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Zinc trifluoromethanesulfonate is a white to light gray powder with the chemical formula C2F6O6S2Zn, CAS 54010-75-2, Easy to absorb moisture and highly soluble in water. This compound is composed of carbon (C), fluorine (F), oxygen (O), sulfur (S), and zinc (Zn), and the specific molecular formula shows the connection mode and proportion of each element. It is also soluble in various organic solvents. These solvents include but are not limited to methanol, ethanol, acetonitrile, etc. It can be used as a catalyst for the synthesis of disulfide ketone; Preferred reagents for Koenigs Knorr glycosylation method; Catalyst for the thioketylation reaction of ketones. It is an important inorganic compound with wide applications in catalysis, battery materials, synthesis intermediates, and metal surface treatment.
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Chemical Formula |
C2F6O6S2Zn |
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Exact Mass |
362 |
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Molecular Weight |
364 |
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m/z |
362 (100.0%), 364 (57.4%), 366 (38.6%), 365 (8.4%), 364 (4.5%), 364 (4.5%), 366 (2.6%), 366 (2.6%), 363 (2.2%), 368 (1.7%), 368 (1.7%), 368 (1.3%), 365 (1.2%), 364 (1.2%) |
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Elemental Analysis |
C, 6.61; F, 31.36; O, 26.41; S, 17.64; Zn, 17.99 |
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Zinc trifluoromethanesulfonate, is an inorganic compound with strong acidity, with an acid strength even exceeding 100% sulfuric acid, and is therefore considered a superacid. The product has a wide range of applications in various fields, including but not limited to chemical synthesis, plant growth regulation, catalytic reactions, and electronic materials.
Application in Chemical Synthesis
In the synthesis process of polymer materials, it can be used to regulate the properties of the materials. It can change the crystallinity of polymer materials, thereby affecting their properties such as hardness, transparency, and flexibility. This regulatory performance makes it widely used in the customized synthesis of polymer materials.
(1) Changing crystallinity: By adjusting its dosage and reaction conditions, the crystallinity of polymer materials can be precisely controlled. The change in crystallinity directly affects the physical and chemical properties of materials, such as hardness, toughness, heat resistance, etc.
(2) Customized performance: Based on specific needs, polymer materials with specific properties can be synthesized using it. For example, when high transparency materials are needed, reducing crystallinity can be achieved; When high-strength materials are needed, the goal can be achieved by increasing the crystallinity.
Plant growth regulators
It can also be used as a plant growth regulator. It can affect the growth and development process of plants, thereby improving their yield and quality.
(1) Promote plant growth
It can stimulate the division and elongation of plant cells, thereby promoting plant growth. This promoting effect is manifested in various plants, such as wheat, corn, cotton, etc. By applying an appropriate amount of this substance, plant height, leaf area, and biomass can be improved.
(2) Improve resilience
It can also improve the stress resistance of plants, including their ability to resist adversity such as drought, salinity, and low temperature. This is mainly due to its ability to regulate physiological and biochemical processes in plants, such as increasing antioxidant enzyme activity and reducing membrane lipid peroxidation. These physiological and biochemical changes help plants maintain normal growth and development under adverse conditions.
(3) Improve quality
During the fruit ripening process, it can affect indicators such as color, taste, and nutritional value of the fruit. By applying an appropriate amount of this compound, the quality of the fruit can be improved and the commercial value of the fruit can be increased. For example, when applied to fruit trees such as apples and pears, it can increase the sugar content and hardness of the fruit, improve its taste and storage resistance.
In a field experiment in a certain region, researchers found that applying an appropriate amount of the product can significantly improve the yield and quality of wheat. By measuring indicators such as plant height, leaf area, and biomass, researchers found that the treatment group treated with this compound showed significant improvement compared to the control group. In addition, the compound can also enhance the resistance of wheat to adversity such as drought and salinity, providing strong support for agricultural production.
Applications in Electronic Materials
It also has potential application value in the field of electronic materials. Due to its unique chemical structure and properties, it may be used as an additive for lithium-ion batteries or a modifier for polymer materials.In lithium-ion batteries, it may be used as an additive to improve battery performance. It can affect the electrolyte composition and structure inside the battery, thereby improving the charging and discharging efficiency and stability of the battery.
