JPS6223728B2 - - Google Patents
Info
- Publication number
- JPS6223728B2 JPS6223728B2 JP53113713A JP11371378A JPS6223728B2 JP S6223728 B2 JPS6223728 B2 JP S6223728B2 JP 53113713 A JP53113713 A JP 53113713A JP 11371378 A JP11371378 A JP 11371378A JP S6223728 B2 JPS6223728 B2 JP S6223728B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- trifluoroethylene
- hydrogen fluoride
- chromium
- chromium oxide
- 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
- 239000003054 catalyst Substances 0.000 claims description 22
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 12
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 12
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 7
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 7
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000001354 calcination Methods 0.000 claims description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910000792 Monel Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 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
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910021563 chromium fluoride Inorganic materials 0.000 description 1
- UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical class FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- -1 oxyfluorides Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は１、１、１、２―テトラフルオロエタ
ンの製造方法に関する。
本発明によればトリフルオロエチレンと弗化水
素とを弗化水素化触媒の存在下、高温度でかつ気
相で反応させることを特徴とする１、１、１、２
―テトラフルオロエタンの製造方法が提供され
る。
本発明で使用される弗化水素化触媒（hydrof―
luorination catalyst）は担体に担持させたものか
あるいは担持させていないものであり得る。
本発明で使用するのに非常に適当な触媒の一つ
は酸化クロムである。
酸化クロム触媒は窒素または空気の如き雰囲気
中で加熱することにより活性化し得る。又触媒は
クロムが酸素原子と弗素原子とを伴つている塩基
性弗化クロムであり得る。特に好ましい触媒は水
酸化クロムペーストを水蒸気で処理しついで好ま
しくは空気中で〓焼することにより得られる酸化
クロムであるが、この処理方法は英国特許第
1307224号明細書に詳細に記載されている。上記
英国特許明細書記載の触媒は、弗化水素を25〜
450℃の温度で少なくとも30分間触媒上に通送し
て予備弗素化することにより得られる。この触媒
は圧縮してペレツトにして、固定床で使用し得
る。別法として、適当な粒子径の触媒を流動床で
使用し得る。使用の際酸化クロム触媒は種々の量
の弗素と結合し、従つて、クロムの酸化物、オキ
シフルオライド、ヒドロキシフルオライドおよび
弗化物からなる複雑な混合物の形で存在し得る。
トリフルオロエチレン１モル当り１〜２モルの
弗化水素を使用することが適当である。弗化水素
とトリフルオロエチレンのモル比をより大きくし
得るが、このモル比が余り大きいことは経済的に
好ましくない。弗化水素とトリフルオロエチレン
のモル比は1.4：１〜1.8：１、例えば1.6：１であ
ることが好ましい。
反応温度は200〜500℃、好ましくは、300〜410
℃であることが適当である。
反応剤の接触時間は１〜15秒である。大気圧ま
たは大気圧を越える圧力を使用し得る。
本発明の方法においては、特に、好ましい条件
下で反応を行つた場合には、トリフルオロエチレ
ンの弗化水素化化合物への転化率が非常に高く、
１、１、１、２―テトラフルオロエタンについて
の選択率も非常に高い。本発明においては、実際
に、弗素化有機化合物への転化率は100％まで達
しまた１、１、１、２―テトラフルオロエタンの
収率は95％以上であり得る。
所望の１、１、１、２―テトラフルオロエタン
は慣用の方法により、例えば排出ガスを水および
水酸化ナトリウム水溶液で洗浄し、乾燥しついで
目的化合物を凝縮させて捕集することにより回収
し得る。
出発原料のトリフルオロエチレンは種々の方法
で製造し得る。例えば、水素とトリフルオロクロ
ルエチレンとを気相中において白金またはパラジ
ウムのごとき水素添加触媒の存在下で反応させる
ことにより製造し得る。他の有用な方法は水素と
１、１、２―トリクロロム―１、２、２―トリフ
ルオロエタンとをパラジウムのごとき水素添加触
媒の存在下で反応させる方法である。
以下に本発明の実施例を示す。
実施例 １
長さ90cm、内径2.5cmの管状ニツケル製反応器
に170ｇの酸化クロム触媒を装入した。上記触媒
は前記英国特許第1307224号明細書記載の方法に
従つて、水酸化クロムペーストを95℃で18時間、
水蒸気で処理しついで340℃で11時間〓焼するこ
とにより調製したものである。ついで触媒を350
℃で４時間弗化水素で予備処理した。管状反応器
は電気炉で加熱した。
弗化水素とトリフルオロエチレンを２種の異つ
たモル比で反応器に通送し、その際、触媒床を
350℃に保持した。有機物質と弗化水素の流率
は、試験１においてはそれぞれ185c.c.／分および
130c.c.／分、試験２においては、それぞれ370c.c.／
分および260c.c.／分そして試験３では触媒床の長
さの半分にわたつて、それぞれ、440c.c.／分およ
び286c.c.／分であつた。
排出ガス中の有機物質の容量％を気―液クロマ
トグラフイーにより測定した。
反応条件および生成物の組成を第１表に示す。
The present invention relates to a method for producing 1,1,1,2-tetrafluoroethane. According to the present invention, trifluoroethylene and hydrogen fluoride are reacted in the presence of a hydrofluorination catalyst at high temperature and in a gas phase 1, 1, 1, 2
