CN117603083A - Preparation and application of four-head bola type efficient bactericide - Google Patents
Preparation and application of four-head bola type efficient bactericide Download PDFInfo
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- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 38
- 239000003899 bactericide agent Substances 0.000 title abstract description 31
- 240000007839 Kleinhovia hospita Species 0.000 title abstract description 23
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 238000004659 sterilization and disinfection Methods 0.000 claims abstract description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000002455 scale inhibitor Substances 0.000 claims abstract description 16
- 125000000129 anionic group Chemical group 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 22
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 claims description 19
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 230000002401 inhibitory effect Effects 0.000 claims description 17
- 230000000149 penetrating effect Effects 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000000498 cooling water Substances 0.000 claims description 7
- 235000012206 bottled water Nutrition 0.000 claims description 3
- 239000003651 drinking water Substances 0.000 claims description 3
- 239000008235 industrial water Substances 0.000 claims description 3
- 239000002357 osmotic agent Substances 0.000 claims 2
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- 230000001954 sterilising effect Effects 0.000 abstract description 51
- 230000005764 inhibitory process Effects 0.000 abstract description 21
- 241000195493 Cryptophyta Species 0.000 abstract description 20
- 238000000034 method Methods 0.000 abstract description 12
- 230000008569 process Effects 0.000 abstract description 6
- 239000002518 antifoaming agent Substances 0.000 abstract description 4
- 125000003368 amide group Chemical group 0.000 abstract description 2
- 125000001165 hydrophobic group Chemical group 0.000 abstract description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 25
- 239000007864 aqueous solution Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 241000894006 Bacteria Species 0.000 description 17
- 239000002131 composite material Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
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- 239000006260 foam Substances 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 229940125904 compound 1 Drugs 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 229940125782 compound 2 Drugs 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- NNZGNZHUGJAKKT-UHFFFAOYSA-M 3-bromopropyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCBr NNZGNZHUGJAKKT-UHFFFAOYSA-M 0.000 description 5
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
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- 229940105325 3-dimethylaminopropylamine Drugs 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229960000686 benzalkonium chloride Drugs 0.000 description 4
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 4
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 239000003139 biocide Substances 0.000 description 3
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- 230000003068 static effect Effects 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 206010059866 Drug resistance Diseases 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
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- 229910021642 ultra pure water Inorganic materials 0.000 description 2
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- VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical class OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DBAKFASWICGISY-BTJKTKAUSA-N Chlorpheniramine maleate Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 DBAKFASWICGISY-BTJKTKAUSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
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- 239000000203 mixture Substances 0.000 description 1
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- 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
- A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/20—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
- C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
- C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
- C02F5/12—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/36—Acyl halides
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- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
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Abstract
The invention discloses preparation and application of a four-head bola type efficient bactericide, and belongs to the field of water treatment science. The solubility of the four-head bola type high-efficiency bactericide in water at normal temperature is up to 1000mmol/L, and the bactericide contains amide groups, is easy to degrade and is environment-friendly. When the concentration of the four-head bola type high-efficiency bactericide is more than 150mg/L, the sterilization rate can reach more than 99.6 percent; when the concentration is more than 200mg/L, the algae removal rate can reach 99.8% after three days. The hydrophobic groups of the bactericide are positioned between the ion head groups, so that the foamability of the bactericide is extremely poor, and a defoaming agent is not required to be added in the use process, so that the running cost of the system is reduced. Meanwhile, the four-head bola type bactericide and the common anionic scale inhibitor have good compatibility, and the solution is clear and transparent after the four-head bola type bactericide and the common anionic scale inhibitor are mixed, so that the system still has excellent scale inhibition performance.
Description
Technical Field
The invention relates to preparation and application of a four-head bola type efficient bactericide, and belongs to the field of water treatment science.
