CN108541707A - A kind of application of star-like polycation based compound as fungicide - Google Patents
A kind of application of star-like polycation based compound as fungicide Download PDFInfo
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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
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- 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
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Abstract
A kind of application the invention discloses star-like polycation based compound as fungicide, a kind of high performance star-like multi-quaternary ammonium salt series bactericidal agent of synthesis.The fungicide can effectively inhibit clay hydration swelling and dispersion migration under extremely low dosage.This cationic germicide with intensive charge can act on electronegative clay particle by multiple spot, degree of absorption is high, to realize the purpose of low dosage, high anti-dilative simultaneously due to containing 18 quaternary ammonium salt groups in molecule.This cationic germicide with intensive charge can be widely applied in oil-contaminated water of oil field processing.
Description
Technical field
The present invention relates to multi-quaternary ammonium salt cationic surfactant preparing technical field, more particularly to a kind of star-like more sun from
Application of the subbase compound as fungicide.
Background technology
Often contain a large amount of bacterium, such as sulfate reducing bacteria, iron bacteria, saprophytic bacteria in oil field flood pattern, these are thin
Bacterium universally present in the environment such as the mud of anaerobism, the deposit of fresh water, salt water and seawater habitat, metal delivery tubes road, it
Corrodible metal equipment, cause circulation stick mud increase, block pipeline, influence heat exchange efficiency, deteriorate water quality, reduce water
The treatment effect for the treatment of agent brings many inconvenience to production.Currently, the method that oil field is used to control bacterium mainly launches season
Ammonium salt series bactericidal agent, such as dodecyl benzyl dimethyl ammonium chloride (1227), dodecyl trimethyl ammonium chloride (1231), season
The bactericidal mechanism of ammonium salt is mainly the plasmalemma for compromising control cell permeability, to kill bacterium.But this kind of sterilization
In oil field flood pattern, there are many shortcomings for agent, are mainly presented with that medicament effective duration is short, microorganism is easy to it
Develop immunity to drugs, dosage is big, costly, and use when foam it is more, not easy-clear the shortcomings of.Therefore, one kind is researched and produced
Novel stabilization, adaptable oil field fungicide are one particularly significant and have reality instead of existing quaternary ammonium salt fungicide
The research topic of meaning.
Invention content
A kind of application it is an object of the invention to provide star-like polycation based compound as fungicide, passes through synthesis
A kind of cationic germicide with intensive charge, is applied in oil-gas mining.
In order to achieve the above objectives, the present invention uses following technical scheme：
A kind of application of star-like polycation based compound as fungicide, structural formula are：
Wherein, R1- is alkyl；R2For-H or
Preferably, R1- is-CH3Or-CH2CH3。
Preferably, R1It is C12~C18Alkyl.
A concentration of 10~50mg/L is added in application of the star-like polycation based compound as fungicide.
The preparation method of the star-like polycation based compound, includes the following steps：
To the three hydroxyl first of middle addition of methylamine or ethylamine solution or long-chain fat primary amine ethanol solution and acidic catalyst
Base propane-three (3- aziridinyls propionic ester) reaction solution carries out aziridine ring-opening reaction, and 5~7h is reacted at 40~70 DEG C；
Under weak basic condition, chloromethanes is added into above-mentioned reactant or the progress of benzyl chloride reaction solution liquid is quaternary ammoniated anti-
It answers, under nitrogen protection, 50~70 DEG C of 10~16h of reaction；Insoluble matter is removed after reaction, and concentration of reaction solution uses toluene
Column chromatography is isolated and purified with product, is dried under vacuum to constant weight and just obtains product.
In aziridine ring-opening reaction, trimethylolpropane-three (3- aziridinyls propionic ester) and methylamine or ethamine mole
Than being 1:3.
In aziridine ring-opening reaction, the acidic catalyst is the phosphate aqueous solution that mass fraction is 85%, is used
Amount is the 1% of raw material gross mass.
In quaternary ammonium reaction, weak basic condition pH=9~10, reaction solution K2CO3It is adjusted to alkalescent.
In quaternary ammonium reaction, the amount of the substance of chloromethanes or benzyl chloride is (the 3- aziridinyls third of trimethylolpropane-three
Acid esters) 6 times.
