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Trifluoroethanol CAS 75-89-8

Molecular Formula: C2H3F3O

Formula Weight: 100.04

ZSpharmac: Trifluoroethanol Supplement

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Product Name: Trifluoroethanol
CAS No: 75-89-8
Purity: 99%

Basic Info

Product Name:Trifluoroethanol
Other Names:2,2,2-Trifluoroethanol
CAS:75-89-8
Place of Origin:Shandong, China
Brand Name:ZSpharmac
Type:Organic Chemical Raw Materials
Appearance:Clear Colorless Liquid
EINECS No.:200-913-6
Storage:Store Below +30°C.
Provide:Trifluoroethanol MSDS;
Trifluoroethanol COA

What is Trifluoroethanol?

Trifluoroethanol or trifluoroethanol is abbreviated as TEF or TFEA. It is an important aliphatic fluorine-containing intermediate. It is a colorless, water-miscible liquid with an odor similar to that of ethanol. Due to the strong electron-withdrawing effect of trifluoromethyl, trifluoroethanol is much more acidic than ethanol, and can form hydrogen-bonded stable complexes with heterocyclic compounds (such as tetrahydrofuran, pyridine). This unique physical and chemical properties and special molecular structure make it have different properties from other alcohols, can participate in a variety of organic chemical reactions, can be oxidized to trifluoroacetaldehyde or trifluoroacetic acid, and can also provide trifluoroacetaldehyde Methyl, a Still-Gennari modification involved in the Horner-Wadsworth-Emmons reaction. It has a wide range of uses in medicine, pesticides, dyes, energy, and organic synthesis.

Trifluoroethanol Properties:

Melting point −44 °C(lit.)
Boiling point 77-80 °C(lit.)
density 1.391 g/mL at 20 °C
vapor density 3.5 (vs air)
vapor pressure 70 mm Hg ( 25 °C)
refractive index n20/D 1.3(lit.)
Fp 85 °F
storage temp. Store below +30°C.
form Liquid
pka12.4(at 25℃)
Specific Gravity1.373
color Clear colorless
OdorAlcoholic odour
PH Range5-7 (10% aq soln)
explosive limit8.4-28.8%(V)
Water Solubility Miscible with water, ethers, ketones, alcohols and chloroform.

 

Field of Application of Trifluoroethanol

Pharmaceutical industry
The most important use of trifluoroethanol is as an anesthetic. The first use of fluoroacetylene ether synthesized from trifluoroethanol and acetylene to replace bromofluoroalkane with greater side effects as an anesthetic, and then to use trichloroethanol as raw material to develop non-flammable, Low toxicity isoflurane and high performance novel anesthetic agent dechlorofluoroalkane. Trifluoroethanol can introduce trifluoromethyl as a functional group into the structure of the drug, so that it can produce obvious physiological activity, increase the lipid solubility of the molecule, improve the efficacy or reduce the toxic and side effects of the organism. Mainly include the central nervous system stimulant flutir, substituted pyridine parietal cell proton pump blockers Lansoprazole and Pariprazole, etc., antiarrhythmic drug flecainide and analgesic drug benzodiazepine and dysuria treatment drug KMD- 3212 et al.

Dye industry
In dye synthesis, the introduction of CF3CH2O- in trifluoroethanol into phthalocyanine can increase its solubility and inhibit intermolecular polymerization. In addition, the introduction of CF3CH2O- and CF3- into some dye molecules can significantly improve the light resistance, weather resistance and chemical stability of the dyes.

As a reaction aid
Trifluoroethanol is a strong acid alcohol with strong hydrogen bonding ability and is miscible with organic systems, so it can be used as a catalyst, solvent and acylating agent in chemical synthesis. In the solid-phase synthesis of dihydropyrimidone and pyrimidone acid heterocyclic compounds from propionic acid resin, trifluoroethanol is used to introduce an easily deprotected group -OCH2CF3, which is beneficial to ring formation. -OCH2CF3 has been used in many organic synthesis reactions as an easily removable group, and trifluoroethanol can also be used as a ligand synthesis catalyst. Trifluoroethanol can dissolve oxygen-containing compounds such as water, alcohol, and ketone, and aromatic compounds such as benzene and toluene, and can dissolve various polymer resins. In the reaction, trifluoroethanol acts as a non-nucleophilic ionic solvent and can be used as a protective group for carboxylic acid; due to its low nucleophilicity and stability, trifluoroethanol is also used in some fluorination reactions and nucleophilic polymers such as polyoxymethylene It is an excellent solvent for polyamide, polyacrylonitrile, etc.; other polyolefins are polymerized with trichloroethanol as a solvent, which can obtain higher yield and reaction rate, and can greatly improve the stereoregularity of the polymer and improve the polymer performance; trifluoroethanol is often used as a solvent in some ionic reactions and electrochemical reactions. In view of the excellent solubility and high purity of trifluoroethanol, its use as a separation solvent for high performance liquid chromatography and a chromatographic separation solvent for chiral compounds is currently being developed. The enzymatic reaction using an organic solvent is different from the enzymatic reaction using an aqueous solution, a reversible reaction can occur, and the post-treatment is easy to attract attention. Acylation is often used for the acylation of alcohols and amines because of its ability to optically resolve and protect functional groups. Trichloroethanol is an alcohol with a lower nucleophilicity. It lacks reactivity to generate trifluoroethanol in the transesterification reaction, and the hydroxyl group on the other side of the reversible reaction can be acylated in one direction, so trifluoroethanol has begun It is widely used in the position-selective acylation of optically active alcohols and steroids, the optical resolution of amines and the synthesis of optically active pharmaceuticals.

