JP6965397B2 - クロロトリフルオロエチレンの製造方法 - Google Patents
クロロトリフルオロエチレンの製造方法 Download PDFInfo
- Publication number
- JP6965397B2 JP6965397B2 JP2020081064A JP2020081064A JP6965397B2 JP 6965397 B2 JP6965397 B2 JP 6965397B2 JP 2020081064 A JP2020081064 A JP 2020081064A JP 2020081064 A JP2020081064 A JP 2020081064A JP 6965397 B2 JP6965397 B2 JP 6965397B2
- Authority
- JP
- Japan
- Prior art keywords
- fluorinated
- catalyst
- zero
- metal
- chlorinated
- Prior art date
- Legal status (The legal status 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 status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/10—Chlorides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/12—Fluorides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/132—Halogens; Compounds thereof with chromium, molybdenum, tungsten or polonium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/138—Halogens; Compounds thereof with alkaline earth metals, magnesium, beryllium, zinc, cadmium or mercury
-
- 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
- C07C17/42—Use of additives, e.g. for stabilisation
-
- 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
- C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
- C07C19/12—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine having two carbon atoms
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/10—Magnesium; Oxides or hydroxides thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/10—Constitutive chemical elements of heterogeneous catalysts of Group I (IA or IB) of the Periodic Table
- B01J2523/11—Lithium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/10—Constitutive chemical elements of heterogeneous catalysts of Group I (IA or IB) of the Periodic Table
- B01J2523/12—Sodium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/10—Constitutive chemical elements of heterogeneous catalysts of Group I (IA or IB) of the Periodic Table
- B01J2523/13—Potassium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/10—Constitutive chemical elements of heterogeneous catalysts of Group I (IA or IB) of the Periodic Table
- B01J2523/15—Caesium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/10—Constitutive chemical elements of heterogeneous catalysts of Group I (IA or IB) of the Periodic Table
- B01J2523/17—Copper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/20—Constitutive chemical elements of heterogeneous catalysts of Group II (IIA or IIB) of the Periodic Table
- B01J2523/22—Magnesium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/20—Constitutive chemical elements of heterogeneous catalysts of Group II (IIA or IIB) of the Periodic Table
- B01J2523/23—Calcium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/20—Constitutive chemical elements of heterogeneous catalysts of Group II (IIA or IIB) of the Periodic Table
