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Nonafluorobutanesulfonyl Fluoride CAS 375-72-4

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  • Appearance: Colorless liquid
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: Nonafluorobutanesulfonyl Fluoride Supplement

Basic Info of Nonafluorobutanesulfonyl Fluoride

What is Nonafluorobutanesulfonyl Fluoride?

Perfluorobutane sulfonyl fluoride (NFF) is a colorless and volatile liquid, which is immiscible with water, but soluble in ordinary organic solvents. It is valuable for palladium to catalyze the cross coupling reaction of sulfonates. As a perfluoroalkyl sulfonating agent, NFF has the advantages of lower cost and higher stability compared with the more commonly used trifluoromethylsulfonic anhydride. Fluoride leaving groups are easily replaced by nucleophiles such as amines. Phenolic salts and enols produce sulfonamides, aryl and alkenyl nonafluorosulfonic acids, respectively.

Perfluorobutylsulfonyl fluoride is a perfluorinated compound that is liquid at room temperature and is mainly used in the synthesis of fluorocarbon surfactants, fluorinated pesticides, dyes, and polycarbonate processing dispersants.

Compared with other deoxyfluorination reagents, perfluorobutylsulfonyl fluoride (PBSF) is a quicker, and other sulfonyl fluoride fluorination reagents may take hours or days to complete the reaction, but it can be completed in seconds. completed within.

Nonafluorobutanesulfonyl Fluoride Uses

  1. Nonafluorobutanesulfonyl fluoride is used in the synthesis of fluorocarbon surfactants, fluorinated pesticides, dyes, polycarbonate handling dispersants, etc.
  2. Antibacterial synergist, made use of in combination with sulfonamides to boost antibacterial result, likewise made use of for avian coccidiosis infection as well as digestive microbial infection.
  3. Nonafluorobutanesulfonyl fluoride can be made use of to synthesize a selection of fluorine-containing unique surfactants. Its potassium salt, potassium perfluorobutanesulfonate, is an outstanding anionic surfactant and also the most effective fire resistant for polycarbonate.
  4. Phenylalkynes are produced from O (trimethylsilyl) phenol by the domino process using nine fluorobutane sulfonyl fluoride (NFF).

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Application of Nonafluorobutanesulfonyl Fluoride

Perfluorobutylsulfonyl fluoride can be used as a catalyst for the fluorination reaction. For example, in the fluorination of 2-trichloromethyldichlorobenzyl, perfluorosulfonyl fluoride catalysts such as Butylsulfonyl fluoride, perfluoropentylsulfonyl fluoride, perfluorooctylsulfonyl fluoride, etc. have the advantages of safety and low toxicity, good catalytic selectivity, less dosage, and high fluorination yield.

Its specific operation is as follows: in a 5L stainless steel autoclave equipped with a stirrer and a thermometer, the temperature is lowered to below 5°C, and hydrogen fluoride and 2-trichloromethyl benzyl chloride are added successively, and the mass ratio of the two is 1:1, Then add the catalyst perfluorobutylsulfonyl fluoride, the amount of 2-trichloromethyl benzyl chloride and the catalyst is 1:0.01, the temperature is raised to 50~60°C, the reaction pressure is controlled to 0.8-1.2WPa, and the reaction is carried out for 4 hours. Sampling, GC detection, the content of the intermediate product 2-difluoro-chloromethyl benzyl chloride is 0.2%, the reaction finishes with nitrogen purging to remove excess hydrogen fluoride, neutralize with potassium carbonate aqueous solution to p=6~7, leave standstill, The product 2-trifluoromethyl dichlorobenzyl was isolated with a content of 97.5% and a yield of 93.5%. The reaction formula of this reaction is as follows.

