WO2015093527A1 - フッ素化炭化水素化合物の精製方法 - Google Patents
フッ素化炭化水素化合物の精製方法 Download PDFInfo
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- WO2015093527A1 WO2015093527A1 PCT/JP2014/083406 JP2014083406W WO2015093527A1 WO 2015093527 A1 WO2015093527 A1 WO 2015093527A1 JP 2014083406 W JP2014083406 W JP 2014083406W WO 2015093527 A1 WO2015093527 A1 WO 2015093527A1
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- fluorinated hydrocarbon
- hydrocarbon compound
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- 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
- C07C17/389—Separation; Purification; Stabilisation; Use of additives by adsorption on solids
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- 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 method for purifying a fluorinated hydrocarbon compound. More specifically, the crude product of the fluorinated hydrocarbon compound is brought into contact with a specific molecular sieve (hereinafter, also referred to as “MS”), which is a kind of hydrated metal salt of synthetic crystal aluminosilicate, with simple equipment.
- MS specific molecular sieve
- the present invention relates to a method for purifying a fluorinated hydrocarbon compound that can suppress the generation of a deHF compound caused by a decomposition reaction and can efficiently remove moisture.
- a fluorinated hydrocarbon compound has been used as a dry etching gas for semiconductor production because it has excellent etching selectivity with respect to a material to be etched.
- a fluorinated carbon compound used in the semiconductor manufacturing field or the like is required to be purified to a high purity with an organic component purity of 99.90% or more and a water concentration of 50 ppm or less in order to realize high etching selectivity.
- a method for dehydrating such a fluorinated hydrocarbon compound a method using MS which is a general dehydrating agent is known.
- MS which is a general dehydrating agent
- Patent Document 1 proposes a method for purifying hexafluoro-1,3-butadiene (formula; C 4 F 6 ) using MS having an average pore diameter of 5 mm. According to this method, it is said that hexafluoro-1,3-butadiene having at least 99.9% and a water content of 100 ppm or less can be obtained by contacting the compound with MS in a flow-through manner.
- this document only describes the case where an unsaturated fluorinated carbon compound having 4 carbon atoms is used.
- Patent Document 2 proposes a method for purifying fluorinated hydrocarbons, characterized by reducing hydrogen fluoride by bringing a fluorinated hydrocarbon compound having 4 to 8 carbon atoms into contact with MS or alumina. ing.
- this document includes 1,1,1,2,4,4,4-heptafluoro-n-butane, 1,1,1,2,2,3 as specific examples of the fluorinated hydrocarbon compound. , 5,5,5-nonafluoro-n-pentane.
- Patent Document 3 proposes a method of dehydrating the compound by suppressing the decomposition reaction of the organic liquid using MS3A in which the amount of acid sites is reduced to a predetermined amount or less by pretreatment.
- an alcohol compound is used in the examples.
- JP 2003-261480 A (US 6,544,319 B1) JP 2002-47218 A Japanese translation of PCT publication No. 2002-531538 (WO00 / 34217 pamphlet)
- An object of the present invention is to provide a method for purifying a fluorinated hydrocarbon compound.
- the present inventor has decomposed the fluorinated hydrocarbon compound using MS having a carbon dioxide adsorption amount of a predetermined amount or less and an average pore diameter of a predetermined diameter.
- MS having a carbon dioxide adsorption amount of a predetermined amount or less and an average pore diameter of a predetermined diameter.
- the inventors have found that the production of a deHF compound caused by the reaction is suppressed and water can be efficiently removed, and the present invention has been completed.
- the chain saturated fluorinated hydrocarbon compound represented by the formula: C 4 H 9 F or C 5 H 11 F, the carbon dioxide adsorption amount is 50 ⁇ mol / g or less, and Provided is a method for purifying a chain saturated fluorinated hydrocarbon compound, characterized by removing water contained in the crude product by contacting with a hydrous metal salt of a synthetic crystal aluminosilicate having an average pore size of 3 mm Is done.
- the chain saturated fluorinated hydrocarbon compound is preferably a chain saturated fluorinated hydrocarbon compound having no fluorine atom bonded to a terminal carbon atom, such as 2-fluorobutane, A compound selected from the group consisting of 2-methyl-2-fluoropropane and 2-fluoropentane is more preferable, and 2-fluorobutane is particularly preferable.
