WO2008001844A1 - Procédé de production d'hexafluoropropylène à haut degré de pureté et gaz nettoyant - Google Patents

Procédé de production d'hexafluoropropylène à haut degré de pureté et gaz nettoyant Download PDF

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Publication number
WO2008001844A1
WO2008001844A1 PCT/JP2007/062995 JP2007062995W WO2008001844A1 WO 2008001844 A1 WO2008001844 A1 WO 2008001844A1 JP 2007062995 W JP2007062995 W JP 2007062995W WO 2008001844 A1 WO2008001844 A1 WO 2008001844A1
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WIPO (PCT)
Prior art keywords
hexafluoropropylene
purity
content
crude
less
Prior art date
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PCT/JP2007/062995
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English (en)
Japanese (ja)
Inventor
Hiromoto Ohno
Toshio Ohi
Original Assignee
Showa Denko K.K.
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 Showa Denko K.K. filed Critical Showa Denko K.K.
Priority to JP2008522621A priority Critical patent/JP5132555B2/ja
Publication of WO2008001844A1 publication Critical patent/WO2008001844A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/44—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the method of coating
    • C23C16/4401—Means for minimising impurities, e.g. dust, moisture or residual gas, in the reaction chamber
    • C23C16/4405—Cleaning of reactor or parts inside the reactor by using reactive gases
    • 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
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
    • 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

Definitions

  • the present invention relates to a method for producing high-purity hexafluoropropylene.
  • the present invention relates to a method for producing hexafluoropropylene and a use of high-purity hexafluoropropylene which are preferably used for removing deposits in a semiconductor production apparatus or a liquid crystal production apparatus.
  • CF CF CF
  • FC-1216 Hexafluoropropylene
  • C F cleaning gas fluorinated propane
  • Tylene (CF CC1F), dichlorodifluoromethane (CC1 F), etc. are hexafluoropro
  • Patent Document 1 JP-A-4-145503
  • Patent Document 2 JP-A-9 296271
  • Patent Document 3 Japanese Patent Laid-Open No. 10-27781
  • Patent Document 4 Japanese Patent Laid-Open No. 2005-26409
  • the present invention is intended to solve the problems associated with the prior art as described above, and is a method for industrially advantageously producing high purity hexafluoropropylene, and its high purity.
  • the purpose of the hexafluoropropylene is to provide a cleaning gas for removing deposits in a semiconductor manufacturing apparatus or a liquid crystal manufacturing apparatus.
  • the present invention is configured by the following [1] to [15].
  • step (2) A step of reducing the content of low boiling point components in hexafluoropropylene obtained in step (1) by distillation.
  • a process for producing high purity hexafluoropropylene comprising:
  • the chlorine-containing compound has the general formula: CH C1 F (wherein v is an integer of 1 to 4, x is an integer of 0 to 2, y is an integer of 1 to 3, z is 1 to
  • the chlorine-containing compound may be dichlorodifluoromethane, dichlorofluoromethane, Is at least one selected from the group consisting of difluororeomethane, chlorofluoroethylene, chlorotrifluoroethylene, chlorotetrafluoroethane, black pentafluoroethane, and black hexafluoropropane;
  • the method for producing high-purity hexafluoropropylene as described in [1] above.
  • the above zeolite is a zeolite having a silica Z aluminum ratio of 2.0 or less.
  • the content of chlorine-containing compounds is 20 volppm or less, the content of hydrated carbons is 3 Ovolppm or less, and the content of low-boiling components is 20 volppm or less, and the purity is 99.99 vol% or more.
  • high-purity hexafluoropropylene can be efficiently produced by a simple method, and the obtained high-purity hexafluoropropylene is used in a semiconductor manufacturing apparatus.
  • it can be suitably used as a plasma cleaning gas for removing deposits in the liquid crystal manufacturing apparatus.
