JPH03261731A - Production of 1,1,1,2-tetrafluoroethane - Google Patents
Production of 1,1,1,2-tetrafluoroethaneInfo
- Publication number
- JPH03261731A JPH03261731A JP2059518A JP5951890A JPH03261731A JP H03261731 A JPH03261731 A JP H03261731A JP 2059518 A JP2059518 A JP 2059518A JP 5951890 A JP5951890 A JP 5951890A JP H03261731 A JPH03261731 A JP H03261731A
- Authority
- JP
- Japan
- Prior art keywords
- tetrafluoroethane
- chromium
- catalyst
- hydrogen fluoride
- rearranging
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 15
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 15
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 3
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 3
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 abstract description 8
- 239000002994 raw material Substances 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 7
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052804 chromium Inorganic materials 0.000 abstract description 4
- 239000011651 chromium Substances 0.000 abstract description 4
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 230000006866 deterioration Effects 0.000 abstract description 2
- 239000003507 refrigerant Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000007423 decrease Effects 0.000 description 7
- 238000006462 rearrangement reaction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は１，１．２−テトラフルオロエタンノ製造方法
、特に１，１．２．２−テトラフルオロエタン（以下、
１３４と呼ぶ）をクロム触媒により転位させて１，１，
１．２−テトラフルオロエタン（以下、１３４ａと呼ぶ
）を製造する方法に関するものである。Detailed Description of the Invention [Industrial Field of Application] The present invention relates to a method for producing 1,1,2-tetrafluoroethane, particularly 1,1,2,2-tetrafluoroethane (hereinafter referred to as
134) is rearranged with a chromium catalyst to produce 1,1,
The present invention relates to a method for producing 1,2-tetrafluoroethane (hereinafter referred to as 134a).
［従来の技術］
１３４ａは冷媒として有用な物質であって、これまでに
知られている製造方法として次式の化学反応を利用する
方法がある。[Prior Art] 134a is a substance useful as a refrigerant, and a known method for producing it is one that utilizes the following chemical reaction.
（１）ＣＦ、＝ＣＦＨ十ＨＦ −ＣＦ、ＣＨ，Ｆ（２）
ＣＦ、ＣＨ，ＣＮ＋ＨＦ→ＣＦ、ＣＨ，Ｆしかし、（１
）の反応では原料のトリフルオロエチレンが高価であり
、また、（２）の反応では多量のフッ化水素が必要とさ
れ、転化率が低いなどの欠点もあるので、工業的製造の
ためには一層の検討が必要である。(1) CF, = CFH ten HF - CF, CH, F (2)
CF, CH, CN + HF → CF, CH, F However, (1
In the reaction (2), the raw material trifluoroethylene is expensive, and in the reaction (2), a large amount of hydrogen fluoride is required, resulting in a low conversion rate. Further consideration is required.
他方、ソ連の文献ヌンヤンツ（１，Ｌ、Ｋｎｕｎｙａｎ
ｔｓ）のイズベスティヤ・アカデミ−・ナウク（Ｉｚｖ
ｅｓｔｉｙａ Ａｋａｄｅｍｉｉ Ｎａｕｋ） Ｓ Ｓ
Ｓ Ｒ，１９５８年９０６頁には、テトラフルオロエ
チレンをパラジウム触媒存在下、室温で水素付加するこ
とにより１３４が９６％の収率で得られることが報告さ
れている。ＰＴＦＥの原料であるテトラフルオロエチレ
ンおよび水素は工業的に容易に入手できるので、１３４
を１３４ａに転化する簡単な方法があれば、下記式に示
すような１３４ａを合成するための工業的に画期的な方
法が得られる。On the other hand, the Soviet literature Nunyanz (1, L, Knunyan
ts)'s Izvestiya Academy Nauk (Izv
estiya Akademii Nauk) S S
SR, 1958, p. 906, reports that 134 can be obtained in 96% yield by hydrogenating tetrafluoroethylene at room temperature in the presence of a palladium catalyst. Since tetrafluoroethylene and hydrogen, which are raw materials for PTFE, are easily available industrially, 134
If there is a simple method for converting 134a into 134a, an industrially innovative method for synthesizing 134a as shown in the following formula can be obtained.
