EP0714384A1 - Procede de combinaison de molecules chlorees pour la synthese de produits fluores - Google Patents

Procede de combinaison de molecules chlorees pour la synthese de produits fluores

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Publication number
EP0714384A1
EP0714384A1 EP94925790A EP94925790A EP0714384A1 EP 0714384 A1 EP0714384 A1 EP 0714384A1 EP 94925790 A EP94925790 A EP 94925790A EP 94925790 A EP94925790 A EP 94925790A EP 0714384 A1 EP0714384 A1 EP 0714384A1
Authority
EP
European Patent Office
Prior art keywords
group
cfc
chosen
catalyst
fluorine
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.)
Withdrawn
Application number
EP94925790A
Other languages
German (de)
English (en)
Inventor
Russell Ward Johnson
Wendy Christine Moeller
Michael Van Der Puy
Mark Kaiser
Li Wang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Honeywell International Inc
Original Assignee
AlliedSignal Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by AlliedSignal Inc filed Critical AlliedSignal Inc
Publication of EP0714384A1 publication Critical patent/EP0714384A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/01—Acyclic saturated compounds containing halogen atoms containing chlorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
    • C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine

Definitions

  • chlorofluorocarbons are widely used for applications such as blowing agents, solvents, refrigerants, propellants, cooling fluids, working fluids, and rinse agents.
  • CFCs are sufficiently stable to diffuse into the stratosphere, where they are eventually decomposed into reactive chlorine-containing radicals. These radicals have been found to catalytically decompose the protective ozone layer.
  • R and R 1 are chosen from the group consisting of halogens, halogenated hydrocarbons, and hydrocarbons, and at least one of R and R' contains fluorine, a and d are integers from 1 to 3, b, c, e, and f are integers from 0 to 2, the sum of a, b, and c is 3, and the sum of d, e, and f is 3, and further treating the coupled products with hydrogen or a fluorinating agent.
  • Examples of the chlorine-containing reactants, RCCl t F b H c and R'CCl d F ⁇ H f are FC1 2 C-CC1F 2 , F 3 C-CC1 3 , F 3 C-CF 2 -CC1 3 , F 3 C-CF 2 -CHC1 2 , CF 2 C1 2 , F 3 C-CHC1 2 , F 3 C-CH 2 C1.
  • F ⁇ CR' are F 3 C-CH 2 -CH 2 -CF 3 , F 2 CH-CHF-CHF-CHF 2 , F 3 C-CH 2 -CH 2 -CH 2 -CF 3 , F 3 C-CH 2 -CHF 2 , and F 3 C-CF 2 -CH 2 -CH 2 -CF 2 -CF 3 .
  • Figure 1 is the gas chromatographic spectrum of the products of the synthesis of CFC-151-10 from CFC-215.
  • the ordinant shows the total ion current from the mass spectroscopy detector and the abscissa represents the retention time of the gas chromatograph.
  • Figure 2 shows the mass spectroscopy fragmentation pattern for one of the products in the spectrum in Figure 1.
  • Figure 3 provides an interpretation of the mass spectroscopy fragmentation pattern of Figure 2 to verify the intermediate product composition.
  • Figure 4 is the gas chromatographic spectrum of the products of the synthesis of HFC-55-10 from CFC- 215.
  • Figure 5 is the mass fragmentation pattern for the peak in Figure 4 that has been assigned to HFC- 55-10.
  • chlorofluoro- carbons can be abated by substituting relatively more fluorine and less chlorine into the compounds and by introducing hydrogen to make the compounds more reactive at lower altitudes.
  • Substituting fluorine for the chlorine of traditional CFC products decreases the boiling point. It is therefore generally necessary to increase the number of carbon atoms in the molecule to achieve the product boiling points required by the applications.
  • the synthesis of the traditional CFC molecules such as dichlorodifluoromethane (CFC-12) , chlorotrifluoromethane (CFC-13) , and trichlorofluoro- methane (CFC-11) are relatively easy and can be produced in concert with each other.
  • HFC higher carbon number hydrofluorocarbons