  • the method for producing high-purity hexafluoropropylene according to the present invention is a method for producing high-purity hexafluoropropylene by purifying crude hexafluoropropylene. Specifically, (1) the above crude hexafluoropropylene, zeolite having an average pore size of 3.4 A to llA, and Z or a carbonaceous adsorbent having an average pore size of 3.5 A to 11 A A step of reducing the content of chlorine-containing compounds and Z or hard mouth carbons in the crude hexafluoropropylene by contacting with a powerful adsorbent; (2) obtained in the above step (1) And reducing the content of low boiling components in the hexafluoropropylene by distillation.
  • Crude hexafluoropropylene used in the present invention is produced as a by-product in the production of tetrafluoroethylene via thermal decomposition of chlorodifluoromethane.
  • HFC Hyde mouth fluorocarbons
  • HC hydrocarbons
  • the chlorine-containing compound may be represented by the general formula: CH C1 F (wherein V is an integer of 1 to 4, x is an integer of 0 to 2, y is an integer of 1 to 3, and z is 1 to 6) An integer, a compound represented by 2v ⁇ x + y + z ⁇ 2v + 2), is included, and crude hexafluoropropylene contains one or more of these compounds.
  • Specific examples of the compound represented by the above general formula include dichlorodifluoromethane (CC1 F), dichlorofluoromethane (CHC1 F), chlorodifluoromethane (CHC1
  • the content of the chlorine-containing compound in xafluoropropylene is preferably 0.05 vol% or less.
  • the content of drofluorocarbons is preferably 0.05 vol% or less! /.
  • the content of the above-mentioned hide mouth carbons is 0.05 vol% or less.
  • the adsorbent used in the present invention includes (1) a zeolite having an average pore diameter of 3.4 A to llA, (2) a carbonaceous adsorbent having an average pore diameter of 3.5 A to llA, or (3) the above It is a mixture of zeolite and the above carbonaceous adsorbent.
  • Zeolite having an average pore diameter in the above range is excellent in the effect of reducing the content of impurities in crude hexafluoropropylene.
  • the carbonaceous adsorbent having an average pore diameter in the above range is excellent in the effect of reducing the content of impurities in the crude hexafluoropropylene.
  • zeolite having a silica-Z aluminum ratio of 2.0 or less is more preferable in that the effect of reducing the content of impurities is further improved.
  • the zeolite used in the method for producing high-purity hexafluoropropylene of the present invention has an average pore diameter of 3.4 to: L 1A, preferably 3.4 to: LOA. Is there Is good. Zeolite with an average pore size larger than 11 A increases the amount of hexafluoropropylene adsorbed, and zeolite with an average pore size smaller than 3.4 A has the ability to adsorb chlorine-containing compounds and hydrocarbons. May be smaller.
  • the ratio of zeolite (Si) (silica) ZA1 (aluminum) is preferably 2.0 or less. When the SiZAl ratio is greater than 2, chlorine-containing compounds and hydrated carbons are selectively adsorbed. It may not be done.
  • Zeolite includes molecular sieves 4A (MS-4A, made by Yuon Showa Co., Ltd.), molecular sieves 5A (MS-5A, made by Union Showa Co., Ltd.), molecular sieves 10X (MS-10A, made by Union Showa Co., Ltd.) and Molecular sieves 13X (MS-13X, manufactured by Union Showa Co., Ltd.) At least one kind of zeolite selected from the group that also has power is preferred.
  • activated carbon and molecular sieving carbon are known as carbonaceous adsorbents.
  • Activated carbon is activated carbon made from coconut shell, coal, wood, etc., and carbonized at a high temperature and then activated by applying a special treatment to generate pores in the raw material, which has a wide range of uses as an excellent adsorbent.
  • molecular sieve having a highly controlled pore size! /, Molecular sieve carbon which is activated carbon.
  • the carbonaceous adsorbent has an average pore diameter of 3.5 to: L1A.
  • the carbonaceous adsorbent having an average pore diameter larger than 11 A is adsorbed by hexafluoropropylene.
  • Carbonaceous adsorbents with an average pore size of less than 3.5A may have a reduced ability to adsorb chlorine-containing compounds and hydrocarbons.
  • molecular sieve carbon 4A for example, manufactured by Takeda Pharmaceutical Co., Ltd.
