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Scandium trifluoromethanesulfonate, also known as scandium(iii), is a white powder that is highly hygroscopic. This compound is recognized for its versatility and effectiveness as a catalyst in various organic reactions. Its primary role is as a Lewis acid, which makes it particularly useful in reactions that require acid catalysis. One of the significant applications is in the Friedel-Crafts acylation and Diels-Alder reactions, where it acts as a crucial catalyst for the formation of carbon-carbon bonds. It is also known for its ability to stereochemically catalyze the radical polymerization of acrylates, demonstrating its efficiency and selectivity in complex organic transformations.
Moreover, it is an active, renewable, and reusable acylation catalyst. It has been employed in the reductive ring-opening functionalization of triethylsilane pyranoside glycosides and in the synthesis of bullvalene through a stabilized sulfur ylide. The compound's stability under normal conditions, coupled with its reactivity under specific conditions like high temperatures or in the presence of strong oxidants, makes it a valuable tool in organic synthesis.
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Chemical Formula |
C3F9O9S3Sc |
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Exact Mass |
491.81 |
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Molecular Weight |
492.15 |
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m/z |
491.81 (100.0%), 493.81 (13.6%), 492.82 (3.2%), 492.81 (2.4%), 493.82 (1.8%) |
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Elemental Analysis |
C, 7.32; F, 34.74; O, 29.26; S, 19.54; Sc, 9.13 |
Scandium trifluoromethanesulfonate, with the chemical formula Sc (SO3CFI3) or Sc (OTf) I3, is a white powdery solid that is hygroscopic and stable in water. As an important Lewis acid catalyst in organic chemistry, it has demonstrated extensive application value in multiple fields due to its unique chemical properties and catalytic activity.
Organic synthesis field
Carbon carbon bond formation reaction
Friedel Crafts acylation/alkylation reaction: It is an efficient catalyst for Friedel Crafts acylation and alkylation reactions. It can activate substrates such as acyl chlorides or olefins, promote their reaction with aromatic compounds, and generate corresponding acylation or alkylation products. This catalyst can function under mild conditions and has a significant effect on electron rich aromatic rings, making it widely used in the synthesis of pharmaceutical intermediates and fragrances.
Diels Alder reaction: As a catalyst for Diels Alder reaction, it can accelerate the cycloaddition reaction between dienes and dienophiles, generating hexagonal cyclic compounds.
Aldol condensation reaction: It can efficiently catalyze the aldol condensation reaction between aldehydes/ketones, producing β - hydroxyketones or α, β - unsaturated ketones. This reaction is commonly used as a key step in the synthesis of natural products and drug molecules.
Mannich reaction: In the Mannich reaction, it can catalyze the three component condensation of aldehydes, amines, and active methylene compounds to generate β - aminocarbonyl compounds. These compounds are the core backbone of many bioactive molecules.
stereoselective reaction
Asymmetric catalysis: When combined with chiral ligands, it can achieve excellent asymmetric catalysis and induce the formation of chiral centers. For example, in the Mukaiyama aldol reaction, this catalyst can achieve high enantioselectivity and provide a key chiral intermediate for the total synthesis of natural products.
Stereoselective polymerization: can be used as a component of Ziegler Natta type catalysts to regulate the stereoregularity of polyolefins and synthesize polymer materials with specific physical properties.
Other organic reactions
Esterification and ester exchange reactions: It can efficiently catalyze the direct dehydration esterification reaction of carboxylic acids and alcohols, especially suitable for substrates with high steric hindrance or acid sensitivity. Meanwhile, it can also promote ester exchange reactions with mild conditions and high yields.
Lactylation reaction: This catalyst can effectively catalyze the intramolecular cyclization of hydroxy acid molecules to form lactones, providing an important method for the synthesis of natural products.
Olefin metathesis reaction: Synergistic effect with ruthenium carbene catalyst can reduce the activation energy of olefin metathesis reaction and improve reaction efficiency.
Hydrogenation thiol reaction: In the hydrogenation thiol reaction of aromatic and aliphatic thiols, it can be used as a promoter to enhance reaction activity.
Double electron reduction reaction: This catalyst can catalyze the selective double electron reduction reaction of ferrocene derivatives on O ₂, providing an important reaction for organic electronics.
Materials Science Field
High frequency device materials
Preparation of Sc doped Gallium Nitride (Sc GaN) Thin Films: Scandium trifluoromethanesulfonate can be used as a precursor for Atomic Layer Deposition (ALD) to prepare Sc doped Gallium Nitride thin films. This film has excellent pressure resistance and heat dissipation performance, which can improve the performance and reliability of high-frequency devices in 5G base stations.
High frequency electronic device applications: Sc GaN thin films have broad application prospects in high-frequency electronic devices, such as high-frequency amplifiers, switches, and sensors. As a key precursor material, it provides important support for the development of high-frequency electronic devices.
Other material applications
High temperature resistant resin crosslinking agent: can be used as a crosslinking agent in the polymer industry to prepare high temperature resistant resins. These resins have broad application prospects in fields such as aerospace and automotive manufacturing.
