WO1998008790A1 - Procede de fabrication de difluoromethane - Google Patents
Procede de fabrication de difluoromethane Download PDFInfo
- Publication number
- WO1998008790A1 WO1998008790A1 PCT/JP1997/002963 JP9702963W WO9808790A1 WO 1998008790 A1 WO1998008790 A1 WO 1998008790A1 JP 9702963 W JP9702963 W JP 9702963W WO 9808790 A1 WO9808790 A1 WO 9808790A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- water
- hfc
- mixture
- distillation
- difluoromethane
- Prior art date
Links
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 title claims abstract description 170
- 238000000034 method Methods 0.000 title claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 117
- 239000000203 mixture Substances 0.000 claims abstract description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 238000004821 distillation Methods 0.000 claims description 38
- 239000003054 catalyst Substances 0.000 claims description 6
- 229910052787 antimony Inorganic materials 0.000 claims description 5
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 2
- XWCDCDSDNJVCLO-UHFFFAOYSA-N Chlorofluoromethane Chemical compound FCCl XWCDCDSDNJVCLO-UHFFFAOYSA-N 0.000 abstract description 22
- 238000007670 refining Methods 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 6
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- 230000001172 regenerating effect Effects 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 2
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- -1 for example Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- 238000000998 batch distillation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000005437 stratosphere Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
-
- 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
Definitions
- the present invention relates to a process for producing HFC-32 produced by fluorinating a mixture of difluoromethane (hereinafter also referred to as HFC-32) comprising water, for example, dichloromethane (hereinafter also referred to as HCC-30).
- HFC-32 a mixture of difluoromethane
- HCC-30 dichloromethane
- the present invention relates to a method for producing high-purity HFC-32 by separating water from HFC-32 by distillation from a reaction product comprising 32 and water.
- HF C-32 is a chlorine-free compound that has zero ozone depletion potential, low global warming potential, and excellent refrigeration capacity. It is promising as an alternative refrigerant compound for.
- Examples of the method for producing HFC-32 include a method for fluorinating HCC-30 and a method for reducing dichlorodifluoromethane or Z and chlorodifluoromethane.
- the target compound in order to remove water contained in the raw materials and water accompanying the catalyst, as well as unreacted hydrogen fluoride and by-produced hydrogen chloride with water and an aqueous alkali solution, the target compound is used. Water will be mixed into HFC-32.
- a solid dehydrating agent such as zeolite is often used to remove water from halogenated hydrocarbons.
- Hei 7-33695 discloses that dehydrated zeolite is used for removing water in 1,1-dichloro mouth-111 fluoroethane (hereinafter also referred to as HFC-141b). States that HFC-141b does not degrade.
- a step and an apparatus for regenerating the dehydrating agent are required.
- a target substance adsorbed on the solid dehydrating agent is generated when the dehydrating agent is regenerated.
- HFC-32 since it is mainly used as a refrigerant, high-purity HFC-32 with particularly low water content is required, and therefore, a large amount of solid dehydrating agent must be used.
- ordinary solid dehydrating agents such as zeolite do not have sufficient water removal ability. Since it is decomposed, there is a problem that dehydration is more difficult than in the case of other normal halogenated hydrocarbons.
- a special solid dehydrating agent is required for removing water from HFC-32.
- a method for removing moisture using such a solid dehydrating agent is disclosed in JP-A-6-327968, JP-A-7-305054 and It is proposed in Kaihei 8-173799.
- Such a solid dehydrating agent is used in an HFC-32 when used in a closed system like a refrigerant in an air conditioner compressor (ie, when water does not substantially enter from outside the system).
- high efficiency high moisture adsorption
- water can be continuously supplied from the raw materials etc.
- the HFC-32 adsorbed on the dehydrating agent will eventually be discarded, resulting in higher efficiency. If it is low, the loss of HFC-32 will be large.
- the problem to be solved by the present invention is that the removal of water in HFC-32, which is considered difficult, can be efficiently performed by a simple operation, thereby producing HFC-32 with low moisture content.
- Another object of the present invention is to provide a method for purifying HFC-32 containing water.
- the boiling point of trichlorofluoromethane (hereinafter also referred to as CF C-11) is about 24 ° C under atmospheric pressure, which is far lower than the boiling point of water at 100 ° C.
- the relative volatility of is expected to be significantly less than 1.
- the measurement result is conversely greater than 1; that is, the water concentration in the gas phase is higher than the water concentration in the liquid phase.