As a solvent

Trifluoroethanol can dissolve oxygen-containing compounds such as alcohols and ketones and aromatic compounds such as benzene and toluene, and can dissolve various polymer resins. As a non-nucleophilic ionic solvent in the reaction, trifluoroethanol can be used as a protective group for carboxylic acid; due to its low nucleophilicity and stability, trifluoroethanol is also an excellent solvent for some fluorination reactions and nucleophilic polymers , such as polyoxymethylene, polyamide and polyacrylonitrile; other polyolefins are polymerized with trifluoroethanol as a solvent, which can obtain higher yield and reaction rate, and can greatly improve the stereoregularity of the polymer and improve the polymer Trifluoroethanol is often used as a solvent in some ionic reactions and electrochemical reactions; recently, in view of its excellent solubility and high purity, trifluoroethanol is being developed as a separation solvent and chiral compounds in high performance liquid chromatography chromatographic separation of solvents. Trifluoroethanol is used as a solvent in organic chemistry. Oxidation of sulfur compounds with hydrogen peroxide often uses TFE as a solvent. In biology, TFE can be used as a co-solvent when studying protein folding with NMR spectroscopy. This solvent effectively dissolves peptides and proteins. At certain concentrations, TFE can strongly affect the three-dimensional structure of proteins. Industrially, trifluoroethanol is a solvent used in the production of nylon and pharmaceuticals.

energy field
Due to its strong thermal stability and good kinetic properties, trifluoroethanol was originally only used in some heat recovery systems. Due to its zero damage coefficient to the ozone layer, global environmental issues and energy conservation issues have been paid more and more attention. Trifluoroethanol can replace Freon in the future, so its importance in these fields has been re-evaluated and recognized. At present, the mixture of trifluoroethanol and water is used as the working medium of the Rankine cycle of waste heat recovery power generation system for waste heat recovery power generation system. There is great potential in system working fluids. In addition, people take advantage of the characteristic that trifluoroethanol and amide compounds can generate a large amount of heat of dissolution when mixed with cyclic amide compounds such as trifluoroethanol and N-methylpyrrolidone, N,N-dimethylimidazolidinone. Compared with the existing chemical heat pump, it does not freeze at low temperature, the equipment is compact, and the energy efficiency of cooling and heating High, industrial and civil prospects are promising.

Synthetic material field
The traditional phosphazene rubber was unstable, and was later stabilized by replacing it with a variety of different fluorine-containing alcohols to prepare polyfluoroalcohol-substituted phosphazene rubber. Used in aerospace, electrical and electronic fields. In recent years, the research on fluorophosphazene rubber has gradually increased, introducing vinyl groups, imparting cross-linking curability, and introducing bulky modifying groups for resin moldability and resin surface modification, so that they can be used in coatings, adhesives, and filler materials. , sealing materials and electronic materials. Trichloroethanol is esterified with methacrylate to obtain trifluoroethanol methyl methacrylate. Compared with methyl methacrylate, it has better polymerizability and is easy to mix with other acrylates, styrene, acrylonitrile, vinyl acetate, etc. Copolymerization, because of the trifluoromethyl group, the polymer has good compatibility, surface properties, optical properties, gas permeability, electrical properties, low water absorption, and has good properties in the modification of resin functionality. Development prospects, widely used in coatings, optical information transmission, information chemicals, printed circuits, photoresist materials and other fields. In addition, in polyester synthesis, the introduction of -OCH2CF3 can improve the equilibrium constant and obtain polyester with desired molecular weight.