  • molecular sieve carbon 5A for example, manufactured by Takeda Pharmaceutical Co., Ltd.
  • the mixing ratio of the zeolite and the carbonaceous adsorbent is not particularly limited, and the type and content of impurities in the crude hexafluoropropylene are not limited. It is set appropriately depending on the amount.
  • the content of chlorine-containing compounds and Z or hydrated carbons is reduced by bringing the adsorbent into contact with crude hexafluoropropylene.
  • Crude hexafluoropropylene during contact of adsorbent with crude hexafluoropropylene There is no particular limitation on the state of, for example, rough hexafluoropropylene force, a method of contacting in a gas state, a method of contacting in a gas-liquid mixed state, or a method of contacting in a liquid state. Force that can be used by the method The method of contacting in the liquid state is preferable because of its high efficiency.
  • the method for contacting the adsorbent with the crude hexafluoropropylene is not particularly limited.
  • a known method such as a batch method or a continuous method can be used.
  • two fixed bed type adsorption towers are generally provided, and when one reaches saturation adsorption, this is switched and regenerated.
  • the conditions for the contact treatment are not particularly limited, but the treatment temperature is preferably a low temperature.
  • a temperature range of ⁇ 50 to 50 ° C. is more preferred, and a temperature range of ⁇ 20 to 30 ° C. is more preferred.
  • the treatment pressure is not particularly limited as long as the crude hexafluoropropylene is brought into contact in a liquid state as long as the pressure can be maintained in the liquid state, and when the contact is made in a gas state.
  • the crude hexafluoropropylene Prior to contacting with the adsorbent, the crude hexafluoropropylene is introduced into a distillation column in advance to remove low boiling components (low boiling cut) and high boiling components (high boiling cut). In this case, however, there is a possibility that low-boiling components may be mixed from the adsorbent, and it is necessary to remove low-boiling components again. Therefore, in the production method according to the present invention, (1) the crude hexafluoropropylene and the adsorbent are contacted, and then (2) the hexafluoropropylene obtained in this step (1) is distilled. And a step of reducing the content of low boiling components.
  • the high-boiling component in the scouring and crude hexafluoropropylene is reduced in advance before the contact step (1). It is preferable to have a step of distilling crude hexafluoropropylene to reduce the content of high-boiling components in the crude hexafluoropropylene.
  • Examples of the low boiling point component include nitrogen, oxygen, carbon monoxide, carbon dioxide, and a mixture of two or more thereof.
  • the contents of chlorine-containing compounds, hydrated carbons, and low-boiling components can be reduced.
  • High purity hexafluoropropylene having a purity of 99.99 vol% or more can be obtained.
  • the content of chlorine-containing compounds in high-purity hexafluoropropylene is preferably 20 volppm or less.
  • the content of hydrated carbons is more preferably 30 volppm or less.
  • the content of hydrated carbons is more preferably 20 volppm or less.
  • the content of low boiling components is preferably 20 volppm or less, more preferably 10 volppm or less.
  • Such high-purity hexafluoropropylene can be used as a cleaning gas for removing deposits in a semiconductor manufacturing apparatus or a liquid crystal manufacturing apparatus. At this time, high purity hexafluoropropylene may be used alone, but depending on the cleaning conditions, He, Ar, N
  • Ne, Kr, or group power that also has oxygen-containing compound power At least one type of dilution gas selected may be added.
  • oxygen-containing compound O
  • the amount of applied force of these dilution gases is 40 vol% or less.
  • the semiconductor manufacturing apparatus When the semiconductor manufacturing apparatus is cleaned using the cleaning gas, it may be cleaned under plasma conditions or may be cleaned under plasmaless conditions.
  • the excitation source is not particularly limited as long as the above-described cleaning gas force plasma is excited, but the use of a microwave excitation source is preferable because the cleaning efficiency is good.
  • the temperature range and pressure range in which the cleaning gas of the present invention is used are not particularly limited as long as they generate plasma. However, temperatures in the range of 50 to 500 ° C are preferred. A pressure in the lMPa range is preferred.
