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WO1998019981A1 - Fabrication d'hexafluoroethane - Google Patents

Fabrication d'hexafluoroethane Download PDF

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Publication number
WO1998019981A1
WO1998019981A1 PCT/US1997/019737 US9719737W WO9819981A1 WO 1998019981 A1 WO1998019981 A1 WO 1998019981A1 US 9719737 W US9719737 W US 9719737W WO 9819981 A1 WO9819981 A1 WO 9819981A1
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WIPO (PCT)
Prior art keywords
cfc
chlorine
pfc
catalyst
productivity
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Ceased
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PCT/US1997/019737
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English (en)
Inventor
Barry Asher Mahler
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EIDP Inc
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EI Du Pont de Nemours and Co
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Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to EP97913902A priority Critical patent/EP0935592A1/fr
Priority to JP52156898A priority patent/JP2001507674A/ja
Publication of WO1998019981A1 publication Critical patent/WO1998019981A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
    • C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms

Definitions

  • the present invention relates to a process for slowing the deactivation rate and/or eliminating deactivation of chrome oxide catalyst used in the vapor phase production of hexafluoroethane by fluorination wherein the fluorination is carried out in the presence of chlorine.
  • the present invention further relates to processes for reducing and/or eliminating the presence of undesired by-products in such fluorinations by contacting the catalyst with chlorine.
  • Highly fluorinated fluorocarbons are utilized as plasma etchant gases in the semiconductor industry.
  • the highly fluorinated fiuorocarbon hexafluoroethane (CF 3 CF 3 , or PFC- 116) has found utility as a chemical vapor deposition (CND) chamber cleaning gas and as a plasma etchant gas in semiconductor device fabrication.
  • CND chemical vapor deposition
  • Etchant gases of very high purity are critical in this application.
  • PFC-116 has been known to be produced by allowing perhalogenated chlorofluoroethanes, e.g., trichlorotrifluoroethanes (CC1 3 CF 3 [CFC-113a] or CC1 2 FCC1F 2 [CFC-1 13]), dichlorotetrafluoroethanes (CC1 2 FCF 3 [CFC-1 14a] or CC1F 2 CC1F 2 [CFC-1 14]), and chloropentafluoroethane (CC1F 2 CF 3 [CFC-115]), among others, to react with hydrogen fluoride (HF) in a vapor phase over a solid chrome oxide catalyst.
  • trichlorotrifluoroethanes CC1 3 CF 3 [CFC-113a] or CC1 2 FCC1F 2 [CFC-1 13]
  • dichlorotetrafluoroethanes CC1 2 FCF 3 [CFC-1 14a] or CC1F
  • Such conventional processes for manufacture of PFC-1 16 result in progressive deactivation of the catalyst.
  • catalyst deactivation results in a decrease in the instantaneous productivity of PFC-116, and necessitates alteration of the reaction operating conditions to off-set the impact of the catalyst deactivation and maintain process productivity and product purity.
  • the reaction temperature may have to be incrementally increased to maintain the instantaneous PFC- 116 productivity as the catalyst deactivates.
  • conventional methods for manufacturing PFC-1 16 often produce a product stream containing significant amounts of fiuorocarbon byproducts which are difficult to separate from PFC- 1 16 by conventional separation techniques. Altering reactor conditions, such as increasing the reaction temperature to offset the catalyst deactivation, often produces concomitant increases in production of such fiuorocarbon by-products.
  • the present inventors have discovered that the addition of chlorine to a reactant feed stream significantly retards and can essentially eliminate the deactivation of chrome oxide catalyst used in manufacture of PFC-116.
  • the present inventors have further discovered that by adding chlorine to such feed streams it is possible to inhibit formation of undesirable fiuorocarbon by-products.
  • the present invention solves problems associated with conventional vapor phase fluorination processes for production of PFC-116 by providing processes for mitigating chrome oxide catalyst deactivation that accompanies such processes. Further, the present invention solves problems associated with conventional vapor phase fluorination processes for production of PFC-1 16 by providing processes for reducing the concentration of undesirable fiuorocarbon by-products in the off- gas (product) stream of such fluorination processes.