  • This invention discloses an efficient method for manufacturing advanced HFC and other products such as blowing agents, solvents, refrigerants, propellants, cooling fluids, working fluids, and rinse agents.
  • the inventive process involves preparing the fluorine-containing product RCF b H cl . 1 H f+d . 1 F ⁇ CR' by coupling two chlorine-containing reactants, RCCl a F b H c and R'CCl d F ⁇ H f in the presence of hydrogen and a first catalyst, and further treating the coupled products with hydrogen or a fluorinating agent, optionally in the presence of a second catalyst, to form the fluorine-containing product.
  • R and R' are chosen from the group consisting of halogens, halogenated hydrocarbons, and hydrocarbons, and at least one of R and R' contains fluorine, a and d are integers from 1 to 3, b, c, e, and f are integers from 0 to 2, the sum of a, b, and c is 3, and the sum of d, e, and f is 3.
  • R and R' may have functional groups or other moieties that contain oxygen, nitrogen, sulfur, phosphorous, iodine, bromine, or other components which are not directly involved in the coupling. These functional groups or moieties may be used to enhance application properties or to mask certain reactive sites during the synthesis process.
  • R and R* are -CF 3 , - CC1 2 F, -CF 2 CF 3 , -F, or -Cl, chlorine- and fluorine- containing alkyl groups, chlorine- and fluorine- containing aromatic compounds.
  • the invention also contemplates a process for preparing the fluorine-containing products comprising combining the two chlorine-containing reactants in the presence of hydrogen and a catalyst to form at least one intermediate, RCF ⁇ Cl ⁇ Cl j H ⁇ R' , and subsequently treating the intermediate in the presence of an optional second catalyst with either a fluorinating agent, or with hydrogen and a catalyst to form the fluorine-containing product, wherein the sum of g, h, and i is an integer from 1 to 2, the sum of j, k, and 1 is an integer from 1 to 2, g, h, i, j, k, and 1 are integers from 0 to 1.
  • the catalyst used in the coupling reaction is a group VIII metal and may be chosen from the group consisting of nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, iron, or cobalt.
  • the catalyst may be dispersed on a high surface area support such as alumina, carbon, chromium oxide, chromium oxyfluoride, chromium fluoride, or may be used as an unsupported high surface area metal oxide, metal fluoride, or elemental metal.
  • the preferred catalyst for the coupling reaction is a reduced ruthenium catalyst dispersed on a high surface area support such as alumina or carbon.
  • the molar ratio of hydrogen to reactant in the coupling reaction may vary from 0.5 to about 10.
  • the pressure may vary from ambient to about 1,000 psig, and the liquid hourly space velocity (LHSV) may vary from about 0.1 to about 10.
  • the reaction may be carried out at temperatures in the range of from about 20*C to about 500 *C, preferably in the range of from about 100'C to about 250*C, and most preferably in the range of from about 150*C to about 200*C. Substantial reaction occurs to produce substantial conversion and selectivity at temperatures below 200*C.
  • the catalyst selected for the hydrogen treatment may be the same catalyst used for the coupling reaction or may be selected from metals known to provide substantial hydrogenolysis activity on high surface area supports such as alumina or carbon.
  • the most preferred metals include group VIII metals such as platinum, cobalt, nickel, iridium, ruthenium and palladium which may be modified by promoters including but not limited to rhenium, iridium, cobalt, and nickel.
  • the metals may be attenuated by components including but not limited to sulfur, germanium, or tin.
  • the hydrogenation reaction may be carried out at a liquid hourly space velocity (LHSV) in the range of from about 0.05 to about 10, preferably in the range of from about 0.2 to about 1.0, a temperature in the range of from about 20"C to about 550*C, preferably 100'C to about 350"C, and a pressure in the range of from about 0 psig to about 2000 psig, preferably about 30 psig to about 300 psig.
