CN114671833B - Furan gemini quaternary ammonium salt compound and preparation method and application thereof - Google Patents
Furan gemini quaternary ammonium salt compound and preparation method and application thereof Download PDFInfo
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- C—CHEMISTRY; METALLURGY
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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Abstract
The application discloses a furan gemini quaternary ammonium salt compound, a preparation method and application thereof, wherein the furan gemini quaternary ammonium saltThe compound has a structural formula shown in a formula I.
Description
Technical Field
The invention belongs to the technical field of rust inhibitors, and particularly relates to a furan gemini quaternary ammonium salt compound, a preparation method and application thereof.
Background
Traditional inorganic rust inhibitors such as chromates, nitrites, phosphates and the like have high toxicity and are extremely easy to pollute the environment, and are phased out to be used at present. Organic surfactant type rust inhibitors are receiving a great deal of attention because of their good rust inhibitive performance and low environmental pollution. The gemini quaternary ammonium salt surfactant is a novel surfactant which is formed by combining two or more single-chain quaternary ammonium salt surfactants through a connecting group, and the special gemini quaternary ammonium salt molecular structure of the gemini quaternary ammonium salt surfactant endows the surfactant with more excellent performance. Compared with the traditional single-chain quaternary ammonium salt structure, the gemini quaternary ammonium salt surfactant has stronger surface/interfacial activity, can form a more compact protective film through electrostatic adsorption of double N-head groups and the surface of carbon steel, and can form high-efficiency protection on metals. The gemini quaternary ammonium salt antirust agent has the characteristics of low toxicity, environmental friendliness, good water solubility and the like, and can not cause harm to the environment while realizing efficient metal corrosion prevention.
Disclosure of Invention
Aiming at the environmental protection requirement and the problems existing in the prior art, the invention provides a furan bisquaternary ammonium salt compound, a preparation method and application thereof, wherein the furan bisquaternary ammonium salt compound has furan rings, nitrogen atoms and multiple bonds, can be used as an antirust agent, and improves the performance of the antirust agent by constructing two furan quaternary ammonium salt functional groups in a structure and utilizing pi electrons in the furan rings and lone pair electrons in the nitrogen atoms. The rust inhibitor can be orderly and tightly adsorbed on the surface of carbon steel through electrostatic interaction force between nitrogen atoms and iron or pi-d electron interaction between furan rings and iron, so that an acidic corrosion medium and a carbon steel substrate are effectively isolated and efficiently preserved. The preparation raw material of the antirust agent is biological-based platform micromolecular 5-hydroxymethylfurfural, and the antirust agent has the advantages of wide raw material sources, environmental protection and reproducibility.
In order to solve the technical problems, the invention adopts the following technical scheme:
a furan gemini quaternary ammonium salt compound which is a compound with a structural formula shown in a formula I;
the structure of the compound contains two quaternary ammonium salt substituents. The substituent on the nitrogen atom of the quaternary ammonium salt group is three ethyl groups, and the anion is chloride.
The preparation method of the furan gemini quaternary ammonium salt compound comprises the following steps:
(1) Reacting a mixture containing a compound i and a compound ii in the presence of an alkaline substance to obtain an olefin compound;
the compound i is selected from compounds having a structural formula shown in a formula III:
the compound ii is selected from compounds having a structural formula shown in formula IV:
(2) Mixing the olefin compound prepared in the step (1) with a halogenating reagent and then reacting to obtain a halogenated intermediate product;
(3) Reacting the halogenated intermediate product prepared in the step (2) with triethylamine to obtain a single-chain quaternary ammonium salt compound;
(4) Reacting the single-chain quaternary ammonium salt compound prepared in the step (3) with a peroxide reagent to obtain an epoxidized single-chain quaternary ammonium salt compound;
(5) And (3) reacting the epoxidized single-chain quaternary ammonium salt compound prepared in the step (4) in the presence of an alkaline substance or an acidic substance to obtain the furan gemini quaternary ammonium salt compound.
