JPH02209824A - 2,2-dichloro-1,1,1,3,3-pentafluoropropane - Google Patents
2,2-dichloro-1,1,1,3,3-pentafluoropropaneInfo
- Publication number
- JPH02209824A JPH02209824A JP2856489A JP2856489A JPH02209824A JP H02209824 A JPH02209824 A JP H02209824A JP 2856489 A JP2856489 A JP 2856489A JP 2856489 A JP2856489 A JP 2856489A JP H02209824 A JPH02209824 A JP H02209824A
- Authority
- JP
- Japan
- Prior art keywords
- pentafluoropropane
- dichloro
- dichlorofluoromethane
- acid type
- lewis acid
- 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.)
- Pending
Links
- JEWUXLHWYRSHJK-UHFFFAOYSA-N 2,2-dichloro-1,1,1,3,3-pentafluoropropane Chemical compound FC(F)C(Cl)(Cl)C(F)(F)F JEWUXLHWYRSHJK-UHFFFAOYSA-N 0.000 title abstract description 3
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 abstract description 8
- 229940099364 dichlorofluoromethane Drugs 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract description 6
- 150000004820 halides Chemical class 0.000 abstract description 6
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002841 Lewis acid Substances 0.000 abstract description 5
- 150000007517 lewis acids Chemical class 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 3
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 abstract description 2
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- COAUHYBSXMIJDK-UHFFFAOYSA-N 3,3-dichloro-1,1,1,2,2-pentafluoropropane Chemical compound FC(F)(F)C(F)(F)C(Cl)Cl COAUHYBSXMIJDK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、溶剤として有用な２，２−ジクロロ−１゜１
、１．３．３−ペンタフルオロプロパンに関するもので
ある。Detailed Description of the Invention [Industrial Application Field] The present invention provides 2,2-dichloro-1゜1 which is useful as a solvent.
, 1.3.3-pentafluoropropane.
［従来の技術］
本特許出願で開示する２、２−ジクロロ−１，１，１，
３゜３−ペンタフルオロプロパンはこれまで知られてい
ない新規化合物である。[Prior art] 2,2-dichloro-1,1,1, disclosed in this patent application
3°3-Pentafluoropropane is a new compound that has not been previously known.
［発明の目的］
本発明の目的は、新規なハイドロクロロフルオロプロパ
ンを提供することにあり、成層ｍ＊で達してオゾン層を
破壊することのない、溶剤として有用な２．２−ジクロ
ロ−１，１，１，３，３−ペンタフルオロプロパンを提
供することにある。[Object of the invention] The object of the present invention is to provide a new hydrochlorofluoropropane, which is useful as a solvent and does not reach stratification m* and destroy the ozone layer. , 1,1,3,3-pentafluoropropane.
［発明の構成］
本発明は式（１）で示される２、２−ジクロロ−１゜１
、１．３．３−ペンタフルオロプロパンを提供するもの
である。[Structure of the invention] The present invention provides 2,2-dichloro-1゜1 represented by formula (1)
, 1.3.3-pentafluoropropane.
（Ｉ） ＣＦ３ＣＣ見ｔ ＣＨＦ ２本発明の式
（１）の２．２−ジクロロ−１，１，１，３，３−ペン
タフルオロプロパンは、例えば、四フッ化エチレンとジ
クロロフルオロメタンとをルイス酸型酸性ハロゲン化物
の存在下に反応させることにより生成する。(I) CF3CC t CHF 2 The 2,2-dichloro-1,1,1,3,3-pentafluoropropane of the formula (1) of the present invention is, for example, a Lewis compound of tetrafluoroethylene and dichlorofluoromethane. It is produced by reacting in the presence of an acid type acid halide.
この製法において四フッ化エチレンとジクロロフルオロ
メタンとの反応は溶媒の共存下に行ってもよいが、反応
は無水の条件下で行なうことが好ましく、例えば１．乾
燥した窒素雰囲気中で行い、溶媒を用いる場合は、十分
に乾燥したものを用いる。溶媒としては、例えばクロロ
ホルム、１．１−ジクロロ−２，２，３，３，３−ペン
タフルオロプロパン、Ｒ−１１３等のハイドロクロロカ
ーボン、ハイドロクロロフルオロカーボン、クロロフル
オロカーボンを使用することができる。In this production method, the reaction between tetrafluoroethylene and dichlorofluoromethane may be carried out in the presence of a solvent, but it is preferable to carry out the reaction under anhydrous conditions, for example 1. It is carried out in a dry nitrogen atmosphere, and if a solvent is used, it should be sufficiently dried. As the solvent, for example, hydrochlorocarbons such as chloroform, 1,1-dichloro-2,2,3,3,3-pentafluoropropane, and R-113, hydrochlorofluorocarbons, and chlorofluorocarbons can be used.