- A method for producing tetrafluoroethane is provided. Hydrofluorination catalyst (hydrof-
The luorination catalyst may be supported on a carrier or may be unsupported. One highly suitable catalyst for use in the present invention is chromium oxide. Chromium oxide catalysts can be activated by heating in an atmosphere such as nitrogen or air. The catalyst may also be a basic chromium fluoride in which the chromium is associated with oxygen and fluorine atoms. A particularly preferred catalyst is chromium oxide obtained by treating a chromium hydroxide paste with steam and then calcining it, preferably in air; this process is described in British Patent No.
It is described in detail in the specification of No. 1307224. The catalyst described in the above British patent specifies hydrogen fluoride from 25 to
Obtained by prefluorination by passing over a catalyst for at least 30 minutes at a temperature of 450°C. The catalyst can be compressed into pellets and used in a fixed bed. Alternatively, a catalyst of appropriate particle size may be used in a fluidized bed. In use, the chromium oxide catalysts are combined with varying amounts of fluorine and can therefore be present in the form of complex mixtures of chromium oxides, oxyfluorides, hydroxyfluorides and fluorides. It is appropriate to use 1 to 2 moles of hydrogen fluoride per mole of trifluoroethylene. Although the molar ratio of hydrogen fluoride to trifluoroethylene can be made larger, it is economically undesirable for this molar ratio to be too large. Preferably, the molar ratio of hydrogen fluoride to trifluoroethylene is 1.4:1 to 1.8:1, for example 1.6:1. The reaction temperature is 200-500℃, preferably 300-410℃
It is appropriate that the temperature is ℃. The contact time of the reactants is 1-15 seconds. Atmospheric or superatmospheric pressures may be used. In the method of the present invention, especially when the reaction is carried out under preferable conditions, the conversion rate of trifluoroethylene to a hydrofluorinated compound is very high;
The selectivity for 1,1,1,2-tetrafluoroethane is also very high. In the present invention, the conversion rate to the fluorinated organic compound can actually reach up to 100%, and the yield of 1,1,1,2-tetrafluoroethane can be 95% or more. The desired 1,1,1,2-tetrafluoroethane may be recovered by conventional methods, such as by washing the exhaust gas with water and aqueous sodium hydroxide, drying, and collecting the desired compound by condensation. . The starting trifluoroethylene can be produced in a variety of ways. For example, it can be produced by reacting hydrogen and trifluorochloroethylene in the gas phase in the presence of a hydrogenation catalyst such as platinum or palladium. Another useful method is to react hydrogen with 1,1,2-trichloro-1,2,2-trifluoroethane in the presence of a hydrogenation catalyst such as palladium. Examples of the present invention are shown below. Example 1 A tubular nickel reactor with a length of 90 cm and an inner diameter of 2.5 cm was charged with 170 g of a chromium oxide catalyst. The above catalyst was prepared by heating chromium hydroxide paste at 95°C for 18 hours according to the method described in British Patent No. 1307224.
