CN114773234A - Synthesis method of 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid - Google Patents
Synthesis method of 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid Download PDFInfo
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- CN114773234A CN114773234A CN202210589758.8A CN202210589758A CN114773234A CN 114773234 A CN114773234 A CN 114773234A CN 202210589758 A CN202210589758 A CN 202210589758A CN 114773234 A CN114773234 A CN 114773234A
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- perfluorohexylsulfonyl
- dimethylamine
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- butyric acid
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- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 title claims abstract description 76
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title claims abstract description 23
- 238000001308 synthesis method Methods 0.000 title abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 31
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 23
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 9
- -1 perfluoroalkyl sulfonyl fluoride Chemical compound 0.000 claims abstract description 8
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 5
- 239000003112 inhibitor Substances 0.000 claims abstract description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003350 kerosene Substances 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 11
- 239000002699 waste material Substances 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 39
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 12
- 239000002994 raw material Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 5
- 101100006584 Mus musculus Clnk gene Proteins 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 239000003595 mist Substances 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HSDJWNJDPDJOEV-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O HSDJWNJDPDJOEV-UHFFFAOYSA-N 0.000 description 1
- YYXWJNBPHDUWJP-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)F YYXWJNBPHDUWJP-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 150000001265 acyl fluorides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GSJWYIDMIRQHMV-UHFFFAOYSA-N butanoyl fluoride Chemical compound CCCC(F)=O GSJWYIDMIRQHMV-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009854 hydrometallurgy Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000010587 phase diagram Methods 0.000 description 1
- UDYXGZXUMUTLSW-UHFFFAOYSA-M potassium;2,2,3,3,4,4,4-heptafluorobutanoate Chemical compound [K+].[O-]C(=O)C(F)(F)C(F)(F)C(F)(F)F UDYXGZXUMUTLSW-UHFFFAOYSA-M 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of chemical synthesis, and discloses a method for synthesizing 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid, which comprises the following steps: step one, synthesis of N- (2- (dimethylamine) -ethyl) -perfluorohexyl sulfonamide: obtained by reacting perfluoroalkyl sulfonyl fluoride with N, N-dimethyl-1, N-alkyl diamine under the catalysis of triethylamine; step two, synthesis of 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid: the compound is obtained by reacting N- (2- (dimethylamine) -ethyl) -perfluorohexyl sulfonamide with alkylic acid by using water as a solvent and p-methoxyphenol as a polymerization inhibitor. The synthesis method disclosed by the invention is simple in process, high in yield, green and environment-friendly, and in the synthesis process, water is used as a solvent in the step two, so that three wastes are not generated, and the synthesis method is very suitable for popularization and application in the industry.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to a synthesis method of 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid.
Background
4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid is an acid mist inhibitor with excellent effect, is mainly applied to the hydrometallurgy industry and is used for inhibiting acid mist generated by mineral flotation and metal extraction, thereby achieving green and environment-friendly production and being beneficial to the health of people.
At present, other simpler (no substituent or few substituents) synthesis methods of perfluorobutyric acid mainly comprise the steps of carrying out alkaline hydrolysis on corresponding perfluorobutyryl fluoride in a potassium hydroxide aqueous solution to obtain potassium perfluorobutyrate, and then acidifying with concentrated sulfuric acid to obtain perfluorobutyric acid. However, the preparation method needs strong acid and strong base, certain potential safety hazard exists in the production process, and the yield and the purity of the prepared corresponding perfluorobutyric acid are not ideal. However, the 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid synthesized by the method has more substituents and does not have the corresponding butyryl fluoride, so that the method is not suitable for alkaline hydrolysis/acidification, and the method for synthesizing the 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid is urgently needed to be developed, is green, environment-friendly and clean, does not generate three wastes, and is suitable for the production and development of future chemical products.
No other synthesis process of 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid is known in the prior art. The technical scheme is a synthetic route designed based on the structural characteristics of the product, and the structural characteristics of the product are determined according to the acid mist inhibition effect of the product and the water solubility (hydrophilic group) of the product.
The synthesis of the product also considers that the corresponding acyl fluoride is synthesized firstly and then is prepared by conventional alkaline hydrolysis/acidification, but the process is complex, the yield and the purity of the product are not ideal, and certain potential safety hazard exists, so the process is finally selected for synthesis.
The technical scheme has a lot of difficulties in the research and development process, particularly, the selection of the reaction solvent in the second step starts to select a non-water-soluble solvent (such as toluene), the solvent is distilled and then water is added to prepare a product with standard concentration after the reaction is finished, the concentration time of the method is longer, the product color is darker, impurities are generated, the product has certain loss during concentration, a small amount of residual toluene always exists, and the comprehensive quality of the product is poorer. Through continuous exploration, water is finally selected as a solvent, so that the synthesis process is simplified, the quality and yield of the product are greatly improved, the product has a light appearance color, and toxic toluene is not contained. The synthesis process of the product is green and environment-friendly, and the product is also green and environment-friendly, so that the product can serve multiple purposes.