The present invention compared with the prior art, has the following advantages：
The present invention redesigns quaternary ammonium salt biocide molecules structure, synthesizes a kind of star-like sterilization of polycation base
Agent.There is such star-like fungicide of polycation base stronger bactericidal activity to pass through due to there is multiple quaternary ammonium salt groups in molecule
Inducing action makes the positive charge density in molecule on nitrogen-atoms increase, and is conducive to absorption of the biocide molecules in bacterium surface, to
The permeability for changing cell wall, makes thalline rupture；In addition, after fungicide is adsorbed onto phage surface, there are three long for tool in molecule
The hydrophobic grouping of chain is conducive to hydrophobic group and gos deep into the class lipid layer and albumin layer of somatic cells respectively with hydrophilic group, enzyme is caused to lose
Activity and protein denaturation, due to the joint effect of both effects so that this cationic germicide with intensive charge
There is stronger sterilizing ability.The series bactericidal agent is expected to replace existing quaternary ammonium salt fungicide and oxidative bactericide, and
Huge effect will be played in oil field flood pattern sterilization process.
This star-like fungicide has stronger sterilizing ability.Since microbial cell surface is negatively charged, and cell membrane
The phosphatide inside contained and the hydrolysis of some memebrane proteins are also negatively charged, therefore the present invention has devised a kind of quaternary ammonium salt group containing there are six
Star-like fungicide, increases positive charge density, is conducive to absorption of the biocide molecules in bacterium surface, to change cell wall
Permeability makes thalline rupture, to improve bactericidal effect.
Due to containing multiple quaternary ammonium salt groups in molecule, the positive charge density in molecule on nitrogen-atoms is made by inducing action
Increase, be conducive to biocide molecules makes thalline rupture in the absorption of bacterium surface to change the permeability of cell wall；In addition, working as
After fungicide is adsorbed onto phage surface, there are three the hydrophobic groupings of long-chain for tool in molecule, are conducive to hydrophobic group and distinguish with hydrophilic group
The class lipid layer and albumin layer for going deep into somatic cells cause enzyme to lose activity and protein denaturation, due to the joint of both effects
Effect so that this cationic germicide with intensive charge has stronger sterilizing ability.It is existing that the series bactericidal agent is expected to substitution
Some quaternary ammonium salt fungicide and oxidative bactericide, and huge work will be played in oil field flood pattern sterilization process
With.
Specific implementation mode
The present invention adopts the following technical scheme that：
Wherein, R1- is-CH3Or-CH2CH3Or R1It is-CH3Or-CH2CH3；R2For-H or
According to above-mentioned reaction mechanism, the present invention adopts the following technical scheme that
A kind of star-like multi-quaternary ammonium salt series bactericidal agent, the structural formula of the fungicide are：
Wherein, R1- is-CH3Or-CH2CH3Or R1It is-CH3Or-CH2CH3；R2For-H or
The method for preparing a kind of above-mentioned star-like multi-quaternary ammonium salt series bactericidal agent, steps of the method are：
In methylamine (or ethamine) aqueous solution for being 20~70% equipped with mass fraction or long-chain fat primary amine ethyl alcohol is housed
Trimethylolpropane-three (3- aziridinyls propionic ester) reaction solution is added dropwise in the reaction bulb of solution and acidic catalyst and carries out nitrogen third
Pyridine ring-opening reaction, wherein hydroxymethyl-propane-three (3- aziridinyls propionic ester) and the molar ratio of methylamine (or ethamine) are 1:3,
40~70 DEG C of 5~7h of reaction；Again by above-mentioned reaction solution K2CO3It is adjusted to alkalescent (pH=9~10), chloromethanes (or chlorination is added
Benzyl) reaction solution progress second step quaternary ammonium reaction, the amount of the wherein substance of chloromethanes (or benzyl chloride) is trimethylolpropane-three
6 times of (3- aziridinyls propionic ester), under nitrogen protection, 50~70 DEG C of 10~16h of reaction.Insoluble matter is removed after reaction
Matter, concentration of reaction solution are isolated and purified with product with toluene column chromatography, are dried under vacuum to constant weight and just obtain product.