  • LHSV liquid hourly space velocity
  • the fluorinating agent may be chosen from the group consisting of hydrogen fluoride, uranium fluoride, elemental fluorine, or fluoride salts.
  • fluoride salts are potassium fluoride, sodium fluoride, and cesium fluoride.
  • the catalysts for hydrofluorination may be a chromium-based heterogeneous system, a catalyst system based on liquid-phase contact with antimony pentahalide in hydrogen fluoride, or electrofluorination in hydrogen fluoride.
  • the hydrofluorination reaction may be carried out at a liquid hourly space velocity (LHSV) in the range of from about 0.05 to about 5, preferably in the range of from about 0.1 to about 1.0, a temperature in the range of from about 100*C to about 450*C, preferably 250*C to about 350*C, and a pressure in the range of from about 0 psig to about 500 psig, preferably about 50 psig to about 200 psig.
  • LHSV liquid hourly space velocity
  • the reaction is preferably carried out without a catalyst and at temperatures in the range of from about -50"C to about +100*C, preferably -20*C to about +20*C.
  • the acid nature of the support may be removed with a basic substance such as an alkali metal to avoid unwanted acid-catalyzed isomerizations.
  • a basic substance such as an alkali metal
  • lithium, sodium, or potassium may be added to the alumina for either or both of the reactions.
  • novel fluorine-containing products may be synthesized by first coupling the chlorine-containing reactants in the presence of hydrogen and a catalyst to form an intermediate compound, isolating the intermediate by procedures such as distillation, membranes, absorbents or other separation devices, and then treating the intermediate with hydrogen, a fluorinating agent such as elemental fluorine, or a hydrofluorinating agent such as hydrogen fluoride with an optional second catalyst to form the fluorine- containing product.
  • the fluorine- containing product may be synthesized and further treated with hydrogen or a fluorinating agent without isolation of an intermediate in a single reactor or a series of reactors.
  • a heat exchanger may be used with the series of reactors to adjust temperature.
  • the reactions leading to the fluorine- containing products produce HCl and are therefore very exothermic.
  • the hydrochloric acid may be neutralized, recovered as a byproduct, discarded, or converted into chlorine using the Deacon reaction for recycle or sale.
  • the excess heat must be managed in order to control the reactor temperature profile. Although very high reactor temperatures lead to high reaction rates, they also lead to loss of product selectivity. Heat dispersing techniques such as quench hydrogen, inert fluids such as nitrogen, and/or product recycle streams may be used to provide adequate thermal management.
  • fluorine-containing products may be synthesized by combining a chlorine- containing reactant using an excess of hydrogen and a suitable catalyst to form an intermediate, then a product, or to form a product directly.
  • An intermediate may be a saturated compound or an olefin.
  • An olefin may be hydrogenated to form the desired product using catalytic hydrogenation. Examples of possible syntheses are as follows:
  • HFC- 356mff (1,1,1,4,4,4-hexafluorobutane) may be synthesized using CFC-113 (l,l,2-trichloro-l,2,2-tri- fluoroethane) in the presence of a catalyst sufficiently acidic to cause an iso erization to CFC- 113a.
  • the catalyst CrF 3 may be physically mixed in with a ruthenium catalyst or itself impregnated with ruthenium. The entire reaction may be carried out without the isolation of any intermediate in a single reactor or a series of reactors.
  • CFC-113 rearranges to form CFC-113a and then couples to form the desired HFC-356mff.