Optical material dopants: can be incorporated into glass or ceramics to enhance the refractive index and other optical properties of the material. This provides a new avenue for the development of optical materials.
Synthesis and Modification of Polymer Materials
Preparation of stereoregular polymers:
As a component of Ziegler Natta catalyst, it can regulate the stereoregularity of polyolefins such as polypropylene and polyethylene. By synergizing with transition metal catalysts such as titanium and zirconium, it is possible to induce directional polymerization of alpha olefins, resulting in the formation of high melting point and high crystallinity isotactic polymers, significantly improving the mechanical properties and thermal stability of the material.
Biobased polymer catalysis:
In the synthesis of bio based polymers such as polylactic acid and polyhydroxyalkanoates, it can catalyze the ring opening polymerization reaction of lactic acid or hydroxy fatty acid monomers.
Its water phase stability allows for the direct use of aqueous monomers, simplifies the process flow, and avoids the toxicity issues of traditional catalysts (such as tin compounds), meeting the requirements of green chemistry.
Polymer functionalization modification:
Can catalyze the conversion reaction of functional groups on polymer chains. For example, in the side chain chlorination reaction of polystyrene, chlorine gas is activated as a Lewis acid to achieve efficient and selective chlorination modification, providing a new approach for the preparation of functionalized polymer materials.
Energy Materials and Electrochemical Applications
Lithium ion battery electrolyte additive:
Its anion (OTf ⁻) has a strong electron withdrawing effect, which can stabilize the anion structure of lithium salts (such as LiTFSI), improve the ionic conductivity and thermal stability of the electrolyte. In solid-state batteries, doped polymer electrolytes can inhibit lithium dendrite growth and prolong battery cycle life.
Proton exchange membrane for fuel cells
Its strong acidity makes it a potential modifier for proton exchange membranes (PEM). By compounding with perfluorosulfonic acid resin (such as Nafion), the proton conductivity of the membrane can be enhanced.
While improving its mechanical strength and chemical stability, making it suitable for high-temperature fuel cell systems.
Electrode materials for supercapacitors
Conductive polymers synthesized by catalysis, such as polypyrrole and polyaniline, have high specific surface area and excellent electrochemical properties. For example, the catalytic synthesis reaction of polypyrrole can be carried out in aqueous phase to generate nanostructured polypyrrole electrode materials, significantly improving the energy density and power density of supercapacitors.
Green Chemistry and Sustainable Development
Green catalyst
Water phase reaction catalyst: It exists stably in water and maintains high catalytic activity, and can directly carry out many condensation reactions in water or aqueous solvents. This conforms to the principles of green chemistry, reducing the use of organic solvents and the generation of waste.
Recyclable and Reusable: After the reaction, it can often be recovered and reused through simple water washing and extraction. This reduces the cost of catalyst usage and environmental burden, in line with the requirements of sustainable development.
Low load catalyst
Efficient catalytic performance: It has extremely high catalytic activity and can achieve efficient catalysis at low loading amounts (catalytic amount, 1-10 mol%). This reduces the amount of catalyst used, lowers reaction costs, and reduces environmental impact.
Reducing waste acid and heavy metal pollution: Compared with traditional strong proton acid or heavy metal catalysts, it as a green catalyst significantly reduces the generation of waste acid and heavy metal pollution. This is beneficial for protecting the environment and human health.
CO2 resource utilization:
It can catalyze the cycloaddition reaction of CO ₂ with epoxides to generate cyclic carbonates (such as ethylene carbonate). This reaction occurs under mild conditions and Sc (OTf) ∝ can be recycled, providing an efficient pathway for the chemical fixation and resource utilization of CO ₂.
Biomass conversion:
In the catalytic conversion of biomass (such as cellulose and lignin), hydroxyl or ether bonds in biomass can be activated to promote their degradation into platform chemicals (such as glucose and aromatic compounds).
For example, the cellulose hydrolysis reaction catalyzed by Sc (OTf) ∝ can be carried out in aqueous phase, with a yield of glucose generation of over 80%, providing a key catalyst for biorefinery technology.
Wastewater treatment and heavy metal recovery:
Its strong Lewis acidity makes it an effective adsorbent for heavy metal ions in wastewater treatment. By combining with functional materials such as ion exchange resins and magnetic nanoparticles, Sc (OTf) U3 can selectively adsorb heavy metal ions such as lead and cadmium in wastewater, and achieve catalyst regeneration and heavy metal recovery through simple acid washing.
Analytical Chemistry and Sensor Technology
Fluorescent probes and chemical sensors:
It can be combined with fluorescent dyes such as rhodamine and fluorescein to construct fluorescent probes with high selectivity for metal ions (such as Fe ³ ⁺, Cu ² ⁺) or anions (such as F ⁻, CN ⁻). For example, the Sc (OTf) ∝/Rhodamine B system undergoes fluorescence quenching in the presence of F ⁻ and can be used for the detection of fluoride ions in the environment.
