Bio-based gemini quaternary ammonium salt compound as well as preparation method and application thereof
By using 5-HMF to synthesize bio-based bimini quaternary ammonium compounds with furan rings, quaternary ammonium substituents, bistatic action sites and long alkyl chains, the problem of insufficient performance of existing metal preservatives is solved, and high efficiency and long-lasting corrosion inhibition and high economic benefits are achieved.
Patent Information
- Application Number
- CN202411808263.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-12-10
- Publication Date
- 2025-03-21
AI Technical Summary
The existing metal preservatives have problems such as high biotoxicity, high environmental hazards and poor anti-rust performance. The traditional inorganic corrosion inhibitors are insufficient, and the synthesis of organic corrosion inhibitors is complex and there are many by-products, which limits their application.
Using 5-HMF as raw material, bio-based bimini quaternary ammonium salt compounds with furan rings, quaternary ammonium salt substituents, bistatic action sites and long alkyl chains are used as corrosion inhibitors. The compound constructs quaternary ammonium salt functional groups and alkyl long chains in the structure, acting as hydrophilic and hydrophobic functional groups respectively, forming a protective film to slow down metal corrosion.
It achieves an efficient and lasting corrosion inhibition effect, exhibits more obvious anti-rust performance than ordinary corrosion inhibitors, has high economic benefits, and forms a protective film on the metal surface, significantly slowing down the corrosion rate.
Smart Images

Figure CN119661481A_ABST
Abstract
Description
Technical Field
[0001] The present application relates to a bio-based gemini quaternary ammonium salt compound and a preparation method and application thereof, belonging to the technical field of corrosion inhibition monomer preparation. Background Art
[0002] Metal corrosion protection is a serious problem faced by the machinery, oil and gas industries. Material corrosion not only causes huge economic losses, but severe corrosion can also cause equipment and facilities to be damaged and scrapped, toxic media leaks, fires, explosions and other catastrophic accidents, causing irreparable losses to human life safety, the environment and society.
[0003] Corrosion inhibitors are considered to be one of the most effective means of metal corrosion prevention to solve the problem of metal corrosion. Traditional inorganic corrosion inhibitors have high biological toxicity, great environmental hazards (such as chromates, nitrites, phosphates, mercury salts, etc.), and poor anti-rust performance. Organic corrosion inhibitors are relatively green and safer than inorganic corrosion inhibitors, but their complex synthesis routes and more by-products also limit the application of this type of corrosion inhibitor in actual production and life.
[0004] In view of this, the present invention provides a bio-based quaternary ammonium salt corrosion inhibitor with good corrosion inhibition performance. Summary of the invention
[0005] In view of the problems existing in the prior art, the present invention provides a bio-based quaternary ammonium salt compound and a preparation method and application thereof. The bio-based quaternary ammonium salt compound uses 5-HMF as a raw material, has a furan ring, a quaternary ammonium salt substituent, a double electrostatic action site and a long alkyl chain in its structure, can be used as a corrosion inhibitor, and by constructing a quaternary ammonium salt functional group and an alkyl long chain in the structure, they act as a hydrophilic functional group and a hydrophobic functional group respectively. When the quaternary ammonium salt corrosion inhibitor contacts a metal surface, a protective film can be formed on the surface thereof, which includes physical adsorption and chemical adsorption, thereby achieving the effect of protecting steel (metal) and slowing down its corrosion rate, and having extremely high economic benefits.
[0006] In order to solve the above technical problems, the present invention adopts the following technical solutions:
[0007] A bio-based gemini quaternary ammonium salt compound, wherein the bio-based gemini quaternary ammonium salt compound is a compound having a structural formula shown in Formula I;
[0008]
[0009] Among them, R 1 One selected from cyclohexanone, cyclopentanone, acetone, 2-octanone, and 2-pentanone;
[0010] R 2 Selected from C4~C 24 Alkyl (except C 19 , C21 outside);
[0011] X is a halogen element, and the halogen is selected from at least one of Cl, I, and Br.
