JPS6241581B2 - - Google Patents
Info
- Publication number
- JPS6241581B2 JPS6241581B2 JP18656380A JP18656380A JPS6241581B2 JP S6241581 B2 JPS6241581 B2 JP S6241581B2 JP 18656380 A JP18656380 A JP 18656380A JP 18656380 A JP18656380 A JP 18656380A JP S6241581 B2 JPS6241581 B2 JP S6241581B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- compound
- trifluoropropyl
- reaction
- benzene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 4
- GPDIHJRNVFDLDB-UHFFFAOYSA-N 1-dodecyl-2-(3,3,3-trifluoropropyl)benzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1CCC(F)(F)F GPDIHJRNVFDLDB-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 150000003071 polychlorinated biphenyls Chemical group 0.000 description 5
- 239000003990 capacitor Substances 0.000 description 4
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 2
- NLMURJDGDBEMAB-UHFFFAOYSA-N 3,3,3-trifluoropropylbenzene Chemical compound FC(F)(F)CCC1=CC=CC=C1 NLMURJDGDBEMAB-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FFTOUVYEKNGDCM-OWOJBTEDSA-N (e)-1,3,3-trifluoroprop-1-ene Chemical compound F\C=C\C(F)F FFTOUVYEKNGDCM-OWOJBTEDSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000005374 Poisoning Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Organic Insulating Materials (AREA)
Description
本願発明は、新規化合物であるｎ―ドデシル―
（３，３，３―トリフルオロプロピル）ベンゼ
ン、該化合物の製造方法及び該化合物を含有する
合成油に関する。
ポリ塩化ビフエニルは水に不溶であるが、油、
有機溶剤に可溶でプラスチツクともまじり、化学
的に不活性で化学薬剤に安定であり、不燃性、絶
縁性がよく、薄膜状にしても乾燥しない等のすぐ
れた性質を有する。したがつて、従来ポリ塩化ビ
フエニルはコンデンサー用絶縁油、トランス用絶
縁油として多用され、他に熱媒体、ノンカーボン
紙用溶剤、可塑剤としても使用されていた。しか
し乍ら、ポリ塩化ビフエニルは生物的分解性に劣
り、いつたん体内に入ると排泄されずに体内に蓄
積され、中毒症状をひきおこすのでその使用が規
制されるようになつた。
以来、種々の代替化合物が提案されているが、
ポリ塩化ビフエニルの如き高誘電率、高絶縁抵抗
及び低誘電正接を有し、自然環境を汚染しない生
物的分解性の優れた化合物は提案されていない。
本発明者等は、ポリ塩化ビフエニルに匹敵する
電気的特性を有し且つ自然環境で生物的分解を受
け易い化合物を求めて鋭意研究した結果、新規化
合物である。
ｎ―ドデシル―（３，３，３―トリフルオロプ
ロピル）ベンゼンを合成し、本発明に到達したも
のである。
本発明化合物はｎ―ドデシルベンゼン及び３，
３，３―トリフルオロプロペンを出発原料とし、
酸触媒を使用して合成し得る。反応式を下記に示
す。
酸触媒としてHFまたはBF3を使用し得る。
反応方式は連続式またはバツチ式が使用し得、
比較的穏やかな温度条件下で合成を実施し得る。
一例としてバツチ式の場合について説明する。ス
テンレス製オートクレーヴにｎ―ドデシルベンゼ
ン、３，３，３―トリフルオロプロペン及び酸触
媒を導入し、所定反応温度で１乃至30時間反応さ
せる。反応温度は触媒によつて異なり、BF3の場
合０〜50℃、HFの場合は50〜150℃が好ましい範
囲である。反応終了後は反応系から残ガスを排出
し、反応混合物から触媒を除去し、反応混合物を
減圧蒸溜することにより無色透明な液状のｂ―ド
デシル―（３，３，３―トリフルオロプロピル）
ベンゼンを得る。なお、本発明の新規化合物は下
記位置異性体を包含していると思料される。
The present invention discloses a novel compound n-dodecyl-
The present invention relates to (3,3,3-trifluoropropyl)benzene, 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, conventionally, polychlorinated biphenyl has 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 biological degradability, and once it enters the body, it accumulates in the body without being excreted, causing poisoning symptoms, so its use has come to be regulated. Since then, various alternative compounds have been proposed;
No compound, such as polychlorinated biphenyl, which has a high dielectric constant, high insulation resistance, and low dielectric loss tangent, and has excellent biodegradability and does not pollute the natural environment has been proposed. The inventors of the present invention have developed a new compound 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 invention was achieved by synthesizing n-dodecyl-(3,3,3-trifluoropropyl)benzene. The compounds of the present invention include n-dodecylbenzene and 3,
Using 3,3-trifluoropropene as a starting material,
Can be synthesized using acid catalysts. The reaction formula is shown below. HF or BF3 can be used as acid catalyst. 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. N-dodecylbenzene, 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 varies depending on the catalyst, and the preferred range is 0 to 50°C for BF 3 and 50 to 150°C for HF. 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 obtain colorless and transparent liquid b-dodecyl-(3,3,3-trifluoropropyl).