Disclosure of Invention
The invention aims to provide a synthesis method of 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid, which is different from other simpler (no substituent or few substituents) synthesis methods of perfluorobutyric acid and solves the problems of the prior art that the yield and the purity of other organic acids such as butyric acid are not ideal, the process is complicated and certain potential safety hazard exists.
In order to achieve the purpose, the invention adopts the following technical scheme: a method for synthesizing 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid comprises the following steps:
step one, synthesis of N- (2- (dimethylamine) -ethyl) -perfluorohexyl sulfonamide: the catalyst is obtained by reacting perfluoroalkyl sulfonyl fluoride with N, N-dimethyl-1, N-alkyl diamine under the catalysis of triethylamine;
step two, synthesis of 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid: the compound is obtained by reacting N- (2- (dimethylamine) -ethyl) -perfluorohexyl sulfonamide with alkylic acid by using water as a solvent and p-methoxyphenol as a polymerization inhibitor.
The principle and the advantages of the scheme are as follows: the technical scheme adopts a two-step synthesis method to prepare the 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid, and the reaction formula of the preparation process is as follows:
the beneficial effects of this technical scheme lie in:
1. the technical scheme provides a novel method for synthesizing 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid, and provides a novel direction for synthesizing a novel product with high added value.
2. The synthesis method of the technical scheme has the advantages of simple process, high yield and environmental protection, and in the synthesis process, water is used as a solvent in the step two, so that three wastes are not generated, and the method is very suitable for popularization and application in the industry.
The key factors influencing the yield and the purity of the 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid in the scheme are the selection of raw material ratio, reaction temperature, reaction time and solvent.
Preferably, as a modification, in the first step, the solvent for the reaction is n-hexane, mineral spirit, toluene, kerosene or dichloromethane.
In the technical scheme, the solvent used in the step one is preferably normal hexane, solvent naphtha, toluene, kerosene or dichloromethane, so that the toxicity is low, and the harm to human bodies can be reduced.
Preferably, as an improvement, perfluoroalkanesulfonyl fluoride CnF(2n+1)In the SOFF, n is any integer in the range of 2-12.
In the technical scheme, the alkyl in the raw material perfluoroalkyl sulfonyl fluoride comprises any one of ethyl to dodecyl, the range of n can influence the product performance and the environment, and the larger the value of n is, the more F is contained, the larger the damage to the ozone layer in the atmosphere is; the n value is too small, the boiling point of the product is low, and the product is volatile.
Preferably, as an improvement, N, N-dimethyl-1, N-alkanediamine (CH3)2N-CnH2nin-NH 3, n is any integer in the range of 2 to 12.
In the technical scheme, the alkyl in the raw material N, N-dimethyl-1, N-alkyl diamine comprises any one of ethyl to dodecyl, the range of N can influence the product performance, the N value is too large, the product viscosity is large, the water solubility is poor, the N value is too small, the product boiling point is low, and the product is volatile.
Preferably, as a refinement, in step one, the molar ratio of N, N-dimethyl-1, N-alkanediamine to perfluoroalkanesulfonyl fluoride is 1-2: 1.
In the technical scheme, the molar ratio of the N, N-dimethyl-1, N-alkyl diamine to the perfluoroalkyl sulfonyl fluoride has an important influence on the reaction effect, and the addition of the N, N-dimethyl-1, N-alkyl diamine is too little, so that the reaction of the main raw material perfluoroalkyl sulfonyl fluoride is incomplete; excessive addition of N, N-dimethyl-1, N-alkanediamine results in waste of the raw material and increased product cost.
Preferably, as a modification, in the first step, the reaction temperature is 10 to 80 ℃.
In the technical scheme, the reaction temperature has important influence on the reaction effect and the product performance, and the excessive reaction temperature can increase impurities and make the product darker in color; the product performance is affected by incomplete reaction of raw materials due to too low reaction temperature.
Preferably, as a refinement, in step two, the molar ratio of alkenoic acid to N- (2- (dimethylamine) -ethyl) -perfluorohexylsulfonamide is from 1 to 2: 1.
In the technical scheme, the molar ratio of the 3-butenoic acid to the N- (2- (dimethylamine) -ethyl) -perfluorohexyl sulfonamide has important influence on the reaction effect and the product performance, and the reaction of the intermediate N- (2- (dimethylamine) -ethyl) -perfluorohexyl sulfonamide cannot be finished due to the addition of too little 3-butenoic acid; too much 3-butenoic acid is added, so that too much 3-butenoic acid is remained in the product, and the product performance is influenced.
Preferably, as a modification, in the second step, the reaction temperature is 60 to 120 ℃.
In the technical scheme, the reaction temperature has important influence on the reaction effect and the product performance, the reaction temperature is too high, impurities are increased, and the product color is darker; the product performance is affected by incomplete reaction of raw materials due to too low reaction temperature.
Preferably, as an improvement, in the first step, the crude N- (2- (dimethylamine) -ethyl) -perfluorohexylsulfonamide is refined after the catalytic reaction is completed.
According to the technical scheme, the N- (2- (dimethylamine) -ethyl) -perfluorohexylsulfonyl amide crude product prepared in the first step is refined, so that the purity and yield of 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid prepared in the later stage can be ensured.
Preferably, as an improvement, the alkenoic acid CH2＝CnH2nin-COOH, n is an integer in the range of 1 to 10.
In the technical scheme, the value range of n has important influence on the product performance, and the overlarge value range of n can cause large viscosity and poor water solubility of the product; and the value range of n is too small, so that the product has low boiling point and is volatile.
Detailed Description
The following is a detailed description of the embodiments, but the embodiments of the present invention are not limited thereto. Unless otherwise specified, the technical means used in the following embodiments are conventional means well known to those skilled in the art; the experimental methods used are all conventional methods; the materials, reagents and the like used are commercially available.
Example 1
A method for synthesizing 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid comprises the following steps:
step one, synthesis of N- (2- (dimethylamine) -ethyl) -perfluorohexyl sulfonamide: adding 0.1mol (8.8g) of N, N-dimethyl-1, 2-ethylenediamine, 0.05-0.1 mol (5.05-10.1 g) of triethylamine and 100-200 ml of N-hexane into a 500ml clean and dry four-neck flask, dropwise adding 0.1mol (40.2g) of perfluorohexylsulfonyl fluoride at 0-30 ℃, carrying out heat preservation reaction at 10-80 ℃ for 5-15 h after dropwise adding, cooling to room temperature, adding a proper amount of water, stirring for 0.5-2 h, carrying out suction filtration (centrifugal) drying, and obtaining the intermediate N- (2- (dimethylamine) -ethyl) -perfluorohexylsulfonamide.
And step two, adding 0.1mol (47g) of N- (2- (dimethylamine) -ethyl) -perfluorohexylsulfonamide, 0.0005-0.001 mol (0.062-0.124 g) of p-methoxyphenol and a proper amount of tap water into a 250ml clean dry four-mouth bottle, heating to 60-90 ℃, dropwise adding 0.1mol (8.6g) of 3-butenoic acid, reacting at 60-120 ℃ for 5-15 h after dropwise adding, cooling to room temperature, adding a proper amount of water, and stirring for 0.5-2 h to obtain the product 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid. According to the liquid phase diagram and the performance test effect, the generation of the substance is proved (the retention time is matched with that of a standard substance).
Examples 1 to 6 are examples of the present invention, comparative examples 1 to 4 are comparative examples of the present invention, each example and comparative example are different from example 1 in the selection of some parameters, and the detailed design of the specific examples and comparative examples is shown in the following table. Wherein the molar ratio of A to B refers to the molar ratio of N, N-dimethyl-1, N-alkanediamine to perfluoroalkanesulfonyl fluoride (main raw material); the molar ratio of C to D refers to the molar ratio of 3-butenoic acid to N- (2- (dimethylamine) -ethyl) -perfluorohexyl sulfonamide (intermediate).
TABLE 1
The yield and purity of 4- (N- (2- (dimethylamino) ethyl) -perfluorohexylsulfonyl) butyric acid (or the corresponding acid obtained by changing the raw material in the examples) prepared in the above examples and comparative examples were measured by the liquid phase method, and the results are shown in Table 2, wherein the purity was measured by repeating the experiment three times for each group. As can be seen from the data in Table 2, the yield and purity of the 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid prepared by the embodiments of the invention are both above 90%, and the acid mist inhibition rate can also reach above 90% through practice verification; in the comparative example, factors such as the molar ratio of raw materials, the types of solvents and the like in the reaction process have certain influence on the yield and the purity of the target product.
TABLE 2
The foregoing is merely an example of the present invention and common general knowledge in the art of designing and/or characterizing particular aspects and/or features is not described in any greater detail herein. It should be noted that, for those skilled in the art, without departing from the technical solution of the present invention, several variations and modifications can be made, which should also be regarded as the protection scope of the present invention, and these will not affect the effect of the implementation of the present invention and the practicability of the patent. The scope of the claims of the present application shall be determined by the contents of the claims, and the description of the embodiments and the like in the specification shall be used to explain the contents of the claims.