[0012] The present invention also provides a method for preparing the bio-based gemini quaternary ammonium salt compound, the method comprising:
[0013] Using 5-hydroxymethylfurfural (5-HMF) as a raw material, a compound having a gemini quaternary ammonium salt functional group and an alkyl long chain is constructed, comprising the following steps:
[0014] (1) adding 5-HMF and ketone into solvent I to react and obtain a condensed intermediate product;
[0015] (2) adding the condensed intermediate product and the halogenation reagent into solvent II for reaction to obtain a halogenated intermediate product;
[0016] (3) Adding the halogenated intermediate product and the amine compound into solvent III for reaction to obtain the bio-based gemini quaternary ammonium salt compound. The reaction scheme is as follows:
[0017]
[0018] Furthermore, the ketone in step (1) is one of cyclohexanone, cyclopentanone, acetone, 2-octanone and 2-pentanone, and the solvent I is methanol.
[0019] Furthermore, in step (1), the molar ratio of 5-HMF to ketone is 2:1, the reaction temperature is 0° C. to 30° C., and the reaction time is 0.5 to 12 h.
[0020] Furthermore, the halogenating agent in step (2) is selected from at least one of thionyl chloride, phosphorus oxychloride, concentrated hydrochloric acid, iodobenzene, and phosphorus tribromide, and the solvent II is selected from at least one of dichloromethane and dichloroethane.
[0021] Furthermore, in the step (2), the molar ratio of the intermediate product after condensation to the halogenation reagent is (1:2), the reaction temperature is 0°C to 30°C, and the reaction time is 0.5 to 12 hours.
[0022] Furthermore, the solvent III in step (3) is selected from at least one of acetonitrile and dichloroethane, and the structural formula of the amine compound is as follows:
[0023] The number of carbon atoms in the straight chain alkyl group R is (excluding C 19 , C 21 outside).
[0024] Preferably, the amine compound in step (3) is selected from at least one of N,N-dimethylbutylamine, N,N-dimethyloctylamine, N,N-dimethyldodecylamine and N,N-dimethylhexadecylamine.
[0025] Furthermore, in step (3), the molar ratio of the halogenated intermediate product to the amine compound is 1:2, the reaction temperature is 60° C. to 100° C., and the reaction time is 0.5 to 12 h.
[0026] The present invention also provides the use of at least one of the above-mentioned bio-based quaternary ammonium salt compound and the bio-based quaternary ammonium salt compound prepared by the above-mentioned preparation method as a corrosion inhibitor.
[0027] The beneficial effects of this application include:
[0028] 1) The bio-based quaternary ammonium salt compound of the present invention uses 5-HMF as a raw material to synthesize a gemini quaternary ammonium salt corrosion inhibitor in a safe and stable route, and has a more lasting and obvious corrosion inhibition effect compared with common corrosion inhibitors.
[0029] 2) The present application provides a bio-based quaternary ammonium salt compound and its preparation method and application. The bio-based quaternary ammonium salt compound uses 5-HMF as a raw material, has a furan ring, a quaternary ammonium salt substituent, a double electrostatic interaction site and a long alkyl chain in the structure, and can be used as a corrosion inhibitor. By constructing a quaternary ammonium salt functional group and an alkyl long chain in the structure, they act as a hydrophilic functional group and a hydrophobic functional group respectively. When the quaternary ammonium salt corrosion inhibitor contacts the metal surface, a protective film can be formed on its surface, including physical adsorption and chemical adsorption, to achieve the effect of protecting steel (metal), slowing down its corrosion rate, and having extremely high economic benefits. These properties enable the quaternary ammonium salt corrosion inhibitor to show an excellent corrosion inhibition effect. BRIEF DESCRIPTION OF THE DRAWINGS
[0030] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings required for use in the embodiments or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.