Get benzene. In addition, the novel compound of the present invention is considered to include the following positional isomers.
本発明の化合物は電気特性に優れており、絶縁
体として使用し得、特に絶縁油として利用するこ
とが可能である。
本発明の化合物はそれが有するトリフルオロプ
ロピル基に起因していると思われる優れた誘電率
を有するので、コンデンサ用絶縁油として適用し
得、コンデンサ及びコンデンサを使用する機器の
性能向上及び小型化に寄与することを期待し得
る。
以下、実施例に基づいて本発明をより詳細に説
明する。
実施例
容量１のステンレス製オートクレーヴにｎ―
ドデシルベンゼン369ｇ、３，３，３―トリフル
オロプロペン166ｇを仕込みこれに更にBF3を内
圧が73Kg／・Ｇになるまで圧入し、40℃で撹拌し
ながら18時間反応させた。反応終了後ガスをパー
ジし、内容物をメチレンクロライドで溶かし出
し、常法により水洗、乾燥、次いでメチレンクロ
ライドをロータリーエバレーターで留去した。こ
うして得られた反応混合物を減圧下に精密蒸留
し、沸点154℃／0.8mmＨｇ〜152℃／0.65mmＨｇ
フラクシヨン117ｇを得た。該フラクシヨンはガ
スクロマトグラフイー及び以下に示す分析結果に
より99％以上の純度を有するｎ―ドデシル―
（３，３，３―トリフルオロプロピル）ベンゼン
であることが確認された。
(a) 質量分析（20eV） ｍ／e342
第１図は親ピーク付近の質量スペクトルを示
す。
(b) NMR（CCl4溶液）
1H―NMR δ7.3〜7.0ppm（m4H Ar―Ｈ）
3.2〜1.1ppm（m26H―CH2―）
0.9ppm（t3H―CH3）
19F―NMR内部基準のベンゾトリフルライド
から＋2.7ppm及び＋2.9ppmに
CF3のシグナルが２つのトリプレ
ツトの重なりとして認められた。
(c) 元素分析
実測値（％） 計算値（％）
Ｃ 73.9 73.68
Ｈ 9.6 9.65
Ｆ 16.5 16.67
(d) 赤外線吸収スペクトル
第２図にスペクトルを示す。
(e) 沸 点154℃／0.8mmＨｇ〜152℃／0.65mmＨ
ｇ
(f) 比 重 0.978（20℃）
(g) 屈折率 1.4561（20℃）
次に本発明化合物の20℃に於る電気的性質を第
１表に示す。
第１表
誘電率 3.89
誘電正接（％） 0.015
体積抵抗率（Ω・cm） 8.79×1014 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.
369 g of dodecylbenzene and 166 g of 3,3,3-trifluoropropene were charged, and BF 3 was further pressurized into the mixture until the internal pressure reached 73 kg/·G, and the mixture was reacted at 40° C. with stirring for 18 hours. After the reaction was completed, the gas was purged and the contents were dissolved with methylene chloride, washed with water and dried in a conventional manner, and then methylene chloride was distilled off using a rotary evaporator. The reaction mixture thus obtained was subjected to precision distillation under reduced pressure, with a boiling point of 154℃/0.8mmHg to 152℃/0.65mmHg.