It was prepared by treating with steam and baking at 340°C for 11 hours. Then the catalyst is 350
Pretreatment with hydrogen fluoride for 4 hours at °C. The tubular reactor was heated in an electric furnace. Hydrogen fluoride and trifluoroethylene are passed through the reactor in two different molar ratios, with the catalyst bed
It was held at 350°C. The organic material and hydrogen fluoride flow rates were 185 c.c./min and 185 c.c./min, respectively, in test 1.
130 c.c./min, and 370 c.c./min in test 2, respectively.
min and 260 c.c./min and in Run 3 over half the length of the catalyst bed were 440 c.c./min and 286 c.c./min, respectively. The volume percent of organic substances in the exhaust gas was measured by gas-liquid chromatography. The reaction conditions and product composition are shown in Table 1.
【表】
実施例 ２
反応器の内径がより大きく（3.8cm）、また“モ
ネル”（“Monel”）製（“Monel”は商標である）
であること以外は実施例１と同様の装置を使用し
た。触媒の量は１Kgであつた。弗化水素とトリフ
ルオロエチレンの流率はそれぞれ、200／時お
よび125／時（ガス状）であつた。
HF：CF2＝CHFのモル比は1.9：１であつた。
接触時間は４秒であつた。
排出ガスを水および水酸化アルカリ水溶液で洗
浄し、集水ポツト（catchpot）に通送して水滴を
捕集して乾燥させた。生成物を凝縮により捕集
し、蒸溜した。
CF3CHFへの転化率は95％であつた。生成物中
には弗素化メタン類および弗素化エタン類は0.5
％しか含まれていなかつた。[Table] Example 2 The reactor has a larger inner diameter (3.8 cm) and is made by “Monel” (“Monel” is a trademark)
The same apparatus as in Example 1 was used except that. The amount of catalyst was 1Kg. The flow rates of hydrogen fluoride and trifluoroethylene were 200/hour and 125/hour (gaseous), respectively. The molar ratio of HF:CF 2 =CHF was 1.9:1. The contact time was 4 seconds. The exhaust gas was washed with water and aqueous alkali hydroxide solution and passed to a catchpot to collect water droplets and dry them. The product was collected by condensation and distilled. The conversion rate to CF 3 CHF was 95%. The amount of fluorinated methane and fluorinated ethane in the product is 0.5
It contained only %.
Claims (1)
ロム触媒の存在下、高温でかつ気相で反応させる
ことを特徴とする１、１、１、２―テトラフルオ
ロエタンの製造方法。 ２ 酸化クロム触媒は水酸化クロムペーストを水
蒸気で処理しついで〓焼することにより得られた
ものである特許請求の範囲第１項記載の方法。 ３ トリフルオロエチレン１モル当り、１〜２モ
ルの弗化水素を使用する特許請求の範囲第１項ま
たは第２項に記載の方法。 ４ トリフルオロエチレン１モル当り1.4〜1.8モ
ルの弗化水素を使用する特許請求の範囲第３項記
載の方法。 ５ 反応温度が200〜500℃である特許請求の範囲
第１項〜第４項のいずれかに記載の方法。 ６ 反応温度が300〜410℃である特許請求の範囲
第５項記載の方法。[Claims] 1. A method for producing 1,1,1,2-tetrafluoroethane, which comprises reacting trifluoroethylene and hydrogen fluoride at high temperature in the gas phase in the presence of a chromium oxide catalyst. . 2. The method according to claim 1, wherein the chromium oxide catalyst is obtained by treating a chromium hydroxide paste with steam and then calcining it. 3. The method according to claim 1 or 2, wherein 1 to 2 moles of hydrogen fluoride are used per mole of trifluoroethylene. 4. The method according to claim 3, wherein 1.4 to 1.8 moles of hydrogen fluoride are used per mole of trifluoroethylene. 5. The method according to any one of claims 1 to 4, wherein the reaction temperature is 200 to 500°C. 6. The method according to claim 5, wherein the reaction temperature is 300 to 410°C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3908877 | 1977-09-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5452012A JPS5452012A (en) | 1979-04-24 |
| JPS6223728B2 true JPS6223728B2 (en) | 1987-05-25 |
Family