- B01J2523/27—Zinc
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/60—Constitutive chemical elements of heterogeneous catalysts of Group VI (VIA or VIB) of the Periodic Table
- B01J2523/67—Chromium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/60—Constitutive chemical elements of heterogeneous catalysts of Group VI (VIA or VIB) of the Periodic Table
- B01J2523/68—Molybdenum
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/70—Constitutive chemical elements of heterogeneous catalysts of Group VII (VIIB) of the Periodic Table
- B01J2523/72—Manganese
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/80—Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
- B01J2523/82—Metals of the platinum group
- B01J2523/821—Ruthenium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/80—Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
- B01J2523/82—Metals of the platinum group
- B01J2523/824—Palladium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/80—Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
- B01J2523/82—Metals of the platinum group
- B01J2523/825—Osmium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/80—Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
- B01J2523/82—Metals of the platinum group
- B01J2523/827—Iridium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/80—Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
- B01J2523/82—Metals of the platinum group
- B01J2523/828—Platinum
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/80—Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
- B01J2523/84—Metals of the iron group
- B01J2523/842—Iron
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/80—Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
- B01J2523/84—Metals of the iron group
- B01J2523/845—Cobalt
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/80—Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
- B01J2523/84—Metals of the iron group
- B01J2523/847—Nickel
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
(HCFC−123a)からクロロトリフルオロエチレン(CFO−1113)を製造する方法に関する。
FE)又はCFO−1113とも命名されている)は、極低温用途において冷媒として通常的に用いられている。CFO−1113は炭素−炭素二重結合を有しており、したがって重合してポリクロロトリフルオロエチレンを形成するか、又は共重合してプラスチックECTFEを製造することができる。クロロトリフルオロエチレン(CFO−1113)は、現在は、溶媒としてメタノールの存在下において亜鉛と反応させることにより1,1,2−トリクロロトリフルオロエタン(CFC−113)を脱塩素化することによって商業的に製造されている。このプロセスに関する主要な欠点は、主要副生成物として1,2−ジクロロ−1,1,2−トリフルオロエタン(HCFC−123a)が形成され、これによってCFO−1113の収量が大きく減少し、同時に廃棄するのが高コストであることである。
。
Cl、LiF、NaF、KF、及び/又はCsFの1以上は、MgF2と組合せた触媒の全重量を基準として約5.0重量%〜約50重量%の量で存在する。
コネル625合金である。1つの好ましい態様においては、金属合金反応容器の表面、好ましい態様においては容器の内表面を、HCFC−123aの脱塩化水素化のための触媒として機能させることができる。
脱塩化水素化は、場合によっては酸化剤の存在下又は不存在下で行うことができる。酸
化剤の有用な例としては酸素及び二酸化炭素が挙げられるが、これらに限定されない。酸化剤を用いることによって、触媒の寿命を延ばすことができる。酸化剤は純粋であってよく、或いは反応器中に導入する前に窒素のような不活性ガスで希釈することができる。酸化剤のレベルは、一般に、有機供給材料の体積を基準として約1体積%〜約10体積%、好ましくは約2体積%〜5体積%である。