  • the present invention comprises a process for the production of PFC- 1 16, comprising: contacting HF, a chlorofluorocarbon precursor selected from the group consisting of CFC-113, CFC-113a, CFC-1 14, CFC-1 14a, and CFC-115, and an effective amount of chlorine in a vapor phase in the presence of a fluorination catalyst comprising Cr O 3 at a temperature of from about 300°C to 500°C to form a product stream, and recovering PFC- 1 16 from the product stream.
  • Figure 1 is a plot of the reaction temperature required to maintain chrome oxide catalyst productivity over time with and without chlorine co-feed.
  • Figure 2 is a plot of fiuorocarbon by-product concentrations over time with and without chlorine co-feed.
  • Figure 3 is a plot of the reaction temperature required to maintain chrome oxide catalyst productivity over time with and without chlorine co-feed.
  • Figure 4 is a plot of fiuorocarbon by-product concentrations over time with and without chlorine co-feed.
  • the highly fluorinated fiuorocarbon hexafluoroethane (CF 3 CF 3 , PFC-116) is conventionally produced by allowing hydrogen fluoride (HF) to react with perhalogenated chlorofluorocarbon precursors such as CFC-113, CFC-1 14 and CFC-115 in a vapor phase over a solid chrome oxide (Cr 2 O ) catalyst.
  • HF hydrogen fluoride
  • perhalogenated chlorofluorocarbon precursors such as CFC-113, CFC-1 14 and CFC-115
  • Cr 2 O solid chrome oxide
  • Examples of such processes are described in "Catalytic Fluorination of 1,2-Dichlorotetrafluoroethane (FC-114) and of 1,1-Dichlorotetrafluoroethane (FC-114a) with HF" by Marangoni et al. in La Chimica E L Industria, Vol. 67, No.
  • CFC-113 1,1-dichloro- 1,2,2,2 tetrafluoroethane (CFC-114a) and 1,2-dichloro- 1,1,2,2 tetrafluoroethane (CFC-114) produces a reactor off-gas (reaction product mixture) comprising chloropentafmoroethane (CFC-1 15) and hexafluoroethane (PFC- 116) and hydrogen chloride (HC1).
  • the CFC- 115 formed and any CFC- 1 13, CFC-1 13a, CFC-1 14, and/or CFC-114a in the off-gas may be separated from the off-gas and recycled for further conversion to PFC-1 16.
  • PFC-1 16 may then be recovered as product by any suitable process.
  • PFC- 1 16 may be recovered from the reactor product stream, for example, by the process disclosed in World Intellectual Property Organization Publication No. WO96/09271 , the disclosure of which is hereby incorporated by reference.
  • Catalyst comprising chromium oxide is desirable in conventional conversion of the perhalogenated chlorofluorocarbon precursors CFC-1 13, CFC- 1 13a, CFC-114, CFC-114a, and CFC-115 to the highly fluorinated fiuorocarbon PFC-1 16.
  • Such catalysts have a higher activity for PFC-1 16 synthesis than non- chromium oxide catalysts, e.g., aluminum oxide (Al O 3 ) catalysts.
  • a chromium oxide catalyst produces higher concentrations of PFC-1 16 in the reactor off-gas at a given operating temperature compared to a non-chromium oxide catalyst such as an aluminum oxide catalyst.
  • a chromium oxide catalyst can produce the same concentration of PFC-116 in the reactor off-gas but can do so while operating at a lower temperature compared to a non-chromium oxide catalyst such as an aluminum oxide catalyst.
  • Chromium oxide catalysts can further typically produce PFC-116 concentrations of greater than 10 mole % of the total organics exiting in the reactor off-gas, whereas obtaining such high PFC-1 16 concentrations with non-chromium oxide catalysts such as aluminum oxide is difficult, if not impossible.
  • Chromium oxide catalysts suitable for these conventional conversions comprise Cr 2 O formed by any process known in the art. Particularly preferred in the present process is Cr 2 O catalyst prepared such that its alkali metal content is less than 100 ppmw (parts-per-million by weight). Most preferred in the present process is Cr O 3 catalyst prepared as that disclosed in U.S. Patent No. 5,334,787, incorporated herein by reference.
  • PFC-1 16 concentrations can be maintained in the reaction off-gas by increasing the contact time of the chlorofluorocarbon precursors with the catalyst (i.e., by reducing the reactor throughput), or by adjusting the HF/precursor feed ratio.