Chromatographic separation material:
Silica gel or polymer modified with Sc (OTf)3 can be used as a stationary phase for high-performance liquid chromatography (HPLC) for separating chiral compounds or metal ions. Its unique coordination ability can achieve high-resolution separation of complex mixtures, providing technical support for fields such as drug analysis and environmental monitoring.
Nanotechnology and Material Synthesis
Nanoparticle catalyzed synthesis:
Catalytic synthesis of core-shell structures of metal nanoparticles such as gold, silver, and platinum. For example, in the presence of Sc (OTf) 3, uniformly sized gold nanoparticles can be generated through reduction reactions, and their surface plasmon resonance effects have potential applications in fields such as photocatalysis and biological imaging.
Construction of Metal Organic Frameworks (MOFs):
Scandium trifluoromethanesulfonate, as a metal source, can participate in the synthesis reaction of MOFs. For example, Sc (OTf) 3 can react with terephthalic acid to generate Sc MOF materials with high specific surface area and porosity, which can be used for gas adsorption, catalysis, or drug delivery.
I. Classic Laboratory Neutralization Route via Scandium Oxide (Main Small-Scale Experimental Method)
This route adopts high-purity scandium sesquioxide (Sc₂O₃) and trifluoromethanesulfonic acid (TfOH) as core raw materials, serving as a universal preparation protocol for academic research and development. Its underlying reaction is the neutralization reaction between metal oxide and superacid.
Operating procedure: Load 99.9% high-purity Sc₂O₃ into a three-neck flask equipped with a reflux condenser.
Prepare a TfOH solution diluted with an equal volume of deionized water, then add it dropwise slowly to the suspension of solid oxide. Heat the system to 100 °C for constant-temperature reflux stirring over 72 hours until the off-white oxide dissolves completely to form a homogeneous clear solution.
After reaction completion, centrifuge to remove trace insoluble impurities, and remove most free water from the filtrate via vacuum rotary evaporation. Transfer the crude solid to a vacuum drying oven and conduct continuous drying at 403 K under high vacuum for 40 hours to thoroughly eliminate crystal water and residual free acid, yielding anhydrous white powdered Sc(OTf)₃.
This route features readily available raw materials with water as the sole byproduct, and the product purity can exceed 99.5%, suitable for manufacturing catalyst-grade reagents. Its drawbacks include an extremely long reaction cycle and highly corrosive TfOH, making heat release difficult to control during large-scale production.
II. Novel Industrial One-Step Gas-Solid Synthesis Process (Mass Production Optimized Route)
An industrial patented scandium carbonate-gas synthesis method has been developed to avoid high costs and severe corrosion arising from massive consumption of high-purity TfOH.
Disperse scandium carbonate in an inert organic solvent to prepare a suspension. Control the jacket temperature of the reactor at 60–65 °C, then feed a mixed gas of trifluoromethane and sulfuryl fluoride into the closed system continuously for 20 minutes under synchronous stirring. After gas feeding, maintain heat and stirring for 2–4 hours; the reaction endpoint is confirmed when the system pH stabilizes at 6.2–6.5.
Purge residual acidic tail gas with nitrogen, filter out inorganic salt byproducts, and subject the filter cake to low-temperature vacuum drying to obtain the finished product directly.
Remarkable process advantages: Mild and controllable heat release throughout the whole process, single-step reaction yield above 99.2%, no prolonged high-temperature reflux required, and drastically improved mass production efficiency. The main disadvantage is that production equipment must be airtight and fluorine-corrosion resistant, coupled with a complicated tail gas treatment workflow, restricting its application to ten-thousand-ton special reagent production lines only.
III. Key Points of Post-Treatment and Quality Control for the Target Product
Scandium trifluoromethanesulfonate is highly hygroscopic, and the drying procedure directly determines its catalytic activity. The crude product must undergo deep dehydration at high temperature under high vacuum; trace moisture will drastically weaken its Lewis acidity. After drying, rapidly transfer the solid into a desiccator loaded with phosphorus pentoxide for sealed light-shielded storage.
Quality control tests cover rare earth metal impurities, residual free trifluoromethanesulfonic acid and water content. For catalyst-grade products, water content shall be controlled below 50 ppm, and total metallic impurities shall not exceed 10 ppb to avoid excessive side reactions in catalytic processes.
The two synthetic routes apply to distinct scenarios: the scandium oxide neutralization method is preferred for laboratory research, while the scandium carbonate gas-solid synthesis process is selected for industrial batch manufacturing.
FAQ
What is scandium triflate used for?
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Scandium trifluoromethanesulfonate (triflate), which is commercially available, is a practical and useful Lewis acid catalyst for acylation of alcohols with acid anhydrides or the esterification of alcohols by carboxylic acids in the presence of p-nitrobenzoic anhydrides.
How to dry scandium triflate?
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Drying of Scandium(III) triflate: Heat 4.90 g (10.0 mmol) of Sc(OTf)3 for 1 hour in an evacuated (approx. 1 hPa) 500 mL three-neck flask with nitrogen and vacuum inlet to 180 °C in an oil bath to remove all moisture.
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