Background
With the rapid rise of global economy and industrialization level, water resource shortage becomes a global problem. In many industrial processes, such as thermal power generation and pulping and papermaking, the demand for large amounts of water resources further exacerbates the pressure of water shortages. One of the key ways to solve this problem is to implement recycling of water resources. In industrial production, a circulating cooling water system is widely adopted to achieve the aims of high-efficiency water use and water saving. In an open circulating cooling water system which operates for a long time, microorganisms in the system are greatly propagated along with invasion of microorganisms in the air, so that water quality is deteriorated; meanwhile, as the concentration multiple increases, scaling phenomena are generated on the inner wall of the system and the pipeline. These factors can cause corrosion of equipment, reduce heat transfer efficiency, and thus affect the proper operation of the system. Therefore, the selection of appropriate chemicals to inhibit microbial growth and intra-system scaling is an important guarantee to ensure efficient use of water resources.
In the circulating cooling water system, common microorganisms mainly include bacteria, fungi, algae and the like. According to the mechanism of sterilization, commonly used bactericides are classified into oxidizing bactericides (such as chlorine, active bromine, chlorphenamine, etc.) and non-oxidizing bactericides (such as chlorophenols, quaternary ammonium salts, etc.). The oxidation type bactericide has better bactericidal effect, but generally has the problems of larger toxicity, secondary pollution to water body and the like. With the enhancement of environmental awareness, people gradually throw eyes towards quaternary ammonium salt surfactants with smaller toxicity, and JielMIE and XinelMIE are two of the most common.
However, in the practical use process, the quaternary ammonium salt surfactant also has a certain problem. First, aqueous solutions in which surfactants are dissolved generate a large amount of foam during the flow. In order to ensure that the circulating water system normally operates, a defoaming agent is usually added, so that the cost is increased; secondly, since the hydrophilic head group of the quaternary ammonium surfactant has positive charges, when mixed with some anionic scale inhibitors such as sodium polyacrylate and the like, the quaternary ammonium surfactant is easy to be strongly combined with anions to form organic matter sediment through electrostatic attraction, and the sterilization and scale inhibition effects are weakened. The prior art CN116395865A discloses an environment-friendly phosphorus-free quaternary ammonium salt scale inhibitor and application thereof, and discloses a compound with a tetrameric quaternary ammonium salt structure, which has high solubility and good scale inhibition performance, but has poor sterilization performance and is not easy to degrade, and meanwhile, the technology does not solve the problem of foaming of a surfactant in the flowing process.
The non-foaming characteristic of the sterilizing scale inhibitor reduces the foaming problem in the system, not only is beneficial to the normal operation of a water circulation system, but also reduces the cost of adding the defoaming agent. On the basis, the characteristic of easy degradation ensures that the bactericide is easier to be naturally degraded after being used, reduces the influence on the environment and accords with the concept of sustainable development. Together, the advantages provide a feasible solution for the novel bactericide in the aspects of improving the water resource utilization efficiency, reducing the cost, relieving the environmental burden and the like. Therefore, the novel quaternary ammonium salt bactericide which has high sterilization efficiency, good scale inhibition, high solubility, poor foamability and easy degradation is developed, and has important significance for prolonging the service life of a circulating water system and saving water resources.
Disclosure of Invention
Technical problems:
the quaternary ammonium salt bactericide is adsorbed and destroyed by utilizing the characteristic that the surface of bacteria is negatively charged, so that the drug resistance is not easy to generate. However, in the practical use process, the aqueous solution of the quaternary ammonium salt surfactant is easy to generate a large amount of foam in the flowing process, and when the aqueous solution of the quaternary ammonium salt surfactant is mixed with some anionic scale inhibitors, precipitation is easy to form, so that the sterilization and scale inhibition effects are weakened. Therefore, how to design and synthesize a bactericide with high sterilization efficiency, poor foamability, good compatibility and high solubility is a technical problem facing the field.
