EP1474233A2 - Katalysatorzusammensetzung zur oxichlorierung - Google Patents

Katalysatorzusammensetzung zur oxichlorierung

Info

Publication number
EP1474233A2
EP1474233A2 EP03704531A EP03704531A EP1474233A2 EP 1474233 A2 EP1474233 A2 EP 1474233A2 EP 03704531 A EP03704531 A EP 03704531A EP 03704531 A EP03704531 A EP 03704531A EP 1474233 A2 EP1474233 A2 EP 1474233A2
Authority
EP
European Patent Office
Prior art keywords
metal
catalyst
catalyst composition
composition according
salt
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.)
Withdrawn
Application number
EP03704531A
Other languages
German (de)
English (en)
French (fr)
Inventor
Christian Kuhrs
Ruprecht Meissner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Corp
Original Assignee
BASF SE
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
Priority claimed from DE2002104608 external-priority patent/DE10204608A1/de
Priority claimed from DE2002136254 external-priority patent/DE10236254A1/de
Application filed by BASF SE filed Critical BASF SE
Priority to EP10180596A priority Critical patent/EP2314374A1/de
Publication of EP1474233A2 publication Critical patent/EP1474233A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/72—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
    • 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
    • B01J27/122—Halides of copper
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
    • C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/15—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination
    • C07C17/152—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination of hydrocarbons
    • C07C17/156—Preparation of halogenated hydrocarbons by replacement by halogens with oxygen as auxiliary reagent, e.g. oxychlorination of hydrocarbons of unsaturated 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
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
    • B01J23/8933—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/8946—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali or alkaline earth 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/613—10-100 m2/g
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/615—100-500 m2/g
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/63—Pore volume
    • B01J35/633—Pore volume less than 0.5 ml/g
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/63—Pore volume
    • B01J35/635—0.5-1.0 ml/g
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation

Definitions

  • the present invention relates to a catalyst composition for the oxychlorination of ethylene, comprising a mixture of metal salts on a support, said metal salts being applied to the support in such proportions that the catalyst composition contains 3 to 12% by weight of copper as the copper salt , 0 to 3% by weight of an alkaline earth metal as the alkaline earth metal salt, 0 to 3% by weight of an alkali metal as the alkali metal salt, 0.001 to 0.1% by weight, preferably 0.005 to 0.05% by weight, of at least one metal from the group of ruthenium, rhodium, palladium, osmium, iridium and platinum and / or 0.0001 to 0.1% by weight, preferably 0.001 to 0.05% by weight of gold, as a corresponding metal salt, in the case of gold also as tetrachlorogoldic acid (HAuCl 4 ), all weight percentages being based on the total weight of the catalyst, including the support material.
  • the invention further relates to a process for the preparation of 1,2 dichloroethane by oxychlorination of ethylene, characterized by the reaction of a mixture of ethylene, oxygen or oxygen-containing gas and hydrogen chloride to 1,2-dichloroethane by means of a catalyst of the above composition.
  • Oxychlorination of ethylene to 1,2-dichloroethane is a well known process in which ethylene is reacted with hydrogen chloride and oxygen or with an oxygen-containing gas (e.g. air) in the gas phase and usually in the presence of a catalyst.
  • Suitable catalysts generally contain as a catalytically active component a copper compound which has been deposited on a carrier substance, preferably copper chloride on a carrier substance.
  • the supported catalysts used therefore usually contain what are known as promoters, by means of which the effectiveness of catalytically active copper chloride on supported substances is improved.
  • promoters include alkali metal chlorides, in particular potassium chloride and cesium chloride, alkaline earth metal chlorides, in particular magnesium chloride, or else chlorides of rare earth metals, in particular cerium chloride.
  • alkali metal chlorides in particular potassium chloride and cesium chloride
  • alkaline earth metal chlorides in particular magnesium chloride
  • chlorides of rare earth metals in particular cerium chloride.
  • EP-A 0 582 165 describes a catalyst composition comprising a support which has an active metal composition which contains 2 to 8% by weight of copper as copper chloride, 0.2 to 2% by weight of an alkali metal, 0.1 to 9 wt .-% of a rare earth metal and 0.05 to 4 wt .-% of a metal from group ILA of the periodic table (alkaline earth metals).
  • EP-A 0 375 202 discloses a catalyst composition for oxychlorination, comprising a mixture of metal chlorides on a support, which essentially contains a mixture of copper chloride, magnesium chloride and potassium chloride in such proportions that the catalyst composition 3 to 9% by weight of copper, 0.2 to 3% by weight of magnesium and 0.2 to 3% by weight of potassium.
  • No. 4,446,249 describes a catalytically active composition for a fluidized bed catalyst in which, on the carrier substance ⁇ -Al 2 O 3 , before the copper chloride is deposited, 0.5 to 3% by weight of at least one metal from the group potassium, lithium , Rubidium, cesium, alkaline earth metals or rare earth metals or mixtures of these elements are deposited.
  • the catalytically active copper chloride is then deposited on the carrier particles.
  • This two-step application of the active metal components to the carrier substance means that the catalyst particles produced by this process have less tendency to adhere to one another. This property is particularly advantageous when the catalyst is used as a fluidized bed.
  • the selectivity with which ethylene is converted in the oxychlorination reaction into the desired end product 1,2-dichloroethane - and not into the by-products customary in oxychlorination - is strongly dependent on the catalyst composition used. Especially in reactions with high ethylene conversion, too many by-products are still obtained when using the catalyst compositions which have been customary to date.
  • Fluidized bed catalysts for the oxychlorination of ethylene to 1,2-dichloroethane must therefore not only be optimized in terms of activity and selectivity, but also have a "sticking" -free swirl behavior. It can be observed that copper-rich catalysts have a greater tendency to stick together than low-copper catalysts.
  • a catalyst composition for the oxychlorination of ethylene comprising a mixture of metal salts on a support, said metal salts being applied to the support in such proportions that the catalyst composition
  • % preferably 0.005 to 0.05% by weight, of at least one metal selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium and platinum and / or 0.0001 to 0.1% by weight, preferably 0.001 to 0.05% by weight of gold, as a corresponding metal salt or tetrachlorogoldic acid, comprises, wherein all weight percentages are based on the total weight of the catalyst including support material.
  • the presence of small amounts of a salt of the platinum metals, which include ruthenium, rhodium, palladium, osmium, iridium and platinum, or the presence of small amounts of corresponding gold compounds in the catalyst composition used increase the conversion of the starting materials ethylene and hydrogen chloride significantly, but without to reduce the selectivity for the formation of 1,2 dichloroethane. This ultimately results in a higher yield of 1,2 dichloroethane.
  • the fluidization behavior is not influenced by the addition of small amounts of the metal salts mentioned above.
  • the corresponding oxyhalides, the oxides or the halides of the platinum metals or gold, in particular the chlorides of the platinum metals or gold are preferably used as the metal salts of the platinum metals or gold.
  • ruthenium salt in particular the presence of ruthenium chloride, in the quantitative ratio defined above in the catalyst composition is further preferred.
  • a gold salt in particular of gold chloride or tetrachlorogoldic acid, in the quantitative ratio defined above in the catalyst composition is particularly preferred.