- the purification method of the present invention includes a crude product of a chain saturated fluorinated hydrocarbon compound represented by the formula: C 4 H 9 F or C 5 H 11 F, a carbon dioxide adsorption amount of 50 ⁇ mol / g or less, and Moisture contained in the crude product is removed by contacting with a hydrous metal salt of synthetic crystal aluminosilicate having an average pore diameter of 3 mm. According to the purification method of the present invention, generation of a deHF compound caused by a decomposition reaction is suppressed, and moisture can be efficiently removed.
- the purity of the fluorinated hydrocarbon compound to be purified and the content of the deHF compound are values calculated from the peak area by gas chromatography using a flame ionization detector (FID) as a detector. It is.
- the water content in the fluorinated hydrocarbon compound is a value measured using FT-IR.
- the fluorinated hydrocarbon compound to be purified is a chain saturated fluorinated hydrocarbon compound represented by the formula: C 4 H 9 F or C 5 H 11 F.
- C 4 H 9 F or C 5 H 11 F include 1-fluorobutane, 2-fluorobutane, 1-fluoro-2-methylpropane, 2-fluoro-2-methylpropane, 1-fluoropentane, 2 -Fluoropentane, 3-fluoropentane, 1-fluoro-2-methylbutane, 1-fluoro-3-methylbutane, 2-fluoro-2-methylbutane, 2-fluoro-3-methylbutane, 1-fluoro-2,2-dimethyl Propane is mentioned.
- a chain saturated fluorination selected from the group consisting of 2-fluorobutane, 2-fluoro-2-methylpropane, and 2-fluoropentane from the viewpoint of obtaining a more remarkable effect of the present invention.
- a hydrocarbon compound is more preferable, and 2-fluorobutane is particularly preferable.
- fluorinated hydrocarbon compounds are known compounds.
- the “crude product of a fluorinated hydrocarbon compound” refers to an object to be purified by contact with a hydrous metal salt of a synthetic crystal aluminosilicate.
- a crude product of the fluorinated hydrocarbon compound a crude product as described below is usually used, but it was purified according to a separate purification method before purification by contact with a hydrous metal salt of a synthetic crystal aluminosilicate. It may be a thing. Further, the purification method of the present invention may be repeated.
- the crude product of the fluorinated hydrocarbon compound used in the present invention contains a deHF compound, moisture, and the like. Contains a trace amount.
- the content of the deHF compound contained in the crude product is usually 0.01% to 0.1%, preferably 0.02% to 0.05% on a volume basis.
- the amount of water contained in the crude product (that is, the amount of water contained in the crude product of the fluorinated hydrocarbon compound before contacting with the hydrous metal salt of the synthetic crystal aluminosilicate is usually 100 ppm to 5000 ppm, preferably 100 ppm to 3000 ppm.
- the crude product of the fluorinated hydrocarbon compound used in the present invention can be produced and obtained by a known production method.
- a crude product of 2-fluorobutane is disclosed in J. Org. Org. Chem, 44 (22), 3872 (1987), and can be obtained and obtained.
- what is marketed can also be used as a crude product of a fluorinated hydrocarbon compound.
- the hydrous metal salt (MS) of the synthetic crystalline aluminosilicate used in the present invention is a molecular sieve (MS3A) having an average pore diameter of 3 mm.
- MS is known as a solid acid.
- the amount of carbon dioxide adsorbed is 50 ⁇ mol / g or less because the generation of deHF compounds caused by decomposition reactions and the like can be suppressed and moisture can be removed efficiently even when brought into contact with a fluorinated hydrocarbon compound.
- the measuring method of a carbon dioxide adsorption amount is a method of the Example description mentioned later.
- the hydrated metal salt of synthetic crystal aluminosilicate having a carbon dioxide adsorption amount of 50 ⁇ mol / g or less and an average pore diameter of 3 mm is a known substance and can be produced and obtained by a known method. Moreover, what is marketed as a hydrous metal salt of the synthetic crystal aluminosilicate whose carbon dioxide adsorption amount is 50 ⁇ mol / g or less and whose average pore diameter is 3 mm can be used as it is.
- the hydrous metal salt of synthetic crystal aluminosilicate is commercially available in various shapes such as pellets, trisives, beads, and powders. Among these, from the viewpoint of excellent dehydration effect and handling, pellets are preferable, pellets having a diameter of 1 to 4 mm are more preferable, and pellets having a diameter of 1.5 to 3.5 mm are further preferable. preferable.