Perfluorobutylsulfonyl fluoride and other components are mixed in a certain proportion to make anti-corrosion cutting fluid for auto parts. The specific components are: mixed vegetable oil 25 parts, tribasic lead sulfate 15 parts , 16 parts of succinate monoethoxylate sulfonate, 10 parts of sodium laureth sulfate, 20 parts of cocamidopropyl betaine, 20 parts of sodium sulfate, 15 parts of perfluorobutylsulfonyl fluoride, 18 parts of triethanolamine, 5 parts of citric acid, 15 parts of sodium petroleum sulfonate, 4 parts of fatty alcohol polyoxyethylene ether, 4 parts of p-nitrobenzoic acid, 2 parts of sodium tetraborate, 3 parts of dimethyl maleic anhydride, Some ionized water.

Fluorosurfactant is an indispensable substance in the emulsion polymerization of fluoromonomer. It not only has good emulsifying performance for fluoromonomer, but also stabilizes the emulsion performance of the product.

The steps of preparing perfluorobutylsulfonyl fluoride quaternary ammonium salt from perfluorobutylsulfonyl fluoride are as follows: Weigh a certain amount of ethylenediamine and isopropyl ether in a reaction flask, and slowly drop an equal amount of After the addition of perfluorobutylsulfonyl fluoride, the temperature was raised to 50 °C for 1 h. After cooling, wash twice with water, then heat and distill the light yellow solid of isopropyl ether solvent under low pressure, recrystallize with ethanol, vacuum dry to obtain white solid, weigh a certain amount of white solid into a three-necked flask, add dimethyl formamide, stir at room temperature to dissolve it completely, add equimolar maleic anhydride into the reaction flask, stir at room temperature for 0.5 h, then heat to 50 °C and stir for 1 h.

After cooling, pour it into distilled water for precipitation, filter to obtain a white solid product, dissolve the white solid product with NaOH solution, add glycidyl trimethyl ammonium chloride, heat and react to obtain a fluorine-containing quaternary ammonium salt type cationic surfactant.

Fluorinated polyether compounds have lower surface energy. The longer the perfluorocarbon chain, the better the water and oil repellency. However, the degradation process will produce perfluoroalkyl carboxylic acids and sulfonic acid compounds, which are difficult to further degrade. Environmentally hazardous, such as perfluorooctanoic acid and perfluorooctane sulfonic acid. The functional polymers containing short fluorocarbon chains can avoid the harm to the environment caused by the use of compounds containing long fluorocarbon chains.

Using perfluorobutylsulfonyl fluoride as raw material, intermediate 4 with terminal hydroxyl group was synthesized by sulfonylation and N alkylation, and then 2,2-dibromomethyloxetane (2) was combined with 4 The Williamson etherification of novel oxetane derivatives 1a and 1b containing pendant perfluorobutylsulfonamide groups was synthesized. The reaction scheme is as follows.

Prepartion of Nonafluorobutanesulfonyl Fluoride

  • Using butylsulfonyl chloride as the starting material, the butylsulfonyl chloride is easily prepared by fluorine replacement reaction with potassium chloride, etc., and then the butylsulfonyl fluoride is charged with anhydrous hydrogen fluoride. Electrolysis cell, electrolysis is carried out under normal pressure in nitrogen atmosphere, and the hydrogen in the alkyl group in butylsulfonyl fluoride is replaced with fluorine to generate perfluorobutylsulfonyl fluoride. The reaction formula is as follows.

  • Using tetrahydrothiophene-1,1-bicyclide as raw material, carry out electrofluorination reaction to generate perfluorobutylsulfonyl fluoride. The reaction formula is as follows.

Reference

  1. Nonafluorobutanesulfonyl Fluoride – WikiPedia
  2. Nonafluorobutanesulfonyl Fluoride – PubChem
  3. Fu Limin, Jia Tiecheng, Liu Guangsheng, A preparation method of 2-trifluoromethylbenzoic acid, CN 201310258354, application date 2013-06-26
  4. Bian Zijun. Study on the synthesis of perfluorobutylsulfonyl fluoride quaternary ammonium salt[J]. Contemporary Chemical Industry, 2008, 37(5): 484-486.

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