The technical scheme is as follows: in order to achieve the above purpose, the invention adopts the following technical scheme:
the first object of the invention is to provide a compound (four-headed bola type high-efficiency bactericide), which has the following structural formula:
in one embodiment, the four-headed bola type high-efficiency bactericide is synthesized by the following route:
in one embodiment, the synthesis step of the four-headed bola type high-efficiency bactericide (N2-C12-N2) comprises the following steps:
(1) Reacting tetradecanedioic acid with thionyl chloride to obtain a compound 1;
(2) Reacting compound 1 with 3-dimethylaminopropylamine;
(3) The compound 2 and 3-bromo-propyl trimethyl ammonium bromide obtain the target product N2-C12-N2.
In one embodiment, the four-headed bola type high-efficiency bactericide (N2-C12-N2) is prepared by the following method:
(1) Mixing tetradecanedioic acid with DMF, adding thionyl chloride until the system is clear, and distilling to obtain a compound 1;
(2) Mixing triethylamine with 3-dimethylaminopropylamine, adding a compound 1, adding dichloromethane and acetone for recrystallization, and drying to obtain a compound 2;
(3) And mixing the compound 2 with 3-bromo-propyl trimethyl ammonium bromide and ethanol for reaction to obtain the four-headed bola type efficient bactericide.
In one embodiment, the four-headed bola type high-efficiency bactericide (N2-C12-N2) is prepared by the following method:
(1) The tetradecanedioic acid is placed in a three-neck flask, a few drops of 50 mu LDMF are dripped into the three-neck flask, thionyl chloride is slowly dripped into the three-neck flask at the temperature of 60 ℃, and the generated acid gas is absorbed by adopting sodium hydroxide aqueous solution and reacts until the system is clear liquid. After the reaction is finished, removing excessive thionyl chloride by reduced pressure distillation to obtain a pure product of the compound 1;
(2) Triethylamine and 3-dimethylaminopropylamine were placed in a three-necked flask, and Compound 1 was slowly dropped in an ice bath, and reacted at room temperature of 25℃for 6 hours after the dropping was completed. After the reaction is finished, adding dichloromethane for extraction, adjusting the pH to be strong alkaline by using NaOH aqueous solution, adding acetone for recrystallization, and drying to obtain a pure product of the compound 2;
(3) Synthesis of N2-C12-N2: the compound 2, 3-bromo-propyl trimethyl ammonium bromide and ethanol are placed in a single-neck flask to react for 48 to 72 hours at 92 ℃. Cooling to room temperature, distilling under reduced pressure to remove solvent, recrystallizing with ethanol and acetone for 3 times, and drying to obtain N2-C12-N2 pure product.
In one embodiment, the compound has a solubility of up to 1000mmol/L.
A second object of the present invention is to provide a bactericidal scale-inhibiting penetrant comprising any of the compounds described above and an anionic scale inhibitor.
In one embodiment, the concentration of the compound is 100 to 300ppm (ppm is equivalent to mg/L).
In one embodiment, the anionic scale inhibitor sodium polyacrylate concentration is 200ppm.
In one embodiment, the ratio of the compound to the anionic scale inhibitor ranges from 1:2 to 3:2.
The invention also provides the application of any one of the compounds or any one of the sterilization scale inhibition penetrants in water treatment.
In one embodiment, the applications include, but are not limited to, industrial water treatment, cooling water systems, potable water disinfection.
The beneficial effects are that:
the invention takes tetradecanedioic acid as a raw material to synthesize a four-headed bola compound. The method has the following specific beneficial effects:
(1) The solubility of the four-head bola type compound in water at normal temperature is up to 1000mmol/L, and the application field of the four-head bola type compound is widened due to the high solubility.
(2) The quaternary ammonium salt head group of the four-head bola type has concentrated charge, can be strongly combined with the surface of bacteria and algae, has high-efficiency sterilization and algae removal performance, and can achieve the sterilization rate of more than 99.6 percent when the concentration is more than 150 mg/L; when the concentration is more than 200mg/L, the algae removal rate can reach 99.8% in three days, and the bactericide is adsorbed on the surface of bacteria through strong electrostatic action, so that the bacteria are not easy to generate drug resistance.