- the specific volatility of water is less than 1, HCFC-31 is less than 1, and if the water-HCFC-31 system is an ideal system, the specific volatility of water is about 0.0073 at 25 ° C. It is estimated by calculating according to La Wool's law. This means that separation of water and HCFC-31 by distillation is extremely easy. However, when the relative volatility of water was measured in this system, it was found to be about 0.79, which is about 100 times larger, indicating that it is not easy to separate HCF C-31 from water.
- the present invention provides a mixture comprising water and HFC-32, preferably substantially reduced in water, characterized in that the mixture comprising water and HFC-32 is subjected to a distillation operation.
- a method for producing a mixture comprising water-free HFC-32 is provided.
- the mixture subjected to the distillation operation consists essentially of water and HFC-32, and the mixture after the distillation operation is substantially depleted in water, preferably substantially free of water. Consists essentially of HFC-32.
- FIG. 1 schematically shows a preferred embodiment of the present invention by a flow sheet.
- Reference number 1 is the distillation step
- 2 is the feed to the distillation step
- 3 is the distillate
- 4 is the bottoms
- 5 is the reaction step
- 6 is the recycle stream
- 7 is the reaction step.
- the raw materials are shown.
- substantially reduced water means that the amount of water in the mixture after distillation is smaller than the amount of water in the mixture before distillation (for example, 50% of the original amount, preferably 5%). %), which is generally equivalent to reducing the concentration of water in the mixture.
- the distillation operation of the present invention is an operation of 10-4 Okg / cm 2 -abs., Preferably 15-35 kg / cra 2 -abs., More preferably 20-30 kg / cm 2 -abs.
- the distillation is carried out at a pressure (for example, the operating pressure at the top of the distillation column). They are 5-60 ° C, 20-55 ° C, and 30-50 ° C, respectively.
- the reflux temperature which condenses and returns to the column after distilling is usually preferably the same as the distilling temperature.
- HFC-32 containing water at 200 weight parts per million is distilled at a pressure of 20 kg / cm 2 G, so that HFC-32 containing only water at 10 weight parts per million or less is obtained. Was able to be distilled.
- Example 3 10 weight by distillation at a pressure 20 kg / cm 2 G of a mixture of HFC- 32, H CFC-31 and HCC- 30 including, for example, 400 parts by weight p pm moisture Get HFC-32 with less than P pm moisture I was able to.
- the method of the present invention may be used when HFC-32 (or a mixture thereof with HCFC-31 and / or HCC-30) contains water at or below saturation (typically, the concentration of water is less than about 500 wt. (Preferably not more than 100 weight ppm).
- the method of the present invention is usually applied only to the HFC-32 phase after liquid separation (ie, phase separation). It is preferable to carry out distillation.
- the amount of HCFC-31 and / or HCC-30 is not particularly limited, but usually the mixture is
- the concentration of HFC-32 therein is about 30 to 100% by weight (100% by weight means containing water in the order of hundreds or tens of ppm), preferably about 50 to 100% by weight. More preferably, it is about 70 to 100% by weight.
- the operating pressure of the distillation in the process according to the invention is between 10 and 4 Okg / cm 2 -abs., More preferably 15 to 35 kg / cm 2 -abs., And more preferably 20 to 30 kg / era 2 -abs.
- the temperature is about 5 to 60 ° C, 20 to 55 ° C, and 30 to 50 ° C, which is particularly advantageous in terms of the cost of the pressure-resistant device, utility cost, and the like. Even if these other components are present, HFC-32 with reduced water can be obtained from the top of the distillation step.
- FIG. 1 schematically shows a preferred embodiment of the present invention by a float.
- a mixture 2 containing HFC-32 as a main component containing water is continuously supplied to a distillation column 1.
- high-purity (ie, substantially free of water) HFC-32 was distilled off as distillate 3 from the top of the column, and water and remaining HFC-distilled from the bottom were distilled off from the bottom of the column.
- a mixture containing 32 can be obtained as bottom product 4. If mixture 2 contains HCFC-31 and HCC-30 in addition to HFC-32, these other components can also be removed together as bottoms 4, as indicated by the relative volatility mentioned above. .
- the bottom product 4 is recycled to the reaction step 5 where HFC-32 is generated so that it is processed together with the reaction raw material 7 (dotted line in Fig. 1). 6) can be used efficiently.
- the bottom product 4 substantially consists of HFC-32 and water
- the product may be recycled to a step of removing hydrochloric acid or hydrogen fluoride, for example, to a washing tower or an alkali washing tower.
- the mixture comprising HFC-32 and water contains most or almost no HFC- 32 and the remaining HFC-32 with concentrated water.