  • a cleaning gas is introduced into the chamber, and preferably the pressure in the chamber is set in the range of 0.05 to lMPa.
  • the cleaning gas is activated by heating at least one or both of them to a temperature in the range of 150 to 500 ° C., and the region force in which the chamber and other deposits are accumulated also etches the deposits. By removing it, the semiconductor manufacturing equipment can be tallyed.
  • the liquid phase part obtained in the above step (1) is introduced into the distillation column, the low boiling component is extracted from the top of the distillation column (low boiling cut), and the liquid phase part is extracted from the bottom of the distillation column.
  • This liquid phase part was analyzed by a gas chromatograph [“GC-14A” manufactured by Shimadzu Corporation, column: Pompack-Q (6 m) manufactured by Shimadzu Corporation, measurement temperature: 80 to 200 ° C.]. The results are shown in Table 1.
  • Carbonaceous adsorbent (molecular scrubbing force) on a 200 ml stainless steel cylinder —Bonn 5A, Takeda Pharmaceutical Co., Ltd .: average pore size 5A) was filled with 20 g and vacuum dried. Next, while cooling the cylinder, about 60 g of the crude hexafluoropropylene obtained in Preparation Example 1 above was charged and stirred occasionally at room temperature, and the liquid phase portion after about 12 hours was recovered with a filling power of about 12 hours. did . This liquid phase part was analyzed with a gas chromatograph [“GC-14A” manufactured by Shimadzu Corporation, column: Porapack-Q (6 m) manufactured by Shimadzu Corporation, measurement temperature: 80 to 200 ° C.]. The results are shown in Table 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cleaning Or Drying Semiconductors (AREA)

Abstract

La présente invention concerne un procédé industriellement avantageux de production d'hexafluoropropylène à haut degré de pureté ; et l'utilisation de cet hexafluoropropylène à haut degré de pureté, spécifiquement en tant que gaz nettoyant destiné à éliminer les dépôts dans un appareil de fabrication de semiconducteurs ou un appareil de fabrication de cristaux liquides. Selon le procédé de production d'hexafluoropropylène à haut degré de pureté, l'hexafluoropropylène brut produit par la pyrolyse de chlorodifluorométhane est purifié afin de produire l'hexafluoropropylène à haut degré de pureté. Ledit procédé comprend : une étape (1) au cours de laquelle l'hexafluoropropylène brut est mis au contact d'un adsorbent comprenant une zéolite dont les micropores ont un diamètre moyen de 3,4 à 11 Å et/ou au contact d'un adsorbent carboné dont les micropores ont un diamètre moyen de 3,5 à 11 Å pour réduire la teneur en composés de chlore et/ou en hydrocarbures dans l'hexafluoropropylène brut ; et une étape (2) au cours de laquelle l'hexafluoropropylène obtenu à l'étape (1) est distillé afin de réduire sa teneur en ingrédients à bas point d'ébullition.
