MX389255B - Proceso para la produccion de clorotrifluoroetileno. - Google Patents

Proceso para la produccion de clorotrifluoroetileno.

Info

Publication number
MX389255B
MX389255B MX2017002829A MX2017002829A MX389255B MX 389255 B MX389255 B MX 389255B MX 2017002829 A MX2017002829 A MX 2017002829A MX 2017002829 A MX2017002829 A MX 2017002829A MX 389255 B MX389255 B MX 389255B
Authority
MX
Mexico
Prior art keywords
chlorotrifluoroethylene
trifluoroethane
hcfc
dichloro
production
Prior art date
Application number
MX2017002829A
Other languages
English (en)
Other versions
MX2017002829A (es
Inventor
Haiyou Wang
Hsueh Sung Tung
Original Assignee
Honeywell Int Inc
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 Honeywell Int Inc filed Critical Honeywell Int Inc
Publication of MX2017002829A publication Critical patent/MX2017002829A/es
Publication of MX389255B publication Critical patent/MX389255B/es

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/25Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/23Preparation of halogenated hydrocarbons by dehalogenation
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06Halogens; Compounds thereof
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06Halogens; Compounds thereof
    • B01J27/08Halides
    • B01J27/10Chlorides
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06Halogens; Compounds thereof
    • B01J27/08Halides
    • B01J27/12Fluorides
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06Halogens; Compounds thereof
    • B01J27/128Halogens; Compounds thereof with iron group metals or platinum group metals
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06Halogens; Compounds thereof
    • B01J27/132Halogens; Compounds thereof with chromium, molybdenum, tungsten or polonium
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/38Separation; Purification; Stabilisation; Use of additives
    • C07C17/42Use of additives, e.g. for stabilisation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00Acyclic saturated compounds containing halogen atoms
    • C07C19/08Acyclic saturated compounds containing halogen atoms containing fluorine
    • C07C19/10Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
    • C07C19/12Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine having two carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/02Boron or aluminium; Oxides or hydroxides thereof
    • B01J21/04Alumina
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/10Magnesium; Oxides or hydroxides thereof
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/18Carbon
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/10Constitutive chemical elements of heterogeneous catalysts of Group I (IA or IB) of the Periodic Table
    • B01J2523/11Lithium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/10Constitutive chemical elements of heterogeneous catalysts of Group I (IA or IB) of the Periodic Table
    • B01J2523/12Sodium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/10Constitutive chemical elements of heterogeneous catalysts of Group I (IA or IB) of the Periodic Table
    • B01J2523/13Potassium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/10Constitutive chemical elements of heterogeneous catalysts of Group I (IA or IB) of the Periodic Table
    • B01J2523/15Caesium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/10Constitutive chemical elements of heterogeneous catalysts of Group I (IA or IB) of the Periodic Table
    • B01J2523/17Copper
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/20Constitutive chemical elements of heterogeneous catalysts of Group II (IIA or IIB) of the Periodic Table
    • B01J2523/22Magnesium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/20Constitutive chemical elements of heterogeneous catalysts of Group II (IIA or IIB) of the Periodic Table
    • B01J2523/23Calcium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/20Constitutive chemical elements of heterogeneous catalysts of Group II (IIA or IIB) of the Periodic Table
    • B01J2523/27Zinc
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/60Constitutive chemical elements of heterogeneous catalysts of Group VI (VIA or VIB) of the Periodic Table
    • B01J2523/67Chromium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/60Constitutive chemical elements of heterogeneous catalysts of Group VI (VIA or VIB) of the Periodic Table
    • B01J2523/68Molybdenum
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/70Constitutive chemical elements of heterogeneous catalysts of Group VII (VIIB) of the Periodic Table
    • B01J2523/72Manganese
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/80Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
    • B01J2523/82Metals of the platinum group
    • B01J2523/821Ruthenium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/80Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
    • B01J2523/82Metals of the platinum group
    • B01J2523/824Palladium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/80Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
    • B01J2523/82Metals of the platinum group
    • B01J2523/825Osmium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/80Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
    • B01J2523/82Metals of the platinum group
    • B01J2523/827Iridium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/80Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
    • B01J2523/82Metals of the platinum group
    • B01J2523/828Platinum
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/80Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
    • B01J2523/84Metals of the iron group
    • B01J2523/842Iron
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/80Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
    • B01J2523/84Metals of the iron group
    • B01J2523/845Cobalt
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00Constitutive chemical elements of heterogeneous catalysts
    • B01J2523/80Constitutive chemical elements of heterogeneous catalysts of Group VIII of the Periodic Table
    • B01J2523/84Metals of the iron group
    • B01J2523/847Nickel
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06Halogens; Compounds thereof
    • B01J27/138Halogens; Compounds thereof with alkaline earth metals, magnesium, beryllium, zinc, cadmium or mercury