  • the four-carbon olefin is hydrogenated to form the desired product using catalytic hydrogenation.
  • HFC-356mff from CFC-113a.
  • HFC- 356mff (1,1,1,4,4,4-hexafluorobutane) may be synthesized by coupling CFC-113a (1,1,1-trichloro- 2,2,2-trifluoroethane) without isolating any intermediates in a single reactor or a series of reactors.
  • the olefin may then be hydrogenated to form HFC-356mff or may be converted to a second intermediate, HCFC-336 (F 3 CCHC1CHC1CF 3 ) .
  • the second intermediate can then be reacted with hydrogen to produce the desired HFC-356mff product.
  • HFC-338 (1,1,1-2,3,4,4,4-octafluorobutane) may be synthesized by coupling CFC-113a (l,l,l-trichloro-2,2,2- trifluoroethane) to form a four-carbon olefin intermediate (CFC-1316mxx, F 3 CCC1-CC1CF 3 ) .. The intermediate may then be hydrogenated to form a second intermediate product (HCFC-336, F 3 CCHC1CHC1CF 3 ) using catalytic hydrogenation and relatively mild conditions.
  • the second intermediate can then be reacted with HF over a suitable catalyst such as a Cr-based heterogeneous system, a catalyst system based on liquid-phase contact with antimony pentahalide in HF, or electrofluorination in HF to produce the desired HFC-338 product.
  • a suitable catalyst such as a Cr-based heterogeneous system, a catalyst system based on liquid-phase contact with antimony pentahalide in HF, or electrofluorination in HF to produce the desired HFC-338 product.
  • HFC-356mff may also be co-produced with HFC-338 by coupling CFC-113a and the ratio of the products can be adjusted by varying the reactor process conditions. Co-production is expected to enhance the economics relative to the production of either product alone.
  • HFC-356mff and/or FC-31-10 from CFC-113a.
  • HFC-356mff and/or FC-31-10 perfluorobutane
  • CFC-316 F 3 CCC1 2 CC1 2 CF 3
  • CFC-316 can then be electrofluorinated in HF to produce FC-31- 10 or treated with hydrogen to produce HFC-356mff.
  • HFC-356mff and FC-31-10 may be co-produced by coupling CFC-316 and the ratio of the products can be adjusted by varying the reactor process conditions.
  • the olefin may then be partially hydrodechlorinated to form HFC-346mdf.
  • CFC-1418 (2,3-dichlorooctafluoro-2-pentene) may be synthesized by reductively coupling CFC-113a and CFC-215 (CF 3 CF 2 CC1 3 ) .
  • CFC-1418 may be further treated, e.g., hydrodechlorinated and/or fluorinated, to form other products, e.g., CFC-43-10 (1,1,1,2,2,3,4,5,5,5- decafluoropentane) , HFC-458 (1,1,1,2,2,5,5-octafluoro- pentane) , or FC-41-12 (perfluoropentane) .
  • CFC-1418 may be synthesized by reductively coupling CFC-113a and CFC-225 (l,l-dichloro-2,2,3,3,3- pentafluoropropane) .
  • CFC-1418 may be further treated as discussed above.
  • the olefin is hydrogenated to form the desired product using catalytic hydrogenation.
  • a high ratio of CFC- 12:CFC-113a is preferred in the charge stock to promote cross-coupling and reduce coupling of two CFC-113a molecules.
  • HFC-356mff and/or HFC-338 may be synthesized by coupling CFC-123 (l,l-dichloro-2,2,2-trifluoro- ethane) to form a four-carbon intermediate (HCFC-336, F 3 CCHC1CHC1CF 3 ) .
  • the intermediate is then hydrodechlorinated to form the desired product using catalytic hydrogenation.
  • HFC-245fa from CFC-12 and CFC- 123.
  • HFC-123 As the reductive coupling reaction of CFC-123 appears to be much faster than the reductive coupling reaction of CFC-12, a high ratio of CFC-12:CFC-123 would be preferably used in the charge stock to promote cross- coupling and reduce coupling of two CFC 123 molecules.
  • HFC- 356mff may be synthesized by reductively coupling HCFC- 133a (l-chloro-2,2,2-trifluoroethane) .
  • HCFC-558 and HFC-578 from CFC- 214.
  • HCFC-558 C1CF 2 CF 2 CH 2 CH 2 CF 2 CF 2 C1
  • HFC-578 HCF 2 CF 2 CH 2 CH 2 CF 2 CF 2 H
  • CFC- 214 C1CF 2 CF 2 CC1 3
  • the olefin may then be hydrogenated to form the desired products using catalytic hydrogenation.
  • CFC-51-10 may then be further treated, e.g., hydrodechlorinated, to form another product, e.g., CFC-55-10.