(1) Improving charging and discharging efficiency: By adding an appropriate amount of this substance to the electrolyte of lithium-ion batteries, the composition and structure of the electrolyte can be optimized, thereby improving the charging and discharging efficiency of the battery. This helps to reduce the charging time of the battery and improve its discharge capacity.
(2) Improving stability: It can also enhance the stability of lithium-ion batteries. During the continuous charging and discharging process of the battery, it can reduce the unstable reactions and degradation processes of internal chemical substances, thereby extending the service life of the battery and improving its safety.In the field of polymer materials, it can be used as a modifier to improve the properties of materials. By adding it to polymer materials, the crystallinity, melting point, and mechanical properties of the material can be altered.
A battery manufacturer added it as an additive to the electrolyte of lithium-ion batteries and found that the charging and discharging efficiency and stability of the battery were significantly improved. By testing indicators such as charging time, discharge capacity, and cycle life of the battery, the manufacturer found that the battery with the added compound had better performance compared to the battery without the added compound. This discovery provides new ideas and methods for the improvement and upgrading of lithium-ion batteries.
Other catalytic reactions
In addition to acylation and esterification reactions, it can also catalyze various other organic chemical reactions. For example, in the silanization reaction, the compound can act as a catalyst to promote the reaction between silane and alcohol compounds; In alkylation reactions, it can also catalyze the reaction between alkylating reagents and aromatic hydrocarbons. These catalytic properties make them widely applicable in the field of organic synthesis.
Polymer material modifier
(1) Changing crystallinity: As mentioned earlier, it can alter the crystallinity of polymer materials. By adjusting its dosage and reaction conditions, the crystallinity of the material can be precisely controlled, thereby affecting indicators such as hardness and transparency of the material.
(2) Raise melting point: It can also increase the melting point of polymer materials. This helps to broaden the temperature range of materials and improve their heat resistance. In some applications that require high temperature stability, this modification effect is particularly important.
(3) Improving mechanical properties: By adding an appropriate amount of zinc trifluoromethanesulfonate to polymer materials, the mechanical properties of the materials can also be improved. For example, it can improve the tensile strength and toughness of materials, making them more resilient and durable when subjected to external forces.
1. Dominant Laboratory Synthetic Route: Zinc Carbonate Neutralization Method (Preferred Process)
This route serves as the standard preparation protocol in organic synthesis laboratories, featuring mild reaction conditions without flammable or explosive by-products. The product purity and yield can both exceed 98%. The reaction equation is: ZnCO₃ + 2CF₃SO₃H → Zn(CF₃SO₃)₂ + CO₂↑ + H₂O.
Anhydrous methanol is adopted as an inert medium for the operation. Trifluoromethanesulfonic acid is added dropwise slowly into a methanolic suspension of Zn carbonate at room temperature under continuous stirring, with carbon dioxide bubbles steadily released throughout the dropping process. After dropwise addition completes, the mixture is stirred at ambient temperature for 20 minutes, then heated to reflux for 2 hours to ensure full consumption of Zn carbonate. The reaction endpoint is confirmed when all solids dissolve completely and no more bubbles evolve.
Once the reaction mixture cools to room temperature, filtration is performed to remove trace impurities. The filtrate is transferred to a rotary evaporator to remove methanol and generated water under reduced pressure, yielding crude off-white solids. The crude product is placed in a vacuum oven and dried at 125 °C for 2 hours to thoroughly eliminate bound solvent and crystal water, affording anhydrous zinc trifluoromethanesulfonate powder.
This process boasts prominent advantages: non-toxic CO₂ is easily removed, methanol features a low boiling point for simple separation, and there is no safety hazard from hydrogen gas throughout the procedure. Suitable for small-batch preparation of high-purity reagents, it is the most widely documented method in academic literature.
2. Direct Reaction Method Using Metallic Zinc
Metallic Zn powder reacts with trifluoromethanesulfonic acid via the equation: Zn + 2CF₃SO₃H → Zn(OTf)₂ + H₂↑. Acetone, acetonitrile or pure water can be selected as solvents.
Zn powder is added portionwise to the acid solution at room temperature, followed by stirring until the metal dissolves completely. The reaction releases hydrogen gas, which requires full ventilation and explosion-proof measures during the entire operation. Upon reaction completion, trace insoluble impurities are filtered off, and the filtrate is concentrated and dried under reduced pressure to obtain the target product.