[0031] Figure 1 The weight loss test results of A3 carbon steel in 0.5M HCl solution with different concentrations of corrosion inhibitor (Example 1) added at 30°C, 40°C, 50°C and 60°C.
[0032] Figure 2 This is the H NMR spectrum of the bio-based gemini quaternary ammonium salt compound prepared in Example 1 of the present application. DETAILED DESCRIPTION
[0033] The present invention will be further described below in conjunction with specific embodiments. It should be understood that the following embodiments are only used to illustrate the present invention and are not used to limit the scope of the present invention, and those skilled in the art in this field can make some non-essential improvements and adjustments based on the content of the above invention.
[0034] Unless otherwise specified, the raw materials in the examples of this application were purchased through commercial channels.
[0035] The full name of the spot plate in the examples of the present application is thin layer chromatography.
[0036] The room temperature in the examples of the present application refers to 25°C.
[0037] Example 1
[0038] The bio-based gemini quaternary ammonium salt compound of this embodiment is: N, N'-(((1, 1')-(2-oxocyclohexane-1,3-diylidene)bis(methylimide))bis(furan-5,2-diyl))bis(methylene))bis(N, N-dimethylhexadecane-1-ammonium)
[0039]
[0040] The preparation method is as follows:
[0041] Step 1: Cyclohexanone (100 μL, 1 mmol) was added to 1 ml of 0.5 M sodium hydroxide solution, followed by 5-HMF (252 mg, 2 mmol) and 1 ml of methanol solution, and the reaction mixture was stirred at 25° C. for 12 hours. The precipitate was filtered and then washed with deionized water to obtain 280 mg of the compound as a yellow powder.
[0042] Step 2: Add the compound in the first step to a clean original bottom flask, add 3mL of dichloromethane, add a magnetic bar, stir for 10min, mix the condensation product with the reagent as much as possible, then slowly add 130μL of thionyl chloride, the reaction system will change from yellow to dark purple, and the reaction mixture will be stirred at 0℃ for 0.5h, where the ratio of substrate to thionyl chloride is 1:2. Spot plate to confirm whether the raw material is completely reacted, add an appropriate amount of saturated NaHCO3 aqueous solution after the reaction, slowly quench the reaction until no bubbles are generated in the reaction solution, add 50ml of dichloromethane to the system, wash the mixed system with saturated NaHCO3 aqueous solution and saturated brine, extract three times, combine the three organic solvents, dry, filter, and concentrate the organic phase to obtain the crude chloro product, which is directly used in the next step reaction.
[0043] Step 3: Add acetonitrile (3 ml) to the product of the previous step (1 equivalent) to obtain a mixed solution, then add N,N-dimethylhexadecylamine (2 equivalents) and stir at 80°C for 1 hour. Monitor the reaction every 20 minutes (monitor with dichloromethane DCM: methanol MeOH = 10:1). After the reaction is completed, the product is directly rotary evaporated to remove excess acetonitrile to obtain a crude product, which is then recrystallized. 2 mL of dichloromethane is added with a rubber-tipped dropper to dissolve the product until it reaches the saturation critical point, and 2 to 3 times the amount of petroleum ether is added. During this period, the original flask is continuously shaken to recrystallize a solid. The solid obtained by filtration is the crude product; on a silica gel column, a gradient elution of dichloromethane: methanol = 20:1 to 5:1 (volume ratio) is used to obtain the purified target product, that is, N, N'-(((1, 1')-(2-oxocyclohexane-1,3-diylidene)bis(methylimide))bis(furan-5,2-diyl))bis(methylene))bis(N, N-dimethylhexadecane-1-ammonium) is obtained. 'H NMR(400MHz, CDCl3) δ7.41(d,J=2.2Hz,4H),6.66(d,J=3.6Hz,2H),5.31(s,4H),3.37(s,16H), 2.87(d,J=6.6Hz,4H),1.90-1.81(m,8H),1.37-1.33(m,8H).1.24(s,61H),0.90-0.82(m,5H).