  • HFC-55-10 from CFC-225.
  • HFC-55- 10 may be synthesized by reductively coupling CFC-225 (1,l-dichloro-2,2,3,3,3-pentafluoropropane) to formthe intermediate HFC-153-10 (1,1,1,2,2,5,5,6,6,6-deca- fluoro-3-hexene) .
  • the olefin is then hydrogenated to form the desired product using catalytic hydrogenation.
  • Example 1 Synthesis of HFC-356mff from CFC-113a
  • the following data were obtained using a microreactor consisting of a syringe pump driven liquid feed system, a mass flow meter controlled hydrogen addition system, a reactor, a reactor outlet effluent sampling system, and an on-line/off-line GC/MS analytical system.
  • the area under the peaks in a plot of the total ion current (TIC) from the GC/MS as a function of retention time provides an estimate of the concentration of the effluent from the reactor.
  • CFC- 113a was the reactant and the catalyst used was 2% ruthenium on carbon. The results shown in Table I provide the product analysis.
  • HFC-356mff was synthesized by loading a single reactor sequentially with 10 mL of a 2% ruthenium catalyst on a carbon support and 10 mL of a
  • HFC-356mff was synthesized from CFC-123 using the microreactor of Example 1.
  • the GC/MS results show a high yield to the four-carbon intermediate.
  • the data shown in Table III provide the conversion and selectivity as functions of temperature.
  • the reactant was CFC-123 and the catalyst was 10% ruthenium on alumina. These data were obtained at 2 LHSV, 10:1 H 2 :CFC-123 molar ratio, and 30 psig pressure as a function of temperature. It can be clearly seen that HCFC-336 (CF 3 CHC1CHC1CF 3 ) can be produced in this manner. Further refinements in the process conditions will lead to an increasing concentration of this product.
  • HFC-55-10 was synthesized from CFC-215 using the microreactor of Example 1.
  • CFC-215 was the reactant and the catalyst was 15% ruthenium on alumina.
  • the data shown in Figure 1 represent the total ion current (TIC) from the GC/MS at a 197*C maximum reactor temperature.
  • Figure 3 provides an analysis of the MS fragmentation pattern to verify the intermediate product composition. The.GC/MS results show a high yield to CFC-151-10, which is the desired four-carbon intermediate.
  • HFC-55-10 The synthesis of HFC-55-10 was demonstrated by increasing the peak reactor temperature to 269'C. the catalyst provided significant hydrogenation and hydrodechlorination activity at this temperature to convert the intermediate CFC-151-10 to HFC-55-10.
  • the data shown in Figure 4 prove that we have prepared the HFC-55-10 by this technique.
  • the mass fragmentation pattern in Figure 5 can be assigned to this product.
  • This product can also be hydrogenated to HFC-55-10.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Substituts de chlorofluorocarbones utilisés pour la synthèse de produits fluorés de formule RCFbHc+a-1Hf+d-1FeCR' pouvant éventuellement s'effectuer dans un seul ou plusieurs réacteurs sans avoir à isoler aucun des intermédiaires. Le processus consiste à combiner les réactifs RCClaFbHc et R'CCldFeHf en présence d'hydrogène et d'au moins un catalyseur, puis à traiter le produit couplé par de l'hydrogène ou par un agent de fluoration en présence d'un catalyseur facultatif. R et R' sont choisis parmi un groupe d'halogènes, d'hydrocarbures halogénés et d'hydrocarbures, et R ou R' contient du fluor, a et d sont des multiples entiers de 1 à 3; b, c, e, et f sont des multiples entiers de 0 à 2; la somme de a, b et c est égale à 3, et la somme de d, e et f est égale à 3.
EP94925790A 1993-08-16 1994-08-10 Procede de combinaison de molecules chlorees pour la synthese de produits fluores Withdrawn EP0714384A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US107261 1979-12-26
US10726193A 1993-08-16 1993-08-16
PCT/US1994/008986 WO1995005353A1 (fr) 1993-08-16 1994-08-10 Procede de combinaison de molecules chlorees pour la synthese de produits fluores