Embodiment 1
(1) equipped with mass fraction be 20% methylamine water solution (23.25g, wherein 4.65g containing methylamine, 0.15mol) and
Acidic catalyst (85%H3PO4, 0.30g), 40 DEG C are warming up to, (the 3- of trimethylolpropane-three that mass fraction is 70% is added dropwise
Aziridinyl propionic ester) aqueous solution (35.42g, wherein contain trimethylolpropane-three (3- aziridinyls propionic ester) 21.25g,
0.05mol), time for adding 40min.After being added dropwise, it is warming up to 70 DEG C of reaction 5h.
(2) by above-mentioned reaction solution K2CO3It is adjusted to alkalescent (pH=9~10), under nitrogen protection, mass fraction is added dropwise
For 60% chloromethanes ethanol solution (25.25g, wherein 15.15g containing chloromethanes, 0.30mol), 10h is reacted at 50 DEG C；Reaction
After remove insoluble matter, concentration of reaction solution is isolated and purified with product with toluene column chromatography, and being dried under vacuum to constant weight must produce
Object.
The structural formula of 1 products therefrom of embodiment is：
1H NMR (300MHz, DMSO)：δ 3.91 (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)：δ 173.5,66.1,54.1~56.8,49.5,35.7,27.3,23.0,7.9~
8.3ppm。
Embodiment 2
(1) equipped with mass fraction be 70% ethylamine solution (9.54g, wherein 6.75g containing ethamine, 0.15mol) and
Acidic catalyst (85%H3PO4, 0.30g), 50 DEG C are warming up to, (the 3- of trimethylolpropane-three that mass fraction is 70% is added dropwise
Aziridinyl propionic ester) aqueous solution (35.42g, wherein contain trimethylolpropane-three (3- aziridinyls propionic ester) 21.25g,
0.05mol), time for adding 40min.After being added dropwise, it is warming up to 70 DEG C of reaction 7h.
(2) by above-mentioned reaction solution K2CO3It is adjusted to alkalescent (pH=9~10), under nitrogen protection, mass fraction is added dropwise
For 80% benzyl chloride ethanol solution (47.48g, wherein chloride containing benzyl 37.98g, 0.30mol), 16h is reacted at 70 DEG C；Reaction
After remove insoluble matter, concentration of reaction solution is isolated and purified with product with toluene column chromatography, is dried under vacuum to constant weight just
Product.
The structural formula of 2 products therefrom of embodiment is：
1H NMR (300MHz, DMSO)：δ 7.16~7.25 (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)：δ 173.1,125.3~131.6,65.9,60.4,54.2~56.6,35.7,
27.3,23.0,7.7~8.3ppm.
Performance evaluation
According to People's Republic of China (PRC) petroleum gas standard SY/T5329-2012《Clastic rock reservoir water water quality index
And analysis method》, using secondary iterative method testing example sample to the bactericidal effect of oily wastewater.Liquid blackening in test bottle
Or have black precipitate, that is, indicate sulfate reducing bacteria (SRB)；Liquid is contained by red flavescence or muddy i.e. expression in test bottle
Saprophytic bacteria (TGB).The sample bactericidal effect of Examples 1 and 2 is as shown in Table 1 and Table 2.
The sample Evaluation of Germicidal Efficacy result of 1 embodiment 1 of table
The sample Evaluation of Germicidal Efficacy result of 2 embodiment 2 of table
Tables 1 and 2 shows that the sample of Examples 1 and 2 is to sulfate reducing bacteria (SRB) in bactericidal effect such as oily wastewater
There is good bactericidal effect with saprophytic bacteria (TGB).
Embodiment 3
(1) in the dodecyl primary amine ethanol solution (34.69g, wherein containing dodecyl primary for being 80% equipped with mass fraction
Amine 27.75g, 0.15mol) and acidic catalyst (85%H3PO4, 0.50g), 50 DEG C are warming up to, it is 70% that mass fraction, which is added dropwise,
Trimethylolpropane-three (3- aziridinyls propionic ester) ethanol solution (35.42g, wherein (the 3- a word used for translations third containing trimethylolpropane-three
Piperidinyl propionic ester) 21.25g, 0.05mol), time for adding 40min.After being added dropwise, it is warming up to 70 DEG C of reaction 6h.