[0044] Example 2
[0045] The bio-based gemini quaternary ammonium salt compound of this embodiment is: N, N'-((1, 1')-(2-oxocyclohexane-1,3-diylidene)bis(methylethyl))bis(furan-5,2-diyl))bis(methylene))bis(N, N-dimethyldodecane-1-amino)
[0046]
[0047] The preparation method is as follows:
[0048] Step 1: Cyclohexanone (100 μL, 1 mmol) was added to 1 ml of 0.5 M sodium hydroxide solution, followed by 5-HMF (252 mg, 2 mmol) and 1 ml of methanol solution, and the reaction mixture was stirred at 25° C. for 12 hours. The precipitate was filtered and then washed with deionized water to obtain 280 mg of the compound as a yellow powder.
[0049] Step 2: Add the compound in the first step to a clean original bottom flask, add 3mL of dichloromethane, add a magnetic bar, stir for 10min, mix the condensation product with the reagent as much as possible, then slowly add 130μL of thionyl chloride, the reaction system will change from yellow to dark purple, and the reaction mixture will be stirred at 0℃ for 0.5h, where the ratio of substrate to thionyl chloride is 1:2. After the reaction for 0.5h, point the plate to confirm whether the raw material has reacted completely. After the reaction is completed, add an appropriate amount of saturated NaHCO3 aqueous solution, slowly quench the reaction until no bubbles are generated in the reaction solution, add 50ml of dichloromethane to the system, wash the mixed system with saturated NaHCO3 aqueous solution and saturated brine, extract three times, combine the three organic solvents, dry, filter, and concentrate the organic phase to obtain the crude chloro product, which is directly used in the next step reaction.
[0050] Step 3: Add acetonitrile (3 ml) to the product of the previous step (1 equivalent) to obtain a mixed solution, then add N,N-dimethyldodecylamine (2 equivalents) and stir at 80°C for 1 hour. Monitor the reaction every 20 minutes (monitor with dichloromethane DCM: methanol MeOH = 10:1). After the reaction is completed, the product can be directly rotary evaporated to remove excess acetonitrile to obtain a crude product, which needs to be recrystallized. 2 mL of dichloromethane is added with a rubber-tipped dropper to dissolve the product until it reaches the saturation critical point, and 2 to 3 times the amount of petroleum ether is added. During this period, the original flask is continuously shaken to recrystallize a solid. The solid obtained by suction filtration is the crude product; on a silica gel column, the target product is purified by gradient elution with dichloromethane: methanol = 20:1 to 5:1 (volume ratio), that is, N, N'-((1, 1')-(2-oxocyclohexane-1,3-diylidene)bis(methylethyl))bis(furan-5,2-diyl))bis(methylene))bis(N, N-dimethyldodecane-1-amino).
[0051] Example 3
[0052] The bio-based gemini quaternary ammonium salt compound of this embodiment is: N, N'-((1, 1')-(2-oxocyclohexane-1,3-diylidene)bis(methylimide))bis(furan-5,2-diyl))bis(methylene))bis(N, N-dimethyloctane-1-amino)
[0053]
[0054] The preparation method is as follows:
[0055] Step 1: Cyclohexanone (100 μL, 1 mmol) was added to 1 ml of 0.5 M sodium hydroxide solution, followed by 5-HMF (252 mg, 2 mmol) and 1 ml of methanol solution, and the reaction mixture was stirred at 25° C. for 12 hours. The precipitate was filtered and then washed with deionized water to obtain 280 mg of the compound as a yellow powder.
