JP5872899B2 - フッ素化材料の熱分解によるフルオロオレフィンの製造プロセス - Google Patents
フッ素化材料の熱分解によるフルオロオレフィンの製造プロセス Download PDFInfo
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- FOKCKXCUQFKNLD-UHFFFAOYSA-N pent-1-enyl hypofluorite Chemical compound C(CC)C=COF FOKCKXCUQFKNLD-UHFFFAOYSA-N 0.000 description 1
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- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
- C07C17/367—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms by depolymerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(i)炭化水素をフッ素化してフッ素化された炭化水素を生成する工程と、
(ii)マイクロ波照射の存在下でフッ素化材料をフルオロオレフィンに熱分解することを行う熱分解プロセスにフッ素化された炭化水素を供する工程と、を含むプロセスを提供する。
本願で言うところのフッ素化材料には、フルオロポリマー、フルオロポリマーを含む組成物、及びフルオロポリマー含有物品が含まれる。
低分子量のフッ素化有機化合物は、約1,000g/molよりも低い分子量を有する。これらの化合物は室温(25℃)で液体又は気体でありうる。
本願で言うところのフルオロポリマーとは、フッ素化された主鎖を有するポリマーである。フルオロポリマーは、例えばテトラフルオロエチレン(TFE)、ヘキサフルオロプロピレン(HFP)、フッ化ビニリデン(VDF)、クロロトリフルオロエチレン(CTFE)、例えばパーフルオロメチルビニルエーテル(PMVE)、パーフルオロプロピルビニルエーテル、パーフルオロイソプロピルビニルエーテルなどの過フッ素化又は部分フッ素化アルキルビニルエーテル、過フッ素化又は部分フッ素化アリルエーテル又はビニルエーテルなどのフッ素化オレフィンから誘導される繰り返し単位を含みうる。パーフルオロビニルエーテルの例としては下式に対応するものが挙げられる。
CF2=CF−O−Rf
式中、Rfは、1以上の酸素原子を含みうる過フッ素化された直鎖、環状、又は分枝鎖の脂肪族基、特に下式に対応する過フッ素化ビニルエーテルを表す。
CF2=CFO(Ra fO)n(Rb fO)mRc f
式中、Ra f及びRb fは、1〜6個の炭素原子、特に2〜6個の炭素原子を有する異なる直鎖又は分枝鎖又は環状パーフルオロアルキレン基であり、m及びnは独立して0〜10であり、Rc fは1〜6個の炭素原子を有するパーフルオロアルキル基である。過フッ素化ビニルエーテルの具体例としては、パーフルオロ(メチルビニル)エーテル(PMVE)、パーフルオロ(エチルビニル)エーテル(PEVE)、パーフルオロ(n−プロピルビニル)エーテル(PPVE−1)、パーフルオロ−2−プロポキシプロピルビニルエーテル(PPVE−2)、パーフルオロ−3−メトキシ−n−プロピルビニルエーテル、パーフルオロ−2−メトキシ−エチルビニルエーテル、及びCF3−(CF2)2−O−CF(CF3)−CF2−O−CF(CF3)−CF2−O−CF=CF2又はCF2=CF−O−(CF2)3OCF3、又はCF2=CFO(CF2)2OCF3が挙げられる。
CF2=CF−CF2−O−Rf
式中、Rfは、1以上の酸素原子を含みうる過フッ素化された直鎖、環状、又は分枝鎖脂肪族基、特に下式に対応するものを表す。
CF2=CFCF2O(Ra fO)n(Rb fO)mRc f式中、各残基は対応するビニルエーテルについて上記に述べたものと同じ意味を有する。
フルオロオレフィンには下記一般式に対応するオレフィンが含まれる。
CF2=CF−Rd f
式中、Rd fは、F、又は1〜10個、好ましくは1〜5個の炭素原子を有するパーフルオロアルキル基を表す。フロオロオレフィンの一般的な例としては、テトラフルオロエチレン(TFE)及びヘキサフルオロプロピレン(HFP)が挙げられる。
フッ素化材料のフッ素化オレフィンへの熱分解は、熱分解反応に必要な温度を発生させることが可能な任意の適当な反応器内で行うことができる。例えば、熱分解はロータリーキルン反応器内で行うことができる。ロータリーキルン反応器は例えば、イチダ(Ichida)らに付与された欧州特許出願公開第1 481 957号に述べられている。分解反応は、例えばファン・デル・ウォルト(Van der Walt)らに付与された国際特許出願公開第WO 2007/063462 A1号に述べられる装置のような押出成形機型の反応装置内で行うこともできる。これらの装置は例えば、キャリアガス又はガス状反応媒質などのガス流の存在下又は非存在下で運転することが可能である。好ましくは、分解反応は流動床反応器(例えば、J.R.Howard,「Fluidized Bed Technology,Principles and Applications」,Adam Hingler,New York,1989を参照)中で行われる。一般的に、流動化媒質としてはガス又はガス混合物を用いる。キャリアガス又はガス状の流動化又は反応媒質は一般的に、例えば水蒸気、窒素、希ガス(Xe、Ar、Ne、Heなど)及びこれらの混合物などの非反応性ガス(すなわち、反応器内での分解条件下で反応しないガス)を含む。窒素、希ガス及びこれらの混合物が好ましい。しかしながら、キャリアガス及び/又は媒質は反応性ガス(すなわち、反応器内の条件下でやはり分解して、TFE及び/又はHFPに変換されうるフッ素含有ガス)を含むか、あるいは反応性ガスからなるものでもよい。
水酸化カリウム水溶液の体積流は、急冷温度が約40℃となるように調節した。生成混合物をその組成及びTFE含量についてガスクロマトグラフィーで分析した。
Sl/分=標準リットル/分=1SL/分は1.68875(Pa×m3)/sに相当。
Claims (2)
- フッ素化材料からフッ素化オレフィンを製造するためのプロセスであって、マイクロ波照射の存在下及びガス状流動床の存在下で前記フッ素化材料をフルオロオレフィンに熱分解する工程を含み、前記フッ素化材料は550℃〜700℃の温度で熱分解され、マイクロ波活性粒子がガス状流動床中に存在する、プロセス。
- テトラフルオロエチレンを生成するためのプロセスであって、
(i)炭化水素をフッ素化してフッ素化された炭化水素を生成する工程と、
(ii)前記フッ素化された炭化水素を請求項1に記載の熱分解プロセスに供する工程
と、を含む、プロセス。
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PCT/US2009/059011 WO2010039820A2 (en) | 2008-10-01 | 2009-09-30 | Process of making fluoroolefins by thermal decomposition of fluorinated materials |
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EP3002273A1 (en) | 2014-10-01 | 2016-04-06 | 3M Innovative Properties Company | Process and apparatus for producing fluorinated alkenes |
CN108129253B (zh) * | 2017-12-21 | 2020-05-12 | 上海微谱化工技术服务有限公司 | 一种epdm的分析方法 |
US10636655B2 (en) * | 2018-03-19 | 2020-04-28 | Applied Materials, Inc. | Methods for asymmetric deposition of metal on high aspect ratio nanostructures |
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CN109912384A (zh) * | 2019-04-04 | 2019-06-21 | 浙江大学 | 一种从二氯丙烯多聚体中回收二氯丙烯的催化方法 |
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