Field of organic synthesis
As an important basic organic fluoride, trifluoroethanol is more and more widely used in organic synthesis. Trifluoroacetaldehyde synthesized from trifluoroethanol is a typical fluorine-containing aldehyde, which is mainly used in industries such as synthetic resin, high polymer, rubber, paint, medicine and agricultural pesticides. The trifluoroacetal acetal synthesized by the electrochemical method can replace trifluoroacetaldehyde as a trifluoromethyl reagent for the synthesis of 1-furan-2,2,2-trifluoroethanol. In order to overcome the complexity and danger in the synthesis of traditional fluorobenzene and its derivatives, diazonium salts can be hydrolyzed in trifluoroethanol to obtain fluorobenzene in a certain yield; trichloroethanol and triphenylphosphonium dibromide are synthesized Ph3P(OCH2CF3)2 is an intermediate with great potential in organic synthesis; fluorine-containing allyl alcohol synthesized from trichloroethanol can further synthesize many compounds containing -CF3 groups; Alkenyl ethers, etc. can be synthesized by diene to obtain mono- or di-fluorine substituted cyclic compounds, and trifluoroethanol can also react with trinitrobenzene or benzonitrile to form nitrobenzene substituted by trifluoroethoxy, such as 3 – Nitrogen-4-(2,2,2-trifluoroethoxy)benzonitrile, etc.

Other aspects
In the pesticide industry, trifluoroethanol can be used to synthesize herbicides such as trifluorothiomethyl. In addition, trifluoroethanol has many uses, most notably on proteins and enzymes. The unique physicochemical properties of trifluoroethanol can convert peptides into stable α-helical structures and denature natural proteins. This effect of trifluoroethanol can inhibit chemical reactions such as deamination or racemization of peptides , thus playing the role of stabilizing peptides, making it possible for some biological products to become commercial products; trifluoroethanol can effectively prevent the accumulation and inactivation of proteins in reversed-phase columns; the mixed system of trifluoroethanol and water is used in the capillary electrophoresis of peptides Separation method can significantly improve the separation efficiency.

Preparation Method of Trifluoroethanol

Since 1933, Swarts used trifluoroacetic anhydride as a raw material to prepare trichloroethanol by catalytic reduction, and a series of synthetic methods have been developed one after another. According to the type of reaction, it can be divided into three types: oxidation method, reduction method and hydrolysis method. According to the raw materials, it can be divided into trifluoroacetic acid method, trifluoroacetyl chloride method, trifluoroacetic anhydride method, trifluoroacetate method, trifluoroacetaldehyde method, vinylidene fluoride method, trifluoroethane (HFC-143a) method and Trifluorochloroethane (HCFC-133a) method, etc.

Trifluoroacetyl chloride method
Using trifluoroacetyl chloride as raw material, trifluoroethanol can be obtained by catalytic hydrogenation reduction reaction. The choice of catalyst is the key to the synthesis. If lithium aluminum hydride is used as the catalyst, it is only suitable for laboratory preparation due to the disadvantages of expensive catalyst, difficult operation and inability to regenerate and reuse. Palladium, platinum and ruthenium are suitable catalysts. These catalysts can be regenerated and activated by relatively simple methods. Even if they are not activated, their lifespan can reach more than 24 hours. Palladium is the most ideal catalyst. In order to improve the heat resistance of the catalyst, the catalyst palladium is preferably supported on aluminum or other inert supports such as silica gel and bentonite. The method for preparing trifluoroethanol by using palladium/aluminum as a catalyst and reducing trifluoroacetyl chloride with oxygen has the characteristics of simple equipment, high conversion rate of raw materials, good product yield and the like, and has industrial production value. It is difficult to separate acetyl chloride from the by-product hydrogen chloride. The synthesis can be divided into two methods, gas phase and liquid phase. The gas-phase reaction can be carried out under normal pressure or under pressure. Since the boiling point of trifluoroacetyl chloride is relatively low, the liquid-phase reaction must be carried out under pressure. In the continuous gas phase reaction process, since the reaction between trifluoroacetyl chloride and hydrogen can be completed in an instant, the contact time between the raw material and the catalyst is very short, generally only 5 to 10 seconds. For example, under high temperature and high pressure conditions, the contact time is Shorter, which is good for improving viability. In general, the yield of trifluoroethanol can reach 75% to 95%.


Trifluoroacetic anhydride method
The production of trifluoroethanol by liquid-phase hydrogenation reduction of trichloroacetic anhydride is the earliest method used to produce trifluoroethanol at home and abroad. However, trifluoroacetic anhydride is prone to deep reduction to form hemiacetals, esters, acids, and even hydrocarbon compounds. At a reaction temperature of 20-40° C. and a pressure of 4.5-5.0 MPa, a liquid-phase hydrogenation reduction reaction is carried out with platinum as a catalyst, and the main products generated are trifluoroacetic acid, trifluoroethyl ester, trifluoroethanol and trifluoroethane. Using platinum or nickel as a catalyst, the gas-phase hydrogenation reduction of trifluoroacetic anhydride, the main product is trifluoroethanol. Using rhodium/activated carbon or rhodium/aluminum as catalyst, the reaction temperature is 50~150℃, and the liquid phase hydrogenation reduction is carried out under the reaction pressure of 0.5~1.5MPa, and the yield of trifluoroethanol can reach 75%. The method is simple in technology and convenient in operation, but is prone to produce a large number of by-products.