(3) The hydrophobic groups of the four-head bola type quaternary ammonium salt are positioned between the ion head groups, so that the surface activity of the quaternary ammonium salt is greatly weakened while the sterilization and algae removal capacity of the quaternary ammonium salt is not influenced, the foamability of the quaternary ammonium salt is extremely poor, and a defoaming agent is not required to be added in the use process, so that the running cost of the system is reduced. The quaternary ammonium salt with four bola contains amide groups, so that the quaternary ammonium salt is easy to degrade and is environment-friendly.
(4) The four-head bola type efficient bactericide and the common anionic scale inhibitor sodium polyacrylate have good compatibility, the solution is still clear and transparent after the four-head bola type efficient bactericide and the common anionic scale inhibitor sodium polyacrylate are mixed, and the system still has excellent scale inhibition performance.
Drawings
FIG. 1 shows the molecular structure of N2-C12-N2.
FIG. 2 shows a hydrogen nuclear magnetic resonance spectrum of N2-C12-N2.
FIG. 3 is a graph of the surface tension of an aqueous N2-C12-N2 solution as a function of concentration (25 ℃ C.).
FIG. 4 is a photograph of the foam appearance of 100mmol/L of an aqueous solution of N2-C12-N2 and cetyltrimethylammonium bromide (CTAB) at equal concentrations.
FIG. 5 is a photograph showing the appearance of an aqueous solution after mixing N2-C12-N2 at various concentrations with 200ppm sodium polyacrylate and standing for 7 days.
FIG. 6 shows CaCl at equimolar concentration (5 mmol/L) 2 With Na and Na 2 CO 3 The appearance photograph of the mixed aqueous solution of N2-C12-N2 with different concentrations and 200ppm sodium polyacrylate is not added/added into the aqueous solution.
FIG. 7 shows CaCl at equimolar concentration (5 mmol/L) 2 With Na and Na 2 CO 3 CaCO formed by mixing water solutions of N2-C12-N2 with different concentrations and 200ppm sodium polyacrylate is not added into the water solution 3 Is a microscopic comparison photograph of (c).
FIG. 8 shows that N2-C12-N2 and the tetrameric quaternary ammonium salt are present in equal concentrations of 50mmol/L with 1000mmol/L CaCl, respectively 2 Photograph of the appearance of the mixed aqueous solution.
FIG. 9 is a photograph showing the appearance of an aqueous solution of various concentrations of benzalkonium chloride mixed with 200ppm sodium polyacrylate after standing for 7 days.
Detailed Description
Example 1 Synthesis of four-headed bola type high-efficiency Bactericide (N2-C12-N2)
1. Synthesis of Compound 1
Tetradecanedioic acid (50 g,0.19 mol) was placed in a 1000mL three-necked flask, a few drops of DMF was added, thionyl chloride (52.95 g,0.45 mol) was slowly added dropwise at 60℃and the acid gas generated was absorbed with aqueous sodium hydroxide solution, reacted until the system was a clear liquid, and no bubbles were generated in the aqueous sodium hydroxide solution. After the reaction, excess thionyl chloride was distilled off under reduced pressure to give compound 1.
2. Synthesis of Compound 2
Triethylamine (113.51 g,1.16 mol) and 3-dimethylaminopropylamine (42.03 g,0.41 mol) were placed in a three-necked flask, and Compound 1 (55.2 g,0.19 mol) was slowly dropped in an ice bath and reacted at room temperature for 6 hours after the dropping was completed. After the reaction, adding a proper amount of 500mL of dichloromethane for extraction, adjusting the pH value to be 10-11 with NaOH aqueous solution, adding acetone for recrystallization, and drying to obtain the compound 2 with the yield of 35%.