実施例1:
約40mLの10%CsCl/MgF2触媒を、3/4インチ×0.035インチの管状インコネル625反応器中に充填した。反応器を、電気式3区画分割炉の中央部内に設置した。反応器の内部及び触媒床内に配置した多点式熱電対を用いてプロセス温度を記録した。反応器を、まず窒素流中で所望の温度に加熱し、次に純度94.6%のHCFC−123aを含む流れを、垂直に設置した反応器の底部中に12g/時の供給速度で供給して反応を開始させた。反応器圧力は1気圧に設定した。反応器流出流を周期的にサンプリングし、GC−MS及びGCによってその組成に関して分析して、原材料の転化率レベル及び生成物の選択率を求めた。
HCFC−123aの脱塩化水素化のために、約40mLのフッ素化15重量%Cs2O/MgO触媒を、実施例1に記載したものと同じ3/4インチ×0.035インチの管状インコネル625反応器中に装填した。反応器を窒素流中で480℃に加熱した。温度が安定した後、純度94.6%のHCFC−123a供給材料を、12グラム/時(g/時)の速度で触媒床に通した。反応器圧力は1気圧に設定した。表2に示すように、15重量%Cs2O/MgO触媒によって、平均で約15%のHCFC−123aの転化率及び約95%のCFO−1113の選択率が与えられた。
HCFC−123aの脱塩化水素化のために、約40mLの1重量%Pd/MgO触媒を、実施例1に記載したものと同じ3/4インチ×0.035インチの管状インコネル625反応器中に装填した。反応器を窒素流中で450℃に加熱した。温度が安定した後、純度94.6%のHCFC−123a供給材料を、12グラム/時(g/時)の速度で触媒床に通した。反応器圧力は1気圧に設定した。表3に示すように、1重量%Pd/MgO触媒によって、約10%のHCFC−123aの転化率及び約97%のCFO−1113の選択率が与えられた。
本発明は以下の態様を含む。
[1]
(i)1種類以上の金属ハロゲン化物;(ii)1種類以上のハロゲン化金属酸化物;(iii)1種類以上の0価の金属又は金属合金;(iv)これらの組合せ;からなる群から選択される触媒の存在下で1,2−ジクロロ−1,1,2−トリフルオロエタン(HCFC−123a)を脱塩化水素化して、CFO−1113を含む反応生成物を生成させる;
ことを含む、クロロトリフルオロエチレン(CFO−1113)の製造方法。
[2]
HCFC−123aの転化率が少なくとも約5重量%であり、クロロトリフルオロエチレンへの選択率が少なくとも約70重量%であり、反応生成物は約10重量%未満のCFO−1112を含む、[1]に記載の方法。
[3]
脱塩化水素化工程の相当部分を約480℃〜約550℃の温度において行う、[2]に記載の方法。
[4]
触媒が少なくとも1種類の金属ハロゲン化物を含み、成分の金属は、Cr 3+ 、Fe 3+ 、Mg 2+ 、Ca 2+ 、Ni 2+ 、Zn 2+ 、Pd 2+ 、Li + 、Na + 、K + 、及びCs + からなる群から選択され、成分のハロゲンは、F − 、Cl − 、Br − 、及びI − からなる群から選択される、[1]に記載の方法。
[5]
触媒が、MgF 2 と、CsCl、LiCl、NaCl、KCl、LiF、NaF、KF、及び/又はCsFの1以上を含む、[1]に記載の方法。
[6]
触媒が、フッ素化又は塩素化MgO、フッ素化又は塩素化CaO、フッ素化又は塩素化Li 2 O、フッ素化又は塩素化Na 2 O、フッ素化又は塩素化K 2 O、及びフッ素化又は塩素化Cs 2 Oからなる群から選択される少なくとも1種類のハロゲン化金属酸化物を含む、[1]に記載の方法。
[7]
触媒が、0価の金属、0価の金属合金、又はこれらの組合せを含む、[1]に記載の方法。
[8]
0価の金属又は0価の金属合金が、場合によっては担持されており、Pd、Pt、Rh、Ru、Ir、Os、Fe、Co、Ni、Cu、Mo、Cr、Mn、及び組合せからなる群から選択される少なくとも1種類の金属を含む、[1]に記載の方法。
[9]
0価の金属又は0価の金属合金が、MgO上に担持されているPd、Pt、Ru、Rh、及び/又はIrの1以上を含む、[1]に記載の方法。
[10]
0価の金属合金が、ステンレススチール合金、モネル合金、インコネル合金、ハステロイ合金、インコロイ合金、及びこれらの組合せからなる群から選択される、[1]に記載の方法。
Claims (10)
- (i)1種類以上の金属ハロゲン化物;(ii)1種類以上のハロゲン化金属酸化物;(iii)1種類以上の0価の金属又は金属合金;(iv)これらの組合せ;からなる群から選択される触媒の存在下で1,2−ジクロロ−1,1,2−トリフルオロエタン(HCFC−123a)を脱塩化水素化して、CFO−1113を含む反応生成物を生成させる;
ことを含む、クロロトリフルオロエチレン(CFO−1113)の製造方法。 - HCFC−123aの転化率が少なくとも5重量%であり、クロロトリフルオロエチレンへの選択率が少なくとも70重量%であり、反応生成物は10重量%未満のCFO−1112を含む、請求項1に記載の方法。
- 脱塩化水素化工程の相当部分を480℃〜550℃の温度において行う、請求項2に記載の方法。
- 触媒が少なくとも1種類の金属ハロゲン化物を含み、成分の金属は、Cr3+、Fe3+、Mg2+、Ca2+、Ni2+、Zn2+、Pd2+、Li+、Na+、K+、及びCs+からなる群から選択され、成分のハロゲンは、F−、Cl−、Br−、及びI−からなる群から選択される、請求項1に記載の方法。
- 触媒が、MgF2と、CsCl、LiCl、NaCl、KCl、LiF、NaF、KF、及び/又はCsFの1以上を含む、請求項1に記載の方法。
- 触媒が、フッ素化又は塩素化MgO、フッ素化又は塩素化CaO、フッ素化又は塩素化Li2O、フッ素化又は塩素化Na2O、フッ素化又は塩素化K2O、及びフッ素化又は塩素化Cs2Oからなる群から選択される少なくとも1種類のハロゲン化金属酸化物を含む、請求項1に記載の方法。
- 触媒が、0価の金属、0価の金属合金、又はこれらの組合せを含む、請求項1に記載の方法。
- 0価の金属又は0価の金属合金が、場合によっては担持されており、Pd、Pt、Rh、Ru、Ir、Os、Fe、Co、Ni、Cu、Mo、Cr、Mn、及び組合せからなる群から選択される少なくとも1種類の金属を含む、請求項1に記載の方法。
