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Tetrabutylammonium hydrogen sulfate (TBAHs), molecular formula C16H37NO4S, CAS 32503-27-8, White to off white crystals, belonging to quaternary ammonium salts, have similar properties to inorganic salts, are easily soluble in water, and aqueous solutions can conduct electricity. Can be used as surfactants, catalysts, emulsifiers, disinfectants, fungicides, anti-static agents, etc. Buffer salt systems are commonly used as aqueous mobile phases in reverse phase liquid chromatography detection. For some compounds with special structures that are difficult to separate, they often produce excellent separation effects.
It can be used together with potassium fluoride dihydrate to synthesize β - fluoroamine derivatives through the ring opening reaction of nitrogen heterocyclic propane. It can also be used as a catalyst to hydrolyze aziridines and epoxides into the corresponding β - amino alcohols and 1,2-diols, respectively. It is a phase transfer catalyst used in organic synthesis chemistry such as halogen displacement reactions, oxidation-reduction reactions, N-alkylation, dichlorocarbene reactions, and can also be used as a reagent for high-performance liquid chromatography analysis.
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Chemical Formula |
C16H37NO4S |
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Exact Mass |
339 |
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Molecular Weight |
440 |
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m/z |
339 (100.0%), 340 (17.3%), 341 (4.5%), 341 (1.4%) |
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Elemental Analysis |
C, 56.60; H, 10.98; N, 4.13; O, 18.85; S, 9.44 |
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Tetrabutylammonium Hydrogen Sulfate (TBAHS) is an important chemical compound with unique physical and chemical properties and a wide range of applications. In the field of chemical engineering, it is widely used in various aspects such as catalysts, solvents, ionic liquids, etc. due to its excellent catalytic performance, solubility, and stability.
Application as a catalyst
1. Phase transfer catalyst
Catalytic principle: It is an efficient phase transfer catalyst that can promote the transfer of substances between different phases in organic synthesis reactions, thereby accelerating the reaction process.
Application examples: As a phase transfer catalyst, it can significantly improve reaction rate and yield in halogen substitution reactions, oxidation-reduction reactions, N-alkylation reactions, and other reactions.
For example, in the hydrolysis reaction of aziridine and epoxides, it can catalyze the hydrolysis process and generate the corresponding β - amino alcohols and 1,2-diols.
2. Acid catalyst
Catalytic performance: It has a certain acidity and can be used as an acid catalyst to participate in various chemical reactions.
Application example: In the hydrogenation reaction of olefins, as an acid catalyst, it can promote the addition reaction of hydrogen gas, improve the efficiency and selectivity of hydrogenation reaction.
3. Reagents
Multifunctionality: It can also be used as a reagent to participate in certain specific chemical reactions, such as dichlorocarbene reactions.
Application example: In the dichlorocarbene reaction, it can react with dichlorocarbene to generate corresponding products, thereby expanding the application scope of the reaction.
Application as a solvent
1. Ionic liquid solvents
Excellent performance: It has excellent conductivity and thermal stability, and can be used as an ionic liquid in solvent systems for electrochemical, biochemical, and catalytic reactions.
Application example: In the field of electrochemistry, as an ionic liquid solvent, it can provide a good ion conductive environment and promote the progress of electrochemical reactions. In catalytic reactions, as a solvent, it can stabilize the catalyst and promote contact between reactants, thereby improving catalytic efficiency.
2. Reverse phase liquid chromatography mobile phase
Separation effect: Buffer salt systems are commonly used as aqueous mobile phases in reverse phase liquid chromatography detection, and can often produce excellent separation effects on compounds with special structures that are difficult to separate.
Application example: In the determination of oxalic acid in plant tissues and root exudates, as the aqueous mobile phase of reverse phase liquid chromatography, it can effectively separate and detect compounds such as oxalic acid.
Application as an ionic liquid
1. Electrochemical field
Conductivity: With excellent conductivity, it can be used as an ionic liquid in the field of electrochemistry, such as batteries, capacitors, etc.
Application example: In lithium-ion batteries, as an ionic liquid electrolyte, it can provide good ion conductivity, improve battery performance and stability.
2. Separation technology field
Extractant: Tetrabutylammonium hydrogen sulfate can be used as an extractant in liquid-liquid extraction processes, and due to its unique physical and chemical properties, it can selectively extract target compounds.
Membrane separation materials: They can also be used as membrane separation materials in gas or liquid separation processes to achieve selective separation of target compounds by adjusting the structure and properties of the membrane.
Other applications
1. Surfactants
Surface performance: It has certain surface activity, can reduce the surface tension of liquids, improve the wettability and dispersibility of liquids.
Application example: In the fields of cosmetics, detergents, etc., as a surfactant, it can improve the performance and stability of products.
2. Emulsifier
Emulsification performance: it has certain emulsification performance, can promote the emulsification process of oil-water mixture, and form a stable lotion.
Application example: In the fields of food, medicine, etc., as an emulsifier, it can improve the texture and taste of products.
3. Disinfectants and fungicides
Antibacterial performance: It has certain antibacterial properties and can inhibit or kill bacteria and other microorganisms.
Application examples: In the fields of healthcare, hygiene, etc., as a disinfectant or bactericidal agent, it can be used in processes such as instrument disinfection and environmental disinfection.
4. Antistatic agent
Anti static performance: It has a certain degree of anti-static performance, which can reduce the generation and accumulation of static electricity.
Application example: In the fields of plastics, rubber, etc., as an anti-static agent, it can improve the anti-static performance of products and enhance the safety of product use.
Tbahs chemical is widely used as a phase transfer catalyst. It can also be used as surfactant, catalyst, emulsifier, disinfectant, fungicide, antistatic agent and other reversed-phase high performance liquid chromatography to determine oxalic acid in plant tissue and root exudates, as a substance in the aqueous solution system. Specific application examples are as follows:
The main related substances include N-methyl impurity, impurity A, impurity B, impurity C, impurity D, and impurity E. The analytical method of related substances provided by the Chinese Pharmacopoeia, the European Pharmacopoeia and the United States Pharmacopoeia is reversed-phase liquid chromatography, with phenyl-bonded silica gel as the filler, and the mobile phase is acetonitrile-salt solution (take 0.5g of tetrabutylammonium hydrogen sulfat, 1g of potassium dihydrogen phosphate, add 500mL of water, add 2mL of phosphoric acid, dilute to 1000mL with water) (volume ratio: 30:70), the detection wavelength is 293nm, the flow rate is 1.3mL/min, the column temperature is 30 ℃, and the injection volume is 20 μ L. The mobile phase can effectively separate moxifloxacin and its impurities.
A high performance liquid chromatography method is used, and octadecylsilane bonded silica gel column is selected, and mobile phase A and mobile phase B are used for gradient elution, with a flow rate of 0.4-0.6mL/min, column temperature of 25-30 ℃, and detection wavelength of 220nm; The mobile phase A is tetrabutylammonium bisulfate buffer solution, dilute 20mL with water to 1000mL; The mobile phase B is tetrabutylammonium bisulfate buffer solution, dilute 20mL with water to 750mL, and add 240-260mL acetonitrile; The tetrabutylammonium bisulfate buffer solution is 8.5g tetrabutylammonium bisulfate. Add 80mL of water to dissolve, and then add 3.4mL of phosphoric acid. Finally, use 10mol/mL of sodium hydroxide solution to adjust the pH value to 7.3-7.7; The gradient elution is performed with mobile phase A and mobile phase B, time (min)/mobile phase B (v%): 0/0; 10/0; 35/100; 40/100; 41/0; 55/0. Compared with the prior art, the above detection method can significantly improve the retention performance, and has the characteristics of strong specificity, high sensitivity and good accuracy.
The main steps are as follows:
1) Select the analytical chromatographic conditions: ODS column (4.6mm × 25cm) or other equivalent chromatographic column, with wavelength of 250nm, flow rate of 1ml/min, column temperature of 25 ℃, and injection volume of 20ul;
2) Prepare the tetrabutylammonium bisulfate solution with deionized water to a molar concentration of 1.0~2.0mmol/L, and prepare the prepared tetrabutylammonium bisulfate solution and chromatographic grade methanol into mobile phase at a volume ratio of 60:40;
3) Dilute the sample to be tested to a concentration of 0.5%~2.0% by volume with organic solvent, and prepare the test solution;
4) Absorb the test solution with a microinjector, inject it into a high performance liquid chromatograph, and use the area external standard method for analysis;
5) Record the content of ammonium acetylsulfamate in the sample to be tested. The method can accurately and quickly determine the content of acetylsulfamate.
Alkyl halides as raw materials, potassium iodide and tetrabutylammonium bisulfate as catalysts, and potassium phosphate as base to obtain asymmetric benzyl alkyl disulfides. The method of the invention avoids using mercaptan with pungent odor as the sulfur source, and adopts microwave reaction technology and "one-pot method", which not only achieves the purpose of green environmental protection, but also simplifies the operation procedure and further reduces the cost of synthesis and large-scale production.
Which is composed of the following raw materials: 10-15 parts of hydroxychromium sulfate, 8-10 parts of chromium trichloride, 5-8 parts of cobalt nitrate, 3-5 parts of aluminum sulfate, 3-5 parts of potassium carbonate, 5-8 parts of potassium nitrate, 3-5 parts of ammonium chloride, 2-3 parts of octadecyl dimethyl benzyl ammonium chloride, 1-2 parts of tetrabutylammonium bromide, 2-3 parts of tetrabutylammonium bisulfate, 8-10 parts of hydrochloric acid, 5-8 parts of oxalic acid, 1-3 parts of sodium pyrophosphate, 2-3 parts of disodium dihydrogen pyrophosphate 2-3 parts of glycine, 3-4 parts of aminocaproic acid, 80-100 parts of deionized water.
The trivalent chromium electroplating solution only releases oxygen during the chromium plating process, which is clean and pollution-free. The coating has bright appearance, few cracks, good adhesion, rich raw material sources, low cost, excellent cost performance, good stability of the electroplating solution, and is conducive to its industrial promotion.
Method 1:
A method for synthesizing tetrabutylammonium bisulfate by aerosol method, including the following steps:
Step 1: mixing iodobutane and tributylamine into the reactor, adding acetonitrile as solvent, then heating and refluxing for 1h, cooling to room temperature, adding methyl bisulfate, refluxing for 8h, steaming out the byproduct iodobutane, then decompressing acetonitrile, and then ultrasonic fogging to obtain aerosol particles for standby;
Step 2: heat and react the standby aerosol particles in the inert gas environment at 100-200 ℃ to obtain pre-tetrabutylammonium bisulfate, and then put them in the hydrogen environment to heat and react at 150-250 ℃, and then wash them to obtain the tetrabutylammonium bisulfate of the invention.
Method 2:
Preparation of tetrabutylammonium hydrogen sulfate:
Add 100g of dichloroethane and 70g of tetrabutylammonium bromide into the three-mouth bottle equipped with distillation device, and then slowly add 21g of concentrated sulfuric acid. When dichloroethane is heated and distilled, a large amount of hydrogen bromide is taken out of the tail gas. After about 80g of dichloroethane is evaporated, 100g of dichloroethane is added to the three-mouth bottle. Repeat the distillation of dichloroethane, evaporate 170g of dichloroethane, remove the residual dichloroethane at 50 ℃ under reduced pressure, and add 60g of ethyl acetate to reflux 0 5h, cooling crystallization. The product is obtained by filtration, and the residual ethyl acetate is removed from the product under reduced pressure at 50 ℃ to obtain the product. The product is white crystal, the content is more than 99%, the weight is about 67g, and the yield is about 90%.
FAQ
What is the use of Tetrabutylammonium hydrogen sulphate?
Tetrabutylammonium hydrogen sulfate (TBAHS) is commonly used as a phase-transfer catalyst in the synthesis of pharmaceutical compounds. It enhances the reactivity and efficiency of chemical reactions.
What is another name for Tetrabutylammonium hydrogen sulfate?
Synonym(s): Tetrabutylammonium bisulfate, Tetrabutylammonium hydrogen sulfate, Tetra-n-butylammonium hydrogen sulfate. (CH3CH2CH2CH2)4N(HSO4)
What is TBAB used for?
A catalytic amount of TBAB is sufficient to catalyze various alkylation, oxidation, reduction, and esterification processes. It is also employed as an efficient co-catalyst for numerous coupling reactions. It has also acted as an efficient zwitterionic solvent in many organic transformations under molten conditions.
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