  • CO and CO 2 are in a ratio of approximately 1: 1 to each other.
  • Circulation reactor processes are these by-products of oxychlorination
  • Aluminum oxide, silica gel, pumice stone and clay can be used as the carrier substance for the catalyst composition according to the invention.
  • the use of aluminum oxide as the carrier substance is preferred.
  • the specific surface area of the carrier substance before the metal salt deposition is preferably in the range from 20 to 400 m 2 / g, more preferably 75 to 200 m Ig.
  • Common carrier substances for oxychlorination catalysts preferably have pore volumes in the range from 0.15 to 0.75 cm 3 / g, and the average particle sizes are preferably in the range from 30 to 500 ⁇ m.
  • the proportion of particles with a diameter smaller than 45 ⁇ m is 30% or 5%, the BET surfaces being 170 m 2 / g or 150 m 2 / g.
  • the invention further relates to a process for the preparation of 1,2 dichloroethane for the oxychlorination of ethylene with catalysis of a catalyst composition according to the invention.
  • Ethylene, hydrogen chloride and molecular oxygen are brought into contact with a catalyst composition according to the invention at temperatures from 80 to 300 ° C., preferably at 210 to 260 ° C. in the gas phase.
  • the molecular oxygen can be used as such or in the form of an oxygen-containing gas mixture, e.g. Air to be discharged.
  • an oxygen-containing gas mixture e.g. Air to be discharged.
  • the molar ratios of the starting materials used in the process according to the invention are generally 5: 1 to 3: 1 for hydrogen chloride: oxygen, preferably approximately 4: 1 and generally approximately 1: 2 for ethylene: hydrogen chloride.
  • Hydrogen chloride based on the reaction 2 C 2 H 4 + 4 HC1 + O 2 a 2 C 2 H 4 CI 2 + 2 H 2 O, in slightly sub-stoichiometric amount, so that it is ensured that hydrogen chloride is converted almost completely in one reactor run.
  • ethylene is run in an even greater excess.
  • the ratio of ethylene: HCl: O 2 is preferably chosen so that ethylene is also converted as far as possible in one reactor pass.
  • the reaction pressure is in the range from 1 to 20 bar, preferably from 1 to 8 bar.
  • the reactor material used is usually based on iron (stainless steel) or based on a nickel alloy.
  • glass can also be used as the reactor material.
  • the catalyst can be used in the process according to the invention both as a fixed bed and as a fluidized bed. If the catalyst is used as a fluidized bed in the process according to the invention, it is preferably in the fluid state. This generally occurs at speeds in the range of 1 to 100 cm / s. If the catalyst is used as a fixed bed in the process according to the invention, it is preferably used in the form of hollow cylinders or ring tablets, the end faces of which are rounded off both towards the outer edge and towards the edge of the inner bores.
  • This preferably used fixed bed catalyst form is either hollow cylinders or ring tablets made up of catalytically active material, preferably a carrier material shaped into hollow cylinders or ring tablets, to which a catalytically active composition is applied.
  • the outside diameter of the hollow catalyst cylinder or ring tablets is 3 to 20 mm, preferably 3 to 10 mm, particularly preferably 3 to 7 mm, in particular 3.5 to 6.5 mm, and the inside diameter is 0.1 to 0 , 7 times the outer diameter.
  • the length of the hollow catalyst cylinder or ring tablets is 0.2 to 2 times, preferably 0.3 to 1.8 times, particularly preferably 0.4 to 1.6 times the outer diameter.
  • the radius of curvature of the end faces is 0.01 to 0.5 times, preferably 0.05 to 0.4 times, particularly preferably 0.1 to 0.2 times the outer diameter.
  • EP 1 127 618 AI Fixed bed catalysts of a form as described in EP 1 127 618 AI are thus an integral part of the present invention and are incorporated by reference.
  • the invention further relates to a process for the preparation of 1,2 dichloroethane by oxychlorination of ethylene with catalysis of a fixed bed catalyst with a composition according to the invention and optionally a form according to EP 1 127 618 AI.
  • aqueous solution for impregnating the carrier substance To prepare an aqueous solution for impregnating the carrier substance, the required amounts of the suitable metal compounds, preferably in the form of their hydrates, are dissolved in water. The aqueous solution is then applied to the carrier substance. The carrier substance impregnated in this way is then, if appropriate, filtered off from the remaining aqueous phase and finally dried. Filtration is not necessary if the carrier substance is brought into contact with a volume fraction of the aqueous solution which is not greater than is sufficient to saturate the carrier substance.
  • a catalyst composition according to the invention was prepared by impregnating the carrier substance with an aqueous solution, which was obtained as follows:
  • a catalyst composition was prepared in the same way with the same proportions by weight of copper chloride, magnesium chloride and potassium chloride, but without ruthenium chloride (catalyst B). Both oxychlorination catalysts (catalysts A and B) were used in a fluidized bed reactor made of glass, to which the starting materials ethylene, air and hydrogen chloride were fed and which was kept at 232 ° C., 243 ° C. and 254 ° C. bed temperature. The reactor was operated at a pressure of 4 bar with an amount of 500 g of the catalyst of the corresponding composition.
  • a further catalyst composition according to the invention was produced in accordance with Example 1, but instead of ruthenium chloride, palladium chloride was used as a promoter to produce catalyst C with 4.5% by weight Cu, 1.5% by weight Mg, 0.4% by weight K and To obtain 0.01 wt .-% Pd.
  • a further catalyst composition according to the invention was prepared in accordance with Example 1, but instead of ruthenium chloride, gold chloride was used as a promoter to produce catalyst D with 4.5% by weight Cu, 1.5% by weight Mg, 0.4% by weight K and To obtain 0.005% by weight of Au.