- 0価の金属又は0価の金属合金が、MgO上に担持されているPd、Pt、Ru、Rh、及び/又はIrの1以上を含む、請求項1に記載の方法。
- 0価の金属合金が、ステンレススチール合金、モネル合金、インコネル合金、ハステロイ合金、インコロイ合金、及びこれらの組合せからなる群から選択される、請求項1に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201462046340P | 2014-09-05 | 2014-09-05 | |
US62/046,340 | 2014-09-05 | ||
US14/843,076 | 2015-09-02 | ||
US14/843,076 US9850188B2 (en) | 2014-09-05 | 2015-09-02 | Process for producing chlorotrifluoroethylene |
JP2017512799A JP6701178B2 (ja) | 2014-09-05 | 2015-09-03 | クロロトリフルオロエチレンの製造方法 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017512799A Division JP6701178B2 (ja) | 2014-09-05 | 2015-09-03 | クロロトリフルオロエチレンの製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2020125347A JP2020125347A (ja) | 2020-08-20 |
JP6965397B2 true JP6965397B2 (ja) | 2021-11-10 |
Family
ID=55436885
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017512799A Active JP6701178B2 (ja) | 2014-09-05 | 2015-09-03 | クロロトリフルオロエチレンの製造方法 |
JP2020081064A Active JP6965397B2 (ja) | 2014-09-05 | 2020-05-01 | クロロトリフルオロエチレンの製造方法 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017512799A Active JP6701178B2 (ja) | 2014-09-05 | 2015-09-03 | クロロトリフルオロエチレンの製造方法 |
Country Status (9)
Country | Link |
---|---|
US (3) | US9850188B2 (ja) |
EP (1) | EP3189025B1 (ja) |
JP (2) | JP6701178B2 (ja) |
KR (1) | KR102593719B1 (ja) |
CN (1) | CN107074692B (ja) |
CA (1) | CA2960177C (ja) |
ES (1) | ES2856409T3 (ja) |
MX (1) | MX2017002829A (ja) |
WO (1) | WO2016036909A1 (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106565413B (zh) * | 2016-10-17 | 2019-04-09 | 邵武华航新材料有限公司 | 一种气相催化脱氯化氢制备三氟氯乙烯的方法 |
JP6842310B2 (ja) * | 2017-02-06 | 2021-03-17 | 学校法人 関西大学 | 1−クロロ−2,2−ジフルオロエチレンの製造方法 |
WO2019152972A1 (en) * | 2018-02-05 | 2019-08-08 | Honeywell International Inc. | Gas phase process for chlorotrifluoroethylene |
JP7252771B2 (ja) * | 2019-02-06 | 2023-04-05 | 学校法人 関西大学 | 1-クロロ-2,2-ジフルオロエチレンの製造方法 |
CN112876336B (zh) * | 2019-11-29 | 2022-05-06 | 浙江蓝天环保高科技股份有限公司 | 一种三氟氯乙烯的制备方法 |
CN110975893B (zh) * | 2019-12-18 | 2023-04-18 | 浙江工业大学 | 用于二氟一氯甲烷高温裂解制四氟乙烯和六氟丙烯的金属氟化物催化剂、其制备方法和应用 |
CN113004117B (zh) * | 2021-04-22 | 2021-08-13 | 泉州宇极新材料科技有限公司 | 气相脱卤化氢制备3,3,3-三氟丙炔的方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8530708B2 (en) * | 2003-07-25 | 2013-09-10 | Honeywell International Inc. | Processes for selective dehydrohalogenation of halogenated alkanes |
RU2006142354A (ru) * | 2004-05-01 | 2008-06-10 | Хонейвелл Интернэшнл, Инк. (Us) | Способ получения галоолефинов |
US9040759B2 (en) * | 2007-07-06 | 2015-05-26 | Honeywell International Inc. | Preparation of fluorinated olefins via catalytic dehydrohalogenation of halogenated hydrocarbons |
US20100324345A1 (en) | 2009-06-22 | 2010-12-23 | Honeywell International Inc. | SYSTEMS AND PROCESSES FOR CFO-1113 FORMATION FROM HCFC-123a |