3. Synthesis of N2-C12-N2
Compound 2 (6 g,0.01 mol) and 3-bromo-propyltrimethylammonium bromide (6.99 g,0.03 mol) and 200ml ethanol were placed in a single-neck flask and reacted at 92℃for 48 hours. Cooling to room temperature, distilling under reduced pressure to remove the solvent, recrystallizing with ethanol and acetone three times, and drying to obtain white powdery solid N2-C12-N2 with a yield of 52%. The molecular structure is shown in figure 1, and the hydrogen nuclear magnetic resonance spectrum is shown in figure 2.
4. Structure and purity determination of N2-C12-N2
10mg of N2-C12-N2 is weighed and placedIn the nuclear magnetic tube, the deuterated reagent DMSO was used for dissolution. Performing at 25deg.C with advanced III nuclear magnetic resonance apparatus 1 H NMR test. 1 The resonance frequency of H is 400MHz. As can be seen from the hydrogen nuclear magnetic resonance spectrum of N2-C12-N2 in FIG. 2, the chemical shift of each hydrogen accords with the target product, and the spectrum has no impurity peak, which indicates that the product reaches high purity and accords with the requirement of subsequent experiments.
1H NMR(400MHz,DMSO)δ8.06(t,2H,C1-1H,C18-1H),3.30,3.40(m,12H,C27-3H,C28-3H,C29-3H,C30-3H),3.16(s,18H,C39-3H,C40-3H,C41-3H,C42-3H,C43-3H,C44-3H),3.12(s,4H,C23-2H,C14-2H),3.09(s,12H,C21-2H,C31-2H,C33-2H,C25-2H,C35-2H,C37-2H),2.23(q,4H,C32-2H,C36-2H),2.09(t,4H,C3-2H,C14-2H),1.85(q,4H,C20-2H,C24-2H),1.48(q,4H,C4-2H,C13-2H),1.24(s,16H,C5-2H,C6-2H,C7-2H,C8-2H,C9-2H,C10-2H,C11-2H,C12-2H)。
Example 2: N2-C12-N2 Performance test
1. Determination of N2-C12-N2 solubility
The compound N2-C12-N2 prepared in example 1 was taken and its solubility was measured by observation. A certain amount of N2-C12-N2 to 10mL columnar vials are weighed, 5mL of ultrapure water is added, the vials are placed in a dry bath at 65 ℃ and heated to be clear and transparent, then the vials are placed in a constant temperature oven at 25 ℃ and balanced for 48 hours, and the observation phenomenon is taken out. If no solid is precipitated, adding a sample into the solution, and repeating the steps until a very small amount of solid is precipitated at 25 ℃; if solid is precipitated, the solvent is supplemented until the solid is completely dissolved. Thus, the solubility of N2-C12-N2 was obtained.
The solubility of N2-C12-N2 in water at normal temperature is up to 1000mmol/L, and the application field of N2-C12-N2 is greatly widened.
2. Determination of the surface tension of an aqueous N2-C12-N2 solution (25 ℃ C.)
Before testing, N2-C12-N2 prepared in example 1 is taken, N2-C12-N2 solution with serial concentration is prepared and placed in an incubator at 25 ℃ for balancing for 12 hours. The specific test method comprises the following steps of firstly pouring into a weighing dishTo this, 16mL of ultrapure water was added to calibrate the ring parameters. A kind of electronic deviceAnd then adding a series of N2-C12-N2 solutions in sequence to enable the concentration of the solutions in the weighing dish to reach a measured value, and measuring the surface tension of the solution after balancing for 10min by adopting a Du No lifting ring method. The test temperature is 25+/-0.1 ℃, the average value is obtained by three times of measurement, and the error is ensured to be 0.1 mN.m -1 Within the inner part.
