JPH04154734A - Production of dichloropentafluoropropane - Google Patents
Production of dichloropentafluoropropaneInfo
- Publication number
- JPH04154734A JPH04154734A JP27533290A JP27533290A JPH04154734A JP H04154734 A JPH04154734 A JP H04154734A JP 27533290 A JP27533290 A JP 27533290A JP 27533290 A JP27533290 A JP 27533290A JP H04154734 A JPH04154734 A JP H04154734A
- Authority
- JP
- Japan
- Prior art keywords
- pentafluoropropane
- reaction
- chlorine
- chloro
- hydrogen
- 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
- 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 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 claims abstract description 8
- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical compound CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- XTRPJEPJFXGYCI-UHFFFAOYSA-N 3-chloro-1,1,1,2,2-pentafluoropropane Chemical compound FC(F)(F)C(F)(F)CCl XTRPJEPJFXGYCI-UHFFFAOYSA-N 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- UHMWWIKRVZTBBR-UHFFFAOYSA-N 1-chloro-1,1,2,2,3-pentafluoropropane Chemical compound FCC(F)(F)C(F)(F)Cl UHMWWIKRVZTBBR-UHFFFAOYSA-N 0.000 claims description 3
- 239000002994 raw material Substances 0.000 abstract description 8
- 239000007791 liquid phase Substances 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- 239000007806 chemical reaction intermediate Substances 0.000 abstract description 2
- 239000012459 cleaning agent Substances 0.000 abstract description 2
- 239000003507 refrigerant Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- 239000004088 foaming agent Substances 0.000 abstract 1
- 239000012808 vapor phase Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 9
- HJRXHKBZNQULJQ-UHFFFAOYSA-N 1,1,1-trichloro-2,2,3,3,3-pentafluoropropane Chemical compound FC(F)(F)C(F)(F)C(Cl)(Cl)Cl HJRXHKBZNQULJQ-UHFFFAOYSA-N 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 101150117004 atg18 gene Proteins 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 description 1
- -1 difluoromethylene unit Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910001055 inconels 600 Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明はジクロロペンタフルオロプロパン（Ｒ２２５）
の製造方法に関するものである。[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to dichloropentafluoropropane (R225)
The present invention relates to a manufacturing method.
ジクロロペンタフルオロプロパン（Ｒ２２５）は従来か
ら用いられてきたフロン類と同様に発泡剤、冷媒、洗浄
剤等の用途が期待される。Dichloropentafluoropropane (R225) is expected to be used as a blowing agent, refrigerant, cleaning agent, etc., similar to conventionally used fluorocarbons.
［従来の技術及び発明が解決しようとする課題］ジクロ
ロペンタフルオロプロパン（Ｒ２２５）の合成ルートと
しては、従来塩化アルミニウムの存在下に１−クロロ−
１，２，２−トリフルオロエチレン等のジフルオロメチ
レン単位を有するエチレンにクロロジフルオロメタン等
を付加させて合成する方法が知られている。しかし、こ
の方法は目的生成物と同時に目的生成物と沸点の近いジ
フルオロメチレン以外のメチレン基を有する反応副生物
を生成するため、純度の高い製品を得るには多段の精製
工程が必要であるという欠点を有している。[Prior art and problems to be solved by the invention] Conventionally, as a synthesis route for dichloropentafluoropropane (R225), 1-chloro-
A synthesis method is known in which chlorodifluoromethane or the like is added to ethylene having a difluoromethylene unit such as 1,2,2-trifluoroethylene. However, this method produces a reaction by-product containing a methylene group other than difluoromethylene, which has a boiling point close to that of the desired product, at the same time as the desired product, so multiple purification steps are required to obtain a highly pure product. It has its drawbacks.
［課題を解決するための手段］
本発明者はジクロロペンタフルオロプロパン（Ｒ２２５
）の効率的製造方法について鋭意検討を行なった結果、
１，１，１，２．２−ペンタフルオロプロパン（Ｒ２４
５ｃ ｂ） 、 Ｉ−クロロ−２，２，３゜３．３−ペ
ンタフルオロプロパン（Ｒ２３５ｃ ｂ）、ｌ−クロロ
−１，１，２，２，３−ペンタフルオロプロパン（Ｒ２
３５ｃｃ）等の含水素ペンタフルオロプロパン（ｃｓ
Ｈａ−ｘ ＣＩＸ Ｆｇ ： Ｘ＝Ｏｏｒ１）を塩
素化することにより、高収率でジクロロペンタフルオロ
プロパン（Ｒ２２５）が得られることを見いだし本発明
を提供するに至ったものである。[Means for Solving the Problem] The present inventor has developed dichloropentafluoropropane (R225
), as a result of intensive research into efficient manufacturing methods.