(2) by above-mentioned reaction solution K2CO3It is adjusted to alkalescent (pH=9~10), under nitrogen protection, mass fraction is added dropwise
For 60% chloromethanes ethanol solution (25.25g, wherein 15.15g containing chloromethanes, 0.30mol), 10h is reacted at 50 DEG C；Reaction
After remove insoluble matter, concentration of reaction solution is isolated and purified with product with toluene column chromatography, and being dried under vacuum to constant weight must produce
Object.
The structural formula of 3 products therefrom of embodiment is：
1H NMR (300MHz, DMSO)：δ 3.94 (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)：δ 173.1,65.9,64.4,61.8,58.8~59.1,52.0~52.3,35.7,
31.9,29.3~29.6,26.8,25.4,22.7,14.1,7.3ppm.
Embodiment 4
(1) in the octadecyl primary amine ethanol solution (50.53g, wherein containing octadecyl primary for being 80% equipped with mass fraction
Amine 40.43g, 0.15mol) and acidic catalyst (85%H3PO4, 0.60g), 50 DEG C are warming up to, it is 70% that mass fraction, which is added dropwise,
Trimethylolpropane-three (3- aziridinyls propionic ester) ethanol solution (35.42g, wherein (the 3- a word used for translations third containing trimethylolpropane-three
Piperidinyl propionic ester) 21.25g, 0.05mol), time for adding 40min.After being added dropwise, it is warming up to 50 DEG C of reaction 8h.
(2) by above-mentioned reaction solution K2CO3It is adjusted to alkalescent (pH=9~10), under nitrogen protection, mass fraction is added dropwise
For 80% benzyl chloride ethanol solution (47.48g, wherein chloride containing benzyl 37.98g, 0.30mol), 16h is reacted at 70 DEG C；Reaction
After remove insoluble matter, concentration of reaction solution is isolated and purified with product with toluene column chromatography, is dried under vacuum to constant weight just
Product.
The structural formula of 4 products therefrom of embodiment is：
1H NMR (300MHz, DMSO)：δ 7.16~7.25 (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)：δ 173.1,125.7~131.6,65.9,60.8~54.6,35.7,22.7~
31.9,14.1,7.1ppm.
Embodiment 5
(3) in the myristyl primary amine ethanol solution (40.03g, wherein containing myristyl primary for being 80% equipped with mass fraction
Amine 32.03g, 0.15mol) and acidic catalyst (85%H3PO4, 0.50g), 50 DEG C are warming up to, it is 70% that mass fraction, which is added dropwise,
Trimethylolpropane-three (3- aziridinyls propionic ester) ethanol solution (35.42g, wherein (the 3- a word used for translations third containing trimethylolpropane-three
Piperidinyl propionic ester) 21.25g, 0.05mol), time for adding 40min.After being added dropwise, it is warming up to 60 DEG C of reaction 7h.
(4) by above-mentioned reaction solution K2CO3It is adjusted to alkalescent (pH=9~10), under nitrogen protection, mass fraction is added dropwise
For 80% benzyl chloride ethanol solution (47.48g, wherein chloride containing benzyl 37.98g, 0.30mol), 12h is reacted at 60 DEG C；Reaction
After remove insoluble matter, concentration of reaction solution is isolated and purified with product with toluene column chromatography, is dried under vacuum to constant weight just
Product.
Embodiment 6
(1) in the cetyl primary amine ethanol solution (45.29g, wherein containing cetyl primary for being 80% equipped with mass fraction
Amine 36.23g, 0.15mol) and acidic catalyst (85%H3PO4, 0.50g), 50 DEG C are warming up to, it is 70% that mass fraction, which is added dropwise,
Trimethylolpropane-three (3- aziridinyls propionic ester) ethanol solution (35.42g, wherein (the 3- a word used for translations third containing trimethylolpropane-three
Piperidinyl propionic ester) 21.25g, 0.05mol), time for adding 40min.After being added dropwise, it is warming up to 60 DEG C of reaction 7h.