FIG. 3 is a graph showing the change in surface tension of an aqueous N2-C12-N2 solution with concentration. As can be seen from the figure, the CMC of N2-C12-N2 is as high as 48.5mmol/L, gamma CMC Up to 50.6 mN.m -1 Poor surface activity and is unfavorable for foam formation.
3. Foam Performance test of 100mmol/L aqueous N2-C12-N2 solution
5mL of the N2-C12-N2 aqueous solution prepared in example 1 was added to a 50mL stoppered cylinder at a concentration of 100 mmol/L. Foam was observed after shaking up and down with force 25 times at 25 ℃.
FIG. 4 is a photograph of the foam appearance of 100mmol/L of an aqueous solution of N2-C12-N2 and cetyltrimethylammonium bromide (CTAB) at equal concentrations. As can be seen from the graph, CTAB foamability is very strong, and almost no foam is formed at the same concentration of N2-C12-N2, which means that the foamability of N2-C12-N2 is very poor, so that a large amount of foam can be prevented from being generated in actual use, and the use of defoamer is reduced.
4. Sterilization performance test of N2-C12-N2
The N2-C12-N2 prepared in example 1 was used as test water in the Yangtze river, and the sterilization effect was evaluated according to the number of bacteria by a static sterilization test of heterotrophic bacteria with reference to GB/T22595-2008 "evaluation method of biocide energy efficiency-heterotrophic bacteria". Culture temperature: (29+ -1) deg.C, and the total number of bacteria was measured after maintaining the temperature for 72 hours. The result shows that when the concentration of N2-C12-N2 is more than 150mg/L, the sterilization rate can reach more than 98.4%, and the high-efficiency sterilization performance is shown.
5. Testing of algae removal performance of N2-C12-N2
N2-C12-N2 prepared in example 1, 50mL of the mixed algae solution was added to a 500mL conical flask, and 20mL of water was added thereto, and after culturing at an illumination intensity of 3000lux at room temperature for two days, the algae cell content reached 10 6 And/cubic meter or more. Adding N2-C12-N2 solution with certain concentration, and observingObserving the change of the content of algae cells with time. The result shows that when the concentration of N2-C12-N2 is more than 200mg/L, the algae removal rate can reach 99.8% after three days, and the good algae removal effect is shown.
Example 3: preparation of composite sterilizing scale-inhibiting penetrating agent by using N2-C12-N2
100 ppm, 200ppm and 300ppm of N2-C12-N2 prepared in the example 1 are respectively mixed with 200ppm of sodium polyacrylate to obtain the compound sterilization scale inhibition penetrant with different N2-C12-N2 concentrations.
The sterilizing and scale inhibiting penetrating agent is placed in a constant temperature cabinet at 25 ℃ for 7 days.
FIG. 5 is a photograph showing the appearance of an aqueous solution after mixing N2-C12-N2 at various concentrations with 200ppm sodium polyacrylate and standing for 7 days. As can be seen from the figure, the mixed solution is clear and transparent, which shows that N2-C12-N2 has good compatibility with the anionic polymer.
Example 4: detection of scale inhibition performance of composite sterilization scale inhibition penetrant
Taking the compound sterilizing scale-inhibiting penetrating agents with different N2-C12-N2 concentrations prepared in the example 3, adding 5mmol/L CaCl 2 After that, 5mmol/L Na is added 2 CO 3 And taking a macroscopic picture after uniformly mixing.
FIG. 6 shows CaCl at equimolar concentration (5 mmol/L) 2 With Na and Na 2 CO 3 The appearance photograph of the mixed aqueous solution of N2-C12-N2 with different concentrations and 200ppm sodium polyacrylate is not added/added into the aqueous solution. As can be seen from the figure, compared with the control group, the transmittance of the system is higher after the mixed aqueous solution of N2-C12-N2 with different concentrations and 200ppm sodium polyacrylate is added, which indicates that CaCO is formed 3 Less precipitate.