-
2015
- 2015-09-02 US US14/843,076 patent/US9850188B2/en active Active
- 2015-09-03 ES ES15838643T patent/ES2856409T3/es active Active
- 2015-09-03 MX MX2017002829A patent/MX2017002829A/es unknown
- 2015-09-03 CA CA2960177A patent/CA2960177C/en active Active
- 2015-09-03 KR KR1020177006246A patent/KR102593719B1/ko active IP Right Grant
- 2015-09-03 JP JP2017512799A patent/JP6701178B2/ja active Active
- 2015-09-03 WO PCT/US2015/048239 patent/WO2016036909A1/en active Application Filing
- 2015-09-03 EP EP15838643.3A patent/EP3189025B1/en active Active
- 2015-09-03 CN CN201580047879.8A patent/CN107074692B/zh active Active
-
2017
- 2017-12-22 US US15/852,794 patent/US10577295B2/en active Active
-
2019
- 2019-09-10 US US16/566,158 patent/US20200071247A1/en not_active Abandoned
-
2020
- 2020-05-01 JP JP2020081064A patent/JP6965397B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
KR20170053624A (ko) | 2017-05-16 |
EP3189025A1 (en) | 2017-07-12 |
US9850188B2 (en) | 2017-12-26 |
EP3189025A4 (en) | 2018-04-11 |
US10577295B2 (en) | 2020-03-03 |
CN107074692A (zh) | 2017-08-18 |
CA2960177A1 (en) | 2016-03-10 |
JP2020125347A (ja) | 2020-08-20 |
CN107074692B (zh) | 2020-07-21 |
KR102593719B1 (ko) | 2023-10-25 |
WO2016036909A1 (en) | 2016-03-10 |
JP6701178B2 (ja) | 2020-05-27 |
EP3189025B1 (en) | 2021-01-06 |
MX2017002829A (es) | 2017-06-15 |
CA2960177C (en) | 2023-12-12 |
US20190002374A1 (en) | 2019-01-03 |
ES2856409T3 (es) | 2021-09-27 |
US20160068455A1 (en) | 2016-03-10 |
US20200071247A1 (en) | 2020-03-05 |
JP2017525745A (ja) | 2017-09-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6965397B2 (ja) | クロロトリフルオロエチレンの製造方法 | |
US10329227B2 (en) | Process for the preparation of 2,3,3,3-tetrafluoropropene | |
JP6088618B2 (ja) | ヘキサフルオロ−2−ブテンの製造方法 | |
KR101388042B1 (ko) | 통합된 HFC 트랜스-1234ze 제조 공정 | |
EP2699534B1 (en) | PROCESS FOR PRODUCING TRANS-1233zd | |
KR101386906B1 (ko) | HFC-245fa로 부터 HFO 트랜스-1234ze를 제조하는방법 | |
JP5705962B2 (ja) | ヘキサフルオロ−2−ブテンの製造方法 | |
JP6763431B2 (ja) | 1−クロロ−1,2−ジフルオロエチレンの製造方法 | |
JP2018527369A (ja) | 1,2−ジクロロ−3,3,3−トリフルオロプロペンから2−クロロ−3,3,3−トリフルオロプロペンを製造する新規な方法 | |
JP5805812B2 (ja) | 統合hfcトランス−1234ze製造方法 | |
JP2017014160A (ja) | 1,2−ジクロロ−3,3,3−トリフルオロプロペンの製造方法 | |
EP2534120B1 (en) | Process for producing fluorine-containing alkene |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200601 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20200601 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20210531 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210824 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20211004 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20211020 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6965397 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |