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Bistrifluoromethanesulfonimide CAS 82113-65-3

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  • Appearance: Colorless liquid
  • Purity: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: Bistrifluoromethanesulfonimide Supplier & Manufacturer

Basic Info

What is Bistrifluoromethanesulfonimide?

Bistrifluoromethylsulfonimide is a colorless needle-like crystal at room temperature, easy to absorb water and soluble in water, alcohols, acetone, ethers, insoluble in n-hexane, benzene, etc. It fumes in the air and easily Sublimation, with strong acidity and certain toxicity, needs to be well protected during synthesis and use.

Bistrifluoromethylsulfonimide is the most basic substance in perfluoroalkylsulfonimide (PFSI). Perfluoroalkylsulfonylimide, commonly known as “perfluoronitrogen superacid”, is a new type of superacid and a strong Bronsted acid. The main function of bistrifluoromethanesulfonimide is mostly determined by its properties as a “superacid” (such as strong acidity in gas phase or aqueous solution), which in turn is related to its anion part (CF3SO2)2N The structural characteristics of – are inseparable: First, under the synergistic effect of the perfluoroalkyl group with a strong electron-pulling effect, the negative charge on the N atom will disperse to the entire O-S-N skeleton through resonance to produce a high degree of delocalization, thereby greatly enhancing The stability of the anion; secondly, the two bulky perfluoroalkyl groups have a large steric hindrance effect and a strong electron pulling effect, so that the coordination ability of the ion is also greatly weakened.

Glyceryl trioleate is used as an emulsifier, conflation stabilizer, and wetting down agent in food and cosmetics, and the content of triolein in Ganoderma lucidum spores is fairly high. Ganoderma lucidum spores contain a fairly high content of adipose o il painting, about 20 to 30 Ganoderma lucidum spore oil painting can be attained by birth. Ganoderma lucidum spore oil painting substantially contains adipose acid esters, and also contains sterols, which has the same effect as Ganoderma lucidum spores. 1,2- oleic acid-3-palmitic triglyceride and glyceryl trioleate are the two factors with the loftiest content in Ganoderma lucidum spore oil painting.

Bistrifluoromethanesulfonimide Uses

  1. Trifluoromethanesulfonylimide is a strong acid used to prepare efficient Lewis acid catalysts.
  2. It can be used to improve the efficiency of graphene/silicon Schottky solar cells through chemical doping, and as a solvent for recycling battery electrodes.
  3. Trifluoromethanesulfonylimide can be used as a catalyst for the preparation of 1-substituted-1H-1,2,3,4-tetrazole.
  4. Bis (trifluoromethane) sulfonic imide (TFSI, Tf 2 N) is used as an anionic substance to form a molten salt of 1-ethyl-3-methylimidazolium. It undergoes acid-base complexation with rod-shaped polymers (2,5-pyridine), providing highly ordered layered self-assembly in hydrated films.

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Application of Bistrifluoromethanesulfonimide

At present, the most important and widest applications of bistrifluoromethylsulfonimide mainly include: replacing traditional Bronsted acid and Lewis acid as efficient catalysts in some important organic chemical reactions; synthesizing environmentally friendly ionic liquids, in As a green solvent that can be recycled in the reaction system; as an important raw material for the synthesis of high-efficiency electrolytes for lithium-ion batteries – lithium bistrifluoromethanesulfonyl imide.

Trifluoromethanesulfonimide has good catalytic properties for some organic reactions, on the one hand because of the weak coordination of anion and cation in the molecule, on the other hand because trifluoromethanesulfonimide anion is simultaneously Very good electrophilic and nucleophilic leaving groups. When it is used as a catalyst, fluorosulfonimide anion is usually reacted with related cations to prepare ionic liquid, or it is immobilized on a series of supports such as silica by sol method, gel method, etc., so as to prepare solid acid catalyst and Participate in the reaction.