ＣＦｔ ＝ ＣＦｔ ＋Ｈｘ”” ＨＣＦｔＣＦｔＨ担
翻彊ＣＦｓＣＨｔＦ［発明が解決しようとする課題］
文献■ミラー（Ｗ、 Ｔ 、 Ｍ ｉ ｌ １ｅｒ）、
ファガー（Ｅ。CFt = CFt +Hx"" HCFtCFtH Converter CFsCHtF [Problem to be solved by the invention] Literature ■Miller (W, T, M i l 1er),
Fagger (E.
Ｗ、 Ｆ ａｇｅｒ）、グリスヴアルト（Ｐ 、 Ｈ、
Ｇ ｒｉｓｗａｌｄ）のジャーナル・オフ・ジ・アメリ
カン・ケミカル・ソサエティ（Ｊｏｕｒｎａｌ ｏｆ
ｔｈｅ Ａ＠ｅｒｉｃａｎ Ｃｈｅｍｉｃａｌ ５ｏｃ
ｉｅｔｙ）第７２巻、７０５頁（１９５０年）または■
ハトリッキー（Ｎ、 Ｈｕｄｌｉｃｋｙ）のコレクショ
ン・オフ・チェコスロバーク・ケミカル・コミュニケー
ションズ（Ｃｏｌｌｅｃｔｉｏｎ ｏｒ Ｃｚｅｃｈｏ
ｓｌ。W, Fager), Griswald (P, H,
Griswald's Journal of the American Chemical Society
the A@erican Chemical 5oc
iety) Vol. 72, p. 705 (1950) or ■
Collection of Czechoslovak Chemical Communications (N, Hudlicky)
sl.
ｖａｋ Ｃｈｅｍｉｃａｌ Ｃｏｍｍｕｍｉｃａｔｉｏ
ｎｓ）第２８巻、２４５５Ｊｍ（１９６３年）に見られ
るようにフッ素と塩素（または臭素）間のハロゲン交換
による転位反応の例はいくつかあるが、フッ素と水素間
の転位反応の例は現在のところ見当らない。vak Chemical Communicatio
ns) Volume 28, 2455 Jm (1963), there are some examples of rearrangement reactions between fluorine and chlorine (or bromine) by halogen exchange, but the current examples of rearrangement reactions between fluorine and hydrogen are I can't find it anywhere.
ＣＣｌ２３
■ ＣＦｙＣ１２ＣＣＩ２ｔＦ ＣＦ３ＣＣ
（！３ｇＣｆｆ３
■ ＣＦ、ＢｒＣＨＦＣＩ２ ＣＦｓＣＨＢ
ｒＣ１２［課題を解決するための手段］
本発明者らは１３４の転位反応による１３４ａの工業的
製造方法を求めて種々研究を重ねた結果、フッ化水素で
処理した酸化クロム（ＩＩＩ）の存在下に１３４を反応
させると転位反応により１３４ａが生成し、さらにフッ
化水素を共存させるとクロム触媒の劣化が著しく抑えら
れることを見出した。CCl23 ■ CFyC12CCI2tF CF3CC
(!3gCff3 ■ CF, BrCHFCI2 CFsCHB
rC12 [Means for Solving the Problems] The present inventors have conducted various studies in search of an industrial production method for 134a by rearrangement reaction of 134, and as a result, in the presence of chromium (III) oxide treated with hydrogen fluoride, It has been found that when 134 is reacted with 134, 134a is produced by a rearrangement reaction, and that when hydrogen fluoride is allowed to coexist, the deterioration of the chromium catalyst is significantly suppressed.
本発明は上記の知見に基づくものであって、その要旨は
、１３４をフッ化水素の存在下、酸化クロム触媒により
転位させることを特徴とする１３４ａの製造方法である
。The present invention is based on the above findings, and its gist is a method for producing 134a, which is characterized by rearranging 134 using a chromium oxide catalyst in the presence of hydrogen fluoride.