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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)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
EP03704531A 2002-02-05 2003-02-04 Katalysatorzusammensetzung zur oxichlorierung Withdrawn EP1474233A2 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP10180596A EP2314374A1 (de) 2002-02-05 2003-02-04 Katalysatorzusammensetzung zur Oxichlorierung

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE10204608 2002-02-05
DE2002104608 DE10204608A1 (de) 2002-02-05 2002-02-05 Katalysatorzusammensetzung zur Oxychlorierung
DE10236254 2002-08-07
DE2002136254 DE10236254A1 (de) 2002-08-07 2002-08-07 Katalysatorzusammensetzung zur Oxychlorierung
PCT/EP2003/001093 WO2003066214A2 (de) 2002-02-05 2003-02-04 Katalysatorzusammensetzung zur oxichlorierung

Publications (1)

Publication Number Publication Date
EP1474233A2 true EP1474233A2 (de) 2004-11-10

Family

ID=27735650

Family Applications (2)

Application Number Title Priority Date Filing Date
EP10180596A Withdrawn EP2314374A1 (de) 2002-02-05 2003-02-04 Katalysatorzusammensetzung zur Oxichlorierung
EP03704531A Withdrawn EP1474233A2 (de) 2002-02-05 2003-02-04 Katalysatorzusammensetzung zur oxichlorierung

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP10180596A Withdrawn EP2314374A1 (de) 2002-02-05 2003-02-04 Katalysatorzusammensetzung zur Oxichlorierung

Country Status (9)

Country Link
US (2) US7126035B2 (ja)
EP (2) EP2314374A1 (ja)
JP (2) JP4121459B2 (ja)
KR (1) KR100976897B1 (ja)
CN (1) CN1627989A (ja)
AU (1) AU2003206831A1 (ja)
RU (1) RU2004126865A (ja)
TW (1) TWI255736B (ja)
WO (1) WO2003066214A2 (ja)

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TWI341218B (en) * 2005-11-14 2011-05-01 Oxy Vinyls Lp Catalyst compositions and process for oxychlorination
EP2198958B1 (en) * 2008-12-17 2017-11-08 Clariant Prodotti (Italia) SpA Catalysts for oxychlorination of ethylene to 1.2-dichloroethane
EP2208528A1 (en) * 2008-12-23 2010-07-21 Süd Chemie - Catalysts Italia S.R.L. Catalysts for fixed bed oxychlorination of ethylene to 1.2-dichloroethane
US20100310441A1 (en) * 2009-06-05 2010-12-09 Basf Corporation Catalytic Article for Removal of Volatile Organic Compounds in Low Temperature Applications
CN102188975B (zh) * 2011-03-09 2013-01-23 浙江工业大学 一种负载型镍基双组分催化剂及其应用
EP2914378B1 (en) * 2012-11-05 2020-05-20 BASF Corporation Catalyst for the oxychlorination of ethylene to 1, 2-dichloroethane
JP6509807B2 (ja) * 2013-03-15 2019-05-08 オキシ ヴィニールズ，エルピー ジクロロエタンへのエチレンのオキシ塩素化のための触媒及びプロセス
WO2016189121A1 (en) * 2015-05-28 2016-12-01 Evolva Sa Biosynthesis of phenylpropanoids and phenylpropanoid derivatives
CN105126879B (zh) * 2015-07-15 2018-01-02 内蒙古大学 一种负载型钙钛矿乙烷氧氯化制氯乙烯催化剂的制备方法
CN108144632B (zh) * 2018-01-22 2020-11-03 西安元创化工科技股份有限公司 一种甲烷氧氯化的二氧化钌催化剂及其制备方法
EP4182079A1 (en) * 2020-07-14 2023-05-24 SABIC Global Technologies B.V. Catalysts for hydrogenation of aromatic containing polymers and uses thereof

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JP2005516757A (ja) 2005-06-09
WO2003066214A3 (de) 2004-02-05
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AU2003206831A1 (en) 2003-09-02
KR100976897B1 (ko) 2010-08-18
JP2008194691A (ja) 2008-08-28
JP4121459B2 (ja) 2008-07-23
US7902411B2 (en) 2011-03-08
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US7126035B2 (en) 2006-10-24
US20050020864A1 (en) 2005-01-27
EP2314374A1 (de) 2011-04-27

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