JPS6253491B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention provides a novel compound, 1-phenyl-
The present invention relates to 1-(3'.3'.3'-trifluoropropylphenyl)ethane, a method for producing the compound, and a synthetic oil containing the compound. Polychlorinated biphenyl is insoluble in water, but in oil,
It has excellent properties such as being soluble in organic solvents and mixed with plastics, being chemically inert and stable against chemical agents, being nonflammable, having good insulation properties, and not drying even when formed into a thin film. Therefore, polychlorinated biphenyl has conventionally been widely used as an insulating oil for capacitors and an insulating oil for transformers, and has also been used as a heat medium, a solvent for non-carbon paper, and a plasticizer. However, polychlorinated biphenyl has poor biodegradability, and once it enters the body, it is not excreted and accumulates in the body, causing poisoning symptoms, so its use has become regulated. Since then, various alternative compounds have been proposed;
A compound such as polychlorinated biphenyl, which has a high dielectric constant, high insulation resistance, and low dielectric loss tangent, and has excellent biodegradability without polluting the natural environment has not been proposed. As a result of intensive research in search of a compound that has electrical properties comparable to polychlorinated biphenyl and is easily biodegradable in the natural environment, the present inventors discovered a new compound, 1-phenyl-1-(3' The present invention was achieved by synthesizing 3',3'-trifluoropropylphenyl)ethane. The compound of the present invention can be synthesized using 1,1-diphenylethane and 3,3,3-trifluoropropene as starting materials and using an acid catalyst. The reaction formula is shown below. As acid catalysts, for example HF, _BF3 can be used. The reaction method can be continuous or batchwise;
Synthesis can be carried out under relatively mild temperature conditions.
As an example, a case of batch type will be explained. 1,1-diphenylethane, 3,3,3-trifluoropropene, and an acid catalyst are introduced into a stainless steel autoclave and reacted at a predetermined reaction temperature for 1 to 30 hours. The reaction temperature depends on the catalyst and is BF ₃
In the case of HF, the preferred range is 0 to 50°C, and in the case of HF, the preferred range is 30 to 120°C. After the reaction is complete, the residual gas is discharged from the reaction system, the catalyst is removed from the reaction mixture, and the reaction mixture is distilled under reduced pressure to produce 1-phenyl-1-(3', 3', 3'-), a colorless and transparent liquid. Trifluoropropylphenyl)ethane is obtained. In addition, the novel compound of the present invention is considered to include the following positional isomers. The compound of the present invention has excellent electrical properties and can be used as an insulator, particularly as an insulating oil. The compound of the present invention has an excellent dielectric constant that is thought to be due to the trifluoropropyl group it has, so it can be applied as an insulating oil for capacitors, improving the performance and miniaturizing capacitors and devices using capacitors. can be expected to contribute to Hereinafter, the present invention will be explained in more detail based on Examples. <Example> In a stainless steel autoclave with a capacity of 1.
240 g of 1-diphenylethane and 127 g of 3,3,3-trifluoropropene were charged, and BF ₃ was further press-fitted into this until the internal pressure reached 60 kg/cm ² G.
The reaction was allowed to proceed at room temperature for 20 hours. After the reaction was completed, residual gas was purged, and then the contents were extracted with methylene chloride. This was washed with water and dried according to a conventional method, and then methylene chloride was distilled off using a rotary evaporator. The reaction mixture thus obtained was precision distilled under reduced pressure to a boiling point of 118-120℃/1mmHg.
A fraction of was obtained. The fraction was determined by gas chromatography and the analysis results shown below.
1-Phenyl-1- with a purity of over 99%
It was confirmed to be (3', 3', 3'-trifluoropropylphenyl)ethane. (a) Mass spectrometry (20eV) m/e278 Figure 1 shows the mass spectrum near the parent peak. (b) NMR ¹ H−NMR, CCl ₄ solution δ (ppm) 1.63(d) [−CH ₃ (3H) J=7.0Hz] 1.9 to 3.0 (m) [−CH ₂ −(4H)] 4.10(q ) [

[Formula] (1H)J=7.0Hz] 6.9～7.5〔

[Formula] (9H)] ¹⁹ F-NMR, −CF ₃ signal was observed as a triplet at +2.5 ppm from the internal standard benzotrifluoride (J _HF = 10.1
Hz). (c) Elemental analysis Actual value (%) Calculated value (%) C 73.3 73.4 H 6.0 6.1 F 20.7 20.5 (d) Infrared absorption spectrum The spectrum is shown in Figure 2. (e) Boiling point 118-120°C/1 mmHg (f) Specific gravity 1.116 (20°C) (g) Refractive index 1.5121 (20°C) Next, the electrical properties of the compound of the present invention at 20°C are shown below. Dielectric constant 4.60 Dielectric loss tangent (%) 0.067 Volume resistivity (Ω・cm) 1.20×10 ¹⁴

[Brief explanation of the drawing]

FIG. 1 shows the mass spectrum of the compound of the present invention, and FIG. 2 shows the infrared absorption spectrum of the compound of the present invention.

Claims (1)

[Claims] 1 formula 1-phenyl-1-(3', 3', 3'-trifluoropropylphenyl) ethane. 2 1-phenyl-1-(3'.
A method for producing 3′,3′-trifluoropropylphenyl)ethane. 3. The manufacturing method according to claim 2, wherein the acid catalyst is HF or _BF3 .