This approach involves concise operating steps, yet accumulated hydrogen carries a risk of combustion and explosion. Moreover, excess zinc powder tends to introduce metallic impurities. It is only applicable for temporary in-situ preparation with low purity requirements and unsuitable for large-scale manufacturing.
3. Industrial Indirect Synthetic Route
Large-scale industrial production adopts a multi-step synthesis process. First, bis(trifluoromethylthio) disulfide is synthesized from carbon disulfide and trifluoromethyl iodide, then oxidized via mercury salt intermediates to produce an aqueous trifluoromethanesulfonic acid solution. After adjusting the acid concentration to 40%–60%, zinc oxide or metallic zinc is added, and the mixture is heated to reflux until the system turns neutral. The filtrate is evaporated and crystallized to obtain the finished product.
This route enables self-synthesis of trifluoromethanesulfonic acid feedstock to cut costs of purchasing external strong acid. Nevertheless, it involves lengthy process flows and mercury-based reagents, resulting in high waste treatment costs, and is exclusively adopted by large fine chemical manufacturers.
4. Double Displacement Precipitation Method (Rarely Used)
An aqueous solution of sodium trifluoromethanesulfonate is blended with zinc chloride solution, and the target product precipitates out via salting-out effect. However, residual sodium and chloride ions persist in the system, entailing complicated purification workflows. The resulting product fails to meet purity standards for catalytic-grade applications. This method merely serves for crude pre-synthesis with no practical application value.
Overall comparison: the zinc carbonate-methanol neutralization method is prioritized for laboratory use; a combined oxidation-neutralization process is selected for industrial mass production; the metallic zinc reaction method is reserved solely for emergency in-situ synthesis.
1. Fundamental Physical Parameters
It appears as white to light gray ultrafine powder with a density of 4.43 g/cm³ and a melting point ≥300 °C, exhibiting thermal stability without decomposition at high temperatures. The compound is highly hygroscopic and rapidly absorbs moisture from air to form a monohydrate upon exposure, hence requiring hermetic storage to isolate water vapor.
Its solubility demonstrates strong polar selectivity: freely soluble in water, acetonitrile and acetone; sparingly soluble in methanol and ethanol; completely insoluble in weakly polar organic solvents including dichloromethane, diethyl ether and alkanes, making it compatible with most polar organic catalytic systems.
2. Core Chemical Characteristics
The trifluoromethanesulfonate anion (OTf⁻) is a weakly coordinating anion. The strong electron-withdrawing effect of fluorine atoms drastically enhances the Lewis acidity of zinc ions, delivering far superior catalytic activity compared with zinc chloride and zinc sulfate.
It possesses excellent chemical stability at room temperature and does not undergo side reactions with functional groups such as esters, alkenes and ethers, granting broad functional group compatibility. Zinc hydroxide precipitate forms upon contact with strong bases, while ligand exchange occurs when exposed to strong nucleophiles.
The anhydrous form contains no free protons, eliminating protonic acid side reactions during catalytic processes and delivering outstanding stereoselectivity. It acts as a dedicated Lewis acid catalyst for glycosylation, thioacetalization, silylation and asymmetric addition reactions.
3. Safety, Storage & Application Properties
Classified as a corrosive substance under GHS, it causes severe burns upon contact with skin and mucous membranes; acid-resistant protective gear must be worn during handling, with UN dangerous goods number UN3261 assigned. It shall be hermetically stored in a cool, dry and inert atmosphere, avoiding humid air and alkaline reagents.
Beyond organic catalysis, this zinc salt finds applications in aqueous zinc-ion battery electrolytes, polymer polymerization additives and pharmaceutical intermediate synthesis. The weakly coordinating anion improves ionic conductivity of electrolytes, expanding its application scenarios in novel energy storage materials.
Boasting three core strengths - potent Lewis acidity, broad solvent compatibility and outstanding thermal stability - it serves as an irreplaceable zinc-based catalytic reagent in organic synthesis.
FAQ
What is another name for zinc triflate?
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Synonyms: Trifluoromethanesulfonic Acid Zinc(II) Salt. Zinc(II) Triflate.
How do you make zinc triflate?
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If desired, it may be prepared from reacting trifluoromethanesulfonic acid with zinc metal in acetonitrile, or with zinc carbonate in methanol: Zn + 2 HOTf → Zn(OTf) 2 + H. ZnCO 3 + 2 HOTf → Zn(OTf) 2 + H 2O + CO 2 (OTf = CF 3SO 3)
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