Further, the alkaline substance in the step (1) is at least one selected from butyl lithium and sodium bis (trimethylsilyl) amide; the reaction temperature in the step (1) is-78-30 ℃ and the reaction time is 1-18 h; the molar ratio of the compound i to the compound ii is (1-5): 1-10.
Further, the halogenating reagent in the step (2) is at least one selected from oxalyl chloride, thionyl chloride, phosphorus oxychloride, phosphorus tribromide and concentrated hydrochloric acid; the reaction temperature in the step (2) is 0-30 ℃; the reaction time is 0.5 h-10 h.
Further, the molar ratio of the olefin compound, the halogenated reagent and the triethylamine is (1-5): 1-10.
Further, the reaction temperature in the step (3) is 50-100 ℃; the reaction time is 1 h-10 h.
Further, the molar ratio of the single-chain quaternary ammonium salt compound to the peroxide reagent in the step (4) is 1-5:1-10; the peroxide reagent is at least one selected from peroxybenzoic acid, hydrogen peroxide and peroxyacetic acid; the reaction temperature in the step (4) is 50-100 ℃; the reaction time is 1 h-10 h.
Further, the alkaline substance in the step (5) is at least one selected from butyl lithium, sodium bis (trimethylsilyl) amide, sodium hydroxide and potassium hydroxide; the acid is selected from hexafluoroantimonic acid; the molar ratio of the epoxidized single-chain quaternary ammonium salt compound to the alkaline substance is (0.1-1): 1-10; the molar ratio of the epoxidized single-chain quaternary ammonium salt compound to the acid substance is (0.1-1): 1-10; the reaction temperature in the step (5) is 30-100 ℃; the reaction time is 1 h-10 h.
The furan gemini quaternary ammonium salt compound prepared by the preparation method of the furan gemini quaternary ammonium salt compound is applied to serving as an antirust agent, wherein the antirust agent is used for corrosion prevention of carbon steel.
Alternatively, the furan gemini quaternary ammonium compound may be prepared starting from aldehyde 3 and phosphine reagent 4.
First, aldehyde 3 and phosphine reagent 4 are added thereto in the presence of a solvent ether compound and an alkaline substance to react at-78 ℃ to prepare compound 5. The hydroxyl group in compound 5 was then chlorinated using thionyl chloride to prepare chlorinated compound 6. And nucleophilic substitution of triethylamine on chloro compound to obtain single-chain quaternary ammonium salt compound 7.
And oxidizing the single-chain quaternary ammonium salt compound 7 by using a peroxide reagent to prepare epoxide 8. Finally, the epoxide is subjected to ring opening crosslinking by utilizing an alkaline substance or an acid substance, and the furan gemini quaternary ammonium salt compound 1 is prepared. The preparation route is as follows:
the invention has the beneficial effects that: the furan gemini quaternary ammonium salt compound provided by the invention has excellent corrosion resistance on carbon steel as an organic rust inhibitor. Through static weightlessness experiments, the furan gemini quaternary ammonium salt compound is compared with a single-chain quaternary ammonium salt antirust agent, and the furan gemini quaternary ammonium salt antirust agent provided by the invention has stronger corrosion resistance. After the corrosion inhibitor is sprayed on the surface of the carbon steel, compared with a single-chain quaternary ammonium salt rust inhibitor, the corrosion rate of the carbon steel is reduced by more than 2 times.
Detailed Description
The invention will be further illustrated with reference to specific examples. It is to be understood that the following examples are intended to illustrate the present invention and are not to be construed as limiting the scope of the invention, and that numerous insubstantial modifications and adaptations can be made by those skilled in the art in light of the foregoing disclosure.
Unless otherwise indicated, both the starting materials and the catalysts in the examples of the present application were purchased commercially.