  • the organic molar feed rate to the reactor is unchanged that the PFC- 116 off-gas concentration as mole % of the organics in the product stream is directly proportional to PFC-116 productivity.
  • PFC- 1 16 productivity is defined as the weight of PFC- 1 16 produced per time period
  • PFC- 1 16 productivity is defined as the weight of PFC- 1 16 produced per time period
  • PFC- 1 16 productivity is defined as the weight of PFC- 1 16 produced per time period
  • the precursor feed stream feed-in temperatures and/or the operating temperature of the reactor itself are increased to offset the effect of catalyst deactivation.
  • increases in temperature typically accelerate the deactivation rate of the catalyst such that loss of catalyst activity occurs faster at higher temperatures than at a lower temperature, i.e., the time required for a given percentage drop in instantaneous PFC-116 productivity becomes less.
  • more frequent and larger increases in temperature become necessary over time to maintain the instantaneous PFC- 1 16 productivity.
  • non-1 lx fiuorocarbon by-products any compounds other than PFC-116 ("1 lx" wherein x is 6) or the chlorofluorocarbon precursors CFC-1 13 and CFC-113a ("1 lx" wherein x is 3), CFC-114 and CFC-114a ("1 lx” wherein x is 4), and CFC-115 ("1 lx” wherein x is 5).
  • Non-1 lx fiuorocarbon by-product formation results in overall loss of PFC-116 yield from the chlorofluorocarbon precursors.
  • the non-1 lx fiuorocarbon by-products that can be produced include fiuorocarbon 2x byproducts such as HCFC-22 ("2x" wherein x is 2) [chlorodifluoromethane] or HFC-23 ("2x" wherein x is 3) [trifluoromethane] and/or fiuorocarbon 12x byproducts such as HCFC-123 ("12x” wherein x is 3) [l,l-dichloro-2,2,2- trifluoroethane], HCFC-124 ("12x” wherein x is 4) [1-chloro- 1,2,2,2- tetrafluoroethane] or HFC- 125 (“12x” wherein x is 5) [pentafluoroethane] and
  • the present invention is a process for the production of PFC-1 16, comprising: contacting HF, a chlorofluorocarbon precursor selected from the group consisting of CFC-113, CFC-113a, CFC-1 14, CFC-1 14a, and CFC-1 15, and an effective amount of chlorine in a vapor phase in the presence of a fluorination catalyst comprising Cr 2 O 3 at a temperature of from about 300°C to 500°C to form a product stream, and recovering PFC-116 from the product stream.
  • the present inventors have discovered that carrying out, in the presence of an effective amount of chlorine, conventional processes wherein the chlorofluorocarbon precursors CFC-113, CFC-113a, CFC-1 14, CFC-114a, and CFC-1 15 are contacted with HF in the presence of a fluorination catalyst comprising Cr 2 O 3 resulting in a PFC- 116 product stream, slows, if not eliminates, the progressive catalyst deactivation observed in the conventional processes.
  • an "effective amount" of chlorine is meant an amount of chlorine present during said contacting step which extends the chrome oxide catalyst life. The amount of chlorine can be relatively low and still effectively produce the unexpected effect of catalyst life extension.
  • Chlorine concentration as low as 0.5 weight% (wt%) of the combined weight of HF and chlorine present during said contacting step extends the chrome oxide catalyst life compared to conventional processes employing no chlorine.
  • Higher chlorine concentrations present during said contacting step from about 2.5 wt% to 5 wt% of the combined weight of HF and chlorine, further extends the chrome oxide catalyst life and effectively stops deactivation of the catalyst.
  • the beneficial effect of chlorine present during said contacting step appears to endure for a period after chlorine addition is stopped, such that the higher catalyst deactivation rate does not resume immediately upon cessation of the chlorine feed.
  • extentends chrome oxide catalyst life is meant that decreases over time in instantaneous productivity of PFC-116 from the catalyst at a given set of conditions are eliminated or reduced when chlorine is present during said contacting step versus when chlorine is absent from said contacting step.
  • extends chrome oxide catalyst life is also meant that the instantaneous productivity of PFC- 116 is higher when chlorine is present during said contacting step versus when chlorine is absent from said contacting step.