本発明において、原料１３４に対するフッ化水素の使用
量は触媒寿命に影響を与える。フッ化水素が１３４に対
して０．２モル以下の場合、または全く共存しない場合
には、クロム触媒表面が炭素で被われ、転化率が急激に
減少し、触媒寿命が非常に短くなる。これは、中間体と
して考えられるトリフルオロエチレンにより炭化したも
のであると考えられる。他方、フッ化水素が０．２モル
より多く共存すると触媒表面への炭化が起こりにくくな
り、触媒寿命が長くなる。フッ化水素の上限は特に限定
されないが、多すぎると原料１３４の濃度が低下し接触
時間が短縮され、転化率が低くなるので、１０モルを越
えることは工業的には好ましくない。In the present invention, the amount of hydrogen fluoride used with respect to the raw material 134 affects the catalyst life. When hydrogen fluoride is less than 0.2 mole per 134, or when it does not coexist at all, the chromium catalyst surface is covered with carbon, the conversion rate decreases rapidly, and the catalyst life becomes extremely short. This is thought to be carbonized by trifluoroethylene, which is considered as an intermediate. On the other hand, if more than 0.2 mol of hydrogen fluoride coexists, carbonization on the catalyst surface becomes difficult to occur and the catalyst life becomes longer. There is no particular upper limit to the amount of hydrogen fluoride, but if it is too large, the concentration of the raw material 134 will be reduced, the contact time will be shortened, and the conversion rate will be low, so it is industrially unfavorable to exceed 10 moles.
本発明において反応温度が低下すると、１３４ａへの反
応速度が小さくなり生産性が低下する。その下限は３０
０’Ｃである。他方、４００’Ｃ以上の高温になると、
原料の熱分解が始まり触媒表面が炭化され、触媒能力が
低下し、経時変化とともに転化率が減少し、さらに１３
４ａの選択率も９２％程度まで低下し、実用性に欠ける
。従って、反応温度範囲は３００’Ｃ〜４００°Ｃで、
好ましくは３２０’Ｃ〜３８０°Ｃである。In the present invention, when the reaction temperature decreases, the reaction rate to 134a decreases and productivity decreases. The lower limit is 30
It is 0'C. On the other hand, when the temperature reaches 400'C or higher,
Thermal decomposition of the raw material begins and the surface of the catalyst becomes carbonized, the catalytic ability decreases, and the conversion rate decreases over time.
The selectivity of 4a also decreases to about 92%, making it impractical. Therefore, the reaction temperature range is 300'C to 400°C,
Preferably it is 320'C to 380C.
反応圧力は特に制限されないか、生産効率の点から通常
大気圧〜１０ ｋｇ／ｃｍ’がよい。接触時間は反応温
度によるが、通常１〜１００９・ｓｅｃ／ｃｃである。The reaction pressure is not particularly limited, and from the viewpoint of production efficiency, it is usually atmospheric pressure to 10 kg/cm'. The contact time depends on the reaction temperature, but is usually 1 to 1009·sec/cc.
ここていう接触時間は触媒重量（Ｗ）を標準状態でのガ
ス重速（Ｆ）で割ったもの（Ｗ／Ｆ）である。The contact time here is the catalyst weight (W) divided by the gas velocity (F) under standard conditions (W/F).
次に実施例を挙げてさらに具体的に本発明を説明する。Next, the present invention will be explained in more detail with reference to Examples.
［発明の効果］
本発明の方法は、高価な原料を用いる必要がなく、フッ
化水素の使用量が少なく、転化率、選択率に優れ、また
触媒寿命が長いという利点を有する。[Effects of the Invention] The method of the present invention has the advantages that it is not necessary to use expensive raw materials, the amount of hydrogen fluoride used is small, the conversion rate and selectivity are excellent, and the catalyst life is long.
［実施例］
以下に実施例を挙げて本発明をさらに具体的に説明する
。[Example] The present invention will be described in more detail with reference to Examples below.