[0056] Step 2: Add the compound in the first step to a clean original bottom flask, add 3mL of dichloromethane, add a magnetic bar, stir for 10min, mix the condensation product with the reagent as much as possible, then slowly add 130μL of thionyl chloride, the reaction system will change from yellow to dark purple, and the reaction mixture will be stirred at 0℃ for 0.5h, where the ratio of substrate to thionyl chloride is 1:2. After the reaction for 0.5h, point the plate to confirm whether the raw material has reacted completely. After the reaction is completed, add an appropriate amount of saturated NaHCO3 aqueous solution, slowly quench the reaction until no bubbles are generated in the reaction solution, add 50ml of dichloromethane to the system, wash the mixed system with saturated NaHCO3 aqueous solution and saturated brine, extract three times, combine the three organic solvents, dry, filter, and concentrate the organic phase to obtain the crude chloro product, which is directly used in the next step reaction.
[0057] Step 3: Add acetonitrile (3 ml) to the product of the previous step (1 equivalent) to obtain a mixed solution, then add N,N-dimethyloctylamine (2 equivalents) and stir at 80°C for 1 hour. Monitor the reaction every 20 minutes (monitor with dichloromethane DCM: methanol MeOH = 10:1). After the reaction is completed, the product is directly rotary evaporated to remove the excess acetonitrile to obtain a crude product, which is then recrystallized. 2 mL of dichloromethane is added with a rubber-tipped dropper to dissolve the product until it reaches the saturation critical point, and 2 to 3 times the amount of petroleum ether is added. During this period, the original flask is continuously shaken to recrystallize a solid. The solid obtained by suction filtration is the crude product; on a silica gel column, the purified target product is obtained by gradient elution with dichloromethane: methanol = 20:1 to 5:1 (volume ratio), that is, N, N'-((1, 1')-(2-oxocyclohexane-1,3-diylidene)bis(methylimide))bis(furan-5,2-diyl))bis(methylene))bis(N, N-dimethyloctane-1-amino)
[0058] Example 4
[0059] The bio-based gemini quaternary ammonium salt compound of this embodiment is: N,N'-((((1,1')-(2-oxycyclohexane-1,3-dienyl)di(methylethyl))di(furan-5,2-diene))di(methylethyl))di(N,N-dimethylbutylamine)
[0060]
[0061] The preparation method is as follows:
[0062] Step 1: Cyclohexanone (100 μL, 1 mmol) was added to 1 ml of 0.5 M sodium hydroxide solution, followed by 5-HMF (252 mg, 2 mmol) and 1 ml of methanol solution, and the reaction mixture was stirred at 25° C. for 12 hours. The precipitate was filtered and then washed with deionized water to obtain 280 mg of the compound as a yellow powder.
[0063] Step 2: Add the compound in the first step to a clean original bottom flask, add 3mL of dichloromethane, add a magnetic bar, stir for 10min, mix the condensation product with the reagent as much as possible, then slowly add 130μL of thionyl chloride, the reaction system will change from yellow to dark purple, and the reaction mixture will be stirred at 0℃ for 0.5h, where the ratio of substrate to thionyl chloride is 1:2. After the reaction for 0.5h, point the plate to confirm whether the raw material has reacted completely. After the reaction is completed, add an appropriate amount of saturated NaHCO3 aqueous solution, slowly quench the reaction until no bubbles are generated in the reaction solution, add 50ml of dichloromethane to the system, wash the mixed system with saturated NaHCO3 aqueous solution and saturated brine, extract three times, combine the three organic solvents, dry, filter, and concentrate the organic phase to obtain the crude chloro product, which is directly used in the next step reaction.
[0064] Step 3: Add acetonitrile (5 ml) to the product of the previous step (1 equivalent) to obtain a mixed solution, then add N,N-dimethylbutylamine (2 equivalents) and stir at 80°C for 1 hour. Monitor the reaction every 20 minutes (monitor with dichloromethane DCM: methanol MeOH = 5:1). After the reaction is completed, the excess acetonitrile is removed by rotary evaporation to obtain a crude product, which is then recrystallized. 2 mL of dichloromethane is added with a rubber-tipped dropper to dissolve the product until it reaches the saturation critical point, and 2 to 3 times the amount of petroleum ether is added. During this period, the flask is continuously shaken to recrystallize a solid. The solid obtained by filtration is the crude product. On a silica gel column, a gradient elution with dichloromethane:methanol = 20:1 to 5:1 (volume ratio) is used to obtain the purified target product, namely, N,N'-((((1,1')-(2-oxycyclohexane-1,3-dienyl)di(methylethyl))di(furan-5,2-diene))di(methylethyl))di(N,N-dimethylbutylamine is obtained.