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  • 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)

Abstract

La presente invención se refiere, al menos en parte, a un proceso para preparar clorotrifluoroetileno (CFO-1113) a partir de 1,2-dicloro-1,1,2-trifluoroetano (HCFC-123a). En ciertos aspectos, el proceso incluye la deshidrocloración de 1,2-dicloro-1,1,2-trifluoroetano (HCFC-123a) en presencia de un catalizador seleccionado del grupo que consiste en (i) uno o más haluros metálicos; (ii) uno o más óxidos metálicos halogenados; (iii) uno o más metales de valencia cero o aleaciones metálicas; (Iv) combinaciones de los anteriores.
MX2017002829A 2014-09-05 2015-09-03 Proceso para la produccion de clorotrifluoroetileno. MX389255B (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201462046340P 2014-09-05 2014-09-05
US14/843,076 US9850188B2 (en) 2014-09-05 2015-09-02 Process for producing chlorotrifluoroethylene
PCT/US2015/048239 WO2016036909A1 (en) 2014-09-05 2015-09-03 Process for producing chlorotrifluoroethylene

Publications (2)

Publication Number Publication Date
MX2017002829A MX2017002829A (es) 2017-06-15
MX389255B true MX389255B (es) 2025-03-20

Family

ID=55436885

Family Applications (1)

Application Number Title Priority Date Filing Date
MX2017002829A MX389255B (es) 2014-09-05 2015-09-03 Proceso para la produccion de clorotrifluoroetileno.

Country Status (9)

Country Link
US (3) US9850188B2 (es)
EP (1) EP3189025B1 (es)
JP (2) JP6701178B2 (es)
KR (1) KR102593719B1 (es)
CN (1) CN107074692B (es)
CA (1) CA2960177C (es)
ES (1) ES2856409T3 (es)
MX (1) MX389255B (es)
WO (1) WO2016036909A1 (es)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
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
EP3749628A4 (en) * 2018-02-05 2021-11-24 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
WO2024204829A1 (ja) * 2023-03-31 2024-10-03 ダイキン工業株式会社 精製された1,1,2-トリフルオロエタン(hfc-143)の製造方法、及びhfc-143を含有する組成物

Family Cites Families (5)

* Cited by examiner, † Cited by third party
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
KR20070004990A (ko) * 2004-05-01 2007-01-09 허니웰 인터내셔널 인코포레이티드 할로-올레핀의 제조
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
JP6271431B2 (ja) * 2011-09-30 2018-01-31 ハネウェル・インターナショナル・インコーポレーテッドHoneywell International Inc. 2,3,3,3−テトラフルオロプロペンの製造方法

Also Published As

Publication number Publication date
CA2960177C (en) 2023-12-12
MX2017002829A (es) 2017-06-15
JP2017525745A (ja) 2017-09-07
JP6965397B2 (ja) 2021-11-10
WO2016036909A1 (en) 2016-03-10
CN107074692B (zh) 2020-07-21
US9850188B2 (en) 2017-12-26
CA2960177A1 (en) 2016-03-10
ES2856409T3 (es) 2021-09-27
JP6701178B2 (ja) 2020-05-27
US20190002374A1 (en) 2019-01-03
EP3189025A4 (en) 2018-04-11
US20200071247A1 (en) 2020-03-05
KR20170053624A (ko) 2017-05-16
KR102593719B1 (ko) 2023-10-25
EP3189025A1 (en) 2017-07-12
US20160068455A1 (en) 2016-03-10
EP3189025B1 (en) 2021-01-06
US10577295B2 (en) 2020-03-03
CN107074692A (zh) 2017-08-18
JP2020125347A (ja) 2020-08-20

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