Preparation
Since Swarts first synthesized 2,2,2-Trifluoroethanol from trifluoroacetic anhydride using a catalytic reduction method in 1933, a series of synthetic methods have been developed. Based on the reaction type, these methods can be classified into three categories: oxidation, reduction, and hydrolysis. Based on the raw materials, they can be categorized into the trifluoroacetic acid method, the trifluoroacetyl chloride method, the trifluoroacetic anhydride method, the trifluoroacetate ester method, the trifluoroacetaldehyde method, the vinylidene fluoride method, the trifluoroethane (HFC-143a) method, and the trifluorochloroethane (HCFC-133a) method, among others.
Description
2,2,2-trifluoroethanol or trifluoroethanol is called TFEA or TEF, it is important intermediate of the fluorine-containing aliphatic, it is colorless, it is miscible liquids with water, it has similar odor with ethanol. Due to the strong electron-withdrawing effect of trifluoromethyl, acid of trifluoromethyl is stronger than ethanol, it can generate hydrogen-bonded stable complex (such as: tetrahydrofuran, pyridine) with heterocyclic compound. Due to this unique physical and chemical properties and special molecular structure, it has different performance with other alcohols, it can participate in a variety of organic reactions, it can be oxidized to acetaldehyde trifluoromethyl or trifluoroacetic acid, it can also provide trifluoromethyl, it can participate in the Still-Gennari improvements of Horner-Wadsworth-Emmons reaction. It has wide range of uses in medicine, pesticides, dyes, energy, and other aspects of organic synthesis.
The main use of trifluoroethanol is as anesthetic, at the earliest, fluorine acetylene ether which synthesized by trifluoroethanol and acetylene takes place of bigger side effects of bromine-fluoro alkanes as anesthetic, and then trichloroethanol is used as raw material to develop non-flammable, low toxicity isoflurane alkanes and high performance of the new anesthetic of chlorofluoroalkane. Trifluoroethanol can be introduced into drug structure as trifluoromethyl of functional group, it can generate significant physiological activity, increase fat-soluble of molecules, improve efficacy or reduce side effects of the organism, its synthetic drugs have central nervous system stimulants fluticasone Seoul, substituted pyridines stomach cytoplasmic proton pump inhibitor Lansoprazole and Pariprazole, antiarrhythmic drugs flecainide with amines and analgesic drugs benzodiazepines and dysuria treatment KMD-3212 and so on.
Chemical properties
Boiling point is 73.6℃, melting point is-43.5℃, refractive index is 1.2940, density (25 ℃) is 1.383g/cm3, enthalpy of evaporation is 37.8kJ/mol.
Uses
(1) It can be used as import agent of trifluoroethyl and trifluoroacetic ethoxycarbonyl agent, synthetic narcotics fluoride ether (Fluroxene), isoflurane (Isoflurane) and to chlorine halothane (Desflurane), central nervous system stimulants fluticasone Seoul (Flowotyl), proton pump inhibitor lansoprazole (Lansoprazol, pp inhibitors), anti-arrhythmic drugs flecainide with amine (Flecamide), analgesics, benzodiazepines (Quazepam), difficulty urinating therapeutic drug KMD-3213, herbicide trifluoromethyl thiomethyl (Triflusulfuronmethyl).
(2) It can be used for chemical reagents.
(3) It can be used as solvent, it can be used as import agent of trifluoroethyl and trifluoroacetic ethoxycarbonyl agent, it can be also used as pharmaceutical, pesticide intermediates.
(4) It can be used as solvent, it is also used as medicine, pesticide intermediates.
Preparation method
Since 1933 Swarts used trifluoroacetic anhydride as raw material, catalytic reduction method was used to get trichloroethanol, we have developed a series of synthetic methods. According to the type, the reaction can be divided into three kinds: oxidation, reduction and hydrolysis. According to raw material, it can be divided trifluoroacetic acid method, trifluoroacetyl chloride method, trifluoroacetic anhydride method, trifluoroacetate law, trifluoroacetic acetaldehyde, polyvinylidene fluoride method, trifluoroethane (HFC-143a) method and trifluoro chloroethane (HCFC-133a) method.
Hazards & Safety Information
Category: Flammable liquid
Toxicity grading: highly toxic
Acute oral toxicity-rat LD50: 240 mg/kg; Oral-Mouse LD50: 366 mg/kg
Irritation data: Skin-Rabbit 0.75 mg/24 hours and severe; Eyes-rabbit 20 mg/24 hr mild
Flammability hazard characteristics: When meets fire, heat, oxidants, it is flammable; it can burn and generate toxic fluoride fumes.
Storage characteristics: Treasury ventilation low-temperature drying; it should be stored separately with oxidants.
Extinguishing agent: Dry powder, dry sand, carbon dioxide, foam, 1211 fire extinguishing agent.
Chemical Properties
Colorless liquid
Uses
2,2,2-Trifluoroethanol (Trifluoroethyl alcohol, TFE) is used to study the conformational states of proteins and the folding refolding processes of proteins.
Uses
Trifluoroethanol serves as a solvent and a raw material in organic chemistry and biology. TFE is a solvent of choice for hydrogen peroxide-mediated oxidations of sulfides. Trifluoroethanol acts as a protein denaturant. It is used in the manufacture of certain pharmaceuticals and drug substances. The drug fluromer, which is 2,2,2-trifluoro-1-vinyloxyethane, is the vinyl ether of trifluorethanol. It is an effective solvent for peptides and proteins, and used for NMR-based protein folding studies, and in the manufacture of nylon. As a source of the trifluoromethyl group, it is employed in several organic reactions, for example in Still-Gennari modification of Horner-Wadsworth-Emmons reaction (HWE) reaction.
Uses
In synthesis of medical anaesthetics, pharmaceuticals, and agrochemicals; in polymerizations. Protein denaturant; stabilizes peptide structures. Cleaning solvent; eluent in HPLC separations; working fluid in Rankine heat cycle systems. Environmentally friendly alternative to CFCs.
Definition
ChEBI: 2,2,2-trifluoroethanol is a fluoroalcohol. It is functionally related to an ethanol.
Safety Profile
Poison by ingestion,
intravenous, and intraperitoneal routes.
Moderately toxic by inhalation and skin
contact. Experimental reproductive effects.
A severe skin and eye irritant. When heated
to decomposition it emits toxic fumes of F-.
Purification Methods
Dry it with CaSO4 and a little NaHCO3 (to remove traces of acid) and distil it. Highly TOXIC vapour. [Beilstein 1 IV 1370.]