  • Diels-Alder reaction
    Common metal salts of trifluoromethanesulfonimides are far superior to other conventional Lewis acids in the Diels-Alder reaction. In the 1990s, it was discovered that LiNTF2 has a good catalytic effect on the Diels-Alder reaction between some α, β-unsaturated nitrogen-containing compounds and some dienophiles. Ytterbium trifluoromethanesulfonimide has excellent catalytic performance in the addition reaction of cyclopentadiene and naphthoquinone diene in toluene.
  • Friedel-Crafts acylation reaction
    Bistrifluoromethanesulfonimide can efficiently catalyze the acetylation of phenetole, diphenyl ether and benzoyl chloride. During the reaction, in the presence of acetonitrile at 70°C, after 2 hours of reaction, 95% of anisole can be converted into methoxyacetophenone, and the selectivity based on anisole is as high as 98%.
  • Esterification reaction
    It has been tried to use perfluoronitrogen superacid complexes to catalyze some esterification reactions in the laboratory for a long time and achieved good results. The prepared polymer copolymer with abundant porosity, polystyrene-diethylene-supported perfluoroalkylsulfonimide, is used to catalyze the esterification reaction of lauric acid and ethanol, and the conversion rate can reach 93%-95%. The condensation reaction of resorcinol and ethyl acetoacetate was catalyzed at 140 ° C, and the yield was 88% to 91%, which proved that its catalytic stability was still good at higher temperatures.
  • Catalyze the nitration reaction of aromatic compounds and other partial organic reactions
    Perfluoroalkylsulfonylimide salts have nitrating properties for toluene, which are much better than traditional catalysts in terms of catalytic efficiency and catalyst usage. Lithium bistrifluoromethanesulfonylimide and its homologous compounds are used as Lewis acids with high catalytic activity. Catalytic effect in organic catalytic cracking, hydrocracking, catalytic reforming, isomerization, olefin hydration, toluene disproportionation, alcohol dehydration and acylation.

Bistrifluoromethanesulfonimide ion [(CF3SO2)2N-, TFSI-] is often selected as anion in ionic liquids, because the strong electron-pulling property of its perfluoroalkyl group can effectively disperse the negative charge in the ion and reduce the The Coulomb interaction between anions and cations expands the liquid range of the system. At the same time, TFSI- has a lower lattice energy, which can significantly reduce the melting point of the system. Therefore, many room temperature molten salt electrolyte systems are established based on the LiTFSI system.

Several bistrifluoromethylsulfonimide ionic liquids were synthesized with N-methylimidazole and pyridine as cations. The ionic liquid was used as a catalyst and H2O2 with a mass fraction of 35% was used as an oxidant to investigate the effect of this system on the simulated oil containing The oxidative extraction ability of the sulfur compound thiophene has achieved good results, and the desulfurization rate can reach about 65%.

Lithium bistrifluoromethanesulfonimide has the following characteristics: high electrical conductivity, which is equivalent to LiPF6, the mainstream lithium battery electrolyte in the market; high thermal stability, with a melting point of 236°C and a decomposition temperature of 360°C ℃; the electrochemical properties are stable. When Ag+/Ag is used as the reference electrode, its anti-oxidation limit in EC/DMC reaches 2.5V, and when it is replaced with Li+/Li reference electrode, it reaches 5.0V[16]. The discharge cycle morphology is superior to other lithium salt electrolytes. If the corrosion problem of the aluminum sheet under high voltage conditions is solved, it will be one of the high-efficiency lithium battery electrolyte materials with great potential. With the vigorous promotion and rapid development of electronic products and electric vehicles, the market demand and performance requirements for lithium batteries are increasing day by day. The purity of bistrifluoromethanesulfonimide as the core component of the electrolyte is a key factor in determining battery performance. Therefore, how to industrially prepare high-purity bistrifluoromethanesulfonimide has become a very popular and urgent issue. subject.

Reference

  1. Bistriflimide – WikiPedia
  2. Research progress on the production and application of bistrifluoromethanesulfonimide

Bistrifluoromethanesulfonimide Supplier and Manufacturer

As a bistrifluoromethanesulfonimide supplier and manufacturer with a strict standard product quality system certificate, Zhishang Chemical has long been providing the best bistrifluoromethanesulfonimide raw materials to customers all over the world.

Over the years, relying on professional team experience and customer-centric team concept to meet customer needs in a timely manner, our company enjoys a high reputation in the world. At present, our company has served more than 6,000 customers and has established long-term cooperative relations with customers from many countries.

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