この反応における四フッ化エチレンの量はジクロロフル
オロメタン１モルに対し０．５から１．０モル用いるこ
とが好ましく、ルイス酸型酸性ハロゲン化物の量はジク
ロロフルオロメタンの３〜３０重量％重景が好ましい０
反応は、温度−１０〜１０℃、圧力４〜１０）ｃｇ／ａ
ａにおいて５〜６時間時間性なうとよい０通常、ジクロ
ロフルオロメタンとルイス酸型酸性ハロゲン化物を攪拌
しながら四フッ化エチレンを逐次添加するとよい、ルイ
ス酸型酸性ハロゲン化物としては、例えば、塩化アルミ
ニウム、塩化鉄、等があげられる。得られた反応混合物
から目的生成物を分離するには、例えば、反応混合物に
過剰の水を添加して水洗した後蒸留する。このようにし
て ２．２−ジクロロ−１，１，１゜３．３−ペンタフ
ルオロプロパンを得ることができる。The amount of tetrafluoroethylene in this reaction is preferably 0.5 to 1.0 mol per 1 mol of dichlorofluoromethane, and the amount of Lewis acid type acid halide is 3 to 30% by weight of dichlorofluoromethane. is preferably 0
The reaction was carried out at a temperature of -10 to 10°C and a pressure of 4 to 10) cg/a.
It is best to wait for 5 to 6 hours in a for 5 to 6 hours.Normally, it is preferable to add tetrafluoroethylene sequentially while stirring dichlorofluoromethane and Lewis acid type acid halide.As Lewis acid type acid halide, for example, chloride Examples include aluminum, iron chloride, etc. In order to separate the target product from the obtained reaction mixture, for example, excess water is added to the reaction mixture, the mixture is washed with water, and then distilled. In this way, 2,2-dichloro-1,1,1°3,3-pentafluoropropane can be obtained.
次に、本発明を実施例により詳細に説明する。Next, the present invention will be explained in detail using examples.
［実施例コ
実施例１
内容積１ｔのオートクレーブに塩化アルミニウム３５ｇ
とジクロロフルオロメタン５７０ｇを仕込み、０℃で約
１時間攪拌後、テトラフルオロエチレン４００ｇを系内
の圧力を５ｋｇ／ｄに保ちながら約４時間かけて逐次添
加した。添加終了後さらに０℃に保って１時間攪拌した
。得られた反応混合物を水洗して塩化アルミニウムを除
いた後、蒸留することにより沸点５１℃の無色透明な液
体を７０ｇ得な、こ°の液体を核磁気共鳴スペクトル（
ＮＭＲ）を用いて分析した結果から２．２−ジクロロ−
１，１，１，３，３−ペンタフルオロプロパンと同定さ
れた。[Example Example 1 35 g of aluminum chloride was placed in an autoclave with an internal volume of 1 t.
and 570 g of dichlorofluoromethane were charged, and after stirring at 0° C. for about 1 hour, 400 g of tetrafluoroethylene was added sequentially over about 4 hours while maintaining the pressure in the system at 5 kg/d. After the addition was completed, the mixture was kept at 0°C and stirred for 1 hour. The resulting reaction mixture was washed with water to remove aluminum chloride, and then distilled to obtain 70 g of a colorless and transparent liquid with a boiling point of 51°C.This liquid was analyzed by nuclear magnetic resonance spectroscopy (
From the results of analysis using NMR), 2,2-dichloro-
It was identified as 1,1,1,3,3-pentafluoropropane.
ＮＭＲ分析
＜”ＦＮＭＲ＞ δｐｐｍ ｆｒｏｍ ＣＦ Ｃ１
ｓ＜’ＨＮＭＲ＞
［発明の効果］
本発明の新規物質である２、２−ジクロロ−１，１゜１
、３．３−ペンタフルオロプロパンは、不燃性で従来の
フロンが有している優れた特性に加え、オゾン破壊能が
低く、溶剤として有用である。NMR analysis <”FNMR> δppm from CF C1
s<'HNMR> [Effect of the invention] 2,2-dichloro-1,1゜1, which is a new substance of the present invention
, 3.3-pentafluoropropane is nonflammable and has the excellent properties of conventional chlorofluorocarbons, as well as low ozone depletion ability, making it useful as a solvent.
Claims (1)
，１，３，３−ペンタフルオロプロパン。 （ I ）ＣＦ＿３ＣＣｌ＿２ＣＨＦ＿２[Claims] 2,2-dichloro-1,1 represented by structural formula (I)
, 1,3,3-pentafluoropropane. (I) CF_3CCl_2CHF_2
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2856489A JPH02209824A (en) | 1989-02-09 | 1989-02-09 | 2,2-dichloro-1,1,1,3,3-pentafluoropropane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2856489A JPH02209824A (en) | 1989-02-09 | 1989-02-09 | 2,2-dichloro-1,1,1,3,3-pentafluoropropane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02209824A true JPH02209824A (en) | 1990-08-21 |
Family
ID=12252137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2856489A Pending JPH02209824A (en) | 1989-02-09 | 1989-02-09 | 2,2-dichloro-1,1,1,3,3-pentafluoropropane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02209824A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5102469A (en) * | 1990-02-28 | 1992-04-07 | Kali-Chemie Ag | Dichloropentafluoropropane-containing compositions for removing water from surfaces |
-
1989
- 1989-02-09 JP JP2856489A patent/JPH02209824A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5102469A (en) * | 1990-02-28 | 1992-04-07 | Kali-Chemie Ag | Dichloropentafluoropropane-containing compositions for removing water from surfaces |
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