Trifluoroacetic acid method
Under the action of a catalyst, 1 molecule of trifluoroacetic acid reacts with 2 molecules of hydrogen to generate 1 molecule of trifluoroethanol. The reaction can be carried out in the gas phase or in the liquid phase. In the gas phase hydrogenation reaction, the yield of trichloroethanol is only 37% with chromium or copper-based compounds as catalysts; with rhodium or iridium-based compounds as catalysts, the yield of trifluoroethanol is even lower, only 1.4%. Because of the high reaction temperature of the gas phase reaction and the low product yield, industrially, the liquid phase method is generally used for production. The liquid phase method can be carried out in batch or continuous mode. The batch method uses rhodium, rubidium, iridium, etc. as catalysts, and is carried out at 0.5-5 MPa and 70-150 ° C. The conversion rate of trifluoroacetic acid and the yield of trifluoroethanol are both. Very high, but a certain amount of by-products such as trichloroethane, ethane, and methane are formed due to the deep reduction of trifluoroacetic acid. The continuous liquid phase method has the characteristics of large reaction capacity, simple operation, good raw material conversion rate and product yield, and is used in industrial production.


Chlorotrifluoroethane method (HCFC-133a)
Trifluorochloroethane used in the chemical industry of the School of Materials and Chemical Engineering of Zhejiang University was reacted with potassium ω-carboxybutyrate in the presence of γ-butyrolactone at 200°C and 4.5MPa to obtain trifluoroethanol, and the by-product ω-hydroxybutyrate after the reaction Potassium acid can be reduced to γ-butyrolactone for recycling. Shanghai Organic Institute of Chinese Academy of Sciences uses trifluorochloroethane as raw material, in the presence of phase transfer catalyst, temperature 150-300 ℃, pressure 4-15MPa, reacts with alkali or alkali metal salt of carboxylic acid in aqueous solution to prepare trifluoroethanol, The phase transfer catalyst can be an ionic or non-ionic surfactant or a fluorine-containing compound with a molecular formula of XC-nF2OCFSOY, and the like. In addition, Zhejiang Research Institute of Chemical Industry has developed a process route for synthesizing trifluoroethanol with trifluorochloroethane as raw material, esterification and hydrolysis in two steps.

About Us

The production base is located in Zhangqiu chemical industry park and Tai’an high-tech chemical industry park. laboratory and workshop in strict accordance with the GMP standard and the product fit national ISO9001 and ISO2000 standards.

“Zhishang” products are exported to Europe, North and South America, the Middle East, Asia Pacific and Africa area, so as to establish a long-term and stable cooperation relationship with customer in the world.

Company Info
  • Business Type: Manufacturer
  • Product Range: Additive , Chemical Auxiliary & Catalyst , Organic Chemicals
  • Products/Service: Organic Intermediate,Inorganic Chemistry, APIs, Dyestuffs And Pigments, Fragrance And Spices, Food Additives
  • Total Employees: 51~100
  • Capital (Million US $): 10000000RMB
  • Year Established: 2016
Production Capacity
  • No. of Production Lines : 8
  • No. of QC Staff : 5 -10 People
  • OEM Services Provided : yes
  • Factory Size (Sq.meters) : 3,000-5,000 square meters
  • Certificate: ISO9001 , CE , GMP , API , MSDS
  • Factory Location : Diao Town Industry Park, Zhangqiu City, Jinan City, Shandong Province, China.

Service

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*Any inquiries will be replied within 24 hours.

*we provide Commerical Invoice, Packing List, Bill of loading, COA , Health certificate and Origin certificate. If your markets have any special requirements, let us know.

 

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FAQ

Do you accept sample order?

We will make samples before mass production, and after sample approved, we’ll begin mass production. Doing 100% inspection during production, then do random inspection before packing.

 

HOW TO CONFIRM THE PRODUCT QUALITY BEFORE PLACING ORDERS?

You can get free samples for some products,you only need to pay the shipping cost or arrange a courier to us and take the samples. You can send us your product specifications and requests,we will manufacture the products according to your requests.

What’s your MOQ?

Our MOQ is 1kg. But usually we accept less quantity such as 100g on the condition that sample charge is 100% paid.

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Yes. We’ll give you product analysis report before shipping.

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Different quantity has different discount.

Shipping

1. ≤50kg, Express delivery recommended, usually called as DDU service;

2. ≤500kg, Air shipping recommended, usually called as FOB, CFR, or CIF service;

3. >500kg, sea shipping recommended, usually called as FOB, CFR, or CIF service;

4. For high value products, please select air shipping and express delivery for safe.

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