PCT/JP2007/062995 2006-06-30 2007-06-28 Procédé de production d'hexafluoropropylène à haut degré de pureté et gaz nettoyant WO2008001844A1 (fr)

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WO2010001025A2 (fr) * 2008-07-03 2010-01-07 Arkema France PROCEDE DE PURIFICATION DE 2,3,3,3-TETRAFLUORO-1-PROPENE (HF01234yf)
WO2010115734A1 (fr) 2009-04-01 2010-10-14 Solvay Fluor Gmbh Procédé de fabrication d'articles gravés
WO2011045559A1 (fr) * 2009-10-15 2011-04-21 Mexichem Amanco Holding S.A. De Cv. Procédé de purification d'(hydro)fluoroalcènes
KR101198349B1 (ko) 2011-04-05 2012-11-06 (주)원익머트리얼즈 고순도 헥사플루오르프로필렌 정제방법
KR101198351B1 (ko) 2011-04-05 2012-11-06 (주)원익머트리얼즈 고순도 헥사플루오르프로필렌 정제장치
KR101198350B1 (ko) 2011-04-05 2012-11-08 (주)원익머트리얼즈 고순도 헥사플루오르프로필렌 정제용기
US8410244B2 (en) 2009-07-06 2013-04-02 Mitsubishi Gas Chemical Company, Inc. Vibration-damping film
WO2013106046A2 (fr) * 2011-04-20 2013-07-18 Honeywell International Inc. Purification de trans-1,3,3,3-tétrafluoropropène
WO2013151070A1 (fr) * 2012-04-03 2013-10-10 旭硝子株式会社 Procédé de purification d'oléfine fluorée, et procédé de production d'oléfine fluorée
JP2013241390A (ja) * 2012-04-27 2013-12-05 Asahi Glass Co Ltd フルオロオレフィンの精製方法、およびフルオロオレフィンの製造方法
AU2013204796B2 (en) * 2009-10-15 2014-09-11 Mexichem Amanco Holding S.A. De C.V. Process for purifying (hydro) fluoroalkenes
KR101433626B1 (ko) 2013-05-22 2014-09-23 (주)원익머트리얼즈 헥사플루오르플로필렌옥사이드 고순도 정제방법
JP2017092357A (ja) * 2015-11-16 2017-05-25 セントラル硝子株式会社 ドライエッチングガスおよびドライエッチング方法
CN111250038A (zh) * 2020-03-09 2020-06-09 临海市利民化工有限公司 一种六氟丙烯二聚体的分离纯化方法及所用吸附剂
JP2022141845A (ja) * 2013-03-15 2022-09-29 ハネウェル・インターナショナル・インコーポレーテッド ２，３，３，３－テトラフルオロプロペン生成物中のハロゲン化エチレン不純物を除去する方法
WO2024111416A1 (fr) * 2022-11-25 2024-05-30 Ａｇｃ株式会社 Procédé de séparation d'hexafluoropropylène à partir de chlorodifluorométhane

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US10995047B2 (en) 2013-03-15 2021-05-04 The Chemours Company Fc, Llc Process for the reduction of RƒC≡CX impurities in fluoroolefins
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US8252964B2 (en) 2008-07-03 2012-08-28 Arkema France Process for the purification of 2,3,3,3-tetrafluoro-1-propene (HFO-1234yf)
FR2933402A1 (fr) * 2008-07-03 2010-01-08 Arkema France Procede de purification de 2,3,3,3-tetrafluoro-1-propene (hfo1234yf)
WO2010001025A3 (fr) * 2008-07-03 2010-03-11 Arkema France PROCEDE DE PURIFICATION DE 2,3,3,3-TETRAFLUORO-1-PROPENE (HF01234yf)
CN102076645B (zh) * 2008-07-03 2014-02-26 阿克马法国公司 用于纯化2,3,3,3-四氟-1-丙烯(HFO-1234yf)的方法
CN102076645A (zh) * 2008-07-03 2011-05-25 阿克马法国公司 用于纯化2,3,3,3-四氟-1-丙烯(HFO-1234yf)的方法
WO2010001025A2 (fr) * 2008-07-03 2010-01-07 Arkema France PROCEDE DE PURIFICATION DE 2,3,3,3-TETRAFLUORO-1-PROPENE (HF01234yf)
WO2010115734A1 (fr) 2009-04-01 2010-10-14 Solvay Fluor Gmbh Procédé de fabrication d'articles gravés
US8410244B2 (en) 2009-07-06 2013-04-02 Mitsubishi Gas Chemical Company, Inc. Vibration-damping film
KR20120083909A (ko) * 2009-10-15 2012-07-26 멕시켐 아만코 홀딩 에스.에이. 데 씨.브이. (하이드로)플루오로알켄 정제 방법
KR101721598B1 (ko) * 2009-10-15 2017-03-30 멕시켐 아만코 홀딩 에스.에이. 데 씨.브이. (하이드로)플루오로알켄 정제 방법
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EP2952500B1 (fr) 2009-10-15 2018-09-26 Mexichem Fluor S.A. de C.V. Procédé de purification d'(hydro) fluoroalcènes
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