1,1,1,2,2-pentafluoropropane (R24
5c b), I-chloro-2,2,3°3.3-pentafluoropropane (R235c b), l-chloro-1,1,2,2,3-pentafluoropropane (R2
Hydrogen-containing pentafluoropropane (cs
The inventors have discovered that dichloropentafluoropropane (R225) can be obtained in high yield by chlorinating Ha-x CIX Fg: X=Oor1), leading to the provision of the present invention.
以下、本発明につき実施例とともに詳細に説明する。Hereinafter, the present invention will be described in detail along with examples.
すなわら １．１． ｌ、 ２．２−ペンタフルオロプ
ロパン（Ｒ２４５ｃ ｂ） 、 ｌ−クロロ−２，２，
３，３，３−ペンタフルオロプロパン（Ｒ２３５ｃｂ）
、１−クロロ−１，１，２，２，３−ペンタフルオロプ
ロパン（Ｒ２３５ｃｃ）等の含水素ペンタフルオロプロ
パン（Ｃ３Ｈｓ−ｘ ＣＩＸ Ｆｓ ： Ｘ＝ＯＯｒｌ
）を３００℃≦Ｔ≦５００℃（Ｔは反応温度）の温度範
囲で、或いは光照射下、−５０℃≦Ｔ≦１５０℃（Ｔは
反応温度）の７Ｍ度範囲でペンタフルオロプロパンに対
して４モル当量以内の塩素と反応させると、下式に示す
ようにジクロロペンタフルオロプロパン（Ｒ２２５）が
収率よく生成することを見いだした。In other words 1.1. l, 2,2-pentafluoropropane (R245c b), l-chloro-2,2,
3,3,3-pentafluoropropane (R235cb)
, 1-chloro-1,1,2,2,3-pentafluoropropane (R235cc) and other hydrogen-containing pentafluoropropanes (C3Hs-x CIX Fs: X=OOrl
) for pentafluoropropane in the temperature range of 300℃≦T≦500℃ (T is the reaction temperature), or under light irradiation in the 7M degree range of -50℃≦T≦150℃ (T is the reaction temperature). It has been found that when reacted with 4 molar equivalents or less of chlorine, dichloropentafluoropropane (R225) is produced in good yield as shown in the formula below.
Ｃ１□
Ｃｓ Ｈｓ−−Ｃ１ｘＦｉ−Ｃ３ＨＣ１２ＦＳＸ二〇ｏ
ｒｌ
原料に用いる 含水素ペンタフルオロプロパン （
ｃｓ ）（ｘ−ｘ Ｃ１，Ｆｇ ： Ｘ＝
０ｏｒ１） はいずれも公知の化合物である。C1□ Cs Hs--C1xFi-C3HC12FSX20o
rl Hydrogen-containing pentafluoropropane (
cs ) (xx C1, Fg : X=
0or1) are all known compounds.
塩素と原料の割合は大幅に変動させ得るが、塩素を含水
素ペンタフルオロプロパン（Ｃ３Ｈｚ−Ｍ ＣＩＸ ｉ
−ｔ ： Ｘ：＝Ｏｏｒりに対して４モル以上用いる
と過塩素化された生成物トリクロロペンタフルオロプロ
パン（Ｒ−２１５）の生成量が増える。塩素化を選択的
に行わしめ、目的とするジクロロペンタフルオロプロパ
ン（Ｒ２２５）の選択率を上げる為には塩素の使用量を
含水素ペンタフルオロプロパン（Ｃ３Ｈ３−ＸＣ１，Ｆ
、： Ｘ＝０ｏｒ１）に対して４モル以下にする方が
好ましい。Although the proportions of chlorine and raw materials can vary widely, chlorine can be replaced with hydrogenated pentafluoropropane (C3Hz-M CIX i
-t: When 4 moles or more is used relative to X:=Oor, the amount of the perchlorinated product trichloropentafluoropropane (R-215) produced increases. In order to selectively perform chlorination and increase the selectivity of the target dichloropentafluoropropane (R225), the amount of chlorine used should be changed to hydrogen-containing pentafluoropropane (C3H3-XC1,F
, : X=0or1), it is preferable to make it 4 mol or less.
未反応の原料及び反応中間体はジクロロペンタフルオロ
プロパンと容易に分離可能であり原料として再利用可能
である
反応温度は、熱によりラジカルを発生させる場合は３０
０〜５００℃が好適であり、３００℃以下では反応が進
行しにくく、５００℃以上では過塩素化物トリクロロペ
ンタフルオロプロパン（Ｒ−２１５）及び分解生成物が
増える。Unreacted raw materials and reaction intermediates can be easily separated from dichloropentafluoropropane and can be reused as raw materials.The reaction temperature is 30°C when radicals are generated by heat.
A temperature of 0 to 500°C is suitable; below 300°C, the reaction is difficult to proceed, and above 500°C, the perchloride trichloropentafluoropropane (R-215) and decomposition products increase.
光照射下に反応を行う場合は一５０〜１５０℃が特に好
ましい。When the reaction is carried out under light irradiation, the temperature is particularly preferably from -50 to 150°C.
本発明において反応を液相で行なう場合には溶媒を用い
てもよく、このとき溶媒は、原料であるプロパン類およ
び、さらに溶媒自身が塩素化されにくく原料であるプロ
パン類及び塩素を溶かし込むものであれば特に限定され
ない。例えば、四基、化炭素等が好適である。In the present invention, when the reaction is carried out in a liquid phase, a solvent may be used, and in this case, the solvent is one that dissolves the raw material propane and the solvent itself, which is difficult to chlorinate and dissolves the raw material propane and chlorine. If so, there are no particular limitations. For example, four groups, carbon dioxide, etc. are suitable.
反応圧は、気相で反応する場合は減圧から加圧まで特に
限定されず、液相で行なう場合は原料の含水素ペンタフ
ルオロプロパン類が十分液相に存在するように選べばよ
（、溶媒の種類等によっても異なる。The reaction pressure is not particularly limited when the reaction is carried out in the gas phase, and can range from reduced pressure to increased pressure; when the reaction is carried out in the liquid phase, it should be selected so that the hydrogen-containing pentafluoropropanes as raw materials are sufficiently present in the liquid phase. It also varies depending on the type etc.
［実施例］ 以下、本発明の実施例を示す。[Example] Examples of the present invention will be shown below.
実施例１
一７８℃のコンデンサーを取り付けた１０００ｃｃのガ
ラス製反応器を一５０℃に冷却し、１，１，１，２．２
−ペンタフルオロプロパン３００ ｇ （２，２ｍｏｌ
）を仕込んだ後に、５００Ｗの高圧水銀灯による光照射
下に撹拌を行ないながら、塩素ガス１１２ｇ（１，５ｍ
ｏｌ）を徐々に導入した。６時間反応後、酸分を除去し
た後の生成物をガスクロ及びｔｏＦ−ＮＭＲｌ ’Ｈ−
ＮＭＲを用いて分析した。結果を第１表に示す。Example 1 A 1000 cc glass reactor equipped with a -78°C condenser was cooled to -50°C, and 1,1,1,2.2
-pentafluoropropane 300 g (2.2 mol
), 112 g of chlorine gas (1.5 m
ol) was gradually introduced. After 6 hours of reaction, the product after removing the acid was subjected to gas chromatography and toF-NMRl'H-
Analyzed using NMR. The results are shown in Table 1.
第１表
実施例 ２
１−クロロ−２，２，３，３，３−ペンタフルオロプロ
パン３００ ｇ （１，８ｍｏｌ）と塩素ガス５０ｇ
（０，７ｍｏｌ）を用いた外は、実施例１と同様な方法
で６時間反応した。生成物をガスクロ及び”Ｆ −Ｎ
ＭＲｌ ’Ｈ−ＮＭＲを用いて分析した。結果を第２表
に示す。Table 1 Example 2 300 g (1.8 mol) of 1-chloro-2,2,3,3,3-pentafluoropropane and 50 g of chlorine gas
The reaction was carried out for 6 hours in the same manner as in Example 1 except that (0.7 mol) was used. The product was subjected to gas chromatography and “F-N
Analyzed using MRl'H-NMR. The results are shown in Table 2.
第２表
実施例３
１−クロロ−１，１，２，２，３−ペンタフルオロプロ
パン３００ ｇ （１，８ｍｏｌ）と塩素ガス５０ ｇ
（０，７ｍｏｌ）を用いた外は、実施例１と同様な方
法で６時間反応した。生成物をガスクロ及び１９Ｆ −
Ｎ ＭＲｌ ’Ｈ−ＮＭＲを用いて分析した。結果を第
４表に示す。Table 2 Example 3 300 g (1.8 mol) of 1-chloro-1,1,2,2,3-pentafluoropropane and 50 g of chlorine gas
The reaction was carried out for 6 hours in the same manner as in Example 1 except that (0.7 mol) was used. The product was subjected to gas chromatography and 19F-
Analyzed using NMR1'H-NMR. The results are shown in Table 4.
第３表
実施例４
内径１．２７ｃｍ、長さ２０ｃ＋ｎのインコネル６００
製反応器を４３０℃に保ち、ガス化させた１、 １．１
．２゜２−ペンタフルオロプロパンを１５０ｍ１／分、
塩素ガスを１００ｍ１／分で供給し、連続して４時間反
応した。酸分を除去した後の生成物をガスクロ及び１９
Ｆ−ＮＭＲｌ ’Ｈ−ＮＭＲを用いて分析した。結果を
第３表に示す。Table 3 Example 4 Inconel 600 with inner diameter 1.27 cm and length 20c+n
The reactor was kept at 430℃ and gasified.1, 1.1
．． 2゜2-pentafluoropropane at 150ml/min,
Chlorine gas was supplied at a rate of 100 ml/min, and the reaction continued for 4 hours. The product after removing the acid content was subjected to gas chromatography and 19
Analysis was performed using F-NMR1'H-NMR. The results are shown in Table 3.
第４表 ［発明の効果］Table 4 [Effect of the invention]
Claims (1)
）を３００℃≦Ｔ≦５００℃（Ｔは反応温度）の温度範
囲で、４モル当量以内の塩素と反応させることを特徴と
するジクロロペンタフルオロプロパンの製造方法。 ２、含水素ペンタフルオロプロパン （Ｃ＿３Ｈ＿３＿−＿ｘＣｌ＿ｘＦ＿５：Ｘ＝０ｏｒ１
）を光照射下、−５０℃≦Ｔ≦１５０℃（Ｔは反応温度
）の温度範囲で４モル当量以内の塩素と反応させること
を特徴とするジクロロペンタフルオロプロパンの製造方
法。 ３、含水素ペンタフルオロプロパン （Ｃ＿３Ｈ＿３＿−＿ｘＣｌ＿ｘＦ＿５：Ｘ＝０ｏｒ１
）が、１，１，１，２，２−ペンタフルオロプロパン（
Ｒ２４５ｃｂ）、１−クロロ−２，２，３，３，３−ペ
ンタフルオロプロパン（Ｒ２３５ｃｂ）、１−クロロ−
１，１，２，２，３−ペンタフルオロプロパン（Ｒ２３
５ｃｃ）群から選ばれる化合物である、請求項１又は２
に記載のジクロロペンタフルオロプロパンの製造方法。[Claims] 1. Hydrogen-containing pentafluoropropane (C_3H_3_-_xCl_xF_5: X=0or1
) with up to 4 molar equivalents of chlorine at a temperature range of 300°C≦T≦500°C (T is the reaction temperature). 2. Hydrogen-containing pentafluoropropane (C_3H_3_-_xCl_xF_5: X=0or1
) with up to 4 molar equivalents of chlorine in a temperature range of -50°C≦T≦150°C (T is the reaction temperature) under light irradiation. 3. Hydrogen-containing pentafluoropropane (C_3H_3_-_xCl_xF_5: X=0or1
) is 1,1,1,2,2-pentafluoropropane (
R245cb), 1-chloro-2,2,3,3,3-pentafluoropropane (R235cb), 1-chloro-
1,1,2,2,3-pentafluoropropane (R23
Claim 1 or 2, which is a compound selected from the group 5cc)
The method for producing dichloropentafluoropropane described in .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27533290A JPH04154734A (en) | 1990-10-16 | 1990-10-16 | Production of dichloropentafluoropropane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27533290A JPH04154734A (en) | 1990-10-16 | 1990-10-16 | Production of dichloropentafluoropropane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04154734A true JPH04154734A (en) | 1992-05-27 |
Family
ID=17553990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27533290A Pending JPH04154734A (en) | 1990-10-16 | 1990-10-16 | Production of dichloropentafluoropropane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04154734A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5421971A (en) * | 1993-09-03 | 1995-06-06 | Alliedsignal Inc. | Hydrochlorofluorocarbons and hydrofluorocarbons and methods for producing the same |
| JP2005510549A (en) * | 2001-11-27 | 2005-04-21 | ハネウェル・インターナショナル・インコーポレーテッド | Photochlorination of 1,1,1,3,3-pentafluoropropane |
-
1990
- 1990-10-16 JP JP27533290A patent/JPH04154734A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5421971A (en) * | 1993-09-03 | 1995-06-06 | Alliedsignal Inc. | Hydrochlorofluorocarbons and hydrofluorocarbons and methods for producing the same |
| JP2005510549A (en) * | 2001-11-27 | 2005-04-21 | ハネウェル・インターナショナル・インコーポレーテッド | Photochlorination of 1,1,1,3,3-pentafluoropropane |
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