ID=10407570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11371378A Granted JPS5452012A (en) | 1977-09-20 | 1978-09-18 | Manufacture of 1*1*1*22tetrafluoroethane |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5452012A (en) |
| AR (1) | AR225276A1 (en) |
| AU (1) | AU519072B2 (en) |
| BE (1) | BE870530A (en) |
| BR (1) | BR7806150A (en) |
| CA (1) | CA1117145A (en) |
| DE (1) | DE2837515A1 (en) |
| ES (1) | ES473516A1 (en) |
| FR (1) | FR2403321A1 (en) |
| GB (1) | GB2004539B (en) |
| GR (1) | GR64019B (en) |
| IT (1) | IT1098853B (en) |
| NL (1) | NL7808881A (en) |
| ZA (1) | ZA784828B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2712732C2 (en) * | 1977-03-23 | 1986-03-13 | Hoechst Ag, 6230 Frankfurt | Process for the production of octafluoropropane |
| JPS5527139A (en) * | 1978-08-14 | 1980-02-27 | Daikin Ind Ltd | Preparation of tetrafluoroethane |
| DE3009760A1 (en) * | 1980-03-14 | 1981-09-24 | Hoechst Ag, 6000 Frankfurt | METHOD FOR PRODUCING HIGH PURITY PARTLY FLUORINATED AETHANES |
| FR2501062A1 (en) * | 1980-12-29 | 1982-09-10 | Ugine Kuhlmann | GAS PHASE FLUORURIZATION CATALYSTS OF ALIPHATIC CHLORINE DERIVATIVES, BASED ON CHROMIUM OXIDE MICROBALLS, AND FLUORURIZATION METHODS USING THE SAME CATALYSTS |
| DE3545625A1 (en) * | 1985-12-21 | 1987-06-25 | Dataprint Datendrucksysteme R | Water-free, liquid recording material |
| IT1230779B (en) * | 1989-07-12 | 1991-10-29 | Ausimont Srl | PROCEDURE FOR PREPARING 1,1,1,2 TETRAFLUOROETHANE. |
| BE1004450A3 (en) * | 1990-06-18 | 1992-11-24 | Solvay | METHOD FOR MANUFACTURING 1,1,1,2-tetrafluoroethane. |
| FR2694556B1 (en) * | 1992-08-05 | 1994-09-23 | Atochem Elf Sa | Process for the purification of 1,1,1,2-tetrafluoroethane. |
| KR960016683B1 (en) * | 1993-12-09 | 1996-12-20 | Korea Inst Sci & Tech | Method of producing fluorization catalyst for preparing 1,1,1,2-tetrafluoroethane |
| US5750808A (en) * | 1995-07-11 | 1998-05-12 | E. I. Du Pont De Nemours And Company | Dehydrohalogenation processes |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3755477A (en) * | 1969-06-27 | 1973-08-28 | Ici Ltd | Process for producing fluorinated hydrocarbons |
| JPS4872105A (en) * | 1971-12-29 | 1973-09-29 | ||
| JPS56142222A (en) * | 1980-03-14 | 1981-11-06 | Hoechst Ag | Manufacture of high purity partially fluorinated ethane |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2669590A (en) * | 1951-08-03 | 1954-02-16 | Allied Chem & Dye Corp | Production of fluorine compounds |
| US2855427A (en) * | 1955-05-24 | 1958-10-07 | American Potash & Chem Corp | Continuous process for preparation of pure methyl borate |
-
1978
- 1978-08-16 GB GB7833506A patent/GB2004539B/en not_active Expired
- 1978-08-23 GR GR57064A patent/GR64019B/en unknown
- 1978-08-24 ZA ZA00784828A patent/ZA784828B/en unknown
- 1978-08-28 DE DE19782837515 patent/DE2837515A1/en active Granted
- 1978-08-29 NL NL7808881A patent/NL7808881A/en not_active Application Discontinuation
- 1978-08-30 AU AU39367/78A patent/AU519072B2/en not_active Expired
- 1978-08-31 AR AR273526A patent/AR225276A1/en active
- 1978-09-15 BE BE190528A patent/BE870530A/en not_active IP Right Cessation
- 1978-09-18 JP JP11371378A patent/JPS5452012A/en active Granted
- 1978-09-18 IT IT27797/78A patent/IT1098853B/en active