  • instantaneous productivity is meant the weight of PFC-116 produced per weight of catalyst over a given time period.
  • the instantaneous PFC- 1 16 productivity of a continuous conventional process will begin to sharply decrease, with the instantaneous productivity after 2 weeks typically having decreased by more than 10% compared to the instantaneous productivity obtained from the same reactor at the same reactor conditions over the first two or three days of that 2 week period of operation.
  • the instantaneous productivity of a process wherein said contacting step is carried out in the presence of chlorine will decrease by less than 10 %, typically less than 5 %, most often less than 2 % compared to the instantaneous productivity obtained from the same reactor at the same reactor conditions over the first two or three days of that 2 week period of operation.
  • total temperature increases of less than 5°C are typically required over the 2 week period to maintain the PFC-1 16 productivity that had been obtained from the reactor over the first two or three days of that 2 week period of operation wherever said contacting step is carried out in the presence of an effective amount of chlorine, whereas total temperature increases of greater than 5°C are typically required over the 2 week period to maintain the productivity wherever said contacting step is carried out in the absence of an effective amount of chlorine.
  • PFC-116 concentrations of at least 2.5 mole%, more typically at least 5.0 mole%, most typically at least 10 mole% of the organics in the product stream may be obtained simultaneously with said extended catalyst life.
  • Carrying out conventional PFC- 1 16 production by chrome oxide based fluorination of chlorofluorocarbon precursors in the presence of chlorine mitigates and/or avoids the need to increase the reaction temperature to maintain instantaneous PFC- 116 productivity and can delay the need to change out or regenerate the chrome oxide catalyst.
  • the present inventors have further discovered that carrying out, in the presence of an effective amount of chlorine, conventional processes wherein chlorofluorocarbon precursors CFC-113, CFC-1 13a, CFC-114, CFC-114a, and CFC-115 are contacted with HF in the presence of a fluorination catalyst comprising Cr 2 O resulting in a PFC-1 16 product stream, results in reduced concentration of potentially undesired fiuorocarbon by-products in the reaction off-gas.
  • the present invention therefore comprises employing chlorine to maintain or increase the instantaneous productivity of PFC-1 16 in chrome oxide- based fluorination of the chlorofluorocarbon precursors CFC-113, CFC-113a, CFC-114, CFC-114a, and CFC-115, wherein chlorine addition allows higher reaction temperature operation and thus higher reaction rates for formation of PFC-116 but without the deficiency of concomitant accelerated catalyst deactivation and increased fiuorocarbon by-product generation that is seen in conventional process in which chlorine is absent.
  • contacting step is carried out at from about 250°C to 500°C, more preferably from about 300°C to 500°C.
  • the contacting step may be carried out at sub- or super-atmospheric pressures; pressures of from about 0 to 150 psig are preferred.
  • the contacting step can be carried out over a wide range of HF/organic molar feed ratios, but HF/organic molar feed ratios of between from about 0.5/1 to 6/1 are preferred.
  • the reactor be operated over a range of throughputs (organic feed rate per weight of catalyst per unit time), but throughputs of between from about 0.1 to 2.0 pph organic feed per pound of catalyst are preferred.
  • Recovering the PFC- 1 16 from the product stream may occur by any suitable process.
  • PFC-116 may be recovered from the reactor product stream by the distillation process disclosed in World Intellectual Property Organization Publication No. WO96/09271, the disclosure of which is hereby incorporated by reference.
  • any suitable halogen can be employed for maintaining or improving the instantaneous productivity of PFC-1 16. That is, at least one halogen such as chlorine (Cl 2 ), fluorine (F 2 ), and bromine (Br 2 ) can be employed in the contacting step of the present invention in any suitable manner, e.g., in situ generation of an elemental halogen, and injection into the feed stream, reactor or recycle stream.
  • halogen such as chlorine (Cl 2 ), fluorine (F 2 ), and bromine (Br 2 )