[0065] Experimental corrosion inhibition performance test
[0066] Weightlessness test
[0067] Usually we use the weight loss method to evaluate the corrosion efficiency of corrosion inhibitors. This evaluation method is easy to operate and the data is reliable. First, we tested the weight loss of carbon steel samples before and after immersion in 0.5M HCl solution containing different concentrations of quaternary ammonium salt corrosion inhibitors (0-20ppm) at 30℃, 40℃, 50℃ and 60℃, and the corrosion time was 3 hours.
[0068] The corrosion rate of carbon steel corrosion specimens is calculated as follows:
[0069]
[0070] Where v is the corrosion rate of the A3 carbon steel sample, △W is the weight difference of the sample before and after immersion (accurate to four decimal places, mg), and s is the total surface area of the A3 carbon steel corrosion sample (cm 2 ), ρ represents the density of the sample (7.85 g·cm -3 ), t is the immersion corrosion time (h) of the corrosion sample. In addition, the corrosion inhibition efficiency calculation formula of the test sample is as follows:
[0071]
[0072] Where η% represents the corrosion inhibition efficiency of the corresponding corrosion inhibitor, and v and v0 represent the corrosion rates of the sample in corrosive solutions containing and without corrosion inhibitors, respectively.
[0073] Figure 1 The mass loss of carbon steel samples before and after immersion in 0.5M HCl solution containing different concentrations of quaternary ammonium salt corrosion inhibitor (0-20ppm) was tested at temperatures of 30°C, 40°C, 50°C and 60°C. The corrosion time was 3 hours. The results are shown in Tables 1 to 4.
[0074] The mass loss of carbon steel samples before and after immersion in 0.5M HCl solution containing different concentrations of quaternary ammonium salt corrosion inhibitor (Example 1) 0-20ppm.
[0075] Table 1 30℃ static weight loss evaluation results
[0076] Concentration (ppm) Corrosion rate (mm / a) Corrosion inhibition efficiency (%) 0 12.74824049 0 1 8.270414744 35.1250492 5 1.321539578 89.6335531 10 1.03650163 91.8694534 15 1.007780922 92.094745 18 0.878883513 93.1058446 20 0.776294655 93.9105741
[0077] Table 2 40℃ static weight loss evaluation results
[0078] Concentration (ppm) Corrosion rate (mm / a) Corrosion inhibition efficiency (%) 0 13.2588828 0 1 8.894761462 32.9146988 5 1.474959845 88.8756853 10 1.307672355 90.1373866 15 1.061305178 91.9955158 18 0.930905999 92.9790012 20 0.868675252 93.4483526
[0079] Table 3 50℃ static weight loss evaluation results
[0080]
[0081]
[0082] Table 4 60℃ static weight loss evaluation results
[0083] Concentration (ppm) Corrosion rate (mm / a) Corrosion inhibition efficiency (%) 0 16.81599705 0 1 11.84203112 29.578775 5 3.133234751 81.3675351 10 2.975796178 82.3037779 15 1.563352456 90.7031831 18 1.215349499 92.7726587 20 1.176970846 93.0008857
[0084] Figure 1These are the weight loss test results of A3 carbon steel in 0.5M HCl solution with different concentrations of corrosion inhibitor (Example 1) added at 30°C, 40°C, 50°C and 60°C.
[0085] From the above data, it can be observed that the corrosion inhibition efficiency increases with the increase of concentration, but decreases with the increase of temperature, reaching about 93% at 20ppm, which indicates that the corrosion inhibitor forms a protective film on the metal surface, thereby slowing down the corrosion rate of the metal.