- the hydrated metal salt of synthetic crystal aluminosilicate may be subjected to an activation treatment as necessary before use.
- the amount of the hydrous metal salt of the synthetic crystalline aluminosilicate is preferably 5 to 80 parts by weight, more preferably 10 to 50 parts by weight with respect to 100 parts by weight of the fluorinated hydrocarbon compound. If the amount of the hydrous metal salt in the synthetic crystal aluminosilicate is too small, the dehydration ability tends to decrease, and conversely, even if the amount of the hydrous metal salt in the synthetic crystal aluminosilicate is excessively increased, the effect is not particularly improved. There is no productivity.
- Examples of the method of bringing a crude product of a fluorinated hydrocarbon compound into contact with a hydrated metal salt of a synthetic crystal aluminosilicate include, for example, (1) fluorinated carbonization to be purified in a container containing a hydrated metal salt of a synthetic crystal aluminosilicate Immersion method in which a crude product of hydrogen compound is charged and allowed to stand, (2) A distribution method in which a crude product of a fluorinated hydrocarbon compound is circulated through a tube filled with a hydrous metal salt of a synthetic crystal aluminosilicate, and both are brought into contact with each other Etc. Either a dipping method or a distribution method may be used and can be selected as appropriate.
- the temperature at which the crude product of the fluorinated hydrocarbon compound is brought into contact with the hydrous metal salt of the synthetic crystal aluminosilicate varies depending on the boiling point of the fluorinated hydrocarbon compound to be used. Since there exists a possibility of causing a fall, it is preferable to make it contact at temperature lower than a boiling point.
- the contact temperature is preferably in the range of 0 to 50 ° C., more preferably in the range of 0 to 30 ° C. from the viewpoint of productivity.
- the time for bringing the crude product of the fluorinated hydrocarbon compound into contact with the hydrous metal salt of the synthetic crystal aluminosilicate is usually 1 hour to 72 hours.
- deHF compound produced by a decomposition reaction caused by contacting a crude product of a fluorinated hydrocarbon compound with a hydrous metal salt of a synthetic crystal aluminosilicate for example, as a deHF product of 2-fluorobutane, ( E) -2-butene, (Z) -2-butene, and 1-butene.
- the content of the deHF compound in the purified product of the fluorinated hydrocarbon compound after the contact treatment of the crude product of the fluorinated hydrocarbon compound and the hydrous metal salt of the synthetic crystal aluminosilicate is preferably 0.1% or less, More preferably, it is 0.05% or less.
- the purity of the purified product of the fluorinated hydrocarbon compound is usually 99.90% or more, preferably 99.95% or more on a volume basis.
- the amount of water contained in the purified product is usually on a volume basis. It is 50 ppm or less, preferably 30 ppm, more preferably 20 ppm or less.
- the temperature is raised to 800 ° C. at 10 ° C./min, and the total amount of carbon dioxide desorbed at this time is defined as the carbon dioxide adsorption amount ( ⁇ mol / g) of the hydrated metal salt of the synthetic crystal aluminosilicate.
- Example 1 5 g of molecular sieve MS3A (A) (product name: Zeorum (registered trademark) A3, manufactured by Tosoh Corporation) having an average pore size of 3 mm and 20 g of 2-fluorobutane are placed in a glass ampule bottle and immersed at 23 ° C. for 72 hours. did. The amount of deHF compound and the amount of water in 2-fluorobutane before and after immersion were measured. Moreover, the carbon dioxide adsorption amount of MS3A (A) before immersion was measured.
- A molecular sieve MS3A (A) (product name: Zeorum (registered trademark) A3, manufactured by Tosoh Corporation) having an average pore size of 3 mm and 20 g of 2-fluorobutane are placed in a glass ampule bottle and immersed at 23 ° C. for 72 hours. did. The amount of deHF compound and the amount of water in 2-fluorobutane before and after immersion were measured. Moreover, the carbon dioxide a
- Example 2 In the same manner as in Example 1, except that MS3A (B) (trade name: Molecular Sieve 3A pellet 1.6 manufactured by Union Showa Co., Ltd.) having an average pore diameter of 3 mm was used instead of MS3A (A) The amount of compound, the amount of water, and the carbon dioxide adsorption amount of MS3A (B) before immersion were measured.
- MS3A (B) trade name: Molecular Sieve 3A pellet 1.6 manufactured by Union Showa Co., Ltd.