- the HFC-32 containing water thus concentrated can be taken out of the system and the water can be discarded.
- HFC-32 It is better to remove water by (eg, adsorption treatment with a solid dehydrating agent) and recover HFC-32.
- HFC-32 containing such water is treated in the system without being taken out of the system.
- an antimony catalyst for example, antimony halide
- the method of the present invention can be carried out using a usual distillation apparatus, and can be carried out continuously or batchwise.
- the process for producing difluoromethane according to the present invention comprises the steps of: distilling a mixture of difluoromethane containing water and a mixture of fluoromethane and / or dichloromethane containing water, whereby water in difluoromethane, which is conventionally difficult to remove, can be easily removed; It becomes possible to obtain difluoromethane.
- Example 1 Example 1
- Example 2 Using the same distillation column as in Example 2, a mixture of HFC-32, HCFC-31 and HCC-30 containing 400 ppm by weight of water was fed to the column 20 columns from the top of the column at about 4 Okg / Hr. Distillation was performed at a reflux ratio of 5 and a pressure of 20 kg / cm 2 G (at an overhead temperature of 30 ° C.), and about 2 Okg / Hr of a part of the reflux liquid was distilled off as a distillate. Table 2 shows the water concentrations of the feed mixture, distillate, and bottoms and the respective component concentrations in this distillation. Table 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69708137T DE69708137T2 (de) | 1996-08-27 | 1997-08-26 | Verfahren zur herstellung von difluormethan |
AU38695/97A AU3869597A (en) | 1996-08-27 | 1997-08-26 | Process for producing difluoromethane |
EP97935887A EP0931784B1 (en) | 1996-08-27 | 1997-08-26 | Process for producing difluoromethane |
BR9711969A BR9711969A (pt) | 1996-08-27 | 1997-08-26 | Processo para prepara-Æo de difluormetano |
CA002264691A CA2264691C (en) | 1996-08-27 | 1997-08-26 | Process for producing difluoromethane |
US09/242,692 US6346172B1 (en) | 1996-08-27 | 1997-08-26 | Process for producing difluoromethane |
JP51146898A JP3605828B2 (ja) | 1996-08-27 | 1997-08-26 | ジフルオロメタンの製造方法 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22484696 | 1996-08-27 | ||
JP8/224846 | 1996-08-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998008790A1 true WO1998008790A1 (fr) | 1998-03-05 |
Family
ID=16820090
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1997/002963 WO1998008790A1 (fr) | 1996-08-27 | 1997-08-26 | Procede de fabrication de difluoromethane |
Country Status (10)
Country | Link |
---|---|
US (1) | US6346172B1 (ja) |
EP (1) | EP0931784B1 (ja) |
JP (1) | JP3605828B2 (ja) |
KR (1) | KR100551521B1 (ja) |
CN (1) | CN1122008C (ja) |
AU (1) | AU3869597A (ja) |
BR (1) | BR9711969A (ja) |
CA (1) | CA2264691C (ja) |
DE (1) | DE69708137T2 (ja) |
WO (1) | WO1998008790A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111072447A (zh) * | 2018-10-19 | 2020-04-28 | 中化蓝天氟材料有限公司 | 一种降低含氟烷烃中酸度和水分的方法 |
WO2021107046A1 (ja) * | 2019-11-28 | 2021-06-03 | ダイキン工業株式会社 | フッ素系炭化水素化合物の脱水方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7189311B2 (en) * | 2001-03-23 | 2007-03-13 | Honeywell International Inc. | Purification of difluoromethane |
JP4952834B2 (ja) * | 2010-09-07 | 2012-06-13 | ダイキン工業株式会社 | 含フッ素化合物からの水分除去方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59231030A (ja) * | 1983-06-11 | 1984-12-25 | Showa Denko Kk | ジフルオロメタンの製造方法 |