[0086] The above shows and describes the basic principles and main features of the present invention and the advantages of the present invention. It should be understood by those skilled in the art that the present invention is not limited to the above embodiments. The above embodiments and descriptions are only for explaining the principles of the present invention. Without departing from the spirit and scope of the present invention, the present invention may have various changes and improvements, which fall within the scope of the present invention to be protected. The scope of protection of the present invention is defined by the attached claims and their equivalents.
Claims
1. A bio-based gemini quaternary ammonium salt compound, characterized in that: The bio-based gemini quaternary ammonium salt compound is a compound having the structural formula shown in Formula I; Among them, R 1 One selected from cyclohexanone, cyclopentanone, acetone, 2-octanone, and 2-pentanone; R 2 Select except C 19 , C 21 C4~C 24 alkyl; X is a halogen, and the halogen is selected from at least one of Cl, I, and Br.
2. The method for preparing the bio-based gemini quaternary ammonium salt compound according to claim 1, characterized in that: Using 5-hydroxymethylfurfural (5-HMF) as a raw material, a compound having a gemini quaternary ammonium salt functional group and an alkyl long chain is constructed, comprising the following steps: (1) adding 5-HMF and ketone into solvent I to react and obtain an intermediate product after condensation; (2) adding the condensed intermediate product and the halogenation reagent into solvent II for reaction to obtain a halogenated intermediate product; (3) Adding the halogenated intermediate product and the amine compound into solvent III for reaction to obtain the bio-based gemini quaternary ammonium salt compound.
3. The method for preparing the bio-based gemini quaternary ammonium salt compound according to claim 2, characterized in that: The ketone in step (1) is one of cyclohexanone, cyclopentanone, acetone, 2-octanone and 2-pentanone, and the solvent I is methanol.
4. The method for preparing the bio-based gemini quaternary ammonium salt compound according to claim 2, characterized in that: In the step (1), the molar ratio of 5-HMF to ketone is 2:1, the reaction temperature is 0° C. to 30° C., and the reaction time is 0.5 to 12 h.
5. The method for preparing the bio-based gemini quaternary ammonium salt compound according to claim 2, characterized in that: The halogenating agent in step (2) is selected from at least one of thionyl chloride, phosphorus oxychloride, concentrated hydrochloric acid, iodobenzene and phosphorus tribromide, and the solvent II is selected from at least one of dichloromethane and dichloroethane.
6. The method for preparing the bio-based gemini quaternary ammonium salt compound according to claim 2, characterized in that: In the step (2), the molar ratio of the intermediate product after condensation to the halogenating agent is 1:2, the reaction temperature is 0° C. to 30° C., and the reaction time is 0.5 to 12 h.
7. The method for preparing the bio-based gemini quaternary ammonium salt compound according to claim 2, characterized in that: The solvent III in step (3) is selected from at least one of acetonitrile and dichloroethane, and the structural formula of the amine compound is as follows: Where R 2 Select except C 19 , C 21 C4~C 24 of alkyl.
8. The method for preparing the bio-based gemini quaternary ammonium salt compound according to claim 7, characterized in that: The amine compound in step (3) is selected from at least one of N,N-dimethylbutylamine, N,N-dimethyloctylamine, N,N-dimethyldodecylamine and N,N-dimethylhexadecylamine.
9. The method for preparing the bio-based gemini quaternary ammonium salt compound according to claim 2, characterized in that: In the step (3), the molar ratio of the halogenated intermediate product to the amine compound is 1:2, the reaction temperature is 60° C. to 100° C., and the reaction time is 0.5 to 12 h.
10. Use of the bio-based gemini quaternary ammonium salt compound according to claim 1 as a corrosion inhibitor.
Citation Information
Cited By
Composite film for manufacturing container liquid bag and preparation process
CN120921788A
Aromatic diol compounds, diepoxide compounds, polymers prepared from such compounds, and methods for producing them
JP2023549497A