硝酸クロム水溶液にアンモニア水を加えて沈澱させた水
酸化クロムを１１０°Ｃで９時間風乾した後、１〜２．
８１ＩＩの粒径に調製し、その３０ｙを直径２０１１Ｍ
のハステロイＣパイプに充填した。窒素を２００ ｙｚ
Ｑ／’分で流しながら４００℃で６時間加熱した後、さ
らにフッ化水素を２００ ｙｔＱ１分で通しながら、４
００℃で２時間加熱した。このようにして得られた触媒
をフッ化水素処理酸化クロム（ＩＩＩ）として使用した
。After air-drying the chromium hydroxide precipitated by adding ammonia water to the chromium nitrate aqueous solution at 110°C for 9 hours, 1 to 2.
The particle size of 81II was prepared, and the 30y was made into a diameter of 2011M.
filled into Hastelloy C pipe. 200 yz nitrogen
After heating at 400°C for 6 hours while flowing at Q/' min, hydrogen fluoride was further heated at 200 ytQ1 min for 4 hours.
Heated at 00°C for 2 hours. The catalyst thus obtained was used as hydrogen fluoride treated chromium (III) oxide.
実施例１〜１２
上記触媒をハステロイＣ製反応管（長さ１０００ ｚｘ
’）に充填し、電気炉で昇温し、接触時間Ｗ／Ｆを２８
〜４８ｇ・ｓｅｃ／１１Ｑとし、大気圧下、１３４とフ
ッ化水素を第１表に示すモル比で通じ、生成ガスを水洗
塔、アルカリ水洗塔および塩化カルシウム乾燥塔に順次
通した。塩化カルシウム乾燥塔通過後のガスをガスクロ
マトグラフィーで分析した。反応条件と分析結果を第１
表に示す。Examples 1 to 12 The above catalyst was heated in a reaction tube made of Hastelloy C (length 1000 zx
'), heated in an electric furnace, and set the contact time W/F to 28
134 and hydrogen fluoride were passed under atmospheric pressure at a molar ratio shown in Table 1, and the resulting gas was sequentially passed through a water washing tower, an alkaline water washing tower, and a calcium chloride drying tower. The gas after passing through the calcium chloride drying tower was analyzed by gas chromatography. The reaction conditions and analysis results are the first
Shown in the table.
比較例１〜３
反応条件を第１表に示す値に変更したこと以外は実施例
１〜１２と同様にして反応および分析を行った。結果を
第１表に示す。Comparative Examples 1 to 3 Reactions and analyzes were carried out in the same manner as Examples 1 to 12, except that the reaction conditions were changed to the values shown in Table 1. The results are shown in Table 1.
Claims (1)
素の存在下、酸化クロム触媒により転位させることを特
徴する１，１，２，２−テトラフルオロエタンの製造方
法。 ２、１，１，２，２−テトラフルオロエタンとフッ化水
素のモル比が１：０．２〜２０である請求項１記載の１
，１，２，２−テトラフルオロエタンの製造方法。 ３、反応温度を３００〜４００℃とする請求項１または
２記載の１，１，２，２−テトラフルオロエタンの製造
方法。 ４、酸化クロム触媒があらかじめフッ化水素で処理され
ている請求項１〜３のいずれか１項に記載の１，１，２
，２−テトラフルオロエタンの製造方法。[Claims] Production of 1,1,2,2-tetrafluoroethane, characterized by rearranging 1,1,1,2,2-tetrafluoroethane using a chromium oxide catalyst in the presence of hydrogen fluoride. Method. 1 according to claim 1, wherein the molar ratio of 2,1,1,2,2-tetrafluoroethane and hydrogen fluoride is 1:0.2 to 20.
, 1,2,2-Tetrafluoroethane manufacturing method. 3. The method for producing 1,1,2,2-tetrafluoroethane according to claim 1 or 2, wherein the reaction temperature is 300 to 400°C. 4. 1, 1, 2 according to any one of claims 1 to 3, wherein the chromium oxide catalyst is previously treated with hydrogen fluoride.