117 g of fraction was obtained. The fraction has a purity of 99% or more as determined by gas chromatography and the analysis results shown below.
It was confirmed to be (3,3,3-trifluoropropyl)benzene. (a) Mass spectrometry (20eV) m/e342 Figure 1 shows the mass spectrum near the parent peak. (b) NMR (CCl 4 solution) 1 H-NMR δ7.3~7.0ppm (m4H Ar-H) 3.2-1.1ppm (m26H-CH 2 -) 0.9ppm (t3H-CH 3 ) 19 F-NMR internal standard benzotrifluride to +2.7ppm and +2.9ppm
The CF 3 signal was recognized as an overlap of two triplets. (c) Elemental analysis Actual value (%) Calculated value (%) C 73.9 73.68 H 9.6 9.65 F 16.5 16.67 (d) Infrared absorption spectrum The spectrum is shown in Figure 2. (e) Boiling point 154℃/0.8mmHg to 152℃/0.65mmH
g (f) Specific gravity 0.978 (20°C) (g) Refractive index 1.4561 (20°C) Table 1 shows the electrical properties of the compounds of the present invention at 20°C. Table 1 Dielectric constant 3.89 Dissipation tangent (%) 0.015 Volume resistivity (Ω・cm) 8.79×10 14
第１図は本発明化合物の質量スペクトルを表わ
し、第２図は本発明化合物の赤外吸収スペクトル
を表わす。
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)
ルオロプロピル）ベンゼン。 ２ ｎ―ドデシルベンゼンと３，３，３―トリフ
ルオロプロペンとを酸触媒の存在下で反応させる
ことを特徴とするｎ―ドデシル―（３，３，３―
トリフルオロプロピル）ベンゼンの製造方法。 ３ 酸触媒がHF又はBF3であることを特徴とす
る特許請求の範囲第２項記載の方法。[Claims] 1 formula n-dodecyl-(3,3,3-trifluoropropyl)benzene represented by 2 n-dodecyl-(3,3,3-
A method for producing benzene (trifluoropropyl). 3. The method according to claim 2, wherein the acid catalyst is HF or BF3 .
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18656380A JPS57112337A (en) | 1980-12-29 | 1980-12-29 | N-dodecyl-(3,3,3-trifluoropropyl)benzene |
| DE3106170A DE3106170C2 (en) | 1980-02-22 | 1981-02-19 | 3,3,3-trifluoropropylated benzene derivatives |
| FR8103389A FR2476638A1 (en) | 1980-02-22 | 1981-02-20 | SUBSTITUTED BENZENE DERIVATIVES HAVING AT LEAST ONE BENZENIC CYCLE SUBSTITUTED BY THE 3,3,3-TRIFLUOROPROPYL GROUP, AND THEIR PREPARATION |
| GB8105501A GB2071087B (en) | 1980-02-22 | 1981-02-20 | Substituted benzene derivative having at least one benzene ring substituted by 3,3,3-trifluoropropyl |
| US06/320,538 US4476328A (en) | 1980-02-22 | 1981-11-12 | Process for producing 3,3,3-trifluoropropyl substituted phenol |
| US06/412,963 US4451674A (en) | 1980-02-22 | 1982-08-30 | Substituted benzene derivatives having at least one benzene ring substituted by 3,3,3-trifluoropropyl group and process for their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18656380A JPS57112337A (en) | 1980-12-29 | 1980-12-29 | N-dodecyl-(3,3,3-trifluoropropyl)benzene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57112337A JPS57112337A (en) | 1982-07-13 |
| JPS6241581B2 true JPS6241581B2 (en) | 1987-09-03 |
Family
ID=16190710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18656380A Granted JPS57112337A (en) | 1980-02-22 | 1980-12-29 | N-dodecyl-(3,3,3-trifluoropropyl)benzene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57112337A (en) |
-
1980
- 1980-12-29 JP JP18656380A patent/JPS57112337A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57112337A (en) | 1982-07-13 |
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