  • Example 1 In this Example, a fresh batch of the catalyst produced by the procedure of U.S. Patent No. 5,334,787 was charged to the U-tube reactor and activated by the procedure of U.S. Patent No. 5,334,787.
  • a feed stream consisting of a CFC-114/CFC-l 15/HFC-125 mixture (69 wt% CFC-115, 29 wt% CFC-114, 2 wt% HFC- 125) was then fed to the reactor at a total organic feed rate of 0.3 kph (0.7 pph ).
  • Hydrogen Fluoride (HF) was fed to the reactor at 0.082 kph (0.18 pph).
  • the length of time the catalyst could produce the desired PFC-1 16 concentration at any given temperature also continued to decrease as the operating temperature required to produce that concentration increased, i.e., the catalyst could only run for increasingly shorter periods before additional temperature increases were necessary to offset the deactivation.
  • the reaction temperature had to be increased from the initial 400°C to over 440°C in order to maintain the target 15-18 organic mole % PFC-1 16 in the off-gas
  • a concomitant advantage of the chlorine addition was the reduction of the no ⁇ -1 lx fiuorocarbon off-gas by-products.
  • the lower 2.5 wt% chlorine feed condition although deactivation of the catalyst was successfully mitigated, there was little change in the total 2x + 12x + 13x fiuorocarbon by-product concentration in the off-gas.
  • the higher 5.0 wt% chlorine feed rate however, the total concentration of the non-1 lx fiuorocarbon off-gas by-products was seen to decrease, as indicated by the reduction in the total 2x + 12x + 13x fiuorocarbon by-product concentration in the off-gas from the initial 2.5 organic mole% prior to chlorine addition down to 1.5 mole %.
  • Example 2 In this Example, a fresh batch of the catalyst produced by the procedure of U.S. Patent No. 5,334,787 was charged to the U-tube reactor and activated by the procedure of U.S. Patent No. 5,334,787. A feed stream consisting of a CFC-114/CFC-l 15 mixture (70 wt% CFC-115, 30 wt% CFC-114) was then fed to the reactor at a total organic feed rate of 0.3 kph (0.7 pph). Hydrogen Fluoride (HF) was fed to the reactor at 8.2 x 10 "2 kph (0.18 pph). The reactor operating pressure was 791 kPa (100 psig), and the reactor was initially operated at 375°C. The reactor operating temperature was then increased to bring the
  • Example 3 As may be seen in Figure 3, and in contrast to the catalyst activity over time in Example 1 before chlorine was added to the feed in Example 1 , the need for periodic increases in the temperature was markedly reduced with chlorine feed in Example 2, such that the temperature in Example 2 had to be increased by only 15°C to maintain the PFC-116 produced over the same 1,100 hours during which a 40°C increase had been required in Example 1. Based on this data, it was calculated that the half-life of the catalyst increased from 470 hours without any Chlorine feed to 1,400 hours with the addition of the chlorine at 0.5 wt% of the HF feedrate.
  • Catalyst half-life is defined as the period of time required for a catalyst to deactivate to the extent that a reactor having twice the reactor volume filled with catalyst would be necessary to obtain the same instantaneous PFC-1 16 productivity that a single reactor volume had previously produced at a given starting point and under the same process operating conditions.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Cette invention se rapporte à un procédé de production d'un fluorocarbone hautement fluoré comportant du PFC-116. Ledit procédé consiste à mettre en contact du fluorure d'hydrogène (HF), une quantité efficace de chlore, et un précurseur de chlorofluorocarbone sélectionné dans le groupe constitué par les hydrocarbures chlorofluorés CFC-113, CFC-113a, CFC-114, CFC-114a et CFC-115, en phase vapeur, en présence d'un catalyseur de fluoration contenant du Cr2O3 et à une température comprise approximativement entre 300 °C et 500 °C, en vue de la formation d'un flux résultant, puis à récupérer le fluorocarbone hautement fluoré du flux résultant. La quantité de chlore est suffisante pour maintenir ou accroître la productivité instantanée de PFC-116.
PCT/US1997/019737 1996-11-01 1997-10-30 Fabrication d'hexafluoroethane Ceased WO1998019981A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP97913902A EP0935592A1 (fr) 1996-11-01 1997-10-30 Fabrication d'hexafluoroethane
JP52156898A JP2001507674A (ja) 1996-11-01 1997-10-30 ヘキサフルオロエタンの製造