, 2-Tetrafluoroethane manufacturing method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2059518A JPH03261731A (en) | 1990-03-09 | 1990-03-09 | Production of 1,1,1,2-tetrafluoroethane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2059518A JPH03261731A (en) | 1990-03-09 | 1990-03-09 | Production of 1,1,1,2-tetrafluoroethane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03261731A true JPH03261731A (en) | 1991-11-21 |
Family
ID=13115565
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2059518A Pending JPH03261731A (en) | 1990-03-09 | 1990-03-09 | Production of 1,1,1,2-tetrafluoroethane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03261731A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995015300A1 (en) * | 1993-12-03 | 1995-06-08 | Imperial Chemical Industries Plc | Production of 1,1,1,2-tetrafluoroethane |
| US6232513B1 (en) | 1997-01-17 | 2001-05-15 | Elf Atochem S.A. | Isomerization of hydrofluorocarbon |
| JP2012515215A (en) * | 2009-01-16 | 2012-07-05 | ハネウェル・インターナショナル・インコーポレーテッド | Isomerization of 1,1,3,3-tetrafluoropropene |
-
1990
- 1990-03-09 JP JP2059518A patent/JPH03261731A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995015300A1 (en) * | 1993-12-03 | 1995-06-08 | Imperial Chemical Industries Plc | Production of 1,1,1,2-tetrafluoroethane |
| US6232513B1 (en) | 1997-01-17 | 2001-05-15 | Elf Atochem S.A. | Isomerization of hydrofluorocarbon |
| JP2012515215A (en) * | 2009-01-16 | 2012-07-05 | ハネウェル・インターナショナル・インコーポレーテッド | Isomerization of 1,1,3,3-tetrafluoropropene |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2843693B2 (en) | Method for producing 1,1,1,2-tetrafluoroethane | |
| JP2510127B2 (en) | Fluorination method of perchloroethylene or pentachloroethane | |
| GB2030981A (en) | Process for the preparation of tetrafluorethane | |
| EP1819651A2 (en) | Direct one-step synthesis from cf3-i | |
| KR101331766B1 (en) | Process for producing catalyst for use in producing unsaturated aldehyde and unsaturated carboxylic acid, and process for producing unsaturated aldehyde and unsaturated carboxylic acid | |
| JPH04226927A (en) | Process for producing 1,1,1,2-tetrafluorochloroethane and pentafluoroethane | |
| US3959383A (en) | Two-stage converson of methanol to formaldehyde | |
| JP2020132585A (en) | Method for producing halogenated butene compound | |
| CZ280000B6 (en) | Process for preparing 1,1,1,2-tetrafluoroethane | |
| US3865885A (en) | Catalytic chlorofluorination of isopropyl fluoride to 1,1,2-trichlorotrifluoropropene-1 | |
| JPH03261731A (en) | Production of 1,1,1,2-tetrafluoroethane | |
| JPS6315254B2 (en) | ||
| JP2005254064A (en) | Catalyst for fluorination reaction | |
| RU2072975C1 (en) | Method of synthesis of 1,1,1-trifluorochloroethane and 1,1,1,2-tetrafluoroethane | |
| JP3300120B2 (en) | Method for producing 1,1,1-trifluoro-2-chloroethane | |
| JP2894620B2 (en) | Method for producing hydrogen cyanide | |
| US2399361A (en) | Manufacture of cyanogen | |
| JPH04235146A (en) | Process for preparing n-vinylamide | |
| JPS5841829A (en) | Preparation of octafuoropropane | |
| JP4667674B2 (en) | Method for producing oxidation or ammoxidation catalyst | |
| JPS59118751A (en) | Preparation of fluoroalkylnitrile | |
| JPH0317035A (en) | Production of trifluorochloroethylene | |
| JPH02131438A (en) | Production of hexafluoroethane | |
| JPS6129332B2 (en) | ||
| KR950014215B1 (en) | Preparation of 1,1,1,2-tetrafluoro ethane |