Publications (1)

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EP0714384A1 true EP0714384A1 (fr) 1996-06-05

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EP94925790A Withdrawn EP0714384A1 (fr) 1993-08-16 1994-08-10 Procede de combinaison de molecules chlorees pour la synthese de produits fluores

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EP (1) EP0714384A1 (fr)
JP (1) JPH09501676A (fr)
AU (1) AU7559194A (fr)
CA (1) CA2167698A1 (fr)
WO (1) WO1995005353A1 (fr)

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JP3304468B2 (ja) * 1993-01-29 2002-07-22 ダイキン工業株式会社 １，１，１，４，４，４−ヘキサフルオロ−２−ブテン類及び１，１，１，４，４，４−ヘキサフルオロブタンの製造方法
FR2740132B1 (fr) 1995-10-23 1997-12-19 Solvay Procede pour la preparation de 1,1,1,3,3-pentafluoropropane
WO1997019751A1 (fr) * 1995-11-29 1997-06-05 E.I. Du Pont De Nemours And Company Catalyseurs de traitement d'hydrocarbures halogenes, leurs precurseurs, leur preparation et leur utilisation
US5919994A (en) * 1995-11-29 1999-07-06 E. I. Du Pont De Nemours And Company Catalytic halogenated hydrocarbon processing and ruthenium catalysts for use therein
WO1998054117A1 (fr) * 1997-05-28 1998-12-03 Alliedsignal Inc. Composes chimiques contenant deux groupes terminaux trifluoromethyle
IT1307755B1 (it) * 1999-02-05 2001-11-19 Ausimont Spa Processo per la dimerizzazione di (cfc-113a).
US7795482B2 (en) 2007-07-03 2010-09-14 E. I. Du Pont De Nemours And Company Method of hydrodechlorination to produce dihydrofluorinated olefins
US8399721B2 (en) 2008-12-22 2013-03-19 E I Du Pont De Nemours And Company Method of hydrodechlorination to produce dihydrofluorinated olefins
US8604257B2 (en) 2010-05-21 2013-12-10 Honeywell International Inc. Process for the preparation of fluorinated cis-alkene
CN111018659A (zh) 2014-02-07 2020-04-17 科慕埃弗西有限公司 用于制备z-1,1,1,4,4,4-六氟-2-丁烯的一体化方法
CN107262092B (zh) * 2017-06-16 2021-03-09 巨化集团技术中心 一种合成顺式1,1,1,4,4,4-六氟-2-丁烯的催化剂及其制备方法和用途
WO2020206322A1 (fr) * 2019-04-05 2020-10-08 The Chemours Company Fc, Llc Procédés de production de z-1,1,1,4,4,4-hexafluorobut-2-ène et intermédiaires pour leur production
CN110590496A (zh) * 2019-09-24 2019-12-20 浙江三美化工股份有限公司 一种气相连续合成顺式-1,1,1,4,4,4-六氟-2-丁烯的方法
JP2023516058A (ja) * 2020-03-04 2023-04-17 ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー （ｚ）－１，１，１，４，４，４－ヘキサフルオロ－２－ブテン及び中間体を生成するためのプロセス
CN112745192A (zh) * 2020-12-31 2021-05-04 山东华夏神舟新材料有限公司 顺式六氟-2-丁烯的连续制备方法

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DE4004494A1 (de) * 1990-02-14 1991-08-22 Bayer Ag Verfahren zur herstellung von gesaettigten, fluorhaltigen und chlorfreien kohlenwasserstoffen
JP3008510B2 (ja) * 1991-02-16 2000-02-14 ダイキン工業株式会社 含フッ素エタンの２量体の製法
DE4215876A1 (de) * 1992-05-14 1993-11-18 Bayer Ag Verfahren zur Herstellung von Hexafluorbutan
EP0571920B1 (fr) * 1992-05-26 1997-01-15 SOLVAY (Société Anonyme) Procédé pour la préparation d'hydrocarbures fluorés

Non-Patent Citations (1)

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Title
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Publication number Publication date
AU7559194A (en) 1995-03-14
CA2167698A1 (fr) 1995-02-23
WO1995005353A1 (fr) 1995-02-23
JPH09501676A (ja) 1997-02-18

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