- MS3A (C) having an average pore diameter of 3 mm was used in the same manner as in Example 1, and the amount of deHF compound, the amount of water, and the amount before immersion The amount of carbon dioxide adsorption of MS3A (C) was measured.
- Example 2 A deHF compound was obtained in the same manner as in Example 1 except that MS3A (D) (manufactured by Mizusawa Chemical Co., Ltd., product name: Mizuka Sieves (registered trademark) 3A) having an average pore diameter of 3 mm was used instead of MS3A (A). The amount, moisture content, and carbon dioxide adsorption amount of MS3A (D) before immersion were measured.
- MS3A (D) manufactured by Mizusawa Chemical Co., Ltd., product name: Mizuka Sieves (registered trademark) 3A
- Example 3 (Comparative Example 3) In the same manner as in Example 1, except that molecular sieve MS4A (trade name: Molecular Sieve 4A pellet 1.6, manufactured by Union Showa Co., Ltd.) having an average pore diameter of 4 mm was used instead of MS3A (A). The amount of compound, the amount of water, and the amount of carbon dioxide adsorbed by MS4A before immersion were measured.
- MS4A trade name: Molecular Sieve 4A pellet 1.6, manufactured by Union Showa Co., Ltd.
- Example 3 The amount of deHF compound, the amount of moisture, and the amount of carbon dioxide adsorption were measured in the same manner as in Example 1 except that 2-methyl-2-fluoropropane was used instead of 2-fluorobutane.
- Example 4 Except that 2-fluoropentane was used instead of 2-fluorobutane, the amount of deHF compound, the amount of water, and the amount of carbon dioxide adsorbed by MS3A (A) before immersion were measured in the same manner as in Example 1. .
- MS4A MS having an average pore diameter of 4 mm
- MS5A MS having an average pore diameter of 5 mm
Abstract
Description
半導体製造分野等で使用されるフッ素化炭素化合物は、高いエッチング選択性を実現するために、有機成分純度99.90%以上、かつ、水分濃度50ppm以下の高純度に精製することが求められる。このようなフッ素化炭化水素化合物の脱水方法としては、一般的な脱水剤であるMSを用いる方法が知られている。
しかし、フッ素化炭化水素化合物は、MSと接触すると、異性化や分解反応が起こりやすく、当該化合物の純度が低下する問題があった。
しかし、この文献には、炭素数4の不飽和フッ素化炭素化合物を用いた場合のみしか記載されていない。
そこで、本発明は、簡易な設備でフッ素化炭化水素化合物の粗製物とMSとを接触させても、分解反応により引き起こされる脱HF化合物の生成を抑制し、かつ効率よく水分を除去することができるフッ素化炭化水素化合物の精製方法を提供することを目的とする。
本発明の精製方法においては、前記鎖状飽和フッ素化炭化水素化合物が、末端の炭素原子にフッ素原子が結合していない鎖状飽和フッ素化炭化水素化合物であるのが好ましく、2-フルオロブタン、2-メチル-2-フルオロプロパン、2-フルオロペンタンからなる群より選択される化合物であるのがより好ましく、2-フルオロブタンであるのが特に好ましい。
本発明の精製方法によれば、分解反応により引き起こされる脱HF化合物の生成が抑制され、かつ効率よく水分を除去することができる。