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US3015096P 1996-11-01 1996-11-01
US60/030,150 1996-11-01
US3865997P 1997-02-21 1997-02-21
US60/038,659 1997-02-21
US95989897A 1997-10-29 1997-10-29
US08/959,898 1997-10-29

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WO1998019981A1 true WO1998019981A1 (fr) 1998-05-14

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WO (1) WO1998019981A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104918700A (zh) * 2013-01-29 2015-09-16 阿科玛股份有限公司 氟化催化剂的活化和再生
CN109020777A (zh) * 2017-06-09 2018-12-18 浙江蓝天环保高科技股份有限公司 一种六氟乙烷的生产工艺

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102003550B1 (ko) * 2011-09-30 2019-07-25 허니웰 인터내셔날 인코포레이티드 2,3,3,3-테트라플루오로프로펜의 제조 방법
WO2013067356A1 (fr) * 2011-11-04 2013-05-10 Haiyou Wang Procédé de fabrication du 2,3,3,3-tétrafluoropropène
JP7029093B2 (ja) * 2020-09-01 2022-03-03 セントラル硝子株式会社 トランス－１－クロロ－３，３，３－トリフルオロプロペンの製造方法

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USH1129H (en) * 1989-02-24 1993-01-05 E. I. Du Pont De Nemours And Company Process for manufacture of 1,1,1,2-tetrafluoroethane
WO1993017988A1 (fr) * 1992-03-10 1993-09-16 E.I. Du Pont De Nemours And Company Purification de produits a base d'hexafluoroethane

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JPS49134612A (fr) * 1973-05-08 1974-12-25
USH1129H (en) * 1989-02-24 1993-01-05 E. I. Du Pont De Nemours And Company Process for manufacture of 1,1,1,2-tetrafluoroethane
EP0403108A1 (fr) * 1989-06-13 1990-12-19 E.I. Du Pont De Nemours And Company Composition de catalyseur à base de CR2O3
WO1993017988A1 (fr) * 1992-03-10 1993-09-16 E.I. Du Pont De Nemours And Company Purification de produits a base d'hexafluoroethane

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104918700A (zh) * 2013-01-29 2015-09-16 阿科玛股份有限公司 氟化催化剂的活化和再生
CN109020777A (zh) * 2017-06-09 2018-12-18 浙江蓝天环保高科技股份有限公司 一种六氟乙烷的生产工艺
CN109020777B (zh) * 2017-06-09 2021-06-15 浙江蓝天环保高科技股份有限公司 一种六氟乙烷的生产工艺

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JP2001507674A (ja) 2001-06-12
KR20000052947A (ko) 2000-08-25
EP0935592A1 (fr) 1999-08-18

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