Claims (10)
1. A method for synthesizing 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid is characterized by comprising the following steps:
step one, synthesis of N- (2- (dimethylamine) -ethyl) -perfluorohexyl sulfonamide: obtained by reacting perfluoroalkyl sulfonyl fluoride with N, N-dimethyl-1, N-alkyl diamine under the catalysis of triethylamine;
step two, synthesis of 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid: the compound is obtained by reacting N- (2- (dimethylamine) -ethyl) -perfluorohexyl sulfonamide with alkylic acid by using water as a solvent and p-methoxyphenol as a polymerization inhibitor.
2. The method of claim 1 for synthesizing 4- (N- (2- (dimethylamino) ethyl) -perfluorohexylsulfonyl) butyric acid, wherein: in the first step, the solvent for the reaction is n-hexane, solvent oil, toluene, kerosene or dichloromethane.
3. The method of claim 2 for synthesizing 4- (N- (2- (dimethylamino) ethyl) -perfluorohexylsulfonyl) butyric acid, wherein: the perfluoroalkyl sulfonyl fluoride CnF(2n+1)In the SOFF, n is any integer in the range of 2-12.
4. The method of claim 3 for the synthesis of 4- (N- (2- (dimethylamino) ethyl) -perfluorohexylsulfonyl) butyric acid comprising the steps of: the N, N-dimethyl-1, N-alkanediamine (CH3)2N-CnH2nin-NH 3, n is any integer in the range of 2 to 12.
5. The method of claim 4, wherein the synthesis of 4- (N- (2- (dimethylamino) ethyl) -perfluorohexylsulfonyl) butyric acid comprises the steps of: in the first step, the molar ratio of the N, N-dimethyl-1, N-alkanediamine to the perfluoroalkyl sulfonyl fluoride is 1-2: 1.
6. The method of claim 5, wherein the synthesis of 4- (N- (2- (dimethylamino) ethyl) -perfluorohexylsulfonyl) butyric acid comprises the steps of: in the first step, the reaction temperature is 10-80 ℃.
7. The method of claim 6, wherein the synthesis of 4- (N- (2- (dimethylamino) ethyl) -perfluorohexylsulfonyl) butyric acid comprises the steps of: in step two, the molar ratio of the alkaleic acid to the N- (2- (dimethylamine) -ethyl) -perfluorohexyl sulfonamide is 1-2: 1.
8. The method of claim 7, wherein the synthesis of 4- (N- (2- (dimethylamino) ethyl) -perfluorohexylsulfonyl) butyric acid comprises the steps of: in the second step, the reaction temperature is 60-120 ℃.
9. The method of claim 8, wherein the synthesis of 4- (N- (2- (dimethylamino) ethyl) -perfluorohexylsulfonyl) butyric acid comprises the steps of: in the first step, after the catalytic reaction is finished, the crude N- (2- (dimethylamine) -ethyl) -perfluorohexyl sulfonamide is refined.
10. The method of claim 9, wherein the synthesis of 4- (N- (2- (dimethylamino) ethyl) -perfluorohexylsulfonyl) butyric acid comprises the steps of: said alkenoic acid CH2＝CnH2nin-COOH, n is an integer in the range of 1 to 10.
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| CN202210589758.8A CN114773234A (en) | 2022-05-26 | 2022-05-26 | Synthesis method of 4- (N- (2- (dimethylamine) ethyl) -perfluorohexylsulfonyl) butyric acid |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5144069A (en) * | 1990-12-13 | 1992-09-01 | Minnesota Mining And Manufacturing Company | Process for the preparation of fluoroaliphatic aminocarboxylate surfactants |
| US20030139550A1 (en) * | 1999-10-27 | 2003-07-24 | 3M Innovative Properties Company | Fluorochemical sulfonamide surfactants |
| CN105017097A (en) * | 2015-07-07 | 2015-11-04 | 武汉市化学工业研究所有限责任公司 | Preparation method for surfactant N-carboxyethyl, N-3-dimethylaminopropyl-perfluoro hexyl sulfonamide |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5144069A (en) * | 1990-12-13 | 1992-09-01 | Minnesota Mining And Manufacturing Company | Process for the preparation of fluoroaliphatic aminocarboxylate surfactants |
| US20030139550A1 (en) * | 1999-10-27 | 2003-07-24 | 3M Innovative Properties Company | Fluorochemical sulfonamide surfactants |
| US20030139549A1 (en) * | 1999-10-27 | 2003-07-24 | 3M Innovative Properties Company | Fluorochemical sulfonamide surfactants |
| CN105017097A (en) * | 2015-07-07 | 2015-11-04 | 武汉市化学工业研究所有限责任公司 | Preparation method for surfactant N-carboxyethyl, N-3-dimethylaminopropyl-perfluoro hexyl sulfonamide |
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