C4H9F又はC5H11Fの例としては、1-フルオロブタン、2-フルオロブタン、1-フルオロ-2-メチルプロパン、2-フルオロ-2-メチルプロパン、1-フルオロペンタン、2-フルオロペンタン、3-フルオロペンタン、1-フルオロ-2-メチルブタン、1-フルオロ-3-メチルブタン、2-フルオロ-2-メチルブタン、2-フルオロ-3-メチルブタン、1-フルオロ-2,2-ジメチルプロパンが挙げられる。これらの中でも、本発明のより顕著な効果が得られる観点から、2-フルオロブタン、2-フルオロ-2-メチルプロパン、及び、2-フルオロペンタンからなる群より選択される、鎖状飽和フッ素化炭化水素化合物であるのがより好ましく、2-フルオロブタンであるのが特に好ましい。
フッ素化炭化水素化合物の粗製物と、合成結晶アルミノシリケートの含水金属塩との接触処理後におけるフッ素化炭化水素化合物の精製物中の脱HF化合物の含有量は、好ましくは0.1%以下、より好ましくは0.05%以下である。
また、前記精製物に含まれる水分量(すなわち、合成結晶アルミノシリケートの含水金属塩と接触させた後のフッ素化炭化水素化合物の精製物中に含まれる水分含有量)は、体積基準で、通常50ppm以下、好ましくは30ppm、より好ましくは20ppm以下である。
(1)合成結晶アルミノシリケートの含水金属塩の二酸化炭素吸着量の測定
合成結晶アルミノシリケートの含水金属塩の二酸化炭素吸着量(固体表面の塩基点の量)は、昇温脱離測定法(TPD法)により求めた。
合成結晶アルミノシリケートの含水金属塩0.1gを、全自動昇温脱離スペクトル装置(日本ベル社製、型名;TPD-1-ATw)の測定用セルに入れ、0.5体積%の二酸化炭素ガスを含むヘリウムガスを100ml/分で気流下、100℃で30分間保持した後に、ヘリウムガスに変更し、50ml/分の速度で30分間流す。さらに、10℃/分で800℃まで昇温し、このときに脱離した二酸化炭素量の合計を、合成結晶アルミノシリケートの含水金属塩の二酸化炭素吸着量(μmol/g)とする。
フッ素化炭化水素化合物の粗製物の浸漬処理前後における脱HF化合物量は、ガスクロマトグラフィーによりピーク面積から算出した。
・ガスクロマトグラフィー分析(GC分析)の条件は下記の通りである。
装置:Agilent(登録商標)7890A(アジレント社製)
カラム:ジーエルサイエンス社製、製品名「Inert Cap(登録商標)1」、長さ60m、内径0.25mm、膜厚1.5μm
カラム温度:40℃で20分間保持
インジェクション温度:80℃
キャリヤーガス:窒素
スプリット比:40/1
検出器:FID
(3)水分含有量の測定
フッ素化炭化水素化合物の粗製物の浸漬処理前後における水分含有量(vppm:Volumetric Parts per Million)は、FT-IRを測定することにより求めた。
測定装置:FT-IR測定装置(大塚電子社製、製品名:IG-1000))
セル長:10m
平均細孔径が3ÅのモレキュラーシーブMS3A(A)(東ソー社製、製品名;ゼオラム(登録商標)A3)5gと、2-フルオロブタン20gとを、ガラスアンプル瓶に入れ、23℃で72時間浸漬した。浸漬前後の2-フルオロブタン中の脱HF化合物量及び水分量を測定した。また、浸漬前のMS3A(A)の二酸化炭素吸着量を測定した。
MS3A(A)の代わりに、平均細孔径3ÅのMS3A(B)(ユニオン昭和社製、商品名:モレキュラーシーブ3Aペレット1.6)を用いた以外は、実施例1と同様にして、脱HF化合物量、水分量及び、浸漬前のMS3A(B)の二酸化炭素吸着量を測定した。
MS3A(A)の代わりに、平均細孔径3ÅのMS3A(C)(和光純薬社製)を用いた以外は、実施例1と同様にして、脱HF化合物量、水分量、及び浸漬前のMS3A(C)の二酸化炭素吸着量を測定した。
MS3A(A)の代わりに、平均細孔径3ÅのMS3A(D)(水澤化学社製、製品名;ミズカシーブス(登録商標)3A)を用いた以外は、実施例1と同様にして、脱HF化合物量、水分量、及び浸漬前のMS3A(D)の二酸化炭素吸着量を測定した。
MS3A(A)の代わりに、平均細孔径が4ÅのモレキュラーシーブMS4A(ユニオン昭和社製、商品名:モレキュラーシーブ4Aペレット1.6)を用いた以外は、実施例1と同様にして、脱HF化合物量、水分量、及び浸漬前のMS4Aの二酸化炭素吸着量を測定した。
MS3A(A)の代わりに、平均細孔径が5ÅのモレキュラーシーブMS5A(ユニオン昭和社製、商品名:モレキュラーシーブ5Aペレット1.6)を用いた以外は、実施例1と同様にして、脱HF化合物量、水分量、及び浸漬前のMS5Aの二酸化炭素吸着量を測定した。
2-フルオロブタンの代わりに、2-メチル-2-フルオロプロパンを用いた以外は、実施例1と同様にして、脱HF化合物量、水分量、二酸化炭素吸着量を測定した。
MS3A(A)の代わりに、MS3A(C)を用いた以外は、実施例3と同様にして、脱HF化合物量、水分量、及び浸漬前のMS3A(C)の二酸化炭素吸着量を測定した。
2-フルオロブタンの代わりに、2-フルオロペンタンを用いた以外は、実施例1と同様にして、脱HF化合物量、水分量、及び浸漬前のMS3A(A)の二酸化炭素吸着量を測定した。
MS3A(A)の代わりに、MS3A(C)を用いた以外は、実施例4と同様にして、脱HF化合物量、水分量、及び浸漬前のMS3A(C)の二酸化炭素吸着量を測定した。
実施例1~4、比較例1~6の結果を表1に示す。