Example 1
The synthesis of the single-chain quaternary ammonium salt 7 comprises the following steps:
step one: to a mixed solution of 5-hydroxymethylfurfural (100 mg,1 eq), (1-nonyl) triphenylphosphine bromide (1.2 eq), 4A molecular sieve (150 mg), anhydrous HMPA (0.4 mL) in tetrahydrofuran (2 mL) at-78deg.C was added dropwise a solution of butyllithium in tetrahydrofuran (1.6M, 1.2 eq), followed by stirring at-78deg.C. After the reactant 5-hydroxymethylfurfural disappears, dropwise adding a saturated ammonium chloride aqueous solution to quench the reaction, then adding 100mL of ethyl acetate into the reaction system, washing and extracting three times with saturated saline water, collecting an organic phase, extracting an aqueous phase twice with ethyl acetate, combining the organic phases, adding anhydrous magnesium sulfate or anhydrous sodium sulfate for drying, filtering to remove a drying agent, concentrating the organic phase, and carrying out gradient elution on a silica gel column with petroleum ether to ethyl acetate (v: v) =10:1-5:1 to obtain a purified target olefin product 5.
Step two: dichloromethane (1 mL) was added to the compound olefin product (100 mg,1 eq) obtained in step one at 0 ℃ to obtain a mixed solution, thionyl chloride (1.1 eq) was slowly added dropwise to the mixed solution, stirred at room temperature for 0.5 hours, and the reaction was monitored every 0.5 hour time plate (monitored with petroleum ether: ethyl acetate (v: v) =10:1). After the reaction is finished, dropwise adding saturated sodium bicarbonate aqueous solution into the reaction liquid, slowly quenching the reaction until no bubbles are generated in the reaction liquid, adding 50ml of dichloromethane into the system, washing the mixed system with the saturated sodium bicarbonate aqueous solution and saturated saline water for three times, combining organic solvents for three times, drying, filtering, concentrating the organic phase to obtain a chloro crude product 6, and directly using the chloro crude product for the next reaction.
Step three: acetonitrile solvent (2 mL) and triethylamine (1.2 eq) are added into the chloro crude product obtained in the step two, the reaction is carried out for 3 hours at 80 ℃, the chlorinated raw material is monitored every 1.5 hours (petroleum ether is used for monitoring the chloro raw material by using ethyl acetate (v: v) =10:1, the quaternary ammonium salt product is monitored by using DCM to MeOH (v: v) =5:1), after the reaction is finished, the reaction liquid is concentrated by using a rotary evaporator, 50mL of dichloromethane is added into the concentrated liquid, the saturated saline is used for washing and extracting for three times, and the organic phases of the three times are combined, dried, filtered and concentrated. The purified single-chain quaternary ammonium salt product 7 was then eluted with dichloromethane: methanol (v: v) =20:1 on a silica gel column.
Example 2
The synthesis of furan gemini quaternary ammonium salt 1 comprises the following steps:
step four: toluene (1 mL) was added to compound 7 (100 mg,1 eq) obtained in example 1 to obtain a mixed solution, and a toluene mixed solution of peroxybenzoic acid (2.1 eq) was slowly added dropwise to the mixed solution, followed by stirring at 70 ℃ for 5 hours, and the reaction was monitored every 2 hours (monitored with methylene chloride: methanol=4:1). After no reactant, dropwise adding saturated sodium sulfite aqueous solution into the reaction solution, slowly quenching the reaction, adding 50ml of dichloromethane into the system, washing the mixed system for three times by using saturated sodium bicarbonate aqueous solution and saturated saline solution, combining organic solvents for three times, drying, filtering, concentrating the organic phase to obtain crude product of epoxide 8, and directly using the crude product in the next reaction.