JPH08143487A (ja) * | 1994-11-24 | 1996-06-04 | Agency Of Ind Science & Technol | 弗素化アルケン誘導体および弗素化アルカン誘導体の製造方法 |
JPH08183748A (ja) * | 1994-12-28 | 1996-07-16 | Ulsan Chem Co Ltd | ジフルオロメタンの製造方法 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB707145A (en) | 1951-02-26 | 1954-04-14 | Ernest Davies | Dehydrating fluorochloromethanes by distillation |
EP0128510A3 (en) | 1983-06-07 | 1985-05-15 | Showa Denko Kabushiki Kaisha | Process for producing difluoromethane |
JPS59231203A (ja) | 1983-06-10 | 1984-12-25 | Matsushita Electric Ind Co Ltd | 流れ方向制御装置 |
GB9124087D0 (en) * | 1991-11-13 | 1992-01-02 | Ici Plc | Chemical process |
DE69319711T2 (de) * | 1992-04-13 | 1999-01-07 | Daikin Industries, Ltd., Osaka | Verfahren zur entfernung von fluorwasserstoff |
JPH06263658A (ja) * | 1993-03-11 | 1994-09-20 | Showa Denko Kk | ジフルオロメタンの製法 |
JP3213828B2 (ja) | 1993-05-24 | 2001-10-02 | ユニオン昭和株式会社 | HFC−32、HFC−152a用乾燥剤 |
JPH0733695A (ja) | 1993-07-23 | 1995-02-03 | Central Glass Co Ltd | 1,1−ジクロロ−1−フルオロエタンの水分除去方法 |
JP3688333B2 (ja) | 1994-03-15 | 2005-08-24 | 東芝キヤリア株式会社 | 冷凍サイクル用組成物および冷凍装置 |
JPH08173799A (ja) | 1994-10-28 | 1996-07-09 | Tosoh Corp | 乾燥剤、その製造方法及びその用途 |
US5785822A (en) * | 1996-05-23 | 1998-07-28 | Alliedsignal Inc. | Process for separating difluoromethane |
US5800682A (en) * | 1996-10-08 | 1998-09-01 | Alliedsignal Inc. | Process for the production of difluoromethane |
-
1997
- 1997-08-26 CN CN97198965A patent/CN1122008C/zh not_active Expired - Lifetime
- 1997-08-26 KR KR1019997001482A patent/KR100551521B1/ko not_active IP Right Cessation
- 1997-08-26 AU AU38695/97A patent/AU3869597A/en not_active Abandoned
- 1997-08-26 DE DE69708137T patent/DE69708137T2/de not_active Expired - Fee Related
- 1997-08-26 JP JP51146898A patent/JP3605828B2/ja not_active Expired - Fee Related
- 1997-08-26 WO PCT/JP1997/002963 patent/WO1998008790A1/ja active IP Right Grant
- 1997-08-26 CA CA002264691A patent/CA2264691C/en not_active Expired - Fee Related
- 1997-08-26 EP EP97935887A patent/EP0931784B1/en not_active Expired - Lifetime
- 1997-08-26 BR BR9711969A patent/BR9711969A/pt not_active Application Discontinuation
- 1997-08-26 US US09/242,692 patent/US6346172B1/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59231030A (ja) * | 1983-06-11 | 1984-12-25 | Showa Denko Kk | ジフルオロメタンの製造方法 |
JPH08143487A (ja) * | 1994-11-24 | 1996-06-04 | Agency Of Ind Science & Technol | 弗素化アルケン誘導体および弗素化アルカン誘導体の製造方法 |
JPH08183748A (ja) * | 1994-12-28 | 1996-07-16 | Ulsan Chem Co Ltd | ジフルオロメタンの製造方法 |
Non-Patent Citations (1)
Title |
---|
See also references of EP0931784A4 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111072447A (zh) * | 2018-10-19 | 2020-04-28 | 中化蓝天氟材料有限公司 | 一种降低含氟烷烃中酸度和水分的方法 |
WO2021107046A1 (ja) * | 2019-11-28 | 2021-06-03 | ダイキン工業株式会社 | フッ素系炭化水素化合物の脱水方法 |
JP2021091668A (ja) * | 2019-11-28 | 2021-06-17 | ダイキン工業株式会社 | フッ素系炭化水素化合物の脱水方法 |
Also Published As
Publication number | Publication date |
---|---|
CA2264691C (en) | 2006-10-17 |
AU3869597A (en) | 1998-03-19 |
KR20000035824A (ko) | 2000-06-26 |
DE69708137D1 (de) | 2001-12-13 |
DE69708137T2 (de) | 2002-06-20 |
EP0931784A1 (en) | 1999-07-28 |
KR100551521B1 (ko) | 2006-02-13 |
JP3605828B2 (ja) | 2004-12-22 |
CA2264691A1 (en) | 1998-03-05 |
EP0931784A4 (ja) | 1999-07-28 |
US6346172B1 (en) | 2002-02-12 |
EP0931784B1 (en) | 2001-11-07 |
BR9711969A (pt) | 1999-08-24 |
CN1122008C (zh) | 2003-09-24 |
CN1234015A (zh) | 1999-11-03 |
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