mol of primary hexadecylamine) and an acidic catalyst (85% H)3PO40.50g), heated to 50 ℃, and then 70 percent by mass of trimethylolpropane-tris (3-aziridinyl propionate) ethanol solution (35.42g, which contains 21.25g of trimethylolpropane-tris (3-aziridinyl propionate) and 0.05mol) is added dropwise for 40 min. After the dropwise addition, the temperature is raised to 60 ℃ for reaction for 7 hours.
(2) Using K as the reaction solution2CO3Adjusting to be alkalescent (pH is 9-10), dropwise adding 80% benzyl chloride ethanol solution (47.48g, wherein 37.98g of benzyl chloride is contained, 0.30mol) under the protection of nitrogen, and reacting at 60 ℃ for 12 h; removing insoluble substances after the reaction is finished, concentrating the reaction solution, purifying and separating the product by using a toluene column chromatography, and drying in vacuum until the weight is constant to obtain the product.
Evaluation of Performance
According to the oil and gas standard SY/T5329-2012 'water quality index and analysis method for clastic rock oil reservoir water injection', a secondary repetition method is adopted to test the sterilization effect of the sample of the embodiment on the oily sewage. The liquid in the test bottle turns black or has black precipitate, namely Sulfate Reducing Bacteria (SRB) is present; the liquid in the test bottle turns yellow or turbid from red, which indicates that the liquid contains saprophytic bacteria (TGB). The bactericidal effects of the samples of examples 3 and 5 are shown in tables 3 and 4.
Table 3 evaluation results of bactericidal effect of sample of example 3
Figure GDA0002418200880000111
Table 4 evaluation results of bactericidal effect of sample of example 5
Figure GDA0002418200880000112
Tables 3 and 4 show that the samples of examples 3 and 5 have good bactericidal effects against Sulfate Reducing Bacteria (SRB) and saprophytic bacteria (TGB) in oily sewage.
The foregoing is a more detailed description of the invention and it is not intended that the invention be limited to the specific embodiments described herein, but that various modifications, alterations, and substitutions may be made by those skilled in the art without departing from the spirit of the invention, which should be construed to fall within the scope of the invention as defined by the appended claims.

Claims (7)

1. The application of the star-shaped multi-cation-based compound as a bactericide is characterized in that the compound is applied to the bacterial treatment for controlling the oily sewage of the oil field, and the structural formula of the compound is as follows:
Figure FDA0002418200870000011
wherein R is2-is-H or
Figure FDA0002418200870000012
R1is-CH3or-CH2CH3(ii) a Or R1-is C12～C18Alkyl group of (1).
2. The application of the star-shaped multi-cation-based compound as a bactericide according to claim 1, wherein the addition concentration of the compound as the bactericide is 10-50 mg/L.
3. The application of the star-shaped multi-cation-based compound as a bactericide according to claim 1, wherein the preparation method of the star-shaped multi-cation-based compound comprises the following steps:
adding trimethylolpropane-tris (3-aziridinyl propionate) reaction liquid into methylamine or ethylamine aqueous solution or long-chain fatty primary amine ethanol solution and an acid catalyst to perform aziridine ring-opening reaction, and reacting at 40-70 ℃ for 5-7 h;
under the alkalescent condition, adding methyl chloride or benzyl chloride reaction liquid into the reactant for quaternization, and reacting for 10-16 h at 50-70 ℃ under the protection of nitrogen; removing insoluble substances after the reaction is finished, concentrating the reaction solution, purifying and separating the product by using a toluene column chromatography, and drying in vacuum until the weight is constant to obtain the product.
4. The use of a star-shaped polycationic compound as claimed in claim 3, wherein the molar ratio of trimethylolpropane-tris (3-aziridinyl propionate) to methylamine or ethylamine in the aziridine ring-opening reaction is 1: 3.
5. The application of the star-shaped multi-cation-based compound as a bactericide according to claim 3, characterized in that: in the aziridine ring-opening reaction, the acidic catalyst is a phosphoric acid aqueous solution with the mass fraction of 85 percent, and the dosage of the acidic catalyst is 1 percent of the total mass of the raw materials.
6. The application of the star-shaped multi-cation-based compound as a bactericide in claim 3, wherein in the quaternization reaction, the pH value is 9-10 under weak alkaline condition, and K is used as a reaction solution2CO3And adjusting to alkalescence.
7. The use of a star-shaped polycationic compound as claimed in claim 3, wherein the amount of methyl chloride or benzyl chloride in the quaternization reaction is 6 times that of trimethylolpropane-tris (3-aziridinyl propionate).
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