Step five: to the crude epoxide product obtained in the fourth step, water (2 mL) and hexafluoroantimonic acid (0.5 mg,0.5 wt%) were added, the reaction was carried out at 0℃for 1 hour, the reaction was monitored every 0.5 hour (monitored by methylene chloride: methanol (v: v) =2:1), after the completion of the reaction, a saturated aqueous sodium carbonate solution was added dropwise to the reaction solution, the reaction was slowly quenched, 50mL of methylene chloride was added, the mixed system was washed three times with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous salt solution, the organic solvents were combined three times, dried, and filtered. The purified target product furan gemini quaternary ammonium salt was then eluted with dichloromethane: methanol (v: v) =2:1 on a silica gel column.
Alternatively, water (2 mL) and sodium hydroxide (8 mg,0.1 m) were added to the crude epoxide product obtained in the fourth step, the reaction was carried out at 0 ℃ for 1 hour, the reaction was monitored every 0.5 hour (monitored by methylene chloride: methanol (v: v) =2:1), after the completion of the reaction, a saturated aqueous ammonium chloride solution was added dropwise to the reaction solution, the reaction was slowly quenched, 50mL of methylene chloride was added to the system, the mixed system was washed three times with a saturated aqueous ammonium chloride solution and a saturated aqueous salt solution, the organic solvents of the three times were combined, dried, and filtered. The purified target product furan gemini quaternary ammonium salt was then eluted with dichloromethane: methanol (v: v) =2:1 on a silica gel column.
Example 3
Static weightlessness evaluation
400mL of 1mol/L HCl solution is added into a 500mL glass bottle, furan gemini quaternary ammonium salt is added as an antirust agent, the temperature is raised to 60 ℃, and the pretreated Q235 steel sheet is put into the glass bottle to be corroded for 4 hours. After the corrosion reaction is finished, taking out a test piece, and performing test post-treatment on the test piece by referring to SY5273-2014 corrosion inhibitor performance index for oilfield produced water treatment and evaluation method: soaking in pickling solution for 2min, cleaning with detergent powder, soaking in ethanol solution for dehydration, blow-drying with cold air, weighing, calculating corrosion rate, and comparing with blank and the single-chain quaternary ammonium salt antirust agent, and the results are shown in table 1.
The corrosion rate is calculated as follows:
wherein V is the corrosion rate, mm/a
Δw is the weight difference, g, between the sample before and after corrosion;
s is the area of the test piece，cm 2 ；
ρ is the density of the test piece, 7.85g/cm 3 ；
t is the time for performing the experiment, h;
carbon steel specification 40 x 13 x 2 (mm)
The static weightlessness evaluation results are shown in Table 1.
TABLE 1 static weight loss evaluation results
| Sequence number | Rust inhibitor | Additive amount (ppm) | Weightlessness (g) | Corrosion Rate (mm/a) |
| 1 | Furan gemini quaternary ammonium salt | 300 | 0.0052 | 2.789 |
| 2 | Blank space | 0.4768 | 255.8 | |
| 3 | Single-chain quaternary ammonium salt | 300 | 0.0112 | 6.009 |
From the data of the table, the furan gemini quaternary ammonium salt compound provided by the invention shows extremely strong anti-corrosion effect on carbon steel as an organic corrosion inhibitor. The corrosion rate is reduced by more than 2 times compared with the single-chain quaternary ammonium salt rust inhibitor.