- 1978-09-19 BR BR7806150A patent/BR7806150A/en unknown
- 1978-09-19 CA CA000311550A patent/CA1117145A/en not_active Expired
- 1978-09-19 FR FR7826787A patent/FR2403321A1/en active Granted
- 1978-09-20 ES ES473516A patent/ES473516A1/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3755477A (en) * | 1969-06-27 | 1973-08-28 | Ici Ltd | Process for producing fluorinated hydrocarbons |
| JPS4872105A (en) * | 1971-12-29 | 1973-09-29 | ||
| JPS56142222A (en) * | 1980-03-14 | 1981-11-06 | Hoechst Ag | Manufacture of high purity partially fluorinated ethane |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2004539B (en) | 1982-02-10 |
| AU3936778A (en) | 1980-03-06 |
| GR64019B (en) | 1980-01-18 |
| FR2403321B1 (en) | 1984-01-20 |
| BR7806150A (en) | 1979-04-17 |
| ZA784828B (en) | 1979-08-29 |
| GB2004539A (en) | 1979-04-04 |
| FR2403321A1 (en) | 1979-04-13 |
| DE2837515A1 (en) | 1979-03-29 |
| ES473516A1 (en) | 1979-05-01 |
| IT7827797A0 (en) | 1978-09-18 |
| DE2837515C2 (en) | 1989-06-29 |
| IT1098853B (en) | 1985-09-18 |
| CA1117145A (en) | 1982-01-26 |
| JPS5452012A (en) | 1979-04-24 |
| AU519072B2 (en) | 1981-11-05 |
| BE870530A (en) | 1979-03-15 |
| NL7808881A (en) | 1979-03-22 |
| AR225276A1 (en) | 1982-03-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3258500A (en) | Process for fluorinating halohydro-carbons | |
| US5136113A (en) | Catalytic hydrogenolysis | |
| RU1838288C (en) | Method of 1,1,2,2-tetrafluoroethane synthesis | |
| US3087975A (en) | Process for making halogenated organic compounds | |
| JPH0267235A (en) | Production of 1, 1, 1, 2-tetrafluoroethane | |
| JPH10505337A (en) | Method for producing fluorine-containing olefins | |
| JPH04226927A (en) | Process for producing 1,1,1,2-tetrafluorochloroethane and pentafluoroethane | |
| JPS6223728B2 (en) | ||
| JPH05221894A (en) | Preparation of 1,1,1,2,3,3,3-heptafluoro- propane (r227) | |
| CA1119202A (en) | Manufacture of halogenated compounds | |
| US4192822A (en) | Process for producing halogenated hydrocarbons | |
| JPH04211026A (en) | Method for preparation of hydrocarbon containing saturated fluorine but not chlorine | |
| US2615925A (en) | Preparation of olefinic compounds | |
| WO1992013817A1 (en) | Process for the manufacture of halogen-substituted propanes containing hydrogen and at least five fluorine substituents | |
| JPH06256235A (en) | Preparation of 1,1,1,3,3,-pentafluoropropane | |
| JP2540409B2 (en) | Production of pentafluoroethane by hydrogenolysis of chloropentafluoroethane | |
| JPS5821900B2 (en) | Hexafluoropropanone-2 | |
| JP2759196B2 (en) | Method for producing 1,1,1-trifluoro-2-chloroethane | |
| JPH03109336A (en) | Preparation of 1, 1, 1, 2-tetrafluoroethylene | |
| JPH02188538A (en) | Preparation of 1,1-dichloro-1-fluoroethane | |
| US6218587B1 (en) | Catalytic hydrogenolysis | |
| US4155881A (en) | Activation of chromic fluoride catalyst with hydrogen chloride and chlorine | |
| JPH0368526A (en) | Preparation of mixture containing 1-chloro-1- fluoroethylene and vinylidene fluoride by gas-phase contacting disproportionate reaction of 1-chloro-1, 1-difluoroethane | |
| JPH0320231A (en) | Production of 1,1-dichloro-1-fluoroethane | |
| US5679876A (en) | Purification of pentafluoroethane |