Example 5: caCO (CaCO) with composite sterilizing and scale inhibiting penetrating agent 3 Influence of morphology
Taking the compound sterilizing scale-inhibiting penetrating agents with different N2-C12-N2 concentrations prepared in the example 3, adding 5mmol/L CaCl 2 After that, 5mmol/L Na is added 2 CO 3 Mixing, placing in 70 deg.C incubator for 4 hr, collecting CaCO 3 The precipitate was photographed.
FIG. 7 shows the reaction at equimolar ratioConcentration (5 mmol/L) CaCl 2 With Na and Na 2 CO 3 CaCO formed by mixing water solutions of N2-C12-N2 with different concentrations and 200ppm sodium polyacrylate is not added into the water solution 3 Is a microscopic comparison photograph of (c). As can be seen from the figure, caCO of the control group 3 The crystal presents a regular calcite structure and CaCO 3 Crystal growth builds up to form calcium carbonate scale. Adding the mixed solution of N2-C12-N2 and sodium polyacrylate, caCO 3 The crystal is transformed from calcite-shaped structure to spheroid structure with irregular shape due to the adsorption of scale inhibitor on CaCO 3 Crystal surface, caCO 3 The crystal can not grow normally and is finally dispersed in water in the form of loose tiny grains, which indicates that the scale inhibitor sodium polyacrylate still has excellent scale inhibition performance after being mixed with the high-efficiency bactericide N2-C12-N2.
Example 6: sterilization performance test of composite sterilization scale inhibition penetrant
The composite sterilization scale inhibition penetrating agent prepared in the example 3 is taken, water for test is Yangtze river water, and the sterilization effect is evaluated according to the number of bacteria by adopting a heterotrophic static sterilization experiment according to the method for evaluating the energy efficiency of the biocide, namely heterotrophic bacteria, with reference to GB/T22595-2008. Culture temperature: (29+ -1) deg.C, and the total number of bacteria was measured after maintaining the temperature for 72 hours. The result shows that when the concentration of N2-C12-N2 in the composite sterilization and scale inhibition penetrant is equal to 150mg/L, the sterilization rate of the composite sterilization and scale inhibition penetrant can reach more than 99.4%, and the composite sterilization and scale inhibition penetrant has high-efficiency sterilization performance.
Example 7: algae removal performance test of composite sterilizing scale inhibiting penetrating agent
Taking the composite sterilization scale inhibition penetrating agent prepared in the example 3, adding 50mL of mixed algae liquid into a 500mL conical bottle, adding 20mL of water, and culturing for two days under the condition of room temperature and illumination intensity of 3000lux, wherein the algae cell content reaches 10 6 And (3) more than one cubic meter per cubic meter. Adding a compound sterilizing and scale inhibiting penetrating agent with a certain concentration, and observing the change condition of the content of algae cells along with time. The result shows that when the N2-C12-N2 in the composite sterilization scale inhibition penetrating agent is more than 200mg/L, the algae removal rate can reach 99.7% after three days, and the good algae removal effect is shown.
Example 8: application of composite sterilizing scale-inhibiting penetrating agent in water treatment
Taking the composite sterilization scale inhibition penetrating agent prepared in the example 3, taking the water for test as Yangtze river water, adding 100mL of Yangtze river water into a 500mL conical bottle, adding the composite sterilization scale inhibition penetrating agent with a certain concentration to ensure that the final concentration of N2-C12-N2 is 150mg/L, the final concentration of sodium polyacrylate is 200mg/L, and determining the total number of bacteria and algae cells and the precipitation quantity in the water after the constant temperature is maintained for 72 hours.
The result shows that the sterilization and algae removal efficiency in the cooling water reaches more than 99 percent, and the water body is clear, free of foam and free of sediment.