The foregoing has shown and described the basic principles and main features of the present invention and the advantages of the present invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, and that the above embodiments and descriptions are merely illustrative of the principles of the present invention, and various changes and modifications may be made without departing from the spirit and scope of the invention, which is defined in the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (10)
1. The furan gemini quaternary ammonium salt compound is characterized in that the furan gemini quaternary ammonium salt compound is a compound with a structural formula shown in a formula I;
2. the method for producing a furan gemini quaternary ammonium salt compound according to claim 1, comprising the steps of:
(1) Reacting a mixture containing a compound i and a compound ii in the presence of an alkaline substance to obtain an olefin compound;
the compound i is selected from compounds having a structural formula shown in a formula III:
the compound ii is selected from compounds having a structural formula shown in formula IV:
the structural formula of the olefin compound is as follows:
(2) Mixing the olefin compound prepared in the step (1) with a halogenating reagent and then reacting to obtain a halogenated intermediate product;
the structural formula of the halogenated intermediate product is as follows:
(3) Reacting the halogenated intermediate product prepared in the step (2) with triethylamine to obtain a single-chain quaternary ammonium salt compound;
the halogenated intermediate product has the following structural formula:
(4) Reacting the single-chain quaternary ammonium salt compound prepared in the step (3) with a peroxide reagent to obtain an epoxidized single-chain quaternary ammonium salt compound;
the structural formula of the epoxidized single-chain quaternary ammonium salt compound is as follows:
(5) Reacting the epoxidized single-chain quaternary ammonium salt compound 8 prepared in the step (4) in the presence of an alkaline substance or an acidic substance to obtain a furan gemini quaternary ammonium salt compound, wherein the furan gemini quaternary ammonium salt compound has the following structural formula:
3. the method for producing furan gemini quaternary ammonium salt compound 1 according to claim 2, characterized in that: the alkaline matter in the step (1) is at least one selected from butyl lithium and sodium bis (trimethylsilyl) amide; the reaction temperature in the step (1) is-78-30 ℃ and the reaction time is 1-18 h; the molar ratio of the compound i to the compound ii is (1-5): 1-10.
4. The method for producing furan gemini quaternary ammonium salt compound 1 according to claim 2, characterized in that: the halogenated reagent in the step (2) is at least one selected from oxalyl chloride, thionyl chloride, phosphorus oxychloride, phosphorus tribromide and concentrated hydrochloric acid; the reaction temperature in the step (2) is 0-30 ℃; the reaction time is 0.5 h-10 h.
5. The method for producing furan gemini quaternary ammonium salt compound 1 according to claim 2, characterized in that: the mol ratio of the alkene compound, the halogenated reagent and the triethylamine is (1-5): 1-10.
6. The method for producing furan gemini quaternary ammonium salt compound 1 according to claim 2, characterized in that: the reaction temperature in the step (3) is 50-100 ℃; the reaction time is 1 h-10 h.
7. The method for producing furan gemini quaternary ammonium salt compound 1 according to claim 2, characterized in that: the molar ratio of the single-chain quaternary ammonium salt compound 7 to the peroxide reagent in the step (4) is (1-5): 1-10; the peroxide reagent is at least one selected from peroxybenzoic acid, hydrogen peroxide and peroxyacetic acid; the reaction temperature in the step (4) is 50-100 ℃; the reaction time is 1 h-10 h.
8. The method for producing a furan gemini quaternary ammonium salt compound according to claim 2, characterized in that: the alkaline matter in the step (5) is at least one selected from butyl lithium, sodium bis (trimethylsilyl) amide, sodium hydroxide and potassium hydroxide; the acid is selected from hexafluoroantimonic acid; the molar ratio of the epoxidized single-chain quaternary ammonium salt compound to the alkaline substance is (0.1-1): 1-10; the molar ratio of the epoxidized single-chain quaternary ammonium salt compound to the acid substance is (0.1-1): 1-10; the reaction temperature in the step (5) is 30-100 ℃; the reaction time is 1 h-10 h.
9. Use of the furan gemini quaternary ammonium salt compound prepared by the preparation method of the furan gemini quaternary ammonium salt compound according to any one of claims 2-8 as an antirust agent.
10. The use according to claim 9, characterized in that: the antirust agent is used for corrosion prevention of carbon steel.
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| US5993693A (en) * | 1998-11-09 | 1999-11-30 | Nalco/Exxon Energy Chemicals, L.P. | Zwitterionic water-soluble substituted imine corrosion inhibitors |
| WO2015100033A1 (en) * | 2013-12-27 | 2015-07-02 | Dow Global Technologies Llc | Corrosion inhibiting compositions including bis-imidazoline compounds derived from enriched linear tetramines |
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