一方で、前記鎖状フッ素化炭化水素化合物と、50μmol/g以上のMS3Aを接触させた場合は、浸漬処理後において脱HF化合物量が増加することがわかる(比較例1、2、5、6)。また、前記鎖状フッ素化炭化水素化合物と、接触させるMSがMS4A(平均細孔径が4ÅのMS)やMS5A(平均細孔径が5ÅのMS)の場合は、その二酸化炭素吸着量によらず、浸漬処理後において脱HF化合物量が増加することがわかる(比較例3、4)。
Claims (4)
- 式:C4H9F又はC5H11Fで表される鎖状飽和フッ素化炭化水素化合物の粗製物と、二酸化炭素吸着量が50μmol/g以下であり、かつ平均細孔径が3Åである合成結晶アルミノシリケートの含水金属塩とを接触させることにより、前記粗製物に含まれる水分を除去することを特徴とする鎖状飽和フッ素化炭化水素化合物の精製方法。
- 前記鎖状飽和フッ素化炭化水素化合物が、末端の炭素原子にフッ素原子が結合していないことを特徴とする請求項1に記載の精製方法。
- 前記鎖状飽和フッ素化炭化水素化合物が、2-フルオロブタン、2-メチル-2-フルオロプロパン、及び2-フルオロペンタンからなる群より選択される化合物であることを特徴とする請求項1又は2に記載の精製方法。
- 前記鎖状飽和フッ素化炭化水素化合物が、2-フルオロブタンであることを特徴とする請求項1~3のいずれかに記載の精製方法。
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EP14871549.3A EP3085681B1 (en) | 2013-12-20 | 2014-12-17 | Method for purifying hydrofluorocarbon compound |
JP2015553581A JP6380764B2 (ja) | 2013-12-20 | 2014-12-17 | フッ素化炭化水素化合物の精製方法 |
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PCT/JP2014/083406 WO2015093527A1 (ja) | 2013-12-20 | 2014-12-17 | フッ素化炭化水素化合物の精製方法 |
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US (1) | US9682906B2 (ja) |
EP (1) | EP3085681B1 (ja) |
JP (1) | JP6380764B2 (ja) |
KR (1) | KR20160098304A (ja) |
CN (1) | CN105764877B (ja) |
TW (1) | TWI619691B (ja) |
WO (1) | WO2015093527A1 (ja) |
Cited By (1)
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WO2016117463A1 (ja) * | 2015-01-22 | 2016-07-28 | 日本ゼオン株式会社 | フッ素化炭化水素化合物の精製方法 |
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JP6835061B2 (ja) * | 2018-12-28 | 2021-02-24 | ダイキン工業株式会社 | ヘキサフルオロブタジエンの精製方法 |
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- 2014-12-17 WO PCT/JP2014/083406 patent/WO2015093527A1/ja active Application Filing
- 2014-12-17 US US15/103,747 patent/US9682906B2/en not_active Expired - Fee Related
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WO2016117463A1 (ja) * | 2015-01-22 | 2016-07-28 | 日本ゼオン株式会社 | フッ素化炭化水素化合物の精製方法 |
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Also Published As
Publication number | Publication date |
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JP6380764B2 (ja) | 2018-08-29 |
KR20160098304A (ko) | 2016-08-18 |
CN105764877A (zh) | 2016-07-13 |
US20160318832A1 (en) | 2016-11-03 |
EP3085681A4 (en) | 2017-05-10 |
TWI619691B (zh) | 2018-04-01 |
TW201524940A (zh) | 2015-07-01 |
US9682906B2 (en) | 2017-06-20 |
EP3085681A1 (en) | 2016-10-26 |
CN105764877B (zh) | 2017-07-11 |
EP3085681B1 (en) | 2019-05-08 |
JPWO2015093527A1 (ja) | 2017-03-23 |
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