(2) by above-mentioned reaction solution K2CO3It is adjusted to alkalescent (pH=9~10), under nitrogen protection, mass fraction is added dropwise
For 80% benzyl chloride ethanol solution (47.48g, wherein chloride containing benzyl 37.98g, 0.30mol), 12h is reacted at 60 DEG C；Reaction
After remove insoluble matter, concentration of reaction solution is isolated and purified with product with toluene column chromatography, is dried under vacuum to constant weight just
Product.
Performance evaluation
According to People's Republic of China (PRC) petroleum gas standard SY/T5329-2012《Clastic rock reservoir water water quality index
And analysis method》, using secondary iterative method testing example sample to the bactericidal effect of oily wastewater.Liquid blackening in test bottle
Or have black precipitate, that is, indicate sulfate reducing bacteria (SRB)；Liquid is contained by red flavescence or muddy i.e. expression in test bottle
Saprophytic bacteria (TGB).The sample bactericidal effect of embodiment 1 and 3 is as shown in Table 3 and Table 4.
The sample Evaluation of Germicidal Efficacy result of 3 embodiment 3 of table
The sample Evaluation of Germicidal Efficacy result of 4 embodiment 5 of table
Table 3 and table 4 show that the sample of embodiment 3 and 5 is to sulfate reducing bacteria in oily wastewater (SRB) and saprophytic bacteria
(TGB) there is good bactericidal effect.
The above content is it is made for the present invention be further described, and it cannot be said that the present invention specific implementation mode only
It is limited to this, for those of ordinary skill in the art to which the present invention belongs, without departing from the inventive concept of the premise, also
Several simple deduction or replace can be made, the present invention is all shall be regarded as belonging to and determines protection by the claims submitted
Range.
Claims (9)
1. a kind of application of star-like polycation based compound as fungicide, which is characterized in that be applied to control oil field oil-containing
In sewage bacterial processing, which is：
Wherein, R1- is alkyl；R2For-H or
2. a kind of application of the star-like polycation based compound according to claim 1 as fungicide, which is characterized in that
Wherein, R1- is-CH3Or-CH2CH3。
3. a kind of application of the star-like polycation based compound according to claim 1 as fungicide, which is characterized in that
Wherein, R1It is C12~C18Alkyl.
4. a kind of application of the star-like polycation based compound according to claim 1 as fungicide, which is characterized in that
A concentration of 10~50mg/L of addition as fungicide.
5. a kind of application of the star-like polycation based compound according to claim 1 as fungicide, described is star-like
The preparation method of polycation based compound, includes the following steps：
To methylamine or ethylamine solution or the middle addition trihydroxy methyl third of long-chain fat primary amine ethanol solution and acidic catalyst
Alkane-three (3- aziridinyls propionic ester) reaction solution carries out aziridine ring-opening reaction, and 5~7h is reacted at 40~70 DEG C；
Under weak basic condition, chloromethanes is added into above-mentioned reactant or benzyl chloride reaction solution liquid carries out quaternary ammonium reaction,
Under nitrogen protection, 50~70 DEG C of 10~16h of reaction；Insoluble matter, concentration of reaction solution, with toluene column chromatography are removed after reaction
Method is isolated and purified with product, is dried under vacuum to constant weight and just obtains product.
6. a kind of application of the star-like polycation based compound according to claim 5 as fungicide, which is characterized in that
In aziridine ring-opening reaction, trimethylolpropane-three (3- aziridinyls propionic ester) and methylamine or ethamine molar ratio are 1:3.
7. a kind of application of the star-like polycation based compound according to claim 5 as fungicide, it is characterised in that：
In aziridine ring-opening reaction, the acidic catalyst is the phosphate aqueous solution that mass fraction is 85%, and dosage is raw material
The 1% of gross mass.
8. a kind of application of the star-like polycation based compound according to claim 5 as fungicide, which is characterized in that
In quaternary ammonium reaction, weak basic condition pH=9~10, reaction solution K2CO3It is adjusted to alkalescent.
9. a kind of application of the star-like polycation based compound according to claim 5 as fungicide, which is characterized in that
In quaternary ammonium reaction, the amount of the substance of chloromethanes or benzyl chloride is the 6 of trimethylolpropane-three (3- aziridinyls propionic ester)
Times.
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