Comparative example 1: tetrameric quaternary ammonium salt performance detection
1. Preparation of tetrameric quaternary ammonium salt
The synthetic route is as follows:
3-bromopropyl trimethylammonium bromide (33 g,0.13 mol) and N, N, N ', N' -tetramethyl ethylenediamine (7.0 g,0.06 mol) were added to a 250mL single vial. After stirring at 80℃for 20h, the heating was stopped. And (3) after the reaction mixture is cooled, carrying out vacuum filtration, recrystallizing the obtained solid twice, and carrying out vacuum filtration and vacuum drying to obtain white powder, thus obtaining the target product of the oligomeric quaternary ammonium salt scale inhibitor.
2. Sterilization performance of tetrameric quaternary ammonium salt:
the test water is Yangtze river water, and the sterilization effect is evaluated according to the number of bacteria by adopting a heterotrophic bacteria static method sterilization experiment according to GB/T22595-2008 "evaluation method of biocide energy efficiency" by heterotrophic bacteria. Culture temperature: (29+ -1) deg.C, and the total number of bacteria was measured after maintaining the temperature for 72 hours.
The result shows that when the concentration of the tetrameric cation scale inhibitor is 120mg/L, the sterilization rate can reach 69.2 percent, and when the concentration of N2-C12-N2 is 100mg/L, the sterilization rate can reach more than 98.4 percent, and the higher efficient sterilization performance is shown.
3. Salt resistance of the tetrameric quaternary ammonium salt:
50mmol/L of the mixture was prepared in example 1The obtained N2-C12-N2 and 50mmol/L tetrameric quaternary ammonium salt are respectively mixed with 1000mmol/L CaCl 2 Mixing, and placing in a constant temperature cabinet at 25 ℃ for 7 days.
FIG. 8 shows that N2-C12-N2 and the tetrameric quaternary ammonium salt are present in equal concentrations of 50mmol/L with 1000mmol/L CaCl, respectively 2 Photograph of the appearance of the mixed aqueous solution. From the figure, the solution of N2-C12-N2 still keeps clear and transparent under the high-salt environment, and the tetrameric quaternary ammonium salt is separated out, which shows that the salt tolerance of N2-C12-N2 is better.
Comparative example 2: performance detection of composite sterilization scale inhibition penetrant prepared by using novel Jielde
100 ppm, 200ppm and 300ppm of benzalkonium chloride and 200ppm of sodium polyacrylate are respectively mixed to obtain the composite sterilizing and scale inhibiting penetrating agent with different benzalkonium chloride concentrations.
The sterilizing and scale inhibiting penetrating agent is placed in a constant temperature cabinet at 25 ℃ for 7 days.
FIG. 9 is a photograph showing the appearance of an aqueous solution of various concentrations of benzalkonium chloride mixed with 200ppm sodium polyacrylate after standing for 7 days. From the figure, the mixed solution is turbid and separated out, which indicates that the novel Jieling and anionic polymer do not have good compatibility.
Claims (10)
1. A compound having the molecular structure:
2. the compound of claim 1, wherein the compound is obtained by the reaction of the formula:
3. a bactericidal scale-inhibiting penetrant comprising a compound according to any one of claims 1-2 and an anionic surfactant.
4. A bactericidal scale inhibiting osmotic agent according to claim 3 wherein the ratio of the compound to anionic scale inhibitor is in the range of 1:2 to 3:2.
5. A bactericidal scale-inhibiting osmotic agent according to claim 3 wherein the concentration of the compound is 100 to 300ppm.
6. A bactericidal scale-inhibiting penetrant according to claim 3 wherein the concentration of the anionic scale-inhibiting agent sodium polyacrylate is 200ppm to 500ppm.
7. Use of a compound according to any one of claims 1 to 2 in water treatment.
8. The use according to claim 7, wherein the use includes, but is not limited to, industrial water treatment, cooling water systems, potable water disinfection.
9. Use of the bactericidal scale-inhibiting penetrating agent of any one of claims 3 to 6 in water treatment.
10. The use according to claim 9, wherein the use includes, but is not limited to, industrial water treatment, cooling water systems, potable water disinfection.
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